Startup Therapy

What if the thing that looks like a distraction is actually the move that saves your startup? This episode breaks down why the “stay focused at all costs” advice can be risky when you’re still figuring out what actually works. The hosts challenge the myth of the linear startup path, arguing that side quests—small, intentional experiments with capped downside—create learning, reduce single points of failure, and help you earn the right to pivot with evidence instead of vibes. They share how Fundable’s early equity crowdfunding push revealed founders were unprepared to raise money, which led to a major side quest: doing diligence on about 100 companies, talking to 200+, and acquiring six venture-backed businesses—work that became the genesis of startups.com. Along the way, they highlight the value of the quest itself (market intel, understanding what not to do, faster learning) and even mention an extreme near-distraction: briefly considering buying Atari. The conversation also reframes common “side quests” like doing services work while building a product, arguing that bringing in revenue to stay alive isn’t a distraction—it’s the business. They clarify the difference between a side quest (exploration) and a pivot (committing to a new direction), and point to the podcast itself as an example of a side quest that became a major long-term asset after a rough start. What to listen for: 00:40 The AI Newsletter Moment That Sparked the Topic 01:47 What a “Side Quest” Means for Founders 03:45 The Myth of the Linear Startup Path 06:34 When Focus Becomes a Liability: Certainty, Ego & Roadmaps 10:04 Side Quests as the Ongoing Lab (and Why It Never Ends) 12:01 Case Study: Fundable 2012 and the Crowdfunding Gold Rush 15:48 The Pivot: Founders Needed Help, Not Just a Platform 18:07 Side Quests Done Right: Controlled Experiments (…and Almost Buying Atari) 18:42 The Wild Idea: Almost Buying Atari (Nostalgia vs. Distraction) 19:48 Why Side Quests Matter: Learning More Than the Outcome 20:42 Founder-Forward Deal Talks & Market Intel as a Force Multiplier 22:10 Side Quests as “Insurance”: Selling the Learning to Skeptics 23:48 The Classic Startup Side Quest: Services to Pay the Bills 27:14 Side Quest vs. Pivot: Exploration First, Commitment Later 27:52 The Podcast as a Side Quest That Became Core to the Business 30:26 Earning the Right to Pivot: Evidence, Courage, and Finding Truth 34:20 Closing: De-Risking Through Exploration + Startups.com Community Invite 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 if failure isn’t something to avoid, but a skill to master? This episode breaks down why startups can’t be built on certainty—new markets, new products, and new teams mean you’re guaranteed to be wrong a lot. The goal isn’t to “be right,” it’s rapid error correction: make decisions, ship anyway, learn fast, and recover even faster. The conversation covers how avoiding failure leads to paralysis (“steering a parked car”), why indecision compounds in startups, and how to reduce risk by keeping failures small, reversible, and frequent (kill switches, stop rules, and capped losses). They share early personal stories—school fights and a childhood cattle business collapse—to show how overcoming real consequences builds confidence and resilience. Practical examples include choosing an ICP quickly, improving poor conversion rates through iteration, using vesting/cliffs when picking co-founders, and why even top VCs still miss constantly. The key takeaway: the most dangerous competitor is the one who isn’t afraid to get hit, recover, and keep coming back—because that’s as close to “invincible” as a founder can get. 02:01 Failure Isn’t the Enemy: Stop Optimizing for Being Right 02:59 The Founder Reality: Uncertainty, Rapid Error Correction & the Boxing Analogy 03:44 Safety vs Startups: Why Most People Avoid the Risk 05:24 ‘Steering a Parked Car’: Indecision Kills Startups 07:54 Make the Call, Learn Fast: Small Failures, Big Truths 09:02 We’re Conditioned to Fear Failure (School, Work, Relationships) 11:59 Will’s Origin Story: Jason Barker and Learning to Beat the Monster 14:48 Choosing to Fail on Purpose: Turning Fear into a Superpower 17:06 Ryan’s First Big Failure: The Farm/Cattle Business Lesson Begins 17:45 Cash-Strapped Expansion: Inventory Leverage & a Brutal Winter 18:09 When the Side Hustle Needs a Side Hustle (and the Cost of Neglect) 18:35 Failing Hard at 12: Losing Animals and Learning to Plan 19:51 Founders Don’t Win by Being Right—They Win by Taking Hits 21:36 Shipping While Wrong: Marketing Experiments, MVPs, and Momentum 22:51 Hiring, Co-Founders & Investors: Why Nobody Can Pick Perfectly 24:00 The Real Skill: Recovering From Failure (Resilience as a Reflex) 30:26 Small Blast Radius, High Frequency: Reversible Bets & Kill Switches 31:13 Failure Is Portable: Building a House, Living ‘Why Not,’ No Regrets 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:

