Startup Therapy

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

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-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:00:58 Building Confidence Through Practice05:25 The Power of Curiosity09:25 Asking the Right Questions14:58 Taking on New Challenges19:03 Building Confidence Through Small Victories19:40 Teaching Kids Micro Challenges20:09 Challenging Yourself Incrementally21:17 The Line Between Ambition and Recklessness22:19 Learning Through Incremental Steps25:37 The Importance of Being Wrong27:41 Building Confidence as a Founder31:33 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-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:00:17 The Value of a College Degree for Founders00:55 Challenging the College Norm01:37 A Real-Life Example: Skipping College for Startups03:14 Generational Expectations and College07:25 The Economics of College Education08:04 The Financial Impact of College vs. Investing14:19 The Opportunity Cost of College for Founders20:21 The Power of Compounding Experiences20:35 Learning at Your Own Pace20:58 The Irrelevance of Traditional Education22:19 Founders Need a Broad Skillset22:57 The Limitations of College24:33 Alternative Learning Paths25:57 The Value of Practical Experience27:44 The Diminishing Value of a College Degree29:13 Questioning the College Path33:30 The Founder Mindset40:18 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-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:00:51 The Myth of the Perfect Plan02:04 The Uber Example: Evolving Business Models03:55 The Importance of User Feedback04:48 Facing Investor Expectations07:44 Ego vs. Agility in Decision Making08:47 The Afford It Story: Lessons Learned13:21 Conclusion and Final Thoughts13:53 The Original Plan and Its Challenges14:25 Admitting Mistakes and Moving Forward15:10 Evolving as a Founder15:58 The Birth of Startups.com17:26 Learning from Market Feedback20:45 Detaching Ego from the Product23:14 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-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:00:32 The Pool Story: A Lesson in Work-Life Balance02:08 The Toxic Relationship with Work03:11 Startup Therapy: The Podcast's Origin08:15 Balancing Work and Family13:17 Non-Negotiables and Personal Values14:51 Conclusion and Final Thoughts15:35 Mitigating Guilt Through Productivity17:29 The Elusive Goal of Profit19:21 Emotional ROI in Startups21:57 Autonomy and Company Culture24:50 Balancing Safety and Happiness28:26 Avoiding the Trap of Obligations29:40 Creating a Non-Abusive Startup Relationship30:50 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-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:00:31 The Unexpected Reactions to Success02:54 Personal Stories of Resentment07:57 The Impact of Success on Relationships12:32 Social Media and Validation14:01 Processing Success and Insecurities19:34 Navigating Conversations About Success21:04 The Validation Loop Dilemma21:21 Caring About Others' Opinions21:57 The Spectrum of Self-Presentation23:17 The Insecurity Behind Social Media Influencers25:34 The Cost of Flaunting Success29:04 Extreme Humility and Its Consequences32:19 Balancing Humility and Pride37:01 The Art of Humble Bragging40:39 Avoiding Resentment Through Humility41:46 The Power and Responsibility of Success42:38 Join the Startups.com Community

In this episode of the Startup Therapy Podcast,Ryan and Will delve into the emotional journey of startup founders who feel out of place in the very companies they built from scratch. They discuss the guilt and struggle founders experience when their roles change and they no longer enjoy their jobs. They share personal anecdotes and examine the impact of forced roles, from management misfits to a loss of personal fulfillment. The duo also explores the concept of evolving with or beyond your startup, and how to come to terms with these difficult but often necessary transitions.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:00:48 The Shift from Building to Managing01:29 The Struggles of Management02:13 The Evolution of Roles04:17 The Peter Principle in Action05:29 The Emotional Toll of Management08:34 Reflecting on the Past and Moving Forward09:57 The Realization and Acceptance12:39 The Dilemma of Founder Evolution13:10 Learning from the Past13:42 Commitment and Introspection15:02 The Cost of Doing What You Hate17:40 Recognizing and Embracing Change20:16 The Hard Decision to Move On25:03 Celebrating Growth and Moving Forward

Ryan and Will discuss the psychological challenges founders face by constantly looking ahead and rarely celebrating their achievements. They explore how important it is for founders to practice gratitude and recognize their progress, even if their ultimate goals haven't been reached. The conversation delves into personal experiences, including Ryan's move to Guatemala and Will's time in Beverly Hills, highlighting how perspective and gratitude can significantly impact one's satisfaction and motivation in their entrepreneurial journey.Resources:Startup Therapy Podcast https://www.startups.com/community/startup-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:00:29 The Psychological Cost of Milestones00:58 The 1% of Startups02:01 Celebrating Small Wins02:38 The Comparison Trap03:45 Balancing Credit and Complacency04:33 Contrasting Success Stories09:14 Perspective on Startup Success16:26 The Olympic Mindset and Startup Mentality17:39 The Power of Perspective and Gratitude19:35 Balancing Ambition and Gratitude21:16 Family Traditions and Simple Joys22:47 Reinforcing Self-Worth and Capability28:19 The Curse of the Exited Founder31:02 Changing Perspectives for Greater Happiness

