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Product-Market Fit

Finding Product-Market Fit for SaaS

How founders validated their ideas and found product-market fit. Lessons on pivoting, customer discovery, and building what people actually want to pay for.

Real founder strategies. Delivered weekly.

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Allan Wille of Klipfolio describes product-market fit as the moment you go from push to pull — when you stop having to convince people and they start coming to you. Rob Walling knew Drip hadn't found it when MRR flatlined at $7,000 for months. Clate Mask at Infusionsoft had the strangest signal of all: customers were furious and demanding, because they relied on the product so heavily they couldn't function without it.

Product-market fit is the thing every founder chases, and these episodes show what finding it actually looks like. It's almost never a clean, sudden moment. Aseem Badshah of Socedo went from $50 customers to $1,000 customers after repositioning around a different use case. Max Kolysh pivoted Zinc three times over several years before hitting $5M ARR with the right product. Brandon Foo spent a full year building Paragon as a backend product nobody wanted before pivoting to integrations.

You'll learn how founders distinguish between polite interest and real demand. at Brightpearl discovered they were selling to the wrong customer segment after years of struggle. raised prices 12x and found their real customers happily paid, while the wrong ones disappeared. Fyxer found fit almost immediately because they had three years of field services data showing exactly what the market needed.

Derek O'Carroll
RunRunIt

Whether you're still searching for product-market fit or worried you might be losing it, these conversations will sharpen your instincts for reading the signals.

Podcast Episodes

Browse by topic:AllBootstrappingFirst CustomersProduct-Market FitEnterprise SalesProduct-Led GrowthPricing & MonetizationFounder-Led SalesPositioning & DifferentiationChurn & RetentionContent & Inbound MarketingExits & AcquisitionsFundraisingAI-Powered SaaS
He Sold a Vitamin for 7 Years Then Found Product-Market Fit - Adam Markowitz

Adam Markowitz, Drata

He Sold a Vitamin for 7 Years Then Found Product-Market Fit

Adam Markowitz is the co-founder and CEO of Drata, a trust management platform that helps companies automate compliance, security assurance, and third-party risk management. Adam never planned to be a founder. He wanted to be an astronaut. That led him to aerospace engineering, and in 2008 he landed his dream job working on NASA's Space Shuttle program. Three years later, NASA retired it. So he taught himself to code and built Portfolium, a platform that helped students prove their skills with real project work instead of resume bullet points. It took years, but he eventually got it into over 500 universities. The company was acquired for $43 million. But it was during those long university sales cycles that Adam experienced a moment he never forgot. A CIO at the largest four-year public university system in the country asked him to prove his company's security posture. He couldn't. His entire company was built on the idea of proving things with evidence - and here he was, asking a customer to just take his word for it. That pain became the seed for Drata. After Portfolium's acquisition, Adam got the band back together - same co-founders, same early engineering team. They spent six months building the first version, talking to dozens of companies and auditors to validate the problem before writing code. Then they did something most founders wouldn't: they refused to sell to anyone until they'd used their own product to get SOC 2 compliant first. When they finally launched, product-market fit was immediate. Adam signed 100 customers in six weeks and 1,000 within the first year. The difference from his edtech days was stark - he'd gone from selling a vitamin to selling a painkiller. Adam used three strategies to accelerate Drata's growth to $100M ARR: 1. Dogfooding before selling - using Drata to earn their own SOC 2 gave instant credibility 2. Building an Auditor Alliance that kept auditors independent while making audits faster 3. A "give before you take" AWS partnership that made Drata a top 5 ISV on Marketplace by bringing thousands of new customers to the platform Today, Drata has over 8,000 customers across 60 countries, more than 600 employees, and crossed $100 million in ARR before its fourth birthday. The company has raised over $300 million.

Frequently Asked Questions

What is product-market fit for SaaS?+

Allan Wille of Klipfolio describes it as the shift from push to pull: when you stop having to convince people and they start coming to you. At Pendo, Todd Olson knew he had it when usage data showed customers embedding the product into daily workflows. Clate Mask of Infusionsoft had an unconventional signal: customers were angry and demanding because they relied on the product so heavily. Product-market fit shows up in retention and urgency, not just signups.

How do you know when you have product-market fit?+

Rob Walling knew Drip didn't have it when MRR flatlined at $7K for months. He pivoted the product's positioning and saw immediate acceleration. Aseem Badshah of Socedo realized he had it when customers jumped from paying $50 to $1,000 a month after he repositioned around a different use case. Fyxer got instant product-market fit because they had three years of field services data showing exactly what customers needed. The signal is always the same: retention stays strong and customers start pulling the product from you.

How long does it take to find product-market fit?+

Max Kolysh pivoted Zinc three times over several years before hitting $5M ARR with the right product. Paragon spent a full year building a backend product nobody wanted before pivoting to integrations. Derek O'Carroll at Brightpearl learned they were selling to the wrong customer segment after years of struggle. But Fyxer found fit almost immediately by layering AI onto their existing services data. It took Infusionsoft years of iteration and frustrated customers before their product clicked. There's no shortcut; the speed depends on how close you start to the real problem.

What's the difference between traction and product-market fit?+

Rob Walling had traction at Drip with paying customers, but $7K MRR that wouldn't budge meant he hadn't found fit yet. Brightpearl had revenue and customers but was targeting the wrong segment, so growth stalled. RunRunIt had users but only found product-market fit after raising prices 12x and seeing that the right customers happily paid. Traction measures activity; product-market fit shows up when customers stay, expand, and refer others without you pushing.

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How Livestorm Lost Product-Market Fit at $9M ARR - Gilles Bertaux

Gilles Bertaux, Livestorm

How Livestorm Lost Product-Market Fit at $9M ARR

Gilles Bertaux is the co-founder and CEO of Livestorm, a webinar platform for enterprise marketers. In 2016, Gilles and his three co-founders built Livestorm as a university project. They had two months to build a product, get some users, and present it to a panel. So they built a browser-based webinar tool. On presentation day, they livestreamed all the student presentations. Hundreds of people watched remotely. And they loved it. Even former bosses from internships told them to skip the job hunt and pursue this full-time. They were young with no real responsibilities. So they went for it. They spent weeks collecting leads and hosted a launch webinar to showcase the product. It was a disaster. Gilles tried to bring a marketing exec from a big e-commerce company on screen. Instead, his CTO popped up and said 'I think there is a bug.' Live. In front of everyone. Growth came slowly through SEO, Quora, and partnering with bigger companies to get in front of their audiences. No outbound. No sales team. Gilles wrote three to four articles a day and answered questions on Quora that nobody else was touching. For five years, Quora alone drove 10-15% of total organic traffic. Then COVID hit. In one year, Livestorm went from $2 million to $9 million in ARR. But it was chaos. Support tickets jumped from 200 to 20,000 per month. Servers crashed for an entire day. They had to throw money at AWS just to keep things running, and their margins got crushed. After COVID, things got even messier. They tried building a meeting product, then a sales demo product. Suddenly Livestorm looked like a smaller version of Zoom. Customers had no compelling reason to pick them instead. Livestorm had lost product-market fit. In 2022, they tried to raise a Series C. Investors said no. So Gilles had to flip the company to profitability. That meant going after bigger customers who would pay more and stick around longer. But his sales team only knew how to handle inbound leads. He had to replace almost the entire team. Gilles rebuilt Livestorm's product-market fit by narrowing to enterprise webinars for European marketers in banking and pharma - a niche that most founders would run from. There were moments where he wondered if the product could really make the leap. Part of him questioned whether Livestorm's best days were already behind them. Today, Livestorm generates nearly $20 million in ARR with 3,500 customers and has raised $35 million.

How a Bootstrapped SaaS Hit $5.3M ARR in Under 2 Years - Adam Fard

Adam Fard, UX Pilot

How a Bootstrapped SaaS Hit $5.3M ARR in Under 2 Years

Adam Fard is the founder of UX Pilot, an AI platform that helps product design teams create and ship great user experiences faster. In 2023, Adam was running a successful UX agency when ChatGPT and LLMs started taking off. He began experimenting with ways to apply AI to his team's design processes and built a Figma plugin that helped users work through UX frameworks and activities. Then during a user interview, someone asked a simple question: "I have all these ideas on my canvas, but can I turn them into something visual? Can I create a wireframe?" That question stuck with him. He started looking around to see if any tools could actually generate wireframes from text input. He found a few products claiming to do it. But when he tested them, he realized they were faking it. They were just swapping existing templates and personalizing the copy. None of them could truly generate a layout from scratch. There was a technical reason for that. Creating wireframes with AI was genuinely hard. So Adam started working on it himself. He explored fine-tuning LLMs, hired AI researchers, and tested component-based approaches. He spent four or five months iterating. Slowly, things started working. The outputs became stable enough to use. He added Figma integration so designers could bring wireframes into their existing workflow. Within six or seven months of that original user question, UX Pilot hit $10K MRR. But growth created a new problem. Adam hired too slowly. At $30K MRR, he kept questioning whether this was the ceiling. He added one engineer, waited, added another, waited again. Looking back, he says he should have hired five people at once instead of dragging out the process. Adam built a bootstrapped SaaS that now generates over $5 million in ARR with a team of 30 and over 15,000 paying subscribers. He proved that a bootstrapped SaaS can compete with well-funded competitors by focusing narrowly on one hard problem - AI wireframe generation for professional design teams - and shipping a code-first product that enterprise teams actually wanted.

Finding Product-Market Fit After 2 Years of Almost Nothing - Tito Goldstein

Tito Goldstein, Teambridge

Finding Product-Market Fit After 2 Years of Almost Nothing

Tito Goldstein is the Co-Founder and CEO of TeamBridge, a composable workforce operating system for hourly workers that serves over 500,000 employees across 200+ enterprise customers. Tito Goldstein and his co-founder Arjun were two of the first principal product designers at Uber. After interviewing thousands of Uber drivers worldwide, they realized something powerful: drivers were choosing Uber despite lower pay because of the agency and self-service the app provided. They raised a $3 million seed round to bring that same experience to the 60% of the global workforce who are hourly employees stuck with legacy tools. But after building their initial scheduling product, they hit a wall - two years of near-zero revenue and no product-market fit. The problem wasn't the market. It was the product. Customers kept saying they needed to stand out, not use the same cookie-cutter software as their competitors. Their secret sauce lived in spreadsheets and manual processes, not in a fixed scheduling tool. So Tito and Arjun made a gutsy call: throw out the scheduling product and rebuild as composable Legos. Customers could start with a template but configure 20% to match their unique workflows and differentiators. The new product outsold the previous two years of efforts in the first month. Product-market fit had arrived. Then it 3x'd, and 3x'd again. Today, TeamBridge powers NFL stadiums like the 49ers' Levi's Stadium, medical staffing agencies scaling from zero admin staff to multimillion-dollar businesses, and enterprises managing thousands of hourly workers with self-service automation.

How Qualia Found First Customers by Living in One's Basement - Nate Baker

Nate Baker, Qualia

How Qualia Found First Customers by Living in One's Basement

Nate Baker is the co-founder and CEO of Qualia, a software platform for title companies that helps coordinate the complex process of buying a home. Today, Qualia generates over $100 million in ARR with a team of 600 and has raised more than $200 million. In 2015, Nate was 21 years old and decided to build software for the real estate industry. He had no experience in that space. He didn't talk to any customers. He just did some research and decided that was the thing he was going to do. Then he started building. Still without talking to anyone. Nate admits this was a mistake. He and his co-founders got key things wrong about how the business would work. They wasted months building things they eventually threw away. It wasn't until they found their first customer that they started making real progress. Their first customer was Barry Feingold, a state senator in Massachusetts who also ran a real estate law firm. Barry believed in the vision, taught them the industry, made introductions, and helped them understand what actually mattered. The relationship was unconventional: Nate and the first 25 employees rotated through living in Barry's basement. New hires would get a call Sunday night: "Your onboarding is in Andover. You're going to live in Barry's basement for two weeks. He's going to teach you title. You have to tutor his kids in math." But then Barry's existing software vendor found out he was working with Qualia and shut off his access overnight. Nate and his team didn't even have the core features built yet. They had to figure it out fast. It became the most productive month in company history. Barry didn't just become a customer - he introduced Qualia to his competitors. Those network-based relationships became the foundation for the first 10 customers. Nate learned that your first customers must come from your network, not cold outreach.

From $150K Consulting Trap to $1M ARR AI SaaS - Ibby Syed

Ibby Syed, Cotera

From $150K Consulting Trap to $1M ARR AI SaaS

Ibby Syed pivoted his AI SaaS from a consulting trap to $1M ARR in under a year. Learn his playbook for escaping the services treadmill and building a product-led AI agent platform. In 2022, Ibby Syed joined his co-founder Tom right after YC. They built a customer analytics platform and grew it to $150K ARR over 18 months. But something wasn't right. Customers weren't logging into the product - they'd call with a question, get an answer, and disappear. Ibby realized they'd accidentally built a consulting business, not an AI SaaS. Then came the wake-up call. A customer asked them to extract topics from support tickets. Ibby built a data science solution that was slow and clunky. His co-founder Tom tried the newly released OpenAI API instead - and with just 100 lines of code, solved the problem better. That was the pivot moment. They stopped doing services, fired some customers, and rebuilt Cotera as an AI agent builder. The difference was immediate: deals became easier to close. Instead of building custom solutions, they taught customers how to build their own AI SaaS workflows. Today, Cotera has 15 enterprise customers, a team of 10, and generates over $1M ARR. In this episode, Ibby breaks down exactly how to escape the consulting trap, why early revenue can be a dangerous signal, and how to build an AI SaaS that customers actually log into.

Zero Revenue for 8 Months From One SaaS Pricing Mistake - Ryan Wang

Ryan Wang, Assembled

Zero Revenue for 8 Months From One SaaS Pricing Mistake

Ryan Wang is the co-founder and CEO of Assembled, an AI platform for customer support that helps companies manage both human and AI agents more efficiently. In 2016, Ryan was a machine learning engineer at Stripe. He and his co-founders spent two years building before launching in 2020 - the same day WHO declared COVID a global pandemic. Their momentum vanished. About a quarter of demos didn't show up. Their SaaS pricing model - usage-based with no minimums - meant customers could scale to zero without leaving. It took 8 months to earn their first dollar of revenue. In 2016, Ryan was a machine learning engineer at Stripe. He and his future co-founder Brian built ML tools to automate support tickets, but they realized the real problem wasn't automation - it was workforce management. That became the spark for Assembled. The three co-founders spent two years building before they launched in 2020. They lined up a TechCrunch story, hit the front page of Hacker News, and then their launch landed the same day the World Health Organization declared COVID a global pandemic. Momentum vanished. About a quarter of demos didn't show up. It took them eight months to earn their first dollar of revenue. The SaaS pricing trap: When they finally got customers, they had usage-based pricing with no minimums. Customers could scale usage to zero. When usage flatlined during the pandemic, the team blamed themselves before realizing customers weren't leaving because of the product - they were just cutting costs. How Ryan fixed the SaaS pricing problem: 1. Shifted focus from chasing growth to serving customers who were getting value 2. Met customers in person, sat with support leaders, and built what actually mattered 3. Added pricing minimums to prevent revenue from dropping to zero 4. Built sticky features that justified the investment That hands-on approach worked for about 10 customers. Then it broke at 50. Onboarding took weeks. Some features worked in demos but failed in production. So they rebuilt onboarding to get it down to days and cleaned up the product so it could scale. Eventually they grew from their early customers to dozens more and reached 8-figure ARR.

Why This Bootstrapped SaaS Founder Only Invested $400K - Sam Darawish

Sam Darawish, Everflow

Why This Bootstrapped SaaS Founder Only Invested $400K

Sam Darawish is the co-founder and CEO of Everflow, a partner-marketing platform that helps companies manage their affiliate programs, influencers, and performance-marketing campaigns. Sam started in online marketing in the early 2000s, working at one of the first affiliate and pay-per-click companies in San Francisco. When the iPhone launched in 2008, he and his two co-founders saw a chance to bring what they had learned from desktop to mobile. They bootstrapped Moola Media, one of the first mobile affiliate networks, and built their own tracking platform because there were no good third-party options for mobile at the time. In 2013, Opera acquired Moola Media for $50 million. During the three-year earn-out, Sam kept hearing the same complaint from marketers: no one liked the existing affiliate-marketing software. When the earn-out ended in 2016, the founders invested a few hundred thousand dollars of their own money into Everflow and did not pay themselves for the first couple of years. The first six to seven months of their bootstrapped SaaS journey were spent talking to potential customers and refining ideas. Then they decided to go all in at Affiliate Summit in Las Vegas, renting a booth with nothing more than screenshots of the product. Two prospects from that conference became their first paying customers - even though one made them sign an agreement to take over the software if the company failed. By early 2018, the bootstrapped SaaS hit $1M ARR with just 10 people and turned profitable. Today, Everflow has grown to nearly $30M ARR with 1,200 customers and 120 team members across San Francisco, Montreal, Amsterdam, and Dubai - all without raising external funding.

5% Retention Exposed a Product-Market Fit Problem - David Shim

David Shim, Read AI

5% Retention Exposed a Product-Market Fit Problem

David Shim is the co-founder and CEO of Read AI, a meeting intelligence platform that helps teams capture, analyze, and act on insights from their meetings. David Shim had already built and sold a company for $200 million to Snapchat when he spotted his next opportunity: a reflection in someone's glasses during a Zoom call. During the pandemic, David noticed a fellow meeting participant's glasses reflecting ESPN.com - they were both distracted on the same call. That moment sparked a question: could AI measure meeting engagement in real-time? After cold-emailing Zoom founder Eric Yuan to validate the idea (Eric confirmed Zoom wasn't building it), David raised $10 million and launched Read AI on the Zoom App Store. The initial product showed engagement analytics - sentiment scores, attention metrics, who was distracted. Users thought it was cool. But cool doesn't pay the bills. Monthly retention sat at just 5%. Users would try the product, see their meeting scores, and never come back. David had built a dashboard when he should have built a decision-making tool. Product-market fit was nowhere in sight. The breakthrough came when OpenAI released ChatGPT. David's team combined their proprietary engagement analytics with LLM-powered summaries, creating what they call the "narration layer" - capturing not just what was said, but how people reacted. Tone, emotions, head nods, who looked away. The transcript tells you the words; the narration layer tells you the truth. Retention climbed: 5% to 10%, then 30%, 40%, 50%, and finally 81%. Product-market fit was proven when 81% of users were still active 30 days after signup. Today Read AI adds 12 million accounts per year with zero ad spend. Every meeting report shared is a viral loop - all participants receive the notes, non-users see the value, and accounts multiply.

How Mailtrap Found Product-Market Fit With Zero Marketing - Sergiy Korolov

Sergiy Korolov, Mailtrap

How Mailtrap Found Product-Market Fit With Zero Marketing

Sergiy Korolov is the co-CEO of Railsware, a product studio that helps companies design, build, and scale successful software products, and the co-founder of Mailtrap, an email testing and delivery platform trusted by developers worldwide. Back in 2011, Sergiy's team made a massive mistake. They accidentally sent 20,000 test billing emails from their staging environment straight to real customers. The chaos was immediate. Customers were confused and upset, wondering if they'd actually been charged or not. To make sure it never happened again, they built a small internal tool to stop test emails from reaching real inboxes. When they shared it with the Ruby on Rails community, something unexpected happened. Developers loved it, and Mailtrap spread purely through word of mouth, eventually attracting more than 200,000 users. For the next five years, Mailtrap stayed free. It was a side project until 2016, when Sergiy finally decided to turn it into a real business. Instead of guessing, his team ran over 100 customer interviews and dug into usage data to guide pricing and product decisions. It took another four years to reach $1 million in ARR. Growth was slow and steady, not the overnight success story people imagine. And just as things started to pick up, a new challenge appeared. Customers wanted Mailtrap to handle production email sending too. That meant turning a product built to avoid sending emails into one that had to deliver them flawlessly. It was a risky move. The shift created a whole new set of problems, from dealing with spam attacks and deliverability issues to fighting brand confusion about what Mailtrap actually did. Suddenly, a product known for blocking emails had to prove it could deliver them reliably. Sergiy and his team spent months rebuilding their infrastructure, tightening security, and designing tools that gave developers more visibility and control. It wasn't glamorous work, but it paid off. Mailtrap evolved into a trusted, full-stack email platform used by teams around the world. Today, Mailtrap generates seven-figure ARR with a 40-person team and more than 100,000 monthly active users.

How Firing SMB Customers Led to 8x Enterprise Sales Growth - Bernard Aceituno

Bernard Aceituno, Stack AI

How Firing SMB Customers Led to 8x Enterprise Sales Growth

Bernard Aceituno is the Co-Founder and CEO of Stack AI, a no-code AI platform that helps enterprises build AI agents to automate back-office workflows. Bernard Aceituno spent 10 years in academia, researching AI and reinforcement learning at MIT. He was on track to become a professor or join a research lab like DeepMind. But he realized that while research was intellectually stimulating, it wasn't solving the immediate, manual problems he saw in the corporate world. So he dropped out of his PhD program to build a startup. His first idea was a tool for machine learning teams to manage datasets. It got some traction, but he noticed his customers were struggling more with connecting data than managing it. That insight led to a pivot: Stack AI, a drag-and-drop builder for enterprise AI workflows. The launch was scrappy. They posted the MVP on Hacker News and Y Combinator's Bookface. It exploded. In just two days, they booked 20 customer meetings. But that early success created a new problem: everyone wanted it. For the first year, they tried to serve everyone - SMBs, startups, and enterprises. It was chaotic. SMBs churned quickly. Startups had small budgets. Bernard made the hard decision to fire his smaller customers and focus exclusively on enterprise sales in the mid-market segment - companies with 100-1,000 employees. This segment had real budget, real problems, and moved faster than the Fortune 500. The result: an 8x revenue multiplier in one year, with enterprise sales cycles closing in 2-6 weeks instead of months. Today, Stack AI serves over 100 enterprise customers like Nubank, has raised $16M, and is generating high seven figures in ARR with a team of 35.

How Proof Lost Product-Market Fit After a 100x Spike - Pat Kinsel

Pat Kinsel, Proof

How Proof Lost Product-Market Fit After a 100x Spike

Pat Kinsel is the founder and CEO of Proof (formerly Notarize), a platform that helps businesses and individuals verify identities and notarize documents online. The idea started when Pat sold his previous startup to Twitter. While trying to close the deal, a notary error nearly derailed the entire transaction. He realized the system was broken, archaic, and ripe for disruption. But instead of building software immediately, Pat spent months validating the idea. He built a simple Unbounce landing page, ran Google Ads, and proved that people were searching for "online notary." Then, he spent years lobbying to change state laws to make digital notarization legal. It was an early signal of product-market fit - demand existed, but the infrastructure to serve it didn't. For the first few years, growth was painfully slow. The company lost money on every transaction due to high notary costs - negative 110% gross margins. Then COVID hit. Demand spiked 100x overnight. Everyone needed remote notarization. But this blessing was also a curse - many of these customers were just looking for a temporary fix, not a long-term solution. When the pandemic waned, Proof effectively lost product-market fit with these urgency buyers and had to rebuild. Pat refocused the company on enterprise customers and expanded the platform beyond notarization into broader identity verification and transaction security. Today, Proof is approaching $100M in ARR, serves thousands of enterprise customers, and has become the standard for secure digital transactions - proof that product-market fit sometimes has to be found more than once.

How Pendo Found Product-Market Fit After Two Failures - Todd Olson

Todd Olson, Pendo

How Pendo Found Product-Market Fit After Two Failures

Todd Olson is the founder and CEO of Pendo, a product experience platform that helps software companies understand user behavior and improve their applications. In the late 1990s, during the dot-com boom, Todd started his first company which eventually led to a promising acquisition offer. But the board thought Todd and his co-founder were too young to handle negotiations themselves. So they brought in someone else. The deal fell apart, the company pivoted to services, and Todd ended up leaving. His next startup struggled from the start. Todd made what he now calls an idiotic mistake. He assumed CEOs had to be non-technical, so he gave the role to a sales guy friend. They couldn't find product-market fit. Rally Software eventually acquired them, which Todd describes as a good soft landing more than a success story. Todd stayed on at Rally as head of product. That's where he discovered the problem that would become Pendo. He had no visibility into how users were actually using their product. He couldn't guide them when they got stuck. So in 2013, he left to build the solution he wished he had. This time, Todd obsessed over product-market fit from day one. He built auto-tracking into Pendo so customers didn't need developers adding tracking code everywhere. But nobody was searching for "product analytics plus in-app guidance." The category didn't exist. With inbound marketing not an option, Todd went manual. He leveraged his VC network for introductions and started messaging heads of product on LinkedIn. For the first year, he focused on the number of installs as the most important metric. By October 2014, Todd noticed one company using Pendo constantly. He called them and closed his first paying customer at $500 a month. Today, Pendo generates over $200 million ARR with about 880 employees and has raised over $479 million to date. Todd's journey from two failed startups to product-market fit at scale is a masterclass in validating before scaling.

How Repositioning This AI SaaS Unlocked 7-Figure Growth - Flo Crivello

Flo Crivello, Lindy

How Repositioning This AI SaaS Unlocked 7-Figure Growth

Flo Crivello is the founder and CEO of Lindy, an AI SaaS platform that lets anyone build AI agents to automate workflows without code. In 2020, Flo Crivello was running TeamFlow, a virtual office startup that raised over $50 million. But when people returned to offices, growth flatlined. With no path forward, Flo pivoted to build Lindy, an AI SaaS platform for building AI agents. The idea came from his sales team asking if AI could automatically update Salesforce. Flo kept climbing the "ladder of abstraction" until he realized he was building an AI SaaS agent platform. In March 2023, he launched with a demo video that generated 70,000 waitlist signups. But the AI SaaS product was terrible. It would send emails that literally said "the user wants me to send an email to 50 software engineers." Users were surprisingly forgiving because they understood they were early adopters. Flo's breakthrough came from repositioning. His AI SaaS started as "AI employee" - too futuristic for the broken product. He repositioned as "Zapier of AI," making the AI SaaS accessible by positioning against something familiar. Within months, Lindy hit product-market fit and grew to high 7-figures. This episode covers the brutal reality of pivoting an AI SaaS, why familiar positioning beats visionary messaging for early adoption, and how to know when your AI SaaS has reached product-market fit.

7 Years of Zero Revenue Then Product-Market Fit Hit - Rob Woollen

Rob Woollen, Sigma Computing

7 Years of Zero Revenue Then Product-Market Fit Hit

Rob Woollen is the Co-Founder and CTO of Sigma Computing, whose seven-year search for product-market fit led to building a data analytics platform that lets business users analyze cloud-scale data without writing SQL. Rob Woollen's journey of finding product-market fit is one of the longest in SaaS history. He founded Sigma Computing 11 years ago with a clear problem to solve: business users were stuck with spreadsheets while programmers got powerful cloud data tools. The first seven years were brutal. Rob and his co-founder raised $8M, hired a team of five, and built multiple prototypes - each one a "colossal failure." At one point, two founding engineers quit because they felt the company was "just swirling around." The team shrunk to three people for a year and a half. The breakthrough came in 2017 when their investors suggested meeting with Snowflake. In just 30 days before the meeting, Rob's team rebuilt their entire product to integrate with Snowflake's cloud data warehouse. At lunch, Snowflake's CEO said something they'd never heard before: "I want this. When can I start using this?" This was the first real sign of finding product-market fit after years of "polite feedback." But even after finding early traction and reaching $1M ARR, Rob made a controversial decision - rebuild the product again. He felt the interface still wasn't right, even though the company was finally making money. Today, Sigma Computing has crossed $100M in revenue with 600+ employees and 1,400+ customers.