Is AI truly the game-changer for startups, or does it bring unexpected chaos? This episode dives into how AI is transforming forecasting, marketing, product development, employment, and investment in the startup ecosystem. Ryan Rutan and Will Schroter discuss the rapid pace of change brought by AI, including the exciting opportunities and the unsettling uncertainties. They explore how traditional pillars of business like hiring, marketing, and customer acquisition are being upended, creating both new challenges and avenues for innovative founders to thrive. Tune in to understand how to navigate this AI-driven landscape and leverage the chaos for maximum impact. 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 and Future Predictions 00:49 The Impact of AI on Business Models 02:06 AI's Rapid Advancement and Market Disruption 04:17 Challenges in Marketing and Content Creation 10:04 Hiring and Talent Management in the AI Era 15:18 Product Development and Market Relevance 17:04 Industries Vanishing Overnight 17:32 The Accelerating Pace of Change 18:20 Investment in the Age of AI 19:07 The Future of Startup Funding 22:31 The Shrinking Moat of AI 24:54 Compounding Anxiety in the Startup Ecosystem 33:37 Founders: Built for Chaos 35:53 Embracing the Problem Business

How has the relentless pursuit of efficiency, aided by tools like remote work, Zoom, Slack, and AI, affected our human connections? In this episode, we're exploring the cost of optimized workflows on our humanity. We delve into personal anecdotes and discuss the ramifications of isolation in the workplace and the loss of shared experiences. We also contemplate the importance of reintroducing human interactions to ensure a balanced, connected, and more fulfilled work environment. 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 Loneliness of Optimized Efficiency 01:48 The Impact of Remote Work on Human Connection 04:14 The Rise of AI and the Decline of Human Interaction 12:41 The Evolution of Remote Work Culture 17:20 The Dystopian Reality of AI Conversations 20:22 The Importance of Laughter and Human Interaction 21:23 Leveraging GPT for Problem Solving 22:18 The Downside of Relying on AI 23:45 The Value of Human Interaction in the Workplace 25:09 The Impact of AI on Team Dynamics 27:04 Balancing Efficiency and Human Connection 29:05 The Future of Startups and Human Connection 30:33 The Need for Human-Centric Work Cultures 32:06 Conclusion: Embracing Humanity in the Age of AI

What will AI do to everything? In this episode, we explore how AI is set to create a surge in new startups, reshaping employment as we know it. As jobs get displaced, the concept of big employment shifts, giving rise to smaller, more agile companies using AI tools. Drawing parallels with past technological revolutions, we highlight the opportunities that lower costs and new market demands present for founders. We discuss the transformation in various sectors, from customer service to content creation, and emphasize how AI can democratize entrepreneurship globally. Finally, we delve into the exciting potential for startup growth and the role of AI as both a tool and a transformative force in the startup ecosystem. 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 Impact of AI on Employment 01:16 Historical Parallels: Internet and Industrial Revolution 02:32 The Shift from Big Employment to Entrepreneurship 03:16 The Decline of Traditional Jobs 05:25 Opportunities in the New Economy 11:48 The Rise of the Creator Economy 20:15 Macro Trends and Future Outlook 23:52 The Rise of Billion-Dollar Startups 24:24 Price Collapse and Premium Experiences 26:01 The Impact of AI on Startups 26:44 The Creator Economy and Niche Markets 29:06 The Evolution of eSports 31:09 The Dawn of Young CEOs 33:22 The Future of Entrepreneurship 39:43 Global Entrepreneurship and Accessibility 45:56 The Age of the Startup