Dive into the common struggle founders face with burnout and the inability to truly relax. Ryan and Will  share their personal experiences and discuss how traditional relaxation methods often fail for them. Instead, they highlight the importance of finding other meaningful and challenging obsessions outside of work to channel their energy. From woodworking and home-building to martial arts, they explore how these activities can provide a sense of accomplishment, progression, and actual mental rest, ultimately making them better and more effective in their startup journeys. Tune in to gain insights on how to recharge as a founder by embracing big, consuming projects that challenge and fulfill you.Resources:Startup Therapy Podcast https://www.startups.com/community/startup-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:00:44 The Struggle with Relaxation01:36 Failed Attempts at Relaxation03:32 Vacation Dilemmas05:52 The Need for Mental Engagement09:47 The Importance of Completion14:07 Finding New Problems to Solve22:10 Woodworking as a Solution24:13 The Obsession Begins: From Birdhouses to Building a House24:48 The Challenge of Building a House from Scratch25:35 Balancing Work and Passion Projects26:31 The Importance of Completion and Physical Activity27:53 Managing Overwhelm and Finding Solutions29:14 The Power of Small, Consistent Efforts30:22 The Role of Meaningful Side Projects33:17 The Need for Mental and Physical Challenges36:21 The Value of Overwhelming Projects

Ryan and Will discuss the prevalent fear in the market due to economic uncertainty in April 2025. They delve into how fear is a constant companion for founders and argue that it's not a weakness but a strength. Drawing on personal experiences, including public speaking and risky business moves, they illustrate how leaning into fear can drive massive growth and success. Comfortable activities rarely lead to significant achievements, they argue, emphasizing that true progress requires embracing discomfort. They also highlight the importance of conditioning oneself to fear and rejecting complacency to ensure continuous growth and impactful outcomes.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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:|00:35 Founders' Relationship with Fear01:35 Fear as a Motivator and Asset02:38 Personal Experiences with Fear and Risk03:17 Balancing Risk and Reward in Decision Making06:36 The Role of Fear in Entrepreneurship07:05 Cultural Differences in Risk Perception12:57 Embracing Fear as Part of the Job14:55 Building Resilience Through Failure15:39 Embracing Fear in Business16:02 The Role of Fear in Motivation17:46 The Danger of Complacency19:25 Taking Big Risks for Big Rewards21:23 Balancing Fear and Progress25:44 Facing Public Speaking Fears30:08 The Importance of Leaning Into Fear

In this episode, Ryan and Will discuss the common misconception that startups need funding before generating revenue. They emphasize that the actual business isn't just the product but the revenue it generates. The discussion covers various strategies to bootstrap and generate cash flow, including building a minimal viable product, offering related services, and even taking on side gigs or unconventional methods to bring in money. By doing so, startups can extend their runway and better validate their business model before seeking significant investment. The episode includes examples from famous startups like Zappos and Airbnb to illustrate these points.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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:|00:51 The Broken Assumption About Funding01:29 Generating Revenue Before the Product02:39 Examples of Early Revenue Generation03:07 The Zappos Story: Validating Demand08:06 Personal Anecdotes on Testing Demand10:27 The Importance of a Minimum Viable Product18:39 Service-Based Proxies for Products21:21 The Unexpected Success of Pitch Deck Services22:04 Assumptions About Entrepreneurs and Investors23:48 The Role of Services in Startup Success25:33 The Importance of Revenue and Profitability28:53 Creative Ways to Fund Your Startup34:10 The Value of Bootstrapping and Hustle

Will and Ryan discuss the dangerous mindset founders can fall into after hitting it big with their startups. They reflect on the story of Peter Chesky, co-founder of Wish, who became a billionaire during the tech IPO boom of early 2021 but saw his net worth plummet as the company's stock tanked. The episode emphasizes the importance of treating any major payout as if it's the last one you'll ever receive. With only a small percentage of startups ever having significant exits, and even fewer doing it repeatedly, Ryan and Will stress why founders should be cautious with their newfound wealth instead of assuming it will keep flowing.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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:01:01 The Rise and Fall of Wish03:01 Lessons from the Wish IPO05:15 The Psychology of Founders11:52 A Counter Story: Priceline's IPO15:13 Reflecting on High School Memories15:37 The Illusion of Endless Wealth15:51 The Reality of Financial Downturns19:09 Understanding Venture Capital Statistics21:28 The Rarity of Repeat Success24:18 Advice for Founders: Secure Your Wins28:11 The Importance of Financial Safety30:39 Final Thoughts: Keep the Win

Ryan and Will discuss the evolution of startup location strategies. They reminisce about the bygone era when relocating to major hubs like San Francisco was essential for success due to access to talent, investors, and networking opportunities. Now, with advancements in remote work, AI, and digital connectivity, these factors have become less relevant. Ryan and Will delve into the changing dynamics of raising capital, building teams, and cultivating networks without needing to uproot one's life to a specific city.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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:00:39 The Shift in Startup Location Importance01:46 Reevaluating the Need to Move for Startups01:58 The Impact of Remote Work and COVID-1903:51 Debating the Necessity of Moving to San Francisco06:12 Talent Acquisition in the Remote Work Era09:23 Financial Considerations and Cost of Living15:10 The Role of Investors in the New Startup Landscape17:54 Questioning the Need for Large Engineering Teams18:21 Capital Requirements and Investor Expectations19:14 The Evolution of Pre-Seed Rounds22:27 The Impact of Technology on Investment23:43 Relocating for Networking Opportunities27:13 The Shift in Startup Location Necessities32:03 The Value of Flexibility in Startup Locations35:59 Conclusion: Startups Can Thrive Anywhere