Why Enterprise Buyers Almost Killed His SaaS - Jonathan Festejo

Jonathan Festejo, Salesbricks

Why Enterprise Buyers Almost Killed His SaaS

Jonathan Festejo is the CEO and co-founder of Salesbricks, a deal-closing platform that handles quoting, billing, and subscriptions for SaaS companies. Before Salesbricks, Jonathan ran RevOps for multiple unicorns. He knew the pain of "Quote-to-Cash" intimately. But when he started his own company, he made a classic SaaS go-to-market mistake: he built for the Enterprise first. He spent nearly two years over-engineering a robust platform designed to replace Salesforce CPQ. But when he tried to sell it, he hit a wall. Enterprise buyers had 3-month sales cycles, complex approval chains, and often decided to "do nothing" because switching was too risky. The breakthrough came when he pivoted his SaaS go-to-market strategy down-market. He realized that early-stage founders ($500K-$2M ARR) were the ones with the most urgent pain. They were hacking together Stripe and spreadsheets late at night and were desperate for a solution. Jonathan used these 3 strategies to find his first customers and reach $1M ARR: 1. Targeted founders who were personally doing billing at night - they felt the pain and could make instant buying decisions 2. Built a "Powered By Salesbricks" button into every contract sent, turning each transaction into a high-intent lead channel 3. Leveraged founder-to-founder referrals from his network, converting warm intros into paying customers By shifting his focus to founders, sales cycles dropped to 5 days. The product roadmap started writing itself based on real user feedback, and Salesbricks hit $1M ARR with over 100 customers.

Finding Product-Market Fit in a Category Nobody Asked For - Sam Naficy

Sam Naficy, Prodoscore

Finding Product-Market Fit in a Category Nobody Asked For

Sam Naficy is the CEO of Prodoscore, a SaaS platform that uses AI to show companies how work gets done by analyzing data from the cloud tools employees already use every day. Sam's startup journey began in 1998 when he built DTT (later renamed DTIQ), a SaaS company providing video and data analytics for restaurants, hotels, and retail. He scaled it to $55M ARR and 550 employees over two decades before it was acquired by Cisco's private equity firm. After stepping away, a close friend pitched him a new idea. Sam came on board as an investor. Then, just months before the pandemic hit, he stepped in as CEO of a pre-revenue startup. What he walked into was tough. Most people assumed Prodoscore was just another employee surveillance tool. Finding product-market fit meant flipping that narrative entirely - making the product employee-centric with personal dashboards and AI-driven recommendations instead of mouse tracking and screenshots. The process of finding product-market fit also meant narrowing a massive TAM. Prodoscore went from targeting "anyone with Salesforce" to 100+ seat mid-market companies, and then discovered staffing as their number one ICP - a vertical nobody on the team had predicted. Along the way, COVID brought outsized press coverage from CNBC and the Wall Street Journal to a 4-person company that wasn't ready to convert all that attention. Sam shares what he learned about timing, capital, and the patience required to educate a market that doesn't know it needs you yet. Today, Prodoscore is a high 7-figure ARR business with roughly 150 customers, 135,000 employees on the platform, and an AI engine that can predict employee attrition 90 days in advance with over 90% accuracy.

Why Excited Customers Still Said No - Rami Tamir

Rami Tamir, Salto

Why Excited Customers Still Said No

Rami Tamir is the co-founder and CEO of Salto, a platform that helps teams manage and automate the configuration of enterprise SaaS apps like Salesforce, NetSuite, and Okta. Rami had already built and sold three startups to Cisco, Red Hat, and Oracle. But building Salto brought a whole new set of challenges for him and his co-founders. The idea came from a problem he kept running into at his last company. Making changes in tools like Salesforce should have been simple, but instead it was slow, frustrating, and full of errors. At first he thought it was his team's fault. Later, he realized almost every company using modern enterprise SaaS tools was dealing with the same thing. He and his co-founders self-funded the early product and started showing mockups to potential customers. The feedback was enthusiastic - one prospect even said she wanted to hug him. But when they came back with a working product, the excitement disappeared. It was not what people thought they were going to get. That was a critical product-market fit lesson even for a serial entrepreneur: early feedback can send you in the wrong direction when you are pitching a vague idea. People fill in the gaps with their own imagination, and when the real product arrives, it does not match. Once they had a real product to sell, they hit a new problem. Even though the pain was real, most buyers were not looking for a solution - Salto was creating a new enterprise SaaS category. Every deal was a grind because there was no line item in the budget for what they were selling. Rami's approach was to target discretionary budgets - pricing the product so a director-level buyer could approve it without a lengthy procurement process. This let them land fast and then expand into more applications and teams. Just as they started to gain traction, the 2023 downturn hit. Budgets vanished. Deals stalled. Even happy customers churned. Salto made tough changes - they raised prices, focused on larger companies, and rebuilt their sales motion for a longer enterprise cycle. Eventually, that pivot paid off. Today, Salto is an 8-figure ARR business with hundreds of enterprise customers and $69 million in funding from Bessemer, Lightspeed, Excel, and Salesforce Ventures.

How Product-Led Growth Took Metabase to 8-Figure ARR - Sameer Al-Sakran

Sameer Al-Sakran, Metabase

How Product-Led Growth Took Metabase to 8-Figure ARR

Sameer Al-Sakran is the founder and CEO of Metabase, an open-source BI tool that helps teams quickly turn raw data into charts and dashboards. In 2014, Sameer started building Metabase as a side project at Expa, a startup incubator - just a simpler way to answer basic questions from a database without needing a complex data stack. It was not supposed to be a company. But once he realized others shared his frustration with bloated, over-engineered tools, he spun it out and raised a $2M seed round. Then he did something most SaaS founders would not dare - he waited four years before charging a single dollar. Even when customers tried to pay, Sameer said no. One wanted to embed Metabase in their product, but the deal came with heavy demands. Another required a 50-page legal contract. He turned both down, choosing to focus on building the right product before chasing revenue. When they finally monetized, it was not through a polished sales motion. It was a buried CTA deep in the admin panel. No salespeople. No support. Just a credit card form. Strangers started paying $300/month to remove the Metabase logo from charts. That scrappy product-led growth flow pulled in close to six figures in ARR without a single sales call. But instead of doubling down on this signal, Sameer followed conventional wisdom. He built an enterprise edition, ran sales calls, and hired AEs. The business grew, but the momentum shifted. When they finally added a cloud self-service option, it took off and dwarfed the directly sold portion of the business. The detour through enterprise sales cost years. The product-led growth signal had been hiding in the self-serve motion all along. Sameer Al-Sakran built Metabase to 8-figure ARR and 70,000+ companies by returning to three core principles: win the taste test against Tableau and Looker, let the product sell itself through in-app CTAs, and accept the per-user pricing model customers actually wanted.

From $5K Deal to Unicorn - A SaaS Fundraising Story - Jenn Knight

Jenn Knight, AgentSync

From $5K Deal to Unicorn - A SaaS Fundraising Story

Jenn Knight is the co-founder and CTO of AgentSync, a company modernizing how insurance companies handle agent licensing, compliance, and onboarding. In 2018, Jenn was working at Dropbox while her co-founder (and now husband) Niji was at Zenefits. He saw firsthand how insurance companies were struggling to keep their agents licensed and compliant. No one had figured out a good solution. Niji became so convinced there was an opportunity that he quit his job to work on the idea from their kitchen, while Jenn kept her day job at Dropbox and built the product evenings and weekends. As tech outsiders trying to break into the insurance industry, they got a lot of pushback. People kept telling them this wasn't even a real problem. After months of building the product and talking to potential customers, they finally landed their first customer who paid $5,000 a year for their solution. But everything changed after a product demo when insurance professionals started listing all the ways AgentSync could make their lives easier. Their excitement showed the co-founders they were onto something big. In late 2019, the couple took a huge leap of faith. When they found out Jenn was pregnant, she quit her job at Dropbox. They decided to move to Denver, where they'd both work on AgentSync full-time without any funding lined up. The timing seemed terrible. The pandemic hit just months later, but instead of failing, they thrived. Their SaaS fundraising journey took off - they raised their seed round, then their Series A, and grew to 35 employees by the end of 2020, then to over 100 the following year. Today, AgentSync has achieved unicorn status through successful SaaS fundraising rounds, pulls in eight-figure revenue, has over 250 customers, and employs more than 200 people.

6 Weeks of Runway to Near 8-Figure Enterprise SaaS - Barb Hyman

Barb Hyman, Sapia

6 Weeks of Runway to Near 8-Figure Enterprise SaaS

In 2018, Barb Hyman was brought in to scale an existing HR tech startup called Predictive Hire. But within weeks, she discovered a harsh reality - the product was not working, the cap table was a mess, and the business needed a complete reset. She made the difficult decision to fire the entire team, including the founder. With just six weeks of runway left, she had to raise funding through convertible notes to keep the business alive. The next two years were a constant fight for survival. Some months, Barb was not sure they would make payroll. She and a small team rebuilt the product from scratch, pivoting to an AI-powered chat interview platform. They ran experiment after experiment to find the right approach to enterprise SaaS. Landing their first major customer, Qantas Airlines, took 15 trial runs over several years before they signed an enterprise SaaS deal. And just as they gained momentum, COVID hit, making it even harder to close new business. Barb tried to expand into the US market after raising a Series A, but the strategy failed. The sales hire used a spray-and-pray approach instead of focusing on verticals where they had product-market fit. After 18 months, Barb pulled out and moved to the UK instead, where the regulatory environment and cultural fit created better enterprise SaaS opportunities. Today, Sapia.ai is approaching eight figures in ARR with a team of 45 people. They have raised over $21 million in funding, and most of their pipeline comes from customer referrals. Barb's approach of overinvesting in customer relationships, writing handwritten Christmas cards, and sending personalized gifts has built a referral engine that outperforms traditional marketing.

From $0 to $1M ARR Through Competitive Differentiation - Vitaly Veksler

Vitaly Veksler, Vista Social

From $0 to $1M ARR Through Competitive Differentiation

Vitaly Veksler is the founder and CEO of Vista Social, a social media management platform for brands and agencies. In 2010, while working in corporate tech, Vitaly decided to build a social media management tool called Social Report. It was his first entrepreneurial venture, and over the next nine years he learned some tough lessons about building a startup. The biggest lesson? He spent years building advanced analytics features when his customers really needed a complete social media management solution. He had built just 10% of the product customers actually wanted. It took him nearly five years to realize that, and the competitive differentiation he thought he had in analytics turned out to be irrelevant because customers needed the full feature set. Once he finally pivoted to building the complete tool, things changed fast. Within three to six months of adding the missing features, the business started gaining real traction. Vitaly eventually sold Social Report in 2019. In 2020, he decided to take another shot with Vista Social, but this time in a much more competitive market. The social media management space had matured, with dozens of established players. But Vitaly had a key advantage - he deeply understood the customer and knew exactly where competitors were falling short. He and his small team of three built a product with feature parity in about 12 months. Their competitive differentiation strategy focused on three pillars: a modern, clean product versus competitors' bloated legacy systems, aggressive pricing, and exceptional one-on-one customer support. Instead of going after agencies immediately, they started with SMBs and creators who needed simple scheduling at a low price point. As the product matured, they expanded into higher-tier plans for their target ICP of agencies and social media managers. The bet paid off. Vista Social reached $1M ARR in less than two years. Today, the company has over 10,000 customers and a team of 15 people.

10 Customer Interviews That Reveal Why People Really Buy - Bob Moesta

Bob Moesta, The Re-Wired Group

10 Customer Interviews That Reveal Why People Really Buy

Bob Moesta is the founder, president, and CEO of The Re-Wired Group and co-creator of the Jobs to be Done framework with Clayton Christensen. In his 40 years working with products, he's helped over 3,500 companies bring their ideas to market and launched eight startups himself. As a dyslexic teenager, Bob couldn't make sense of traditional market research reports. Despite being told to stick to manual jobs, he refused to let his dyslexia hold him back. Everything changed when Bob noticed something surprising - many customers weren't just giving incomplete answers in interviews, they were actually lying to themselves about why they bought products. This led him to study intelligence interrogation techniques to uncover what really drives people to buy. Those insights helped companies like Basecamp, Facebook Marketplace, and Casper solve their growth challenges using Jobs to be Done interviews that go far deeper than traditional customer research. Bob explains why customers who ask for a "calendar feature" might really just need to see what time slots are available - and how that reframing turned a 9-month project into a 6-week build at Basecamp. He walks through the forces of progress model, showing how push, pull, anxiety, and habit interact to either drive or block a purchase decision. You'll also hear how InVideo used Jobs to be Done research to abandon the wrong customer segment and grow from zero to $25 million in six months, how Casper increased mattress sales 37% by identifying their real competitor (Zquil, not other mattress brands), and how one company cut their time-to-close in half by creating three different demos based on where buyers were in their decision journey.

$35/Month Flat-Rate SaaS Without Funding to 8 Figures - Martha Bitar

Martha Bitar, Flodesk

$35/Month Flat-Rate SaaS Without Funding to 8 Figures

Martha Bitar is the co-founder and CEO of Flodesk, an email marketing platform designed for small businesses and creators. She built a SaaS without funding from day one, proving that a bootstrapped company can compete with billion-dollar incumbents by solving a different problem. In 2019, Martha and her co-founder Rebecca launched Flodesk to make beautiful email marketing accessible to everyone. They focused on design and simplicity over complex features - the exact opposite of what incumbents were doing. Martha was working in partnerships at HoneyBook when she noticed a pattern: small business owners with massive Instagram followings could not get a single newsletter out. The problem was not content - it was design. Existing tools like MailChimp were built to solve hardware and software problems from 20 years ago, not the modern design challenges creators face today. Rebecca, a designer who had created templates for Rihanna and Linkin Park, had been sitting on this idea for three years. Her template shop's number one support ticket was customers buying beautiful designs that broke when implemented in other platforms. The validation process was intense. Martha booked 12+ customer calls per day, iterating on Figma prototypes after every single conversation. Their first prototype was a complete failure - users sank in their chairs confused. So they stripped everything down, removing features until only the essential remained. They did not start building until they made someone cry happy tears. Their flat-rate pricing model ($35/month unlimited) helped them stand out in a market dominated by per-subscriber pricing. They deliberately avoided a free tier, which meant every customer contributed revenue. The viral footer strategy - where every email sent displayed "Made in Flodesk" - combined with an affiliate program drove explosive growth to $1M ARR in just four months. Flodesk proves that building a SaaS without funding is not just possible - it can be a strategic advantage. The company generates over $27 million in ARR with 80,000 paying customers, competing with VC-backed giants by focusing on design, simplicity, and unconventional pricing.

18 Months to $10K MRR Then Compounding SaaS Growth - Colin Nederkoorn

Colin Nederkoorn, Customer.io

18 Months to $10K MRR Then Compounding SaaS Growth

Colin Nederkoorn is the co-founder and CEO of Customer.io, a platform that helps over 7,000 companies send personalized messages based on customer behavior and actions. Today the business generates $70 million in annual recurring revenue with a team of 250 people across 30 countries. But the early days looked nothing like that. In 2012, Colin and his co-founder John were working at a startup together. They started exploring ideas during lunch breaks, looking for something technically challenging, close to revenue, and built for their peers. Their original idea - a more sophisticated analytics product - fell flat when prospective users told them they already had 10 tools showing what people did on their website. What they needed was something to influence behavior. That feedback led to the pivot. They built a bare-bones product where customers would describe what campaign they wanted, and John would manually write MapReduce queries behind the scenes to make it work. They charged $10 a month and gated signups so Colin could talk to every single customer. The SaaS growth was painfully slow at first. Colin and John lived off savings and credit cards for years. Paid ads failed because the market did not have vocabulary for what they were building - terms like "triggered messages" and "segmentation" attracted the wrong buyers. A turning point came when Ramit Sethi told them they were wasting their email list by not communicating with subscribers until launch. Colin took that advice and started teaching conversion copywriting to their audience, building credibility in the email marketing space before Customer.io was even ready. That content-first approach became the foundation of their SaaS growth engine. By educating potential customers on how to write messages that convert, they created demand for the tool that would send those messages. It took 18 months to reach $10K MRR, but once compounding kicked in, the numbers got big fast. As Colin puts it, when you are compounding 50% or 80% year over year starting from $10M or $20M, the growth becomes massive. Chris Savage, CEO of Wistia, gave Colin another key insight during those early cash-strapped days: the question is not whether you need more money - it is whether you need more time. That reframing helped Colin extend runway creatively rather than raising too much capital too early, which he believes would have shortened their window to figure things out.

5 Years to $1M Then Vertical SaaS Took Off - Dan Uyemura

Dan Uyemura, PushPress

5 Years to $1M Then Vertical SaaS Took Off

Dan Uyemura is the co-founder and CEO of PushPress, a vertical SaaS platform for boutique gym owners including CrossFit studios, yoga studios, and martial arts gyms. In 2009, Dan was working as a front-end developer at Myspace while falling in love with CrossFit. His passion for fitness led him to open his own gym, and as a gym owner he quickly realized the existing software options were outdated and disconnected from what modern technology could deliver. Believing he could build something better, he recruited two friends - a developer and a designer - to start coding. Building the product proved far harder than expected. The team scrapped two complete versions before settling on their architecture. They launched in 2013, but growth was painfully slow. Dan describes the early days as "fighting Mike Tyson when you don't even know how to box yet." It took nearly five years of hand-to-hand combat sales and word-of-mouth growth to reach the first million in ARR. Behind the scenes, Dan was dealing with personal demons. A divorce, job loss, and drug addiction spiraled into a felony arrest that could have sent him to prison for 13 years. A judge's leniency gave him a second chance, and Dan channeled his obsessive energy into building PushPress instead of destructive habits. By 2017, Dan was ready to quit and go back to running his gym. Instead, he invested in an accelerator program that became a turning point. PushPress doubled revenue to $2M ARR, acquired a competitor's workout tracking product, and started building momentum. Then crisis hit again. A competitor acquired PushPress's partner company, forcing the team to race against time to build crucial features in-house or lose everything. That pressure pushed them to become a full-stack solution. Today, PushPress generates 8-figures in ARR, serves over 3,500 gym clients, and has grown to a team of about 100 people. They raised $11 million in funding at a $62 million post-money valuation after eight years of pitching investors. Dan's story is proof that building vertical SaaS in a market you deeply understand can overcome almost any obstacle.

How Firing 40% of Customers Ended a SaaS Churn Cycle - Caleb Avery

Caleb Avery, Tilled

How Firing 40% of Customers Ended a SaaS Churn Cycle

Caleb Avery is the founder and CEO of Tilled, a PayFac-as-a-Service platform that helps B2B software vendors embed and manage payment processing for their customers. In 2019, after four years of angel investing and consulting for vertical software platforms, Caleb spotted a pattern: companies processing $10 million a month on Stripe were leaving $800,000 a year in payment revenue on the table. The problem was not awareness - it was that switching off Stripe took six months of engineering time. Caleb spent 10 months as a solo founder validating whether he could compress that to one week. Once he convinced himself the idea was viable, he brought on a CTO and started building. The first version of the product was, in his words, "truly terrible." It took a full 18-month rebuild focused on white-label support and developer documentation to create something that could compete with Stripe. When COVID hit, Caleb's outbound sales and trade show strategy collapsed. With less than 500 LinkedIn followers, he pivoted to content marketing - hiring a ghostwriter for $800 a month and building a content library seven months before the product even launched. That bet on SaaS churn prevention through inbound paid off: LinkedIn drove 95% of Tilled's lead flow in the first year, getting them close to $1 million in ARR. But the rapid growth masked a SaaS churn problem. Of Tilled's first 50 customers, only 15-20 were finding real success on the platform. The rest consumed resources without scaling. Caleb made a gutsy call: he fired roughly 40% of his customers and narrowed the ICP to focus only on customers that matched the profile of those who were thriving. The result was 60-90 days of uncertainty followed by 25% month-over-month growth and eventually 500% year-over-year growth. A single podcast appearance also brought 36 channel partners inbound in 24 hours, opening a reseller channel that still drives deals today. Today, Tilled generates strong 7-figure revenue approaching 8 figures, serves around 100 customers, and has raised $40 million in capital.

From 46 Clicks to 20K Customers With SaaS Sales Strategy - Patrick Barnes

Patrick Barnes, AMP

From 46 Clicks to 20K Customers With SaaS Sales Strategy

Patrick Barnes is the co-founder and CEO of AMP, a multi-product SaaS platform that helps e-commerce merchants run their online businesses. In 2016, Patrick co-founded Advocately, a review management platform for SaaS companies. Growth was painfully slow at first, with the team struggling to convince potential customers of the product's value. Undeterred, Patrick and his co-founder persevered, scrapping together 2 to 4 new customers each month. Bootstrapping their startup forced them to be resourceful and laser-focused on customer needs. After nearly three years of hard work, G2 - a major player in the software review space - acquired Advocately. This experience from struggle to exit taught Patrick invaluable lessons about SaaS sales strategy, finding product-market fit, and the importance of persistence. In 2022, he teamed up with his longtime friend Cameron to tackle a growing problem in e-commerce. Merchants were overwhelmed by the need to juggle 25 to 40 different SaaS tools just to run their online stores. To build their initial solution, Patrick and Cameron acquired a small Shopify app with about 2,000 customers, which became the foundation of their new venture. They quickly applied SaaS best practices, redesigning the onboarding experience and implementing email marketing. The results were impressive. AMP hit its first million in ARR soon after the acquisition, but success also brought new challenges. When they launched an Amazon integration, expectations were sky high. They had 4,000 ideal customers who they were sure would love the new feature. But the launch fell flat with the email campaign generating just 46 clicks. As their team grew to about 50 employees, maintaining their customer-centric culture became increasingly difficult. Patrick's solution was mandating regular customer calls for everyone - from engineers to marketers - to ensure the entire team stayed deeply connected to user needs. Their SaaS sales strategy of relentless customer focus, combined with a philosophy that speed is the primary business strategy, paid off. Today, AMP serves around 20,000 customers, has raised $18.5 million in Series A funding, and generates eight figures in ARR.

Why His SaaS Go-to-Market Failed Then Worked Twice - Jake Stein

Jake Stein, Common Paper

Why His SaaS Go-to-Market Failed Then Worked Twice

Jake Stein is the co-founder and CEO of Common Paper, a platform that provides standardized contracts and contract management software for B2B software companies. In 2008, Jake and his co-founder Bob Moore started RJ Metrics, a business intelligence company, working out of Bob's attic without taking salaries for the first year and a half. Those early years were grueling as they bootstrapped for three years before raising venture capital. By 2012, they finally found product-market fit and grew the business, raising over $20 million. But their success was short-lived. In 2015, Amazon launched Redshift and disrupted their entire business model. Competitors like Looker - who later sold for $2-3 billion - had made architectural decisions that gave them an edge in the new landscape. RJ Metrics stopped growing, and Jake and Bob were forced to do painful layoffs of 25 people. They eventually sold to Magento in 2016 in what Jake describes as an okay exit. But the story didn't end there. Jake and Bob spun off a small feature from RJ Metrics into a new company called Stitch. Applying eight years of SaaS go-to-market lessons from their first venture, they built Stitch as a product-led company - and sold it for $60 million just two years later. Now with Common Paper, Jake faced a different SaaS go-to-market challenge. After six months of enterprise conversations that produced zero conversions, he discovered that his investor pitch about network effects wasn't the right sales pitch for buyers. Early-stage startups, on the other hand, signed up immediately when offered a useful tool that solved today's problem. Today, Common Paper has 140 paying customers, thousands of companies using their platform, and tens of millions of dollars in deals closed through their standard contracts - all built on a go-to-market strategy of giving away the most valuable part of their product for free.

A Year of Wrong Words Then SaaS Positioning Clicked - Michael Zuercher

Michael Zuercher, Prismatic

A Year of Wrong Words Then SaaS Positioning Clicked

Michael Zuercher is the co-founder and CEO of Prismatic, an embedded integration platform that helps SaaS companies build faster integrations for their customers. In 2003, Michael founded his first software company serving public safety agencies - law enforcement, fire departments, and 911 centers across the United States. Over 15 years, the company grew to $50 million in revenue with roughly 2,500 to 3,000 customers. But operating across 40 states meant building integrations for every region's unique requirements. By the time Bain Capital acquired the company, the engineering team had built over 600 integrations, and half of their R&D effort was dedicated to building and maintaining them. After leaving in 2018, Michael co-founded Prismatic in 2019 with two former colleagues, Justin and Beth. Their goal was to solve the integration problem they had lived with for over a decade. But they quickly ran into a challenge they hadn't anticipated: nobody knew what to call what they were building. The category "embedded iPaaS" didn't exist yet, and prospects kept confusing them with traditional integration platforms like Mulesoft and Zapier. The team spent the first eight to nine months validating the idea and building a prototype. Because their platform was an embedded product that customers would depend on in production, they couldn't ship a quick MVP. It took over a year to get a production-ready version to market. During that time, Michael handled all the sales himself and struggled to find the right SaaS positioning to explain how Prismatic was different. He heard "I don't understand how you're different than Mulesoft" more times than he can count. It took roughly a year of getting negative and positive reinforcement on sales calls before the SaaS positioning finally clicked. Around the $1 million ARR mark, Michael noticed a shift - conversations suddenly got easier, prospects understood the value faster, and the team had found early product-market fit. Today, Prismatic generates multiple seven figures in ARR, serves over 200 customers, and has a team of about 60 people. Their SaaS positioning journey proves that clear messaging can unlock growth faster than product improvements alone. SEO and paid ads remain the primary growth channels, complemented by outbound email that requires constant reinvention.

How to Sell a SaaS Business for 4x-8x on a Marketplace - Juan Ignacio Garcia

Juan Ignacio Garcia, Boopos

How to Sell a SaaS Business for 4x-8x on a Marketplace

Juan Ignacio Garcia is the founder and CEO of Boopos, a platform that makes selling a SaaS business simpler by combining a curated marketplace with built-in acquisition financing. Before starting Boopos, Juan tried to buy three businesses himself. Each time, he hit the same wall: no one would finance a small SaaS acquisition. Banks wanted tangible assets. VCs wanted hypergrowth. Revenue-based lenders like Capchase and Founderpath only funded working capital, not acquisitions. That gap in the market became Boopos. Today, Boopos offers term loans covering 40-70% of the acquisition price with no personal guarantee, pre-vets both buyers and sellers, and typically closes deals in under a week for financing approval. The platform focuses on profitable B2B SaaS businesses with at least 24 months of track record and strong customer retention. In this conversation, Juan walks through the entire process of selling a SaaS business on a marketplace. He explains how to prepare your P&L and legal documents, what drives valuation multiples from 4x to 8x, how to choose between self-serve marketplaces like Flippa, hybrid platforms like Acquire.com, and curated advisory models like Boopos. He also covers the buyer's side, including red flags to watch for during due diligence and how to evaluate whether a business is transferable. We also dig into the financing landscape for SaaS acquisitions, comparing SBA loans, alternative lenders, and cash buyers, and why many founders start with faster non-SBA financing and refinance later once the business is stabilized.

