Startup Therapy podcast

43:45

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 Newsletter https://www.startups.com/newsletter 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: 00:13 Exploring Founder Origin Stories 01:51 Will's Childhood Story 10:14 The Power of Agency 10:53 Teaching Kids About Agency 20:54 Personal Reflections on Agency 21:22 The Power of Agency and Optimism 22:14 Parental Protection vs. Empowerment 22:40 Real-Life Stories of Overcoming Adversity 24:40 The Magic of Agency in Hardship 26:42 Tools for Founders and Kids 27:23 Early Lessons in Entrepreneurship 34:56 The Importance of Sales Skills 42:29 Teaching Kids the Value of Agency 43:22 Join the Startups.com Community…

Startup Therapy

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Assets OVER Exits 39:42

il y a environ 10 jours39:42

39:42

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 Newsletter https://www.startups.com/newsletter 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: 00:19 The Value of Consistent Cash Flow 01:23 Examples of Profitable Local Businesses 03:37 The Misconception of Startup Exits 03:49 Real-Life Stories of Successful Small Businesses 06:16 The Broken Narrative of Startup Wealth 07:26 Reevaluating Business Success Metrics 09:05 The True Value of a Profitable Business 09:38 Calculating the Financial Impact 13:20 The Reality of Business Exits 18:09 Replacement Value vs. Exit Value 19:14 The Value of Experience and Pre-existing Solutions 19:39 Cash vs. Business Value: A Deep Dive 20:21 Real-life Examples of Business Growth 23:34 Risks and Rewards of Running a Business 27:12 The Importance of Consistent Earnings 34:54 Long-term Value and Compounding Effects…

Startup Therapy

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You Only Have to Be Right Once 32:58

il y a environ 17 jours32:58

32:58

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 Newsletter https://www.startups.com/newsletter 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 Reality of Founders' Success 02:00 Mark Cuban's Journey to Billionaire Status 06:35 The Importance of Small Wins 10:15 Financial Stability and Early Success 15:57 The Value of Consistent Small Wins 18:02 Success Doesn't Have a Timeline 18:12 When Does Success Happen? 18:20 Examples of Late Bloomers 18:45 The Myth of Early Success 19:59 The Impact of Timing 20:44 The Internet Era and Young Wealth 21:40 Outliers and Unrealistic Expectations 25:13 Consequences of Chasing Quick Success 27:28 The Value of Longevity in Business 30:02 Unexpected Success Stories 31:46 Staying in the Game 32:36 Join the Startups.com Community…

Startup Therapy

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What Would I do Differently 33:18

il y a 5 weeks33:18

33:18

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 Newsletter https://www.startups.com/newsletter 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 – Reflecting on milestones and 'what ifs' 00:44 – The risks and rewards of entrepreneurship 04:00 – A hilarious temp job experience 07:34 – The reality of alternate paths 09:02 – The danger of romanticizing 'what ifs' 13:48 – The cost of success 15:29 – Building a realistic mental model 16:18 – Stop guessing and get real answers 16:26 – The cost of staying in a job you hate 17:30 – Should you stay or leave? 18:10 – The true cost of success 19:12 – The hindsight trap: romanticizing outcomes 21:56 – Learning from failure and modeling risk 22:55 – Zirtual acquisition: a case study in risk 28:47 – Surviving failure and moving forward 31:35 – Avoiding regret and embracing risk…

Startup Therapy

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When Can I Afford to GAMBLE? 30:41

il y a 6 weeks30:41

30:41

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 Newsletter https://www.startups.com/newsletter 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: 00:15 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…

Startup Therapy

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Can Founders Find Contentment? 43:19

il y a 7 weeks43:19

43:19

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 Newsletter https://www.startups.com/newsletter 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: 00:44 Questioning the Need for a Business Coach 02:05 The Dilemma of Contentment vs. Ambition 04:02 Reflecting on Milestones and Contentment 07:35 The Nature of the Startup World 15:23 Anxiety as a Driving Force 20:51 The Anxiety of High Achievers 22:11 The Pressure of Success: Avicii and Pharrell 23:59 Imposter Syndrome Among Overachievers 26:21 The Elusive Goal of Contentment 29:08 Balancing Ambition and Contentment 33:29 The Trap of Endless Ambition 40:44 Finding True Satisfaction…

Startup Therapy

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Why do Investors FIRE Founders? 45:48

il y a 8 weeks45:48

45:48

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 Newsletter https://www.startups.com/newsletter 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 Downfall of Bench and Ian Crosby's Story 01:54 Investor Motivations and Founder Replacements 03:33 Understanding Investor Expectations 05:40 The Slow Burn of Founder Dismissal 08:23 The Impact of Replacing Founders 13:49 Personal Stories of Founder Replacement 16:47 The Challenges of Replacing Founders 19:26 Augmenting the Team vs. Replacing the Founder 22:01 Why Investors Push Founders Out 24:00 Navigating Earn-Out Periods in Acquisitions 24:26 The Challenge of Replacing Founders 26:43 Timing the Transition: Leadership vs. Management 29:08 The Mercenary CEO: Pros and Cons 35:31 Investor Expectations and Founder Realities 42:19 Handling Founder Exits Professionally…

