Startup Therapy

Ryan and Will talk about the growing role of AI in startups. They explore how AI is automating traditional founder tasks like writing, coding, and analyzing data. The conversation delves into the existential threat AI poses to the founder's role and how founders can adapt to this new landscape. They argue that founders should embrace AI to focus on creativity, curation, and leadership rather than being bogged down by routi...

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 concep...

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 profession...

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 ...

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 confiden...

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-wo...

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...

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 host...

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 ...

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 fulfillmen...

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 pers...

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 activitie...

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 achi...

In this episode, Ryan and Will discuss the common misconception that startups need funding before generating revenue. They emphasize that the actual business isn't just the product but the revenue it generates. The discussion covers various strategies to bootstrap and generate cash flow, including building a minimal viable product, offering related services, and even taking on side gigs or unconventional methods to bring i...

Will and Ryan discuss the dangerous mindset founders can fall into after hitting it big with their startups. They reflect on the story of Peter Chesky, co-founder of Wish, who became a billionaire during the tech IPO boom of early 2021 but saw his net worth plummet as the company's stock tanked. The episode emphasizes the importance of treating any major payout as if it's the last one you'll ever receive. With only a small...

Ryan and Will discuss the evolution of startup location strategies. They reminisce about the bygone era when relocating to major hubs like San Francisco was essential for success due to access to talent, investors, and networking opportunities. Now, with advancements in remote work, AI, and digital connectivity, these factors have become less relevant. Ryan and Will delve into the changing dynamics of raising capital, buil...

In this episode of the Startup Therapy Podcast, the guys tackle the big question: was the entrepreneurial journey worth it? They discuss the sacrifices, the missed experiences, and the immense pressures that come with being a founder. Will shares a touching story about his daughter's unprompted appreciation for his hard work, leading to a reflection on whether the grinding was worth the outcome. Both hosts also highlight t...

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter discuss how childhood experiences influence the entrepreneurial journey. They explore why many founders' origin stories trace back to their early years and how formative events can plant the seeds of entrepreneurship. Will shares his personal story of selling candy as a child, highlighting moments that taught him vital business skills. The convers...

In this episode of Startup Therapy, Ryan Rutan and Will Schroeter challenge the startup world's focus on big exits and venture capital. They highlight the benefits of cash-flowing businesses, showing how consistent profits can lead to financial security. Using real examples, they explain how making $10K a month can be as powerful as having millions in the bank—emphasizing sustainable growth and long-term success.

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