Startup Therapy

Can founders turn delusion into success? In this episode, Ryan and Will discuss the essential role of optimism in startups. Drawing parallels between founders and firefighters, the duo explores how belief against all odds drives entrepreneurs forward. They explain how maintaining optimism is not just about having a positive outlook but about creating momentum from minor wins and leveraging chaos as an opportunity. The hosts also address the fine line between optimism and dishonesty, emphasizing the importance of an 'educated wish.' Whether you're battling to raise funds or struggling to maintain morale, this episode delves into why a founder’s unyielding belief is crucial for startup survival and growth.Resources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:07 The Delusional Optimism of Founders01:02 Creating and Living in a Fantasy02:00 Running Toward Chaos04:54 The Passion and Drive of Founders05:59 The Reality of Startup Life12:08 The Role of Belief and Proof14:31 Finding Optimism in Small Wins16:40 Persistence in the Face of Rejection18:56 The Power of Hope in Business19:52 The Role of Optimism in Startups21:41 Balancing Optimism and Honesty23:03 The Fine Line Between Optimism and Deception26:07 The Importance of Optimism in Leadership28:55 The Role of Optimism in Overcoming Challenges32:05 The Founder's Mindset: Manufacturing Optimism

Ever find yourself caught in the trap of confusing visibility with progress? In this episode, we'll delve into why seeking attention can often feel like momentum but doesn't necessarily translate to business traction. Will Schroter shares a cautionary tale from his own experience, revealing how his focus on brand-building and networking kept him from truly building his company. We explore the fine line between personal branding and productivity, and why many founders need to prioritize the latter to achieve real success. It's a reminder that until your product and business are fully developed, every external interaction could be costing you more than it's worth.00:30 The Trap of Visibility: A Personal Story02:24 The Illusion of Popularity vs. Productivity06:21 The Modern-Day Equivalent: Social Media09:24 Balancing Publicity and Productivity11:23 Cautionary Tales and Lessons Learned12:55 The Importance of Focus and Balance14:48 Earning the Right to Brand Build15:29 The Pitfalls of Prioritizing Popularity Over Business16:07 The Honeymoon Period of Venture Funding17:40 The Dangers of Personal Branding for Founders18:47 When Personal Views Hurt Business21:39 Balancing Personal and Company Brand23:48 Focus on Building the Business First30:22 The Cost of External InteractionsResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:

Is getting bigger always better for startups? This episode dives into the hidden costs of scaling up and how growth can sometimes make a company worse, not better. Ryan and Will discuss the trade-offs between size and quality, using examples like Google and PayPal. They explore how rapid growth can diminish company culture, slow down decision-making, and introduce inefficiencies. The conversation also covers personal experiences in startup growth, emphasizing the importance of optimizing for better rather than just bigger. Whether it's adding more staff or raising capital, they advocate for making decisions that enhance company quality and founder life satisfaction.Resources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:14 The Myth of Bigger is Better00:43 Examples of Companies That Grew and Suffered02:00 The Hidden Costs of Scaling05:08 Personal Experiences with Growth Challenges13:01 The Importance of Freedom and Quality17:18 The Hidden Costs of Growth17:58 Balancing Growth and Quality of Life20:39 Defining Non-Negotiables for Better Business22:33 Scaling with Soul: Maintaining Company Culture24:41 Quality Over Quantity: Making Strategic Decisions28:07 The Power of Saying No31:15 Sticking to Your Values for Sustainable Growth

Ever wonder if being your authentic self at work might sometimes do more harm than good? The delicate balance of authenticity and diplomacy in leadership. From discussing the rare contexts where pure honesty works, to sharing personal anecdotes about navigating the consequences of unfiltered truth, this episode unpacks how transparency can impact your team, brand, and personal relationships. Find out why being your true self might only be great advice 6% of the time and how effective communication can save you from unintended fallout.Resources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:01:01 The Consequences of Unfiltered Honesty01:26 Generational Differences in Professionalism02:44 The Power Dynamics of Founders04:45 Balancing Honesty and Diplomacy06:01 The Luxury of Honesty and Risk08:04 The Importance of Filtering Communication12:56 The Duality of Professional Personas15:21 The Consequences of Honesty in Leadership16:19 Balancing Honesty and Diplomacy17:10 The Importance of Empathy in Communication18:26 The Cost of Unfiltered Honesty19:51 Frameworks for Effective Communication20:55 Lessons from the Terminator: Choosing Responses Wisely22:07 The Role of Diplomacy in Leadership28:17 The Medium Matters: Hot, Warm, and Cold Communication29:56 Prioritizing Outcomes Over Authenticity

