Startup Therapy

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-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: 00:44 The Struggle with Relaxation 01:36 Failed Attempts at Relaxation 03:32 Vacation Dilemmas 05:52 The Need for Mental Engagement 09:47 The Importance of Completion 14:07 Finding New Problems to Solve 22:10 Woodworking as a Solution 24:13 The Obsession Begins: From Birdhouses to Building a House 24:48 The Challenge of Building a House from Scratch 25:35 Balancing Work and Passion Projects 26:31 The Importance of Completion and Physical Activity 27:53 Managing Overwhelm and Finding Solutions 29:14 The Power of Small, Consistent Efforts 30:22 The Role of Meaningful Side Projects 33:17 The Need for Mental and Physical Challenges 36:21 The Value of Overwhelming Projects

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 Newsletter https://www.startups.com/newsletter 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:| 00:35 Founders' Relationship with Fear 01:35 Fear as a Motivator and Asset 02:38 Personal Experiences with Fear and Risk 03:17 Balancing Risk and Reward in Decision Making 06:36 The Role of Fear in Entrepreneurship 07:05 Cultural Differences in Risk Perception 12:57 Embracing Fear as Part of the Job 14:55 Building Resilience Through Failure 15:39 Embracing Fear in Business 16:02 The Role of Fear in Motivation 17:46 The Danger of Complacency 19:25 Taking Big Risks for Big Rewards 21:23 Balancing Fear and Progress 25:44 Facing Public Speaking Fears 30:08 The Importance of Leaning Into Fear

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 in money. By doing so, startups can extend their runway and better validate their business model before seeking significant investment. The episode includes examples from famous startups like Zappos and Airbnb to illustrate these points. Sign up for the Startups Newsletter https://www.startups.com/newsletter 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:| 00:51 The Broken Assumption About Funding 01:29 Generating Revenue Before the Product 02:39 Examples of Early Revenue Generation 03:07 The Zappos Story: Validating Demand 08:06 Personal Anecdotes on Testing Demand 10:27 The Importance of a Minimum Viable Product 18:39 Service-Based Proxies for Products 21:21 The Unexpected Success of Pitch Deck Services 22:04 Assumptions About Entrepreneurs and Investors 23:48 The Role of Services in Startup Success 25:33 The Importance of Revenue and Profitability 28:53 Creative Ways to Fund Your Startup 34:10 The Value of Bootstrapping and Hustle

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 percentage of startups ever having significant exits, and even fewer doing it repeatedly, Ryan and Will stress why founders should be cautious with their newfound wealth instead of assuming it will keep flowing. Sign up for the Startups Newsletter https://www.startups.com/newsletter 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: 01:01 The Rise and Fall of Wish 03:01 Lessons from the Wish IPO 05:15 The Psychology of Founders 11:52 A Counter Story: Priceline's IPO 15:13 Reflecting on High School Memories 15:37 The Illusion of Endless Wealth 15:51 The Reality of Financial Downturns 19:09 Understanding Venture Capital Statistics 21:28 The Rarity of Repeat Success 24:18 Advice for Founders: Secure Your Wins 28:11 The Importance of Financial Safety 30:39 Final Thoughts: Keep the Win

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, building teams, and cultivating networks without needing to uproot one's life to a specific city. Sign up for the Startups Newsletter https://www.startups.com/newsletter 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: 00:39 The Shift in Startup Location Importance 01:46 Reevaluating the Need to Move for Startups 01:58 The Impact of Remote Work and COVID-19 03:51 Debating the Necessity of Moving to San Francisco 06:12 Talent Acquisition in the Remote Work Era 09:23 Financial Considerations and Cost of Living 15:10 The Role of Investors in the New Startup Landscape 17:54 Questioning the Need for Large Engineering Teams 18:21 Capital Requirements and Investor Expectations 19:14 The Evolution of Pre-Seed Rounds 22:27 The Impact of Technology on Investment 23:43 Relocating for Networking Opportunities 27:13 The Shift in Startup Location Necessities 32:03 The Value of Flexibility in Startup Locations 35:59 Conclusion: Startups Can Thrive Anywhere

