Startup Therapy

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/

In this episode of the Startup Therapy podcast, hosts Ryan Rutan and Wil Schroter talk about the common misconception around 'working hard' within startups. They question the measurement of hard work, arguing that effort does not necessarily equate to progress or beneficial outcomes. The need for clear benchmarks within organizations to truly reward and recognize valuable contributions. Additionally, they challenge the notion of what constitutes as 'hard work' and the danger of equating all effort with success, proposing a more nuanced understanding that could lead to more effective and rewarding startup cultures.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 For00:17 The Misconception of Hard Work in Startup Culture02:49 Real Value of Hard Work in Startups04:29 The Effort vs. Progress Dilemma 06:40 Effort, Progress, and Reward10:22 Learning from Effort and Reward15:46 The Misconception of Effort vs. Outcome17:36 Setting Expectations Across Management Levels19:30 The Importance of Measurable Outcomes28:31 Setting the Right Expectations and Rewards

In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Wil Schroter discuss the evolution of startups from the emphasis on scaling and headcount to prioritizing efficiency and output, largely due to advancements in AI. The challenges of the past, such as massive payrolls, investor dependency, and expensive infrastructures highlighting the opportunities AI technologies present for startups. The conversation covers the changing landscape where small operations can achieve significant impact without the traditional costs, through examples like remote work, AI-driven efficiencies, and low-cost internet companies. They advocate for a shift in mindset where success isn't measured by headcount or office size, but by the value created with minimal resources. 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 Evolution of Startups: From Headcount to Efficiency01:29 AI and the Future of Work: A New Paradigm05:14 The Unprecedented Scale and Speed of AI Adoption07:14 AI's Impact on Staffing and Efficiency09:39 The Ethical Debate: AI and Job Creation vs. Job Displacement13:17 AI's Role in Democratizing Entrepreneurship16:00 Historical Shifts in Startup Dynamics: From Match.com to AI18:41 The Evolution of Startup Funding19:33 The Dramatic Shift in Startup Economics20:42 The Rise of Bootstrapping and Ownership Retention21:24 Case Study: Plenty of Fish's Revolutionary Approach24:32 The Future of Startup Costs and Ownership31:55 Embracing Efficiency and Impact in Startups33:48 A New Era of Startup Valuation and Efficiency

In this episode of the startup therapy podcast, Ryan Rutan and Wil Schroter delve into bootstrapping a startup. They address common misconceptions about funding, emphasizing the importance of making do with what you have and prioritizing what's truly necessary for business growth. The conversation covers practical ways to manage expenses without external funding, including strategies for hiring, marketing, and managing operational costs through discipline and creative solutions. The hosts share personal experience on how to navigate the challenges of bootstrapping, highlighting the importance of being resourceful, making money to spend money, and avoiding typical startup traps. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://groups.startups.com/Join our Network of Top Founders Check in with us on LinkedIn | Wil Schroter | Ryan Rutan00:00 Welcome to Startup Therapy00:08 The Realities of Bootstrapping01:35 Navigating the Bootstrapping Journey04:50 Mastering the Art of Compensation in Bootstrapping22:00 Innovative Marketing on a Shoestring Budget26:50 Leveraging Vendor Terms and Historical Examples28:18 The Power of Deferred Payments in Business Growth33:20 Strategic Use of Credit Cards for Business Expenses42:20 The Path to Efficient Startup Growth

In this episode of the Startup Therapy Podcast, Ryan Rutan and Wil Schroter discuss the complexities of handling feedback from investors, emphasizing the critical need for founders to properly qualify and assess the advice they receive. They highlight the dangers of acting on feedback without considering its relevance, potential bias, and the investor's qualifications. The discussion covers the spectrum of investor types, from well-meaning but inexperienced individuals to top-tier venture capitalists, and the importance of understanding the context and motivation behind their advice. You will find how to advocate for a balanced approach that involves questioning, verifying, and thoughtfully considering advice before taking action.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://groups.startups.com/Join our Network of Top Founders Check in with us on LinkedIn | Wil Schroter | Ryan Rutan

In today's Startup Therapy Podcast, Wil and Ryan talks about why earning atleast $10,000 per month is one of the most important milestones in your startup career. They stress the need to do whatever it takes to keep your business alive. Hitting this milestone gives you room to handle setbacks and shows that you're making real progress. Tune in for tips on managing startup finances and staying resilient in the ever-changing business world.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Check in with us on LinkedIn | Wil Schroter | Ryan RutanWhat to Listen For00:00 Intro01:08 The most important milestones in your business06:20 Everybody’s number is different10:27 The existential costs of both a business and its founders12:28 Do whatever it takes to reach the basic milestone16:12 Your startups should survive restarts19:50 The importance of having a backstop24:45 Maybe it’s not your year26:05 Finding value in small milestones

