Startup Therapy

The realities of evolving a startup. Ryan and Will discuss how the first idea is rarely the final solution, sharing insights on how to navigate the pivoting process. Using Uber and their own experiences at startups.com as examples, they explore the dangers of clinging to an initial plan and the importance of staying open to change. They also touch on overcoming ego, internalizing market feedback, and avoiding self-sabotage to ultimately achieve a more successful and fulfilling business. 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 Myth of the Perfect Plan 02:04 The Uber Example: Evolving Business Models 03:55 The Importance of User Feedback 04:48 Facing Investor Expectations 07:44 Ego vs. Agility in Decision Making 08:47 The Afford It Story: Lessons Learned 13:21 Conclusion and Final Thoughts 13:53 The Original Plan and Its Challenges 14:25 Admitting Mistakes and Moving Forward 15:10 Evolving as a Founder 15:58 The Birth of Startups.com 17:26 Learning from Market Feedback 20:45 Detaching Ego from the Product 23:14 The Importance of Adaptation

Ryan and Will delve into the complexities of maintaining a healthy relationship with your startup. They discuss their personal experiences and challenges in balancing the demands of a startup with personal well-being. Will shares an incredulous story about a friend enjoying a Tuesday afternoon in the pool, leading to a broader discussion on the importance of setting boundaries and recognizing the signs of burnout. The hosts emphasize the need for self-awareness, prioritizing personal values, and finding joy in the journey, not just the destination. They also touch on the benefits of giving team members autonomy and creating a supportive, non-toxic work culture. 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: 00:32 The Pool Story: A Lesson in Work-Life Balance 02:08 The Toxic Relationship with Work 03:11 Startup Therapy: The Podcast's Origin 08:15 Balancing Work and Family 13:17 Non-Negotiables and Personal Values 14:51 Conclusion and Final Thoughts 15:35 Mitigating Guilt Through Productivity 17:29 The Elusive Goal of Profit 19:21 Emotional ROI in Startups 21:57 Autonomy and Company Culture 24:50 Balancing Safety and Happiness 28:26 Avoiding the Trap of Obligations 29:40 Creating a Non-Abusive Startup Relationship 30:50 Join the Startups.com Community

Ryan and Will discuss the surprising reactions founders often face when they achieve success. They explore how unexpected resentment from friends and peers can arise, why it happens, and how to navigate these tricky social waters. Through personal anecdotes and practical advice, they delve into balancing humility and openness about success while staying true to oneself. Tune in to learn about managing relationships as you climb the ladder and handling the inevitable pushback with grace. 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 Unexpected Reactions to Success 02:54 Personal Stories of Resentment 07:57 The Impact of Success on Relationships 12:32 Social Media and Validation 14:01 Processing Success and Insecurities 19:34 Navigating Conversations About Success 21:04 The Validation Loop Dilemma 21:21 Caring About Others' Opinions 21:57 The Spectrum of Self-Presentation 23:17 The Insecurity Behind Social Media Influencers 25:34 The Cost of Flaunting Success 29:04 Extreme Humility and Its Consequences 32:19 Balancing Humility and Pride 37:01 The Art of Humble Bragging 40:39 Avoiding Resentment Through Humility 41:46 The Power and Responsibility of Success 42:38 Join the Startups.com Community

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