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
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40:59
Founder Isolation is Getting Worse
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
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Forging Founder Confidence
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
The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.
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