In today's Startup Therapy Podcast, Wil and Ryan talks about why investors choose to invest on “failed” founders. They debunk the myth that failure marks the end of a founder's journey and shows why giving people a second chance is the best investment. Tune in as they explore the investor mindset, focusing on why they prefer to invest in founders who have shown they can bounce back and learn from failure, ultimately changing how we think about startup success.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Check in with us on LinkedIn | Wil Schroter | Ryan RutanWhat to Listen For00:00 Intro01:03 Why giving people a second chance is the best investment02:29 Redefining failure04:59 “One failure doesn’t make the person a failure…”09:30 If you’re making mistakes, you’re also learning10:05 Spotlight on failure13:59 The value of experience16:49 Before the failure, there was a success20:33 Trust and familiarity in investor-founder relationships23:21 Challenge of investor decision-making27:14 Focusing on building relationships30:42 Investing in the founder’s mindset rather than ideas

In today's Startup Therapy Podcast, Wil and Ryan talks about the importance of generating revenue and being willing to do whatever it takes to move a startup forward. They discuss why it's crucial for entrepreneurs to prioritize generating income and share insights on how to overcome challenges in achieving financial sustainability. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Check in with us on LinkedIn | Wil Schroter | Ryan RutanWhat to Listen For00:00 Intro00:18 Difference between good and bad revenue01:34 Unexpected opportunities05:22 Prioritizing cash flow in the startup journey08:43 The importance of runway11:43 Focusing on startup survival 13:31 Reality of startup timelines15:00 Why surviving matters more than speed17:03 Overcoming self-imposed barriers18:53 The value of paid product discovery22:00 Learning through services24:18 Building MVPs that truly deliver value26:10 How side gigs can propel your startup forward30:36 Sacrifice and success35:13 Willingness x Hard Work = Cash

In today's Startup Therapy Podcast, Wil and Ryan talks about the hidden treasure of failed startups. From redefining valuation to creative acquisition strategies, they share insights on salvaging value from adversity. Tune in as they uncover the secrets to success amidst startup wreckage.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Check in with us on LinkedIn | Wil Schroter | Ryan RutanWhat to Listen For00:00 Intro01:42 What happens when venture-funded companies falter06:11 Rethinking asset value07:19 Recognizing when to pivot or let go09:48 Business value vs. Venture value10:52 True motivations behind exits13:26 Disconnect between opex and value15:57 Realities of startup valuation18:59 Transforming nuisance assets into opportunity21:08 Ownership and acquisition22:27 Reclaiming startup assets25:44 Startup value reset29:56 Finding value in failed startups

In today's Startup Therapy Podcast, Wil and Ryan talks about what happens if your competitor got funded. Join as they discuss the common concern of competitors securing funds and share valuable perspectives on why this might not be a cause for panic. They highlight the importance of maintaining focus, strategic planning, and turning the situation into an opportunity for your startup's success.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Check in with us on LinkedIn | Wil Schroter | Ryan RutanWhat to Listen For00:00 Intro02:20 What happens when your competitor gets funded04:15 Is fundraising all glitz and glamor?06:08 The pitfalls after getting funded10:20 Crowdfunding: Hype vs. Reality12:49 When Iivestors become your customer14:56 You now need to raise more money18:08 When focus shifts from profit to preferences25:38 The hidden costs of funding30:04 How founders see beyond competitor funding32:11 How to stay focused

In today's Startup Therapy Podcast, Wil and Ryan explore whether lacking prior experience can be a game-changer for startup founders. Having zero experience means you're new to something, and surprisingly, that can be a good thing. It brings a fresh perspective and adaptability. But for startup founders, could a lack of experience help you succeed or fail? Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Check in with us on LinkedIn | Wil Schroter | Ryan RutanWhat to Listen For00:00 Intro00:09 Is experience an asset?03:19 The bias of experience08:17 Balancing Experience and the Unknown11:45 Why not?12:50 Stop using someone else’s experience19:11 Other people’s path is not yours20:14 The best innovations are micro-innovations21:47 Be too dumb to fail26:09 Know what you know and don’t know30:02 Just knowing the basics

In today's Startup Therapy Podcast, Wil and Ryan talks about whether a founder should focus on building a startup that just makes money. Ever thought about ditching the whole fundraising craze and simply building a startup that puts money in your pocket? Join Wil and Ryan as they navigate the path less traveled, exploring the freedom and sustainability that comes with creating a startup designed to consistently generate profits. It's not just about surviving in the business jungle, it's about thriving on your terms.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Check in with us on LinkedIn | Wil Schroter | Ryan RutanWhat to Listen For00:00 Intro00:08 The end of the fundraising era04:14 Building success without venture funding07:09 Trading freedom for growth09:05 True value of incremental business growth10:14 How bootstrapped businesses create sustainable wealth14:54 Returning to the fundamental principles of business16:18 Always have a plan B19:22 Small wins add up23:32 Founders need to play defense25:58 Profits over hype

In today's Startup Therapy Podcast, Wil and Ryan discuss how you can get rockstar advisors for your startup. Discover the common mistakes people make when they are getting people to be their advisors and what are the best strategies for asking them to be your advisor. Don’t miss out and find out if your startup needs an advisor or do you just need an advice?Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Check in with us on LinkedIn | Wil Schroter | Ryan RutanWhat to Listen For00:00 Intro01:53 What is NOT an advisor03:32 Advisors don’t want to spend a lot of time with you04:59 The common mistakes people do when recruiting advisors07:06 Don’t sell your soul for a moment in time08:01 Just be willing to ask11:41 Other people don’t know your “rockstars”14:25 Possible reasons why they are advising you17:46 How to ask someone to be your advisor?24:51 The limitations to an advisor’s knowledge29:31 Advisors beyond social validation32:58 Getting an advisor is a give and get 39:31 What’s holding you back to ask?

