Startup Therapy

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 and cons of remote work, the importance of autonomy, and how remote setups have stripped away some of the overhead, revealing who truly thrives in this environment. They also explore whether it's possible to create a strong company culture remotely and how the shift has amplified the best and worst in employees. Tune in as they break down their journey from being die-hard office goers to embracing the flexibility and autonomy of remote work. 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: 00:36 The Shift from Office to Remote Work 01:01 Challenges of Remote Work 01:57 Socialization and Remote Work 04:42 Remote Work Rituals and Failures 07:26 Digital Culture and Transactional Work 12:06 Evolving Company Culture 19:14 The Evolution of Workplace Culture 19:34 Starting Fresh: Can We Be Transactional? 20:20 The New Culture: Autonomy and Responsibility 21:37 Balancing Work and Personal Life 23:49 The Value and Challenges of Remote Culture 25:34 Autonomy: The Ultimate Compensation 26:10 Remote Work: Amplifying Strengths and Weaknesses 32:13 The Social Aspect of Work 37:22 The Future of Work: Remote vs. In-Office

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 break down why passing on the reins isn't as smooth as it seems—from the slow degradation of everyday tasks to the irreplaceable instinct and urgency a founder brings. Discover why certain roles and tasks can be handed off successfully while others, like maintaining culture and strategic vision, often falter without the founder's unique touch. Tune in for practical advice on what you can actually hand off and what you should keep a close eye on to keep your startup thriving. 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: 00:06 The Dream of Handing Off a Startup 00:54 Early Days and Initial Success 02:14 The Startup Dream and Its Challenges 03:47 The Reality of Handing Off a Startup 05:09 The Slow Decline: Signs and Symptoms 07:48 Personal Experiences and Lessons Learned 17:00 The Boiled Frog Syndrome 19:45 The Timeless Nature of Startup Challenges 20:25 The Disconnect Between Perception and Reality 20:53 The Unique Metabolism of Founders 22:06 The Importance of Ownership and Passion 25:01 Handing Off Responsibilities: What Works and What Doesn't 27:43 The Irreplaceable Elements of Leadership 32:58 The Impact of Founder Presence on Company Culture 39:06 The Inherent Urgency of Founders

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 like Chief Vision Officer or Chairman—positions that often come when a new CEO is brought in. They discuss the emotions involved, the motivations of investors, and the strategies for turning this awkward moment into an opportunity. Whether you're in the thick of this situation or just want to be prepared, this episode provides valuable insights on maintaining dignity, negotiating effectively, and leveraging a graceful exit for future success. 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: 00:24 The Founder Promotion Dilemma 01:07 Personal Experience with Founder Titles 02:26 The Gary Coleman Effect 03:21 The CEO Replacement Backfire 05:29 The Emotional and Financial Impact of Founder Reassignment 10:44 Board Mechanics and Founder Control 13:06 Investor Strategies and Founder Leverage 18:34 Facing the Reality of Founder Reassignment 23:17 Famous Comebacks: Steve Jobs, Howard Schultz, and Jack Dorsey 24:36 The Emotional Toll of Being Replaced 25:10 Turning Emotions into Positive Actions 25:46 Negotiating Your Exit Strategy 30:54 Crafting Your New Role 31:55 The Importance of Maintaining Relationships 37:00 The Worst and Best Case Scenarios

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. In this episode, we discuss why burnout happens, how to diagnose it, and most importantly, how to treat it. Discover the importance of pacing yourself, the hidden costs of burnout, and why taking a break is crucial—not just for you, but for your entire team. We'll share personal anecdotes, practical tips, and the value of stepping away to recharge, so you can return stronger and more passionate than ever. Tune in to learn how to recognize the signs of burnout and create a treatment plan that works for you and your startup. 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 Personal Burnout Stories 04:46 The Hidden Costs of Burnout 08:41 Recognizing and Addressing Burnout 19:17 Recognizing Emotional Burnout 19:47 Impact of Economic Downturn on Founders 21:19 Personal Struggles and Their Impact on Work 22:13 Diagnosing and Addressing Burnout in Teams 23:04 The Importance of Personal Life in Preventing Burnout 27:32 Strategies for Treating Burnout 29:27 Finding Passion Outside of Work 32:59 Identifying and Mitigating Burnout Triggers 38:25 The Role of Leadership in Managing Burnout