How Partnerships Drove $3M ARR in 9 Months - Ian Brodie

Ian Brodie, Levanta

How Partnerships Drove $3M ARR in 9 Months

Ian Brodie is the co-founder and CEO of Levanta, an affiliate marketing software platform built specifically for Amazon merchants. In 2020, Ian and Rob set out to launch a SaaS company and began talking to investors right away. However, as two recent college graduates with no product or engineering team, they were quickly laughed out of the room. Undeterred, the aspiring founders pivoted to starting a services company, with the goal of generating enough revenue to eventually self-fund their SaaS dream. They came up with a clever way to validate their new business idea by posting their services as gigs on Fiverr. Within days, they'd received over 100 responses and felt confident in launching their affiliate marketing agency. But for the next two years, transforming their agency into a SaaS company proved incredibly difficult. They managed to grow the services business to 7-figures, but it was barely profitable, and they were kept busy just keeping the business going. Eventually, they got a lucky break with an acquisition offer for Grovia for a mid-7-figure valuation. Which finally gave them the money and time to build their SaaS company. Learning from their past mistakes, Ian and Rob spent months rigorously validating the idea through customer interviews before investing in building an MVP. After years of trial and error, they finally got traction. Within 9 months of launch, their SaaS company Levanta hit over $230K in MRR, with over 650 brands and 2,500 affiliates on their platform. Their SaaS partnerships strategy with affiliate agencies drove nearly all of their growth without any paid marketing.

From $1M ARR to 40% Churn in One Month - Brett Martin

Brett Martin, Kumospace

From $1M ARR to 40% Churn in One Month

Brett Martin is the co-founder and president of Kumospace, a virtual office platform that helps remote teams to collaborate in real time. In 2020, Brett was running a venture capital fund and hosting monthly in-person networking events. When the pandemic hit, he was forced to use Zoom for these events, which he felt wasn't a great experience and kept thinking to himself that there had to be a better way. So when long-time friend and former co-founder Yang said he wanted to launch a startup, Brett suggested solving this video meeting problem and initially advised on the concept. After seeing early traction, Brett soon joined as co-founder. They launched in the middle of the pandemic and quickly attracted hundreds of thousands of users. When they started charging money the following year, their revenue skyrocketed to over $1 million ARR in just 2.5 months. But their celebrations were short-lived. Churn spiked to 40% in a month as customers used the product more for one-off events than daily work and so had little reason to renew their subscription. This crisis forced the founders to make the tough call. They scrapped their initial model, losing much of their revenue, and pivoted to a virtual office platform. But growing revenue was much slower and challenging this time around. However, fast forward to today, Kumospace serves millions of users, generates 7-figures in ARR with a team of just 16 people, and has raised $25 million in funding.

How Founder-Led Sales Built an 8-Figure Spend Management SaaS - Thejo Kote

Thejo Kote, Airbase

How Founder-Led Sales Built an 8-Figure Spend Management SaaS

Thejo Kote is the founder and CEO of Airbase, a spend management platform for mid-market and enterprise companies. In 2016, following the successful exit of his previous startup Automatic Labs to SiriusXM for $115 million, Thejo began brainstorming ideas for his next venture. At Automatic, managing company spending had been a constant pain point, and that experience planted the seed for what would become Airbase. But instead of jumping straight into code, Thejo spent six months interviewing CFOs to validate the problem. He hired a freelance designer to create high-fidelity software mockups and took those designs back to potential customers after every round of feedback. He did not start building until 10-12 CFOs told him they would sign up the moment the product existed. Thejo then used founder-led sales to close the first 15-20 customers himself before hiring his first sales leader. That first hire was a VP of sales, not a junior AE, which went against conventional wisdom. But as a solo founder without a co-founder handling go-to-market, Thejo needed someone who could write the sales playbook from scratch while he stayed focused on the product. The transition from founder-led sales to a VP-led sales organization got Airbase past 100 customers and into 8-figure ARR territory. The initial wedge was corporate card spend management, but Airbase has since expanded into AP automation, expense management, and guided procurement. Along the way, Thejo navigated a market flooded with heavily funded competitors by staying frugal, controlling runway, and deliberately slowing growth to build a sustainable business. Today Airbase has surpassed 8-figure ARR, grown to around 300 employees across 16 countries, and raised over $100 million in equity from investors including Menlo Ventures, Bain Capital Ventures, and First Round Capital.

3 Years of Pivots Before Finding Product-Market Fit - Greg Smith

Greg Smith, Thinkific

3 Years of Pivots Before Finding Product-Market Fit

Greg Smith is the co-founder and CEO of Thinkific, a platform for entrepreneurs and businesses to create, market, and sell online courses and other digital products. In 2005, Greg, a law student, began teaching LSAT prep courses in-person, later converting it into a $29 online course that eventually earned him $10k per month. Seeing growing demand for online courses, Greg and his brother Matt launched a basic product in 2012 to simplify creating and selling digital courses. In the first 3 years, they experienced numerous pivots and setbacks, struggling with the long process of finding product-market fit and acquiring customers. After failing to validate their early product concepts, the brothers shifted their strategy. They started manually building online courses for each new customer. This hands-on, time-intensive approach generated early revenue and gave the founders vital customer insights they needed to develop their software platform. In 2015, after launching their new software, they had a breakthrough moment when a webinar resulted in 20 customers immediately paying $1,000 each - the clearest sign yet of finding product-market fit. After 5 years of persistence and hard work, the founders hit $10 million ARR, fueled by customer referrals, content marketing, and strategic partnerships. Today, Thinkific, with a 280-person team, generates about $60 million in ARR and has raised over $200 million primarily through its IPO in 2021.

7 Years to Find Product-Market Fit and Hit $1M ARR - Stefan Debois

Stefan Debois, Pointerpro

7 Years to Find Product-Market Fit and Hit $1M ARR

Stefan Debois is the co-founder and CEO of Pointerpro, a software platform for professional services firms to create online assessments and automatically give personalized advice. In 2012, Stefan was feeling stuck. After working for 15 years in consulting, he wanted to start his own company. But he didn't have a great business idea. While still in his 9 to 5 job, Stefan made an iPad quiz app for his daughter's birthday party. It was just for fun, but it turned out to be a big hit. This gave Stefan an idea what if he made this quiz app better and put it online for free? So he spent his weekends improving the app and then released it, not expecting much. But then, something unexpected happened. The app quickly gained popularity. Teachers were using it in classes, and even AT&T was using it for HR events. Stefan saw a potential business and started interviewing his users to find out what they liked and didn't like. Once he was confident about the app's business potential, Stefan quit his job. He worked hard for three months to add a way to accept payments and was thrilled when some free users converted to paying customers. But despite some early success, business growth was slow. Stefan struggled for seven years to find product-market fit. Eventually, in 2019, Stefan had a significant breakthrough. He realized many customers wanted personalized reports. So, he doubled down on that and changed the app's focus to help professional services firms. Today, Pointerpro has surpassed $3 million in annual recurring revenue and has grown to a team of 28 people. The company is still entirely bootstrapped.

From 25-Minute Cold Emails to 7-Figure Founder-Led Sales - Mang-Git Ng

Mang-Git Ng, Anvil

From 25-Minute Cold Emails to 7-Figure Founder-Led Sales

In 2017, Mang-Git Ng was struggling through a painful mortgage application process - exchanging PDF documents over email, filling out the same information repeatedly, sending sensitive data through unsecured channels. That frustration sparked an idea: what if all this paperwork could move online? Mang-Git and his co-founder Ben spent months interviewing people across industries before writing a single line of code. They talked to wealth advisors, insurance agents, and bankers. Eventually they built Anvil, an automation platform that helps product and development teams bring offline paperwork processes online. But finding the right customers proved harder than building the product. Anvil's founders made a classic mistake - trying to sell to anyone and everyone. They attracted demanding customers who expected a turnkey solution for $5 a month, while Anvil was an infrastructure product built for technical teams. Mang-Git spent 25 minutes crafting each cold email and barely got responses. Founder-led sales felt like an uphill battle. The turning point came when they stopped selling to financial services and started targeting organizations with technical DNA - startups, engineering teams, product managers. Their VC firm Gradient connected Mang-Git with a sales mentor who taught him how to unpack customer problems and drive conversations toward a sale. That shift in both audience and founder-led sales approach changed everything. Today, Anvil is a 7-figure ARR SaaS company with a team of 13, having raised $10 million in funding. SEO content marketing and referrals drive the majority of their growth. And Mang-Git developed a clever in-person sales tactic: instead of attending conferences to network with attendees, he buys a ticket and sells to the technical people staffing the booths - a captive audience who can't walk away.

Lost 90% of Revenue Then Made Retention the Growth Engine - Joe Davy

Joe Davy, Banzai

Lost 90% of Revenue Then Made Retention the Growth Engine

Joe Davy is the co-founder and CEO of Banzai, a marketing technology company whose flagship product, Demio, is one of the top-rated webinar platforms for B2B marketing. In 2013, Joe left a senior executive role at Avalara - a company that later sold for $9 billion - to bootstrap a startup from his basement. He and his co-founders spent a year doing rapid prototyping, talking to customers, and testing five different ideas before landing on one that worked: helping field marketers get more people to show up at events. Their outbound sales engine was brutally simple. One email with one question - "Do you need more butts in seats for your events?" - outperformed every polished marketing message they ever tested. That approach took Banzai from zero to seven-figure ARR in about two years, all through cold outreach. Then they raised a Series A in early 2020. Weeks later, COVID hit. Over 90% of their revenue vanished as the field marketing industry collapsed. Unlike conferences and cruise ships, field marketing never recovered - Joe estimates the industry today is about 10% of what it was in 2019. Faced with three options - shut down, hibernate, or pivot - Joe chose the third. Banzai acquired a virtual events company and Demio, a webinar platform built by David Abrams and Wyatt Jozwowski. The acquisitions gave Banzai a product foundation for the future while competitors were raising $25-50 million in venture capital for virtual events and then blowing up. Joe also shares how SaaS retention became the number one metric at Banzai - not growth rate, not new bookings. He explains why net retention rate defines the ceiling for any SaaS business and why founders who ignore it will hit a glass ceiling they cannot break through. Banzai used partnerships with bloggers and marketing automation companies to drive content distribution, let customers serve as the best sales reps through case study content, and applied the Jobs to Be Done framework from Clayton Christensen to guide product development.

5 Years to Find Product-Market Fit Then Revenue Took Off - Alex Yaseen

Alex Yaseen, Parabola

5 Years to Find Product-Market Fit Then Revenue Took Off

Alex Yaseen is the founder and CEO of Parabola, a collaborative data automation tool that helps non-technical teams automate complex, manual data processes. As a strategy consultant, Alex watched Fortune 100 companies pay fresh graduates to do repetitive spreadsheet work that subject matter experts should have been able to handle themselves. He started building Parabola in 2017 to give those operators the power to automate their own workflows without needing engineers. But finding product-market fit took far longer than Alex expected. Parabola launched on Product Hunt and Hacker News, attracted thousands of signups, and generated genuine excitement. The challenge was that most of those early users were hobbyists or one-time problem solvers - people who loved the product aspirationally but did not have a recurring, high-value use case. Alex calls these "false positive" customers. The real turning point came when Alex started studying which customers actually drove revenue. They shared a common trait: they were all trying to use Parabola in the context of a team. They asked for collaboration features like shared components, version control, and the ability to hand off processes when someone left the company. Alex realized he had been building a solo tool when the real opportunity was a team product. When Parabola repositioned around collaboration and started selling to operations teams rather than individuals, the business transformed. Revenue grew rapidly, the company raised a $24 million Series B, and Parabola landed customers like Flexport, Sonos, and Uber Freight. Today, Parabola is a seven-figure ARR business with thousands of teams and about 100 enterprise accounts, having raised over $34 million total. Alex's journey is a masterclass in finding product-market fit by learning to distinguish enthusiastic users from truly valuable ones.

How This AI SaaS Solved the Cold Start Data Problem - Nate Sanders

Nate Sanders, Artifact

How This AI SaaS Solved the Cold Start Data Problem

While working at Pluralsight, Nate Sanders spent 70-85% of his time doing something most product leaders dread - manually synthesizing customer research data across departments. Teams were running thousands of customer interviews a year, but the synthesis was happening in glass conference rooms covered in sticky notes, with 10 people earning $150K+ spending two days on affinity mapping exercises. When the first large language model, BERT, emerged in 2018, Nate ran internal experiments and saw promising results. He and co-founder Trey spent seven months of nights and weekends building prototypes in React, testing half a dozen different product ideas before raising a small angel round from friends and family in the Salt Lake City area. But building an AI SaaS product created a painful chicken-and-egg problem. Artifact needed training data to fine-tune its models, but getting training data required having customers, and customers required a working product. Nate solved this by recruiting nearly a dozen design partners through his network, offering free product access in exchange for their data, feedback, and 30 minutes of weekly time. Each partner signed letters of intent with paid deposits of $1,000 to $1,500 - small enough to vanish on a corporate card, but enough to prove real commitment. With three to four active design partners collaborating weekly, Artifact closed its first $100K in ARR and raised a $5M seed round led by Josh Buckley of Buckley Ventures. But scaling this AI SaaS beyond those initial partners proved harder than expected. The team tried bottoms-up self-service, community building, dinner events in San Francisco, and conferences - spending $30K-$40K on events alone before realizing none of these channels attracted the right buyers. The breakthrough came when Nate discovered that outbound SDR-driven outreach to enterprise accounts produced dramatically better retention, higher ACVs, and stronger engagement than any other channel. Going down-market was tempting because smaller companies moved faster, but enterprise customers had 90% higher ACVs and significantly lower churn. Nate's AI SaaS playbook became clear: double down on a structured SDR-to-AE pipeline with commitment-based sales stages, replacing subjective pipeline assessments with concrete customer actions like sending data source lists and authenticating integrations.

Horizontal Product, Zero Focus, Then 100 Customers in 100 Days - Adam Nathan

Adam Nathan, Almanac

Horizontal Product, Zero Focus, Then 100 Customers in 100 Days

Adam Nathan spent a year testing ideas before landing on Almanac, a collaboration platform for remote teams. He recruited co-founders, raised $9 million in seed funding, and launched a templates gallery that took off during COVID with tens of thousands of new users every month. But the templates gallery was never the real vision. Almanac was supposed to be GitHub for docs - a place where distributed teams could write, approve, and organize their work. The problem was that the product everyone loved was not the product Adam wanted to build. So he made a gutsy call. He shut down the templates growth engine, let go of team members who had been scaling that side of the business, and went back to pre-launch mode. For months, Adam wandered through what he calls a fog - testing SaaS positioning angles, running ads, building landing pages, doing customer interviews - all while trying to project stability and optimism to a team of 20 people who were watching him search for answers. The breakthrough came when Adam narrowed Almanac's SaaS positioning to living documentation for remote teams, with suggest-changes workflows modeled after GitHub. He set a goal of 100 paying customers in 100 days and hit it ahead of schedule. That focus helped Almanac raise its Series A and grow to 7-figure ARR with over 50 employees and $45 million in total funding. Along the way, Adam lost all three of his co-founders - one to disagreements, one to mental health struggles, and one to burnout. He shares how he rebuilt his motivation, why he stopped looking for co-founders and started looking for great startup generalists, and what it takes to keep going when the person you built the company with walks away.

He Waited 10 Years to Launch - Then Grew 400% Year Over Year - Anshu Sharma

Anshu Sharma, Skyflow

He Waited 10 Years to Launch - Then Grew 400% Year Over Year

Anshu Sharma is the co-founder and CEO of Skyflow, a privacy API that acts as a data vault for sensitive customer information like Social Security numbers, credit cards, and health records. Before starting Skyflow, Anshu was a product manager at Salesforce and Oracle, where he spent over a decade watching companies struggle with the same data privacy problems. After 10 years of studying the problem across financial services, healthcare, and consumer tech, Anshu finally launched Skyflow in January 2019. But he took an unconventional SaaS go-to-market approach - he and his co-founder built the product for over 12 months without talking to a single customer. For a category-creating company like Skyflow, there was no MVP shortcut. The minimum viable product for a new data infrastructure layer had to be robust enough that a CTO could see why it was fundamentally different. The bet paid off. Skyflow's very first customer call ended in a sale. A former CTO of Goldman Sachs told Anshu it was the easiest buying decision of his career. Within a few years, Skyflow crossed seven-figure ARR, grew 400% year over year, hired 105 people, and raised $70 million through Series B. The SaaS go-to-market strategy that drove Skyflow past 100 customers was thought leadership content that educated the market from first principles - explaining why a data privacy vault needed to exist, rather than pitching features. Anshu also shares the story of a major customer who tried to cancel after a leadership change, and how turning that relationship around led to an even bigger deal years later.

How Sitting in Back Offices Built a Vertical SaaS - Sufian Chowdhury

Sufian Chowdhury, Kinetik

How Sitting in Back Offices Built a Vertical SaaS

Sufian Chowdhury is the co-founder and CEO of Kinetik, a company that's built the first integrated software for non-emergency medical transportation. Back in 2016, while working on a different startup idea, an old buddy of his, who was running a transportation business, came to Sufian in a panic about a database problem, which was really just a huge out-of-control Excel spreadsheet. While trying to fix the 'database' problems, Sufian discovered a whole bunch of problems with the actual transportation business that was helping Medicaid patients get to their medical appointments. Growing up in a low-income family that relied on Medicaid, Sufian felt an instant need to jump in and solve these problems with his friend's business. Together with a couple of other friends (who later became his co-founders), they started hanging out in the back office of the transportation business. They wanted to get a handle on how the business worked and wondered if they could develop software to replace the Excel spreadsheet. In time, they figured they'd also be able to help other businesses dealing with the same issues. But, 6 months later, they realized they'd built the wrong software. Worse still, Sufian had already burnt through $80,000 of his own money on this venture. So, they had to hit reset and start from scratch on the product. But this time they decided to talk to folks in transportation companies, ensuring they got what was needed and could build the right thing. Fast forward 18 months, and they finally launched their product and started getting paying customers. Things were looking up. But then, the pandemic hit and they lost a whopping 70% of their customers. Instead of giving up, Sufian decided to double down on the software business with an even bigger and bolder vision of what they were going to do.

5 Lessons on Finding Product-Market Fit and Scaling - Jeremy King

Jeremy King, Attest

5 Lessons on Finding Product-Market Fit and Scaling

Over the past 10 years, Omer Khan has interviewed more than 350 SaaS founders on The SaaS Podcast. This episode distills five of the most valuable clips from recent conversations into a single masterclass for early-stage founders. First, Jeremy King reveals how he took Attest from zero to $1M ARR in under eight months by physically interviewing 200 consumers at Waterloo Station before writing a single line of code. His approach to finding product-market fit started with proving demand at the ground level rather than guessing from a spreadsheet. Next, Melissa Kwan explains why she spent over two years building eWebinar before showing it to anyone. Having done more than 1,000 webinars during her previous startup Spatio, she knew exactly what the product needed to be and refused to ship until the last 2% was right. The result: 750K ARR and 700 customers, entirely bootstrapped. Christian Owens, who started building websites at age 12 and now runs Paddle at nearly $100M ARR, shares his framework for finding product-market fit through pragmatism. Every business he has built - from invoicing software to a $1M software bundle to Paddle itself - made money from day one. Trevor Kaufman's story is a gut-check for any founder facing market rejection. He sold his own house to keep Piano alive after media companies refused to adopt paywalls. Today Piano serves 800 customers at $80M ARR, proving that being early to a market is not the same as being wrong. Finally, Rahul Vora walks through the Product Market Fit Engine he created at Superhuman. After two years of coding with intense pressure to launch, Rahul developed a four-step system - survey, segment, analyze, implement - anchored on Sean Ellis's "very disappointed" benchmark of 40%. That framework helped Superhuman find product-market fit systematically and raise over $125M. Whether you are validating a new idea or wondering if your current product has real traction, these five stories offer a practical playbook for finding product-market fit and building a business that lasts.

70% Close Rate: The 4-Step SaaS Onboarding Call Framework - John Li

John Li, Vimcal

70% Close Rate: The 4-Step SaaS Onboarding Call Framework

In 2017, John Li and his co-founder Michael got accepted into Y Combinator with an augmented reality idea. The market was not ready. They pivoted to a fitness app. That did not get traction either. After two years and two failed products, they had eight months of runway left. In 2019, they bet everything on their third idea: Vimcal, a calendar app designed to be the fastest scheduling tool for busy founders, VCs, and remote teams. But building a calendar app proved harder than expected, and by launch day they had just 1.5 months of cash remaining. They had already prepared legal documents to shut down the company. John's survival tactic was SaaS onboarding calls. He got on a 30-minute Zoom with every single user, perfected a demo script, and asked for a $15 subscription at the end of each call. His close rate hit 70%. When users matched the qualifying profile of using Calendly, Google Calendar, and Superhuman, the close rate jumped to over 90%. One of those SaaS onboarding calls changed everything. A user offered to write a $5,000 investment check instead of paying $15. More checks followed. John used the calls as both a conversion tool and a fundraising vehicle during the early months of COVID, when no one else was writing checks. John also built a waitlist with a Typeform that acted as a qualifying filter. Of tens of thousands of signups, Vimcal only let in about 20%. The first question asked whether the user felt overwhelmed by meetings, and 92% said yes. Qualifying questions about which apps they used and how many external meetings they had determined who got access. The company later stumbled when it dropped both the waitlist and the onboarding calls on the same day. Growth slowed for six to eight months until they rebuilt momentum by shipping every two weeks, landing a TechCrunch feature, and reintroducing onboarding call prompts in the self-serve flow. Today, Vimcal is a nine-person team that has raised $2.4M and is targeting $1.5M ARR with profitability in sight. John also launched Vimcal Maestro, the first calendar built specifically for executive assistants.

100 Interviews Before Code: Finding Product-Market Fit - Brandon Foo

Brandon Foo, Paragon

100 Interviews Before Code: Finding Product-Market Fit

Brandon Foo is a second-time founder who learned the hard way that building a great product means nothing if nobody needs it badly enough to pay. His first startup, Polymail, was an email productivity app that attracted tens of thousands of users but never found a large enough market to sustain growth. That experience taught Brandon a critical lesson about finding product-market fit: stop building and start selling. When Brandon and his co-founder Ishmael started Paragon, they flipped the playbook. Instead of spending months writing code, they ran over 100 customer interviews, showed mockups and prototypes, and asked prospects to enter their credit cards on a Stripe form for a product that barely existed. They started at $30 per month and gradually raised prices to test the ceiling of customer willingness to pay. That iterative approach to finding product-market fit led them through several pivots. Paragon started as a backend-as-a-service (similar to Firebase), but customer conversations kept pointing to one consistent pain point: building and maintaining SaaS integrations. Brandon and Ishmael followed the signal, refined the product, and eventually built an embedded integration platform that helps software companies connect with tools like Salesforce, Slack, and HubSpot. Today, Paragon serves over 100 customers, supports 90+ integrations out of the box, and has grown to several million dollars in ARR with a team of 30+. They raised $16 million in venture funding, including a $13 million Series A led by Inspired Capital. Brandon also shares how LinkedIn ads became Paragon's most successful growth channel, and the delegation challenges he faces scaling from a founder-led company to a team-driven organization.

Competing with DocuSign by Being 10x Easier to Use - Sunil Patro

Sunil Patro, Signeasy

Competing with DocuSign by Being 10x Easier to Use

Sunil Patro is the founder and CEO of Signeasy, a user-friendly electronic signature and contract workflow platform to sign, send, and manage agreements. In 2009, Sunil was traveling in Mexico and waiting for a new job offer. Faced with the challenge of signing the offer without easy access to a printer, he wondered how much simpler it would be if he could sign the document on his smartphone. This lightbulb moment kicked off Sunil's journey to create Signeasy. With a background in software development, Sunil spent six months researching the idea before launching Signeasy as a mobile app. Within the first year, the app generated around $10K a month. This early success motivated Sunil to keep pushing forward with the product, ultimately hitting the milestone of $1 million in annual revenue. But after five years of concentrating on the mobile app market, Sunil recognized an opportunity for growth and decided to pivot Signeasy towards a B2B SaaS product. The competitive differentiation that made SignEasy stand out on mobile - simplicity and ease of use - became the foundation of its B2B strategy. Despite facing fierce competition from well-funded competitors like DocuSign and Adobe Sign, Signeasy managed to carve out its niche by emphasizing simplicity, affordability, and great customer support. Sunil's competitive differentiation approach proved that you don't need to out-feature incumbents when you can out-simplify them. Today, Signeasy is a thriving SaaS company with millions in ARR, closing in on becoming an eight-figure business. With over 50,000 customers worldwide and a team of 80 employees, Sunil's initial vision has come a long way.

How Grain Found Product-Market Fit After Throwing Away a Year of Code - Mike Adams

Mike Adams, Grain

How Grain Found Product-Market Fit After Throwing Away a Year of Code

Mike Adams is the co-founder and CEO of Grain, a tool that records, transcribes, and uses AI to turn unstructured video meetings into shareable highlights. Before Grain, Mike co-founded Degreed and MissionU (acquired by WeWork), making this his third startup. In 2018, Mike and his brother Jake started building Grain with an insight from MissionU: every conversation happening over video was data that shouldn't be lost. But they made a classic mistake - they started with a solution and went looking for a problem to solve. Their first year was a grind. They had no clear ideal customer profile. Mike joked that their ICP was "anyone who would talk to us and thought it was cool." They showed the product to friends who told them it was great but couldn't give them the clarity they needed to build a real business. The turning point came when they ran a more rigorous customer research process. They brought people into their office, pretended the product was built by someone else, and asked for brutally honest feedback. That process revealed one feature that stood out above everything else: the ability to clip a 30-second moment from a Zoom call and share it anywhere. They threw away their entire codebase and rebuilt Grain around that single insight. Finding product-market fit was still far from over. When COVID hit, an investor pushed them to launch publicly. Mike's instincts said to stay in beta, but he went against his gut. Within a month, seven or eight YC companies launched near-identical products - some had been in Grain's own beta. The competition was fierce, but it validated they'd built something real. Grain grew to $1M ARR, 1,300 customers (including Slack, Zapier, and Webflow), and raised $21M total. Along the way, Mike learned hard lessons about finding product-market fit: that qualitative customer interviews reveal truths that gut feelings miss, that the entry point into organizations was through sales teams (not product teams as he'd assumed), and that trusting your instincts as a CEO matters more than following advisors with the wrong playbook.

