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 Right
02:59 The Founder Reality: Uncertainty, Rapid Error Correction & the Boxing Analogy
03:44 Safety vs Startups: Why Most People Avoid the Risk
05:24 ‘Steering a Parked Car’: Indecision Kills Startups
07:54 Make the Call, Learn Fast: Small Failures, Big Truths
09:02 We’re Conditioned to Fear Failure (School, Work, Relationships)
11:59 Will’s Origin Story: Jason Barker and Learning to Beat the Monster
14:48 Choosing to Fail on Purpose: Turning Fear into a Superpower
17:06 Ryan’s First Big Failure: The Farm/Cattle Business Lesson Begins
17:45 Cash-Strapped Expansion: Inventory Leverage & a Brutal Winter
18:09 When the Side Hustle Needs a Side Hustle (and the Cost of Neglect)
18:35 Failing Hard at 12: Losing Animals and Learning to Plan
19:51 Founders Don’t Win by Being Right—They Win by Taking Hits
21:36 Shipping While Wrong: Marketing Experiments, MVPs, and Momentum
22:51 Hiring, Co-Founders & Investors: Why Nobody Can Pick Perfectly
24:00 The Real Skill: Recovering From Failure (Resilience as a Reflex)
30:26 Small Blast Radius, High Frequency: Reversible Bets & Kill Switches
31:13 Failure Is Portable: Building a House, Living ‘Why Not,’ No Regrets

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

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