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:

Full show notes → saasclub.io/459

This episode is brought to you by:

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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:

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

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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:

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:

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:

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

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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:

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:

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

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