29x ARR Growth Started When the CEO Sold the Product Himself - Mathew Cagney

Mathew Cagney, Renewtrak

29x ARR Growth Started When the CEO Sold the Product Himself

Mathew Cagney became CEO of Renewtrak in 2020, taking over a startup that had been founded six years earlier but had failed to get any real traction. The original founders had built a beta solution, secured initial funding, and managed to get two small customers. But things had stalled. When Mathew joined, the company had a high churn rate, no new customers coming in, and was quickly burning through its cash. The engineering team was spending 95% of its time putting out fires across six separate code bases. The sales team and third-party channels were unable to convert a single new deal. Mathew believed that founder-led sales was the only path forward. He fired the third-party sales channels, shut down the overseas call center, and made a personal commitment: if he could not sell the product himself, he would not hire anyone else to do it. He spent 60% of his time outside of capital raising on cold outreach, LinkedIn prospecting, and closing deals personally. That bet on founder-led sales paid off. Within six months, Mathew and his team landed Lenovo as a customer. In parallel, he brought in a trusted CTO to rebuild the data ingestion engine and consolidate six code bases into one. To bridge the gap while the product was being rebuilt, Renewtrak over-invested in customer success, meeting customers two to three times per week and providing actionable intelligence reports that proved the platform's value. The pricing model also had to change. An initial transaction-only model was not generating enough cash flow, so the team pivoted to a subscription plus success fee structure with quarterly advance billing. That shift alone stabilized the company's finances. Today, Renewtrak is doing around $6 million in ARR with customers including VMware, Lenovo, HP, and Cisco. The company went from 6-8 story points per sprint to over 100, and from burning cash to expanding existing accounts as its primary growth engine.

From 22% to 58% - Finding Product-Market Fit With Data - Rahul Vohra

Rahul Vohra, Superhuman

From 22% to 58% - Finding Product-Market Fit With Data

Rahul Vohra is the founder and CEO of Superhuman, a blazingly fast email experience that helps you save 3 hours or more every week. In 2014, Rahul set out on a mission to create the fastest email experience. He had sold his previous company Rapportive, a Gmail plugin, to LinkedIn a couple of years earlier, and he'd watched as Gmail continued to become slower and more cluttered over the years. So Rahul decided it was time to change that. But he didn't start building a product right away. Instead, he spent the first year talking to potential customers, doing interviews, writing website copy, and talking to investors. A year later, he put together a team and started building the product. But progress was slow. After two years of coding, the product still wasn't ready. Rahul felt immense pressure to launch. But deep down, he believed the launch would go badly because they didn't have product market fit. Fast forward to today, Superhuman has raised over $125 million in VC funding and is now a team of around 120 people.

100 Customer Interviews Before Writing a Line of Code - Gil Feig

Gil Feig, Merge

100 Customer Interviews Before Writing a Line of Code

Gil Feig is the co-founder of Merge, a unified API platform that allows you to add hundreds of integrations to your app. After experiencing firsthand the pains of managing integrations at previous companies, Gil and his co-founder, Shensi, decided to build a solution. Before starting their business, they talked to around a hundred companies to research and get feedback. Most conversations were pretty positive, but some feedback was harsh. There were three companies where people told them they would never use the product and that they should probably give up on the idea. The two founders spent 6 months building the first version of the product. And thanks to all those interviews, they landed their first 10 customers. But as they tried selling their product to more companies, they quickly realized that they still had big obstacles to overcome. Most companies were building their own integrations, and many of them weren't convinced they needed help or a product to make it easier. And other companies weren't willing to trust their integrations to an early-stage startup that might not be around tomorrow. Despite those challenges, Gil and Shensi have grown their business to multiple 7-figures in ARR, with a team of around 65 people, and they've raised almost $75 million in funding.

Wrong Target Market for a Year Then SaaS Positioning Clicked - Geoff Roberts

Geoff Roberts, Outseta

Wrong Target Market for a Year Then SaaS Positioning Clicked

In 2016, Geoff Roberts and his co-founder Dmitry set out to build Outseta - an all-in-one platform for subscription businesses that includes billing, CRM, email, and help desk. The idea came from their experience at Buildium, where Dmitry had spent 25% of his time as CTO stitching together third-party tools instead of building product. They figured other founders had the same problem. It took two years of part-time work to ship the MVP. But when they started selling, developers - their original target customers - kept shrugging. Most preferred assembling their own tech stacks. The team struggled for almost a year with minimal traction. Then something shifted. No-code founders building on Webflow started discovering Outseta. For these less technical builders, the all-in-one SaaS positioning was far more valuable than it had been for developers who could wire up their own tools. The team doubled down on this new audience, and growth took off. Today Outseta has roughly 6,000 companies on the platform and is approaching $1M in revenue with just five full-time employees. Their customer base is now split evenly between no-code founders and developers - because as the product matured, developers came back too. The SaaS positioning lesson is clear: the same product can fail or succeed depending on which audience you put it in front of. Along the way, Geoff and his team made some bold choices. They killed their freemium plan after thousands of free users overwhelmed their five-person support team. They built partnerships with Stripe and Webflow that became their second and third biggest lead sources. And they adopted a self-managed structure with a standardized $210,000 salary and a flexible equity-or-cash compensation model.

How a Tech Founder Used Founder-Led Sales to Hit $1M ARR - Hung Dang

Hung Dang, Y42

How a Tech Founder Used Founder-Led Sales to Hit $1M ARR

Hung Dang is the founder and CEO of Y42, a fully managed DataOps cloud that helps companies design production-ready data pipelines on top of their Google BigQuery or Snowflake data warehouse. After years working in data analytics and running an event analytics company that was acquired by a German Fortune 100 company, Hung became frustrated with the five-plus tools needed to build a proper data infrastructure. In 2020, he decided to build an end-to-end data platform to replace them all. But Hung didn't interview customers to validate his idea. He hired a team of engineers and spent a full year building the product in silence. When he finally put it in front of customers, he discovered it was missing about 30% of the features they needed, and about 20% of what he built was not important to them. Despite that rocky start, Hung used founder-led sales to close Y42's first customers through angel investor networks and vision selling. The company hit $1M ARR within a year of launching. Hung talks about how his early experience doing door-to-door donations for the Red Cross taught him resilience and sales fundamentals that carried over into founder-led sales as a tech CEO. Y42 has since raised $34 million in funding, grown to 150 employees, and serves hundreds of customers across e-commerce, retail, and B2B SaaS. Hung shares the lessons he learned about balancing product building with customer conversations, why hiring senior sales and marketing leaders took over 10 months, and how thought leadership on LinkedIn became a key growth channel for a data infrastructure company.

Sold His House to Fund a Vertical SaaS Nobody Wanted - Trevor Kaufman

Trevor Kaufman, Piano

Sold His House to Fund a Vertical SaaS Nobody Wanted

Trevor Kaufman had already built and sold a digital agency to WPP when he discovered a two-person startup called TinyPass in a small room above a restaurant in Tribeca. He started seed financing the business and eventually left WPP to become CEO in 2012. TinyPass was building a micropayment solution for digital content creators. But 18 months in, Trevor ran the numbers and realized the economics of taking a percentage of small transactions would never work. Even a million subscribers paying $50 a year would only generate a $5 million business at a 10% take rate. It was not a viable business model. So they pivoted to selling vertical SaaS software directly to large media companies. But the timing was brutal. Most publishers believed advertising would sustain their business. "Information wants to be free" was the dominant mindset, and out of every 100 meetings, only two companies showed any interest. Trevor was paying payroll out of his own pocket. He had money from selling his agency, but that ran out and he ended up selling his house to keep the business going. He kept pushing because he believed media companies would eventually have to charge for content. He just had to outlast the market's resistance. In 2015, TinyPass merged with a European competitor called Piano Media. The combined vertical SaaS company had about 45 employees and $5-6 million in revenue. From there, Piano grew by going deeper into the publishing vertical rather than expanding across industries. Customers kept asking for more - recurring billing, rules engines, login systems, analytics - and Piano built each piece, replacing 8-15 vendors with one platform. Piano also made four strategic acquisitions, including a public-to-private deal in Norway that brought real-time segmentation technology and a team in Japan. Today Piano serves 800 customers worldwide, generates $80 million in ARR, has over 620 employees, and has raised $222 million.

Enterprise Sales From a Basement With No Category - Doug Winter

Doug Winter, Seismic

Enterprise Sales From a Basement With No Category

Doug Winter is the co-founder and CEO of Seismic, a sales enablement platform that helps organizations better engage with customers and grow revenue. In 2010, Doug and his co-founders launched the business out of a basement in San Diego. Their previous company had been acquired by EMC, and they saw an opportunity to bring the SaaS model to content management the same way Salesforce had done for CRM. They initially focused on sales and marketing teams, but there was a problem. Sales enablement did not exist as a product category. For the first two years, they struggled to position the product. Enterprise buyers kept asking where Seismic fit on the analyst block diagrams, and the founders kept debating what to call themselves. Rather than starting small and working their way upmarket, they went after enterprise sales from day one. Doug says the reason was simple: that was their comfort zone. They knew how to sell to large financial services companies and manufacturers, and they did the math on how many $10K deals it takes to reach $1M ARR. But selling enterprise as an unknown startup brought serious obstacles. Compliance teams flagged them as a bankruptcy risk. Security checklists arrived with 47 tabs and hundreds of questions they could not answer. And on one memorable leap day in February, a cloud provider bug destroyed a critical executive demo just hours before they lost their biggest pipeline deal. Doug explains how they survived those early setbacks, how they turned small pilot deals into million-dollar contracts by adjusting their roadmap without building custom features, and why being an "emotional counterbalance" became the most important part of his job as the company scaled to $300M in enterprise sales revenue.

Why Targeting 3 Verticals Nearly Killed This Vertical SaaS - Stefan Laven

Stefan Laven, Data Talks

Why Targeting 3 Verticals Nearly Killed This Vertical SaaS

Stefan Laven is the founder and CEO of Data Talks, a customer data platform (CDP) that helps sports organizations create world-class supporter experiences based on their data. In 2018, Stefan was running a consultancy and helping clients turn their data into insights. But he realized that many clients struggled to figure out what to do with those insights. So he and his team decided to build a product to help their clients get more value from those insights. They built an MVP and started showing it to their clients. And it didn't take them long to signup their first 10 customers. Most founders would be delighted by that, and Stefan was too. But today, he looks back and wishes that they hadn't sold their MVP so quickly, and we talk about why and what he would have done differently. Also, when they launched, they hedged their bets and decided to go after three different vertical markets at the same time instead of picking one vertical. That approach didn't work, and they wasted a ton of time and money. Eventually, they decided to focus on just one vertical. And that's when everything clicked, and the business grew faster. We talk about why it's so difficult to commit to one market and how Stefan and his team got there. Currently, Data Talks has about 500 customers and is generating around $250K in monthly recurring revenue. I hope you enjoy it.

She Gave Her SaaS Away Free for 18 Months. Here's What Changed. - Cristina Vila

Cristina Vila, Cledara

She Gave Her SaaS Away Free for 18 Months. Here's What Changed.

Cristina Vila is the co-founder and CEO of Cledara, a product that helps companies simplify the way they discover, buy, manage and cancel subscription software. In 2018, Cristina quit her job to start her SaaS business. She was a first-time founder, who didn't know how to code and didn't have any sales experience. But she was driven by a life-long dream to one day start her own business. After raising a pre-seed round, she hired a software development company to build the product which she launched at SaaStock in Dublin three months later. But when she tried to sell her product, she got a lot of objections. Some people said that they didn't have a problem managing software subscriptions, others felt they already had a good solution in place (even if it was just a spreadsheet), and a lot of other people just weren't interested at that time. So for a while, things weren't looking good for Cristina. And even worse, she didn't charge for her product for 18 months. In fact, there wasn't even a way for customers to pay for her product - which many would say was a rookie mistake. Despite those challenges, Cristina and her co-founder Brad, have grown Cledara to $2.4M in ARR so far with over 700 customers. And they've raised $7M and built a team of nearly 50 people.

6 Months Without Code Then Enterprise Sales Changed Everything - Thor Olof Philogene

Thor Olof Philogene, Stravito

6 Months Without Code Then Enterprise Sales Changed Everything

Thor Olof Philogene is the co-founder and CEO of Stravito, a knowledge management platform that helps global organizations centralize and search their market research. Stravito was founded in Sweden in 2017, has raised $23 million, and counts Fortune 2000 companies like Comcast, Electrolux, and McDonald's as customers. Before starting Stravito, Thor served as VP Growth and Chief Revenue Officer at iZettle, where he saw firsthand how enterprises struggle to distribute knowledge at scale. That experience, combined with his co-founders' 15 years running a market research agency, gave them deep insight into a $90 billion market that most people have never heard of. In this conversation, Thor walks through how Stravito validated the problem by interviewing 10 enterprise companies before writing a single line of code. He explains why they charged for their MVP from day one through paid proof-of-concepts, and how they survived five months of biweekly checkpoints where they could have been eliminated at any point. Thor also shares how enterprise sales worked in the early days - why founders must lead the sales process, how to overcome the "you're too small" objection by targeting early adopters, and how sub-segment-specific campaigns helped them break into FMCG companies before expanding. He also covers the expensive lesson of trying to scale into new segments before achieving product-market fit in each one.

10 Failed Products Then Finally Finding Product-Market Fit - Jeb Banner

Jeb Banner, Boardable

10 Failed Products Then Finally Finding Product-Market Fit

Jeb Banner is the co-founder and CEO of Boardable, a board management SaaS product that centralizes communication, document storage, meeting planning, and everything involved with running a board of directors. In 2016, Jeb was running a creative agency called Smallbox when a client, United Way of Central Indiana, asked if he could build a board management portal. His team scoped it out, but the cost was too high for the client. Jeb had already started two nonprofits at that point, so he understood the pain of managing boards with email, attachments, and doodle polls. He and his co-founders decided to build the solution themselves. They built an MVP in six weeks, tested it with six or seven local nonprofits, got feedback, and completely rebuilt it from scratch. By January 2017 they had their first paying customers. The early traction came through paid directories like Capterra, which brought in self-service signups from 40 countries. But finding product-market fit with Boardable was not Jeb's first attempt at building a product. He and his technical co-founder Joe had built close to 10 products over 12 years, including a to-do list, a CMS, a content gathering tool, a digital leave-behind, and an employee engagement tool. None of them got traction. The pattern only broke when they separated the product business from the agency into its own entity with its own payroll. Jeb also shares how Boardable started as a product-led growth company but eventually realized the buyer was not the user, forcing a pivot to sales-assisted growth. He explains how hiring a data scientist in the early stages helped them score leads and uncover behavioral signals, like deleting an agenda item, that predicted conversion. And he talks about why finding product-market fit in the nonprofit niche first gave Boardable a complexity advantage that now wins enterprise deals.

3 Years of Zero Traction Then Finding Product-Market Fit - Khadim Batti

Khadim Batti, Whatfix

3 Years of Zero Traction Then Finding Product-Market Fit

Khadim Batti is the co-founder and CEO of Whatfix, a Digital Adoption Platform (DAP) that helps businesses simplify training and support. In 2014, Khadim and his co-founder Vara launched a new SaaS business called Whatfix. In 8 years, they've grown their company to multiple 8-figures in ARR, hired over 600 employees, and they've raised $140 million in VC funding. It sounds like another great Silicon Valley startup story, but it isn't. Both these founders were based in India. Prior to founding Whatfix, they spent 3 years building another product that never really got traction. Both founders came from an engineering background, so they spent too much time trying to build a great product and not enough time talking to customers. During those 3 years, there were many times when they wanted to quit and go back to their corporate jobs. At one point, they realized that there was one feature in their product that their customers seemed to be most interested in. In fact, it wasn't even a product feature, but a tool they'd built to help their customers learn how to use their product. So they decided to shut down the product they'd been working on for 3 years and instead focus on turning that tool into a product. But this time they took a very different approach. They spent most of their time talking to customers and validating their idea. And they didn't start building the product until they'd made their first sale. In this interview, Khadim shares his lessons on the mistakes they made in building their first product. And we dig into how they took a very different approach the second time with Whatfix, and how they've gone from zero to a company valued at over $600 million. I hope you enjoy it.

5 Customer Interview Tactics for Finding Product-Market Fit - Michele Hansen

Michele Hansen, Geocodio

5 Customer Interview Tactics for Finding Product-Market Fit

Michele Hansen is the co-founder of Geocodio, a geocoding SaaS she built with her husband over eight years, and the author of Deploy Empathy, a practical guide to interviewing customers. Before running Geocodio full time, Michele was a product manager focused on customer research. After becoming an investor in Earnest Capital (now Calm Fund), she spent years coaching portfolio founders on how to use customer interviews to understand their markets. That experience led her to write Deploy Empathy - a guide designed specifically for founders without UX or product backgrounds. In this conversation, Michele and Omer work through a hypothetical scenario of a B2B founder who has built a product but can't close deals. Together they explore how to find and recruit interview subjects on LinkedIn, what questions to ask, how to build rapport so people open up, and why the real insights come after the "reaching for the door" question - the moment you pretend the interview is over and ask "Is there anything else you think I should know?" Michele also explains how Deploy Empathy builds on Rob Fitzpatrick's The Mom Test by going beyond the discovery phase into finding product-market fit, reducing churn, and figuring out which features to build. If you've ever struggled with customer interviews or wondered why prospects aren't converting, this conversation gives you a practical playbook for finding product-market fit through genuine listening.

From Agency Spreadsheets to $1M ARR With Founder-Led Sales - Mitch Causey

Mitch Causey, DemandWell

From Agency Spreadsheets to $1M ARR With Founder-Led Sales

Mitch Causey is the co-founder and CEO of Demandwell, a SaaS company that provides software and coaching to help B2B SaaS marketers turn organic search into a source of repeatable revenue. When Mitch launched Demandwell, it was just a one-person SEO agency. Mitch worked with one client at a time. His main tool was a spreadsheet that he'd create for each client and use to help them improve their organic search traffic. But he quickly realized that this business couldn't scale. And building a software product to replace his spreadsheets seemed like the next logical step to enable Mitch to help more clients. In about 18 months since launching his SaaS product, Mitch has been able to turn Demandwell into a 7-figure business with a team of 16 people. One big reason why he's been able to grow so quickly is that he first spent 18 months providing a service and helping clients manually. He effectively built an MVP without any software - a concept known as a Concierge MVP. It's an approach that can work for a lot of different types of startups. Many founders get stuck figuring out how to build an MVP. And the truth is that your MVP does not have to be software. Your MVP can be a service instead. Your Concierge MVP can help you quickly validate your idea, find customers, learn more about your target market, start generating revenue quickly, and even pre-sell your SaaS product to some of those customers to help fund development. I hope you enjoy the interview.

How Niche SaaS Focus Turns One Market Into Many - Dave MacLeod

Dave MacLeod, ThoughtExchange

How Niche SaaS Focus Turns One Market Into Many

Dave MacLeod is the co-founder and CEO of ThoughtExchange, an enterprise tool that helps leaders quickly gain critical insights and make better decisions. In just over 10 years, Dave and his co-founder Jim have grown ThoughtExchange into a $20M annual business with 200 employees and $45M in funding. But there was a time when no one was interested in buying their product. They built the product first and then tried to find people who had a problem that they could solve. It was not a smart way to go about building a business. So it was hardly surprising that they struggled to find customers. They kept hearing the same feedback - it is an interesting idea, but it is not a product we would ever use in our organization. But eventually, they did find a customer in an unlikely place. It turned out that a school superintendent had the exact problem their product could solve. And at that point, the founders made a very smart decision. Although they did not fully realize it at the time, they decided to go all in and focus on school districts. For almost five years, they focused almost exclusively on that one niche SaaS market instead of going out and trying to sell their product to everyone. Today, half their business comes from enterprise customers. But their success was originally built by focusing on one target market and one customer for years. Whether you are trying to find your first 10 customers or get to your first hundred million dollars in ARR, niche SaaS focus is just as critical. And that is what we dig deeper into in this interview.

From Teen Side Project to SaaS Fundraising Win - Liam Gerada

Liam Gerada, Krepling

From Teen Side Project to SaaS Fundraising Win

Liam Gerada is the co-founder and CEO of Krepling, an e-commerce platform for online stores. In 2018, two teenage brothers in Malta wanted to start an agency. They had recently sold their Shopify store and decided that they wanted to help others running similar businesses. They spent a few months validating the idea but realized people did not need an agency - they needed a better platform. So Liam and Travis set out to build a Shopify competitor. Neither of them was a developer, but Travis had taken some courses so he knew just enough to start building something. After months of work, they shipped a product with a clunky backend and an ugly user interface. But the product was free and they were still able to attract new users. But as soon as they started charging, every user they had churned. The brothers pushed on and tried anything they could think of to find customers - posting on sites like Quora and Reddit, sending cold emails. Eventually, they were able to find a handful of customers. Fast forward to today. Liam is now 21 and Travis is 18. The two brothers have made significant improvements to their product. They now have over 500 customers and they have raised a pre-seed round from Jason Calacanis' LAUNCH accelerator. They still have a long way to go and a lot more work to do, but they have accomplished a lot in the last couple of years. They are both still pretty young, did not have tons of experience, did not know how to code, and live on a small island in the middle of the Mediterranean. But that has not stopped them from building their SaaS business and securing SaaS fundraising to take Krepling to the next level.

SaaS Product-Market Fit: Stop Selling and Start Building - George Carollo

George Carollo, Dover

SaaS Product-Market Fit: Stop Selling and Start Building

George Carollo is the co-founder of Dover, an end-to-end recruiting automation platform that helps companies to find and hire top talent. Dover uses advanced matching software to identify the perfect candidates across all recruiting channels and drives the hiring process for companies and candidates. In 2019, three friends teamed up to launch a new SaaS startup. They'd all felt the pain of recruiting in previous companies and decided to solve that problem. They got their first 10 customers without a product or website. In fact, at that point, they didn't even have a company or product name. For the first 9 months, they solved the problem manually for customers. The team would review resumes, create a shortlist of candidates and then connect the right candidates with the right companies. By taking this approach, the founders were able to better understand customers and identify exactly the right problem to solve with software. But growing beyond their initial customers was tough. They sent about 1,000 cold emails to recruiters which turned out to be a waste of time. They hired writers to create content, but they couldn't find anyone who understood the problem, market, and data well enough to create meaningful or useful content. Nothing seemed to be working. And then COVID hit and suddenly things looked even worse. Not only were they unable to acquire customers, but they were also now struggling to keep the ones they had. The founders then made an important but risky decision. They decided to stop selling and instead focus all their time on building a better product. In this interview, we explore why they made that decision and how they turned things around to get the business to $4M in annual recurring revenue (ARR).

Hard Lessons on Finding SaaS Product-Market Fit - Rohith Salim

Rohith Salim, SpotDraft

Hard Lessons on Finding SaaS Product-Market Fit

Rohith Salim is the co-founder and Chief Product Officer of SpotDraft, a product that helps companies create, manage and review legal contracts. In 2017, SpotDraft's three founders teamed up to launch their new startup. They saw an opportunity to streamline the end-to-end contract management process and believed they could solve that problem. Initially, they built a product for freelancers and solopreneurs. But they quickly realized that most people in that market weren't willing to pay for a solution. So they decided to move upmarket and target Fortune 500 companies. But they didn't have the experience or credibility to win customers. Eventually, they struck a deal with a large reseller through which they got their first couple of customers. On paper, things were looking pretty good for them, and they were able to project out several million dollars in revenue from this one channel. But working with a reseller also created several new issues for the founders. They found themselves doing custom development work for each customer, which led to a higher onboarding and support overhead. But worst of all, they didn't own any direct relationships with customers - they were effectively a subcontractor. It took the founders a long time to understand a fundamental lesson - as a SaaS business, you can't channel partner your way to product-market fit. Eventually, the founders had to go back to the drawing board, do a bunch of customer interviews and try to figure out a completely new plan.

The SaaS Sales Strategy Foundation Most Founders Skip - Pete Kazanjy

Pete Kazanjy, Atrium

The SaaS Sales Strategy Foundation Most Founders Skip

Pete Kazanjy is the co-founder of Atrium, a sales management tool that uses data and smart analytics to help sales leaders and managers improve team performance. Pete is also the author of Founding Sales, the early-stage go-to-market handbook for founders and other first-time sellers. In this episode, we talk about how to craft a sales narrative for your SaaS product. Before you can scale your sales process, you need to ensure that there's consistency in your messaging throughout your organization. You don't want your marketing and sales teams communicating different messaging to your prospects and customers. And you certainly don't want sales reps pitching to a prospect when they don't understand how to deliver the right message in the right way. A sales narrative is critical to helping everyone in your company understand the product that you're selling and how to tell its story to your prospects and customers. Once you've crafted that narrative, you can eventually use it to create your sales decks, email templates, website copy, videos, advertising, and so on. So your sales narrative is a critical foundation for your sales process. But most companies don't understand how to tell a story about their product. In this episode, we share a framework to help you develop the key elements of your sales story and put it all together into a cohesive narrative that helps you close more deals.

How GoGuardian Reached 18M Students With Vertical SaaS - Advait Shinde

Advait Shinde, GoGuardian

How GoGuardian Reached 18M Students With Vertical SaaS

Advait Shinde is the co-founder and CEO of GoGuardian, a suite of products that provide K-12 schools with content filtering and monitoring, classroom management software, and a suicide prevention tool. In 2014, Advait and his two co-founders built a Chrome extension to help schools with web filtering. But it seemed that no one was interested in their solution and their outreach emails didn't get much of a response either. They were almost ready to give up on their idea. Luckily, one of the co-founders wasn't ready to give up just yet and kept contacting people despite the lack of interest and rejections. Thanks to his persistence they found some early users which helped to start collecting valuable feedback from their target market. Later, when the founders tried to raise money, they were rejected by investors. They were told that they were too young and inexperienced. And investors warned them that the K-12 market didn't have money and that focusing on Chromebooks was completely the wrong strategy. Fortunately, the founders didn't listen. Today, GoGuardian is used by 18 million students, which is about a third of all K-12 students in the US. The company now employs over 300 people and generates north of $50M in annual recurring revenue (ARR).

He Cut SaaS Churn 50% Without a Silver Bullet - Daniel Scrivner

Daniel Scrivner, Flow

He Cut SaaS Churn 50% Without a Silver Bullet

Daniel Scrivner is the CEO of Flow, a task and project management product that's used by over 300,000 teams. In early 2019, Daniel was hired to help lead the turnaround at Flow. The company was about 10 years old and in trouble. It was losing customers and revenue at a worrying rate. The team had been spending about $100,000 a month on paid acquisition advertising but it wasn't moving the needle. In fact, revenue was still declining by about 5% month over month. When Daniel joined, continuing to spend any money on acquisition wasn't an option. So with a core team of 6 people, he had to figure out how to lead a turnaround - and do it fast. It was a huge challenge. But Daniel had to deal with one more - this was his first job as a CEO. In this interview, we talk about why an unlikely candidate like Daniel was hired as CEO and how he and his team went about diagnosing and fixing some major problems. We dig into why and how he rehauled the Flow product by improving the design, making it more modern and lightweight, and reducing friction for end-users. And we explore how the team went about fixing their marketing and sales funnel so they were able to improve how they acquired, activated, and retained customers. Today, Flow is growing again. And Daniel's role has evolved from a turnaround to growth CEO. Whether you're working on a SaaS business that's not growing fast enough or one where revenue is in decline, there are a lot of great lessons in this interview. We often look for silver bullets to solve seemingly insurmountable problems. But this story is a reminder about the importance of nailing the fundamentals, constantly improving small things, and eventually seeing them compound into meaningful results for your business.