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 the freedom, flexibility, and the unique sense of achievement they've gained. However, they caution about the inevitable costs and the importance of balancing life and startup aspirations. A must-listen for anyone questioning the value of their entrepreneurial path. Sign up for the Startups Newsletter https://www.startups.com/newsletter 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: 00:49 A Moment of Gratitude 02:42 Was It All Worth It? 06:02 Missed Experiences and College Life 11:00 The Weight of Responsibility 15:12 Habits and Hardships 19:32 Guilt and Work-Life Balance 24:20 The Timeless Nature of Startup Challenges 24:52 The Hidden Costs of Success 25:47 The Value of Sacrifice 26:39 The True Meaning of Freedom 28:04 The Journey to Personal Agency 29:20 The Impact of Entrepreneurship 31:15 The Irony of Wealth and Freedom 35:12 The Cost of Corporate Success 45:44 Balancing Life and Startup

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 conversation also delves into the importance of agency, the tools needed for entrepreneurial success, and the role of parents in nurturing a child's potential to create their own path. Sign up for the Startups Newsletter https://www.startups.com/newsletter 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: 00:13 Exploring Founder Origin Stories 01:51 Will's Childhood Story 10:14 The Power of Agency 10:53 Teaching Kids About Agency 20:54 Personal Reflections on Agency 21:22 The Power of Agency and Optimism 22:14 Parental Protection vs. Empowerment 22:40 Real-Life Stories of Overcoming Adversity 24:40 The Magic of Agency in Hardship 26:42 Tools for Founders and Kids 27:23 Early Lessons in Entrepreneurship 34:56 The Importance of Sales Skills 42:29 Teaching Kids the Value of Agency 43:22 Join the Startups.com Community

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. Sign up for the Startups Newsletter https://www.startups.com/newsletter 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: 00:19 The Value of Consistent Cash Flow 01:23 Examples of Profitable Local Businesses 03:37 The Misconception of Startup Exits 03:49 Real-Life Stories of Successful Small Businesses 06:16 The Broken Narrative of Startup Wealth 07:26 Reevaluating Business Success Metrics 09:05 The True Value of a Profitable Business 09:38 Calculating the Financial Impact 13:20 The Reality of Business Exits 18:09 Replacement Value vs. Exit Value 19:14 The Value of Experience and Pre-existing Solutions 19:39 Cash vs. Business Value: A Deep Dive 20:21 Real-life Examples of Business Growth 23:34 Risks and Rewards of Running a Business 27:12 The Importance of Consistent Earnings 34:54 Long-term Value and Compounding Effects

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 it out for the long run is so important—because success can happen at any time in a founder’s career. They also talk about how those early small wins can build up to something bigger and why setting strict timelines for success doesn’t really make sense. At the end of the day, one big right moment in a 50-year career can be a total game-changer. Sign up for the Startups Newsletter https://www.startups.com/newsletter 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: 00:07 The Reality of Founders' Success 02:00 Mark Cuban's Journey to Billionaire Status 06:35 The Importance of Small Wins 10:15 Financial Stability and Early Success 15:57 The Value of Consistent Small Wins 18:02 Success Doesn't Have a Timeline 18:12 When Does Success Happen? 18:20 Examples of Late Bloomers 18:45 The Myth of Early Success 19:59 The Impact of Timing 20:44 The Internet Era and Young Wealth 21:40 Outliers and Unrealistic Expectations 25:13 Consequences of Chasing Quick Success 27:28 The Value of Longevity in Business 30:02 Unexpected Success Stories 31:46 Staying in the Game 32:36 Join the Startups.com Community

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 risks shaped his journey. They discuss the hidden costs of success, the pitfalls of romanticizing alternative outcomes, and the importance of realistic risk assessment. The key takeaway? Embrace risk to avoid the regret of missed opportunities. Sign up for the Startups Newsletter https://www.startups.com/newsletter 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: 00:07 – Reflecting on milestones and 'what ifs' 00:44 – The risks and rewards of entrepreneurship 04:00 – A hilarious temp job experience 07:34 – The reality of alternate paths 09:02 – The danger of romanticizing 'what ifs' 13:48 – The cost of success 15:29 – Building a realistic mental model 16:18 – Stop guessing and get real answers 16:26 – The cost of staying in a job you hate 17:30 – Should you stay or leave? 18:10 – The true cost of success 19:12 – The hindsight trap: romanticizing outcomes 21:56 – Learning from failure and modeling risk 22:55 – Zirtual acquisition: a case study in risk 28:47 – Surviving failure and moving forward 31:35 – Avoiding regret and embracing risk