Ever felt like vacations just aren't cutting it when it comes to startup burnout? In this episode, Ryan Rutan and Will Schroter dive deep into why burnout is inevitable for founders and how quick fixes like vacations often fail to address the root of the issue. They explore how to truly recover and maintain that all-important spark in your work. Learn why it's crucial to inventory what drains and fuels your energy, and how making meaningful changes—not just taking time off—can lead to sustainable recovery. Real-life examples and practical advice make this a must-listen for any founder feeling the grind. 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 The Misconception of Business Success and Burnout 01:00 Personal Stories of Burnout 02:10 The Ineffectiveness of Vacations 03:49 The Importance of Meaning in Work 04:11 Personal Struggles with Burnout 07:27 The Real Cause of Burnout 10:23 Balancing Tasks to Prevent Burnout 11:59 The Battle Within: Struggles in the Workplace 12:58 Startup Expectations vs. Reality 13:46 Finding Energy and Avoiding Burnout 15:34 The Importance of Positive Energy 18:22 Active Breaks for Founders 22:32 Identifying and Addressing Burnout 25:31 Join the Startups.com Community

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 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 Delusional Optimism of Founders 01:02 Creating and Living in a Fantasy 02:00 Running Toward Chaos 04:54 The Passion and Drive of Founders 05:59 The Reality of Startup Life 12:08 The Role of Belief and Proof 14:31 Finding Optimism in Small Wins 16:40 Persistence in the Face of Rejection 18:56 The Power of Hope in Business 19:52 The Role of Optimism in Startups 21:41 Balancing Optimism and Honesty 23:03 The Fine Line Between Optimism and Deception 26:07 The Importance of Optimism in Leadership 28:55 The Role of Optimism in Overcoming Challenges 32:05 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 Story 02:24 The Illusion of Popularity vs. Productivity 06:21 The Modern-Day Equivalent: Social Media 09:24 Balancing Publicity and Productivity 11:23 Cautionary Tales and Lessons Learned 12:55 The Importance of Focus and Balance 14:48 Earning the Right to Brand Build 15:29 The Pitfalls of Prioritizing Popularity Over Business 16:07 The Honeymoon Period of Venture Funding 17:40 The Dangers of Personal Branding for Founders 18:47 When Personal Views Hurt Business 21:39 Balancing Personal and Company Brand 23:48 Focus on Building the Business First 30:22 The Cost of External Interactions 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:

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 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: 00:14 The Myth of Bigger is Better 00:43 Examples of Companies That Grew and Suffered 02:00 The Hidden Costs of Scaling 05:08 Personal Experiences with Growth Challenges 13:01 The Importance of Freedom and Quality 17:18 The Hidden Costs of Growth 17:58 Balancing Growth and Quality of Life 20:39 Defining Non-Negotiables for Better Business 22:33 Scaling with Soul: Maintaining Company Culture 24:41 Quality Over Quantity: Making Strategic Decisions 28:07 The Power of Saying No 31:15 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 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 Consequences of Unfiltered Honesty 01:26 Generational Differences in Professionalism 02:44 The Power Dynamics of Founders 04:45 Balancing Honesty and Diplomacy 06:01 The Luxury of Honesty and Risk 08:04 The Importance of Filtering Communication 12:56 The Duality of Professional Personas 15:21 The Consequences of Honesty in Leadership 16:19 Balancing Honesty and Diplomacy 17:10 The Importance of Empathy in Communication 18:26 The Cost of Unfiltered Honesty 19:51 Frameworks for Effective Communication 20:55 Lessons from the Terminator: Choosing Responses Wisely 22:07 The Role of Diplomacy in Leadership 28:17 The Medium Matters: Hot, Warm, and Cold Communication 29:56 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 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: 00:33 Founders and Their Problems 01:15 Pharmaceutical Industry Insights 02:36 Social Media and Problem Creation 03:46 Personal Struggles of Founders 05:07 Overthinking and Control Issues 11:15 ADHD and Academic Challenges 17:11 Harnessing Obsessiveness for Success 20:40 Evaluating Self-Help Advice 21:09 Struggles with Attention Span 21:31 Learning Outside Traditional Education 22:15 Emphasizing Strengths Over Weaknesses 23:29 Founders and Their Strengths 28:08 Anxiety as a Superpower 34:46 The Importance of Context in Learning 38:36 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 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