Why Businesses Fail #04 - What Successful Founders Do Differently: Unpacking Lessons from Triangulate’s Journey

Jeremy introduces Triangulate and its ambitious goal: using digital footprints to create smarter, matched connections in online dating. The initial vision? License the algorithm to big-name dating sites.

Key Takeaways: 

• Always rigorously test your core business assumptions before launch.

• Founders need to validate product fit with real users, not just gut instincts.

• Early customer feedback can shape (or save) your entire business concept.

This segment drills into Triangulate’s biggest financial hurdles and how miscalculating revenue, user engagement, and marketing spend quickly eats into runway.

Key Takeaways: 

• Realistic revenue projections are essential—assume users won’t always pay as planned.

• Understand your “runway” as the number of pivots you can afford, not just months of survival.

• Know when to cut your losses: quitting is tough, but sometimes it’s the smartest move.

Jeremy shares raw reflections from Triangulate’s founder on what he’d do differently, from market selection to listening to customers—not advisors.

Key Takeaways: 

• Choose your first market carefully and talk to real users early—don’t just follow your passions.

• Avoid “echo chambers”; friends, VCs, and other founders aren’t your target customer base.

• Build the right team and don’t let ego push you into co-founder conflicts or unnecessary admin tasks.

The series wraps up with a practical guide to recognizing—and avoiding—classic startup “false starts,” outlining actionable steps to better research, prepare, and test before you build.

Key Takeaways: 

• Don’t skip detailed customer research; use tools like minimum viable product (MVP) landing pages to validate ideas.

• Every pivot eats into your cash and time. “Measure seven times, cut once.”

• Avoid convenience sampling; talk to a broad, representative range of users for real feedback.