Are you convinced that you need to fix all your flaws as a founder? In this episode, we explore why that's not necessarily true. Ryan and Will dive deep into the idea that both startups and their founders are loaded with problems, some of which aren't really 'problems' at all but hidden superpowers. From obsessive tendencies to ADHD, they discuss how to harness these traits for success rather than trying to fix them. Drawing from personal experiences and industry insights, they touch on the influence of pharmaceutical marketing, the role of social media in shaping perceptions, and the importance of finding context for your strengths. This episode challenges you to rethink how you view your weaknesses and offers a fresh perspective on founder self-acceptance and leveraging inherent traits for entrepreneurial success.Resources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:33 Founders and Their Problems01:15 Pharmaceutical Industry Insights02:36 Social Media and Problem Creation03:46 Personal Struggles of Founders05:07 Overthinking and Control Issues11:15 ADHD and Academic Challenges17:11 Harnessing Obsessiveness for Success20:40 Evaluating Self-Help Advice21:09 Struggles with Attention Span21:31 Learning Outside Traditional Education22:15 Emphasizing Strengths Over Weaknesses23:29 Founders and Their Strengths28:08 Anxiety as a Superpower34:46 The Importance of Context in Learning38:36 Self-Acceptance and Utilizing Strengths

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 Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:36 The Shift from Office to Remote Work01:01 Challenges of Remote Work01:57 Socialization and Remote Work04:42 Remote Work Rituals and Failures07:26 Digital Culture and Transactional Work12:06 Evolving Company Culture19:14 The Evolution of Workplace Culture19:34 Starting Fresh: Can We Be Transactional?20:20 The New Culture: Autonomy and Responsibility21:37 Balancing Work and Personal Life23:49 The Value and Challenges of Remote Culture25:34 Autonomy: The Ultimate Compensation26:10 Remote Work: Amplifying Strengths and Weaknesses32:13 The Social Aspect of Work37:22 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 Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:06 The Dream of Handing Off a Startup00:54 Early Days and Initial Success02:14 The Startup Dream and Its Challenges03:47 The Reality of Handing Off a Startup05:09 The Slow Decline: Signs and Symptoms07:48 Personal Experiences and Lessons Learned17:00 The Boiled Frog Syndrome19:45 The Timeless Nature of Startup Challenges20:25 The Disconnect Between Perception and Reality20:53 The Unique Metabolism of Founders22:06 The Importance of Ownership and Passion25:01 Handing Off Responsibilities: What Works and What Doesn't27:43 The Irreplaceable Elements of Leadership32:58 The Impact of Founder Presence on Company Culture39:06 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 Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:24 The Founder Promotion Dilemma01:07 Personal Experience with Founder Titles02:26 The Gary Coleman Effect03:21 The CEO Replacement Backfire05:29 The Emotional and Financial Impact of Founder Reassignment10:44 Board Mechanics and Founder Control13:06 Investor Strategies and Founder Leverage18:34 Facing the Reality of Founder Reassignment23:17 Famous Comebacks: Steve Jobs, Howard Schultz, and Jack Dorsey24:36 The Emotional Toll of Being Replaced25:10 Turning Emotions into Positive Actions25:46 Negotiating Your Exit Strategy30:54 Crafting Your New Role31:55 The Importance of Maintaining Relationships37:00 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 Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:01:01 Personal Burnout Stories04:46 The Hidden Costs of Burnout08:41 Recognizing and Addressing Burnout19:17 Recognizing Emotional Burnout19:47 Impact of Economic Downturn on Founders21:19 Personal Struggles and Their Impact on Work22:13 Diagnosing and Addressing Burnout in Teams23:04 The Importance of Personal Life in Preventing Burnout27:32 Strategies for Treating Burnout29:27 Finding Passion Outside of Work32:59 Identifying and Mitigating Burnout Triggers38:25 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 Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:26 The Reddit Experiment: Stirring Controversy03:53 The Time Compression Revelation04:32 Analyzing Time Management07:52 The Cost of Meetings and Conversations15:21 The Impact of Family on Work Hours17:44 The Power of Constraints20:02 The Power of Saying No20:24 Focus as a Job20:34 Timeless Solutions21:06 The Importance of Prioritization21:34 Efficiency in Communication22:34 Breaking Down Big Tasks23:14 Consistency and Compounding23:25 Building a House with Focus26:53 Weekly Timelines for Productivity36:12 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 Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:42 The Myth of Alignment in Startups01:06 Investor Alignment: Fact or Fiction?01:48 The Role of Spouses in Startup Alignment03:09 The Challenge of Aligning with Employees04:59 Generational Differences in Work-Life Balance14:50 The Reality of Co-Founder Alignment21:16 The Challenge of Co-Founder Alignment22:45 Spousal Support and Startup Life25:45 Understanding and Managing Differences28:31 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 Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:25 The Beverly Hills House Dilemma03:05 Reflecting on Sacrifices and Payoffs06:52 The Decision to Move Back to Ohio13:42 The Value of Freedom and Purpose17:46 The Danger of Undefined Goals22:15 The Illusion of Goals23:19 Realizing Unwanted Desires24:13 Shifting Ambitions26:21 The Fear of Losing Ambition27:54 Evaluating Sacrifices33:48 Finding True Fulfillment36:31 Building a