Startup Therapy

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The Burden of Unrealistic Expectations 38:00

il y a 14 weeks38:00

38:00

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 Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/st... Website https://www.startups.com/begin LinkedIn / 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 Expectations 03:32 Investor Expectations and Their Impact 04:05 Personal Story: Missing Investor Expectations 05:44 The Reality of Investor Expectations 10:15 Comparing Yourself to Other Founders 17:45 The Peer Comparison Trap 18:06 Personal Journey: From Poverty to Success 20:01 The Futility of Social Media Comparisons 23:07 Tying Success to Self-Worth 28:20 The Illusion of Goals and Success 31:53 Reevaluating Startup Expectations 36:43 Conclusion: Building What Matters to You…

Startup Therapy

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How do I Stay Positive In Tough Times? 43:37

il y a 15 weeks43:37

43:37

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 Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/st... Website https://www.startups.com/begin LinkedIn / 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 Startups 01:01 Practical Advice for Founders in Crisis 02:10 Regaining Perspective During Tough Times 05:08 Personal Stories of Overcoming Challenges 15:29 The Importance of Taking Action 20:41 Managing Anxiety with Side Tasks 21:58 The Power of Micro Goals 23:37 Breaking Down Big Tasks 26:29 The Importance of Focus 32:07 Finding Healthy Obsessions 41:08 Building Momentum with Small Wins 43:14 Join the Startups.com Community…

Startup Therapy

1
Are Investors Trying to Push Us a Cliff? 20:06

il y a 16 weeks20:06

20:06

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 Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/st... Website https://www.startups.com/begin LinkedIn / startups-co Join our Network of Top Founders Wil Schroter / wilschroter Ryan Rutan / ryan-rutan What to listen for: 00:11 Understanding Investor Motivations 01:12 The VC Time Crunch 03:57 Profit vs. Growth: A VC Perspective 13:25 The Reality of VC Salaries 16:29 Founders vs. Investors: Different Stakes 19:00 Conclusion: Aligning Goals with Investors…

Startup Therapy

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What Previously Funded Founders Do Differently 33:21

il y a 17 weeks33:21

33:21

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 Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/st... Website https://www.startups.com/begin LinkedIn / 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 Funds 00:38 Founders' Regrets and Reflections 02:15 The Perils of Not Getting Paid 04:22 Understanding Founder Compensation 11:04 Strategies for Better Compensation 13:24 Challenges with Profitable Companies 15:02 The Pressure to Grow or Bust 15:16 The Dilemma of Raising Too Early 15:47 The Vulnerability of Early Stages 16:22 The Importance of Timing in Fundraising 16:56 The Pitfalls of Early Funding 17:28 The Distraction of Fundraising 20:34 The Impact of Investor Expectations 28:23 The Challenge of Having a New Boss 31:50 Key Takeaways and Final Thoughts…

Startup Therapy

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Are Startups Easier for Experienced Founders? 33:01

il y a 18 weeks33:01

33:01

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 Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/st... Website https://www.startups.com/begin LinkedIn / 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 Startups 01:27 The Double-Edged Sword of Experience 02:32 Drawing from Multiple Experience Buckets 05:15 Expectation Management in Startups 09:39 Avoiding Duplicate Mistakes 13:01 Raising Capital: Lessons Learned 15:16 The Value of Experience in Decision Making 17:07 The Reality of Investor Promises 17:17 Understanding People: A Founder's Key Skill 18:38 Emotional Maturity in Leadership 20:00 Challenges That Never Get Easier 21:57 The Ever-Changing Landscape of Product Market Fit 25:39 Marketing Struggles for Experienced Founders 27:40 The Pain of Failure: It Never Gets Easier 31:30 The Value of Experience and the Role of Luck 32:38 Join the Startups.com Community…

Startup Therapy

1
Who's Working for Who? 32:28

il y a 19 weeks32:28

32:28

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 Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/st... Website https://www.startups.com/begin LinkedIn / startups-co Join our Network of Top Founders Wil Schroter / wilschroter Ryan Rutan / ryan-rutan What to listen for 00:35 The Founder vs. Startup Dilemma 00:51 Political and Economic Perspectives 01:40 The Reality of Founders' Lives 03:00 The Initial Contract of Founders 05:11 The Shift in Founders' Roles 06:15 The Permanent Struggle of Founders 07:43 Revisiting the Founders' Goals 10:34 The Reality Check 15:30 The Investor's Impact 15:44 The New Boss: Investors and Liabilities 16:49 The Pain of Payroll: Sacrificing Founder Salaries 19:10 Credit Cards and Cash Flow: Desperate Measures 21:20 The Founder’s Dilemma: Sacrifice and Equity 23:42 The Reality of Startup Success: Rare and Elusive 28:28 The Emotional Toll: Identity and Relationships 31:49 Conclusion: Building a Startup That Works for You…

Startup Therapy

1
Let's Get Back to Our WHY 36:35

il y a 20 weeks36:35

36:35

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 Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/st... Website https://www.startups.com/begin LinkedIn / startups-co Join our Network of Top Founders Wil Schroter / wilschroter Ryan Rutan / ryan-rutan What to listen for 00:29 The Importance of 'Why' in Startups 03:17 Losing Sight of the 'Why' 05:24 Diagnosing the Loss of 'Why' 09:21 The Impact of Compromises 15:56 Tiny Compromises Lead to Major Changes 18:48 The Slippery Slope of Compromises 19:50 Losing Sight of the 'Why' 20:50 Rediscovering the Purpose 22:12 The Importance of Remembering the 'Why' 24:30 Practical Steps to Reconnect with the 'Why' 30:55 Identifying and Correcting Misalignments 35:36 The Constant Battle to Maintain the 'Why'…

Startup Therapy

1
How We Secretly Lose Control of Our Startups 37:28

il y a 22 weeks37:28