Startup Therapy

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-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: 00:27 The Identity Crisis of Achieving Goals 01:05 Personal Reflections on Goal Setting 02:25 The Evolution of Goals Over Time 04:14 The Reality of Achieving Big Goals 07:04 The Trap of Sensationalizing Goals 10:58 The Diminishing Returns of Goal Achievement 19:06 The Two Paths of Goal Setting: Pleasure vs. Pain 20:40 Understanding Pain and Relief 21:42 The Myth of Success Equals Happiness 22:32 Existential Goals and Realizations 23:31 The Challenge of Finding Fulfillment 25:23 Enjoying the Journey vs. The Destination 29:12 Reevaluating Ambitions and Goals 33:11 Building for the Sake of Creation 36:59 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-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: 00:43 The Journey to Becoming a Founder 01:28 Reinventing Yourself as a Founder 02:31 The Value of Diverse Experiences 03:55 A Humorous Job List 08:11 The Role of Exposure in Career Choices 13:06 Breaking Free from Career Constraints 19:46 Early Career Hustles 20:22 Learning from Experience 20:53 First Sales Job 21:30 Unexpected Opportunities 23:22 Reinvention Starts Small 24:06 Curiosity and Career Growth 26:14 Building Skills Over Time 28:04 The Power of Starting Small 30:10 Embracing Continuous Learning 32:21 The Value of Diverse Experiences 39:59 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-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: 01:05 The Paradox of Connection and Loneliness 02:36 Impact of Remote Work on Founders 16:17 The Role of Social Media in Isolation 20:49 The Distorted Reality of Social Media 21:24 The Cynicism Towards Social Media Posts 22:19 Creating Private Spaces and Personal Connections 23:15 Declaring Relationship Bankruptcy 26:53 The Impact of AI on Authenticity 31:08 The Future of Human Interaction in a Digital World 35:33 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-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: 00:58 Building Confidence Through Practice 05:25 The Power of Curiosity 09:25 Asking the Right Questions 14:58 Taking on New Challenges 19:03 Building Confidence Through Small Victories 19:40 Teaching Kids Micro Challenges 20:09 Challenging Yourself Incrementally 21:17 The Line Between Ambition and Recklessness 22:19 Learning Through Incremental Steps 25:37 The Importance of Being Wrong 27:41 Building Confidence as a Founder 31:33 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-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: 00:17 The Value of a College Degree for Founders 00:55 Challenging the College Norm 01:37 A Real-Life Example: Skipping College for Startups 03:14 Generational Expectations and College 07:25 The Economics of College Education 08:04 The Financial Impact of College vs. Investing 14:19 The Opportunity Cost of College for Founders 20:21 The Power of Compounding Experiences 20:35 Learning at Your Own Pace 20:58 The Irrelevance of Traditional Education 22:19 Founders Need a Broad Skillset 22:57 The Limitations of College 24:33 Alternative Learning Paths 25:57 The Value of Practical Experience 27:44 The Diminishing Value of a College Degree 29:13 Questioning the College Path 33:30 The Founder Mindset 40:18 Restarting the Conversation on Education