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 break down what it really costs to take risks, how to figure out your "minimum viable risk pool," and why having a financial cushion is key to surviving setbacks. They share personal stories from their experience at Startups.com, emphasizing the importance of cutting personal and business expenses to stretch your runway and make smarter decisions. This episode is all about helping entrepreneurs understand the financial milestones they need to hit to keep their businesses afloat—and how time plays a big role in navigating risks. This episode is packed with advice for anyone trying to manage the tricky balance of risk and reward in entrepreneurship. Tune in to learn how to take smarter risks and build a solid foundation for your business! Sign up for the Startups Newsletter https://www.startups.com/newsletter 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: 00:15 Why Taking Risks Is a Luxury 02:08 Balancing Personal and Business Costs 03:44 Lessons from Startups.com 05:55 Why You Need a Risk Buffer 10:25 Figuring Out the Minimum Viable Risk Pool 16:51 Financial Discipline and Budgeting 19:09 The Freedom Fund Explained 26:51 How to Survive Financial Challenges

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 that equates contentment with stagnation and probes whether startup founders should aim for contentment as a goal. Through personal anecdotes and industry examples, they explore the influence of perpetual ambition and societal expectations on entrepreneurs. They also discuss the differences between being content and being complacent and reflect on the continuous urge to chase new problems and challenges, even when previous goals have been achieved. Sign up for the Startups Newsletter https://www.startups.com/newsletter 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: 00:44 Questioning the Need for a Business Coach 02:05 The Dilemma of Contentment vs. Ambition 04:02 Reflecting on Milestones and Contentment 07:35 The Nature of the Startup World 15:23 Anxiety as a Driving Force 20:51 The Anxiety of High Achievers 22:11 The Pressure of Success: Avicii and Pharrell 23:59 Imposter Syndrome Among Overachievers 26:21 The Elusive Goal of Contentment 29:08 Balancing Ambition and Contentment 33:29 The Trap of Endless Ambition 40:44 Finding True Satisfaction

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 delves into the motivations behind such investor decisions, the difficulties in replicating a founder's passion and vision, and the common pitfalls and consequences of these transitions. The hosts share personal anecdotes and provide insights on how to prevent these situations, handle them professionally if they arise, and maintain valuable stakeholder relationships. This episode is a must-listen for any startup founder navigating the turbulent waters of investor relations and company growth. Sign up for the Startups Newsletter https://www.startups.com/newsletter 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: 00:25 The Downfall of Bench and Ian Crosby's Story 01:54 Investor Motivations and Founder Replacements 03:33 Understanding Investor Expectations 05:40 The Slow Burn of Founder Dismissal 08:23 The Impact of Replacing Founders 13:49 Personal Stories of Founder Replacement 16:47 The Challenges of Replacing Founders 19:26 Augmenting the Team vs. Replacing the Founder 22:01 Why Investors Push Founders Out 24:00 Navigating Earn-Out Periods in Acquisitions 24:26 The Challenge of Replacing Founders 26:43 Timing the Transition: Leadership vs. Management 29:08 The Mercenary CEO: Pros and Cons 35:31 Investor Expectations and Founder Realities 42:19 Handling Founder Exits Professionally

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 founders to pursue goals misaligned with their personal beliefs and values. The conversation explores how unchecked expectations can lead to burnout and misguided efforts. They share insights on the importance of auditing and resetting personal and business expectations to ensure they align with one's true goals and values. The hosts also highlight the dangers of comparing oneself to other founders or industry giants, and emphasize the significance of building a business that meets personal fulfillment rather than external benchmarks. Sign up for the Startups Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/st... Website https://www.startups.com/begin LinkedIn / startups-co Join our Network of Top Founders Wil Schroter / wilschroter Ryan Rutan / ryan-rutan What to listen for: 00:32 The Source of Pressure and Expectations 03:32 Investor Expectations and Their Impact 04:05 Personal Story: Missing Investor Expectations 05:44 The Reality of Investor Expectations 10:15 Comparing Yourself to Other Founders 17:45 The Peer Comparison Trap 18:06 Personal Journey: From Poverty to Success 20:01 The Futility of Social Media Comparisons 23:07 Tying Success to Self-Worth 28:20 The Illusion of Goals and Success 31:53 Reevaluating Startup Expectations 36:43 Conclusion: Building What Matters to You

