SaaS Club
PodcastPlaybooksCoachingSponsorFree ToolsJoin Community
saasclub

Helping SaaS founders build and scale profitable businesses since 2014. Powered by real experience from 472+ founder conversations.

Content

  • The SaaS Podcast
  • Founder Playbooks
  • Blog
  • Newsletter
  • Free Tools

Programs

  • Plus
  • Launch
  • Mastermind
  • Accelerate

Company

  • Contact
  • Become a Sponsor
  • Suggest a Guest
  • Terms
  • Privacy

© 2026 SaaS Club. All rights reserved.

Built with ❤️ for SaaS founders

Pricing & Monetization

SaaS Pricing & Monetization

How SaaS founders figured out pricing. From first price point to enterprise tiers, these are the strategies, experiments, and mistakes that shaped their revenue.

Real founder strategies. Delivered weekly.

Free weekly newsletter · No spam

Pricing is the fastest lever you can pull to grow revenue. It's also the one most founders spend the least time on. They pick a number early, copy a competitor, and never revisit it.

These episodes will change how you think about pricing. You'll hear from founders who doubled revenue with a single pricing change. Others who spent months testing different models before finding what worked. And a few who underpriced for years before realizing they were leaving serious money on the table.

The conversations cover the full spectrum of SaaS pricing decisions. Per-seat vs. usage-based. Flat rate vs. tiered. Free trials vs. freemium. Founders share the exact experiments they ran, the data they looked at, and the customer reactions they navigated when raising prices.

You'll learn how to think about value-based pricing when your customers range from startups to enterprises. How to structure tiers that naturally push customers toward higher plans. How to handle the awkward conversation when you need to raise prices on existing customers. And how to tell whether your pricing problem is actually a positioning problem.

Some founders here are running $29/month products with thousands of customers. Others are closing six-figure annual contracts. The pricing strategies are different, but the underlying principles are surprisingly consistent.

If you suspect your pricing isn't right (and most founders' pricing isn't), start here.

Browse by topic:AllBootstrappingFirst CustomersProduct-Market FitEnterprise SalesProduct-Led GrowthPricing & MonetizationFounder-Led SalesPositioning & DifferentiationChurn & RetentionContent & Inbound MarketingExits & AcquisitionsFundraisingAI-Powered SaaS

Get weekly SaaS insights

Real founder strategies. Delivered to your inbox.

Free weekly newsletter · No spam

←All Episodes
How to Close Enterprise Sales Deals in 9 Days - Bassem Hamdy

Bassem Hamdy, Briq

How to Close Enterprise Sales Deals in 9 Days

Bassem Hamdy is the co-founder and CEO of Briq, an AI orchestration platform for the construction and manufacturing industries. In 2018, after spending nearly two decades in construction tech - including a stint at Procore where he helped scale the company from $10 million to $100 million ARR - Bassem set out to build what he called the "construction data cloud." The idea was to aggregate all project data through APIs, creating a Carfax-like record for physical assets. It seemed like a perfect fit given his experience. There was just one problem. The software systems used in construction were 30 to 40 years old, and none of them had APIs. His entire concept was technically impossible. Bassem was ready to give up and go back to corporate life when a chance meeting with an engineer introduced him to robotic process automation. These bots could log into legacy systems and extract data without APIs. Suddenly, the business had new life. But customers wanted more than data extraction. They asked if the bots could also enter data. This pivot to "digital workers" found product-market fit quickly, and by 2020, Briq had reached $1.5 million in ARR. Then came pressure from investors. VCs didn't like that no users logged into the product. They pushed Bassem to build something with daily active usage. So Briq pivoted again, this time to a forecasting tool. It was a disaster. Customers loved the idea of automated forecasting, but the product couldn't deliver on that promise. Less than two years later, they killed it and returned to their automation roots. As if that weren't enough, Briq had ballooned to 300 employees during the growth phase. The larger team created more problems than it solved, and Bassem says they "lost the plot." Painful layoffs followed in 2023 and 2024, reducing the team to 100 people. Today, Briq generates 8-figures in ARR and is targeting $100 million within three years. Bassem credits their turnaround to a counterintuitive enterprise sales strategy: skip the demos, refuse free POCs, and close enterprise sales deals in 9 days by selling vision and value to CFOs who control the budget.

How Freemium SaaS Grew to Millions of Users With 20 People - Bilal Aijazi

Bilal Aijazi, Polly

How Freemium SaaS Grew to Millions of Users With 20 People

Bilal Aijazi is the co-founder of Polly, an engagement platform that brings polls, surveys, and feedback workflows into the tools teams already use like Slack, Teams, and Zoom. In 2015, Bilal was working at a consumer messaging company, watching apps like WeChat evolve from simple chat tools into full-blown platforms. He figured the same shift would happen at work. So he and his co-founder Samir started experimenting with simple solutions to collect feedback. Their first attempt was an email-based tool, but engagement was terrible. People just treated it like another survey to avoid. Then Slack opened their API. And Bilal noticed people on Twitter asking for Slack polls. So the founders quickly ported their product over, becoming one of the very first Slack apps ever built. But the installation process was clunky. Five manual steps that required copying and pasting tokens between different screens. Yet 80% of people still completed the setup. So they were clearly providing something people wanted. Then one day someone posted Polly on Product Hunt and they went viral overnight. They were getting thousands of new signups every month and struggling to keep the servers running. Yet they had zero revenue. Their first paying customer spent $8 a month for a fantasy football league. Then came the real challenge of building a freemium SaaS - figuring out who would actually pay. Most freemium SaaS users just wanted to do something casual with polls like pick lunch spots. But through hundreds of conversations, they found where the real money was. They focused on company all-hands, sales kickoffs, and other high-stakes meetings where feedback actually mattered. Just when things clicked, Slack threw a spanner in the works. Polly had built a workflow feature for automating feedback. They were signing five-figure deals. Six months later, Slack launched their own solution. The founders had to make a choice. Stay on Slack and hope for the best, or take a massive risk and rebuild everything for multiple platforms. They expanded to Teams, Zoom, Google Meet, and embedded directly into presentations. Rebuilding their entire infrastructure was a huge undertaking, but they had no choice. Today, Polly is one of the most successful freemium SaaS products in the collaboration space, serving millions of monthly active users and generating multiple seven figures in ARR with just 20 people.

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.

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 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.

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

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.

Bootstrapped to $1M ARR in 90 Days: The TikTok Affiliate Strategy - David Zitoun

David Zitoun, Submagic

Bootstrapped to $1M ARR in 90 Days: The TikTok Affiliate Strategy

David Zitoun is the co-founder and CEO of Submagic, a tool that helps creators and small businesses turn their videos into viral-ready shorts in just a few clicks. David Zitoun had a problem. As a longtime video creator, he wanted captions that looked like Alex Hormozi's viral style - but creating them in Premiere Pro was painful and time-consuming. So he built a tool to solve his own problem. He found his co-founder through Y Combinator's Co-Founder Match platform, and they made a pact: build an MVP in 15 days, try to sell it in 15 days. If nothing worked after 12 months of monthly experiments, they'd move on. Submagic was the first product they tried. With no money for paid ads, David started posting TikTok videos promoting Submagic from a brand new account with zero followers. Ten days later, one video went viral with 100,000 views, bringing in the first 40-50 paying customers. Then he scaled the playbook: he recruited 50-70 young creators as affiliates, paying them 30% lifetime commissions to post daily TikTok videos promoting Submagic. The affiliate army worked. Within 90 days, this bootstrapped SaaS hit $1M ARR. But at $5M ARR, growth stalled for seven months. David's team tried everything - more features, more acquisition channels - nothing moved the needle. The breakthrough came when they lowered prices instead of raising them, and launched Magic Clips to help podcasters and YouTubers turn long-form content into shorts. Today, Submagic is a bootstrapped SaaS at $8M ARR with a 14-person remote team across 10 time zones. SEO now drives 25% of revenue, word of mouth is the top acquisition channel, and David still spends 50% of his time talking to customers - the same thing he did on day one.

First Customers From a Notion Page and Python Scripts - Stefan Bader

Stefan Bader, Cello

First Customers From a Notion Page and Python Scripts

Stefan Bader is the co-founder and CEO of Cello, an all-in-one referral platform that helps SaaS companies reward their users for bringing in new customers. Back when Stefan was Chief Revenue Officer at a payment processing company, he noticed something odd. His users were bringing in tons of new customers, but there was no way to reward them. Every tool out there was for affiliates and influencers. Stefan saw the opportunity. And in 2022, he quit his job and started Cello. But building it turned out to be way harder than he'd imagined. Paying individual users meant navigating compliance laws in dozens of countries, international banking regulations, and tax requirements that no one had mapped out before. And his MVP was embarrassingly basic. Customers got their analytics through shared Notion pages. No login portal. No dashboard. Just Stefan's team running Python scripts and configuring everything manually behind the scenes. "This is not a product," one early customer told him. But Stefan stayed focused on what mattered - could it actually generate referrals? The answer was yes. He also made pricing dead simple - pay nothing until you make money from referrals. However, most SaaS companies didn't even know they needed this product. Stefan had to educate every prospect about why user referrals were different from affiliate programs, and why they were leaving money on the table. As early customers started seeing results, word spread. But the real breakthrough came from something tiny - a "powered by Cello" link in their widget. As customers grew, millions of their users saw it. That little link became their biggest growth driver. Today, Cello generates $2.5M in ARR, powers referral programs for companies like Miro and Typeform, and reaches over 7 million users each month.

