Startup Therapy

ตอน

• The Most Expensive Equity Doesn't go to Investors 01.06.2026 46นาที

  Why do founders fight over giving an investor 15% but hand out huge chunks to co-founders, employees, and advisors with far less certainty of return? The episode argues that investor dilution is often the cleanest trade because cash and terms are clear, while “everyone else pays in maybes and promises.” It warns that early-stage equity feels worthless but represents 100% of a company’s future value, so giving away 50% to a near-stranger can become a permanent cap table problem that also costs speed, optionality, and sanity. Practical fixes include vesting, cliffs, tying equity to real value creation, defining what happens if someone stops contributing, and putting breakup terms in writing early. The discussion also critiques employee equity as time-based rather than performance-based, and advisor equity as often unaccountable, where tiny percentages can hide very expensive outcomes.What to listen for:00:00 Investor vs Founder Equity01:26 Equity Is Priceless03:43 Co-Founder Split Hangover06:04 Why People Underperform11:15 Fairness Turns To Resentment12:44 Will's Unsubscribe Story15:53 Vesting And Breakup Terms18:17 Early Employees Option Pool20:26 Equity As Compensation Trade21:59 Paying Twice With Equity22:14 Does Equity Change Effort23:10 Lottery Ticket Reality27:23 Equity Rewards Three Things27:37 Advisor Equity Math31:00 Reputation Versus Contribution33:30 Network Intros Social Capital35:56 Advice Has Shelf Life40:24 Pricing Advisor Time44:06 Treat Shares Like CashResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/
• How to be Great at Worrying 25.05.2026 35นาที

  Ever wake up at 3:00 AM convinced your startup is about to break? The conversation unpacks how founders can’t really “leave work,” and how constant vigilance can turn into fear dressed up as responsibility—endless rumination that produces stress, not decisions. Will shares decades of 3:00 AM worry cycles, the superstition that anxiety prevents disaster, and how even vacations get hijacked by disaster simulations (including getting hacked on the way to Comic-Con). They draw a line between real thinking that creates options and looping that creates suffering, then discuss practical replacements: box breathing to fall back asleep, gratitude to reset perspective, and self-talk that puts the “experienced founder” back in charge. The goal isn’t to stop worrying, but to channel that energy into small, solvable actions instead of spirals.What to listen for:00:41 Learning to Worry01:21 Walk the Lot Mindset03:28 Fear as Responsibility05:07 Paranoia and 3AM Ceilings06:25 Anxiety Superstition Loop08:18 Vacation Disaster Mode10:21 Thinking vs Rumination13:10 Breathwork Replacement14:14 Milestones Won't Fix It15:53 Experience Adds Knives18:47 Fear Makes It Worse19:39 Worry As Energy21:24 Productive Distractions22:29 Finish Small Tasks23:39 Save It For Morning27:17 Worry Versus Solving31:13 One Pebble At A Time34:59 Make Worry A SuperpowerResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/
• Can Startups Be a Team of One? 18.05.2026 43นาที

  What happens if building a startup no longer requires a team? The conversation explores how AI is rapidly turning the classic “product + developer + marketer” founding trio into an optional choice, making one-person companies the new default as tools get dramatically better and far cheaper than hiring. They unpack how this shift changes equity, speed, and the quality filter that co-founders and teams used to provide, while also threatening many “on-ramp” roles like customer support and other knowledge-based services (accounting, payroll, legal). They wrestle with the economics that push founders toward AI, the competitive pressure that makes it feel unavoidable, and the human costs—loneliness, loss of pushback, and erosion of culture. Ultimately, they argue that hiring humans may become a luxury reserved for uniquely human value: creativity, leadership, intuition, and genuine connection.What to listen for:01:04 Inside View of Founders02:38 Economics Meets Capability03:01 Generational Shift in Startups05:58 From Co-Founders to AI09:09 Equity as Quality Filter10:44 Humans Optional Now12:04 One Person Startup Math14:23 Moats Erode Overnight15:32 Jobs First to Disappear18:14 Disruption and New Demand19:59 Next Roles on the Chopping Block21:00 Gatekept Knowledge Flips22:01 AI Becomes Hygiene23:45 Where Humans Matter24:33 Pushback And Refinement28:33 Loneliness Rubber Band30:36 Humans As Luxury34:20 Hiring Math Breaks39:02 Culture Versus CostResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/
• Why are we Really Building a Startup 11.05.2026 33นาที

