Big tech is transforming every aspect of our world. But how, and at what cost? This season of Land of the Giants – The Disney Dilemma – focuses on Disney’s ability to weather the ups and downs of the business cycle and changing tastes and explores what has kept it successful for over 100 years. The entertainment giant has leveraged nostalgia and its intellectual property to build a beloved brand, but after an acquisition spree that included Marvel, Lucasfilm, and 20th Century Fox, can it sus ...
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Startup Therapy
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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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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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Startup Therapy
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-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: 00:29 The Psychological Cost of Milestones 00:58 The 1% of Startups 02:01 Celebrating Small Wins 02:38 The Comparison Trap 03:45 Balancing Credit and Complacency 04:33 Contrasting Success Stories 09:14 Perspective on Startup Success 16:26 The Olympic Mindset and Startup Mentality 17:39 The Power of Perspective and Gratitude 19:35 Balancing Ambition and Gratitude 21:16 Family Traditions and Simple Joys 22:47 Reinforcing Self-Worth and Capability 28:19 The Curse of the Exited Founder 31:02 Changing Perspectives for Greater Happiness…
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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…
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Startup Therapy
1 You probably should be TERRIFIED. At least a bit.. 31:19
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Play Later Play Later Lists Like LikedRyan 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…
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Startup Therapy
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…
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Startup Therapy
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…
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Startup Therapy
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…
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Startup Therapy
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…
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Startup Therapy
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…
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Startup Therapy
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…
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Startup Therapy
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…
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Startup Therapy
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…
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Startup Therapy
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…
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Startup Therapy
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…
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Startup Therapy
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…
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Startup Therapy
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…
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Startup Therapy
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…
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Startup Therapy
1 What Previously Funded Founders Do Differently 33:21
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Play Later Play Later Lists Like LikedIn 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…
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Startup Therapy
1 Are Startups Easier for Experienced Founders? 33:01
33:01 Play Later Play Later Lists Like Liked33:01
Play Later Play Later Lists Like LikedIn 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'…
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Startup Therapy
1 How We Secretly Lose Control of Our Startups 37:28
37:28 Play Later Play Later Lists Like Liked37:28
Play Later Play Later Lists Like LikedIn this episode of the Startup Therapy Podcast, Ryan and Will discuss the complex dynamics of maintaining control in a startup. They explore the misconception that not having investors means maintaining control and highlight the various ways founders inadvertently lose control—from customers, co-founders to their own staff. They delve into the idea that control is a currency spent for growth and emphasize the importance of understanding and strategically managing the areas founders are willing or unwilling to cede control over. They reveal how seemingly routine decisions can lead to significant shifts in control, urging startup founders to be proactive in understanding and negotiating these exchanges. 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…
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Startup Therapy
1 Should Kids Follow in our Founder Footsteps? 36:25
36:25 Play Later Play Later Lists Like Liked36:25