Why Expert Advice Nearly Killed This SaaS - Sameer Al-Sakran

Sameer Al-Sakran, Metabase

Why Expert Advice Nearly Killed This SaaS

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 - just a simpler way to answer basic questions from a database without needing a complex data stack. It wasn't 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 wouldn't 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 wasn't 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 self-serve flow pulled in close to six figures in ARR without a single sales call. But instead of doubling down on this product-market fit 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-market fit 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: 1. Win the taste test - if users try Metabase alongside Tableau and Looker, make sure Metabase wins 2. Let the product sell itself - put CTAs where users already are, not behind sales calls 3. Accept how customers want to pay - after two years fighting per-user pricing, adopting it simplified everything Today, Metabase has a team of over 100 people and serves companies worldwide with an open-source BI tool that proves product-market fit often looks simpler than experts expect.

Selling a Bootstrapped SaaS: Avoid These Mistakes - Andrew Gazdecki

Andrew Gazdecki, Acquire.com

Selling a Bootstrapped SaaS: Avoid These Mistakes

Andrew Gazdecki is the founder and CEO of Acquire.com, the largest marketplace for buying and selling SaaS startups. Before starting Acquire.com, Andrew bootstrapped and sold his own SaaS company. He grew it to $10 million in annual recurring revenue, but when he went to sell, the process was a massive headache - he spent years finding a buyer and had no idea what due diligence or legal terms meant. That painful exit became the inspiration for Acquire.com. Today, the platform has helped over 2,000 startups get acquired, with total deal volume exceeding $500 million. Andrew explains how bootstrapped SaaS businesses are ideal acquisition targets for financial buyers like private equity firms, family offices, and individual entrepreneurs. Andrew reveals the three biggest mistakes sellers make: overvaluing their business, refusing earnouts or creative deal structures, and failing to get their house in order before listing. He walks through the full selling process on Acquire.com - from creating a draft listing, to going live with over 500,000 registered buyers, to using deal schedules that create momentum and drive competing offers. On the buying side, Andrew covers red flags to watch for, why code quality matters less than distribution and customers, and how one buyer turned a $25-50K acquisition into a $2M revenue business by rebranding it as pdf.ai. He also discusses the growing wave of AI-first bootstrapped SaaS businesses and why the barrier to entry for building these companies keeps getting lower.

From Zero to $27M ARR Without Raising a Dollar - Martha Bitar

Martha Bitar, Flodesk

From Zero to $27M ARR Without Raising a Dollar

Martha Bitar is the co-founder and CEO of Flodesk, an email marketing platform designed for small businesses and creators. In 2019, Martha and her co-founder Rebecca launched Flodesk to make beautiful email marketing accessible to everyone. They bootstrapped the business from day one, focusing on design and simplicity over complex features. Martha was working in partnerships at HoneyBook when she noticed a pattern: small business owners with massive Instagram followings couldn't get a single newsletter out. The problem wasn't 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 didn't start building until they made someone cry happy tears. Their unique 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. Today, Flodesk generates over $27 million in ARR with hundreds of thousands of customers, proving that bootstrapped SaaS companies can compete with VC-backed giants by focusing on design, simplicity, and unconventional pricing.

ClickFunnels: Bootstrapping a SaaS to $140M ARR with Webinars - Todd Dickerson

Todd Dickerson, Clickfunnels

ClickFunnels: Bootstrapping a SaaS to $140M ARR with Webinars

Todd Dickerson is the co-founder of ClickFunnels, a SaaS platform that helps businesses build and optimize sales funnels to sell products and services online. In 2011, Todd replied to a mass email from internet marketer Russell Brunson looking for help with a Ruby on Rails app. That email reply changed the course of his life. After helping Russell and his team with the app, Todd and Russell collaborated on various projects over the next few years. Eventually, they decided to launch ClickFunnels in 2014, with a mission to simplify the process of building sales funnels for online businesses. With Russell's large audience, built over many years, they expected ClickFunnels to attract 10,000 customers quickly. But their initial launch only brought in about 1,000 signups, falling well short of their expectations. Their breakthrough came when Russell created and sold a Funnel Hacks masterclass for $997 at an event and bundled ClickFunnels for free. This strategy became their primary growth engine. Over the next few years, they ran weekly webinars, driving traffic from Facebook ads to live sessions where Russell would teach and then sell the training and software. One of their biggest challenges came when they faced a critical database outage that lasted eight hours. It was a major crisis that threatened both their revenue and reputation, with some customers even sending death threats. Another major challenge was scaling their infrastructure. With only five engineers supporting 10,000 customers, the team struggled to keep the platform stable while adding new features. Today, ClickFunnels generates over $140 million in ARR, serves over 100,000 customers and is still fully bootstrapped.

PSPDFKit: Bootstrapping a SaaS $20K to $1M ARR in 8 Months - Jonathan Rhyne

Jonathan Rhyne, PSPDFKit

PSPDFKit: Bootstrapping a SaaS $20K to $1M ARR in 8 Months

Jonathan Rhyne is the co-founder and CEO of PSPDFKit, a software development kit that enables developers to integrate advanced PDF functionalities into their apps. In 2014, Jonathan was working as an attorney, living with his in-laws, and about to start a family when he took a huge risk to join PSPDFKit as a co-founder. The startup was making just $20K in monthly recurring revenue (MRR). Jonathan and his co-founder faced the challenge of growing their business in a market where even Adobe hadn't yet solved the problem. They immediately got to work. Jonathan overhauled their pricing, introduced a new subscription model, and focused on creating valuable content to attract developers. The hard work paid off. In just 8 months, they grew from $20K to $1 million in annual recurring revenue (ARR) a huge win for any startup. But their rapid growth also brought unexpected challenges. They struggled to balance customer demands with their long-term vision, often resorting to quick fixes that risked creating technical debt and future problems Despite their initial success, the next few years were challenging. Their attempts to launch new products didn't work out, leaving them unsure of their direction. Growth slowed down. Market uncertainties and tight finances tested their resolve. But they persevered, steadily growing the business year after year. Today, after overcoming numerous obstacles, their business generates multiple eight figures in revenue, with a team of 150 people across 27 countries.

A Guide to Buying & Selling a SaaS Business on Marketplaces - Juan Ignacio Garcia

Juan Ignacio Garcia, Boopos

A Guide to Buying & Selling a SaaS Business on Marketplaces

Juan Ignacio Garcia is the founder and CEO of Boopos, the #1 platform for buying and selling profitable online businesses with built-in financing for qualified buyers. Buying an established SaaS business can be an attractive alternative to starting one from scratch. You get to skip the initial stages of finding product-market fit and start with paying customers and revenue. On the flip side, selling your SaaS business can be an exciting and potentially life-changing event, allowing you to cash out and move on to new adventures. But the process can be complex and daunting, especially for first-timers.

Hubstaff: Overcoming Early Struggles to Bootstrap to $22M ARR - Jared Brown

Jared Brown, Hubstaff

Hubstaff: Overcoming Early Struggles to Bootstrap to $22M ARR

Jared Brown is the co-founder and CEO of Hubstaff, a time-tracking and workforce management software for remote teams. In 2012, Jared got a message on LinkedIn from Dave, a complete stranger at the time, pitching an idea for a SaaS product. Dave had already built a basic product that was generating some revenue, but he needed a technical co-founder to help take it to the next level. Jared was intrigued but also cautious. It took three months of discussions before he finally agreed to join forces with Dave. But finding traction in the early days was far from easy. The founders were constantly torn between working on the product and trying to acquire customers. They were stuck in an endless cycle of building features, launching them, and then realizing they still weren't gaining enough traction. On top of that, they struggled with pricing strategy, debating whether to keep prices low to attract more customers or charge more to increase revenue. There were also constant discussions about which features to prioritize and how to allocate their limited development resources. And despite seeing some early signs of success, they couldn't shake the nagging feeling that maybe they were kidding themselves. Would enough people really be willing to pay for this product? But they persevered, and today, Hubstaff generates around $22 million in ARR, serving over 16,000 customers with a team of just over 100 people.

Kumospace: From $1M ARR to a Pivot Driven by Churn - Brett Martin

Brett Martin, Kumospace

Kumospace: From $1M ARR to a Pivot Driven by Churn

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 they're 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.

m3ter: From Early Sales Struggles to Finding Product Market Fit - John Griffin

John Griffin, m3ter

m3ter: From Early Sales Struggles to Finding Product Market Fit

John Griffin is the co-founder of m3ter, a subscription management platform that helps software companies enable usage-based pricing models. In 2020, John was working at Amazon Web Services when he and his co-founder Griffin realized many software companies struggled to implement effective usage-based pricing. Having dealt with these challenges in their previous startup, which was acquired by Amazon, they decided to start a new company aimed at helping subscription businesses seamlessly adopt usage-based pricing. As second-time founders, John and Griffin quickly encountered familiar roadblocks trying to drive early sales. Despite their experience and a well-thought-out product, their initial attempts at connecting with potential customers fell flat. As their cold outreach efforts continued to stall, the founders felt increasing pressure to sign those critical first customers to validate their product offering. And to add to their struggles, they initially made the mistake of going too broad with the types of customers they sold to. This inevitably spread them too thin, making it difficult to focus on the right features and craft a clear message. Just when things started to feel hopeless, they got a lucky break, an investor made an introduction to a significant first buyer. Landing this major customer finally gave John and Griffin the desperately needed sales momentum. Today, m3ter generates multiple seven figures in annual revenue and has raised over $30 million in funding.