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 controversy. We'll explore how compressing your timelines can lead to greater efficiency and free up your schedule for the things that truly matter. Forget the chronic meeting bloat and endless email chains; it's all about optimizing every minute. Discover how focusing on small, incremental tasks can lead to significant progress, both in your professional and personal life. Whether you're a solo founder or leading a team, this episode offers actionable insights to make the most out of your 24 hours. 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: 00:26 The Reddit Experiment: Stirring Controversy 03:53 The Time Compression Revelation 04:32 Analyzing Time Management 07:52 The Cost of Meetings and Conversations 15:21 The Impact of Family on Work Hours 17:44 The Power of Constraints 20:02 The Power of Saying No 20:24 Focus as a Job 20:34 Timeless Solutions 21:06 The Importance of Prioritization 21:34 Efficiency in Communication 22:34 Breaking Down Big Tasks 23:14 Consistency and Compounding 23:25 Building a House with Focus 26:53 Weekly Timelines for Productivity 36:12 Reclaiming Time for Personal Use

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 than reality. The conversation covers the inevitable differences in expectations, contributions, and risk tolerances that arise between co-founders and employees. The hosts also delve into the personal side, exploring how founders' professional decisions impact their relationships at home. Through candid anecdotes and practical insights, they highlight the importance of mutual respect and understanding in managing these fundamentally misaligned expectations in both business and personal life. 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: 00:42 The Myth of Alignment in Startups 01:06 Investor Alignment: Fact or Fiction? 01:48 The Role of Spouses in Startup Alignment 03:09 The Challenge of Aligning with Employees 04:59 Generational Differences in Work-Life Balance 14:50 The Reality of Co-Founder Alignment 21:16 The Challenge of Co-Founder Alignment 22:45 Spousal Support and Startup Life 25:45 Understanding and Managing Differences 28:31 The Myth of Perfect Alignment

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 house in Bel Air only to realize, thanks to his wife's intervention, that it wasn't what he truly wanted. The duo explores themes of sacrifice, payoff, and how aligning personal goals with true desires can lead to genuine happiness and fulfillment. Whether it's the freedom to travel or the joy of creating something with your hands, this episode urges founders to carefully contemplate their end goals and ensure their sacrifices lead to meaningful rewards. 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 Beverly Hills House Dilemma 03:05 Reflecting on Sacrifices and Payoffs 06:52 The Decision to Move Back to Ohio 13:42 The Value of Freedom and Purpose 17:46 The Danger of Undefined Goals 22:15 The Illusion of Goals 23:19 Realizing Unwanted Desires 24:13 Shifting Ambitions 26:21 The Fear of Losing Ambition 27:54 Evaluating Sacrifices 33:48 Finding True Fulfillment 36:31 Building a Dream 42:38 Advice for Founders

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 mindset, preserving your gains, and being cautious about new investments. They also explore how to handle the psychological and social challenges that come with newfound success, using real-life examples and practical advice to ensure you don't blow your hard-earned money. 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: 00:52 The Myth of the Big Exit 01:52 Emotional and Psychological Impact of Wealth 02:58 The Speech: Congrats, Now Don't Mess It Up 04:23 Financial Management for Newfound Wealth 06:11 The Three Js of Wealth: Judgment, Jealousy, and Jockeying 06:47 The Importance of Keeping Financial Information Private 20:06 The Shift from Offense to Defense in Wealth Management 22:24 The Founder Mentality Shift 23:53 The Casino Analogy 26:45 The Importance of Playing Defense 30:18 The Danger of Proving Yourself Again 36:33 The Save Point Strategy 44:19 The Burn Rate Dilemma 45:24 Conclusion: Preserving Your Wealth

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 it can turn into a liability if not checked. They dive into the psychological roots of why founders struggle with the concept of 'having enough,' the impact of a scarcity mindset, and the importance of recognizing diminishing returns. The hosts share personal anecdotes and offer practical advice on how to balance ambition with fulfillment, emphasizing the need for diversified 'buckets' of happiness beyond just business success. 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 Founder’s Dilemma: Knowing When Enough is Enough 01:26 The Scarcity Mindset and Its Impact 02:35 The Law of Diminishing Returns 03:12 Personal Anecdotes on Ambition and Satisfaction 05:38 The Concept of Utility in Economics 12:00 Balancing Growth and Happiness in Startups 16:56 Post-Exit: The Risk of Overreaching 20:11 The Downfall of a Legend 21:15 The Cost of Ambition 22:32 The Utility of Wealth 23:25 Chasing More: A Founder’s Dilemma 25:42 The Search for True Happiness 28:48 Redefining Success 33:50 Balancing Ambition and Value

