Sam Darawish sold his first startup for $50M, then invested a few hundred thousand of his own money into Everflow. He didn't pay himself for two years. Most founders would never show screenshots at a trade show instead of a working product, but that's exactly what Sam did — and it landed his first customers. Today, Everflow generates nearly $30M ARR with 1,200 customers and a 120-person team across four continents. They've done it all without raising a single dollar of outside funding, proving that capital efficiency beats hypergrowth for building sustainable SaaS companies. You'll learn: Why showing screenshots at a trade show led to their first paying customers How narrowing to a tiny $70M TAM helped them reach $1M ARR faster What happened when they expanded to a bigger market that looked similar but wasn't Why spending only $400K to start forced them to focus on what really mattered How to maintain 25-30% growth while staying profitable from day one Full show notes → saasclub.io/459 This episode is brought to you by: 💖 ⁠⁠Sprinto⁠⁠ → ⁠⁠Learn more and book a demo today 📡 ⁠⁠Signal House → ⁠⁠Learn more and get a demo 🚀 SaaS Club Launch → Build your SaaS to $10K MRR Get weekly SaaS lessons and new founder stories → saasclub.io/email

David Shim sold his first startup for $200M, but when he started Read AI in 2021, he built something that failed spectacularly — 5% retention after 30 days. Instead of pivoting to chase revenue, he focused obsessively on fixing one metric: day-one ROI. Today, Read AI generates 8-figures in ARR, adds a million accounts monthly, and spends virtually nothing on marketing. David discovered that in the age of AI, the companies that win aren't the ones with the biggest models — they're the ones that solve real problems instantly. You'll learn: How David validated his idea by calling Zoom's founder directly and getting instant clarity Why focusing on day-one ROI instead of revenue led to 81% retention How to build viral loops that drive 1M+ monthly signups without marketing spend Why giving away your product for free can be your best growth strategy How to compete when Microsoft, Google, and Zoom enter your market Full show notes → saasclub.io/458 This episode is brought to you by: 💖 ⁠⁠Sprinto⁠⁠ → ⁠⁠Learn more and book a demo today 🚀 SaaS Club Launch → Build your SaaS to $10K MRR Get weekly SaaS lessons and new founder stories → saasclub.io/email

Kevin Wagstaff and his brother Michael turned a $5,000 investment into a $27 million ARR home inspection software business—without raising venture capital for the first six years. After nine months of customer research, they built Spectora by focusing on one philosophy: serve before selling. Kevin answered every support message within 60 seconds for five years, showed up daily in online communities without pitching, and even took a 6AM Sunday demo that unlocked their biggest growth wave. Today, Spectora serves 12,000+ inspectors while Kevin has stepped back from the CEO role, recognizing he was best suited for the zero-to-10 journey. You'll learn: How 9 months of field research revealed the workflow problem worth solving Why starting SEO content 12 months before launch created an unfair advantage The 6AM Sunday demo that opened doors to an exclusive mastermind group How building 200+ websites became an unexpected 10% revenue stream When to recognize you're a "zero-to-10 founder" and step aside gracefully Full show notes → saasclub.io/457 This episode is brought to you by: 💖 ⁠⁠Sprinto⁠⁠ → ⁠⁠Learn more and book a demo today 🚀 SaaS Club Launch → Build your SaaS to $10K MRR Get weekly SaaS lessons and new founder stories → saasclub.io/email

Back in 2011, Sergiy Korolov's team accidentally sent 20,000 test billing emails to real customers—a complete disaster. They built a simple internal tool to prevent it from happening again, shared it with the Ruby on Rails community, and it exploded. Fast forward to today: Mailtrap generates seven-figure ARR with 100,000+ monthly active users. The journey wasn't easy. For five years, Mailtrap was just a free side project. When Sergiy finally monetized in 2016, growth was slow and methodical—it took four more years to hit $1M ARR. Then came the biggest challenge: pivoting from a tool that blocks emails to one that sends them in production. It meant rebuilding infrastructure, fighting brand confusion, and competing with giants like SendGrid and Mailgun. You'll learn: How making signup surveys required provided deep customer insights without hurting conversions How a fake "Email Campaigns" button validated product demand before building anything Why community trust and developer-first thinking beat flashy marketing every time How they navigated the risky pivot from blocking emails to sending them reliably Why running 100+ customer interviews shaped their entire pricing and roadmap strategy Full show notes → saasclub.io/456 This episode is brought to you by: 💖 ⁠⁠Sprinto⁠⁠ → ⁠⁠Learn more and book a demo today 🚀 SaaS Club Launch → Build your SaaS to $10K MRR Get weekly SaaS lessons and new founder stories → saasclub.io/email