  What are you really trying to fix by building this company—and what happens when you finally admit it? The conversation unpacks how founders often default to a public “change the world” story while their private motive is something more personal like safety, control, validation, belonging, autonomy, or even revenge. When that real why stays hidden, decisions get miscalibrated and founders chase the hardest possible path (like massive VC rounds) even when a smaller outcome might satisfy the true need. They discuss how these motives “leak out,” especially after selling a company and realizing you’re no longer needed, and why success (even IPO-level) rarely erases old wounds. The key is naming the motive, right-sizing the plan to it (“minimum viable ego”), and building a deliberate version of success that fits what you’re actually optimizing for.00:00 Founders Lie to Themselves01:53 Public Why vs Private Motive02:58 Freudian Roots of Drive03:37 Will’s Safety and Control Story07:11 When the Why Leaks Out07:35 Selling and Not Being Needed09:57 Validation as True North12:01 Ryan’s North Star Revealed13:45 Will’s Revenge and Proving16:07 Steve Jobs Still Hurt17:57 Haters And Criticism18:44 Minimum Viable Ego19:29 Different Success Thresholds20:47 Stop Trying To Prove Them21:22 Pick The Right Vehicle22:05 The Villain You Invent23:45 Success Doesnt Fix You29:17 Money And Marriage Myths30:25 Alignment Over Ego Death31:03 Autonomy As The Real Goal32:34 Own Your MotivationResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/
• We Rarely "Control" Our Startups 13.04.2026 46นาที

  Worried about “losing control” because of dilution? This episode breaks down why equity is a poor proxy for control in startups: the cap table splits money, while control is defined by decision rights in the operating agreement and enforced through board voting. The hosts explain how founders can own most of the company yet still need permission for key actions (like senior hires), how boards are built (often 2 founders, 2 investors, 1 independent), and how board math can outweigh founder ownership—especially when things go wrong. They also cover how operating agreements get rewritten each funding round, how founders can be fired even if they own a majority, and why investors can control outcomes through financial leverage when runway is low. The core advice: define non-negotiables early, focus on governance and runway, and stay funded and credible.What to listen for:00:00 Control Is Not Equity00:29 Investor Leverage Wake Up Call02:53 What Founders Mean By Control04:08 Co Founder Control Myth07:47 Operating Agreement Rules10:57 Protective Provisions Explained14:48 You Can Be Fired19:07 Boards And Governance21:47 How Funding Changes Control24:13 Board Coup Reality24:42 Board Math Wins25:25 Voting vs Ownership26:32 Operating Agreement Changes28:52 Cash Leverage Control32:27 Credibility and Sentiment35:46 Founder Nonnegotiables40:43 Change of Control Rights44:00 Exit and Liquidity Traps45:19 Governance Over EquityResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/
• Founders Need Finish Lines 06.04.2026 38นาที

  Ever feel like you hit a milestone in your startup and immediately get handed the next problem? The episode explores why startup work rarely delivers a true sense of “done,” how founders get trapped by the arrival fallacy (believing the next round, milestone, or cushion will finally bring relief), and how the constant threat of being “eaten” by faster competitors turns ambition into paranoia. Ryan and Will compare the endless nature of startups to more finite work, discuss how chasing metrics and despising complacency fuels chronic restlessness, and share personal examples of goals that didn’t bring fulfillment. Their takeaway: startups are an infinite game, so founders need to create completion outside work—through finishable, tangible activities like cooking, workouts, sports, cleaning, or building projects—because completion is psychological maintenance, not a luxury.What to listen for:01:37 Goals vs Fulfillment02:46 Arrival Fallacy Explained03:42 Milestones Aren't Meaning05:16 Dopamine and Restlessness05:40 Painful Arrivals Stories09:13 Despising Complacency11:00 Getting Eaten Alive by Change16:09 Contentment vs Career Metrics18:24 Ad Break and Lamborghini Setup19:22 Breaking Down The Fees19:40 Paranoia About Losing It20:30 Advice Comes With Bias21:08 Founder Scarcity Mindset22:54 Finding Completion Offline26:32 Why Startup Wins Feel Empty31:41 Small Finishes Refill The Tank33:16 Buying Stuff Won’t Fix It35:57 Appreciation Versus Earning37:34 Manufacture Your Finish LineResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/
• What Should My Expectations Be? 23.03.2026 47นาที

  Ever feel like you’re working nonstop and still falling behind? The discussion argues founder happiness and decision-making improve fastest by recalibrating expectations, because “happiness = reality ÷ expectations.” Using stories from trading work for pizza or restaurant tabs to later winning massive business, it highlights how low expectations can make progress feel rewarding, while the “snowflake myth” and unpriced optimism create entitlement and disappointment. They distinguish aspiration (what you’d like) from expectation (what must happen), urging founders to replace unicorn fantasies with concrete, earned milestones like revenue, payroll, and product-market fit. They stress startups take far longer than most timelines claim—often 5–10+ years—even for legendary companies, and warn that funding timelines and social comparison can trigger panic and bad decisions.00:37 Pizza Paper Hustle01:41 Rib Money Origins03:07 From Ribs to Lilly04:30 Happiness Math Formula05:59 Lambo Expectations Check07:47 The Snowflake Myth08:09 Optimism vs Expectation09:19 IPO Odds Reality10:53 Aspiration Not Debt12:07 Milestones Over Unicorns15:06 Time Myths and 3x Rule17:36 Funding Clocks and Panic20:42 Startup Mythology Trap24:08 Five to Ten Year Truth24:38 Overnight Success Myth25:19 Funding Timeline Trap26:01 Check Your Premises26:54 Entitlement Mindset28:19 Effort Versus Results30:05 Earning Versus Inheriting35:51 Milestones Not Home Runs37:57 Small Wins Ladder41:06 Expectations And ComparisonResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/
• What Actually Happens When A Founder Runs Out of Gas? 02.03.2026 34นาที