Play Later Play Later Lists Like LikedIn this episode of the Startup Therapy Podcast, Ryan and Will explore the complexities of encouraging their children to become entrepreneurs. With nearly 300 episodes discussing the founder's journey, they delve into whether they'd want their kids to follow the same path. They recount personal experiences, weigh the pros and cons, and discuss the importance of allowing their children to make their own decisions. The episode emphasizes providing the tools and support to foster independent choices rather than directing them towards entrepreneurship. 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 00:00 Introduction: The Founder’s Dilemma 00:55 A Proud Yet Conflicted Parent 02:27 The Value of Experience 05:03 Balancing Passion and Practicality 08:10 Nurture vs. Nature in Entrepreneurship 09:59 The Role of Education and Constraints 16:21 The Reality of Entrepreneurship 18:56 Reflecting on Founders' Struggles 19:39 Balancing Optimism and Realism in Entrepreneurship 19:59 The Timeless Nature of Startup Challenges 21:31 Empathy and the Reality of Startup Therapy 23:10 The Impact of Parental Influence on Career Choices 25:23 Encouraging Authenticity in Children's Career Paths 30:12 Empowering Kids to Make Their Own Decisions 35:07 Final Thoughts on Raising Future Founders…
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Startup Therapy
In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Will Schroter discuss the evolving landscape of entry-level hiring for startups. They dive into why U.S. college graduates have fallen to the fourth pick for entry-level positions, overtaken by AI, global talent, and experienced young professionals who leverage new tools and platforms to gain relevant skills. They explore the benefits of each hiring option, debunk common misconceptions about global talent, and outline how these changes empower startups to make smarter, more economical hiring decisions. The discussion offers valuable insights for startup founders navigating the challenges of building efficient teams under tight budgets. 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 00:00 Introduction: The Changing Landscape of Entry-Level Talent 01:26 The Rise of AI in Startups 03:48 Global Talent: A New Frontier 07:30 Young and Hungry: The New Entry-Level 10:19 Challenges and Opportunities for College Grads 15:57 Resource Allocation in Startups 24:06 Stop Guessing and Get the Answers 24:16 The Global Talent Pool Advantage 25:15 Quality Concerns and Misconceptions 27:21 Parallel Validation in Startups 32:51 The Rise of Young and Hungry Talent 35:51 Evolving Job Market Expectations 39:50 The Changing Landscape of Hiring 45:20 Conclusion: Embrace the New Opportunities…
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Startup Therapy
In this episode of the Startup Therapy Podcast, Ryan and Will discuss the challenges of managing early-stage startup teams, particularly the high likelihood of turnover and the risks of handing out equity prematurely. They talk about the emotional toll of losing key team members and offer practical advice on creating vesting schedules and setting realistic expectations to safeguard against these common pitfalls. The conversation also touches on the dynamics of initial hires, the importance of flexibility, and the need to balance passion with practical considerations in team building. 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 00:00 Introduction to Startup Challenges 00:09 The Reality of Early Startup Teams 01:25 Startup Weekend Insights 02:38 The First Love Analogy 03:44 The Commitment Dilemma 04:24 Life Happens: Unplanned Disruptions 12:02 The Fragility of Equity-Based Compensation 13:45 Long-Term Team Dynamics 15:32 Understanding the Nature of Turnover 17:44 The Emotional Impact of Employee Departure 18:52 The Reality of Passion and Commitment 27:20 Equity Distribution and Vesting Schedules 31:50 Preparing for Inevitable Change…
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Startup Therapy
In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Will Schroter delve into the sacrifices that come with building startup companies. They explore the dangerous ambiguity of not having specific goals and timelines, using personal anecdotes to illustrate the costly trade-offs. Will reflects on his milestone birthday and the realization that 'later' never seems to arrive, sparking a discussion about the true worth of deferred happiness and success. The conversation underscores the importance of quantifying goals and ensuring that sacrifices made today lead to genuinely rewarding outcomes. They emphasize that the journey must be carefully balanced with immediate gratification to avoid a future riddled with regret. Through vivid storytelling, they highlight the crucial lessons for founders on how to navigate the complex landscape of ambition, sacrifice, and personal fulfillment. 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 00:21 The Danger of Vague Goals 00:57 Personal Reflections on Sacrifice 02:16 Quantifying Sacrifices and Rewards 04:03 The Reality of Sacrifice 05:27 Anecdotes of Sacrifice 15:08 The Moment of Truth 18:04 The Grand Experiment in Beverly Hills 18:36 The Struggles of Finding a Home in LA 19:07 Realizing the Cost of Living in Bel Air 20:34 Questioning the Move: A Moment of Clarity 23:10 The Decision to Return to Columbus 23:21 Reflecting on Sacrifices and Rewards 25:42 The Founder's Paradox: Happiness vs. Sacrifice 28:31 The Reality of Achieving Success 35:27 Balancing Sacrifice and Returns…
