Bilal Aijazi built one of the first Slack apps ever created. The install process was so clunky it required five manual steps of copying and pasting tokens. Yet 80% of people completed it anyway. That's when he knew Polly was solving something people desperately wanted.

Today, Polly serves millions of monthly active users across Slack, Teams, Zoom, Google Meet, Google Slides, and PowerPoint, generating multiple seven figures in ARR with just 20 people. But the journey from that first $8/month fantasy football customer to enterprise deals wasn't obvious—and platform risk nearly derailed everything when Slack launched competing features.

You'll learn:

Full show notes → saasclub.io/462

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James Ashford built GoProposal, a pricing and proposal platform for accountants, on a $5,000 WordPress multisite. Five years later, he sold it to Sage for eight figures with just 12 people on the team.

But the path to that exit wasn't about raising money or building fancy tech. It was about moving faster than well-funded competitors, staying closer to customers than anyone else, and building systems that made the business sellable from day one. James picked off the top customers of a competitor with $75 million in funding by publishing helpful content daily, running weekly webinars, and speaking to an accountant every single day just to learn.

You'll learn:

Full show notes → saasclub.io/461

This episode is brought to you by:

💖 ⁠Gearheart⁠ → Book a call + get the first 20 hours of development free

📡 ⁠⁠⁠Signal House⁠ → ⁠⁠⁠Learn more and get a demo

🚨 ⁠⁠⁠⁠NordStellar⁠⁠ → ⁠⁠⁠⁠Book a demo and get 20% off with code blackfriday20

Get weekly SaaS lessons and new founder stories → saasclub.io/email

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. Today, Assembled is an 8-figure ARR company with about 120 people, serves several hundred customers, and has raised $71 million.

But getting there was brutal. Ryan and his co-founders spent two years building before launching in March 2020—the same day the WHO declared COVID a global pandemic. About 25% of demos didn't show up. It took them 8 months to earn their first dollar of revenue. When they finally got customers on usage-based pricing with no minimums, usage flatlined during the pandemic. They thought it was their fault before realizing it was macro-related. So they stopped chasing growth and focused on the customers getting value, meeting them in person and building what actually mattered.

You'll learn:

Full show notes → saasclub.io/460

This episode is brought to you by:

🔐 ⁠⁠⁠Sprinto⁠⁠⁠ → ⁠⁠⁠Learn more and book a demo today⁠

💖 ⁠Gearheart⁠ → ⁠Book a call + get the first 20 hours of development free

📡 ⁠⁠⁠Signal House⁠ → ⁠⁠⁠Learn more and get a demo

🚨 ⁠⁠⁠⁠NordStellar⁠⁠ → ⁠⁠⁠⁠Book a demo and get 20% off with code blackfriday20

Get weekly SaaS lessons and new founder stories → saasclub.io/email

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:

💖 ⁠⁠Sprinto⁠⁠ → ⁠⁠Learn more and book a demo today

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🚀 SaaS Club Launch → Build your SaaS to $10K MRR

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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

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:

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

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:

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