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The SaaS Podcast

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Episodes, Page 2

Sam Darawish, Everflow

Bootstrapped SaaS to $30M ARR: Why Scarcity Forces Focus

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.

David Shim, Read AI

Product-Led Growth to 8-Figure ARR with $0 Ad Spend

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. 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%. 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. Product-led growth at its purest.

Kevin Wagstaff, Spectora

Bootstrapped SaaS: From $5K to $27M ARR in a Forgotten Niche

Kevin Wagstaff is the co-founder of Spectora, a modern all-in-one platform for home inspectors that he and his brother Michael bootstrapped from $0 to $10M ARR before raising funding. In 2016, Kevin was a realtor with a knack for marketing and SEO. His brother was a self-taught developer. When a friend mentioned how outdated home-inspection software was, they spotted a niche no one was serving and went all in with $5,000 and a lot of grit. They spent six to nine months talking to inspectors: buying coffee, riding along on jobs, listening. What they found was simple: inspectors were wasting hours writing reports after each job. That inefficiency became their focus. Their first version was a mobile-first app that helped inspectors take photos, label issues, and finish reports faster. Soon after, they expanded into a full business platform with scheduling, payments, texting—everything in one place. But winning trust was the real challenge. Many inspectors were in their 50s or 60s and skeptical of cloud software and monthly subscriptions. So Kevin focused on something most bootstrapped SaaS founders overlook: showing up consistently and genuinely helping people before ever asking for the sale. Kevin started a separate blog called SmartHomeInspector.com 12 months before Spectora launched, writing content on how to market your business as a home inspector. He offered free SEO audits and even built websites for early customers—over 200 of them manually—just to get them talking about the software. Within two years, Spectora hit $1M ARR. They kept building from there. By 2024, the company had grown to $27M ARR, serving over 12,000 customers with a 100-person team.

Sergiy Korolov, Mailtrap

Product-Led Growth: From Internal Mistake to 7-Figure SaaS

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.

Jonathan Kazarian, Accelevents

Bootstrapped SaaS: 5 Years Part-Time to $10M ARR

Jonathan Kazarian is the founder and CEO of Accelevents, an event management platform that helps organizations run everything from conferences to virtual events. Back in 2014, while working at a hedge fund, Jonathan's 17-year-old cousin got sick. He organized a fundraiser but couldn't find affordable event software with decent support. So he built a solution with someone he knew. It worked so well that other organizations started asking for it. As demand grew, Jonathan started using Upwork contractors to build out the platform while he managed the product side. But Jonathan didn't quit his day job. For five years, he worked 60-hour weeks nights and weekends building this bootstrapped SaaS. He and his co-founder even scheduled date nights on different days so one was always on call. By 2020, after five years of this grind, he hit $1 million ARR and finally went full-time. Perfect timing, right? COVID hit and wiped out every event worldwide. Revenue dropped to zero, and cashflow went negative as they refunded all their transaction fees. A month later, Jonathan borrowed $75,000 from his father's retirement to keep the company alive. But instead of waiting it out, they pivoted hard to virtual events. Jonathan and his team started pre-selling features they hadn't built yet using Figma mockups. Within three months, they hit a million-dollar run rate. By year's end, they'd 10X'd revenue and grown from 10 to over 100 people. But in 2022, the tech bubble burst. Revenue got cut in half. Jonathan had to lay off more than half his team while the company bled customers for 12 straight months. Today, Accelevents serves over 1,000 customers and generates $10 million ARR with 60 people - proof that a bootstrapped SaaS can survive multiple near-death experiences.