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 moving forward even when everything feels like it's falling apart. Key points include regaining perspective, converting anxiety into actionable tasks, breaking down large goals into manageable micro-goals, and finding healthy obsessions to channel stress. They emphasize the importance of maintaining a positive outlook, not just for personal sanity but for the wellbeing of the entire team, and share personal anecdotes and strategies that have helped them through their toughest times. Sign up for the Startups Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/st... Website https://www.startups.com/begin LinkedIn / startups-co Join our Network of Top Founders Wil Schroter / wilschroter Ryan Rutan / ryan-rutan What to listen for: 00:07 The Perpetual Shit Storm of Startups 01:01 Practical Advice for Founders in Crisis 02:10 Regaining Perspective During Tough Times 05:08 Personal Stories of Overcoming Challenges 15:29 The Importance of Taking Action 20:41 Managing Anxiety with Side Tasks 21:58 The Power of Micro Goals 23:37 Breaking Down Big Tasks 26:29 The Importance of Focus 32:07 Finding Healthy Obsessions 41:08 Building Momentum with Small Wins 43:14 Join the Startups.com Community

In this episode of the Startup Therapy Podcast, Ryan and Will delve into the often misunderstood motivations of venture capitalists. They discuss why investors push startups to grow rapidly, the pressures VCs face to deliver returns within a specific timeframe, and the fundamental differences between the stakes for founders and investors. The episode uncovers the reasons behind the 'push you off a cliff' approach, the impact of the 2 and 20 model on VC behavior, and the importance of understanding these dynamics to better navigate the startup journey. Sign up for the Startups Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/st... Website https://www.startups.com/begin LinkedIn / startups-co Join our Network of Top Founders Wil Schroter / wilschroter Ryan Rutan / ryan-rutan What to listen for: 00:11 Understanding Investor Motivations 01:12 The VC Time Crunch 03:57 Profit vs. Growth: A VC Perspective 13:25 The Reality of VC Salaries 16:29 Founders vs. Investors: Different Stakes 19:00 Conclusion: Aligning Goals with Investors

In this episode of the Startup Therapy Podcast, Ryan and Will discuss the daunting realities of raising capital for startups. By sharing insights and experiences from both first-time and repeat founders, they delve into the recurring theme of regret found amongst entrepreneurs who've gone through the funding process. Topics include the hidden costs of raising money, the pitfalls of losing focus, and the challenges of working with investors. The hosts offer practical advice on when to raise funds, how to mitigate the risks of distraction, and the importance of being selective and strategic about bringing investors on board. Whether you're gearing up for your first round of fundraising or re-evaluating your approach, this episode provides valuable lessons to help navigate the complex landscape of startup financing. Sign up for the Startups Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/st... Website https://www.startups.com/begin LinkedIn / startups-co Join our Network of Top Founders Wil Schroter / wilschroter Ryan Rutan / ryan-rutan What to listen for: 00:14 The Reality of Raising Funds 00:38 Founders' Regrets and Reflections 02:15 The Perils of Not Getting Paid 04:22 Understanding Founder Compensation 11:04 Strategies for Better Compensation 13:24 Challenges with Profitable Companies 15:02 The Pressure to Grow or Bust 15:16 The Dilemma of Raising Too Early 15:47 The Vulnerability of Early Stages 16:22 The Importance of Timing in Fundraising 16:56 The Pitfalls of Early Funding 17:28 The Distraction of Fundraising 20:34 The Impact of Investor Expectations 28:23 The Challenge of Having a New Boss 31:50 Key Takeaways and Final Thoughts

