Startup Therapy

The Value of Distraction

What if the thing that looks like a distraction is actually the move that saves your startup? This episode breaks down why the “stay focused at all costs” advice can be risky when you’re still figuring out what actually works. The hosts challenge the myth of the linear startup path, arguing that side quests—small, intentional experiments with capped downside—create learning, reduce single points of failure, and help you earn the right to pivot with evidence instead of vibes. They share how Fundable’s early equity crowdfunding push revealed founders were unprepared to raise money, which led to a major side quest: doing diligence on about 100 companies, talking to 200+, and acquiring six venture-backed businesses—work that became the genesis of startups.com. Along the way, they highlight the value of the quest itself (market intel, understanding what not to do, faster learning) and even mention an extreme near-distraction: briefly considering buying Atari. The conversation also reframes common “side quests” like doing services work while building a product, arguing that bringing in revenue to stay alive isn’t a distraction—it’s the business. They clarify the difference between a side quest (exploration) and a pivot (committing to a new direction), and point to the podcast itself as an example of a side quest that became a major long-term asset after a rough start. What to listen for: 00:40 The AI Newsletter Moment That Sparked the Topic 01:47 What a “Side Quest” Means for Founders 03:45 The Myth of the Linear Startup Path 06:34 When Focus Becomes a Liability: Certainty, Ego & Roadmaps 10:04 Side Quests as the Ongoing Lab (and Why It Never Ends) 12:01 Case Study: Fundable 2012 and the Crowdfunding Gold Rush 15:48 The Pivot: Founders Needed Help, Not Just a Platform 18:07 Side Quests Done Right: Controlled Experiments (…and Almost Buying Atari) 18:42 The Wild Idea: Almost Buying Atari (Nostalgia vs. Distraction) 19:48 Why Side Quests Matter: Learning More Than the Outcome 20:42 Founder-Forward Deal Talks & Market Intel as a Force Multiplier 22:10 Side Quests as “Insurance”: Selling the Learning to Skeptics 23:48 The Classic Startup Side Quest: Services to Pay the Bills 27:14 Side Quest vs. Pivot: Exploration First, Commitment Later 27:52 The Podcast as a Side Quest That Became Core to the Business 30:26 Earning the Right to Pivot: Evidence, Courage, and Finding Truth 34:20 Closing: De-Risking Through Exploration + Startups.com Community Invite 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/

Master Failure

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. What to listen for: 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/

We Can't Predict the Future Anymore

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

We wanted efficiency. We got isolation.

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

Are startups the future of employment?

What will AI do to everything? In this episode, we explore how AI is set to create a surge in new startups, reshaping employment as we know it. As jobs get displaced, the concept of big employment shifts, giving rise to smaller, more agile companies using AI tools. Drawing parallels with past technological revolutions, we highlight the opportunities that lower costs and new market demands present for founders. We discuss the transformation in various sectors, from customer service to content creation, and emphasize how AI can democratize entrepreneurship globally. Finally, we delve into the exciting potential for startup growth and the role of AI as both a tool and a transformative force in the startup ecosystem. 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: 00:24 The Impact of AI on Employment 01:16 Historical Parallels: Internet and Industrial Revolution 02:32 The Shift from Big Employment to Entrepreneurship 03:16 The Decline of Traditional Jobs 05:25 Opportunities in the New Economy 11:48 The Rise of the Creator Economy 20:15 Macro Trends and Future Outlook 23:52 The Rise of Billion-Dollar Startups 24:24 Price Collapse and Premium Experiences 26:01 The Impact of AI on Startups 26:44 The Creator Economy and Niche Markets 29:06 The Evolution of eSports 31:09 The Dawn of Young CEOs 33:22 The Future of Entrepreneurship 39:43 Global Entrepreneurship and Accessibility 45:56 The Age of the Startup