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/

What to listen for:

Is AI truly the game-changer for startups, or does it bring unexpected chaos? This episode dives into how AI is transforming forecasting, marketing, product development, employment, and investment in the startup ecosystem. Ryan Rutan and Will Schroter discuss the rapid pace of change brought by AI, including the exciting opportunities and the unsettling uncertainties. They explore how traditional pillars of business like hiring, marketing, and customer acquisition are being upended, creating both new challenges and avenues for innovative founders to thrive. Tune in to understand how to navigate this AI-driven landscape and leverage the chaos for maximum impact.

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/

What to listen for:
00:00 Introduction and Future Predictions
00:49 The Impact of AI on Business Models
02:06 AI's Rapid Advancement and Market Disruption
04:17 Challenges in Marketing and Content Creation
10:04 Hiring and Talent Management in the AI Era
15:18 Product Development and Market Relevance
17:04 Industries Vanishing Overnight
17:32 The Accelerating Pace of Change
18:20 Investment in the Age of AI
19:07 The Future of Startup Funding
22:31 The Shrinking Moat of AI
24:54 Compounding Anxiety in the Startup Ecosystem
33:37 Founders: Built for Chaos
35:53 Embracing the Problem Business

How has the relentless pursuit of efficiency, aided by tools like remote work, Zoom, Slack, and AI, affected our human connections? In this episode, we're exploring the cost of optimized workflows on our humanity. We delve into personal anecdotes and discuss the ramifications of isolation in the workplace and the loss of shared experiences. We also contemplate the importance of reintroducing human interactions to ensure a balanced, connected, and more fulfilled work environment.

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/

What to listen for:
00:31 The Loneliness of Optimized Efficiency
01:48 The Impact of Remote Work on Human Connection
04:14 The Rise of AI and the Decline of Human Interaction
12:41 The Evolution of Remote Work Culture
17:20 The Dystopian Reality of AI Conversations
20:22 The Importance of Laughter and Human Interaction
21:23 Leveraging GPT for Problem Solving
22:18 The Downside of Relying on AI
23:45 The Value of Human Interaction in the Workplace
25:09 The Impact of AI on Team Dynamics
27:04 Balancing Efficiency and Human Connection
29:05 The Future of Startups and Human Connection
30:33 The Need for Human-Centric Work Cultures
32:06 Conclusion: Embracing Humanity in the Age of AI