In this episode of the Startup Therapy Podcast, the guys tackle the big question: was the entrepreneurial journey worth it? They discuss the sacrifices, the missed experiences, and the immense pressures that come with being a founder. Will shares a touching story about his daughter's unprompted appreciation for his hard work, leading to a reflection on whether the grinding was worth the outcome. Both hosts also highlight the freedom, flexibility, and the unique sense of achievement they've gained. However, they caution about the inevitable costs and the importance of balancing life and startup aspirations. A must-listen for anyone questioning the value of their entrepreneurial path.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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:00:49 A Moment of Gratitude02:42 Was It All Worth It?06:02 Missed Experiences and College Life11:00 The Weight of Responsibility15:12 Habits and Hardships19:32 Guilt and Work-Life Balance24:20 The Timeless Nature of Startup Challenges24:52 The Hidden Costs of Success25:47 The Value of Sacrifice26:39 The True Meaning of Freedom28:04 The Journey to Personal Agency29:20 The Impact of Entrepreneurship31:15 The Irony of Wealth and Freedom35:12 The Cost of Corporate Success45:44 Balancing Life and Startup

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter discuss how childhood experiences influence the entrepreneurial journey. They explore why many founders' origin stories trace back to their early years and how formative events can plant the seeds of entrepreneurship. Will shares his personal story of selling candy as a child, highlighting moments that taught him vital business skills. The conversation also delves into the importance of agency, the tools needed for entrepreneurial success, and the role of parents in nurturing a child's potential to create their own path.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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:00:13 Exploring Founder Origin Stories01:51 Will's Childhood Story10:14 The Power of Agency10:53 Teaching Kids About Agency20:54 Personal Reflections on Agency21:22 The Power of Agency and Optimism22:14 Parental Protection vs. Empowerment22:40 Real-Life Stories of Overcoming Adversity24:40 The Magic of Agency in Hardship26:42 Tools for Founders and Kids27:23 Early Lessons in Entrepreneurship34:56 The Importance of Sales Skills42:29 Teaching Kids the Value of Agency43:22 Join the Startups.com Community

In this episode of Startup Therapy, Ryan Rutan and Will Schroeter challenge the startup world's focus on big exits and venture capital. They highlight the benefits of cash-flowing businesses, showing how consistent profits can lead to financial security. Using real examples, they explain how making $10K a month can be as powerful as having millions in the bank—emphasizing sustainable growth and long-term success.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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:00:19 The Value of Consistent Cash Flow01:23 Examples of Profitable Local Businesses03:37 The Misconception of Startup Exits03:49 Real-Life Stories of Successful Small Businesses06:16 The Broken Narrative of Startup Wealth07:26 Reevaluating Business Success Metrics09:05 The True Value of a Profitable Business09:38 Calculating the Financial Impact13:20 The Reality of Business Exits18:09 Replacement Value vs. Exit Value19:14 The Value of Experience and Pre-existing Solutions19:39 Cash vs. Business Value: A Deep Dive20:21 Real-life Examples of Business Growth23:34 Risks and Rewards of Running a Business27:12 The Importance of Consistent Earnings34:54 Long-term Value and Compounding Effects

In this episode of the Startup Therapy podcast, Ryan and Will chat about how startup success isn't always a straight path. They use Mark Cuban's story as a prime example, showing why sticking it out for the long run is so important—because success can happen at any time in a founder's career. They also talk about how those early small wins can build up to something bigger and why setting strict timelines for success doesn't really make sense. At the end of the day, one big right moment in a 50-year career can be a total game-changer.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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 Reality of Founders' Success02:00 Mark Cuban's Journey to Billionaire Status06:35 The Importance of Small Wins10:15 Financial Stability and Early Success15:57 The Value of Consistent Small Wins18:02 Success Doesn't Have a Timeline18:12 When Does Success Happen?18:20 Examples of Late Bloomers18:45 The Myth of Early Success19:59 The Impact of Timing20:44 The Internet Era and Young Wealth21:40 Outliers and Unrealistic Expectations25:13 Consequences of Chasing Quick Success27:28 The Value of Longevity in Business30:02 Unexpected Success Stories31:46 Staying in the Game32:36 Join the Startups.com Community

In this episode of The Startup Therapy, Ryan Rutan and Will Schroter explore the 'what if' scenarios that often preoccupy founders. Will shares personal milestones, showing how taking bigger risks shaped his journey. They discuss the hidden costs of success, the pitfalls of romanticizing alternative outcomes, and the importance of realistic risk assessment. The key takeaway? Embrace risk to avoid the regret of missed opportunities.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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 – Reflecting on milestones and 'what ifs'00:44 – The risks and rewards of entrepreneurship04:00 – A hilarious temp job experience07:34 – The reality of alternate paths09:02 – The danger of romanticizing 'what ifs'13:48 – The cost of success15:29 – Building a realistic mental model16:18 – Stop guessing and get real answers16:26 – The cost of staying in a job you hate17:30 – Should you stay or leave?18:10 – The true cost of success19:12 – The hindsight trap: romanticizing outcomes21:56 – Learning from failure and modeling risk22:55 – Zirtual acquisition: a case study in risk28:47 – Surviving failure and moving forward31:35 – Avoiding regret and embracing risk

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter dive into an interesting perspective: taking risks in entrepreneurship is actually a luxury, not the norm. They break down what it really costs to take risks, how to figure out your "minimum viable risk pool," and why having a financial cushion is key to surviving setbacks.They share personal stories from their experience at Startups.com, emphasizing the importance of cutting personal and business expenses to stretch your runway and make smarter decisions. This episode is all about helping entrepreneurs understand the financial milestones they need to hit to keep their businesses afloat—and how time plays a big role in navigating risks.This episode is packed with advice for anyone trying to manage the tricky balance of risk and reward in entrepreneurship. Tune in to learn how to take smarter risks and build a solid foundation for your business!Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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:00:15 Why Taking Risks Is a Luxury02:08 Balancing Personal and Business Costs03:44 Lessons from Startups.com05:55 Why You Need a Risk Buffer10:25 Figuring Out the Minimum Viable Risk Pool16:51 Financial Discipline and Budgeting19:09 The Freedom Fund Explained26:51 How to Survive Financial Challenges