How entrepreneurship can transform lives and communities? Will shares his personal journey from a challenging childhood to becoming a successful entrepreneur. They explore whether entrepreneurship can be a means to alleviate poverty, emphasizing the importance of hope, a safety net, and access to education and mentorship. The conversation dives deep into the potential impact of entrepreneurial initiatives on economic development and the need for structured support to foster entrepreneurial success on a global scale. 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: 00:40 The Power of Entrepreneurship to Alleviate Poverty 01:17 Personal Stories of Entrepreneurial Beginnings 02:34 The Ripple Effect of Entrepreneurship 03:38 Teaching Entrepreneurship as a Lifelong Skill 04:46 Hope as the Foundation of Entrepreneurship 05:37 Early Wins and Their Impact 07:17 The Importance of Small Wins 08:20 The Role of Hope and Pride in Entrepreneurship 12:15 The Willingness to Fail 22:49 The Risk of Failure for the Broke 23:45 Historical Context and Immigrant Success Stories 24:46 The Luxury of Credit and Capital 27:03 Entrepreneur Welfare and Venture Capital 29:14 The Case for Minimum Basic Income for Founders 29:40 The Parallel with Education and FAFSA 38:47 The Need for Structured Entrepreneurship Education 39:47 The Role of Hope and Security in Entrepreneurship 45:46 Entrepreneurship as a Solution to Poverty 47:34 Join the Startups.com Community

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 pitfalls of treating your startup team like a family, the consequences on both founders and employees, and the importance of setting clear boundaries. They highlight shared experiences from their early careers and emphasize the need for empathy, respect, and a professional approach to lead effectively without compromising authority. 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 Illusion of Startup as a Family 00:55 Early Career and Peer Dynamics 01:50 The Reality of Founder-Employee Relationships 03:46 The Pitfalls of Treating Employees as Family 05:54 Transparency in Startups: A Double-Edged Sword 07:13 Shared Risk and Misinterpreted Bonds 09:32 The Inevitable Strain on Relationships 12:17 The Limits of Friendship in Startups 16:18 The Evolution of Team Dynamics 18:12 A Throwback to Early Company Culture 18:31 The Impact of a New Hire 19:19 Cultural Misalignment and Realization 20:15 Adjusting Company Culture 21:43 Balancing Professionalism and Empathy 22:50 The Importance of Boundaries 24:18 The Dangers of Forced Inclusivity 28:24 Personal Experiences with Cultural Fit 32:20 The Family vs. Professional Sports Team Metaphor 36:42 Final Thoughts on Company Culture

Ryan and Will talk about the growing role of AI in startups. They explore how AI is automating traditional founder tasks like writing, coding, and analyzing data. The conversation delves into the existential threat AI poses to the founder's role and how founders can adapt to this new landscape. They argue that founders should embrace AI to focus on creativity, curation, and leadership rather than being bogged down by routine tasks. The episode underscores the importance of evolving with technology to enhance productivity and innovation, ultimately redefining the founder's job description for the future. 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: 00:34 Can AI Replace Founders? 01:16 The Evolution of AI Capabilities 02:03 AI's Impact on Copywriting and Creativity 03:28 AI in Advertising and Idea Generation 04:44 Embracing AI for Efficiency 06:31 AI as a Force Multiplier 09:44 The Future of AI and Founders 14:36 AI in Coding and Development 17:08 Leveraging AI for Business Growth 19:13 Simulating Business Scenarios with AI 19:38 The Role of AI in Business Decision Making 19:53 The Timeless Nature of Business Challenges 20:48 Embracing AI for Efficiency 21:12 The Unique Human Element in Business 23:40 The Future of Founders in an AI-Driven World 25:50 The Evolution of Founders' Roles 28:05 Leadership and Determination in Business 30:47 The Importance of Vision and Adaptability