Jonathan Kazarian built Accelevents to $10 million ARR working nights and weekends for five years while keeping his hedge fund day job. But when COVID hit just as he went full-time, every event worldwide got canceled and revenue dropped to zero – forcing him to borrow $75,000 from his father's retirement to survive. Instead of waiting it out, Jonathan pivoted hard to virtual events and started pre-selling features they hadn't built yet. Within three months, they hit a million-dollar run rate and 10X'd revenue by year's end. But when the tech bubble burst in 2022, revenue got cut in half and he had to lay off more than half his 117-person team while rebuilding their reputation from scratch. You'll learn: Why maintaining 19-second response times 24/7 became Accelevents' secret weapon in the high-stakes events industry How hosting dinner events for event professionals generated better leads than cold outreach – without ever pitching the product What Jonathan learned from going through 21 Upwork contractors that changed how he thinks about hiring remote developers How pre-selling features they hadn't built yet helped them survive COVID and reach $1M ARR in three months Why after 10 years and multiple pivots, Jonathan still believes focusing on one business is the only way to win Full show notes → saasclub.io/455 This episode is brought to you by: 💖 ⁠⁠Gearheart⁠⁠ → ⁠⁠Book a free strategy session + get 20% off select services⁠ 🚀 SaaS Club Launch → Build your SaaS to $10K MRR Get weekly SaaS lessons and new founder stories → saasclub.io/email

Richard Hollingsworth bootstrapped an executive assistant agency to $5M ARR, then pivoted to AI and grew from $1M to $18M ARR in just 8 months. Today, Fyxer serves thousands of professionals with their AI email assistant, and Richard's team has grown from 4 to 40 employees while raising over $40M. Richard and his brother Archie started with data from their EA agency, waited for the right technology moment with GPT-3, then moved to San Francisco to scale. Their focus on professional services over tech companies, combined with a land-and-expand strategy, helped them close a $1.2M deal in 7 days and build a thriving AI SaaS business. You'll learn: How to turn an agency into an AI SaaS company using existing customer data and insights Why targeting professional services instead of tech companies unlocked massive growth opportunities How a land-and-expand sales motion helped convert single users into a 5,000-seat enterprise deal worth $1.2M What mistakes nearly destroyed their customer success during hypergrowth and how they recovered How to maintain culture and intensity while scaling from 4 to 40 employees in under a year Full show notes → saasclub.io/454 This episode is brought to you by: 💖 Gearheart → Book a free strategy session + get 20% off select services Get weekly SaaS lessons and new founder stories → saasclub.io/email

Bernard Aceituno went from PhD research at MIT to founding StackAI, a no-code AI platform that's now generating 7-figures in ARR with over 100 enterprise customers and $16M raised. In this episode, Bernard shares how he pivoted from academia to entrepreneurship, why his first product wasn't solving the right problem, and how a perfectly-timed MVP launch on Hacker News created overnight demand. He explains the painful lessons of chasing too many customer segments before finding focus with enterprise IT teams. You'll learn: What signals showed Bernard it was time to pivot from dataset management to workflow automation Why chasing too many ICPs nearly derailed the company and how they found focus How posting a scrappy MVP on Hacker News created 20 customer meetings in just two days Why attempts at reseller channels failed and what Bernard learned from waiting too long to hire sales How focusing on enterprise IT unlocked large contracts and steady expansion inside customer accounts Full show notes → saasclub.io/453 This episode is brought to you by: 💖 Gearheart → Book a free strategy session + get 20% off select services Get weekly SaaS lessons and new founder stories → saasclub.io/email

Pat Kinsel went from years of painful struggle at Notarize to building Proof, a SaaS platform approaching $100M ARR with 230 employees and $260M raised. In this episode, Pat explains how a notary error during his first startup exit sparked the idea, why he validated demand with a simple landing page before building, how he endured years of slow traction and false signals, and what changed when he expanded beyond notarization to transaction security. You’ll learn: - How Pat validated demand with a landing page and Google ads - Why losing money on every transaction nearly killed the company - What really happened when COVID demand spiked 100x overnight - How he spent years pushing to make online notarization widely accepted - Why many COVID-era enterprise signups never activated and what that taught about real product-market fit Full show notes → saasclub.io/452 This episode is brought to you by: 💖 Gearheart → Book a free strategy session + get 20% off select services 📫 Mailtrap → Get 20% off with code THESAASPODCAST Get weekly SaaS lessons and new founder stories → saasclub.io/email

Todd Olson went from two failed startups to building Pendo, a SaaS platform now generating $200M ARR with 880 employees and nearly $500M raised. In this episode, Todd reveals how early mistakes shaped his obsession with product-market fit, why he refused to hire salespeople until he validated the sales motion himself, and how creating an entirely new category forced him to abandon inbound marketing for manual outreach. You’ll learn: - Why Todd waited until $500K ARR before hiring salespeople - How raising prices 10x overnight changed Pendo’s trajectory - What two failed startups taught him about product-market fit - Why category creation required a bold go-to-market approach - The counterintuitive product strategy that made Pendo stand out Full show notes → saasclub.io/451 This episode is brought to you by: 💖 Gearheart → Book a free strategy session + get 20% off select services 📫 Mailtrap → Get 20% off with code THESAASPODCAST Get weekly SaaS lessons and new founder stories → saasclub.io/email