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroeter delve into the anxiety surrounding contentment in the startup ecosystem. They question the conventional wisdom that equates contentment with stagnation and probes whether startup founders should aim for contentment as a goal. Through personal anecdotes and industry examples, they explore the influence of perpetual ambition and societal expectations on entrepreneurs. They also discuss the differences between being content and being complacent and reflect on the continuous urge to chase new problems and challenges, even when previous goals have been achieved.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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:00:44 Questioning the Need for a Business Coach02:05 The Dilemma of Contentment vs. Ambition04:02 Reflecting on Milestones and Contentment07:35 The Nature of the Startup World15:23 Anxiety as a Driving Force20:51 The Anxiety of High Achievers22:11 The Pressure of Success: Avicii and Pharrell23:59 Imposter Syndrome Among Overachievers26:21 The Elusive Goal of Contentment29:08 Balancing Ambition and Contentment33:29 The Trap of Endless Ambition40:44 Finding True Satisfaction

Ryan Rutan and Will Schroeter discuss the complexities and challenges faced by startup founders, particularly the frequent occurrence of founders being replaced by investors. The conversation delves into the motivations behind such investor decisions, the difficulties in replicating a founder's passion and vision, and the common pitfalls and consequences of these transitions. The hosts share personal anecdotes and provide insights on how to prevent these situations, handle them professionally if they arise, and maintain valuable stakeholder relationships. This episode is a must-listen for any startup founder navigating the turbulent waters of investor relations and company growth.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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:00:25 The Downfall of Bench and Ian Crosby's Story01:54 Investor Motivations and Founder Replacements03:33 Understanding Investor Expectations05:40 The Slow Burn of Founder Dismissal08:23 The Impact of Replacing Founders13:49 Personal Stories of Founder Replacement16:47 The Challenges of Replacing Founders19:26 Augmenting the Team vs. Replacing the Founder22:01 Why Investors Push Founders Out24:00 Navigating Earn-Out Periods in Acquisitions24:26 The Challenge of Replacing Founders26:43 Timing the Transition: Leadership vs. Management29:08 The Mercenary CEO: Pros and Cons35:31 Investor Expectations and Founder Realities42:19 Handling Founder Exits Professionally

In this episode Ryan and Will delve into the intense pressures faced by founders from investors, peers, and the startup community. They discuss how these external expectations often drive founders to pursue goals misaligned with their personal beliefs and values. The conversation explores how unchecked expectations can lead to burnout and misguided efforts. They share insights on the importance of auditing and resetting personal and business expectations to ensure they align with one's true goals and values. The hosts also highlight the dangers of comparing oneself to other founders or industry giants, and emphasize the significance of building a business that meets personal fulfillment rather than external benchmarks.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/community/st...Websitehttps://www.startups.com/beginLinkedIn   / startups-co  Join our Network of Top Founders Wil Schroter  / wilschroter  Ryan Rutan  / ryan-rutan  What to listen for:00:32 The Source of Pressure and Expectations03:32 Investor Expectations and Their Impact04:05 Personal Story: Missing Investor Expectations05:44 The Reality of Investor Expectations10:15 Comparing Yourself to Other Founders17:45 The Peer Comparison Trap18:06 Personal Journey: From Poverty to Success20:01 The Futility of Social Media Comparisons23:07 Tying Success to Self-Worth28:20 The Illusion of Goals and Success31:53 Reevaluating Startup Expectations36:43 Conclusion: Building What Matters to You

Ryan and Will discuss the omnipresent challenges that come with running a startup. They delve into the perpetual 'shit storm' that founders face and share practical advice on how to keep moving forward even when everything feels like it's falling apart. Key points include regaining perspective, converting anxiety into actionable tasks, breaking down large goals into manageable micro-goals, and finding healthy obsessions to channel stress. They emphasize the importance of maintaining a positive outlook, not just for personal sanity but for the wellbeing of the entire team, and share personal anecdotes and strategies that have helped them through their toughest times.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/community/st...Websitehttps://www.startups.com/beginLinkedIn   / startups-co  Join our Network of Top Founders Wil Schroter  / wilschroter  Ryan Rutan  / ryan-rutan  What to listen for:00:07 The Perpetual Shit Storm of Startups01:01 Practical Advice for Founders in Crisis02:10 Regaining Perspective During Tough Times05:08 Personal Stories of Overcoming Challenges15:29 The Importance of Taking Action20:41 Managing Anxiety with Side Tasks21:58 The Power of Micro Goals23:37 Breaking Down Big Tasks26:29 The Importance of Focus32:07 Finding Healthy Obsessions41:08 Building Momentum with Small Wins43:14 Join the Startups.com Community

In this episode of the Startup Therapy Podcast, Ryan and Will delve into the often misunderstood motivations of venture capitalists. They discuss why investors push startups to grow rapidly, the pressures VCs face to deliver returns within a specific timeframe, and the fundamental differences between the stakes for founders and investors. The episode uncovers the reasons behind the 'push you off a cliff' approach, the impact of the 2 and 20 model on VC behavior, and the importance of understanding these dynamics to better navigate the startup journey.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/community/st...Websitehttps://www.startups.com/beginLinkedIn   / startups-co  Join our Network of Top Founders Wil Schroter  / wilschroter  Ryan Rutan  / ryan-rutan  What to listen for:00:11 Understanding Investor Motivations01:12 The VC Time Crunch03:57 Profit vs. Growth: A VC Perspective13:25 The Reality of VC Salaries16:29 Founders vs. Investors: Different Stakes19:00 Conclusion: Aligning Goals with Investors

