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
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43:01
When Our Startup Outgrows Us
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
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25:59
When Being in the 1% Feels like Failure
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
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34:27
We Need Outside Interests that Consume Us
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-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:00:44 The Struggle with Relaxation01:36 Failed Attempts at Relaxation03:32 Vacation Dilemmas05:52 The Need for Mental Engagement09:47 The Importance of Completion14:07 Finding New Problems to Solve22:10 Woodworking as a Solution24:13 The Obsession Begins: From Birdhouses to Building a House24:48 The Challenge of Building a House from Scratch25:35 Balancing Work and Passion Projects26:31 The Importance of Completion and Physical Activity27:53 Managing Overwhelm and Finding Solutions29:14 The Power of Small, Consistent Efforts30:22 The Role of Meaningful Side Projects33:17 The Need for Mental and Physical Challenges36:21 The Value of Overwhelming Projects
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50:24
You probably should be TERRIFIED. At least a bit..
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 Newsletterhttps://www.startups.com/newsletterResources: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:00:35 Founders' Relationship with Fear01:35 Fear as a Motivator and Asset02:38 Personal Experiences with Fear and Risk03:17 Balancing Risk and Reward in Decision Making06:36 The Role of Fear in Entrepreneurship07:05 Cultural Differences in Risk Perception12:57 Embracing Fear as Part of the Job14:55 Building Resilience Through Failure15:39 Embracing Fear in Business16:02 The Role of Fear in Motivation17:46 The Danger of Complacency19:25 Taking Big Risks for Big Rewards21:23 Balancing Fear and Progress25:44 Facing Public Speaking Fears30:08 The Importance of Leaning Into Fear
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.
South Africa