Paddle: From a Failed SaaS Launch to a $1.4+ Billion Valuation - Christian Owens

Christian Owens, Paddle

Paddle: From a Failed SaaS Launch to a $1.4+ Billion Valuation

Christian Owens is the founder and CEO of Paddle, a payments infrastructure provider for SaaS companies. Christian started building websites when he was 12 years old. He walked into his local high street stores and asked them if they wanted him to build a website. His first customer was an Indian Restaurant. At 14 years old, inspired by Groupon, Christian persuaded a number of software vendors to participate in selling a discounted software bundle to their email lists and generated over a million dollars in sales. Today, Christian is running a company that employs nearly 400 people, is approaching $100M in ARR, and has raised $300M in VC funding. Paddle also acquired Profitwell earlier this year in a deal worth $200M. I originally interviewed Christian over 3 years ago when Paddle was doing around $10M in ARR.

Fomo: From a Small Shopify App to a 7-Figure SaaS Business - Ryan Kulp

Ryan Kulp, Fomo

Fomo: From a Small Shopify App to a 7-Figure SaaS Business

Ryan Kulp is the former founder of Fomo, a social proof marketing solution that enables online businesses to show purchasing activity on their website automatically. In 2016, Ryan acquired a Shopify app called Notify (which later became Fomo) and grew it into a 7-figure SaaS business that he recently sold. The Shopify app already had a few hundred customers, so it was less about a zero-to-one problem and more about how to make the investment worthwhile and grow to thousands of customers so he could quit his job and work on it full time.

Fleetio: How a Solo Founder Built an 8-Figure SaaS Business - Tony Summerville

Tony Summerville, Fleetio

Fleetio: How a Solo Founder Built an 8-Figure SaaS Business

Tony Summerville is the founder and CEO of Fleetio, a SaaS product that helps businesses automate fleet operations tasks and keep their vehicles and equipment running smoothly. In 2011, Tony was working as a product manager. He'd tried several times to start a business in his spare time but just wasn't able to get any traction. Eventually, he came to the realization that if he was going to have a serious shot at building a business, he had to quit his job and go all-in. He and his wife agreed that he'd give it a try for one year and if things didn't work out, he'd go back to a full-time job. After seeing how his father's business was struggling to manage its fleet of vehicles, Tony set out to build a modern fleet management software for small and medium businesses. He launched his minimum viable product (MVP) in about 7 months and a few months later had his first 10 customers (thanks to the time and effort he'd put into doing customer development interviews). But he was only charging about $50 a month for his product, so there was still a lot of work to do. Today, he's grown his company into an 8-figure SaaS business, built a team of nearly 200 people, and raised $25M in VC funding. In this interview, we talk about how Tony validated his idea, built his MVP, tested pricing, built a content marketing engine, and more. So I hope you enjoy it.

SaaS Growth Metrics 101: CAC, LTV, Retention and Churn - Paul Orlando

Paul Orlando, Startups Unplugged

SaaS Growth Metrics 101: CAC, LTV, Retention and Churn

Paul Orlando is the founder of Startups Unplugged where he's building an internal incubator and accelerator programs around the world. He's a Professor of Entrepreneurship at the University of Southern California (USC), and he's the author of Growth Units: Learn to Calculate Customer Acquisition Cost, Lifetime Value, and Why Businesses Behave the Way They Do. This episode is a crash course to help you understand and calculate your customer acquisition cost, lifetime value, retention, and churn (including negative churn and why that's a great goal for your SaaS business). We cover the common mistakes that founders make when working with these metrics and share some best practices to help you be more successful. By the end of this episode, you should have more confidence in understanding those metrics and how to use them to help you drive business growth. I hope you enjoy it.

How Carrd Hit $1M ARR with Just 2 People - AJ

AJ, Carrd

How Carrd Hit $1M ARR with Just 2 People

AJ is the founder of Carrd, a SaaS platform for building simple and fully responsive one-page websites. After years of building and selling website templates, AJ created Carrd as a side project—a simple one-page website builder that he hoped would pay for his coffee habit. He launched with a freemium model and $19/year pricing, expecting modest results. By 2020, he had bootstrapped to $30K in monthly recurring revenue without any marketing spend beyond building in public on Twitter. Then 2020 happened. COVID drove people online. Political activists discovered Carrd. Kim Kardashian tweeted a Carrd site. Growth exploded. Suddenly, AJ's side project was hosting millions of websites and facing infrastructure that would collapse within months. He had two choices: keep treating it like a side project, or get serious about building a real company. He chose the latter. But there was a problem: AJ had never run a company at this scale. He didn't know how to hire, how to manage infrastructure for millions of users, or how to handle the legal complexity of a platform used by activists. That's when he made the unconventional decision to raise $2M—not because Carrd needed the money (it was profitable), but because he needed a network of advisors who had been there before. In this interview, AJ shares how he scaled from $30K to over $100K in monthly recurring revenue while keeping the team at just 2 people, why he finally decided to hire his first developer, and the lessons he learned about staying lean while growing a bootstrapped SaaS business.

IPinfo: Bootstrapping a Side-Project to a 7-Figure SaaS - Ben Dowling

Ben Dowling

IPinfo: Bootstrapping a Side-Project to a 7-Figure SaaS

Ben Dowling is the founder of IPinfo, a web service that provides IP address data for thousands of businesses and developers. In 2014, Ben was writing code for a project at work and found himself wasting a lot of time looking up information about IP addresses. So he built a simple API to help make his life easier. He posted about it on Stack Overflow so other developers might also save some time. His API turned out to be quite popular, so a year later, he added a paid plan. And he was blown away when someone signed up for $50 a month. Ben continued working his day job and slowly started adding new customers to his API side-project. Two years later, his API was generating over $100K a year. And that's when he finally quit his job and started working on his business full-time. He figured that without any distractions, his company could grow even faster. But instead of growing faster, his business stopped growing for some time. It didn't make much sense, and Ben struggled to grow his business for some time. He also made some fundamental mistakes along the way. For example, he allowed people to use his API without ever signing up. While that made it easy for people to use the product, he couldn't even market to those people or even contact them about outages. Today, his API project has grown into a multi-million SaaS company with a team of 15 people. The API handles 40 billion requests a month, and its customers include companies like T-Mobile, Datadog, and Demandbase. In this interview, we explore how Ben grew his business, why it stopped growing when he went full-time, and how he overcame some of the critical mistakes he made. I hope you enjoy it.

The Reality of Building a  Slow Burn SaaS Business - Michael Kansky

Michael Kansky

The Reality of Building a Slow Burn SaaS Business

Michael Kansky is the founder of LiveHelpNow, a customer support platform that provides small businesses with help desk, live chat, and more. In 1997 Michael immigrated to the United States from Ukraine as a refugee. To help himself get a job, he signed up for a computer programming course. As a final project, he built a dating website. And people started using the site. At one point, he had around 1,000 users. When a user asked for an easier way to communicate with other users, Michael built a basic chat feature, which he also started using to support end-users. In 2005, he realized there was a growing opportunity with live chat, so he took what he'd learned and launched a new product. But it was a complete hobby. Michael had no business plan or customers. But he loved building the product and seeing people use it. Eventually, in 2009 in started charging for his live chat product. About a third of his customers switched to a paid plan – which generated around $10K MRR. Today, Michael has bootstrapped his business to over $3 million ARR, but it took him 12 years to get there. And for the last 4 years, revenue has been flat. We often hear stories of entrepreneurs who launch a product, spend no money on marketing, and hit their first million dollars almost overnight. But that's not the experience for the majority of SaaS founders. Michael's story is about the reality and the long hard slog that most founders have to go through to find success. In this interview, we talk about the realities of building a SaaS business, the big lessons Michael's learned, and what he's doing to start growing again. I hope you enjoy it.

Veed.io – Lessons on Bootstrapping a SaaS to $2M ARR - Sabba Keynejad

Sabba Keynejad

Veed.io – Lessons on Bootstrapping a SaaS to $2M ARR

Sabba Keynejad is the co-founder of Veed.io, a UK based SaaS startup that provides a simple online video editing platform. I originally interviewed Sabba about 9 months ago on episode 241 where we talked about how he and his co-founder Tim had struggled to get their SaaS business off the ground. They weren't able to raise funding so had to work contract jobs during the day and on their startup in the evenings and weekends. They made it to the final YC interviews, flew out to the US but were rejected because they weren't making any money. And a few months later they were on the brink of shutting down with just about one month's runway left. In episode 241 we talked about how Sabba and Tim dealt with each failure and kept going. And at the time the founders had managed to start generating about $10K in MRR. Recently I was in touch with Sabba and discovered in the last 9 months, they've grown their SaaS business from just over $100K to over $2 million in ARR. So obviously I wanted Sabba to come back on the show and talk about how they've been able to grow their bootstrapped business so fast in less than a year. We talk about the importance of building a great product, how to decide on the right features to build, creating a frictionless experience, the specific growth tactics that helped them grow faster, and one critical ingredient that you must have to make everything else work. I hope you enjoy it.