In this episode of the Startup Therapy Podcast, Ryan and Will discuss the daunting realities of raising capital for startups. By sharing insights and experiences from both first-time and repeat founders, they delve into the recurring theme of regret found amongst entrepreneurs who've gone through the funding process. Topics include the hidden costs of raising money, the pitfalls of losing focus, and the challenges of working with investors. The hosts offer practical advice on when to raise funds, how to mitigate the risks of distraction, and the importance of being selective and strategic about bringing investors on board. Whether you're gearing up for your first round of fundraising or re-evaluating your approach, this episode provides valuable lessons to help navigate the complex landscape of startup financing.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/community/st...Websitehttps://www.startups.com/beginLinkedIn   / startups-co  Join our Network of Top Founders Wil Schroter  / wilschroter  Ryan Rutan  / ryan-rutan  What to listen for:00:14 The Reality of Raising Funds00:38 Founders' Regrets and Reflections02:15 The Perils of Not Getting Paid04:22 Understanding Founder Compensation11:04 Strategies for Better Compensation13:24 Challenges with Profitable Companies15:02 The Pressure to Grow or Bust15:16 The Dilemma of Raising Too Early15:47 The Vulnerability of Early Stages16:22 The Importance of Timing in Fundraising16:56 The Pitfalls of Early Funding17:28 The Distraction of Fundraising20:34 The Impact of Investor Expectations28:23 The Challenge of Having a New Boss31:50 Key Takeaways and Final Thoughts

In this episode of the Startup Therapy Podcast, Ryan and Will debunk the myth that each startup venture becomes progressively easier with experience. They explore the truths and fallacies surrounding repeat entrepreneurship, sharing personal anecdotes and insights from their extensive history of building and acquiring startups. Discussing expectation management, the double-edged sword of experience, and the harsh realities of repeating past mistakes, Ryan and Will emphasize that while experience offers certain advantages, it does not guarantee success in new ventures. They also highlight the emotional resilience required to endure the cyclical nature of startup challenges and the ever-present difficulties of achieving product-market fit and successful marketing, regardless of prior victories.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/community/st...Websitehttps://www.startups.com/beginLinkedIn   / startups-co  Join our Network of Top Founders Wil Schroter  / wilschroter  Ryan Rutan  / ryan-rutan  What to listen for:00:15 Debunking the Myth of Easier Startups01:27 The Double-Edged Sword of Experience02:32 Drawing from Multiple Experience Buckets05:15 Expectation Management in Startups09:39 Avoiding Duplicate Mistakes13:01 Raising Capital: Lessons Learned15:16 The Value of Experience in Decision Making17:07 The Reality of Investor Promises17:17 Understanding People: A Founder's Key Skill18:38 Emotional Maturity in Leadership20:00 Challenges That Never Get Easier21:57 The Ever-Changing Landscape of Product Market Fit25:39 Marketing Struggles for Experienced Founders27:40 The Pain of Failure: It Never Gets Easier31:30 The Value of Experience and the Role of Luck32:38 Join the Startups.com Community

Ryan Rutan and Will Schroter explore the intricate and often misunderstood relationship between founders and their startups. They tackle the question of whether the founder works for the startup or vice versa, challenging common perceptions shaped by societal views and political discourse. The hosts discuss the unspoken 'contract' entrepreneurs form with themselves, the inevitable trade-offs of startup leadership, and the sacrifices founders make for their companies. They emphasize the emotional and financial tolls on founders, the discrepancies in founder-employee dynamics, and the need for startups to stay aligned with the founder's original mission. This episode stresses the importance of maintaining control and balancing personal goals with the demands of the startup ecosystem.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/community/st...Websitehttps://www.startups.com/beginLinkedIn   / startups-co  Join our Network of Top Founders Wil Schroter  / wilschroter  Ryan Rutan  / ryan-rutan  What to listen for00:35 The Founder vs. Startup Dilemma00:51 Political and Economic Perspectives01:40 The Reality of Founders' Lives03:00 The Initial Contract of Founders05:11 The Shift in Founders' Roles06:15 The Permanent Struggle of Founders07:43 Revisiting the Founders' Goals10:34 The Reality Check15:30 The Investor's Impact15:44 The New Boss: Investors and Liabilities16:49 The Pain of Payroll: Sacrificing Founder Salaries19:10 Credit Cards and Cash Flow: Desperate Measures21:20 The Founder's Dilemma: Sacrifice and Equity23:42 The Reality of Startup Success: Rare and Elusive28:28 The Emotional Toll: Identity and Relationships31:49 Conclusion: Building a Startup That Works for You

