Startup Therapy

In this episode of the Startup Therapy Podcast,Ryan and Will delve into the emotional journey of startup founders who feel out of place in the very companies they built from scratch. They discuss the guilt and struggle founders experience when their roles change and they no longer enjoy their jobs. They share personal anecdotes and examine the impact of forced roles, from management misfits to a loss of personal fulfillment. The duo also explores the concept of evolving with or beyond your startup, and how to come to terms with these difficult but often necessary transitions. 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: 00:48 The Shift from Building to Managing 01:29 The Struggles of Management 02:13 The Evolution of Roles 04:17 The Peter Principle in Action 05:29 The Emotional Toll of Management 08:34 Reflecting on the Past and Moving Forward 09:57 The Realization and Acceptance 12:39 The Dilemma of Founder Evolution 13:10 Learning from the Past 13:42 Commitment and Introspection 15:02 The Cost of Doing What You Hate 17:40 Recognizing and Embracing Change 20:16 The Hard Decision to Move On 25:03 Celebrating Growth and Moving Forward

Ryan and Will discuss the psychological challenges founders face by constantly looking ahead and rarely celebrating their achievements. They explore how important it is for founders to practice gratitude and recognize their progress, even if their ultimate goals haven't been reached. The conversation delves into personal experiences, including Ryan's move to Guatemala and Will's time in Beverly Hills, highlighting how perspective and gratitude can significantly impact one’s satisfaction and motivation in their entrepreneurial journey. 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: 00:29 The Psychological Cost of Milestones 00:58 The 1% of Startups 02:01 Celebrating Small Wins 02:38 The Comparison Trap 03:45 Balancing Credit and Complacency 04:33 Contrasting Success Stories 09:14 Perspective on Startup Success 16:26 The Olympic Mindset and Startup Mentality 17:39 The Power of Perspective and Gratitude 19:35 Balancing Ambition and Gratitude 21:16 Family Traditions and Simple Joys 22:47 Reinforcing Self-Worth and Capability 28:19 The Curse of the Exited Founder 31:02 Changing Perspectives for Greater Happiness

Dive into the common struggle founders face with burnout and the inability to truly relax. Ryan and Will  share their personal experiences and discuss how traditional relaxation methods often fail for them. Instead, they highlight the importance of finding other meaningful and challenging obsessions outside of work to channel their energy. From woodworking and home-building to martial arts, they explore how these activities can provide a sense of accomplishment, progression, and actual mental rest, ultimately making them better and more effective in their startup journeys. Tune in to gain insights on how to recharge as a founder by embracing big, consuming projects that challenge and fulfill you. 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: 00:44 The Struggle with Relaxation 01:36 Failed Attempts at Relaxation 03:32 Vacation Dilemmas 05:52 The Need for Mental Engagement 09:47 The Importance of Completion 14:07 Finding New Problems to Solve 22:10 Woodworking as a Solution 24:13 The Obsession Begins: From Birdhouses to Building a House 24:48 The Challenge of Building a House from Scratch 25:35 Balancing Work and Passion Projects 26:31 The Importance of Completion and Physical Activity 27:53 Managing Overwhelm and Finding Solutions 29:14 The Power of Small, Consistent Efforts 30:22 The Role of Meaningful Side Projects 33:17 The Need for Mental and Physical Challenges 36:21 The Value of Overwhelming Projects

Ryan and Will discuss the prevalent fear in the market due to economic uncertainty in April 2025. They delve into how fear is a constant companion for founders and argue that it's not a weakness but a strength. Drawing on personal experiences, including public speaking and risky business moves, they illustrate how leaning into fear can drive massive growth and success. Comfortable activities rarely lead to significant achievements, they argue, emphasizing that true progress requires embracing discomfort. They also highlight the importance of conditioning oneself to fear and rejecting complacency to ensure continuous growth and impactful outcomes. Sign up for the Startups Newsletter https://www.startups.com/newsletter 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: 00:35 Founders' Relationship with Fear 01:35 Fear as a Motivator and Asset 02:38 Personal Experiences with Fear and Risk 03:17 Balancing Risk and Reward in Decision Making 06:36 The Role of Fear in Entrepreneurship 07:05 Cultural Differences in Risk Perception 12:57 Embracing Fear as Part of the Job 14:55 Building Resilience Through Failure 15:39 Embracing Fear in Business 16:02 The Role of Fear in Motivation 17:46 The Danger of Complacency 19:25 Taking Big Risks for Big Rewards 21:23 Balancing Fear and Progress 25:44 Facing Public Speaking Fears 30:08 The Importance of Leaning Into Fear

In this episode, Ryan and Will discuss the common misconception that startups need funding before generating revenue. They emphasize that the actual business isn't just the product but the revenue it generates. The discussion covers various strategies to bootstrap and generate cash flow, including building a minimal viable product, offering related services, and even taking on side gigs or unconventional methods to bring in money. By doing so, startups can extend their runway and better validate their business model before seeking significant investment. The episode includes examples from famous startups like Zappos and Airbnb to illustrate these points. Sign up for the Startups Newsletter https://www.startups.com/newsletter 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:| 00:51 The Broken Assumption About Funding 01:29 Generating Revenue Before the Product 02:39 Examples of Early Revenue Generation 03:07 The Zappos Story: Validating Demand 08:06 Personal Anecdotes on Testing Demand 10:27 The Importance of a Minimum Viable Product 18:39 Service-Based Proxies for Products 21:21 The Unexpected Success of Pitch Deck Services 22:04 Assumptions About Entrepreneurs and Investors 23:48 The Role of Services in Startup Success 25:33 The Importance of Revenue and Profitability 28:53 Creative Ways to Fund Your Startup 34:10 The Value of Bootstrapping and Hustle