DocSend: A Case Study in Product-Led Growth - Russ Heddleston

Russ Heddleston

DocSend: A Case Study in Product-Led Growth

Russ Heddleston is the co-founder and CEO of DocSend, a SaaS platform that lets you securely share your documents with real-time control and insights. When Russ was an intern at Dropbox, he found that many people still shared files as email attachments even though it wasn't secure or easy to track. He decided to change that. Being engineers, Russ and his co-founders wanted to build a product right away, but they resisted the temptation. Instead, they decided to meet with potential customers to get feedback on their product idea, which resonated with a lot of people. Once they'd had enough customer conversations, they built DocSend as quickly as possible, putting little effort into design or marketing. And to get the word out, they gave away free accounts in exchange for feedback. It didn't take long for DocSend to become a quick success. But they weren't charging anything for the product. As DocSends' growth continued, the founders realized they needed to change their model. It was hard to keep growing without any revenue, so they created a $10 a month plan and they kept growing. In 2016, the founders built a sales team to help generate more demand. While it felt like the right move, their sales efforts failed. Eventually, they gave up on doing outbound sales and instead went all-in with a self-serve model just two years later. The team increased its prices and reworked the product positioning but didn't actually make any changes to the product. Suddenly, their most expensive plan was the most popular. The more they charged, the better they seemed to do with free to paid conversions. Today, DocSends' growth is driven primarily by word of mouth and SEO, and the team continues to focus relentlessly on building a great product. To date, they've raised over $15 million dollars and have a team of around 55 people. This story is a great example of how to learn from your mistakes and why product-focused models can succeed. I think you'll find it interesting and insightful in many ways. In this interview we talk about:

Chili Piper: How to Pre-Sell and Bootstrap a SaaS to Profitability - Nicolas Vandenberghe

Nicolas Vandenberghe

Chili Piper: How to Pre-Sell and Bootstrap a SaaS to Profitability

Nicolas Vandenberghe is the co-founder and CEO of Chili Piper, a SaaS platform that helps you instantly turn inbound leads into qualified meetings. Nicolas grew up in France and wanted to travel around the world. He applied to Stanford so he could live in California for a couple of years before continuing his travels. But all his plans changed when one day Steve Jobs gave a talk to his class. Nicolas was so inspired that he decided he was also going to become a tech entrepreneur. Ironically, Nicolas's first startup was co-founded with John Sculley, the guy who became CEO of Apple and eventually fired Steve Jobs. Nicolas's latest startup Chili Piper was founded when he and his wife identified a niche problem with companies losing leads because they couldn't respond quickly to inbound leads. He wanted to be sure he was solving a worthwhile problem, so he told his first potential customer that he could build them a solution for $20,000. The customer paid him upfront. And that's how they got started. But like most startups, when you look deeper you also discover a bunch of problems and challenges. And it was no different for Nicolas. He said most people wake up and check their email every morning, but he used to check his bank account and worry if they had enough pay to pay the bills. And at one point, he ran out of money and couldn't pay his employees. However, despite those challenges, they bootstrapped the company from zero to over $5M in annual recurring revenue (ARR) and recently raised $18 million in funding. It's a great conversation with a serial entrepreneur who shares a lot of useful insights. I think you'll find this story inspiring and entertaining.

SaaS Product-Led Growth and the New Customer Journey - Blake Bartlett

Blake Bartlett

SaaS Product-Led Growth and the New Customer Journey

Blake Bartlett is a partner at Openview, a venture capital firm that focuses on B2B companies in the expansion stage such as Highspot, Calendly, and Expensify. These days it seems like everyone in SaaS is talking about product-led growth (PLG). But for many critics, it's just a buzzword and for others, it's not even a new concept. So I decided to sit down with the guy who actually coined the term product-led growth and explore this topic in more depth with him. If you're not familiar with product-led growth, then I'd suggest you listen to episode 251 where I cover the fundamentals of PLG with Wes Bush (founder of Product-Led Institute). In this interview with Blake Bartlett, we build on that and answer questions like: We also explored how a fictional sales-led SaaS company might transition to a product-led growth model. And we examined some of the challenges the company would face trying to do that and how it might overcome them. I think it's a great conversation with someone who thinks deeply about product-led growth all the time and is involved in a number of PLG focused B2B SaaS companies. I hope you enjoy it.

Qwilr: SaaS Freemium Pitfalls and How to Avoid Them - Mark Tanner

Mark Tanner

Qwilr: SaaS Freemium Pitfalls and How to Avoid Them

Mark Tanner is the co-founder and COO of Qwilr, a SaaS product that helps you create design-perfect proposals, quotes, client updates, and more. This story starts in 2013 with a designer/developer named Dylan. He was running a micro-agency and found himself wasting a lot of time creating proposals. Like any self-respecting designer, he wanted to create beautiful proposals. But that meant a lot of work and back-and-forth using Word, Excel, and Adobe InDesign. One day, out of frustration, he created a website as his proposal doc. Not only did he get hired, but the client loved the website proposal and was impressed by how quickly he'd built a website for them. And that's how the idea for Qwilr was born. Dylan and Mark teamed up and decided to give this business idea a try for a couple of months. They wanted to learn if they could find their first 10 customers. In this interview, you'll learn how they turned that 2-month experiment into a business with 45 employees, $7.5M in funding, and around 3,000 customers. We also talk in-depth about the pros and cons of a freemium business model. And you'll learn about the mistakes, failures, and successes that Qwilr had with their freemium plans. We also identify some important considerations you have to make before choosing a freemium model and how you can avoid making some of the same mistakes Dylan and Mark did. I hope you enjoy it.

Hull: A SaaS Startup That Went from Failure to Successful Pivot - Romain Dardour

Romain Dardour

Hull: A SaaS Startup That Went from Failure to Successful Pivot

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. I hope you enjoy it.

A Guide to Product Led Growth for SaaS Founders - Wes Bush

Wes Bush

A Guide to Product Led Growth for SaaS Founders

Wes Bush is the founder of Product Led Institute and author of the book Product Led Growth: How to Build a Product That Sells Itself'. Product-Led Growth (PLG) is a term coined by the VC firm Openview Venture Partners and is a growth-model that relies on the product as the main vehicle to acquire, activate, and retain customers. In this interview, you'll learn about the 3 tidal waves or trends that are forcing more and more SaaS companies to focus on product-led growth as the main growth driver. You'll learn the differences between a sales-led' approach and a product-led' approach and we'll help you understand which one is right for your SaaS company. We talk about the pros and cons of using free trials versus a freemium model, and you'll learn how to pick the right one for your go-to-market strategy. And we'll teach you the MOAT framework, which will help you figure out the right marketing strategy, understand if you're in a red or blue ocean business, determine if a top-down or bottom acquisition strategy is right for you and how you can help showcase value to new users and customers as fast as possible. You'll also learn about the Bowling Alley framework and how it can help you improve your onboarding process.

6 PPC Mistakes SaaS Companies Make (and How to Avoid Them) - Todd Chambers

Todd Chambers

6 PPC Mistakes SaaS Companies Make (and How to Avoid Them)

Todd Chambers is the director and founder of Upraw Media, an Amsterdam based agency that helps SaaS companies to grow and scale using paid media.

A SaaS Founder Shares His Lessons on Overcoming Failures - Sabba Keynejad

Sabba Keynejad

A SaaS Founder Shares His Lessons on Overcoming Failures

Sabba Keynejad is the co-founder of Veed.io, a UK-based SaaS startup that provides a simple online video editor. Sabba and his co-founder Tim were frustrated working with complex and time-consuming video editing software. They realized that for many tasks, these products were overkill. So they set out to build a simple online video editing tool. They failed to raise seed funding so they had to work contract jobs during the day. And then they worked on their business at night. A few months later they applied to YC and made it to the final interview. They flew out to the YC offices in Mountain View excited to be on a cusp of a big break. But they were rejected by YC because they weren't making any money. So 48 hours later, the founders implemented a paywall and had their first 20 paying customers. It was a promising sign that they were solving a worthwhile problem, so they kept going. But by August, they had less than one month's runway left and knew they were going to struggle to make payroll. So they doubled their prices with little to no impact on user growth. Today, they're generating over $10K in MRR and are growing 50% month over month. The key takeaway from this story is that failure is part of life. It's how you bounce back that matters. I hope you enjoy it.

