In this episode of the Startup Therapy Podcast, Ryan and Will talk about what happens when you hit all your big goals and realize there might not be any more mountains left to climb. They discuss the complex feelings and identity crises that can emerge when success is achieved, and reflect on how to find new meaning and satisfaction beyond traditional goal-setting. The conversation touches on personal anecdotes, the concept of enjoying the process, and how to appreciate the journey in a fulfilling way.Resources:Startup Therapy Podcast https://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:27 The Identity Crisis of Achieving Goals01:05 Personal Reflections on Goal Setting02:25 The Evolution of Goals Over Time04:14 The Reality of Achieving Big Goals07:04 The Trap of Sensationalizing Goals10:58 The Diminishing Returns of Goal Achievement19:06 The Two Paths of Goal Setting: Pleasure vs. Pain20:40 Understanding Pain and Relief21:42 The Myth of Success Equals Happiness22:32 Existential Goals and Realizations23:31 The Challenge of Finding Fulfillment25:23 Enjoying the Journey vs. The Destination29:12 Reevaluating Ambitions and Goals33:11 Building for the Sake of Creation36:59 Infinite Games and Lifelong Pursuits

Will and Ryan talk about the fascinating and often overlooked journey of reinventing oneself. Will shares his diverse background, from being an ad guy to becoming a multi-time startup founder, and stresses the importance of embracing various roles to build a comprehensive skill set. The duo emphasizes that becoming a founder isn't a job you get hired for but one you create yourself. They explore how personal and professional reinvention can be the key to success in the startup world, encouraging founders to see themselves as a composite of their varied experiences. The episode is filled with personal anecdotes, practical advice, and an inspiring message: you are not confined to one identity or role — your potential is ever-evolving.Resources:Startup Therapy Podcast https://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:43 The Journey to Becoming a Founder01:28 Reinventing Yourself as a Founder02:31 The Value of Diverse Experiences03:55 A Humorous Job List08:11 The Role of Exposure in Career Choices13:06 Breaking Free from Career Constraints19:46 Early Career Hustles20:22 Learning from Experience20:53 First Sales Job21:30 Unexpected Opportunities23:22 Reinvention Starts Small24:06 Curiosity and Career Growth26:14 Building Skills Over Time28:04 The Power of Starting Small30:10 Embracing Continuous Learning32:21 The Value of Diverse Experiences39:59 Reinventing Yourself as a Founder

Ryan and Will talk about the growing isolation that founders are feeling despite having more ways to connect. They delve into how the shift to remote work, the impact of social media, and the rise of AI have contributed to stripping away the humanity from our daily interactions. They share personal experiences and offer insights into why this sense of loneliness has worsened, and most importantly, explore actionable steps founders can take to reconnect, feel less isolated, and build meaningful relationships in an increasingly digital world.Resources:Startup Therapy Podcast https://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:01:05 The Paradox of Connection and Loneliness02:36 Impact of Remote Work on Founders16:17 The Role of Social Media in Isolation20:49 The Distorted Reality of Social Media21:24 The Cynicism Towards Social Media Posts22:19 Creating Private Spaces and Personal Connections23:15 Declaring Relationship Bankruptcy26:53 The Impact of AI on Authenticity31:08 The Future of Human Interaction in a Digital World35:33 Combating Isolation as Founders

Ryan and Will discuss the journey of becoming a confident founder. Celebrating their 300th episode, they reflect on how learning to lead and building confidence starts with curiosity. They emphasize asking questions, even seemingly silly ones, to gain knowledge and confidence. Will and Ryan also dive into the importance of challenging oneself incrementally and being willing to make mistakes as key steps in growing confidence. They share personal anecdotes and practical advice, making a case for bravery, perseverance, and learning from failures. Perfect for any founder grappling with self-doubt or seeking actionable steps to boost their confidence.Resources:Startup Therapy Podcast https://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:58 Building Confidence Through Practice05:25 The Power of Curiosity09:25 Asking the Right Questions14:58 Taking on New Challenges19:03 Building Confidence Through Small Victories19:40 Teaching Kids Micro Challenges20:09 Challenging Yourself Incrementally21:17 The Line Between Ambition and Recklessness22:19 Learning Through Incremental Steps25:37 The Importance of Being Wrong27:41 Building Confidence as a Founder31:33 The Role of Bravery in Confidence

