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 entr...
Mar 11, 2025•44 min•Ep 287•Transcript available on Metacast 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:...
Mar 03, 2025•40 min•Ep 286•Transcript available on Metacast 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-y...
Feb 24, 2025•33 min•Ep 285•Transcript available on Metacast 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/ne...
Feb 03, 2025•33 min•Ep 284•Transcript available on Metacast 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 ...
Jan 27, 2025•31 min•Ep 283•Transcript available on Metacast 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 conte...
Jan 21, 2025•43 min•Ep 282•Transcript available on Metacast 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...
Jan 14, 2025•46 min•Ep 281•Transcript available on Metacast 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 goal...
Dec 02, 2024•38 min•Ep 280•Transcript available on Metacast 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 o...
Nov 25, 2024•44 min•Ep 279•Transcript available on Metacast 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 understandi...
Nov 18, 2024•20 min•Ep 278•Transcript available on Metacast 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...
Nov 11, 2024•33 min•Ep 277•Transcript available on Metacast 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...
Nov 04, 2024•33 min•Ep 276•Transcript available on Metacast 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...
Oct 28, 2024•32 min•Ep 275•Transcript available on Metacast 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 Googl...
Oct 21, 2024•37 min•Ep 274•Transcript available on Metacast 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 o...
Oct 07, 2024•37 min•Ep 273•Transcript available on Metacast 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...
Sep 16, 2024•36 min•Ep 272•Transcript available on Metacast 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...
Sep 10, 2024•47 min•Ep 271•Transcript available on Metacast 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 fl...
Sep 02, 2024•33 min•Ep 270•Transcript available on Metacast 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 th...
Aug 26, 2024•38 min•Ep 269•Transcript available on Metacast 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 ...
Aug 19, 2024•41 min•Ep 268•Transcript available on Metacast 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...
Aug 13, 2024•32 min•Ep 267•Transcript available on Metacast 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 expectation...
Aug 05, 2024•34 min•Ep 266•Transcript available on Metacast 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 emoti...
Jul 29, 2024•31 min•Ep 265•Transcript available on Metacast 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 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 Schro...
Jul 22, 2024•22 min•Ep 264•Transcript available on Metacast 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 Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://...
Jul 15, 2024•28 min•Ep 263•Transcript available on Metacast 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 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 Net...
Jul 08, 2024•47 min•Ep 262•Transcript available on Metacast 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 Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin Link...
Jul 01, 2024•38 min•Ep 261•Transcript available on Metacast 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 Newsletter https://www.startups.com/newslett...
Jun 24, 2024•35 min•Ep 260•Transcript available on Metacast 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 Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startu...
Jun 17, 2024•31 min•Ep 259•Transcript available on Metacast 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 Newsletter https://www.startups.com/newsletter Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin Lin...
Jun 10, 2024•29 min•Ep 258•Transcript available on Metacast 