Freemium Model for SaaS: Lessons from a Startup Founder - Sam Dolbel

Sam Dolbel

Freemium Model for SaaS: Lessons from a Startup Founder

Sam Dolbel is the co-founder and CEO of SINC, a SaaS product, and a mobile app that helps companies manage their mobile workforce by taking care of timesheets, location tracking, staff scheduling, and job tracking. In 2017, Sam was running a small business in New Zealand. He had 10 employees and found himself spending several hours every week managing payroll. He reached out to a friend and asked him if he could help him create a spreadsheet that might help him save some time and make dealing with payroll easier. Sam's friend suggested that they build an app. It sounded like a great idea. The only trouble was that his friend (who was a mechanical engineer) didn't know how to code either. And at the time, his friend was filming a documentary in Africa. But he had some time, so he started learning how to code while living in a tent in Tanzania. A couple of months later, the app was ready and Sam was using it in his business. Once they realized the value of the app, they decided to join forces and launch it as a product. In this interview, we talk about: Today, SINC has over 1,000 paying customers and the founder's journey is a really interesting story. I hope you enjoy it.

Elastic.io: Getting Traction by Charging More for Your SaaS - Renat Zubairov

Renat Zubairov

Elastic.io: Getting Traction by Charging More for Your SaaS

Renat Zubairov is the CEO and co-founder of Elastic.io, a hybrid integration platform that helps businesses connect APIs, and on-premise and cloud applications quickly and securely. In 2012, Renat and his co-founders were working for a company where they were doing a lot of integration work. They realized that they weren't the only ones feeling the pain. Eventually, they came up with an idea to build a SaaS integration platform. They used their savings to start their company and spent the first six months building a product. But they didn't talk to any customers. So when they eventually launched, it was hard for them to find customers. Even giving away the product for free didn't help much. But when they started charging for their product, something interesting happened. They started attracting better quality customers. And the feedback they got from those customers allowed them to build a better product and serve those customers better. They realized that they could charge even more for their product by targeting larger companies. Today, a typical customer pays them around $10K a year and they're currently doing around $2.5 million in annual revenue. And they've been growing over 100% year over year (YOY) for the last 3 years. Renat shares the story of how they've built Elastic.io, what they've been doing to grow so fast, how he wishes that they'd charged much earlier for their product and the impact of not thinking big enough when they started. I hope you enjoy it.

Typeform: A Case Study in Product-Led SaaS Growth - David Okuniev

David Okuniev

Typeform: A Case Study in Product-Led SaaS Growth

David Okuniev is the co-founder of TypeForm, a Barcelona-based SaaS company that specializes in online form building and online surveys. David and Robert were running a small design agency in Barcelona. A client asked them to create a form that could be used to collect information about people attending an exhibition. Instead of building a regular old form, they wanted to do something different. And inspired by the 1980s movie War Games, they created something a form that was more conversational. After that project was over, they talked about turning that idea into a product. But they weren't in a particular rush. And they spent the next 2 years trying to build the right product. When they were almost ready to launch the beta, they put up a landing page and promoted it on Betalist. In a few weeks, they had collected around 5000 email addresses. When they launched the beta, people started creating and sharing forms. And when they shared a form, new people discovered the product, signed up and created their own forms. The product that they'd spent years trying to get right was quickly going viral. In fact, when they introduced a paid plan, it took them about a year to get to a million dollars ARR. The interesting thing about Typeform is that the founders didn't start with a niche market. They built a product for everyone — which is counter-intuitive to what the majority of startups do. Today, their business does around $30M in ARR and employs around 200 people. In this interview, we talk about why the founders focused so much on building a great product, why design and user experience were more important to them than customer development or marketing and how they have grown Typeform into an 8-figure business. We also talk about a new product they've recently launched called VideoAsk and they're once again building a unique online form and survey experience with a different product. I hope you enjoy it.

What to Do When No One Will  Pay for Your SaaS Product - Ryan Born

Ryan Born

What to Do When No One Will Pay for Your SaaS Product

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.

How Carrd’s Founder Turned a Side Project into a Profitable SaaS - AJ

AJ

How Carrd’s Founder Turned a Side Project into a Profitable SaaS

AJ is the founder of Carrd, a SaaS platform for building simple and fully responsive one-page websites. In 2012, AJ was designing and creating website templates and themes for a living. Around that time, responsive web design was growing in popularity and it was a skill AJ wanted to acquire. So he set out to design and build his first responsive site template. When it was done, he put it on his website and let people download it for free. People liked his template, so he kept building more. And people kept downloading those templates and using them to build websites. Some people started asking if they could pay him for additional features and support. So he started charging them effectively a one-time payment of $19. It wasn't a lot of money, but he'd been doing such a great job creating so many templates and built a loyal following that he was quickly generating 6-figures in annual revenue. But by 2015, AJ was bored of building templates and themes. It had been fun learning a lot of new skills. But he was now ready for a new challenge. He was intrigued by the idea of site building software that made it easy for non developers to create websites. But companies like Wix and Squarespace already had products in the market. He knew he couldn't compete with those companies. So he looked for a different way. And eventually, he narrowed down his idea to a site builder for really simple one-page websites. And it turned out to be a good idea that caught on with a lot of people. Today, his business is doing around $30K in monthly recurring revenue (MRR) and is profitable. In this interview, we talk about how he's built a one-person SaaS company with no marketing. But he's a great guy and I had a lot of fun talking to him. I hope you enjoy it too.

How Josh Ho Bootstrapped His SaaS from Zero to $70K MRR - Josh Ho

Josh Ho

How Josh Ho Bootstrapped His SaaS from Zero to $70K MRR

Josh Ho is the founder and CEO of Referral Rock, a SaaS product that helps businesses to design, launch and manage a customer referral program. You've got a great idea for a SaaS product, but no one else seems as excited about it. Does that mean it's a bad idea and you should move on to something else? Not necessarily. In 2013, Josh was at a car dealership waiting for his car to be serviced. He overheard a conversation which got him curious about how brick and mortar companies like car dealerships got referrals and if there was a way to automate word of mouth referrals. He did some research that evening and thought he'd found a gap in the market. He was excited about his idea, but he didn't like what he heard when he interviewed prospective customers. No one seemed excited about his idea. But being a bit stubborn, he decided to build an MVP anyway. He kept things really simple and cobbled together a few different tools and technologies to quickly build an MVP. And he started getting the word out anyway and every way he could. And slowly he started getting people signing up for his product. About 18 months later, he had around 500 users signed up. But there was one big problem. Josh wasn't charging any money for his product. He had hundreds of users but no customers and no revenue. One day, a close friend told Josh something that he needed to hear. He didn't have a real business until he was charging for his product and generating sales. So reluctantly that weekend, he added a paid plan. And to his surprise, a week later he had his first customer paying him $59 a month. Today, Josh runs a 100% remote company with 12 full-time employees and he's generating $70,000 in monthly recurring revenue. And his business is totally bootstrapped. At every step, he kept second guessing himself and questioning how big his business could become. But he kept executing, trying new things and taking action. There was no magic bullet or hack that helped him grow. He kept doing small things to see what worked and if they did, they figured out how to scale them. And that's what he's still doing today. It's a great story and Josh talks candidly about his successes and failures. I hope you enjoy it.

How to Grow Your SaaS Startup with Facebook Ads - Aaron Zakowski

Aaron Zakowski

How to Grow Your SaaS Startup with Facebook Ads

Aaron Zakowski is the founder of Zammo Digital, a marketing agency that specializes in using Facebook ads to help SaaS companies grow and scale their businesses. His clients include companies such as InVision, Digital Ocean and Treehouse. Have you struggled to make Facebook ads work for your SaaS business? Maybe you read every blog post you could about Facebook ads. You identified your target audience and put together great copy and images for your ads. And then when everything looked good, you put the campaign live. Facebook quickly started eating up your advertising budget, but your investment didn't turn into many leads or sales. If that's happened to you, then you're not alone. A lot of SaaS companies struggle to make Facebook ads work. And many B2B companies dismiss Facebook ads because it's a B2C platform. But with the right knowledge, mindset and approach you can use Facebook ads to generate leads and sales for your SaaS business.

SaaS Funding: A Different Way to Finance Your Startup

SaaS Funding: A Different Way to Finance Your Startup

BJ Lackland is CEO of Lighter Capital, a Seattle based company that specializes in providing financial capital to early-stage SaaS companies. Let's say your SaaS company is generating revenue… Your business is still in the early stages and you want to raise money to help you grow faster. But you know that raising angel or VC funding is going to take a lot of time and effort. You're already busy enough working on your business, product, and marketing. You know you need to raise money, but how are you also going to find the time to do fundraising? Well, there's another way to finance your startup that you might not have considered. It's called revenue-based financing and it allows you to quickly and easily raise funding without giving up equity or providing personal guarantees.

SaaS Pricing Strategy: Top 5 Mistakes to Avoid - Kyle Poyar

Kyle Poyar

SaaS Pricing Strategy: Top 5 Mistakes to Avoid

Kyle Poyar is the of VP Market Strategy at OpenView, an expansion stage venture capital firm that helps build software companies into market leaders. Your SaaS pricing strategy can make or break your business. But getting your pricing right is really hard. And many companies struggle to understand what they're worth to their customers and how to clearly communicate that.