In this episode of the Startup Therapy Podcast, Ryan and Will debunk the myth that each startup venture becomes progressively easier with experience. They explore the truths and fallacies surrounding repeat entrepreneurship, sharing personal anecdotes and insights from their extensive history of building and acquiring startups. Discussing expectation management, the double-edged sword of experience, and the harsh realities of repeating past mistakes, Ryan and Will emphasize that while experience offers certain advantages, it does not guarantee success in new ventures. They also highlight the emotional resilience required to endure the cyclical nature of startup challenges and the ever-present difficulties of achieving product-market fit and successful marketing, regardless of prior victories. Sign up for the Startups Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/st... Website https://www.startups.com/begin LinkedIn / startups-co Join our Network of Top Founders Wil Schroter / wilschroter Ryan Rutan / ryan-rutan What to listen for: 00:15 Debunking the Myth of Easier Startups 01:27 The Double-Edged Sword of Experience 02:32 Drawing from Multiple Experience Buckets 05:15 Expectation Management in Startups 09:39 Avoiding Duplicate Mistakes 13:01 Raising Capital: Lessons Learned 15:16 The Value of Experience in Decision Making 17:07 The Reality of Investor Promises 17:17 Understanding People: A Founder's Key Skill 18:38 Emotional Maturity in Leadership 20:00 Challenges That Never Get Easier 21:57 The Ever-Changing Landscape of Product Market Fit 25:39 Marketing Struggles for Experienced Founders 27:40 The Pain of Failure: It Never Gets Easier 31:30 The Value of Experience and the Role of Luck 32:38 Join the Startups.com Community

Ryan Rutan and Will Schroter explore the intricate and often misunderstood relationship between founders and their startups. They tackle the question of whether the founder works for the startup or vice versa, challenging common perceptions shaped by societal views and political discourse. The hosts discuss the unspoken 'contract' entrepreneurs form with themselves, the inevitable trade-offs of startup leadership, and the sacrifices founders make for their companies. They emphasize the emotional and financial tolls on founders, the discrepancies in founder-employee dynamics, and the need for startups to stay aligned with the founder's original mission. This episode stresses the importance of maintaining control and balancing personal goals with the demands of the startup ecosystem. Sign up for the Startups Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/st... Website https://www.startups.com/begin LinkedIn / startups-co Join our Network of Top Founders Wil Schroter / wilschroter Ryan Rutan / ryan-rutan What to listen for 00:35 The Founder vs. Startup Dilemma 00:51 Political and Economic Perspectives 01:40 The Reality of Founders' Lives 03:00 The Initial Contract of Founders 05:11 The Shift in Founders' Roles 06:15 The Permanent Struggle of Founders 07:43 Revisiting the Founders' Goals 10:34 The Reality Check 15:30 The Investor's Impact 15:44 The New Boss: Investors and Liabilities 16:49 The Pain of Payroll: Sacrificing Founder Salaries 19:10 Credit Cards and Cash Flow: Desperate Measures 21:20 The Founder’s Dilemma: Sacrifice and Equity 23:42 The Reality of Startup Success: Rare and Elusive 28:28 The Emotional Toll: Identity and Relationships 31:49 Conclusion: Building a Startup That Works for You

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter explore the vital importance of maintaining a startup's foundational 'why' – the core reason for its existence. They discuss the excitement and clarity that founders experience in the early stages, the operational challenges that can cause them to lose sight of their mission over time, and practical strategies for rekindling that original passion. Through personal anecdotes and examples of companies like Apple and Google, the hosts underscore how minor compromises can erode a company's core mission. They emphasize the need for founders to continuously revisit and reinforce their original motivations to ensure sustained passion and purpose. Listeners will gain insights on recognizing when they've deviated from their vision, the benefits of realigning with the 'why', and actionable steps to recenter their focus, all while maintaining clarity and engagement within their teams. Sign up for the Startups Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/st... Website https://www.startups.com/begin LinkedIn / startups-co Join our Network of Top Founders Wil Schroter / wilschroter Ryan Rutan / ryan-rutan What to listen for 00:29 The Importance of 'Why' in Startups 03:17 Losing Sight of the 'Why' 05:24 Diagnosing the Loss of 'Why' 09:21 The Impact of Compromises 15:56 Tiny Compromises Lead to Major Changes 18:48 The Slippery Slope of Compromises 19:50 Losing Sight of the 'Why' 20:50 Rediscovering the Purpose 22:12 The Importance of Remembering the 'Why' 24:30 Practical Steps to Reconnect with the 'Why' 30:55 Identifying and Correcting Misalignments 35:36 The Constant Battle to Maintain the 'Why'