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter explore the vital importance of maintaining a startup's foundational 'why' – the core reason for its existence. They discuss the excitement and clarity that founders experience in the early stages, the operational challenges that can cause them to lose sight of their mission over time, and practical strategies for rekindling that original passion. Through personal anecdotes and examples of companies like Apple and Google, the hosts underscore how minor compromises can erode a company's core mission. They emphasize the need for founders to continuously revisit and reinforce their original motivations to ensure sustained passion and purpose. Listeners will gain insights on recognizing when they've deviated from their vision, the benefits of realigning with the 'why', and actionable steps to recenter their focus, all while maintaining clarity and engagement within their teams.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/community/st...Websitehttps://www.startups.com/beginLinkedIn   / startups-co  Join our Network of Top Founders Wil Schroter  / wilschroter  Ryan Rutan  / ryan-rutan  What to listen for00:29 The Importance of 'Why' in Startups03:17 Losing Sight of the 'Why'05:24 Diagnosing the Loss of 'Why'09:21 The Impact of Compromises15:56 Tiny Compromises Lead to Major Changes18:48 The Slippery Slope of Compromises19:50 Losing Sight of the 'Why'20:50 Rediscovering the Purpose22:12 The Importance of Remembering the 'Why'24:30 Practical Steps to Reconnect with the 'Why'30:55 Identifying and Correcting Misalignments35:36 The Constant Battle to Maintain the 'Why'

In this episode of the Startup Therapy Podcast, Ryan and Will discuss the complex dynamics of maintaining control in a startup. They explore the misconception that not having investors means maintaining control and highlight the various ways founders inadvertently lose control—from customers, co-founders to their own staff. They delve into the idea that control is a currency spent for growth and emphasize the importance of understanding and strategically managing the areas founders are willing or unwilling to cede control over. They reveal how seemingly routine decisions can lead to significant shifts in control, urging startup founders to be proactive in understanding and negotiating these exchanges.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/community/st...Websitehttps://www.startups.com/beginLinkedIn   / startups-co  Join our Network of Top Founders Wil Schroter  / wilschroter  Ryan Rutan 

In this episode of the Startup Therapy Podcast, Ryan and Will explore the complexities of encouraging their children to become entrepreneurs. With nearly 300 episodes discussing the founder's journey, they delve into whether they'd want their kids to follow the same path. They recount personal experiences, weigh the pros and cons, and discuss the importance of allowing their children to make their own decisions. The episode emphasizes providing the tools and support to foster independent choices rather than directing them towards entrepreneurship.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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 for00:00 Introduction: The Founder's Dilemma00:55 A Proud Yet Conflicted Parent02:27 The Value of Experience05:03 Balancing Passion and Practicality08:10 Nurture vs. Nature in Entrepreneurship09:59 The Role of Education and Constraints16:21 The Reality of Entrepreneurship18:56 Reflecting on Founders' Struggles19:39 Balancing Optimism and Realism in Entrepreneurship19:59 The Timeless Nature of Startup Challenges21:31 Empathy and the Reality of Startup Therapy23:10 The Impact of Parental Influence on Career Choices25:23 Encouraging Authenticity in Children's Career Paths30:12 Empowering Kids to Make Their Own Decisions35:07 Final Thoughts on Raising Future Founders

In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Will Schroter discuss the evolving landscape of entry-level hiring for startups. They dive into why U.S. college graduates have fallen to the fourth pick for entry-level positions, overtaken by AI, global talent, and experienced young professionals who leverage new tools and platforms to gain relevant skills. They explore the benefits of each hiring option, debunk common misconceptions about global talent, and outline how these changes empower startups to make smarter, more economical hiring decisions. The discussion offers valuable insights for startup founders navigating the challenges of building efficient teams under tight budgets.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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 for00:00 Introduction: The Changing Landscape of Entry-Level Talent01:26 The Rise of AI in Startups03:48 Global Talent: A New Frontier07:30 Young and Hungry: The New Entry-Level10:19 Challenges and Opportunities for College Grads15:57 Resource Allocation in Startups24:06 Stop Guessing and Get the Answers24:16 The Global Talent Pool Advantage25:15 Quality Concerns and Misconceptions27:21 Parallel Validation in Startups32:51 The Rise of Young and Hungry Talent35:51 Evolving Job Market Expectations39:50 The Changing Landscape of Hiring45:20 Conclusion: Embrace the New Opportunities

In this episode of the Startup Therapy Podcast, Ryan and Will discuss the challenges of managing early-stage startup teams, particularly the high likelihood of turnover and the risks of handing out equity prematurely. They talk about the emotional toll of losing key team members and offer practical advice on creating vesting schedules and setting realistic expectations to safeguard against these common pitfalls. The conversation also touches on the dynamics of initial hires, the importance of flexibility, and the need to balance passion with practical considerations in team building.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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 for00:00 Introduction to Startup Challenges00:09 The Reality of Early Startup Teams01:25 Startup Weekend Insights02:38 The First Love Analogy03:44 The Commitment Dilemma04:24 Life Happens: Unplanned Disruptions12:02 The Fragility of Equity-Based Compensation13:45 Long-Term Team Dynamics15:32 Understanding the Nature of Turnover17:44 The Emotional Impact of Employee Departure18:52 The Reality of Passion and Commitment27:20 Equity Distribution and Vesting Schedules31:50 Preparing for Inevitable Change

In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Will Schroter delve into the sacrifices that come with building startup companies. They explore the dangerous ambiguity of not having specific goals and timelines, using personal anecdotes to illustrate the costly trade-offs. Will reflects on his milestone birthday and the realization that 'later' never seems to arrive, sparking a discussion about the true worth of deferred happiness and success. The conversation underscores the importance of quantifying goals and ensuring that sacrifices made today lead to genuinely rewarding outcomes. They emphasize that the journey must be carefully balanced with immediate gratification to avoid a future riddled with regret. Through vivid storytelling, they highlight the crucial lessons for founders on how to navigate the complex landscape of ambition, sacrifice, and personal fulfillment.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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 for00:21 The Danger of Vague Goals00:57 Personal Reflections on Sacrifice02:16 Quantifying Sacrifices and Rewards04:03 The Reality of Sacrifice05:27 Anecdotes of Sacrifice15:08 The Moment of Truth18:04 The Grand Experiment in Beverly Hills18:36 The Struggles of Finding a Home in LA19:07 Realizing the Cost of Living in Bel Air20:34 Questioning the Move: A Moment of Clarity23:10 The Decision to Return to Columbus23:21 Reflecting on Sacrifices and Rewards25:42 The Founder's Paradox: Happiness vs. Sacrifice28:31 The Reality of Achieving Success35:27 Balancing Sacrifice and Returns

