Startup Therapy

Ever feel like you’re working nonstop and still falling behind? The discussion argues founder happiness and decision-making improve fastest by recalibrating expectations, because “happiness =...

What do you think really happens if you burn out and step away for a minute? The conversation breaks down how founders often imagine an apocalyptic chain reaction—customers leaving, the team ...

What if the thing that looks like a distraction is actually the move that saves your startup? This episode breaks down why the “stay focused at all costs” advice can be risky when you’re stil...

What if failure isn’t something to avoid, but a skill to master? This episode breaks down why startups can’t be built on certainty—new markets, new products, and new teams mean you’re guarant...

Is AI truly the game-changer for startups, or does it bring unexpected chaos? This episode dives into how AI is transforming forecasting, marketing, product development, employment, and inves...

How has the relentless pursuit of efficiency, aided by tools like remote work, Zoom, Slack, and AI, affected our human connections? In this episode, we're exploring the cost of optimized work...

What will AI do to everything? In this episode, we explore how AI is set to create a surge in new startups, reshaping employment as we know it. As jobs get displaced, the concept of big emplo...

Ever felt like vacations just aren't cutting it when it comes to startup burnout? In this episode, Ryan Rutan and Will Schroter dive deep into why burnout is inevitable for founders and how q...

Can founders turn delusion into success? In this episode, Ryan and Will discuss the essential role of optimism in startups. Drawing parallels between founders and firefighters, the duo explor...

Ever find yourself caught in the trap of confusing visibility with progress? In this episode, we'll delve into why seeking attention can often feel like momentum but doesn't necessarily trans...

Is getting bigger always better for startups? This episode dives into the hidden costs of scaling up and how growth can sometimes make a company worse, not better. Ryan and Will discuss the t...

Ever wonder if being your authentic self at work might sometimes do more harm than good? The delicate balance of authenticity and diplomacy in leadership. From discussing the rare contexts wh...

Are you convinced that you need to fix all your flaws as a founder? In this episode, we explore why that's not necessarily true. Ryan and Will dive deep into the idea that both startups and t...

Have you ever wondered if remote work is better than being in the office? Ryan and Will dive into their experiences and how their work culture has evolved over 20 years. They discuss the pros...

Ever dreamt of handing off your startup to a killer operator and sipping margaritas while the money keeps rolling in? It sounds perfect, but reality often has other plans. In this episode, we...

Ever wonder what happens when a founder gets 'promoted' out of the CEO role? Ryan and Will dive into the tricky terrain of founder transitions, exploring how it feels to be nudged into roles ...

Ever felt like burnout is inevitable in your startup journey? You're not alone. Burnout can feel like a silent co-founder, but it doesn't have to signal the end of your entrepreneurial story....

Ever feel like you need more hours in the day? Turns out, you don't. In this episode, we dive deep into time management for founders, starting with a viral Reddit post that stirred some contr...

The complexities of alignment among founders, employees, and even spouses. They debunk the notion that perfect alignment exists, emphasizing that often, perceived alignment is more fiction th...

The challenging question of whether the sacrifices made in pursuit of entrepreneurial success are ultimately worth the payoff. Will retells his personal story of almost buying an expensive ho...

The critical do's and don’ts after a big financial win as a startup founder. They emphasize the importance of not oversharing about your wealth, shifting from an offensive to a defensive mind...

Ryan and will talks about a critical issue many founders face: knowing when to say 'enough is enough.' They explore the constant pursuit of growth both personally and professionally and how i...

How entrepreneurship can transform lives and communities? Will shares his personal journey from a challenging childhood to becoming a successful entrepreneur. They explore whether entrepreneu...

In this episode of the Startup Therapy Podcast, Ryan and Will discuss the challenges and dynamics of blending friendship and professionalism in startups. They delve into the potential pitfall...

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...

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 dis...

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...

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...

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 em...

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 highe...

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 ...

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...

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 ...

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 dis...

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 practi...

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...

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 weakn...

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 re...

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 billio...

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 acces...

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 immens...

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 st...

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,...

In this episode of the Startup Therapy podcast, Ryan and Will chat about how startup success isn’t always a straight path. They use Mark Cuban’s story as a prime example, showing why sticking...

In this episode of The Startup Therapy, Ryan Rutan and Will Schroter explore the 'what if' scenarios that often preoccupy founders. Will shares personal milestones, showing how taking bigger ...

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter dive into an interesting perspective: taking risks in entrepreneurship is actually a luxury, not the norm. They br...

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroeter delve into the anxiety surrounding contentment in the startup ecosystem. They question the conventional wisdom th...

Ryan Rutan and Will Schroeter discuss the complexities and challenges faced by startup founders, particularly the frequent occurrence of founders being replaced by investors. The conversation...

In this episode Ryan and Will delve into the intense pressures faced by founders from investors, peers, and the startup community. They discuss how these external expectations often drive fou...

Ryan and Will discuss the omnipresent challenges that come with running a startup. They delve into the perpetual 'shit storm' that founders face and share practical advice on how to keep movi...