456: Mailtrap: From 20,000 Email Disaster to 7-Figure SaaS - with Sergiy Korolov
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
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455: Accelevents: How 5 Years of Nights & Weekends Built a $10M ARR SaaS - with Jonathan Kazarian
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
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454: Fyxer: From Executive Assistant Agency to $18M ARR AI SaaS - with Richard Hollingsworth
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
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453: StackAI: From MIT PhD to 7-Figure Enterprise AI Platform - with Bernard Aceituno
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
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452: Proof: SaaS Growth Lessons from $0 to $100M ARR - with Pat Kinsel
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
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