In this episode of the Startup Therapy Podcast, Ryan and Will talk about what happens when you hit all your big goals and realize there might not be any more mountains left to climb. They discuss the complex feelings and identity crises that can emerge when success is achieved, and reflect on how to find new meaning and satisfaction beyond traditional goal-setting. The conversation touches on personal anecdotes, the concept of enjoying the process, and how to appreciate the journey in a fulfilling way. 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: 00:27 The Identity Crisis of Achieving Goals 01:05 Personal Reflections on Goal Setting 02:25 The Evolution of Goals Over Time 04:14 The Reality of Achieving Big Goals 07:04 The Trap of Sensationalizing Goals 10:58 The Diminishing Returns of Goal Achievement 19:06 The Two Paths of Goal Setting: Pleasure vs. Pain 20:40 Understanding Pain and Relief 21:42 The Myth of Success Equals Happiness 22:32 Existential Goals and Realizations 23:31 The Challenge of Finding Fulfillment 25:23 Enjoying the Journey vs. The Destination 29:12 Reevaluating Ambitions and Goals 33:11 Building for the Sake of Creation 36:59 Infinite Games and Lifelong Pursuits

Will and Ryan talk about the fascinating and often overlooked journey of reinventing oneself. Will shares his diverse background, from being an ad guy to becoming a multi-time startup founder, and stresses the importance of embracing various roles to build a comprehensive skill set. The duo emphasizes that becoming a founder isn't a job you get hired for but one you create yourself. They explore how personal and professional reinvention can be the key to success in the startup world, encouraging founders to see themselves as a composite of their varied experiences. The episode is filled with personal anecdotes, practical advice, and an inspiring message: you are not confined to one identity or role — your potential is ever-evolving. 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: 00:43 The Journey to Becoming a Founder 01:28 Reinventing Yourself as a Founder 02:31 The Value of Diverse Experiences 03:55 A Humorous Job List 08:11 The Role of Exposure in Career Choices 13:06 Breaking Free from Career Constraints 19:46 Early Career Hustles 20:22 Learning from Experience 20:53 First Sales Job 21:30 Unexpected Opportunities 23:22 Reinvention Starts Small 24:06 Curiosity and Career Growth 26:14 Building Skills Over Time 28:04 The Power of Starting Small 30:10 Embracing Continuous Learning 32:21 The Value of Diverse Experiences 39:59 Reinventing Yourself as a 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 rise of AI have contributed to stripping away the humanity from our daily interactions. They share personal experiences and offer insights into why this sense of loneliness has worsened, and most importantly, explore actionable steps founders can take to reconnect, feel less isolated, and build meaningful relationships in an increasingly digital world. 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: 01:05 The Paradox of Connection and Loneliness 02:36 Impact of Remote Work on Founders 16:17 The Role of Social Media in Isolation 20:49 The Distorted Reality of Social Media 21:24 The Cynicism Towards Social Media Posts 22:19 Creating Private Spaces and Personal Connections 23:15 Declaring Relationship Bankruptcy 26:53 The Impact of AI on Authenticity 31:08 The Future of Human Interaction in a Digital World 35:33 Combating Isolation as Founders

Ryan and Will discuss the journey of becoming a confident founder. Celebrating their 300th episode, they reflect on how learning to lead and building confidence starts with curiosity. They emphasize asking questions, even seemingly silly ones, to gain knowledge and confidence. Will and Ryan also dive into the importance of challenging oneself incrementally and being willing to make mistakes as key steps in growing confidence. They share personal anecdotes and practical advice, making a case for bravery, perseverance, and learning from failures. Perfect for any founder grappling with self-doubt or seeking actionable steps to boost their confidence. 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: 00:58 Building Confidence Through Practice 05:25 The Power of Curiosity 09:25 Asking the Right Questions 14:58 Taking on New Challenges 19:03 Building Confidence Through Small Victories 19:40 Teaching Kids Micro Challenges 20:09 Challenging Yourself Incrementally 21:17 The Line Between Ambition and Recklessness 22:19 Learning Through Incremental Steps 25:37 The Importance of Being Wrong 27:41 Building Confidence as a Founder 31:33 The Role of Bravery in Confidence