How Unstack Used Competitive Differentiation in a Crowded Market - Grant Deken

Grant Deken, Unstack

How Unstack Used Competitive Differentiation in a Crowded Market

Grant Deken is the co-founder and CEO of Unstack, a SaaS content marketing platform designed to help you rapidly build, measure, and scale your digital presence without writing code or hiring developers. In 2013, Grant co-founded an influencer marketing platform called Grapevine, which he eventually sold in 2019. During that time he worked with hundreds of advertisers and saw that a lot of them struggled when they had to quickly update their website or create a landing page. That got him thinking about what the ideal content management platform might look like. And he started having conversations with other founders about what they were doing to build out and manage their web presence. Eventually, he realized that there was a market for the type of product he'd been thinking about. So he basically pre-sold the idea to a few people and then spent the next few months building the first version of Unstack. He and his co-founder Steve charged for the product from the day they launched. And they were able to find their first 10 customers through their existing relationships. But getting to their first 100 customers was much more challenging. In this interview we talk about how they went from zero to a couple of hundred customers, how to position your product in a competitive and crowded market, how to differentiate your product without talking about feature comparisons, how to decide when your product is good enough for launch, building a community as a key channel for driving product growth, and how the Unstack team collaborated with integration partners as a way to reach their ideal customers faster.

How Insurmi Closed Six-Figure Startup Sales Deals in Insurance - Sonny Patel

Sonny Patel, Insurmi

How Insurmi Closed Six-Figure Startup Sales Deals in Insurance

Sonny Patel is the founder and CEO of Insurmi, a SaaS platform that helps insurance carriers generate leads, streamline claims, and deliver customer service through an AI-driven assistant. During his freshman year of college, Sonny got a job at an insurance agency in Arizona. He was surprised to see how the insurance industry was still operating with outdated technology. He wondered why it wasn't easier and faster for consumers to buy insurance online. A couple of years later, that question was still bugging him so he eventually decided to start Insurmi out of his dorm room. But Sonny didn't know how to code and needed help to get his idea off the ground. He eventually found an accelerator in Arizona that worked with him to develop his MVP for a B2C comparison website where you could shop for insurance. He spent the next year and a half trying to get his idea off the ground. But he soon realized that it was a crowded space and he'd need a lot of money to build a successful consumer product. Around that time, he also started talking to execs at insurance carriers. They were intrigued by what he was building and asked if they could license the software. That's when he realized that pivoting to a B2B product was a more interesting opportunity. In this interview, we talk about the pros and cons of working with a startup accelerator, how to have better customer conversations by learning to speak their language, how to develop a sales playbook to shorten your sales cycles and close six-figure deals, and how to get better at identifying and overcoming objections your prospects may have.

How Zomentum Found a Niche SaaS Market With Zero Code - Shruti Ghatge

Shruti Ghatge, Zomentum

How Zomentum Found a Niche SaaS Market With Zero Code

Shruti Ghatge is the co-founder and CEO of Zomentum, an all-in-one sales product built for IT managed service providers (MSPs). Shruti used to work as an investment analyst at a private equity firm. She noticed that a lot of companies were building great products, but struggled with marketing and sales. She and her co-founder Rahil identified this being an even bigger issue and opportunity with IT managed service providers. But neither of them had any experience with that market. So they spent six months doing customer development and resisted writing even a single line of code. And then they spent another 4 months building the product. When the product was ready, they sent out 2,500 cold emails to prospects. And they got a zero response rate - not even one person replied to their email. Both founders were discouraged and started second-guessing themselves. Maybe the problem didn't exist and they had spent the last year building a solution no one wanted. Their product lacked a lot of features and was unstable. And Shruti often felt embarrassed showing people the product and would worry that things were going to break during demos. But, they just kept going and trying different approaches. Eventually, they found a marketing channel that was working and started attracting some customers. Today, their business does multiple 6-figures in annual recurring revenue (ARR) and they've just raised $4M in funding.

Competitive Differentiation Grew This Podcast SaaS to $5M - Rob Loewenthal

Rob Loewenthal, Whooshkaa

Competitive Differentiation Grew This Podcast SaaS to $5M

Rob Loewenthal is the founder of Whooshkaa, a platform that helps creators and brands to produce, host, and monetize their podcasts. In 2014, Rob walked away from a job as the CEO of a radio network in Australia to launch a SaaS startup. His idea was to build an end-to-end technology platform to help podcasters. He was getting into a market that already had a lot of competitors. But Rob believed that there was an opportunity to do a lot more to help podcasters than just hosting and analytics. And in a relatively short time, he's been able to build a differentiated product that's now used by around 9,000 podcasts and enterprise SaaS companies like Cloudera and Atlassian.

How Vajro Used the Shopify SaaS Marketplace to Triple Revenue - Baskar Agneeswaran

Baskar Agneeswaran, Vajro

How Vajro Used the Shopify SaaS Marketplace to Triple Revenue

Baskar Agneeswaran is the co-founder of Vajro, a cloud-based mobile commerce platform that creates instant mobile shopping apps for e-commerce stores. You probably hear about product-market fit all the time and why that's so important to building a successful SaaS company. But what about founder-market fit? In 2015, Baskar and two of his friends set out to build a price comparison app. They wanted to get into the e-commerce space and believed they could help consumers find better deals. Two years later, their startup failed. They'd underestimated how much work was required to maintain the huge amount of data they needed to power their app. And as a bootstrapped business, they just didn't have enough money to keep going. But even though they failed, their experience helped them learn about e-commerce and more importantly about themselves. They knew their price comparison app was a great idea. It just wasn't a great idea for them. They realized that their strength was in mobile app development and that they were more likely to be successful if they focused on that. Soon after they came up with the idea of a SaaS product that helped Shopify stores to quickly and easily create a mobile shopping app. And it didn't take long for them to get traction. Then the pandemic hit and initially, it looked like their business was going to be in trouble. But instead of panicking, they started taking a closer look at what was going on. And they saw that mobile usage was increasing and it felt like there was actually an opportunity for them. So they decided to double down and actually hire more people during the pandemic. And in the last few months, they've tripled revenue and are doing 6-figures in MRR and still growing. It's a great story about the importance of founder-market fit. You may have a great idea, but it might not be the right idea for you. So figuring your founder-market fit is just as important if not more important than product-market fit - especially in the early days of your SaaS business. Enjoy the interview.

4 Failed Startups Before Finding Early Traction at $1M ARR - Abdullah Alsaadi

Abdullah Alsaadi, Taker

4 Failed Startups Before Finding Early Traction at $1M ARR

Abdullah Alsaadi is the co-founder and CEO of Taker.io, an online ordering platform and mobile app for restaurants. How many failed startups could you handle before you gave up? Abdullah was working as a security systems engineer in the Kingdom of Saudi Arabia. He had an idea for a cryptocurrency app. He was so excited about it that he jumped into building the product. After writing almost 30,000 lines of code, his app was ready. And that's when he realized he'd built a cool product, but there was no market for it. Sometime later, he had an idea to build an app on the Salesforce Platform. He'd learned his lesson from his last failure and had a clear market and customer in mind this time. But Salesforce wasn't set up at the time to support app developers in the Middle East. So Abdullah wasn't able to sell anything on their platform. He then decided to start a B2B last-mile delivery company. This time he made sure that customers could actually pay for his product. And his solution was a success and he had happy customers. But the business wasn't profitable and there was no easy way to find efficiencies and scale. His perseverance and grit kept Abdullah going. He pivoted to a delivery management software product. He knew this business could be profitable and his prospective customers loved his product. But they used legacy point of sale (POS) systems which were impossible to integrate with. It seemed like no matter what Abdullah tried, or how good his idea or product was, he just couldn't find success. It was failure after failure. Most of us might have given up by now. But Abdullah started working on his next idea. But he was out of money and didn't have the funds to build a new product. And he didn't exactly have a strong track record of success to persuade investors. Yet he found a way to build the product and get it to market. And this time things started to move in his favor. He's grown Taker.io from zero to almost a million US dollars annual run rate (ARR). There are some great lessons on what Abdullah did right with Taker.io and how he funded the development, found customers, and grew the business. But more importantly, he learned far more valuable lessons from all the failures he had over a period of 5 or 6 years. And that's what is really interesting about Abdullah's story. I hope you enjoy it.

From SaaS Blog to Global SaaS Community Events Business - Alex Theuma

Alex Theuma, SaaStock

From SaaS Blog to Global SaaS Community Events Business

Alex Theuma is the founder of SaaStock, global conferences that bring together SaaS founders, executives, and investors. Alex had been working in sales for many years, but he longed to start his own business and work for himself. But he didn't have any 'great' business ideas. He was interested in what was happening in the SaaS space. So he started writing a blog about what he was learning. And he also launched a podcast. As he started to build a following, he realized that there was an opportunity to connect people. So he organized meetups in London for people interested in SaaS. He really enjoyed bringing people together, but he wasn't making any money. Several people told Alex that he should do a SaaS conference in Europe to bring together more people. But he'd heard many horror stories about people who had done conferences and large events. So initially he was reluctant but then decided to jump in and do what people were asking for. In 2016, his first event in Dublin attracted 700 attendees and launched his business. He had finally found a great idea for his own business. In the next 4 years, he ran SaaStock events around the world every year. And now thousands were attending. But then the global pandemic hit and the event business he'd worked so hard to build came to a standstill. He had a simple choice - go out of business or find a way to pivot. He had to do some hard thinking and make tough decisions. In this interview, you'll learn how Alex has re-invented his business, what he's doing to rebuild, and why he's optimistic about future in-person events.

5 Days From Shutdown to SaaS Pivot That Found PMF - Romain Dardour

Romain Dardour, Hull

5 Days From Shutdown to SaaS Pivot That Found PMF

Romain Dardour is the co-founder and CEO of Hull, a SaaS product that collects, unifies, and enriches your product, marketing, and sales data and synchronizes it to all of your tools. In 2011, Romain was running a marketing agency in Paris. He was working with movie studios that wanted him to rebuild online communities from scratch for every new movie launch. He realized that there was a more efficient way to solve that problem and decided to build a product. And for the next 4 years, he and his co-founders struggled to find product-market fit. In 2016, after trying to unsuccessfully bootstrap the business for 4 years, they decided that the market just wasn't there and that it was time to move on. They made the decision to shut down the company. Around the same time, Romain had lunch with a growth marketer friend who wasn't interested in the product but liked how they were collecting and segmenting data. He thought that would be something a lot of companies would be interested in. So in the next 5 days, Romain and his co-founders built a prototype and started getting feedback. And that's how the idea for their new product was born. They went from being a month away from shutting down their company to finding a new opportunity which they pounced on and pivoted the business. Today, they charge at least $1,000 a month for their product and have around 100 customers. They've raised $5M in funding and have found product-market fit. In this interview, we talk about how they struggled in the first few years, how they turned a lunch meeting into a new product idea, and how they've grown their business.

5 Components of SaaS Positioning That Most Founders Skip - April Dunford

April Dunford, Ambient Strategy

5 Components of SaaS Positioning That Most Founders Skip

April Dunford is the founder of Ambient Strategy and author of "Obviously Awesome: How to Nail Product Positioning, so Customers Get it, Buy it, Love it." How clear are you on where your SaaS product fits in the marketplace? When you tell potential customers about your product (whether that's on your website, or in-person) do they get it? Do they understand where your product fits? And more importantly, are they clear about what makes your SaaS product unique, and do they understand how it's better than the alternative solutions? Positioning is what helps you get that clarity. And it's not just about writing a positioning statement. Creating your positioning is a process that your company needs to go through to figure out the best way to explain where your SaaS product fits in the marketplace and why your potential customers should choose you.

SaaS Metrics Obsession That Turned 12 Failures Into $5M ARR - Paul Joyce

Paul Joyce, Geckoboard

SaaS Metrics Obsession That Turned 12 Failures Into $5M ARR

Paul Joyce is the founder and CEO of Geckoboard, a SaaS product that lets businesses build and display real-time dashboards to help them focus on the metrics that matter. Paul was working at a bank in England. He hated his job and longed to start his own business. But this isn't one of those stories where someone comes up with a great idea, quits their job the next day, and becomes an overnight success. Paul spent four years looking for the right idea. He tried and failed a dozen times. But his burning desire to work for himself kept him going. And with each failure, he learned something. Eventually, in 2010 he came up with the idea for Geckoboard. He started building his MVP and also posted on Hacker News, which helped him build a waiting list of several hundred people. He launched his MVP a few months later but didn't get any paying customers. But he could sense from how enthusiastic people were, that there was something different about this idea. He decided that it was time for him to "go big or go home". So after talking to his wife, he used their savings to give him a five-month runway and quit his job to work on Geckoboard full-time. It was a huge leap of faith - but Paul's never looked back. Today, Geckoboard does well over $5 million in annual recurring revenue (ARR). The company has around 4,500 customers and a team of 40 people. In this interview, we talk about Paul's multiple failed attempts to start a SaaS company. We dig into why the idea for Geckoboard was different from all the other ideas he had. And we go into detail on how he found customers and eventually built a multi-million dollar SaaS business.

From Side Project to $10K MRR: How Friday Got Early Traction - Luke Thomas

Luke Thomas, Friday

From Side Project to $10K MRR: How Friday Got Early Traction

Luke Thomas is the founder of Friday, a SaaS product that helps distributed teams share regular updates and communication at work. The product started as a simple idea: if his former manager had just asked a few regular check-in questions, Luke would never have quit that job. Luke spent nearly three years thinking about the idea before launching a Ruby on Rails app in late 2015. He shipped the product in January 2016, and it took three months to land his first customer by emailing everyone he knew. That first customer paid $45 a month. With no plan and limited time, Luke tried everything to build early traction. He wrote 30 to 40 long-form blog posts targeting keywords like "weekly check-ins" and "one-on-ones" for managers. He left comments on Harvard Business Review articles - so many that he got banned and had to use a VPN. Both channels delivered measurable signups because he asked every new user how they found Friday. Luke started with freemium but switched to a three-week trial when he realized free users were not converting predictably and he was spending his own money to keep the product running. The switch immediately generated three to five new paying customers. A pivotal moment came when a team leader at a 150-person company wanted to roll out Friday company-wide. The expansion required months of work on roles, permissions, and multi-team features. Then came a devastating bug: a single line of code caused one company's check-in data to be emailed to employees at a different company. Luke calls it his worst day as a founder. Luke also pivoted toward HR tools when enterprise interest pulled him in that direction, but realized after a year it was wrong and pivoted back. He spent months talking to investors but failed to raise money because he could not explain why he was not working full-time. The early traction he had built gave him options, though. In 2019, three years after launch, Luke finally quit his job to work on Friday full-time at $10K MRR, raised a small round, rebuilt the product, and launched on Product Hunt a week before COVID sent everyone remote.

How a SaaS Pivot Saved a Startup Nobody Wanted - Sandi Lin

Sandi Lin, Skilljar

How a SaaS Pivot Saved a Startup Nobody Wanted

Sandi Lin is the co-founder and CEO of Skilljar, a customer training platform that helps enterprises like Tableau, Slack, and Asana improve product adoption and customer retention. When Sandi left Amazon, she built a prototype for a Yelp for online learning called Everpath. But within three months, she realized there was not enough value in the online learning aggregation market to build a real business. Instead of starting over from scratch, she decided to interview 50 instructors on the platform to dig for pain. The interviews revealed three pain points: video editing, marketing, and the need for a platform to distribute courses independently. Sandi and her co-founder designed a survey to fail - randomized questions with no leading structure - and were shocked when the learning platform concept won decisively. They built a stripped-down MVP in 60 days, manually processing everything on the backend. That SaaS pivot got them to ramen profitability at $49 per month per customer. But the real breakthrough came when larger companies started approaching them for a customer training solution. Sandi pivoted again to focus on enterprise, eventually building Skilljar into a platform serving mid-sized software companies. Along the way, Sandi struggled to raise a seed round because investors would not take meetings. She also failed multiple times at hiring a sales team before realizing that as a founder, she was the best person to lead sales - even though she did not believe she could sell. Today, Skilljar has raised over $20 million, has a team of about 100 people, and is approaching $10 million in ARR.

The SaaS Pivot That Turned an Internal Tool Into Hugo - Darren Chait

Darren Chait, Hugo

The SaaS Pivot That Turned an Internal Tool Into Hugo

Darren Chait is the co-founder and COO of Hugo, a SaaS product that provides connected meeting notes for teams. Darren used to work as a corporate lawyer in Australia. He became frustrated with how inefficient meetings were and had an idea for improving things. He partnered up with a close friend, and they built a mobile app that helped people prepare for meetings. It seemed like a great idea. And it did not take the founders long to get a couple of thousand users. But they found it hard to monetize the product, and sales were slow. At the same time, their team was struggling with internal communication. Someone had the idea to build a simple Slack plugin that reminded everyone to share notes after every meeting. It was a simple solution, but within weeks they saw huge benefits and better team communication. So they kept improving their tool and adding new features. One day, during a customer meeting, Darren was using the tool to share notes with his team. His customer was intrigued and asked if their company could also try out the software. That is when the founders started to realize that their internal tool was far more valuable than the mobile app they were trying to sell. So they pivoted and focused instead on selling their tool. It was a simple idea but still hard for people to understand. The founders struggled with their messaging. When you are creating a new product category, people are not looking for your product. And sometimes they do not even realize they have the problem that you are solving. There are some great lessons in this interview about figuring out your value prop and messaging, how the most straightforward solutions are often the best business opportunities, and using product-led growth to drive user adoption and revenue. I hope you enjoy it.

How Mutiny Got First SaaS Customers With a 2-Week MVP - Jaleh Rezaei

Jaleh Rezaei, Mutiny

How Mutiny Got First SaaS Customers With a 2-Week MVP

Jaleh Rezaei is the co-founder and CEO of Mutiny, a SaaS product that helps B2B companies personalize their website for each visitor in order to close more sales. As a product marketer at VMware, Jaleh got to work with a lot of salespeople and soon realized one thing that made the difference between great salespeople and average ones. The best salespeople knew how to adapt and personalize the conversation for each customer. And so they were more successful at closing deals, which typically were worth over $100,000. In 2011, she joined Gusto when they only had around 10 employees. With an average deal size of just $500, Jaleh had to quickly become really good at online customer acquisition. She wondered if she could create a more personalized experience for people who visited their website. But quickly realized how hard that was with the tools available to her at the time. So when she eventually had the chance to solve that problem, she jumped at it. Jaleh and her co-founder were accepted into YC and built their MVP in just 2 weeks. It was a simple API and a pitch deck. They didn't even have a demo to show people. It's hard getting prospective customers to use your product - even if you don't charge for it. They have to learn how to use the product, which requires a time commitment. And since you're just starting out, they don't even know if your product will actually help them or not. So the founders decided to get really hands-on with their first SaaS customers. They worked as an extension to their teams to create content, help them launch and measure the results. It wasn't scalable but turned out to be a great way to learn about their first SaaS customers and find product-market fit. To date, the founders have raised over $3 million. There are some good lessons in this interview. For example, you may have a big idea, but you don't have to take months or years to launch an MVP. Think big, but start small.

How a Niche SaaS for Direct Sellers Hit $5M ARR - Jennifer Johnson

Jennifer Johnson, CinchShare

How a Niche SaaS for Direct Sellers Hit $5M ARR

Jennifer Johnson is the founder and CEO of CinchShare, a social media marketing product for home-based direct sales businesses. In 2013, Jennifer, a stay-at-home mom, was trying to use Facebook to get more sales for her side business. The more active she was on Facebook, the more sales she seemed to get. But this often meant spending over two hours a day scheduling Facebook posts. And as a mom of four kids, it was really hard for her to find that much time every day. So she signed up for different social media marketing tools such as Hootsuite, Buffer, and PostPlanner. But they didn't actually save her that much time. She wanted a tool that would simplify and speed up all the repetitive tasks she was doing. Her husband didn't have experience building software but was technical enough to eventually be able to create a simple tool to schedule Facebook posts the way she wanted. He built it in about four weeks on evenings and weekends. And overnight, she went from two hours to just 20 minutes a day to schedule Facebook posts. Eventually, they built a website and started selling this niche SaaS tool to other home-based business owners. They had about 600 people join their Facebook group within weeks. When they opened for business, people flooded the site. Several hundred signed up on the first day. It wasn't all smooth sailing. In May 2015, a version 2.0 update broke everything. Hundreds of angry customers. Jennifer in tears. Her husband hyperventilating. But they rolled back, communicated transparently through their Facebook group, and their community rallied around them. Today, Jennifer's niche SaaS business does over $5 million in annual recurring revenue. The business is bootstrapped, profitable, and she's taken zero outside investment.

One Year to First SaaS Customers Then $1M ARR - Uri Haramati

Uri Haramati, Torii

One Year to First SaaS Customers Then $1M ARR

Uri Haramati is the co-founder and CEO of Torii, a SaaS platform that helps you discover, optimize and control your organization's SaaS usage and costs. Looking for a SaaS business idea? Maybe you just need to solve something that frustrates you. Uri was having a hard time keeping track of all the SaaS applications that were being used at his company. He talked to his peers in the IT space and realized they had the same problem. He wondered how much demand there was for a solution that solved this frustration. He looked around for solutions, but couldn't find something that really solved the problem well. So he and his two co-founders developed an MVP in two weeks. All it did was connect to your bank account and generate a simple report of your SaaS subscriptions and costs. They used their network to find companies that needed their solution. They didn't charge for their MVP. They just kept talking to users, collecting feedback and improving the product. In fact, it took them one year to get their first SaaS customers. But the real milestone was when they signed Pipedrive - their first unaffiliated customer. They emailed Pipedrive's IT team saying "We use your tool and love it. We thought you might want to see Torii." That simple cold outreach converted into a paying customer. The year of relentlessly focusing on their potential first SaaS customers and their product was starting to pay off. They had about 50 paying customers and were closing in on their first million dollars in ARR.

10 Years of Failure Before Bootstrap to Profitability Worked - Dennis van der Heijden

Dennis van der Heijden, Convert.com

10 Years of Failure Before Bootstrap to Profitability Worked

Dennis van der Heijden is the co-founder, and CEO of Convert.com, an A/B testing and website conversion optimization tool. Dennis has grown Convert.com into a profitable multi-million dollar SaaS business. His fully remote team is spread across 9 timezones. And he's built a company culture that he's proud of. But things weren't always like that. When he started out, he faced failure after failure. And he'll be the first one to admit that he did just about everything wrong. He was living in the Netherlands and read TechCrunch every day. His dream was to get VC funding. He wanted the Silicon Valley startup experience. He wasn't thinking about customers. As Dennis told me I wanted to get VC funding and customers were just a way to get there. And when he did raise funding, he celebrated as if he'd achieved his end-goal. But that money soon ran out. And that's when he started to realize that VC funding wasn't the answer. But things got even worse before they got better. He struggled with the business and his personal life for a few years. In fact, it took almost 10 years for things to come together for him. What I loved most about talking to Dennis is how open and vulnerable he was willing to be during the interview. He lays it all out there and shares all his failures and mistakes. And the lessons he shares are powerful and inspiring. It's a great story and he's a great guy. I hope you enjoy it.

400 Signups but Zero Paid: How He Found His First SaaS Customers - Ryan Born

Ryan Born, Cloud Campaign

400 Signups but Zero Paid: How He Found His First SaaS Customers

Ryan Born is the co-founder, and CEO of Cloud Campaign, a SaaS platform that helps agencies to manage multiple brands on social media at scale. Ryan was working as a software engineer in the San Francisco area. Like most developers, he loved building things. And he was always tinkering on side-projects. His latest idea was a social media management tool. He created a few mockups for a product that didn't exist yet and published a landing page to see if anyone was interested. The next day he turned up at work and heard a big announcement. The company he worked for had been acquired, his office was being closed and he was going to be laid off. As he's sitting in this meeting, his phone's going crazy. It keeps buzzing every couple of minutes. Turns out he was getting notified every time someone signed up on his landing page. He was blown away by how many people were interested in a product he hadn't even built yet. Ryan started building the product and quickly launched the beta. He listed it on sites like Product Hunt and Beta List. And it wasn't long until he had 400 people signed up. That got him even more excited about his product. So next, he added a paid plan and tried to get people to upgrade. But not even one person paid for the product. He tried cold email outreach in the hope of finding customers. But that didn't work. He tried running paid ads. But that didn't work either. His savings were running out fast. And he had a very limited runway to make this business work. But where was he supposed to go from here? It seemed like nothing was working. Fast forward to today, Ryan's business is generating around $25K in monthly recurring revenue. And he's found a scalable marketing channel that's working well for him. In this interview, you'll learn what exactly Ryan did to turn things around. We talk about all the things he tried that didn't work and the important lessons he learned. And we deep dive into exactly how he found customers and how he's grown revenue. If you're bootstrapping or still trying to find product/market fit, I think you'll love this interview. It's jam-packed with some great strategies, lessons, and insights. I hope you enjoy it.

$170K in 2 Weeks: How Lemlist Got First SaaS Customers - Guillaume Moubeche

Guillaume Moubeche, Lemlist

$170K in 2 Weeks: How Lemlist Got First SaaS Customers

Guillaume Moubeche is the co-founder and CEO of Lemlist, an automated email outreach platform that uses personalized images to get more replies from cold emails. Guillaume was running a B2B lead generation agency in Paris. He was sending out a lot of cold emails on behalf of his clients. He was getting results but felt he could be doing much better. He knew that highly personalized emails got more replies. But it was really hard to do that at scale. And automated solutions did basic personalization like replacing the first name. So he started looking around for an automated solution that would help him do advanced things like sending personalized images with each cold email. But he didn't find anything. That's when he realized there might be an opportunity to build a software product. He partnered with a couple of developers and they built a very ugly beta in about two weeks. In that first month, they had about 100 people sign up for the product. The product did the job, but the editor was almost impossible to use. His users told him they loved the idea, but the product lacked 90% of the features his competitors had. Around the same time, he got an email from someone at AppSumo who had come across his product and told him they were interested in doing a promotion in a couple of months. It was a great opportunity, but they knew the product had to get much better fast. A couple of months later, their product was promoted on AppSumo and in a couple of weeks they generated around $170,000 in sales. Most people loved the product. From there, they used Product Hunt (finishing as the number one product of the day), Capterra reviews, LinkedIn outreach, and a Facebook community to keep growing. They hit $250K ARR in under two years while staying bootstrapped.