Flo Crivello is the founder and CEO of Lindy, a no-code platform for building AI agents to automate workflows. 👉 This episode is sponsored by Mailtrap. Try it at ⁠⁠Mailtrap.io⁠⁠ — use code THESAASPODCAST for 20% off Show Notes: ⁠https://saasclub.io/450 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: ⁠https://saasclub.io/email/⁠ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: ⁠https://saasclub.io/join/

Richard White is the founder and CEO of Fathom, the #1 rated AI note-taking app that automatically captures and summarizes meetings. 👉 This episode is sponsored by Mailtrap. Try it at ⁠Mailtrap.io⁠ — use code THESAASPODCAST for 20% off Show Notes: https://saasclub.io/449 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: https://saasclub.io/email/ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: https://saasclub.io/join/

Rob Woollen is the Co-Founder and CTO of Sigma Computing, a data analytics platform that lets business users analyze cloud-scale data without writing SQL. 👉 This episode is sponsored by Mailtrap. Try it at Mailtrap.io — use code THESAASPODCAST for 20% off Show Notes: Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs:

Jared Siegal is the founder and CEO of Aditude a monetization platform that helps digital publishers maximize their ad revenue. Show Notes: https://saasclub.io/447 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: https://saasclub.io/email/ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: https://saasclub.co/join

David Zitoun is the co-founder and CEO of Submagica tool that helps creators and small businesses turn their videos into viral-ready shorts in just a few clicks. Show Notes: https://saasclub.io/446 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: https://saasclub.io/email/ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: https://saasclub.co/join

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. Show Notes: https://saasclub.io/445 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: https://saasclub.io/email/ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: https://saasclub.co/join

Jonathan Festejo is the co-founder and CEO of Salesbricks, a platform that helps startups close deals faster and take the manual work out of quoting, billing, and getting paid. ==================================== ❤️ This episode is powered by Gearheart ⁠⁠⁠⁠https://saasclub.io/gearheart⁠⁠⁠⁠ Book a free 1:1 consultation: ⁠⁠⁠⁠https://saasclub.io/gearheart/book⁠⁠⁠⁠ ==================================== Show Notes: ⁠⁠⁠https://saasclub.io/444⁠⁠ Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: ⁠⁠⁠https://saasclub.io/email/⁠⁠⁠ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: ⁠⁠⁠https://saasclub.co/join⁠⁠⁠

Joseph Lee is the co-founder and CEO of Supademo, an AI-powered platform that helps you create interactive demos for onboarding, sales, and product education. ==================================== ❤️ This episode is powered by Gearheart ⁠⁠⁠https://saasclub.io/gearheart⁠⁠⁠ Book a free 1:1 consultation: ⁠⁠⁠https://saasclub.io/gearheart/book⁠⁠⁠ ==================================== Show Notes: ⁠⁠https://saasclub.io/443⁠ Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: ⁠⁠https://saasclub.io/email/⁠⁠ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: ⁠⁠https://saasclub.co/join⁠⁠

Sam Naficy is the CEO of Prodoscore, a SaaS platform that uses AI to show companies how work gets done by analyzing data from the cloud tools employees already use every day. ==================================== ❤️ This episode is powered by Gearheart ⁠⁠https://saasclub.io/gearheart⁠⁠ Book a free 1:1 consultation: ⁠⁠https://saasclub.io/gearheart/book⁠⁠ ==================================== Show Notes: ⁠https://saasclub.io/442 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: ⁠https://saasclub.io/email/⁠ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: ⁠https://saasclub.co/join⁠

Egidijus Pilypas is the co-founder of Exacaster, a SaaS company that helps subscription-based businesses grow revenue by turning customer data into actionable insights. ==================================== ❤️ This episode is powered by Gearheart ⁠https://saasclub.io/gearheart⁠ Book a free 1:1 consultation: ⁠https://saasclub.io/gearheart/book⁠ ==================================== Show Notes: ⁠https://saasclub.io/441 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: ⁠https://saasclub.io/email/⁠ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: ⁠https://saasclub.co/join⁠

Rami Tamir is the co-founder and CEO of Salto, a platform that helps teams manage and automate the configuration of SaaS apps like Salesforce, NetSuite, and Okta. ==================================== ❤️ This episode is powered by Gearheart https://saasclub.io/gearheart Book a free 1:1 consultation: https://saasclub.io/gearheart/book ==================================== Show Notes: https://saasclub.io/440 Join Email List: Get weekly SaaS learnings, new podcast episodes, and actionable insights right in your inbox: https://saasclub.io/email/ Join Community: SaaS Club is the community for early-stage SaaS founders and entrepreneurs: https://saasclub.co/join