Three failed startups. Zero revenue. Tope Awotona tried building a dating site, selling projectors, and selling grills—all failures because he was chasing money instead of solving real problems. Then he wasted an entire day scheduling a single meeting and realized what was missing. In this episode, founders will learn how to recognize when you've found product-market fit. Tope spent six months trying to talk himself out of building Calendly. But he couldn't dismiss it. Unlike his previous failures, he was solving his own problem, had seven years of sales experience, and saw existing scheduling tools with paying customers proving demand existed. This time, he went all in—emptying his bank account and flying to Ukraine to hire engineers. At the time of this interview, Calendly was generating $30M ARR and serving 4 million users, largely bootstrapped. 🔑 Key Lessons 🎯 Product-market fit requires passion, not profit motives: Tope's first three startups failed because he was chasing money instead of solving problems he cared about. 💡 Validate by observing behavior, not conducting interviews: Tope didn't talk to a single customer. He validated by seeing existing scheduling tools with paying customers. 🛠️ Optimize for the recipient's experience: Calendly won by reducing friction for invitees rather than only serving account holders. 📉 Failed startups teach you what not to do: Selling projectors taught Tope he needed better margins and passion for the problem. 🚀 Freemium + virality = organic growth: Calendly launched free by accident and became freemium by design, reaching 4 million users through viral sharing. 💰 Go all-in when you find product-market fit: After three part-time failures, Tope emptied his bank account and committed full-time to Calendly. ⚡ Study your competition's customers: Tope spent six months using competitors' products and reading their user forums to understand what they did well and where they failed. Chapters Introduction What Calendly does and who uses it Growing up in Nigeria and moving to the US Three failed startups before Calendly Why the projector and grill businesses failed Taking a sabbatical from entrepreneurship How the idea for Calendly came about Spending months trying to talk himself out of it Validation without customer interviews Emptying his bank account to go all-in Hiring engineers in Ukraine Differentiating on invitee experience The importance of design and integrations How Calendly got its first 1,000 users The accidental freemium model When Calendly started charging (and the mistake) Reaching $30M ARR and 4 million users The emotional rollercoaster of scaling Hiring too fast vs hiring too slow Lightning round 💌 Get weekly 5-minute SaaS insights: https://saasclub.io/email SaaS Club Programs Join the SaaS Club founder community: https://saasclub.co/plus Build your $10K MRR SaaS: https://saasclub.io/launch Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind Get 1:1 async coaching from Omer: https://saasclub.io/accelerate Resources Full show notes: https://saasclub.io/213 Subscribe to the podcast: https://saasclub.io/subscribe