Bootstrap and Sell a Profitable Micro-SaaS Company - Tyler Tringas

Tyler Tringas

Bootstrap and Sell a Profitable Micro-SaaS Company

Tyler Tringas is a General Partner at Earnest Capital which provides early-stage funding for bootstrappers. So you want to start a SaaS company. And people keep asking you how big the market opportunity is and if your idea will scale. But maybe you don't want to build a huge business. Maybe you just want to create a sustainable and profitable business that gives you more freedom. In 2011, Tyler quit his job to start a venture-backed software startup called SolarList. He was a first-time founder and non-technical. So he also started learning how to code. Getting his startup to take-off was slow going, so he started doing some freelance work. Several of his clients wanted a way to add store locator functionality to their websites. So on a 30-hour flight from San Francisco to Buenos Aires, Tyler built a store locator SaaS app as a side-project. When he landed, he deployed the code and launched the product. He emailed some of these clients and within 24 hours he had a handful of people paying him $5 a month. The product was terrible and had a lot of missing functionality, but it did the basic job. A year later, SolarList still wasn't getting traction and had to be shut down. And Tyler was left with over $50,000 of credit card debt and uncertainty about his future. He had to dig himself out of a financial hole. So he started doing more freelance work and putting more time into his StoreMapper side-project which was now doing around $1000 MRR. By being able to spend more time on StoreMapper, Tyler was able to grow it over $5000 MRR in about 9 months. And eventually got it to over $40,000 MRR a few years later. But he built it as a sustainable and profitable micro' SaaS company. It helped him to pay down his credit card debt, travel the world and spend more time on projects he found interesting. And if building that type of business appeals to you, then you'll love this episode. I hope you enjoy it.

How to Create a SaaS Offer Your Prospects Can’t Refuse [200] - This

This

How to Create a SaaS Offer Your Prospects Can’t Refuse [200]

This is a special episode and I have three guests on the show today! Jimmy Ellis and Chris Rizzo are the co-founders of Prospecting Hub, a performance-based marketing firm. They generate leads for companies but only get paid when the lead is closed. Charles Kelly is the founder and CEO of Logic54, a SaaS platform, and service that helps school districts to run more efficient bus routes and save money.

How a Founder Went From a Failed SaaS Business to $250K MRR - Dave Rogenmoser

Dave Rogenmoser

How a Founder Went From a Failed SaaS Business to $250K MRR

Dave Rogenmoser is the co-founder and CEO of Proof, a SaaS product that helps build social proof and increase conversion rates by displaying recent customer activity on your website. Dave started as an entrepreneur about 5 years ago. He paid a developer on Upwork $10,000 to build a software product, but he didn't know how to get customers and so the business quickly failed. He started learning as much as he could about marketing. And as he developed those skills, he was able help local businesses get more customers. So he started an agency. But he quickly realized how much he hated the agency life. Next he and his co-founders launched an information publishing business and sold courses and coaching. But deep down, he still longed to have a software business with recurring revenue. One weekend, Dave and his co-founders built a widget for their website to help them sell more courses. The widget showed you names of people who had just purchased the course. It was social proof and it doubled their sales almost overnight. Dave started testing this widget on his friends websites. And they all reported back positive results and improved sales conversion rates. And that's how Proof was born.

The Single Founder Who Bootstrapped a $50 Million SaaS Company - Jason VandeBoom

Jason VandeBoom

The Single Founder Who Bootstrapped a $50 Million SaaS Company

Jason VandeBoom is the founder and CEO of ActiveCampaign, an email marketing, marketing automation and sales CRM platform. Jason was doing consulting work as a developer. He decided to move to Chicago and study fine arts at college. He started looking for ways to do less consulting so he had more time for college. At the time he'd been building email marketing solutions for a number of clients. So he decided to package up that work into an email marketing product that he could sell. This was an on-premise product (not SaaS) so clients had to install the software on their own computers. He continued with the on-premise software model. But growth was slow. After 10 years his business was generating a couple of million dollars in revenue and was profitable. And then decided to bite the bullet and switch to a SaaS model. He was potentially risking all his existing revenue. But looking back, he wishes that he'd done it sooner and didn't overthink things. The real growth for ActiveCampaign has happened in the last 2 years — after 13 years of slow growth. The company now has over 60,000 customers and generates over $50 million a year in revenue. And it employs over 300 people. Jason raised $20M in 2016, but bootstrapped and self-funded the business for the first 13 years. And so far, he hasn't used any of the money he raised. And he's a single founder. You've probably heard things like — you can't succeed unless you find a co-founder or jump into working on your business full-time from day one.

Challenges of Scaling a SaaS Business to $20 Million - Rick Perreault

Rick Perreault

Challenges of Scaling a SaaS Business to $20 Million

Rick Perreault is the co-founder and CEO of Unbounce, a SaaS product that makes it easier to build custom landing pages, improve conversion rates and drive more leads & sales. The company was founded in 2009 and went from zero to over $7 million dollars in annual revenue within 5 years. Rick was an early guest on this podcast (on episode 25 back in 2014) where he shared what happened in those 5 years. Since then, Unbounce has continued to grow and is now a $20 million dollar business. So I invited Rick back to talk about the challenges of scaling a SaaS business.

Scaling Your SaaS Subscriptions and Billing

Scaling Your SaaS Subscriptions and Billing

Krish Subramanian the co-founder and CEO of Chargebee, a platform that automates subscription management and billing for SaaS and e-commerce businesses. Chargebee was founded in 2011 and is based in Chennai, India. To date, the founders have raised $6 million in funding but bootstrapped the business for the first year and a half. We talk about the challenges faced by businesses in managing their SaaS subscriptions and recurring billing scenarios. And we explore how Chargebee is solving those problems and helping SaaS businesses to reduce customer churn. The founders knew that they wanted to work together, but it took them 10 years to save enough money and have the courage to finally take the leap and quit their jobs. And then it took them over a year to launch their MVP because they tried to build too many features. We talk about the lessons they learned from this experience and how they'd do things differently now. We also explore what it's like to build a SaaS business in India. You don't have the benefits of being in Silicon Valley and you're trying to convince SaaS and e-commerce businesses around the world to manage their revenue with your platform. And they faced a lot of resistance and challenges along the way. We talk about how they overcame those challenges and what they've done to get over 6000 companies around using their platform.

The 4-Step SaaS Sales Process to Hit Your Company Goals This Year - Jim Brown

Jim Brown

The 4-Step SaaS Sales Process to Hit Your Company Goals This Year

Jim Brown is a sales coach, founder of Sales Tuners and the host of the Sales Tuners podcast. He's spent the last 10 years helping lead two companies from $1M to more than $10M in annual revenue. And has a founder he took another company from $1M in funding to zero. Today, he coaches tech companies and salespeople through his Skeptical Selling Method. And on his weekly podcast, he talks with great sales leaders and high performing individual salespeople about the behaviors, attitudes, and techniques that have lead to their success. This interview is a story about a sales guy who spent 10 years helping to lead two companies to over $10M in annual revenue. Then as founder, he took another company from $1M in funding to zero. Yup, you read that right. He shares with me some important but tough lessons he learned from that experience. And we talk about how losing other people's money was one of the hardest challenges that he has faced in his career. There are a lot of stories about how a founder went from zero to a multi-million business. And those stories are great because we can learn from those entrepreneurs and their successes. But it's equally important to learn from business failures. And I'm fortunate enough to have a guest today, who's willing to sharing it all. My guest also shares his sales expertise and takes me through a simple but powerful 4 step process to help you achieve the sales goals for your SaaS business this year. We do a deep dive into that process so you might want to be ready to take some notes.

How a High-School Teacher Earned $5 Million With Online Coding Courses - Rob Percival

Rob Percival

How a High-School Teacher Earned $5 Million With Online Coding Courses

Rob Percival is a former high school math teacher from England who started teaching people to code. He posted his first online web development course for $199 in June 2014 and only made 1 sale in the first 24 hours. Since then he's gone on to launch several coding courses with well over 500,000 students and has generated over $5 million in revenue. You can find his online courses at Udemy.com. The topics range from web and mobile development courses to Ruby on Rails & Python programming and database development. He's also the founder and managing director of Eco Web Hosting, a company that focused on environmentally friendly web hosting and packages that are 100% carbon neutral.

How Design Pickle Bootstrapped Its Way to $2 Million Revenue - Russ Perry

Russ Perry

How Design Pickle Bootstrapped Its Way to $2 Million Revenue

Russ Perry is the founder of Design Pickle, a productized service that offers unlimited graphic design support for your day-to-day business needs for a flat monthly fee. Design Pickle launched in January 2015. And in just two years, it's grown it into a business with 45 full-time staff and $160K on monthly recurring revenue (MRR). Russ was running a creative agency but wasn't entirely happy with what he was doing. He thought that the agency business model was dysfunctional and he wanted to run a more predictable business. But he didn't have a clue what that business was going to be. He made a list of what he wanted in his life, both personally and professionally. And he also started to get clear about what type of business he didn't want to build. And then he sat back and waited for inspiration, while he did consulting on the side to help pay the bills. And a few weeks later, he had his 'aha' moment. And it was a very simple idea. He decided to launch a design agency and used a 'productized consulting' model — very similar to how pricing for a SaaS product works. In 2 years, he's gone from zero to $160,000 in monthly recurring revenue (MRR). That's almost $2M annual run rate (ARR). And he now has a team of 45 full-time employees. It's an inspiring story, and he's an energetic and entertaining guy. I hope you enjoy this interview.