In today's Startup Therapy Podcast, Wil and Ryan discuss whether you should get a steady paycheck or start your own startup. Choosing between a regular job and starting your own business is a big decision many face. Working a steady job offers security and a predictable income, while launching a startup is all about taking risks and creating something from scratch. Join them as they unpack the realities behind these choices, providing insights that could reshape your career perspective.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Check in with us on LinkedIn | Wil Schroter | Ryan RutanWhat to Listen For00:00 Intro00:23 Should you get a job or start a business?03:43 Age matters13:15 Soul vs. Salary20:03 How much downside can you take?22:11 Realistic probabilities of success28:10 Three types of career choices33:45 Risk, goals, and financial realities

In today's Startup Therapy Podcast, Wil and Ryan discuss the idea of managing chaos as a founder. Keeping a startup on track is like steering a ship through rough waters. Founders must stay calm and focused amid the chaos, juggling priorities and tackling problems as they arise. It's about staying cool under pressure, sorting out what matters most, and finding opportunities in the midst of the storm. Ultimately, a founder's ability to handle the daily whirlwind defines their success in the unpredictable world of entrepreneurship.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Check in with us on LinkedIn | Wil Schroter | Ryan RutanWhat to Listen For00:00 Intro00:56 How do you manage the chaos of being a founder?01:43 The first step to managing chaos is accepting chaos02:10 The problems will be endless05:06 Choose which problem to focus on10:46 Isolate the chaos into small, solvable problems13:53 The cost of lost focus in leadership15:25 Prioritization and avoiding myopic solutions21:11 Stack ranking of problems23:06 Balancing individual tasks with collective objectives25:12 Time as a problem-solving tool34:24 Create focus in chaos

In today's Startup Therapy Podcast, Wil and Ryan discuss the idea of having a co-founder. A co-founder can offer numerous benefits for a business. It allows for shared responsibilities, diverse skill sets, and a support system during challenging times. However, finding the right co-founder whose values align with yours and who complements your strengths and weaknesses is crucial for a successful partnership. In this episode, let’s find out how you can choose the right co-founder for your startup and know if you really do need one.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Check in with us on LinkedIn | Wil Schroter | Ryan RutanWhat to Listen For00:00 Intro00:36 Is it a good idea to get a co-founder?02:48 Different categories to consider when picking a co-founder05:01 ‘Who’s willing to do this?’07:30 The criteria that founders set for choosing their co-founder09:29 When you DON’T need a co-founder10:32 It’s an expensive bet11:40 Try before you buy16:50 Everybody wants the upside, nobody wants the downside21:23 Find someone committed and willing to outwork you27:03 Are your co-founders valuable?29:27 Getting involved with someone in the long term is hard

In today's Startup Therapy Podcast, Wil and Ryan discuss the concept of scaling without adding or hiring more people. Making a significant impact doesn't always mean having a large team. You can achieve remarkable results with a compact and efficient group. Instead of expanding your team, you can focus on optimizing processes and leveraging innovative tools. Let's delve into the strategies that empower a small team to make a substantial difference, proving that size isn't the only measure of success.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Check in with us on LinkedIn | Wil Schroter | Ryan RutanWhat to Listen For00:00 Intro01:23 Small Team, Big Dreams08:03 Efficiency vs. Headcount12:03 Size Creates Dysfunction13:59 The Ripple Effects of Company Growth15:27 The Myth of the 70% Employee18:22 Scaling without Headcount20:58 Cutting Back Workload Instead of Adding People25:01 Building Impactful Products with Minimal Staff

In today's Startup Therapy Podcast, Wil and Ryan discuss about the grind and guilt dilemma of founders. Founders often struggle with the never-ending hard work of growing their business, driven by their passion and ambition. This can create a persistent feeling of guilt as they try to juggle work demands with their personal life and health. So how can you achieve a harmonious equilibrium that allows you to pursue your entrepreneurial dreams while also nurturing your mental and physical health and maintaining meaningful relationships?Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Check in with us on LinkedIn | Wil Schroter | Ryan RutanWhat to Listen For00:00 Intro00:08 Guilt out of fear04:31 The fear of failing as a founder08:57 Pride, guilt, and the struggle with asking for help10:15 Entrepreneurship as a way out13:29 Fear as a superpower16:18 When guilt compounds…18:31 The nobility in hard work20:22 When work defines comfort22:39 More money, more problems25:08 Passion and pressure28:45 Fear and greed in later life31:06 Escaping the grip of work addiction36:58 Self-imposed workaholism