What if failure isn’t something to avoid, but a skill to master? This episode breaks down why startups can’t be built on certainty—new markets, new products, and new teams mean you’re guaranteed to be wrong a lot. The goal isn’t to “be right,” it’s rapid error correction: make decisions, ship anyway, learn fast, and recover even faster. The conversation covers how avoiding failure leads to paralysis (“steering a parked car”), why indecision compounds in startups, and how to reduce risk by keeping failures small, reversible, and frequent (kill switches, stop rules, and capped losses). They share early personal stories—school fights and a childhood cattle business collapse—to show how overcoming real consequences builds confidence and resilience. Practical examples include choosing an ICP quickly, improving poor conversion rates through iteration, using vesting/cliffs when picking co-founders, and why even top VCs still miss constantly. The key takeaway: the most dangerous competitor is the one who isn’t afraid to get hit, recover, and keep coming back—because that’s as close to “invincible” as a founder can get. 02:01 Failure Isn’t the Enemy: Stop Optimizing for Being Right02:59 The Founder Reality: Uncertainty, Rapid Error Correction & the Boxing Analogy03:44 Safety vs Startups: Why Most People Avoid the Risk05:24 ‘Steering a Parked Car’: Indecision Kills Startups07:54 Make the Call, Learn Fast: Small Failures, Big Truths09:02 We’re Conditioned to Fear Failure (School, Work, Relationships)11:59 Will’s Origin Story: Jason Barker and Learning to Beat the Monster14:48 Choosing to Fail on Purpose: Turning Fear into a Superpower17:06 Ryan’s First Big Failure: The Farm/Cattle Business Lesson Begins17:45 Cash-Strapped Expansion: Inventory Leverage & a Brutal Winter18:09 When the Side Hustle Needs a Side Hustle (and the Cost of Neglect)18:35 Failing Hard at 12: Losing Animals and Learning to Plan19:51 Founders Don’t Win by Being Right—They Win by Taking Hits21:36 Shipping While Wrong: Marketing Experiments, MVPs, and Momentum22:51 Hiring, Co-Founders & Investors: Why Nobody Can Pick Perfectly24:00 The Real Skill: Recovering From Failure (Resilience as a Reflex)30:26 Small Blast Radius, High Frequency: Reversible Bets & Kill Switches31:13 Failure Is Portable: Building a House, Living ‘Why Not,’ No Regrets Resources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/ Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/ What to listen for:
