EPISODE · Jan 5, 2026 · 46 MIN
Startup Mistakes That Linger: Jason Sherman on Co-Founders, Smart Money, and MVP Learning
from My Favorite Mistake: Learning Without Blame in Business and Leadership · host Mark Graban
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.
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What this episode covers
In this episode of My Favorite Mistake, Mark Graban talks with Jason Sherman, an entrepreneur, startup advisor, and educator, about the kinds of early startup mistakes that don’t feel like mistakes at the time — but shape everything that follows. Jason shares candid lessons about choosing co-founders, evaluating partners, and learning the hard way that not all funding is “smart money.” He reflects on how misaligned incentives, unclear decision rights, and unchecked optimism can quietly undermine trust and execution long before a product or market failure appears. The conversation also explores MVP thinking through a Lean lens, emphasizing learning over overbuilding. Jason explains why minimum viable product should mean faster feedback, not more features, and how mistakes become valuable data when leaders are willing to slow down, reflect, and learn.
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Startup Mistakes That Linger: Jason Sherman on Co-Founders, Smart Money, and MVP Learning
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