How Kissflow's SaaS SEO Strategy Generates 50% of All Leads - Suresh Sambandam

Suresh Sambandam, Kissflow

How Kissflow's SaaS SEO Strategy Generates 50% of All Leads

Suresh Sambandam is the CEO of Kissflow, the first unified digital workplace for organizations to manage all of their work on a single, unified platform. Kissflow is used by over 10,000 customers across 160 countries, including more than fifty Fortune 500 companies. Suresh was working as an engineer for a startup when he spotted an opportunity for a business idea. He eventually quit his job to launch his startup in 2003. Things looked promising at the start. Before he knew it, he had a team of 40 people. But the product just didn't get the traction he'd hoped for and he eventually had to pivot. With his new idea, he raised $1M from angel investors. But he was too early to market. And by the following year, he was running out of money and had to layoff most of his employees. And then in 2013, a customer helped him see the potential of his product. A UK based design company bought his product for $50K but then spent another $90K on building a great user interface for it. That was when Suresh had his aha moment. He realized that as an engineer, he'd been focusing too much on features and technology. Instead, he had to get his company building great user experiences. And that's when things started to click with his third pivot (which became KiSSFLOW). The more the team focused on creating a great user experience, the more their product resonated with customers. Today his company is doing close to $10M in ARR and has over 200 employees. We talk about his multiple pivots, the 10 years it took to find product/market fit, his strategic approach to search engine optimization and how that now drives over 50% of leads. And we talk about what Suresh calls "Desk Marketing & Selling" which his team based in Chennai, India is using to land B2B customers around the world.

300 Customer Interviews to SaaS Product-Market Fit - Alex Yakubovich

Alex Yakubovich, Scout RFP

300 Customer Interviews to SaaS Product-Market Fit

Alex Yakubovich is the co-founder and CEO of Scout RFP, a SaaS product that helps large enterprises automate their strategic sourcing and procurement process. Before Scout RFP, Alex and his co-founders built an online ordering platform for restaurant chains while still in college. What started as a way to make beer and pizza money grew into a business serving major chains like Panera, Jersey Mike's, and KFC, processing hundreds of millions in transactions. They sold that business to Living Social for tens of millions of dollars. But during those years of selling into large enterprises, Alex experienced firsthand how broken the procurement and RFP process was. So when they started their next company, they took a radically different approach to finding SaaS product-market fit. His co-founder Stan proposed a rule: don't build anything until you've talked to at least 200 people in procurement. They ended up interviewing close to 300 people over six months. That research revealed something surprising - the market was full of software from SAP, Oracle, and other giants, but adoption was terrible because the tools were too complex. Scout RFP launched with a one-page application so minimal that prospects would ask "is that it?" But once they used it, they loved the simplicity. The team achieved SaaS product-market fit by focusing on adoption and ease of use rather than feature count. That approach attracted some of the world's biggest brands, and the company grew to over 150 employees with $60M in funding. There are some great lessons here about the power of deep customer discovery, why simplicity beats features, and how to build enterprise SaaS that people actually want to use.

From $4K to $32K AOV: The Pricing Strategy That Saved Brightpearl - Derek O'Carroll

Derek O'Carroll, Brightpearl

From $4K to $32K AOV: The Pricing Strategy That Saved Brightpearl

Derek O'Carroll is the CEO of Brightpearl, a cloud-based enterprise resource planning product for retailers and wholesalers. In 2016, a SaaS company founded in a small city in the UK was struggling with a business model that was unsustainable. After almost 10 years in business, the company was struggling to retain customers and was quickly running out of money. That same year, Derek was hired as the new CEO to turn around the company. He spent his first 60 days interviewing every single one of the 100 employees, plus partners and customers. He built a list of 42 things that needed fixing, then narrowed it down to 10 projects and three core focus areas. The most critical change was a new pricing strategy. Brightpearl had been using per-user pricing with nickel-and-dime add-ons. Derek discovered they were charging just 0.23% of customer GMV when they should have been at 1%. He switched to a tiered GMV-based pricing model, killed monthly billing, and mandated professional services for onboarding. The pricing strategy shift had an immediate side effect - they deliberately shed customers. Derek took the customer count from 1,400 down to 872 by dropping small retailers who were churning at high rates through corporate bankruptcy. But dollar retained revenue doubled. They also fixed their go-to-market. With the old $4,000 AOV, outbound sales didn't pencil out economically. Once the pricing strategy pushed AOV to $32,000, they could afford outbound and partner teams. Within two years, 40% of pipeline came from those new channels and customer acquisition cost improved 5x. In the last three years, revenue has more than doubled to nearly $13M ARR, growing at 45% year over year. Churn dropped from 28% to 12% and is trending toward single digits.

Calendly Founder Tope Awotona: Product-Market Fit After 3 Failed Startups - Tope Awotona

Tope Awotona, Calendly

Calendly Founder Tope Awotona: Product-Market Fit After 3 Failed Startups

Tope Awotona is the founder and CEO of Calendly, a scheduling platform that eliminates the back-and-forth emails required to book meetings. Tope Awotona grew up in Nigeria and moved to the US as a teenager. After graduating from the University of Georgia, he landed a sales job at IBM and spent the next seven years in enterprise software sales. But he always wanted to be an entrepreneur. So he spent his evenings and weekends trying to build businesses. First, he read an article about PlentyOfFish.com making millions and decided to build a dating site. He bought domains, created a holding company, and purchased dating software—but never launched it because he lacked the skills and resources. His second startup was an e-commerce site selling projectors. He made some sales, but the margins were terrible and he had zero interest in projectors. His third startup was another e-commerce site, this time selling grills. Same problems: thin margins, no passion, no traction. Tope realized he was focused on "ways to make money" instead of solving problems he cared about. He told himself he wouldn't succeed unless he found a problem he was passionate about solving. It took another year before he found that problem. After wasting an entire day trading emails to schedule a single meeting, he searched for a scheduling tool. Everything on the market was slow, clunky, and poorly designed. He spent six months researching competitors, studying their user communities, and identifying what they did well and where they failed. Unlike his previous attempts, this time he went all in. He emptied his bank account, flew to Ukraine to hire engineers, and committed everything to building a better product. The bet paid off. Calendly launched in 2013 as a free product (not by choice—they ran out of money before building billing). That accident turned into one of the best decisions they never made. The freemium model combined with viral sharing made it easy for users to spread the product. At the time of this interview, Calendly was generating $30M ARR and serving 4 million users, largely bootstrapped. Tope's journey from three failed startups to finding product-market fit offers a masterclass in patience, persistence, and solving problems you actually care about.

Building AI Products: 5 Years and 33M Data Points to Ship - Dennis Mortensen

Dennis Mortensen, x.ai

Building AI Products: 5 Years and 33M Data Points to Ship

Dennis Mortensen is the founder and CEO of x.ai, an artificial intelligence-driven personal assistant that schedules meetings for you. Dennis had just sold his company and had plenty of time on his hands. So he did what any curious founder would do - he opened his calendar and counted. 1,019 meetings in one year. 672 of them rescheduled. That pain point was real, but Dennis did something unusual. Instead of falling in love with the idea, he spent months trying to convince himself not to build it. First, he and his VP of engineering played each other's scheduling assistants over email. Then he hired a full-time human assistant and offered her services to 50 friends to see if the joy of delegating scheduling was real - and whether the patterns were predictable enough for a machine to eventually handle. When he could not kill the idea, he raised a $2 million seed round with a radical pitch: the only outcome would be a thumbs up or thumbs down on whether building AI products for meeting scheduling was even technically feasible. No MVP. No customers. No revenue. Just a data labeling exercise to map the entire universe of scheduling intents. Five years and $44 million later, x.ai had 70 people in Manila labeling data and 50 engineers in New York. They labeled 33 million elements through supervised learning. And Dennis reveals that x.ai is about to hit its inflection point - the moment where building AI products shifts from manual annotation to the product learning from its own usage. Dennis also shares why he believes founders should try to invalidate their startup ideas rather than validate them, the difference between taking a technical risk versus a market risk, why freemium failed for x.ai, and how more than half their signups came from the product's built-in virality.

3 SaaS Pivots, a Cease and Desist, and $5M ARR - Max Kolysh

Max Kolysh, Zinc

3 SaaS Pivots, a Cease and Desist, and $5M ARR

Max Kolysh is the co-founder of Zinc, an e-commerce lab that builds products to help Amazon and eBay sellers. Every SaaS founder knows that finding product-market fit is really tough. You might have to pivot your SaaS business multiple times before you find the right product for the right market. So what can we learn from SaaS founders who failed repeatedly before they found success? When Max and Doug were students at MIT, they talked about building a software product to help eBay sellers. And eventually, they both dropped out of college to start their business. They got accepted into YC but pretty soon realized that their idea was not that great after all. So within a few weeks, they made their first SaaS pivot and built a product that saved people money when buying on Amazon. They got some good traction and it looked like they were on their way to finding product-market fit. But that all changed when they received a cease and desist letter from Amazon. So they were back to square one again. They needed another idea. One day they received an email out of the blue from an ex-customer who told them that he wanted to use an API but was not technical. He asked them if they could help him out. That email led to Max and Doug pivoting again and creating a new product. But this time it was not just an idea they had come up with themselves - it was something a real customer needed. And the product resonated with the market and helped them get traction. Today, their company generates over $5 million in annual recurring revenue. It is a great story about persistence, flexibility, listening to your customers, and how to successfully execute a SaaS pivot.

Customer Acquisition Startup Mistakes That Kill Your Idea - Rob Fitzpatrick

Rob Fitzpatrick, The Mom Test

Customer Acquisition Startup Mistakes That Kill Your Idea

Rob Fitzpatrick is a tech entrepreneur and author. He ran various tech startups for about 10 years, has raised funding in the US and UK, and is a YC alum. He is the author of The Mom Test - How to Talk to Customers and Learn if Your Business is a Good Idea When Everyone is Lying to You. He is also the author of The Workshop Survival Guide - How to Design and Teach Workshops That Work Every Time. One of the biggest challenges you face as a SaaS founder is validating your idea. It might be an idea for a new company or something that you want to change in your existing business. You are excited about the idea. But how do you know if your prospective customers will love it too? And more importantly, how do you know if people will pay money for your idea? Most founders know that they have to talk to customers to validate their idea. But it is easy to screw up customer interviews and hard to do them right. In this episode, Rob walks through a step-by-step process to improve how you run customer conversations for customer acquisition at a startup. We talk about how to ask good questions, how to avoid collecting bad data, and how to know when people are lying to you or telling you what they think you want to hear. By the end of this episode, you will know how customer conversations can go wrong and how you can do a better job at learning if you really have a good idea or not.

What 2 SaaS Exits Taught This AI SaaS Founder - Rob Kall

Rob Kall, Cien

What 2 SaaS Exits Taught This AI SaaS Founder

Rob Kall is the co-founder and CEO of Cien, an AI SaaS product that helps sales teams get an edge by using artificial intelligence to enhance data quality and improve sales productivity. Rob is a serial entrepreneur who has built and exited two previous SaaS companies. Rob's first company, eNeighborhoods, built websites for real estate agents and grew rapidly during the real estate boom. He and his co-founders sold it for $80 million after six years. The idea started with almost no research - his co-founder liked real estate, Rob liked building software, and the websites they saw were bad. Their secret sauce was building sophisticated MLS data feed technology that allowed them to go national while competitors stayed local. His second company, Bookt, provided back-office SaaS for vacation rental managers. Growth was painfully slow until they started partnerships with marketing platforms like HomeAway and TripAdvisor, which referred customers to them. But a right-of-first-refusal agreement with one partner nearly destroyed their ability to raise a Series A - VCs would not invest in a company that someone else had the option to buy first. Rob eventually renegotiated the agreement and sold the company for $15 million. Now with Cien, Rob is tackling AI SaaS for sales productivity. After his second company was acquired and merged into a team of 100 salespeople, he saw firsthand that scaling a sales team does not automatically scale revenue. Cien measures lead quality, seller attributes like closing ability and product knowledge, and macro factors like seasonality to give sales leaders a complete picture of what drives results. The consistent theme across all three companies: building in markets with strong tailwinds - real estate in 2001, vacation rentals before Airbnb exploded, and now AI SaaS during the machine learning wave.

7 Years of Self-Funded SaaS Before the Product Worked - Omer Artun

Omer Artun, AgilOne

7 Years of Self-Funded SaaS Before the Product Worked

Omer Artun is the founder and CEO of AgilOne, a predictive marketing platform for business-to-consumer brands. AgilOne allows marketers to understand and predict customer behavior to deliver automated, personalized experiences across all customer touchpoints, online and offline. Omer's story is a masterclass in the self-funded SaaS approach. With a PhD in physics and computational neuroscience, he spotted the opportunity to apply machine learning to B2C marketing while consulting at McKinsey. But he had no funding and no product. So in 2005, he started a consulting practice, solving data problems for large brands one project at a time. By 2008, he had productized his service enough to start charging subscriptions. Customers were logging into what looked like a SaaS product, but behind the scenes it was hosted software with a separate database for every client. Omer was profitable by month 10 and grew to 35 people on services revenue alone before raising his first round in 2011. After raising $51 million total, Omer made what he calls his biggest mistake: trying to build the product while simultaneously scaling sales. The first version of the platform used immature big data technologies that did not scale, forcing a complete rebuild in 2014. The second version shipped in late 2015 and became the foundation for real growth. The episode covers why it took Omer two years after raising money to truly understand what "product" means, why being eight years early to a market category means burning money to educate buyers, and how asking for ROI calculators and proof-of-concept pilots are signals that your self-funded SaaS market is not yet mainstream.

From Losing 8 of 10 Deals to Winning With Niche SaaS - John Stojka

John Stojka, Sertifi

From Losing 8 of 10 Deals to Winning With Niche SaaS

John Stojka is the co-founder and co-CEO of Sertifi, a niche SaaS product that enables companies to electronically sign contracts and collect payments quickly and easily. In 2008, John and his brother Nick had the idea of building an e-signature product. They landed their first customer, CareerBuilder, and quickly scaled to a thousand users within that single account. Things were looking good until they were served papers for patent infringement by a competitor that had raised over $500 million. Fighting that lawsuit took eight months and cost close to $150,000 - nearly all of their revenue at the time. After surviving the lawsuit, the brothers realized a bigger problem: they were a "me too" player in a crowded market, losing 8 out of 10 competitive deals to better-funded rivals like DocuSign and Adobe. John knew they needed to find a niche SaaS approach rather than competing head to head. He spent 12 months visiting trade shows across a dozen verticals - finance, real estate, insurance, home healthcare, and events. He settled on the events vertical because no competitor had saturated it yet, and customers had an additional pain point beyond signatures: they needed payment collection. Even within the 60,000-70,000 event companies in the US, John narrowed further to just 300 property management companies. The counterintuitive lesson was clear: the smaller the market, the faster Sertifi grew. With that niche SaaS focus, they went from $1M ARR to over $10M ARR, grew to 60 employees, and processed nearly $2 billion in payments - all completely bootstrapped. Their first events customer, Dave and Buster's, switched from a competitor specifically because Sertifi solved the payment capture problem that no one else addressed.

Founder-Led Sales: From Failed Launch to 7 Figures - Christian Owens

Christian Owens, Paddle

Founder-Led Sales: From Failed Launch to 7 Figures

Christian Owens is the founder and CEO of Paddle. Paddle is a SaaS product that helps other software companies sell their products. It provides checkout, subscriptions, taxes, licensing, and insights in one unified platform. Christian learned to build websites when he was 12 years old. He started walking into local businesses and asking them if they wanted a website. Some business owners just laughed at him, but others hired him to do the job. At the age of 15, Christian built an invoicing application for Mac. But he had no idea how to sell software and no money to spend on marketing. So he started contacting other people with Mac products and persuaded them to do a special 2-week promotion where they would combine all their products into a heavily discounted bundle and promote that to all their existing customers. The promotion was a huge success and they made over $400,000 in sales in 2 weeks. At the age of 16, Christian dropped out of school and focused 100% on this business and kept running these bundle promotions. By the time he was 18, he had already made his first million dollars. In 2012, Christian founded Paddle with his co-founder Harrison. They wanted to make it easier for software companies to sell their products. But they quickly realized that they had a big problem - nobody wanted their marketplace product. The first two months generated just $800 in total sales. Then something surprising happened. Customers started hacking around the marketplace to use just the checkout page directly. Christian realized they did not want the marketplace skin - they wanted the guts: checkout, billing, taxes, and licensing. So the founders threw away 90% of the product and focused on that one thing. From there, founder-led sales drove almost all of Paddle's growth. Christian and Harrison built internal tools to find leads, manually wrote personalized cold emails, and grew the business to over $10 million in annual recurring revenue with 140 employees. The journey from failed launch to $10M ARR shows the power of founder-led sales combined with the willingness to listen when customers tell you what they actually want.

3 Products, 1 Winner - Finding Product-Market Fit - Bart Lorang

Bart Lorang, FullContact

3 Products, 1 Winner - Finding Product-Market Fit

Bart Lorang is the co-founder and CEO of FullContact, a SaaS product that helps you manage your contacts and relationships better. It transforms partial contact information into complete profiles and more useful customer data. Bart came up with the idea for his business when he looked at how well his wife organized her contacts in Outlook. And he started thinking how great it would be if he could build software to enrich his own contacts data. He and his co-founders developed a simple tool called Rainmaker that would automatically update your Google contacts with data from social networks. They launched it in Google's marketplace and it did not take long for them to find the first few customers. But then they did what many founders do. They had another product idea they were excited about, so they started working on that instead. For many months, they pretty much ignored Rainmaker other than fixing a bug or two. After a few months working on that second product, they had another idea for a third product. So they started working on that too. Eventually they had three different products, one of which had paying customers who loved it. They were spreading themselves too thin and realized they needed to focus. The process of finding product-market fit meant accepting that only one of their three products had real customer demand. In the end, they decided to double down on the idea that customers were already voting for with their wallets. They rolled everything into what eventually became FullContact. The company has since raised over $25 million in funding and grown to over 300 employees. In this interview, Bart shares the lessons he learned about focus, finding product-market fit, and why sometimes the best idea is the one you are already ignoring.

After the SaaS Exit: Why His Next Startup Failed - Hampus Jakobsson

Hampus Jakobsson, BlueYard Capital

After the SaaS Exit: Why His Next Startup Failed

Hampus Jakobsson is a serial entrepreneur, angel investor, and venture capitalist. He is currently a venture partner at BlueYard Capital, a VC firm based in Europe, and an angel who has invested in over 80 companies. In 2002, Hampus co-founded TAT, a company that developed and licensed mobile user interface software to companies such as Motorola, Samsung, and Nokia. TAT was acquired by BlackBerry in 2010 for $150 million - a SaaS exit that came just eight years after the company was started by six university friends. In 2012, Hampus co-founded Brisk, a SaaS product designed to make sales teams more productive. That startup failed and was shut down four years later. Hampus believes Brisk failed because the team built a product they thought was cool rather than solving a real customer problem. They spent too much time on elegant engineering and not enough on SaaS exit-defining fundamentals like product-market fit. In this interview, Hampus talks about the contrast between building a company that achieved a $150 million SaaS exit and one that failed. He shares what he wishes he had done differently with Brisk, including talking to more customers earlier and validating pain before writing code. And he talks about life as an angel investor and what types of companies and founders he invests in.

From Near Death to Selling a SaaS Business After 21 Years - Mike Hilton

Mike Hilton, Concur

From Near Death to Selling a SaaS Business After 21 Years

Mike Hilton is the chief product officer of Accolade, a healthcare technology platform that partners with large, innovative employers to simplify and improve healthcare for employees and their families. Previously, Mike was the co-founder of Concur, a travel expense and invoice management product. Mike and his two co-founders launched the business in 1993 from an apartment and self-funded it for the first year. In 2014, 21 years later, they sold that business to SAP for a mind-blowing $8.3 billion. They started out with a Windows product which they sold for $69. And eventually became a SaaS business in 2001. And in order to build the SaaS business, they had to bet the entire company and risk all the revenue they were generating from their existing on-premise product. It's clearly not an overnight success story. The founders put 21 years into the business. They became a public company in 1998 and grew to a market cap of $1 billion and a share price of $60. But within a couple of years, their market cap dropped from $1 billion to $8 million and their share price went from $60 to 28 cents. They were losing money and hemorrhaging employees. They were written off for dead. But they figured out a way to keep going, bet everything on cloud, and eventually turned Concur into a story about selling a SaaS business after 21 years of persistence, reinvention, and playing the long game.

SaaS Product Validation: Lessons from Failure - Mike Taber

Mike Taber, Bluetick.io

SaaS Product Validation: Lessons from Failure

Mike Taber is the founder of Bluetick.io, a SaaS product that automates the process of sending follow-up emails while keeping it personal. Mike is also the co-host of Startups for the Rest of Us podcast and he's the co-founder of MicroConf, both of which he runs with Rob Walling, the founder of Drip. His last startup was AuditShark, a software product that helped regulated businesses such as financial companies to ensure IT security compliance. He tried for several years to get that business off the ground. It was a long, painful effort trying to make it work, but in the end, the business failed. Mike believes that it wasn't a product-market fit issue, but a product-founder fit issue. In other words, the business wasn't a good fit for him as a founder. Selling to enterprise customers typically involves outbound sales. Mike wasn't comfortable doing that and probably wasted a lot of time trying to acquire customers in different ways. With Bluetick, Mike applied rigorous SaaS product validation - building 80 mockups, conducting 40-50 interviews, collecting $2,000 in prepayments, and using a name-your-price form to discover market pricing before writing any code. We talk about the lessons he learned and how he's making sure he doesn't make the same mistakes again.

SaaS Customer Acquisition Playbook: 0 to 10,000 Customers - Mikita Mikado

Mikita Mikado, PandaDoc

SaaS Customer Acquisition Playbook: 0 to 10,000 Customers

Mikita Mikado is the co-founder and CEO of PandaDoc, a SaaS product that lets you create, deliver, and manage your team's quotes, proposals, contracts, and other sales collateral. Before launching PandaDoc, Mikita and his co-founder Serge were running another business together in Belarus. They had to send out a lot of sales proposals and contracts. It was tedious and time-consuming for them to create and track all these documents. And after investing hours into putting a document together, they had no idea if their prospective customer had even looked at it. So eventually, they decided to solve this problem, not just for themselves but also for other people running similar businesses. They built a SaaS product called QuoteRoller and launched it in 2011. They got some initial traction, but soon realized they hadn't quite built the product the right way and were spending too much time arguing with each other about features instead of talking to customers. A couple of years later, they built and launched PandaDoc and took it from zero to over 10,000 customers using a SaaS customer acquisition strategy built on CRM partnerships, product virality, and relentless experimentation. You'll also hear a great story on how Mikita's sense of humor helped them find an investor in the most unexpected way. I hope you enjoy the interview.

SaaS Growth Lessons from $800 MRR to $4.5M a Year - Kyle Racki

Kyle Racki, Proposify

SaaS Growth Lessons from $800 MRR to $4.5M a Year

Kyle Racki is the co-founder and CEO of Proposify, a SaaS product that helps you create proposal documents, collaborate with your team, and streamline your sales process so you can close deals faster. The company was founded in 2014 and is based in Halifax, Nova Scotia. Kyle and his co-founder Kevin came up with the idea for Proposify when they were running a design agency. But they did not do anything with that idea for several years. Eventually they decided that they wanted to get out of the agency business and went back to their idea. They built a prototype and got a lot of positive feedback. But when they launched, the results were disappointing. They got to around $800 a month in MRR and flatlined there for almost a year and a half. Today, their business generates over $4.5 million in annual recurring revenue. The SaaS growth unlock came from a single product change - pre-built proposal templates. Before that, customers had to manually copy-paste their existing proposals into Proposify, which created massive onboarding friction. Once Kyle's team created 20 professionally designed templates for specific industries, new signups could pick one, customize it, and start closing deals immediately. MRR jumped from $800 to $1,500, then $3,500, then $8,000 in consecutive months. We talk about what kept them going during those 17 months of SaaS growth stagnation and deep dive into the specific things they did that led to their hockey-stick growth.

Selling SaaS Without Sales Experience Changed Everything - Hannah Chaplin

Hannah Chaplin, Receptive.io

Selling SaaS Without Sales Experience Changed Everything

Hannah Chaplin is the co-founder and CEO of Receptive.io, a platform that helps SaaS companies identify the highest-impact things their team should be working on right now. The platform helps to gather feature requests and feedback from customers, internal teams, and the market, and turns that data into clear and actionable insights. Receptive.io was founded in 2015 and is based in Sheffield, England. The founders came up with the idea for Receptive when they were running another business and struggling to manage feature requests and feedback from their own customers. After building an MVP, they joined an accelerator in England and spent about five months doing customer interviews. They learned that they were focusing on the wrong customers and needed to think bigger. But once they built the product, they had a hard time selling SaaS without sales experience. They had to learn everything from scratch - how to run demos, how to handle enterprise procurement, and how to get buy-in from multiple stakeholders. Hannah shares how content marketing, Quora, and an early investment in customer success became the foundation for selling SaaS without sales experience and growing Receptive into a platform with over a million end users.

The One Person SaaS Business Making Over $1M a Year - Mike Carson

Mike Carson, Park.io

The One Person SaaS Business Making Over $1M a Year

Mike Carson is the founder of Park.io, a service that helps you to backorder expiring domain names. Mike is a developer who for many years struggled to find business success. He was working hard on multiple projects. But none of them were working out. And it was a painful time for him. He could not understand why he kept failing. And he would often wonder if he was not working hard enough or just doing things the wrong way. One day he just decided to let go of all that frustration and work on a project that he was curious and passionate about. He was not even thinking of it as a business. And ironically, that project turned into Park.io. Mike has built a one person SaaS business. He is currently doing over $150,000 in monthly revenue. And he is a one person company. He has no employees and continues to run the business by himself. Mike says that he just got lucky with Park.io. And there is some truth to that. We all need some luck from time to time with our business. But I do not think it was all just down to luck. And in this interview, I deep-dive into what exactly he did to build that one person SaaS business, how he has dealt with major problems and competitors, and how exactly he is able to run a million dollar company alone.

$6.5M Raised, Zero Traction: A Failed Software Startup Story - Mike Muhney

Mike Muhney, VIP Orbit

$6.5M Raised, Zero Traction: A Failed Software Startup Story

Mike Muhney is the founder and CEO of VIP Orbit, a software company focused on building great contact management products. He launched their flagship product VIP Orbit in 2010 and they raised $6.5 million. Recently, Mike had to shut down the business because he ran out of money and was not getting the traction that he had hoped for. So in this episode, he joins me to talk about the lessons he has learned from a failed software startup. We have a very open and candid conversation about what he thinks led to that failure. Mike was in a similar situation in the 1980s when he co-founded a startup which eventually failed. He had raised $100,000 from an angel investor. He ended up with $15,000 of that money left and needed to give back the money or come up with another idea. And he and his co-founder came up with ACT contact management software, which they went on to sell for $47 million. So Mike is a seasoned entrepreneur who has seen the highs and lows. In this episode, he is willing to talk about the tough parts of being an entrepreneur and what led to his failed software startup.