How Prospectify Grew SaaS Revenue from Zero to $20K MRR in 9 Months - Matt Ekstrom

Matt Ekstrom

How Prospectify Grew SaaS Revenue from Zero to $20K MRR in 9 Months

Matt Ekstrom is the co-founder of Prospectify, a B2B prospecting platform that helps you to automate your lead generation process. Prospectify uses data search, data enrichment, and verification systems to help you build highly targeted prospect lists. The company was founded in January 2016 and was self-funded for the first year. At the end of 2016, the company raised $1 million in funding.

How to Implement a Successful SaaS Business Model - Antonio Carlos Soares

Antonio Carlos Soares

How to Implement a Successful SaaS Business Model

Antonio Carlos Soares is the co-founder and CEO of RunRun.it, a SaaS product that helps teams to manage tasks, projects, performance and corporate communication. The company was founded in 2012, is based in Sao Paolo, Brazil and to date has raised $4.4 million in funding. RunRun.it has more than 1000 paying customers and generates over $2 million in annual recurring revenue (ARR). Antonio is a serial entrepreneur from Sao Paulo, Brazil. He quit a successful consulting career to build his own startup. Like most entrepreneurs, he had a roller coaster of a ride. He had tough moments such as having to put this mother’s apartment up as collateral for a business loan. And he had highs by successfully building and selling a business. Since 2012, he's taken RunRun.it from zero to over $2 million in annual recurring revenue, 1000 customers, and over 65 employees.

How to Develop Your SaaS Pricing Model the Right Way - Patrick Campbell

Patrick Campbell

How to Develop Your SaaS Pricing Model the Right Way

Patrick Campbell is the co-founder and CEO of Price Intelligently, a Boston based startup that helps SaaS businesses to come up with the right pricing strategy. The company gathers data from multiple industry sources and uses its proprietary algorithms to help SaaS businesses figure out how much customers are willing to pay for each feature and how to optimize their overall pricing plans. Price Intelligently employs about 30 people and their customers include companies such as Wistia, Big Commerce, Optimizely, Zapier and more. The company was founded in 2012 and has been bootstrapped from day one.

How a Bootstrapped SaaS Startup Made Its First Million Dollars - Ryan O'Donnell

Ryan O'Donnell

How a Bootstrapped SaaS Startup Made Its First Million Dollars

Ryan O'Donnell is the co-founder of SellHack, an online platform for salespeople that helps them find targeted prospects, build email lists and verify email addresses. He started his career on Wall Street as a broker making 500 calls a day prospecting for new clients. He decided to follow his passion for tech and joined Right Media, which was later acquired by Yahoo. After spending 3 years at Yahoo, he left and began his startup journey. SellHack was founded in 2014 and is based in Cleveland, Ohio.

Maximizing Your SaaS Customer Lifetime Value - Aseem Badshah

Aseem Badshah

Maximizing Your SaaS Customer Lifetime Value

Aseem Badshah is the co-founder and CEO of Socedo, a platform for sales teams that helps them generate relevant leads based on social media data. The company was founded in 2012 and has raised $1.5 million to date. Before launching Socedo, my guest founded and ran Uptown Treehouse, a digital marketing agency for Fortune 500 brands that focused on social media. Aseem shares how learned to maximize customer lifetime value (CLV) by asking his customers.

How to Turn Frustration Into a Million Dollar Software Business (Part 1) - The idea for Thrive Themes came from Shane's own frustrations with building marketing websites. He was having a frustrating experience trying to build lead generation and sales pages on WordPress.
He often had to use multiple plugins and different WordPress themes to cobble together what he needed. And often all these plugins didn't work together well and created a poor user experience.
WordPress

The idea for Thrive Themes came from Shane's own frustrations with building marketing websites. He was having a frustrating experience trying to build lead generation and sales pages on WordPress. He often had to use multiple plugins and different WordPress themes to cobble together what he needed. And often all these plugins didn't work together well and created a poor user experience. WordPress, Thrive Themes

How to Turn Frustration Into a Million Dollar Software Business (Part 1)

"It's very possible to hire someone to build a piece of software, that's technically a piece of software, but not usable in any way." "Validating an idea with money in the bank, is the best type of validation." "I've often used writing as a learning tool."

How a Developer Turned a Failing Startup into a Profitable Business - Jay Gibb

Jay Gibb, CloudSponge

How a Developer Turned a Failing Startup into a Profitable Business

Jay Gibb is the co-founder and CEO of CloudSponge, a product that helps businesses to acquire more users via their email referral forms. Most referral forms ask you to type in your friend's email addresses. With CloudSponge it's possible to give users access to their contacts directly from your website. The company was founded in 2010, is self-funded and its customers include companies such as Lyft, Yelp and AirBnB. We discuss how Jay started out with $100K and a small team to build the 'ideal' product. They blew most of that money and still didn't have a product in market. Jay knew that he either had to quit or pivot. They needed a 'plan B'. So they took ONE feature from the product they were building and turned it into a standalone product. They had a crappy website up in less than a week and started charging right away. Today, that startup has an annual run rate of over $500,000 and is profitable.

5 Steps to Crafting Your Startup’s Online Sales Funnel - Jeremy Reeves

Jeremy Reeves, lempire: From $1K Launch to $26M ARR Profitable SaaS - with Guillaume Moubeche [405]

5 Steps to Crafting Your Startup’s Online Sales Funnel

Jeremy Reeves is a sales funnel expert. He specializes in building strategic and automated online sales funnels that help his clients generate more revenue. He created millions of dollars in additional profits for his clients.

How This Bootstrapped Startup Went from Zero to $55K a Month

How This Bootstrapped Startup Went from Zero to $55K a Month

Mogens Møller is the co-founder and CEO of Sleeknote. A SaaS product that helps eCommerce sites get more email opt-ins, without affecting bounce rate and sales. The company was founded in 2013 and is based in Aarhus, Denmark. Sleeknote currently has around 700 customers and generates $55,000 in monthly recurring revenue. And the business has been bootstrapped from day one.

How Brandon Pearce Bootstrapped a Startup from $0 to $70K a Month - Brandon Pearce

Brandon Pearce, Treehouse: How a Developer Bootstrapped an 8-Figure SaaS Company - with Ryan Carson [246]

How Brandon Pearce Bootstrapped a Startup from $0 to $70K a Month

Brandon Pearce is the founder of Music Teachers Helper, a SaaS application that's helping thousands of music teachers around the world manage their studio. It lets them handle everything from billing and lesson schedules to automatic reminders and even tax reports. I first came across my Brandon in 2012 when I read his story in a book called The $100 Startup by Chris Guillebeau. He started the business with almost no money in 2004 and within a few years, the business was generating almost $30,000 in MRR. So he decided to sell his home and belongings in Utah and moved with his wife and 2 young daughters to Costa Rica (where his third daughter was born). And in the past 6 years, they've visited over 30 countries, while still building his business.

How George Palmer Bootstrapped His Profitable Startup with Just $50 - George Palmer

George Palmer, SendOwl

How George Palmer Bootstrapped His Profitable Startup with Just $50

George Palmer is the founder of SendOwl, a platform that makes it easy to sell digital products online. He founded the company as a side-project in 2011 while he was still working as a Ruby on Rails freelancer. And within 2 years was able to start working on it full-time. He spent less than $50 to start the business and has bootstrapped it from day one. Today SendOwl has 4 full-time employees and is profitable.

Part 2 – How StatusPage Went from Zero to a Million Dollars in 18 Months - Scott Klein

Scott Klein, StatusPage.io

Part 2 – How StatusPage Went from Zero to a Million Dollars in 18 Months

Scott Klein is the co-founder of StatusPage, a Y-Combinator backed startup that lets you create a hosted status page for your app or website. You can use the status page to display downtime notifications, performance metrics, or any other information that your customers might need to know. StatusPage launched in 2013 and has raised about $250,000 to date. Its customers include companies such as KISSmetrics, Vimeo, and Kickstarter.

Part 1 – How StatusPage Went from Zero to a Million Dollars in 18 Months - Scott Klein

Scott Klein, StatusPage.io

Part 1 – How StatusPage Went from Zero to a Million Dollars in 18 Months

Scott Klein is the co-founder of StatusPage, a Y-Combinator-backed startup that lets you create a hosted status page for your app or website. You can use the status page to display downtime notifications, performance metrics, or any other information that your customers might need to know. StatusPage launched in 2013 and has raised about $250,000 to date. Its customers include companies such as KISSmetrics, Vimeo, and Kickstarter.

Part 2 – How a Neglected Side Project Turned Into a Multi-Million Dollar Startup - Amir Salihefendic

Amir Salihefendic, Doist.io

Part 2 – How a Neglected Side Project Turned Into a Multi-Million Dollar Startup

Amir Salihefendic is the founder and CEO of Doist.io, the makers of Todoist, an online and mobile task management app. He started Todoist in 2007 when he was still a student with two programming jobs on the side. He needed a way to manage his own work and productivity but couldn’t find the right tool. So he decided to build his own tool. He didn’t see it as a startup and he didn’t have any big ambitions. It was just a tool. Today, the company has over 4 million users and Todoist is also used by a number of Fortune 100 companies. And the tool that our guest built for himself has grown into a company with over 40 employees and several million dollars in annual revenue.