In this episode of the Startup Therapy Podcast, Ryan Rutan and Startups.com founder Will Schroter discuss the unrealistic expectations that many startup founders have when it comes to selling their business. They detail the common pitfalls and misconceptions about startup valuation, the differences between raising capital and selling, the realities of private equity, and the dangers of deferred compensation. With insights from their own experiences of buying and selling companies, Ryan and Will provide a candid look at how to navigate the tricky world of startup acquisitions and set more realistic expectations for exit strategies.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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 for00:00 Introduction to Startup Acquisitions00:16 Realistic Expectations in Business Sales01:09 Understanding the Acquisition Process01:37 Our Acquisition Experience02:29 Challenges in Closing Deals04:31 The Importance of Direct Communication07:08 The White Knight Fallacy13:07 Investor Expectations vs. Reality20:35 The Figma Acquisition: A Case Study21:12 Understanding Market Leadership and Valuation21:44 The Reality of Acquisition Multiples24:53 The Spectrum of Potential Buyers26:07 Private Equity: The Predatory Buyer28:32 The Harsh Truths of Selling a Startup32:53 Cash vs. Deferred Compensation39:15 Managing Expectations in Startup Exits

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter discuss the often overlooked costs of ambition in the startup world. They explore how ambition, while necessary for building innovative companies, can become a debilitating force, leading to severe health issues, strained relationships, and emotional burnout. Using personal anecdotes and analogies, they emphasize the importance of recognizing the tipping point where ambition becomes more detrimental than beneficial, and advocate for a balanced approach to sustain long-term personal and professional health.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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 for00:00 Introduction to Ambition in the Startup World00:30 The Double-Edged Sword of Ambition01:27 The Escalating Costs of Ambition02:18 Ambition's Impact on Founders' Lives05:22 Personal Stories of Ambition and Sacrifice12:52 The Cultural Reward of Sacrifice16:16 Understanding Technical Debt and Burnout16:58 The Hidden Costs of Ambition17:06 Financial Struggles and Early Warning Signs18:20 Impact on Relationships20:40 Mental Well-being and Isolation23:55 The Ultimate Price: Physical Health27:12 A Rational Perspective on Work-Life Balance28:46 Final Thoughts and Advice

In this episode we discuss the current state of the startup ecosystem, which they describe as a 'silent recession.' Despite economic indicators suggesting otherwise, many startup founders are struggling with reduced capital flow and stagnating customer acquisition. The episode delves into the effects of the economic downturn on startups, the impact of investor behavior, and the historical context leading up to the current situation. Ryan and Will emphasize the importance of resetting expectations, adopting a survival mindset, and making tough decisions to ensure longevity in this challenging environment. While this period is difficult, there is always light at the end of the tunnel for those who can weather the storm.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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 For00:08 The Silent Recession in Startup Land00:38 The Reality of Founders' Struggles02:25 Economic Indicators vs. Founders' Experiences04:39 The COVID-19 Economic Magic Trick06:03 The Shift in Startup Funding Dynamics11:15 The Onset of Economic Challenges12:20 The Impact on Startup Operations16:14 VCs Halt Investments16:50 Impact on Startups17:35 IPO Implosions18:20 VCs' Strategic Pause19:56 The Domino Effect22:56 Navigating the Downturn27:39 Survival Strategies31:37 Looking Ahead33:07 Join the Startups.com Community

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroeder navigate the complexities founders face regarding success and societal scrutiny. They delve into the common critiques founders encounter about their profits and perceived entitlement while emphasizing that success should be celebrated not vilified. The conversation provides a detailed look at the multiple layers of taxation startups endure and the misconceptions surrounding founder wealth. They also highlight the emotional toll and risk involved in building a startup, offering insights into the importance of supporting founders and normalizing success.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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:00:00 Introduction to the Startup Therapy Podcast00:46 The Stigma of Founders' Success04:47 The Burden of Taxes on Founders13:55 The Lack of Support During Failure16:06 Reflecting on College Days and Financial Struggles16:25 The Reality of Startup Life17:25 Deserving Success and the Guilt Complex18:50 Comparing Founders to Other Professions21:36 The Value of Innovation and Hard Work25:36 Addressing Income Inequality and Fairness28:42 Encouraging Charitable Giving and Community Support30:12 Join the Startups.com Community

In this episode we discuss the myth of the 'bet it all' startup mentality. They highlight the importance of downside risk planning and how successful risk management plays a crucial role in startup successSign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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:00:00 Introduction to Startup Therapy00:28 The Myth of Betting It All01:36 The Reality of Downside Protection06:18 Case Study: The Zirtual Acquisition11:24 The Importance of Backup Plans18:58 Conclusion and Final Thoughts