From 30-Day to 7-Day Free Trial Conversion That Doubled - Janna Bastow

Janna Bastow, ProdPad

From 30-Day to 7-Day Free Trial Conversion That Doubled

Janna Bastow is the co-founder and CEO of ProdPad, a product management tool that helps teams build product roadmaps, prioritize ideas, and organize customer feedback. ProdPad's customers include Disney, Automattic, and eBay. ProdPad was founded in 2012 and has been bootstrapped since day one. The company is based in Brighton in the United Kingdom. Janna is also the co-founder of Mind the Product, an international product community with over 50,000 members and events in 100 cities worldwide. This is a story about two product managers who could not find software to help them do their jobs. Janna showed her co-founder Simon Cast some ideas for a tool, and he offered to build the back end. She handled the front end - built with jQuery and Bootstrap in an era before complex SaaS stacks were standard. They used ProdPad internally for two years before realizing other product managers would pay for it. Janna quit her job first with zero customers. Six months later, they launched a version people could purchase, and their first paying customer signed up within weeks. Growth came organically through blogging about product management topics - how to build roadmaps, write personas, create specs. They ranked at the top of Google for "product management software" because almost nobody else was targeting that keyword yet. ProdPad grew steadily to around $30K MRR, but then hit what Amy Hoy from Freckle called "the plateau of doom." Janna calls 2015 "the year of faffing about" - the team tried AdWords, events, and other unfocused experiments instead of doubling down on what worked. Revenue flatlined for six months. Rather than raise funding, Janna focused the entire company on one metric for three months: free trial conversion rate. They cut trial time from 30 days to 14 (doubling conversions), then to 7 days with gamified extensions for completing key actions. A behavior-based email system recovered 25-30% of users who signed up but did not engage. ProdPad's free trial conversion rate climbed from below industry average to about 10%.

3 Pivots in 3 Years to Get SaaS Customer Discovery Right - Tukan Das

Tukan Das, LeadSift

3 Pivots in 3 Years to Get SaaS Customer Discovery Right

Tukan Das is the co-founder and CEO of LeadSift, a sales intelligence platform that mines publicly available data to help B2B companies identify target accounts showing signals of buying intent. LeadSift was founded in 2012 and raised $1.8 million in funding, including a strategic investment from Salesforce. The company is based in Halifax, Nova Scotia, Canada. This is a story about a couple of data nerds who were playing around with the Twitter and Foursquare APIs one day. They discovered that there was a lot of social media data about people who were looking to buy something. So they decided to build a product and sell these signals to automotive brands. It seemed like a winning idea, but soon they realized it was not. First, they were not solving a customer problem - they were trying to find a market for a cool idea. Second, they did not understand how automotive brands work. Ford is not going to have a salesperson call you because of your tweet. After a year of getting nowhere with five customers, they pivoted to selling audience data for ad targeting. Revenue grew and they landed big brand names, but the business was campaign-driven with no recurring revenue. Their engineering team was demoralized building one-off data requests. With one year of runway left, they made a critical decision. Instead of building another product first, they committed to SaaS customer discovery. They interviewed 80 marketers, discovered the pain point was not with brand marketers but with B2B sales teams, and validated demand with three paying customers before writing any code. They delivered leads manually via spreadsheet for months while gradually automating. Within 17 months of the final pivot, LeadSift had 105 customers including companies like Looker, Vidyard, and Mulesoft, growing 13% month over month and approaching $1M ARR.

Lost $100K Then Built a Bootstrapped SaaS Startup to $500K - David Abrams

David Abrams, Demio

Lost $100K Then Built a Bootstrapped SaaS Startup to $500K

David Abrams and his co-founder spotted a gap in the webinar market. GoToWebinar kept freezing. Google Hangouts was slow. Every webinar campaign required stitching together three or four platforms just to segment attendees and track conversions. They knew they could build something better. The problem was neither founder was technical. They hired a development agency recommended by a consultant, paid almost $100,000 in bulk payments, and stepped away from the process. When they came back to review the work, the product was unusable. The bootstrapped SaaS startup had just burned through six figures and six months with nothing to show for it. Starting over, David used his consulting background in developer hiring to build a real team. The first hire was exceptional and still leads engineering today. But pressure to make up lost time led them to rush the next six hires - five of whom eventually had to be let go. The second critical mistake was skipping the MVP. Demio's original spec was enterprise-level software with dozens of features. It took the team nearly going broke to realize they needed to strip everything down to the essentials - reliable video streaming plus marketing integrations. They launched a free beta, brought in nearly 1,000 users organically through YouTube videos and $5/day Facebook ads, and spent three months collecting feedback. When the bootstrapped SaaS startup's cash hit nearly zero, David launched a seven-day grand opening with 40% affiliate commissions and deeply discounted annual plans. The launch generated enough revenue to fund six more months of operations. By the time of this interview, Demio had grown to $42,000 MRR - about $500,000 in annual run rate - with plans to reach $100K MRR within 12 months.

3 Years to First Customer Then B2B Product-Market Fit - Allan Wille

Allan Wille, Klipfolio

3 Years to First Customer Then B2B Product-Market Fit

Allan Wille and his co-founder Peter launched Klipfolio in 2001 as a downloadable desktop dashboard for tracking soccer scores, weather, and stock prices. The app was wildly popular - 300,000 users and thousands of downloads every day. The problem was zero revenue. For three years, the co-founders did odd jobs and built websites to keep food on the table. Peter even sold his car. Then one day, Lufthansa called. Hundreds of their employees were already using Klipfolio to track soccer scores, and the airline wanted to know if it could display business data instead. That single phone call pivoted Klipfolio from B2C to B2B. But finding B2B product-market fit did not happen overnight. Klipfolio sold expensive on-premise dashboard software to enterprise customers like Intel, American Express, and Staples. The sales cycles were long. Allan cold-called prospects and hated every minute of it. Growth was painfully slow - after 10 years, the company had just 14 employees. The real breakthrough came in 2012 when Klipfolio launched a cloud-based SaaS product at $25 per user per month, targeting small and mid-sized businesses. Allan personally talked to almost every one of the first 1,000 customers to understand what they needed. That is when B2B product-market fit clicked and the hockey stick appeared. By the time of this interview, Klipfolio had 90 employees, 8,500 customers, and was approaching $8 million in ARR. The company had raised $16 million from investors, with customers including Jet.com, Zendesk, and IKEA.

SaaS Content Marketing That Reached 100K Users for Free - Raj Bhaskar

Raj Bhaskar, Hurdlr

SaaS Content Marketing That Reached 100K Users for Free

Raj Bhaskar is the co-founder and CEO of Hurdlr, a mobile app for freelancers, Uber drivers, Airbnb hosts, and independent workers to manage their business finances in real time. Before Hurdlr, Raj built and sold VisualHOMES, a financial management platform for affordable housing agencies that processed $200 million in monthly rental payments and managed half a million housing units. The company was acquired by Yardi after 10 years. With Hurdlr, Raj initially planned to build a mobile accounting system. He gave the prototype to 25 entrepreneur friends, learned that solopreneurs were the sweet spot, and then discovered that Uber drivers and Airbnb hosts had the exact same tax tracking problem. That insight shaped the product into a multi-vertical financial tool with a shared profit and tax engine. Growth came through SaaS content marketing. Raj's head of growth created a blog post on the top 16 tax deductions for Uber drivers, then personally befriended every admin of Uber-related Facebook groups and Reddit communities. He got all of them to pin the post during the same two-week window, driving 3,000 signups. A follow-up 20-page tax planning guide brought another 5,000. From those 8,000, Raj selected 200 early users to test the app. Raj also shares why he insisted on automated expense tracking over an MVP, how Hurdlr monetizes through API partnerships with companies like H&R Block, and how SaaS content marketing distribution matters more than content creation.

Our SaaS Content Strategy Got 1,000 Customers With No Ads - James Gill

James Gill, GoSquared

Our SaaS Content Strategy Got 1,000 Customers With No Ads

James Gill is the co-founder and CEO of GoSquared, an all-in-one platform that combines analytics, live chat, and CRM. The three co-founders started the company when they were just 14 years old, originally trying to build an online advertising network after watching Mad Men. The advertising business failed - they could not even pay for school lunch. But publishers using their ad network loved the beautifully designed analytics dashboard they had built as a backend tool. When Smashing Magazine tweeted about the real-time visitor stats feature, so many people signed up that it crashed GoSquared's servers. That was the signal to pivot. Ten years later, GoSquared has over 1,000 paying customers ranging from small startups to JP Morgan and US government agencies, with a team of just 10 people. Nearly all of that growth came from SaaS content strategy - free design resources, CSS cheat sheets, London Olympics infographics, and real-time global metrics pages that journalists reference worldwide. James shares why he spent a ridiculous amount of engineering effort on a radar-screen onboarding animation, how a quick Slack integration became one of their biggest growth drivers, and why building three products instead of one actually makes sense when you define focus as solving one problem set rather than building one category of software.

Building Enterprise SaaS Features That Win Big Deals - Grant Miller

Grant Miller, Replicated

Building Enterprise SaaS Features That Win Big Deals

Grant Miller is the co-founder of Replicated, a platform that makes it easier for SaaS businesses to deploy their product into corporate data centers and the private cloud. Previously, he co-founded Look IO, a mobile live-chat platform that was acquired by LivePerson just nine months after launch for several million dollars. He and his co-founder, Marc Campbell, raised $6.5 million for Replicated, including a $5 million Series A from Amplify Partners. In just 18 months, Replicated grew to serve over 400 enterprise IT organizations, including 20 Fortune 100 companies, with about 30 SaaS applications distributing through the platform. Grant also created EnterpriseReady.io, an open-source guide for building enterprise SaaS features like single sign-on, role-based access control, audit logging, and compliance. He spent a year writing the guide on nights and weekends, turning it into a resource that helps SaaS founders understand exactly what enterprise buyers expect. In this conversation, Grant shares why targeting the biggest SaaS companies was a mistake early on, how Replicated's business model works by taking 5-10% of each enterprise license sold through the platform, and what he learned about empathy for enterprise buyers after his first acquisition.

Solo Founder Built a Vertical SaaS to $2M ARR - Bruno Didier

Bruno Didier, Trackin

Solo Founder Built a Vertical SaaS to $2M ARR

Bruno Didier is the founder and CEO of Y Combinator startup Trackin. The company provides a vertical SaaS solution to help restaurants get better control of their deliveries by connecting managers, drivers, and customers. Trackin offers an online ordering system, a manager dashboard, a driver app, and real-time delivery tracking. The company was founded in 2014, has raised $400K, and is based in San Francisco. Before Trackin, Bruno was the CTO of a catering company where he experienced firsthand how chaotic food delivery management was. Restaurants had no idea where their drivers were, could not tell customers when food would arrive, and relied on paper maps taped to kitchen walls to define delivery zones. Bruno left San Francisco for France to build the product, won a national contest that provided his first $25K, and then went door to door to every restaurant in his city - not to sell, but to ask managers for help building the right vertical SaaS product. By framing himself as a student seeking advice rather than a salesperson, he built relationships that turned into his first paying customers without ever making a sales pitch. A chance dinner with Twitch co-founder Michael Seibel in Lyon changed everything. Seibel told Bruno he should apply to Y Combinator - something Bruno had never considered because it seemed too ambitious. He got in, and YC taught him to widen his sales funnel through email newsletters to prospects that shared new features and industry advice. Some leads received the newsletter for six months before a single feature triggered them to sign up. Bruno also built a second product, MobyDish, a catering marketplace that became his own customer for the vertical SaaS platform, helping him improve Trackin faster than external feedback alone.

Signs You Chose the Wrong SaaS Co-Founder - Claudiu Murariu

Claudiu Murariu, InnerTrends

Signs You Chose the Wrong SaaS Co-Founder

Claudiu Murariu is the founder and CEO of InnerTrends, a growth analytics platform for SaaS and web products. InnerTrends uses data science to help companies understand their user onboarding process and convert more first-time users into customers. The company was founded in 2015 and is based in Romania. Before InnerTrends, Claudiu built PadiCode, a behavioral targeting product that reached $300K in annual revenue with just three employees. The company attracted major clients including Adidas, Reebok, and Vodafone, largely through clever integration partnerships with email platforms like Campaign Monitor and AWeber. But a SaaS co-founder conflict nearly destroyed everything. Claudiu and his partner had fundamentally different visions for the business - he wanted to grow it, while his partner wanted to build something she could exit from without being needed. They avoided the hard conversations until the conflict exploded, and Claudiu left as a passive shareholder. When he started InnerTrends, Claudiu made two deliberate changes based on the SaaS co-founder lessons he had learned. First, he brought on investors to serve as external mediators who could catch problems early. Second, he chose co-founders based on skills they had now, not skills they might develop later. The product journey was equally instructive. InnerTrends started by trying to answer any analytics question, but user testing revealed nobody could even formulate a question. After scrapping months of work, Claudiu narrowed the focus to user onboarding - solving one problem deeply rather than many problems superficially. That pivot led to 10 paying customers within months of the public launch.

A 12x SaaS Pricing Increase That Fixed Unit Economics - Antonio Carlos Soares

Antonio Carlos Soares, RunRun.it

A 12x SaaS Pricing Increase That Fixed Unit Economics

Antonio Carlos Soares is a serial entrepreneur from Sao Paulo, Brazil. He quit a successful consulting career at Monitor to build startups, put his mother's apartment up as collateral for a business loan, and grew his second company to $20M in revenue before selling it to a media conglomerate. His third company, RunRun.it, started as a pet project built by his co-founder Franklin to manage internal chaos at their previous company. Before they even launched, 60 companies were already using the tool for free. That early traction convinced them to turn it into a real business. But the SaaS pricing was fundamentally broken. At just $6.50 per user per month, the unit economics made no sense. Antonio realized he would need 200,000 customers to build a $100M company at that price point. So he made a series of bold moves - raising prices 12 times over, switching from freemium to a 14-day trial, and building an inside sales team to drive conversions. The results were dramatic. RunRun.it achieved negative net revenue churn because upsells on the new SaaS pricing more than offset cancellations at the old price. But the brand took a hit - for the first time, early adopters felt betrayed by the price changes. Antonio shares the hard-earned lessons about capital structure, freemium traps, and why getting your SaaS pricing right early matters more than growing your user base.

This Vertical SaaS Replaced a 120-Year-Old Eye Exam - Aaron Dallek

Aaron Dallek, Opternative

This Vertical SaaS Replaced a 120-Year-Old Eye Exam

Aaron Dallek is a serial entrepreneur who started his first business at 14. His co-founder, Dr. Steven Lee, was an optometrist who had performed 20,000 refractions when a patient asked a simple question: "Why can't we do this at home?" That question became the foundation for Opternative, a vertical SaaS that fundamentally changed how eye exams work. The two co-founders self-funded the initial proof of concept, then spent two and a half years building and validating a technology that uses a computer screen and smartphone to identify refractive error - no lenses required. They ran 1,500 refractions comparing their digital method against traditional exams and proved statistical equivalency in a clinical trial. Opternative grew to over 100,000 signups, partnered with 1-800 Contacts, and raised $9.5 million across seed and Series A rounds. The product charges $40 for a glasses prescription and $60 for both glasses and contacts, with a refund rate of just 0.06%. But building a vertical SaaS in healthcare comes with unique obstacles. While the ophthalmology community supported the technology, optometry trade groups pushed legislation in multiple states trying to ban or restrict online eye exams. Aaron shares how Opternative navigated regulatory pushback, why everything takes longer than you expect, and how tenacity from overcoming a childhood learning disability shaped his approach to entrepreneurship.

500 Posts to 7,000 Customers: SaaS Content Marketing - Garrett Moon

Garrett Moon, CoSchedule

500 Posts to 7,000 Customers: SaaS Content Marketing

Garrett Moon is the CEO and co-founder of CoSchedule, a content marketing and social media publishing calendar for small businesses and marketing teams. CoSchedule helps over 7,000 customers organize their content marketing and social media publishing in more than 100 countries around the world. CoSchedule was founded in 2013 and to date has raised around $500,000 in funding. This episode is the story of two guys who ran a web design and marketing consulting business. One day they hatched a plan for a new SaaS product on a plane ride between North Dakota and Atlanta. By the time they landed, they were fully committed to the idea and had decided what they were going to do next. This wasn't the first time these two had launched a product. They had already tried four times without much success. But this time felt different because their idea would solve a problem their consulting clients were often complaining about - organizing content creation and social media promotion in one place. They started by writing a blog post about the problem and how their new product would solve it. They mocked up some screenshots in Photoshop of a product that didn't exist yet. Within 24 hours, they had 300-400 email signups from people interested in the idea. Then Garrett did something remarkably disciplined. He went through that email list, threw out all the Gmail and Yahoo addresses, and identified 10 potential customers. He created a slide deck and scheduled calls with each of them to get feedback before writing any code. The SaaS content marketing didn't stop there. Garrett blogged once a week about the entire process of building CoSchedule - sharing wireframes, early ideas, and getting community feedback along the way. After launch, they scaled to three posts per week, published over 500 actionable blog posts, and grew their email list to over 100,000 subscribers. What makes this story different from every other "we used content marketing" narrative is Garrett's Blue Ocean strategy. Instead of competing on volume, CoSchedule published fewer but dramatically better posts - several thousand words each, deeply researched, always actionable, and always including downloadable worksheets or resources. Most competitors wouldn't put in that level of effort. That became their moat. Garrett also shares the painful lessons about building features customers didn't want, why he deliberately avoided selling to his consulting clients, and why focus is the single most important attribute for any entrepreneur.

SaaS Product Validation With Zero Code and 9 Doctors - Luke Kervin

Luke Kervin, PatientPop

SaaS Product Validation With Zero Code and 9 Doctors

Luke Kervin is the founder and co-CEO of PatientPop, an all-in-one practice growth platform for healthcare providers. The company was founded in 2014 and has raised around $24 million to date. Prior to launching PatientPop, Luke co-founded two companies that both had successful exits and were acquired. The PatientPop story starts in a doctor's office. Luke's wife was pregnant, and he started noticing how uncoordinated the healthcare experience was. He had an idea for a product to fix that problem - but when he went out to interview doctors, they told him flat out they weren't interested. Most founders would have stopped there. But Luke kept asking questions. He started hearing the same thing over and over: doctors were struggling to survive as independent practices. They knew their front door was moving online, but they had no idea how to manage their web presence. They were cobbling together five or six different vendors and had no way to measure what was actually working. That's when Luke realized his experience building e-commerce marketing technology could solve a massive problem in healthcare. He and his co-founder Travis Schneider created business cards for a company called "Patient Tap," built a one-page landing page, and went out to pitch doctors on a product that didn't exist yet. The first nine doctors they pitched all signed up at $400-$500 per month. With SaaS product validation complete in under two weeks, Luke moved to the next phase: proving the product could deliver results. They cobbled together a manual solution and drove an average of 21 new patients to each practice in the first 30 days. That was enough to raise capital and start scaling. Two years later, PatientPop had 142 employees, a field sales team closing at 30%+ rates, and four different sales channels driving growth. Luke shares the specific tactics they used, the mistakes they made trying to move upmarket too fast, and why spending time sitting in front of customers was the best advice he could give any founder.

Dropout to 7-Figure SaaS With an Entrepreneurial Mindset - Shane Melaugh

Shane Melaugh, Thrive Themes

Dropout to 7-Figure SaaS With an Entrepreneurial Mindset

Shane Melaugh was the opposite of a model student. He barely made it through school, dropped out of university, and spent two years unable to find a single job. His early business attempts - from coaching people on presentations to building and selling computers on eBay - all crashed into the same wall: he had no idea how to find customers. Then something unexpected happened. Shane got obsessed with water cooling PC components. He started writing detailed reviews, and within a year he went from knowing nothing to being a recognized authority in the niche. That experience revealed the entrepreneurial mindset that would later fuel Thrive Themes. But the path from that insight to a 7-figure SaaS business was anything but smooth. Shane signed a terrible contract with a parts distributor, worked essentially for free for two years, and hit financial rock bottom. Through it all, he realized the missing piece was always marketing - and he decided to apply the same obsessive learning method to building a real business. Today, Thrive Themes has over 30,000 customers and 35 employees. Shane built it by spending five years developing an audience before ever launching a product. In this third and final part of the interview, Shane shares the personal journey and the entrepreneurial mindset shifts that made the difference between giving up and building something remarkable.

How a Failed $80K Product Became a Self-Funded SaaS - Jay Gibb

Jay Gibb, CloudSponge

How a Failed $80K Product Became a Self-Funded SaaS

Jay Gibb is the co-founder and CEO of CloudSponge, a product that helps businesses acquire more users through their email referral forms. Instead of asking people to type in email addresses manually, CloudSponge gives users access to their contacts directly from the website. The company was founded in 2010 and is completely self-funded. Its customers include Lyft, Yelp, and Airbnb. CloudSponge runs at about $500,000 in annual revenue and has been profitable since 2011. But the road to building this self-funded SaaS was anything but straightforward. Jay originally set aside $100,000 to build a cloud backup product called CloudCopy. After spending about $80,000 over nearly a year, the team realized they were nowhere near a product ready for market. During that process, they had built a contact importing feature that turned out to be the hardest technical challenge - and they noticed hundreds of developers on Stack Overflow and Quora asking the exact same questions they were solving. So Jay made the call to pivot. Within a week, the team had a website up with a price tag on their contact importing tool. Developers started paying on day one because they had already seen the pain and knew CloudSponge solved a real problem. In this conversation, Jay talks about building a self-funded SaaS from the ashes of a failed product, why charging from day one gave him critical validation, and the counterintuitive decision to add friction to his onboarding process that dramatically improved conversion rates. He also shares why developers should buy before they build and how "Powered by CloudSponge" became a scalable distribution channel.

From Evernote Idea to SaaS Product-Market Fit - Zvi Band

Zvi Band, Contactually

From Evernote Idea to SaaS Product-Market Fit

Zvi Band is the co-founder and CEO of Contactually, a CRM tool that helps professionals stay engaged with their most important relationships. He founded Contactually in 2011 after writing down an idea for a "proactive CRM" in Evernote. What started as a weekend prototype built by one of his engineers grew into a company with over 70 employees and more than $12 million in venture funding. The company is based in Washington, D.C., and generates several million dollars in annual revenue on its way toward $10 million ARR. Zvi's path to SaaS product-market fit was anything but smooth. The first product version sent annoying emails asking users to categorize every new contact - people hated it. The second version reminded users to follow up with everyone, including people they did not care about. It was only after multiple rounds of customer development that the team discovered the key insight: users wanted to segment their relationships into buckets and only stay in touch with the people who mattered most. Before going full time on Contactually, Zvi ran a consulting firm and treated the product as a side project. When 500 Startups offered $50K to join their accelerator, it became a burn-the-boats moment - Zvi shut down his consulting business and his co-founder quit his job at Microsoft. In this conversation, Zvi talks about how he validated demand using lean pricing tests before charging customers, why SaaS product-market fit came from listening to user complaints rather than building more features, and the one thing he wishes he had done differently from day one.

How a Website Metric Sparked a SaaS Go-to-Market Shift - Kreg Peeler

Kreg Peeler, SpinGo

How a Website Metric Sparked a SaaS Go-to-Market Shift

Kreg Peeler's first entrepreneurial venture was at age 12 - selling avocados at a busy California intersection with a cardboard sign. His SaaS go-to-market journey started in a similarly scrappy way, with a DVD containing 6,000 menus that he distributed through university bookstores. That DVD led to a website called Spin Local, which had a local events section. Kreg's wife Amanda manually curated event listings - digging up content from venue websites, correcting typos, and publishing comprehensive calendars. When they checked their analytics, 80% of all website traffic was going to that events section. That one metric changed everything. When newspaper companies tried to acquire Spin Local, Kreg countered with a licensing deal instead. He broke off the events section as a separate product called SpinGo and signed up media companies as clients who paid monthly fees for event content they could embed in their entertainment sections. SpinGo's SaaS go-to-market strategy evolved through three phases. Phase one was licensing event content to media companies and app developers. Phase two was promotions - letting event makers pay for premium placement, featured listings, and self-serve Facebook and Google ad campaigns. Phase three was Event Master, a full SaaS platform that unifies ticketing, marketing, volunteer management, and event apps into one solution. By 2016, SpinGo had grown to 200,000 registered event makers, powered 5,500 entertainment apps reaching 200 million monthly viewers, and raised over $7 million in funding. The Event Master SaaS product, launched in February, signed 254 events in its first few months and was projected to generate 80% of the company's revenue. Kreg's trade show strategy was particularly effective. He brought professional stage lighting, 80-inch TVs, and event production expertise to newspaper industry conferences where competitors showed up with pop-up banners. The visual contrast won attention, and his message - "own local, don't try to be national" - positioned SpinGo as an ally rather than a competitor.

From a Failed Startup to SaaS Product-Market Fit - Zal Dastur

Zal Dastur, Lucep

From a Failed Startup to SaaS Product-Market Fit

Zal Dastur got the call that changed his career while he was out at a bar with friends. His future co-founder Kaish asked three questions: Do you enjoy what you're doing? No. Do you see it going anywhere? No. What are you doing with your life? Not much. Then Kaish said: Come to India and help me build a startup. You have one hour to decide. The next day, Zal resigned. One month later, he was on a flight to Bangalore. That first startup - a lead generation platform for hotel meeting venues - ran out of money after two years. They approached Sequoia and Accel Partners, got rejected, and assumed that meant nobody would fund them. Years later, they learned they were the first startup to get a company-wide agreement with Taj Hotels, India's largest hotel chain. But that failure taught Zal and Kaish the cash flow discipline they needed for their second startup. When they launched Lucep in 2014, they used revenue from a customer engagement platform they had previously sold to large enterprises to fund development, avoiding the fundraising trap entirely. Lucep's path to SaaS product-market fit started with a simple test. Zal set a goal of 30 beta signups - and got 100. He started charging $1 per user in January, $2 in February, and full price by March. The product's value was undeniable: companies responding to leads within 5-10 minutes instead of 24-48 hours saw dramatic conversion improvements. Research shows that waiting more than 5 minutes drops lead contact rates by 21x. Zal is refreshingly honest about the mistakes he made along the way - from not setting up a proper shareholder agreement to leading by committee with three co-founders. His advice to new founders: sort out the boring legal documents when things are good, because when things go bad, it becomes impossible.

One Phone Call Revealed SaaS Product-Market Fit - Ryan McKay-Fleming

Ryan McKay-Fleming, Chalk.com

One Phone Call Revealed SaaS Product-Market Fit

Ryan McKay-Fleming is the co-founder and CTO of Chalk.com, a SaaS product that helps teachers with lesson planning, grading, assessment, and attendance. Over 100,000 teachers worldwide are using Chalk.com. The company is based in Toronto, Canada, was founded in 2012, and has raised $500K in its initial seed round. Ryan and his co-founder William met at the University of Waterloo and decided to build a product for teachers on a hunch. They did not do any validation, never talked to teachers, and built the first version at Ryan's kitchen table. As you might expect, things did not go as planned. After launching, they charged teachers $30 per year and made about $3,000 total in their first year. They were discouraged. Then a school in Texas reached out wanting 72 licenses in 24 hours. That was the SaaS product-market fit breakthrough - the buyers with money were schools and districts, not individual teachers. They made the product free for individual teachers to drive adoption, then sold premium collaboration and curriculum management features to schools. The episode covers the lessons of building without validation, selling into education's long seasonal sales cycles, and why domain knowledge finds you when you need it.