How a Developer Created  & Sold a $15,000 Training Course with no Sales Pitch - Douglas Calhoun

Douglas Calhoun, Hack Reactor

How a Developer Created & Sold a $15,000 Training Course with no Sales Pitch

Douglas Calhoun is the co-founder of Hack Reactor, a San Francisco-based startup whose vision is to create a CS degree for the 21st century. Hack Reactor runs 12-week intensive coding boot camps (which you can do in-person or online) designed to accelerate your software career. According to Hack Reactor, 99% of its graduates receive at least 1 full-time job offer within 3 months graduating and earn an average salary in the six figures.

The Automatic Customer: Creating a Subscription Business in Any Industry - John Warrillow

John Warrillow, The Value Builder System

The Automatic Customer: Creating a Subscription Business 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: Creating a Business That Can Thrive Without You, 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 was released by Random House in February 2015. John has been recognized by B2B Marketing as one of the top 10 business-to-business marketers in the United States.

How 2 Guys Learned to Code and Then Made $2M Teaching Others - Ankur Nagpal

Ankur Nagpal, Fedora

How 2 Guys Learned to Code and Then Made $2M Teaching Others

Ankur Nagpal is the co-founder and CEO of Fedora, a platform that enables anyone to easily create and sell online courses. The company was founded in 2013 and to date has raised $2M in funding. Prior to launching Fedora, Ankur launched a business while at college building social widgets between classes which generated over a $1M. Bloomberg Business called him a widget mogul.

How This Startup Went from Zero to $400K a Month in 2 Years - Tim Sae Koo

Tim Sae Koo, Tint

How This Startup Went from Zero to $400K a Month in 2 Years

Tim Sae Koo is the co-founder & CEO of Tint, a platform that enables brands to aggregate, curate and display social media feeds anywhere – including desktop, mobile, retail TV displays, event walls or jumbotrons at big events. Tint was founded in 2013 and was profitable within 3 months or launch. Today, their platform is used by over 45,000 brands around the world.

How a Failed Startup Helped Build a 7-Figure SaaS Business - Tim Sae Koo

Tim Sae Koo, Tint

How a Failed Startup Helped Build a 7-Figure SaaS Business

Tim Sae Koo is the co-founder & CEO of Tint, a platform that enables brands to aggregate, curate and display, social media feeds anywhere – including desktop, mobile, retail TV displays, event walls, or jumbotrons at big events. Tint was founded in 2013 and was profitable within 3 months or launch. Today, their platform is used by over 45,000 brands around the world.

How to Generate $30,000 a Month in Revenue from Content Marketing - Josh Pigford

Josh Pigford, Baremetrics

How to Generate $30,000 a Month in Revenue from Content Marketing

Josh Pigford is the founder of Baremetrics, a product that provides SaaS analytics for Stripe.

How to Take Your Business from $0 to $30,000 a Month in Recurring Revenue - Josh Pigford

Josh Pigford, Baremetrics

How to Take Your Business from $0 to $30,000 a Month in Recurring Revenue

Josh Pigford is the founder of Baremetrics, a product that provides SaaS analytics for Stripe.

How Rob Walling Grew Drip Revenue by Over 300% in 6 Months - Rob Walling

Rob Walling, Drip

How Rob Walling Grew Drip Revenue by Over 300% in 6 Months

Rob Walling is the founder of email marketing tool Drip and the owner of SEO keyword tool HitTail. He's also the author of the book "Start Small, Stay Small: A Developer's Guide to Launching a Startup". And his blog "Software by Rob" is a top 20 startup blog and is read by about 20,000 web entrepreneurs each month.

How a Gmail Plugin Built a Profitable 7-Figure SaaS Business - Aye Moah

Aye Moah, Baydin

How a Gmail Plugin Built a Profitable 7-Figure SaaS Business

Aye Moah is the co-founder and chief of product of Baydin, the maker of email productivity tools such as Boomerang for Gmail, a plugin which lets you schedule emails to send later, get email reminders and track the emails that you send. Baydin was founded in Jan 2010.

How to Build a 7-Figure Software Business from a WordPress Plugin - Stu McLaren

Stu McLaren, Wishlist Member

How to Build a 7-Figure Software Business from a WordPress Plugin

Stu McLaren is the founder of Wishlist Member, a powerful and easy-to-use plugin that can turn any WordPress site into a full-blown membership site. Wishlist Member powers over 54,000 online communities and membership sites worldwide. Stu is also the founder of Rhino Support, a helpdesk SaaS application.

How an Online Marketer Built a 6-Figure Software Business - Spencer Haws

Spencer Haws, Long Tail Pro

How an Online Marketer Built a 6-Figure Software Business

Spencer Haws is the founder of Longtail Pro, a keyword research software. Long Tail Pro allows you to generate hundreds or thousands of “long tail” keywords in minutes. Spencer launched Long Tail Pro in 2011 and successfully grew it into a 6-figure software business.

How a Design Agency Turned Itself Into a 7-Figure SaaS Business - Jim Belosic

Jim Belosic, ShortStack

How a Design Agency Turned Itself Into a 7-Figure SaaS Business

Jim Belosic is the founder and CEO of ShortStack, a tool that helps you build content, sweepstakes, and data collection forms that you can use on Facebook, mobile, and the web to help you convert more of your online followers to leads and customers. Jim founded ShortStack in 2010 and has bootstrapped the company all the way.

How an Idea to Improve Live Chat Built a Multi-Million Dollar Company - Ben

Ben, Olark

How an Idea to Improve Live Chat Built a Multi-Million Dollar Company

Ben is the co-founder and CEO of Olark, a tool that brings a hassle-free live chat to your website. Olark is a Y Combinator startup that was founded in 2009. Today, Olark has over 5000 customers in 151 countries and has grown into a multi-million dollar business.

How to Build a $5 Million Software Business from a Spreadsheet File - Jesse

Jesse, You Need a Budget

How to Build a $5 Million Software Business from a Spreadsheet File

Jesse is the founder of “You Need a Budget”, a software product that helps you with your personal budgeting. Jesse is a former Certified Public Accountant (CPA) turned software entrepreneur. He founded YNAB in 2004 and has successfully grown it into a multi-million dollar business with tens of thousands of users from all over the world.

How a Non-Technical Founder Bootstrapped a 6-Figure SaaS Business - Brecht Palombo

Brecht Palombo, Distressed Pro

How a Non-Technical Founder Bootstrapped a 6-Figure SaaS Business

Brecht Palombo is the founder of Distressed Pro, the home of BankProspector, a SaaS application that provides access to real-time updates for real-estate financials from some 14,000 banks and credit unions. He founded this business in 2009 and today has built a 6-figure business which he runs from on the road while traveling full-time with his wife and kids.

How Paras Chopra Bootstrapped an $8 Million SaaS Business - Paras

Paras, Wingify

How Paras Chopra Bootstrapped an $8 Million SaaS Business

Paras is the founder & CEO of Wingify, which makes Visual Website Optimizer, a market-leading A/B split testing tool. Paras launched and bootstrapped Visual Website Optimizer as a one-man software company in 2010 and within 2 years had over 1000 paying customers.  Currently, Visual Website Optimizer currently has an annual run rate of around $8 million.

How Balsamiq Bootstrapped Its Way Into a $6M Business - Peldi Guilizzoni

Peldi Guilizzoni, Balsamiq

How Balsamiq Bootstrapped Its Way Into a $6M Business

Peldi Guilizzoni is the founder of Balsamiq Studios, which makes Balsamiq Mockups a tool for creating quick and intuitive user interface mockups. Peldi launched Balsamiq as a one-man software company in 2008 and within 18 months, Balsamiq reached $2 million in revenue. Balsamiq is on track this year to hit $6 million in revenue.

Creating a Multi-Million Dollar Business from a WordPress Theme - Brian Gardner

Brian Gardner, StudioPress

Creating a Multi-Million Dollar Business from a WordPress Theme

Brian Gardner is the founder of StudioPress, which makes WordPress themes based on their Genesis framework. Brian grew StudioPress from nothing into a multi-million dollar business. In 2010, Brian merged StudioPress and several other companies with Copyblogger to create Copyblogger Media. Brian is a founding partner of Copyblogger Media and also its Chief Product Officer.

How a 24-Year Old Built a Highly Successful 8-Figure Business - Nathan Latka

Nathan Latka, Heyo

How a 24-Year Old Built a Highly Successful 8-Figure Business

Nathan Latka is the founder and CEO of Heyo. Heyo helps businesses easily create Facebook contests, sweepstakes and mobile-optimized landing pages to help get more fans, leads and sales. Heyo achieved over 6-figures in revenue in its first year and is currently an 8-figure business. Nathan and his team are currently on a mission to get to 500,000 paying customers by 2017.

How to Launch 2 Successful SaaS Products & Build a $1M Blog - Neil Patel

Neil Patel, KISSmetrics

How to Launch 2 Successful SaaS Products & Build a $1M Blog

Neil Patel is a Seattle-based entrepreneur, angel investor and analytics expert. He is best known for his work in digital marketing and as the co-founder of the analytics companies KISSmetrics and CrazyEgg. And his current blog, QuickSprout generates over $1 million in annual revenue. Neil shares with me how they took a couple of simple ideas and turned them into highly successful SaaS products.