Startup Therapy

Startups.com
Startup Therapy

The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.

  1. FEB 3

    What Would I do Differently

    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/newsletter Resources:Startup Therapy Podcast https://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/ What to listen for: 00:07 – 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

    33 min
  2. JAN 27

    When Can I Afford to GAMBLE?

    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/newsletter 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:00:15 Why Taking Risks Is a Luxury 02:08 Balancing Personal and Business Costs 03:44 Lessons from Startups.com 05:55 Why You Need a Risk Buffer 10:25 Figuring Out the Minimum Viable Risk Pool 16:51 Financial Discipline and Budgeting 19:09 The Freedom Fund Explained 26:51 How to Survive Financial Challenges

    31 min
  3. JAN 21

    Can Founders Find Contentment?

    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/newsletter 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 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

    43 min
  4. JAN 14

    Why do Investors FIRE Founders?

    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/newsletter 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: 00:25 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

    46 min
  5. 12/02/2024

    The Burden of Unrealistic Expectations

    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/newsletter Resources: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

    38 min
  6. 11/25/2024

    How do I Stay Positive In Tough Times?

    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/newsletter Resources: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

    44 min
  7. 11/11/2024

    What Previously Funded Founders Do Differently

    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/newsletter Resources: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

    33 min
4.9
out of 5
125 Ratings

About

The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.

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