Startup Mistakes That Linger: Jason Sherman on Co-Founders, Smart Money, and MVP Learning

In this episode of My Favorite Mistake, Mark Graban talks with Jason Sherman, an entrepreneur, startup advisor, and educator, about the early startup mistakes that quietly shape everything that follows.

Episode page with transcript, video, and more

Jason shares hard-earned lessons about choosing co-founders, distinguishing “smart money” from money alone, and why MVPs should accelerate learning rather than encourage overbuilding. The conversation explores judgment, incentives, and alignment through a Lean lens — showing how optimism, unchecked assumptions, and unclear decision rights can undermine even strong ideas.

This episode is especially relevant for founders, leaders, and anyone working under uncertainty who wants to turn mistakes into insight instead of regret.