In this episode of the Startup Therapy Podcast, we discuss the common struggles of making money in the startup world. They explore the 'noble' but flawed narrative that founders shouldn't pay themselves, why aiming too big too soon can prevent profitability, and the cycle of raising funding that often leaves founders broke.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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 For00:00 Introduction to Startup Therapy00:23 The Broken Narrative of Not Getting Paid02:35 Self-Sabotage and Going Too Big04:08 The Funding Trap05:41 The Harsh Realities of Raising Money12:07 The Never-Ending Hunger of Startups14:36 Reinvesting in Growth15:06 The Reality of Increased Liabilities15:59 The Fear of Taking Money Off the Table17:00 The Importance of Paying Yourself18:14 Balancing Profit Sharing and Salaries19:07 The Misconception of Startup Growth21:13 The Dangers of Not Taking Money Off the Table26:09 Common Sense in Startup Land27:08 Conclusion: Get Paid Now

In this episode, we discuss the potential obsolescence of venture capital due to advancements in AI technology. We explore how reduced startup costs and increased efficiency might reshape the future of funding in the startup ecosystem.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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 For00:00 Image a World Without Investors02:16 The Rise of AI and Its Impact03:01 Cost Reduction in Startups06:05 The Future of Staffing and Marketing08:37 Automation in Back Office Operations13:04 The Changing Role of Investors24:21 The Reality of VC Advice27:57 The Future of Capital Needs31:22 AI's Impact on Investment34:40 Reimagining Investment Models40:20 The Democratization of Startups

The Irreplaceable Founder. Ryan Rutan and Will Schroter discuss the irreplaceable role of founders in startups. They explore why removing a founder often leads to failure, the unique value and vision founders bring, and the difference between operational tasks and the founder's core contributions.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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 For00:00 Founder's Role in a Startup01:16 Challenges of Replacing a Founder03:04 Founder's Vision05:43 Founder's Passion07:02 Founder's Decisions09:17 The Unique Value of Founders20:06 Sales Process and Financials22:49 Management by Walking Around25:28 Risk Tolerance in Founders vs. Hired CEOs33:07 Challenges of Replacing a Founder37:54 Join the Startups.com Community

In this episode of the Startup Therapy Podcast, Ryan Rutan (CMO at Startups.com) and Wil Schroter (CEO at Startups.com) discuss the importance of saying yes to growth opportunities that startups have not previously tried. They emphasize that startups thrive by committing to new challenges, even if the path isn't immediately clear, and how this willingness to stretch can affect interactions with customers, investors, and staff. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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/

Why sometimes, less is more? Ryan Rutan and Will Schroeder discuss the misconception that reaching revenue milestones in startups will solve all problems. Explore how each milestone brings new challenges, why growing liabilities can be riskier than anticipated and the importance of balancing growth with stability.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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 For00:00 The Illusion of Milestones02:46 Scaling Challenges05:33 Weight of Responsibilities13:37 New Nodes of Problems16:21 The Reality of Scaling a Team20:05 The Myth of Effortless Wealth22:59 The Importance of Sustainable Growth26:20 The Pitfalls of Chasing High Valuations28:22 Setting Realistic Business Goals30:24 How to Enjoy Your Business

In this episode of the Startup Therapy Podcast, we discuss the inefficiencies and dangers of making decisions by committee. Why committees often fail and why founders should avoid relying on them for critical decisions. Tune in to learn why decisive, individual leadership is key to startup success.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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 For00:00 Intro01:34 The reality of committee decision-making07:06 The problem with collective accountability11:38 The downside of inclusive decision-making15:38 The myth of the best decision17:46 The importance of accountability23:04 The danger of removing consequences28:27 Leadership is about making the tough decisions

In this episode of the Startup Therapy Podcast, we talk about equity distribution in startups. Explore the psychological traps of seeking validation, the dangers of making hasty decisions when most vulnerable, and offer practical advice on how to navigate these challenges. Tune in to learn why patience and cautious decision-making are key to safeguarding the future value of your company.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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 For00:00 Intro01:00 The Vulnerability of Early-Stage Founders06:45 Evaluating Potential Co-Founders07:55 The Risk of Overpaying for Talent13:38 Milestones and Deliverables17:00 Vulnerability in Decision Making18:27 The True Cost of Equity24:09 The Fallacy of Immediate Gratification28:34 Why Wait and Evaluate

In this insightful episode of the Startup Therapy Podcast, Ryan Rutan and Wil Schroter discuss the importance of asking questions as a startup founder.Why founders often hesitate to seek advice, the untapped wealth of knowledge available? You will find tips on how to develop the muscle for asking the right questions — founders do not need to reinvent the wheel. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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/

In this episode of the Startup Therapy Podcast, Ryan Rutan and Wil Schroter, discuss the misconception that startup founders are incredibly wealthy on paper, while in reality, many struggle with personal financial stability. See the importance of paying yourself regularly, even when building a high-potential startup. Consistently getting paid, no matter how small, is crucial to long-term success and personal well-being. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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/

In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Wil Schroter talk about sacrifices founders make — accumulating debt and foregone salaries, with the expectation of being reimbursed. They discuss how founders commonly believe that future investments will pay back their personal financial commitments. They emphasize that the only real chances of getting 'paid back' are through a company sale or profit distributions. They put a light on the tough lessons learned through their own experiences and those of others in the startup world.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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/

In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Wil Schroter delve into evaluating startup team and management performance. Find out the importance of constant evaluation, highlighting the significance of both recognizing the need for improvement and taking actionable steps towards building a higher quality team.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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/

In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Wil Schroter explore the harsh reality of seeking support as a founder. Surprising, limited number of people who genuinely want to see a founder succeed. You will hear about receiving superficial praise, the impact of social media on perception, and the psychological reasons behind others' reactions to success — the envy even among those closest to the founder. Don't walk this narrow road alone, get support from your peers in founder groups at: https://www.startups.com/beginSign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: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/