The SaaS Go-to-Market That Scaled to 124K Websites - B Byrne

B Byrne, Clef

The SaaS Go-to-Market That Scaled to 124K Websites

B Byrne is the co-founder and CEO of Clef, a service that replaced passwords with secure phone-based two-factor authentication. Hold up your phone in front of any computer, and Clef logs you in instantly using the same cryptography that developers have trusted for decades. The idea came when LinkedIn was hacked in 2012 and over 6.5 million passwords were stolen. B was at Adobe at the time, building demos around mobile identity. He kept waiting for Apple to let phones replace passwords - and when it did not happen, he decided to build it himself with two college friends. The biggest challenge was a classic two-sided marketplace problem. Websites would not add Clef without existing users, and users could not benefit without websites supporting it. The SaaS go-to-market strategy B chose was counterintuitive - instead of going broad, he went deep into small communities, getting Clef onto clusters of websites that shared the same user base. That way, each user could log in with Clef on five sites they used every day, creating real daily value rather than a novelty. A manufactured PR stunt called the "Petition Against Passwords" got reporters at the New York Times interested. When the Times published a glowing review calling the product "magical," it did not drive immediate signups - but it gave Clef the credibility that security products need to earn trust. Within a month, the snowball started rolling through word of mouth. B also talks about writing and open-sourcing the company's employee handbook, why he thinks HR is the most overlooked function at startups, and what he has learned about building culture as a first-time founder at 24 years old.

How a Self-Funded SaaS Hit 8 Figures After Nearly Dying - Aaron Fulkerson

Aaron Fulkerson, MindTouch

How a Self-Funded SaaS Hit 8 Figures After Nearly Dying

Aaron Fulkerson is the co-founder and CEO of MindTouch, a knowledge management platform that powers help centers and self-service support for companies like PayPal, Docker, Zenefits, Whirlpool, and Remington. Aaron and his co-founder Steve left Microsoft to start MindTouch as an open source project in 2005. Within two years, the project ranked in the top 5 on Sourceforge with over 2,000 downloads a day. They commercialized with support subscriptions and grew to $2.3 million in cash receipts by 2009. But the self-funded SaaS was in trouble. With hundreds of well-funded competitors, no defensible moat, terrible churn, and no venture capital available during the 2008 financial crisis, the business was driving off a cliff. Aaron made the hard call to cut 40% of headcount, deprecate the on-premise product, and rebuild as a cloud-only platform focused exclusively on customer self-service content. The pivot nearly failed. From 2010 to 2013, MindTouch funded the new product using $6.2 million from the legacy business while simultaneously building the cloud platform. By 2012, the new business took off - growing from zero to over $10 million ARR in three years. In 2014, MindTouch outperformed the top SaaS companies by one to two standard deviations across every key metric tracked by Bessemer Venture Partners. Aaron shares what kept him going through the hardest years, the three principles that turned the company around, and why grit matters more than any other trait for entrepreneurs.

10 Founders Share Their Best SaaS Growth Advice - Omer Khan

Omer Khan

10 Founders Share Their Best SaaS Growth Advice

For the 100th episode of The SaaS Podcast, Omer Khan skips the guest interview and goes solo. Instead of bringing on another founder, he went through all 99 previous episodes and pulled out the 10 best pieces of SaaS growth advice - the ones that go beyond generic "work hard" and "be persistent" to something more specific and actionable. The advice comes from founders who built real businesses: Dan Norris launched WP Curve in seven days after years of failure. Wade Foster co-founded Zapier with the mindset of making today better than yesterday. Rob Walling built Drip while refusing to let anyone else set the agenda for his life. Peter Coppinger bootstrapped Teamwork to $14 million by thinking bigger than the Irish market. Omer covers 10 lessons spanning SaaS growth mindset, from Paul Graham's "do things that don't scale" to Steli Efti's reminder that all advice is "limited life experience and overgeneralization." He connects each piece of advice to real founder stories from the podcast, including Tom Leung's eight pivots before finding product-market fit in one week, Trevor Owens' warning about making decisions solely for money, and Andrew Wilkinson's adaptation of Richard Branson's "screw it, let's do it" philosophy. The episode closes with Omer's personal lesson: trust your gut. After leaving a comfortable six-figure corporate job to pursue his own dreams, he stopped relying on other people's advice as a crutch and started listening to his own voice more. It is both a reflection on 100 episodes and a practical SaaS growth playbook drawn from the founders who have been on the show.

8 Failed Pivots Then Finding Product-Market Fit in 1 Week - Tom Leung

Tom Leung, Anthology

8 Failed Pivots Then Finding Product-Market Fit in 1 Week

Tom Leung is the co-founder and CEO of Anthology, a Seattle-based startup formerly known as Poachable. The platform enables employed tech professionals to explore new career opportunities anonymously, and companies like Amazon, Microsoft, Netflix, Dropbox, and Facebook recruit through it. The company has raised around $1.8 million. Before finding product-market fit with Anthology, Tom and his co-founder spent two years building Yabli, a consumer Q&A site for product purchasing decisions. They raised $1.5 million in angel funding, but the business never took off. Tom now believes the problem was not big enough - people don't lose sleep over picking the wrong coffee maker - and the solution was only incrementally better than reading Amazon reviews. When investors stopped funding Yabli, the team had two choices: sell the company or try a Hail Mary. They chose to pivot rapidly, spending about a month on each experiment. They tried white-labeling Yabli as enterprise software, building an AMA platform, creating a social polling app, and several other ideas. None broke through. After the eighth failure, the team was ready to accept an acquisition offer. Then Tom's team built a one-page HTML landing page for Poachable. No secure form, no algorithm, no product - just a form that emailed Tom the submissions. They set a bar: if they couldn't get five friends to fill it out, they would stop. Instead, a local tech blog saw the tweet, wrote a story, and signups flooded in. People were giving up sensitive salary and career information on a form with no SSL certificate - proof that finding product-market fit means solving a problem people actually care about. The deal to sell the company was called off within a week. Tom talks about the difference between tenacity and blind faith, why adding 20 features won't save a bad idea, and the moment he realized his team had been "really good at executing bad ideas" for two years.

Launching a Marketplace for Algorithms With 14K Devs - Diego Oppenheimer

Diego Oppenheimer, Algorithmia

Launching a Marketplace for Algorithms With 14K Devs

Diego Oppenheimer is the co-founder and CEO of Algorithmia, a Seattle-based marketplace that connects academics building algorithms with app developers who need them. The company was founded in 2013 and raised $2.5 million in funding. The idea of launching a marketplace for algorithms started during a backpacking trip through Australia and New Zealand in 2008. Diego and his co-founder Kenny Daniel had been friends since college, and they spent months in a tent with a notebook and laptop, mapping out what a computation marketplace could look like. It took another five years of refining the concept before they launched. The real validation came from Diego's time at Microsoft. While building features for Excel, his team needed an advanced algorithm. After months of searching Microsoft Research - a $7 billion operation - he found that the exact algorithm he needed had already been built and was sitting inside Excel. Nobody knew. That failure to connect research with product teams, even inside one of the best companies in the world, confirmed that launching a marketplace to bridge that gap was a real opportunity. When it came time to raise money, Diego used his Excel skills to build a spreadsheet rating 60 investors by fit, location, interest, and portfolio overlap. Then he flipped the list and started pitching from the bottom - worst fit first. The logic: his pitch would be terrible early on, so he would learn from the investors least likely to fund him. By the time he reached the top of the list, he had answers to every hard question. The strategy worked, and they closed $2.5 million. Today Algorithmia has a team of nine, over 14,000 developers on the platform, and partnerships with universities. Diego talks about doing things that don't scale in the early days, the shift from internal product building to external evangelism, and the biggest lesson he learned transitioning from a company like Microsoft to startup speed.

Finding Product-Market Fit With $15K Left and a Napkin - Mike Muhney

Mike Muhney, VIPOrbit

Finding Product-Market Fit With $15K Left and a Napkin

Mike Muhney is the co-founder and CEO of VIPOrbit Software, a company focused on building great contact management products. Their flagship product, Vipor CRM, is available on iOS and Mac platforms. The company was founded in 2010 and has raised over $4 million in funding. In 1986, Mike co-founded a software business that eventually failed. With only $15,000 remaining from an angel investment of $100,000, he and his co-founder had a choice: close down or come up with another idea. A mentor suggested a brainstorm breakfast, and over four hours they sketched the menu structure for what would become ACT! Contact Management Software on a napkin. That moment of finding product-market fit changed everything. They built a product they needed themselves - a digital version of the paper Daytimer organizer with seamless integration between contacts, activities, and notes. ACT! went on to create an entirely new software category. Mike became a celebrity in the tech industry, speaking at major conferences worldwide. Seven years after that brainstorm breakfast, they sold ACT! for $47 million. Mike walked away with just under $5 million from his 10% stake. But the story after the exit is equally revealing. Mike struggled with a sense of emptiness and fading relevance. He launched Celebrity Soft, signing Michael Jordan and Charles Barkley for a fantasy golf game - only to have Jordan pull out without explanation, collapsing the entire venture. He spent years at Deloitte Consulting and SalesLogix before the itch to build his own thing returned. In 2009, sitting in his home office reading a BusinessWeek article about the app economy, Mike had his second finding product-market fit moment. He realized the CRM industry had reached fewer than 14 million users worldwide despite billions of smartphone owners. He started VIPOrbit Software to build the contact management tool he still needed himself - the same motivation that produced ACT! decades earlier. Mike is also candid about the fear that accompanies entrepreneurship at every stage. He describes the "front office" enthusiasm that entrepreneurs project versus the "back office" fear of running out of money, not being discovered, and watching time run out.

Selling a SaaS Business for $8M Then Starting Over - Nick Kellet

Nick Kellet, Listly

Selling a SaaS Business for $8M Then Starting Over

Nick Kellet is the co-founder of Listly, a product that helps bloggers and publishers engage their audience with continuously evolving lists. According to Listly, 30% of all content on the web is built around lists - but these lists quickly get stale and do not do much to engage readers. Before Listly, Nick built a data visualization tool called AnswerSets that used Venn diagrams for database queries. He took the product from prototype to acquisition in just two and a half years, selling a SaaS business to Business Objects (now SAP) for over $8 million. The strategy was simple but effective - he exhibited at the Business Objects user conference when the product was only six weeks old and caught the attention of both enterprise customers and the company's CTO. After selling a SaaS business and spending six years at Business Objects, Nick did something nobody expected. He created a physical board game called Gift Trap, inspired by his daughter asking how Father Christmas decides what gifts to give people. He ordered 10,000 games without knowing anything about the toys and games industry, play-tested with over 500 people, and built traction through blogger outreach. Gift Trap has now sold nearly 100,000 copies in 12 languages and won over 20 awards. With Listly, Nick applied lessons from both experiences. He found early traction through an unexpected niche - a church conference organizer who used Listly to crowdsource speakers. That single use case created a domino effect of reviews and adoption. Nick also shares why he deliberately understated Listly's value proposition, focusing on personal utility rather than network effects, because promising engagement multiplication to users with zero existing traffic meant promising 100 times zero.

Finding Product-Market Fit When an Industry Says No - Benji Rogers

Benji Rogers, PledgeMusic

Finding Product-Market Fit When an Industry Says No

Benji Rogers is a musician from London who had been making his own records since 1999. When he came up with the idea for PledgeMusic at 2:30 in the morning, he was sleeping on an air mattress at his mother's house. His wife was working as a receptionist to support them. He had almost no money left. The idea was simple but radical - let artists pre-sell the experience of making an album to their biggest fans in real time. Instead of earning $9.99 per CD sale, artists on PledgeMusic averaged $55 per transaction because fans were buying the journey, not just the finished product. Benji saw immediately that this solved a problem he had lived with for years as an independent musician. But finding product-market fit in the music industry proved far harder than he expected. For three months while his team coded the site, Benji could not find a single payment processor willing to handle reference transactions. Every bank, credit card company, and processor said no. They had never heard of crowdfunding. They did not understand pre-authorization payments. At one point, the team considered shutting down and returning investor money. Then their accountant's friend ran a credit card processing company. Two days later, the first test transactions went through. Benji framed the email - the subject line read, "This is what success looks like." The industry resistance did not stop there. Every major record label said no. Every major management company said no. Most artists said no. Benji had expected to launch and see rapid adoption. Instead, finding product-market fit took years of persistence in an industry he describes as technologically on par with the Amish. Six years later, PledgeMusic had over 50 employees, offices around the world, and had released more than 1,000 albums. Benji was named to Billboard's 40 Under 40 and won Digital Executive of the Year. The artists and labels that originally said no eventually became customers.

The SaaS Marketplace That Sold to Autodesk in 16 Months - Aaron Epstein

Aaron Epstein, Creative Market

The SaaS Marketplace That Sold to Autodesk in 16 Months

Aaron Epstein's first product was ColorSchemer, a color-picking tool he built during spring break in his college dorm room in 1999. He grew it into a six-figure-a-year business and ran it solo for six years. The business was so automated that Aaron got bored. That boredom led him to merge with co-founders who had built COLOURlovers, a creative community with over a million registered users. Together they went through Y Combinator in 2010. But investors were not excited about a color data business. Aaron and his team tried pitching a crowdsourced color trend platform - a competitor to Pantone - but the market felt too small. Then MetLife reached out and paid $250 to license a pattern that a community member had created just for fun. That single transaction changed everything. The team realized the SaaS marketplace opportunity was far bigger than color data. They raised $1 million, but quickly discovered that building a marketplace on top of COLOURlovers was not the right approach. The scope was much bigger than palettes and patterns - it included fonts, Photoshop files, website themes, and stock photos. So they made the painful decision to abandon their million-user community and launch Creative Market as a separate brand starting from zero. They raised another million dollars, launched the full SaaS marketplace in October 2012, and grew 20% month over month from day one. In October 2013, two acquisition offers arrived on the exact same day - one from a company that wanted to gut the team, and one from Autodesk that aligned perfectly with their culture and vision. Aaron chose Autodesk. The deal closed in February 2014. What looked like a 16-month overnight success was actually 15 years of building, pivoting, and trading up from one opportunity to the next.

How Startup Traction Starts With 20 People You Know - Scott Klein

Scott Klein, StatusPage.io

How Startup Traction Starts With 20 People You Know

When Scott Klein and his brother Steve were doing contract work, they kept running into the same problem - companies had no way to communicate operational status to their customers. Status pages existed at places like GitHub and Heroku, but nobody had turned it into a product. So they started building StatusPage.io part-time in October 2012. By February 2013, they had their first paying customer. The early days were anything but certain. People emailed them saying the product was something anyone could build in a weekend and they would never pay for it. But Scott and his team had something most developer duos do not - a third co-founder named Danny who spent most of his days on the phone with customers. Danny's job was not to code. It was to listen, follow up, and figure out whether StatusPage was solving a real problem. Scott credits the vast majority of their startup traction to having someone like Danny around. The first 20 customers were people Scott knew personally from the developer community. He had told them what he was working on long before launch. When the product was ready, selling was easy because these were not cold leads - they were people who already trusted the team. Before StatusPage, Scott and Steve had built a product in the music industry. Scott admits they had no business being in that market. They did not go to shows, they were not musicians, and they could not empathize with the customers they were trying to serve. That experience taught him that the best customer development starts with yourself - build something that would make your own life better, and validation becomes intuitive. StatusPage.io went on to raise $250,000, land customers like Visa, Vimeo, and KISSmetrics, and eventually get acquired by Atlassian.

Building Multiple Businesses While Working 5 Hours a Day - Andrew Wilkinson

Andrew Wilkinson, Metalab

Building Multiple Businesses While Working 5 Hours a Day

This is Part 2 of the interview with Andrew Wilkinson. Andrew is the founder of Metalab, Flow, Pixel Union, and Ballpark. He has built multiple businesses into multi-million dollar operations by the age of 30, all while bootstrapping and working unconventional hours. In this episode, Andrew talks about how he got the idea for Flow, his task management SaaS product, and the strategic misfire of initially targeting consumers instead of business teams. He describes building multiple businesses by hiring great people who handle the follow-through while he focuses on starting new things. Andrew also opens up about his philosophy of working smarter rather than harder. He wakes up in the early afternoon, works five or six hours, never works weekends, and gets eight hours of sleep every night. Despite pushback from startup culture that glorifies sleep deprivation, Andrew argues that building multiple businesses requires protecting your energy and focusing on high-output work. The conversation also covers his failed ventures, including a designer cat furniture store that lost him $20,000 to $30,000, and why he learned to focus only on opportunities where he has a genuine advantage when building multiple businesses.

9 Subscription Models That Unlock SaaS Monetization in Any Industry - John Warrillow

John Warrillow, The Value Builder System

9 Subscription Models That Unlock SaaS Monetization in Any Industry

John Warrillow is the founder of The Value Builder System, a company that helps business owners improve the value of their company. Prior to starting The Value Builder System, John started and exited four companies, including a market research business that was acquired in 2008. John is the author of the bestselling book Built to Sell, which was recognized by both Fortune and Inc Magazine as one of the best business books of 2011. His latest book, The Automatic Customer: Creating a Subscription Business in Any Industry, explores how SaaS monetization principles can be applied far beyond software. John identifies nine distinct subscription models and shares case studies showing how companies like Dollar Shave Club, Salesforce, and Zipcar use them to build predictable recurring revenue. The conversation covers the LTV to CAC ratio that venture capitalists look for (at least 3:1), why Amazon is both a threat and an inspiration for subscription businesses, and how front-of-the-line support pricing creates premium SaaS monetization tiers. John also explains why he wishes he had written this book before Built to Sell - because building recurring revenue should come before thinking about exits.

From Spreadsheets to a SaaS Marketplace at $1M ARR - Katherine Sears

Katherine Sears, Booktrope

From Spreadsheets to a SaaS Marketplace at $1M ARR

Katherine Sears is the co-founder and chief marketing officer of Booktrope, a SaaS marketplace that connects authors with editors, designers, and marketing managers to collaboratively publish books. Everyone on the team works for a percentage of profits - no upfront fees. Before Booktrope had any software, Katherine and her co-founder Ken ran the business for a year and a half using spreadsheets and email. They validated the model manually, figuring out what worked and discarding what did not. When CTO Andy joined, he turned the manual process into a SaaS marketplace platform called TeamTrope. The first version took just a few months to build, and they immediately started migrating their existing users. Katherine used Twitter to build authority in the book publishing space long before she had anything to sell. She spent months answering questions, reviewing books, and becoming a trusted voice in the self-publishing community. When Booktrope launched, those relationships converted into early adopters. The company went through Y Combinator's Winter 2015 batch, where they grew from a couple hundred books in the pipeline to over a thousand. After automating their application system, Booktrope scaled 10% per week and hit a $1M annual run rate with plans to reach $3M by year end.

3 Methods to Get Early Traction Before Writing Code - Trevor Owens

Trevor Owens, Javelin.com

3 Methods to Get Early Traction Before Writing Code

This is part two of the interview with Trevor Owens, co-founder and CEO of Javelin.com. In episode 61, Trevor shared the story of how he built Lean Startup Machine into a business doing almost $2 million a year, and how QuickMVP reached $240,000 in annual recurring revenue in its first three months. In this episode, we get tactical. Trevor breaks down the exact three-step process he teaches at Lean Startup Machine workshops for achieving early traction before writing a line of code. The first method is customer interviews - but not the kind where you pitch your solution. Trevor teaches a three-point interview format: identify the problem, get the customer to tell a story about experiencing the problem, and ask the magic wand question about their ideal solution. If they can't describe a solution, it's probably not a big enough problem. The second method is pre-selling through landing pages and Google Ads. Trevor explains how $100 to $500 in ad spend can validate whether anyone actually wants what you're building. QuickMVP combines a landing page builder with a Google Ad creator so founders can test ideas in under a minute instead of the 45 minutes typical for first-time AdWords users. The third method is concierge delivery - delivering your product's value as a manual service before building technology. Trevor shares a powerful example from a Lean Startup Machine event where a team got $1,000 in pre-orders for a resume sorting app, then discovered through concierge delivery that customers actually needed hiring expertise, not just automation. The conversation also covers why almost every successful startup has pivoted (YouTube started as a dating site, Twitter as a podcasting platform), why 90% of QuickMVP cancellations come from founders who invalidated their idea but didn't know what to do next, and why the rate of improvement across iterations matters more than your first baseline test.

70% Said Very Disappointed - Measuring SaaS Product-Market Fit - Trevor Owens

Trevor Owens, Javelin.com

70% Said Very Disappointed - Measuring SaaS Product-Market Fit

Trevor Owens is the co-founder and CEO of Javelin.com, the makers of QuickMVP and Lean Startup Machine. QuickMVP is a service that lets you quickly test business ideas by combining a landing page builder with a Google Ad creator. Lean Startup Machine is a three-day workshop that teaches entrepreneurs how to validate ideas by talking to customers instead of just building products. The story of how Trevor achieved SaaS product-market fit is a lesson in practicing what you preach. He started organizing hackathons in New York but found that teams always built cool demos that would never become real businesses. So he created Lean Startup Machine - a workshop where the winner wasn't the best demo but the team that got the most customers to sign up in three days. Trevor measured SaaS product-market fit using the Sean Ellis survey. He asked attendees "How disappointed would you be if you could not have attended LSM?" and expected around 40% to say "very disappointed" - the standard threshold for product-market fit. He got 70%. That result convinced him to go full-time and scale to 100 workshops per year. But scaling came with hard lessons. Trevor hired too fast, spent event revenue before delivering services, and had to cancel events and delay paying his team. When he pivoted to software, he initially built an enterprise project management tool and sold it to GE and American Express - only to discover that enterprise onboarding without SaaS product-market fit was nearly impossible. He eventually pivoted to QuickMVP, a consumer-first tool that could iterate toward product-market fit before attempting enterprise sales. The conversation also covers how organizing events as an introvert became Trevor's secret weapon for building relationships with Eric Ries, Dave McClure, Seth Godin, and Hiten Shah - and why adding value selflessly is the most scalable networking strategy.

86% Startup Traction Rate From 1500 Launches - How - Adeo Ressi

Adeo Ressi, Founder Institute

86% Startup Traction Rate From 1500 Launches - How

Adeo Ressi is the founder and CEO of the Founder Institute, the world's largest entrepreneur training and startup launch program. The organization was launched in 2009 and now operates in over 100 cities worldwide, helping aspiring founders build technology companies through a structured three-and-a-half-month program. The numbers behind the Founder Institute's approach to startup traction are remarkable. Of the 1,500+ companies created through the program, 86% are still alive and 70% are doing well. About half are funded. The program has a 65% dropout rate by design - it mimics the real stresses of entrepreneurship so founders who can't handle the pressure discover that before investing years into a company. Adeo breaks down startup traction into three factors: genetics (personality traits like stress tolerance and fluid intelligence), circumstance (personal and market conditions), and perseverance. He argues that your idea matters far less than these three factors - pointing out that even Twitter was arguably a "bad idea" but succeeded because of the people behind it. The conversation covers how the Founder Institute uses psychometric testing to predict which founders will achieve startup traction, why sequencing matters (like naming your company before incorporating), and how peer-to-peer learning combined with structured mentorship creates better outcomes than either approach alone. Adeo also explains why a company dies when the founder gives up - making perseverance the single most important predictor of startup success.

9 Months With Zero Startup Funding Built a 100M-User App - Chris Barton

Chris Barton, Shazam

9 Months With Zero Startup Funding Built a 100M-User App

Chris Barton is the co-founder of Shazam, the mobile music recognition service that started as an idea in 1999. Every expert in audio signal processing told him and his co-founders that identifying music from noisy phone audio was impossible. They did it anyway. Chris and his team spent their first 9 months with zero startup funding, focused entirely on finding the right technical co-founder and inventing the core algorithm. They recruited Avery Wang by networking through Stanford and MIT PhD programs in signal processing. Once they had a working demo and a patent, they raised close to $1 million from angel investors, followed by a $7.5 million Series A. But building Shazam in 2000-2002 meant building everything from scratch. There were no cloud servers, no digital music databases, and no smartphones. Users would dial a phone number, hold their phone up to the music, and receive an SMS with the song name. Growth was slow for years. The real breakthrough came in 2008 when Apple launched the App Store. Shazam shot to the top of the charts and never left, eventually reaching over 100 million monthly active users. Chris shares the fundraising strategy that worked, the biggest mistake he made as a first-time CEO, and why he stepped down to let an experienced operator take the helm.

From Free Marketplace to $1M in Freemium SaaS Revenue - Ryan Hamlin

Ryan Hamlin, PlaceFull

From Free Marketplace to $1M in Freemium SaaS Revenue

Ryan Hamlin left Microsoft after years of running marketplaces like Carpoint and HomeAdvisor. In 2011, he co-founded PlaceFull with George Webb, investing $400,000 of their own money to build an online marketplace for booking spaces, classes, camps, and events. The original model was simple: merchants listed for free, and PlaceFull took a cut of each booking. But Ryan quickly hit a wall. When merchants pay nothing, they have no skin in the game. Inventory went stale, bookings were unpredictable, and the unit economics pointed toward failure. So PlaceFull made a freemium SaaS pivot. Ryan rebuilt the platform to become the master scheduling tool for each merchant's business, adding Google Calendar sync, website embedding, and Facebook integration. He introduced a monthly subscription fee of $30-40 and reduced transaction fees by 80%. The result: merchants who paid even a small amount treated the platform as a core part of their business. Today, PlaceFull has 27,000 merchants in its freemium SaaS tier and about 1,000 paying subscribers. The company is on track for its first million-dollar revenue year. Ryan shares how partnering with industry associations drove cost-effective acquisition, why he wishes he had been less rigid about his MVP, and how consecutive months of 15-20% growth finally gave him confidence the freemium SaaS model was working.

From $2.50 to $500/Mo: A SaaS Pricing Evolution - Adam Schoenfeld

Adam Schoenfeld, Simply Measured

From $2.50 to $500/Mo: A SaaS Pricing Evolution

Adam Schoenfeld is the co-founder and CEO of Simply Measured, a social media analytics platform used by brands like Samsung, Microsoft, American Express, and Pepsi. The company was founded in 2010 and has raised $29 million in VC funding. But the story of Simply Measured starts with a failure. Adam's first startup, Cheddar Media, never achieved product-market fit. He spent years building a consumer app that pivoted multiple times before shutting down. That experience taught Adam a critical lesson about SaaS pricing: build something people will pay for from day one. When Adam and his co-founders Aviel Ginsberg and Damon Cortese launched their next venture, they did not even have an idea. They called it "Untitled Startup" and ran experiments in the social marketing space until one of them - a weekend hack called RowFeeder that dumped Twitter hashtag data into spreadsheets - started getting traction. The initial SaaS pricing was almost comically low. You could get 48 hours of usage for $2.50, or pay $10 a month for a basic plan. But when agencies started asking for more robust features, Adam introduced a $500/month tier. That pricing leap was the turning point. Within six months, Simply Measured hit $10,000 in monthly recurring revenue. Within two years, enterprise brands were signing annual contracts worth many times the original price point. Today Simply Measured has 125 employees, is growing at roughly double each year, and operates on an eight-figure revenue run rate. Adam shares the SaaS pricing mistakes he made early on, how he moved upmarket to enterprise without losing focus, and why charging money from day one gave him validation that his failed startup never provided.