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Startup Therapy
In this episode of the Startup Therapy Podcast, Ryan Rutan and Startups.com founder Will Schroter discuss the unrealistic expectations that many startup founders have when it comes to selling their business. They detail the common pitfalls and misconceptions about startup valuation, the differences between raising capital and selling, the realities of private equity, and the dangers of deferred compensation. With insights from their own experiences of buying and selling companies, Ryan and Will provide a candid look at how to navigate the tricky world of startup acquisitions and set more realistic expectations for exit strategies. 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 00:00 Introduction to Startup Acquisitions 00:16 Realistic Expectations in Business Sales 01:09 Understanding the Acquisition Process 01:37 Our Acquisition Experience 02:29 Challenges in Closing Deals 04:31 The Importance of Direct Communication 07:08 The White Knight Fallacy 13:07 Investor Expectations vs. Reality 20:35 The Figma Acquisition: A Case Study 21:12 Understanding Market Leadership and Valuation 21:44 The Reality of Acquisition Multiples 24:53 The Spectrum of Potential Buyers 26:07 Private Equity: The Predatory Buyer 28:32 The Harsh Truths of Selling a Startup 32:53 Cash vs. Deferred Compensation 39:15 Managing Expectations in Startup Exits…
In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter discuss the often overlooked costs of ambition in the startup world. They explore how ambition, while necessary for building innovative companies, can become a debilitating force, leading to severe health issues, strained relationships, and emotional burnout. Using personal anecdotes and analogies, they emphasize the importance of recognizing the tipping point where ambition becomes more detrimental than beneficial, and advocate for a balanced approach to sustain long-term personal and professional health. 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 00:00 Introduction to Ambition in the Startup World 00:30 The Double-Edged Sword of Ambition 01:27 The Escalating Costs of Ambition 02:18 Ambition's Impact on Founders' Lives 05:22 Personal Stories of Ambition and Sacrifice 12:52 The Cultural Reward of Sacrifice 16:16 Understanding Technical Debt and Burnout 16:58 The Hidden Costs of Ambition 17:06 Financial Struggles and Early Warning Signs 18:20 Impact on Relationships 20:40 Mental Well-being and Isolation 23:55 The Ultimate Price: Physical Health 27:12 A Rational Perspective on Work-Life Balance 28:46 Final Thoughts and Advice…
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Startup Therapy
In this episode we discuss the current state of the startup ecosystem, which they describe as a 'silent recession.' Despite economic indicators suggesting otherwise, many startup founders are struggling with reduced capital flow and stagnating customer acquisition. The episode delves into the effects of the economic downturn on startups, the impact of investor behavior, and the historical context leading up to the current situation. Ryan and Will emphasize the importance of resetting expectations, adopting a survival mindset, and making tough decisions to ensure longevity in this challenging environment. While this period is difficult, there is always light at the end of the tunnel for those who can weather the storm. 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 00:08 The Silent Recession in Startup Land 00:38 The Reality of Founders' Struggles 02:25 Economic Indicators vs. Founders' Experiences 04:39 The COVID-19 Economic Magic Trick 06:03 The Shift in Startup Funding Dynamics 11:15 The Onset of Economic Challenges 12:20 The Impact on Startup Operations 16:14 VCs Halt Investments 16:50 Impact on Startups 17:35 IPO Implosions 18:20 VCs' Strategic Pause 19:56 The Domino Effect 22:56 Navigating the Downturn 27:39 Survival Strategies 31:37 Looking Ahead 33:07 Join the Startups.com Community…
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Startup Therapy
In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroeder navigate the complexities founders face regarding success and societal scrutiny. They delve into the common critiques founders encounter about their profits and perceived entitlement while emphasizing that success should be celebrated not vilified. The conversation provides a detailed look at the multiple layers of taxation startups endure and the misconceptions surrounding founder wealth. They also highlight the emotional toll and risk involved in building a startup, offering insights into the importance of supporting founders and normalizing 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: 00:00 Introduction to the Startup Therapy Podcast 00:46 The Stigma of Founders' Success 04:47 The Burden of Taxes on Founders 13:55 The Lack of Support During Failure 16:06 Reflecting on College Days and Financial Struggles 16:25 The Reality of Startup Life 17:25 Deserving Success and the Guilt Complex 18:50 Comparing Founders to Other Professions 21:36 The Value of Innovation and Hard Work 25:36 Addressing Income Inequality and Fairness 28:42 Encouraging Charitable Giving and Community Support 30:12 Join the Startups.com Community…
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