Richard Hollingsworth, Fyxer

Agency to AI SaaS: Scaling from $1M to $18M ARR in 9 Months

Richard Hollingsworth is the Co-founder and CEO of Fyxer, an AI-powered email assistant that predicts and drafts emails for busy professionals. Richard and his brother Archie grew up on a farm, but they knew the slow pace of agricultural life wasn't for them. They saw tech as the opposite environment—fast feedback loops, results within your control. They started by building the UK's largest executive assistant agency, bootstrapping it to $5M in revenue. But from day one, they had a bigger vision: turning the service into software. For years, they tried to build "tech-enabled" solutions, but nothing worked to pull the price down enough for the mass market. Then GPT-3 launched. It was the breakthrough they'd been waiting for. Unlike other AI SaaS startups starting from scratch, Fyxer had a secret weapon: six years of detailed logs from human assistants. They knew exactly how an EA organizes an inbox because they had thousands of hours of data on it. They used this proprietary data to train their AI models, ensuring their product was more accurate than a generic LLM wrapper. The growth was explosive. They started the year with $1M ARR and a team of four. Within 9 months, they hit $18M ARR. They moved to San Francisco, joined an AI residency, and shifted their focus from "Tech Bros" to "Professional Services"—real estate brokers, consultants, recruiters—people who actually drown in email. One of their biggest wins came from a single signup via a Facebook ad. That user turned out to be the CEO of a massive real estate brokerage. Within 7 days, Richard's brother Archie flew to Seattle, met the CEO at his lake house, and closed a $1.2M deal to roll Fyxer out to 5,000 employees.

Bernard Aceituno, Stack AI

The Enterprise Sales Playbook That Took Stack AI to 7 Figures

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.

Pat Kinsel, Proof

SaaS Growth: From Negative Margins to $100M ARR

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. For the first few years, SaaS 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. As the pandemic waned, Pat had to refocus the company on enterprise customers and expand the platform beyond just 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.

Todd Olson, Pendo

Finding Product-Market Fit: From 2 Failures to $200M ARR

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. In this episode you'll learn: Why Todd refused to hire salespeople until he'd validated the sales motion himself at $500K ARR How raising prices 10x overnight transformed Pendo's trajectory without losing deals What Todd learned from two failed startups that shaped his obsession with product-market fit Why creating a new category meant abandoning inbound marketing for manual education How for five years Todd refused to build features competitors had and why that became Pendo's biggest differentiator

Flo Crivello, Lindy

AI SaaS Positioning: From Broken Product to 7-Figures

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.

Richard White, Fathom

SaaS Retention: Why 99% of Signups Failed (And How He Fixed It)

Richard White is the founder and CEO of Fathom, the #1 rated AI note-taking app that automatically captures and summarizes meetings. In 2019, after running UserVoice for over a decade, Richard decided it was time for a change. Like many people, he struggled to take notes while talking in meetings. When the pandemic hit, he saw his opportunity. He recruited four of his best engineers from UserVoice and raised funding on day one. But growth was painfully slow. After nearly a year, they only had 50 stable users. The problem was trust. People wouldn't bring an unknown bot into real meetings. They wanted to test it first, but testing on their own didn't work because the bot would mute itself. So his team built a clever fix - a bot that played pre-recorded video, giving users a "fake" meeting to help them build confidence. Then Zoom launched its app marketplace and included Fathom. They exploded to 100,000 signups in the first month. But only 100 people were actually using it daily. Turns out 99% of signups had zero meetings on their calendars. Zoom had sent them tons of free users who weren't using the platform for business. Richard's SaaS retention numbers looked catastrophic. Instead of giving up, Richard saw opportunity. The thousands of low-quality signups were actually the perfect testing ground to fix their broken onboarding and solve their SaaS retention problem. Just as growth took off in 2022, the funding market crashed. VCs started demanding revenue over user growth. Richard gave his team 60 days to monetize. They started selling a team plan before it was built - just two features ready and a slide deck showing what was coming. It worked - they hit $100K ARR in the first month and reached $1M ARR in a year. Today, Fathom generates eight figures in ARR with 80 employees and serves around 175,000 companies.

Rob Woollen, Sigma Computing

Product-Market Fit: 7 Years of Zero Revenue to $100M

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 search for 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 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. Rob Woollen and Sigma Computing used these strategies to achieve product-market fit: 1. Stayed laser-focused on the problem for 7 years while pivoting the solution multiple times 2. Cultivated 10 high-touch champion users within walking distance of their office 3. Rebuilt the product to integrate with Snowflake's cloud data warehouse in 30 days 4. Rebuilt again at $1M ARR because the interface "still wasn't quite right" Today, Sigma Computing has crossed $100M in revenue with 600+ employees and 1,400+ customers.

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