In this episode of The Startup Therapy Podcast, Ryan and Will discuss the true value of a college education for aspiring entrepreneurs. They explore whether the traditional path through higher education is the best route for those determined to start their own businesses. With personal anecdotes and economic insights, they argue that college may not always be the ideal path for founders, emphasizing the benefits of real-world experience and early entrepreneurial efforts. They also discuss societal expectations, financial implications, and alternative approaches to gaining the necessary knowledge and skills. 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: 00:17 The Value of a College Degree for Founders 00:55 Challenging the College Norm 01:37 A Real-Life Example: Skipping College for Startups 03:14 Generational Expectations and College 07:25 The Economics of College Education 08:04 The Financial Impact of College vs. Investing 14:19 The Opportunity Cost of College for Founders 20:21 The Power of Compounding Experiences 20:35 Learning at Your Own Pace 20:58 The Irrelevance of Traditional Education 22:19 Founders Need a Broad Skillset 22:57 The Limitations of College 24:33 Alternative Learning Paths 25:57 The Value of Practical Experience 27:44 The Diminishing Value of a College Degree 29:13 Questioning the College Path 33:30 The Founder Mindset 40:18 Restarting the Conversation on Education

The realities of evolving a startup. Ryan and Will discuss how the first idea is rarely the final solution, sharing insights on how to navigate the pivoting process. Using Uber and their own experiences at startups.com as examples, they explore the dangers of clinging to an initial plan and the importance of staying open to change. They also touch on overcoming ego, internalizing market feedback, and avoiding self-sabotage to ultimately achieve a more successful and fulfilling business. 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 Myth of the Perfect Plan 02:04 The Uber Example: Evolving Business Models 03:55 The Importance of User Feedback 04:48 Facing Investor Expectations 07:44 Ego vs. Agility in Decision Making 08:47 The Afford It Story: Lessons Learned 13:21 Conclusion and Final Thoughts 13:53 The Original Plan and Its Challenges 14:25 Admitting Mistakes and Moving Forward 15:10 Evolving as a Founder 15:58 The Birth of Startups.com 17:26 Learning from Market Feedback 20:45 Detaching Ego from the Product 23:14 The Importance of Adaptation

Ryan and Will delve into the complexities of maintaining a healthy relationship with your startup. They discuss their personal experiences and challenges in balancing the demands of a startup with personal well-being. Will shares an incredulous story about a friend enjoying a Tuesday afternoon in the pool, leading to a broader discussion on the importance of setting boundaries and recognizing the signs of burnout. The hosts emphasize the need for self-awareness, prioritizing personal values, and finding joy in the journey, not just the destination. They also touch on the benefits of giving team members autonomy and creating a supportive, non-toxic work culture. 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: 00:32 The Pool Story: A Lesson in Work-Life Balance 02:08 The Toxic Relationship with Work 03:11 Startup Therapy: The Podcast's Origin 08:15 Balancing Work and Family 13:17 Non-Negotiables and Personal Values 14:51 Conclusion and Final Thoughts 15:35 Mitigating Guilt Through Productivity 17:29 The Elusive Goal of Profit 19:21 Emotional ROI in Startups 21:57 Autonomy and Company Culture 24:50 Balancing Safety and Happiness 28:26 Avoiding the Trap of Obligations 29:40 Creating a Non-Abusive Startup Relationship 30:50 Join the Startups.com Community

Ryan and Will discuss the surprising reactions founders often face when they achieve success. They explore how unexpected resentment from friends and peers can arise, why it happens, and how to navigate these tricky social waters. Through personal anecdotes and practical advice, they delve into balancing humility and openness about success while staying true to oneself. Tune in to learn about managing relationships as you climb the ladder and handling the inevitable pushback with grace. Resources: Startup Therapy Podcast https://www.startups.com/community/startup-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: 00:31 The Unexpected Reactions to Success 02:54 Personal Stories of Resentment 07:57 The Impact of Success on Relationships 12:32 Social Media and Validation 14:01 Processing Success and Insecurities 19:34 Navigating Conversations About Success 21:04 The Validation Loop Dilemma 21:21 Caring About Others' Opinions 21:57 The Spectrum of Self-Presentation 23:17 The Insecurity Behind Social Media Influencers 25:34 The Cost of Flaunting Success 29:04 Extreme Humility and Its Consequences 32:19 Balancing Humility and Pride 37:01 The Art of Humble Bragging 40:39 Avoiding Resentment Through Humility 41:46 The Power and Responsibility of Success 42:38 Join the Startups.com Community