Dream42:38 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-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:52 The Myth of the Big Exit01:52 Emotional and Psychological Impact of Wealth02:58 The Speech: Congrats, Now Don't Mess It Up04:23 Financial Management for Newfound Wealth06:11 The Three Js of Wealth: Judgment, Jealousy, and Jockeying06:47 The Importance of Keeping Financial Information Private20:06 The Shift from Offense to Defense in Wealth Management22:24 The Founder Mentality Shift23:53 The Casino Analogy26:45 The Importance of Playing Defense30:18 The Danger of Proving Yourself Again36:33 The Save Point Strategy44:19 The Burn Rate Dilemma45:24 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-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:07 The Founder’s Dilemma: Knowing When Enough is Enough01:26 The Scarcity Mindset and Its Impact02:35 The Law of Diminishing Returns03:12 Personal Anecdotes on Ambition and Satisfaction05:38 The Concept of Utility in Economics12:00 Balancing Growth and Happiness in Startups16:56 Post-Exit: The Risk of Overreaching20:11 The Downfall of a Legend21:15 The Cost of Ambition22:32 The Utility of Wealth23:25 Chasing More: A Founder’s Dilemma25:42 The Search for True Happiness28:48 Redefining Success33:50 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-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:40 The Power of Entrepreneurship to Alleviate Poverty01:17 Personal Stories of Entrepreneurial Beginnings02:34 The Ripple Effect of Entrepreneurship03:38 Teaching Entrepreneurship as a Lifelong Skill04:46 Hope as the Foundation of Entrepreneurship05:37 Early Wins and Their Impact07:17 The Importance of Small Wins08:20 The Role of Hope and Pride in Entrepreneurship12:15 The Willingness to Fail22:49 The Risk of Failure for the Broke23:45 Historical Context and Immigrant Success Stories24:46 The Luxury of Credit and Capital27:03 Entrepreneur Welfare and Venture Capital29:14 The Case for Minimum Basic Income for Founders29:40 The Parallel with Education and FAFSA38:47 The Need for Structured Entrepreneurship Education39:47 The Role of Hope and Security in Entrepreneurship45:46 Entrepreneurship as a Solution to Poverty47:34 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-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:08 The Illusion of Startup as a Family00:55 Early Career and Peer Dynamics01:50 The Reality of Founder-Employee Relationships03:46 The Pitfalls of Treating Employees as Family05:54 Transparency in Startups: A Double-Edged Sword07:13 Shared Risk and Misinterpreted Bonds09:32 The Inevitable Strain on Relationships12:17 The Limits of Friendship in Startups16:18 The Evolution of Team Dynamics18:12 A Throwback to Early Company Culture18:31 The Impact of a New Hire19:19 Cultural Misalignment and Realization20:15 Adjusting Company Culture21:43 Balancing Professionalism and Empathy22:50 The Importance of Boundaries24:18 The Dangers of Forced Inclusivity28:24 Personal Experiences with Cultural Fit32:20 The Family vs. Professional Sports Team Metaphor36:42 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-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:34 Can AI Replace Founders?01:16 The Evolution of AI Capabilities02:03 AI's Impact on Copywriting and Creativity03:28 AI in Advertising and Idea Generation04:44 Embracing AI for Efficiency06:31 AI as a Force Multiplier09:44 The Future of AI and Founders14:36 AI in Coding and Development17:08 Leveraging AI for Business Growth19:13 Simulating Business Scenarios with AI19:38 The Role of AI in Business Decision Making19:53 The Timeless Nature of Business Challenges20:48 Embracing AI for Efficiency21:12 The Unique Human Element in Business23:40 The Future of Founders in an AI-Driven World25:50 The Evolution of Founders' Roles28:05 Leadership and Determination in Business30:47 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-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:27 The Identity Crisis of Achieving Goals01:05 Personal Reflections on Goal Setting02:25 The Evolution of Goals Over Time04:14 The Reality of Achieving Big Goals07:04 The Trap of Sensationalizing Goals10:58 The Diminishing Returns of Goal Achievement19:06 The Two Paths of Goal Setting: Pleasure vs. Pain20:40 Understanding Pain and Relief21:42 The Myth of Success Equals Happiness22:32 Existential Goals and Realizations23:31 The Challenge of Finding Fulfillment25:23 Enjoying the Journey vs. The Destination29:12 Reevaluating Ambitions and Goals33:11 Building for the Sake of Creation36:59 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-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:43 The Journey to Becoming a Founder01:28 Reinventing Yourself as a Founder02:31 The Value of Diverse Experiences03:55 A Humorous Job List08:11 The Role of Exposure in Career Choices13:06 Breaking Free from Career Constraints19:46 Early Career Hustles20:22 Learning from Experience20:53 First Sales Job21:30 Unexpected Opportunities23:22 Reinvention Starts Small24:06 Curiosity and Career Growth26:14 Building Skills Over Time28:04 The Power of Starting Small30:10 Embracing Continuous Learning32:21 The Value of Diverse Experiences39:59 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-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:01:05 The Paradox of Connection and Loneliness02:36 Impact of Remote Work on Founders16:17 The Role of Social Media in Isolation20:49 The Distorted Reality of Social Media21:24 The Cynicism Towards Social Media Posts22:19 Creating Private Spaces and Personal Connections23:15 Declaring Relationship Bankruptcy26:53 The Impact of AI on Authenticity31:08 The Future of Human Interaction in a Digital World35:33 Combating Isolation as Founders