Real journeys, unpacked for the lessons you can actually use.
Hosted by Matthew Sayles. An unvarnished look at building, breaking, and scaling founder-led businesses. Long-form conversations with leaders who share what actually happened behind closed doors — the mistakes, the pivots, and the operational lessons worth taking from them.
with Mike Hagen
You told your team exactly what you wanted. So why did it go wrong? Mike Hagen on the leadership rule that fixes it: clarity is kindness, ambiguity is abuse.
with David Raynerson
Most founders never find out what they’d do if they lost everything. David Raynerson found out at 59. What he rebuilt from the mud is the lesson.
Matthew Sayles launches Startup Stories, a podcast for founders who want to learn from real experience, the failures as much as the wins, not highlight reels.
Built something and learned something? The show is after the real version.
Apply to be a guest