In this episode of The Startup Therapy Podcast, Ryan and Will discuss the true value of a college education for aspiring entrepreneurs. They explore whether the traditional path through higher education is the best route for those determined to start their own businesses. With personal anecdotes and economic insights, they argue that college may not always be the ideal path for founders, emphasizing the benefits of real-world experience and early entrepreneurial efforts. They also discuss societal expectations, financial implications, and alternative approaches to gaining the necessary knowledge and skills.Resources:Startup Therapy Podcast https://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:17 The Value of a College Degree for Founders00:55 Challenging the College Norm01:37 A Real-Life Example: Skipping College for Startups03:14 Generational Expectations and College07:25 The Economics of College Education08:04 The Financial Impact of College vs. Investing14:19 The Opportunity Cost of College for Founders20:21 The Power of Compounding Experiences20:35 Learning at Your Own Pace20:58 The Irrelevance of Traditional Education22:19 Founders Need a Broad Skillset22:57 The Limitations of College24:33 Alternative Learning Paths25:57 The Value of Practical Experience27:44 The Diminishing Value of a College Degree29:13 Questioning the College Path33:30 The Founder Mindset40:18 Restarting the Conversation on Education

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-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:51 The Myth of the Perfect Plan02:04 The Uber Example: Evolving Business Models03:55 The Importance of User Feedback04:48 Facing Investor Expectations07:44 Ego vs. Agility in Decision Making08:47 The Afford It Story: Lessons Learned13:21 Conclusion and Final Thoughts13:53 The Original Plan and Its Challenges14:25 Admitting Mistakes and Moving Forward15:10 Evolving as a Founder15:58 The Birth of Startups.com17:26 Learning from Market Feedback20:45 Detaching Ego from the Product23:14 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-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:32 The Pool Story: A Lesson in Work-Life Balance02:08 The Toxic Relationship with Work03:11 Startup Therapy: The Podcast's Origin08:15 Balancing Work and Family13:17 Non-Negotiables and Personal Values14:51 Conclusion and Final Thoughts15:35 Mitigating Guilt Through Productivity17:29 The Elusive Goal of Profit19:21 Emotional ROI in Startups21:57 Autonomy and Company Culture24:50 Balancing Safety and Happiness28:26 Avoiding the Trap of Obligations29:40 Creating a Non-Abusive Startup Relationship30:50 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-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:31 The Unexpected Reactions to Success02:54 Personal Stories of Resentment07:57 The Impact of Success on Relationships12:32 Social Media and Validation14:01 Processing Success and Insecurities19:34 Navigating Conversations About Success21:04 The Validation Loop Dilemma21:21 Caring About Others' Opinions21:57 The Spectrum of Self-Presentation23:17 The Insecurity Behind Social Media Influencers25:34 The Cost of Flaunting Success29:04 Extreme Humility and Its Consequences32:19 Balancing Humility and Pride37:01 The Art of Humble Bragging40:39 Avoiding Resentment Through Humility41:46 The Power and Responsibility of Success42:38 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-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:48 The Shift from Building to Managing01:29 The Struggles of Management02:13 The Evolution of Roles04:17 The Peter Principle in Action05:29 The Emotional Toll of Management08:34 Reflecting on the Past and Moving Forward09:57 The Realization and Acceptance12:39 The Dilemma of Founder Evolution13:10 Learning from the Past13:42 Commitment and Introspection15:02 The Cost of Doing What You Hate17:40 Recognizing and Embracing Change20:16 The Hard Decision to Move On25:03 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-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:29 The Psychological Cost of Milestones00:58 The 1% of Startups02:01 Celebrating Small Wins02:38 The Comparison Trap03:45 Balancing Credit and Complacency04:33 Contrasting Success Stories09:14 Perspective on Startup Success16:26 The Olympic Mindset and Startup Mentality17:39 The Power of Perspective and Gratitude19:35 Balancing Ambition and Gratitude21:16 Family Traditions and Simple Joys22:47 Reinforcing Self-Worth and Capability28:19 The Curse of the Exited Founder31:02 Changing Perspectives for Greater Happiness