  What do you think really happens if you burn out and step away for a minute? The conversation breaks down how founders often imagine an apocalyptic chain reaction—customers leaving, the team collapsing, investors panicking—when in reality burnout is a predictable capacity ceiling and most worst-case scenarios don’t happen. They argue the real danger is pretending burnout won’t come, pushing until physical failure, and keeping recovery secret, which can create the chaos founders fear. Using sports analogies, they emphasize that staying “on the field” nonstop makes you a liability, and that planned breaks build resilience, give teams room to step up, and help founders regain creativity and effectiveness. The core takeaway: treat recovery like required maintenance, plan for it, and build a company that doesn’t depend on you 24/7.What to listen for:00:57 Apocalypse Scenario02:12 Always On Mentality03:49 No Built In Breaks06:56 Superman Plan Fails08:06 Burnout Warning Signs10:32 Atlas Shrugged Reality15:22 Hockey Shift Lesson16:23 Fear of Replacing Yourself16:46 Stop Guessing Get Help17:19 Burnout Nightmare Myths19:14 When Investors Shrug20:57 Youre Not The Main Character23:24 Let The Team Step Up25:14 Breaks Prevent The Crash27:06 Vacation ROI Mindset29:34 Plan Recovery Like Taxes31:44 Durable Not Tireless33:22 No Great Company Empty TankResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/
• The Value of Distraction 23.02.2026 35นาที

  What if the thing that looks like a distraction is actually the move that saves your startup? This episode breaks down why the “stay focused at all costs” advice can be risky when you’re still figuring out what actually works. The hosts challenge the myth of the linear startup path, arguing that side quests—small, intentional experiments with capped downside—create learning, reduce single points of failure, and help you earn the right to pivot with evidence instead of vibes.They share how Fundable’s early equity crowdfunding push revealed founders were unprepared to raise money, which led to a major side quest: doing diligence on about 100 companies, talking to 200+, and acquiring six venture-backed businesses—work that became the genesis of startups.com. Along the way, they highlight the value of the quest itself (market intel, understanding what not to do, faster learning) and even mention an extreme near-distraction: briefly considering buying Atari.The conversation also reframes common “side quests” like doing services work while building a product, arguing that bringing in revenue to stay alive isn’t a distraction—it’s the business. They clarify the difference between a side quest (exploration) and a pivot (committing to a new direction), and point to the podcast itself as an example of a side quest that became a major long-term asset after a rough start.What to listen for:00:40 The AI Newsletter Moment That Sparked the Topic01:47 What a “Side Quest” Means for Founders03:45 The Myth of the Linear Startup Path06:34 When Focus Becomes a Liability: Certainty, Ego & Roadmaps10:04 Side Quests as the Ongoing Lab (and Why It Never Ends)12:01 Case Study: Fundable 2012 and the Crowdfunding Gold Rush15:48 The Pivot: Founders Needed Help, Not Just a Platform18:07 Side Quests Done Right: Controlled Experiments (…and Almost Buying Atari)18:42 The Wild Idea: Almost Buying Atari (Nostalgia vs. Distraction)19:48 Why Side Quests Matter: Learning More Than the Outcome20:42 Founder-Forward Deal Talks & Market Intel as a Force Multiplier22:10 Side Quests as “Insurance”: Selling the Learning to Skeptics23:48 The Classic Startup Side Quest: Services to Pay the Bills27:14 Side Quest vs. Pivot: Exploration First, Commitment Later27:52 The Podcast as a Side Quest That Became Core to the Business30:26 Earning the Right to Pivot: Evidence, Courage, and Finding Truth34:20 Closing: De-Risking Through Exploration + Startups.com Community InviteResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/
• Master Failure 16.02.2026 36นาที

  What if failure isn’t something to avoid, but a skill to master? This episode breaks down why startups can’t be built on certainty—new markets, new products, and new teams mean you’re guaranteed to be wrong a lot. The goal isn’t to “be right,” it’s rapid error correction: make decisions, ship anyway, learn fast, and recover even faster. The conversation covers how avoiding failure leads to paralysis (“steering a parked car”), why indecision compounds in startups, and how to reduce risk by keeping failures small, reversible, and frequent (kill switches, stop rules, and capped losses). They share early personal stories—school fights and a childhood cattle business collapse—to show how overcoming real consequences builds confidence and resilience. Practical examples include choosing an ICP quickly, improving poor conversion rates through iteration, using vesting/cliffs when picking co-founders, and why even top VCs still miss constantly. The key takeaway: the most dangerous competitor is the one who isn’t afraid to get hit, recover, and keep coming back—because that’s as close to “invincible” as a founder can get.What to listen for:02:01 Failure Isn’t the Enemy: Stop Optimizing for Being Right02:59 The Founder Reality: Uncertainty, Rapid Error Correction & the Boxing Analogy03:44 Safety vs Startups: Why Most People Avoid the Risk05:24 ‘Steering a Parked Car’: Indecision Kills Startups07:54 Make the Call, Learn Fast: Small Failures, Big Truths09:02 We’re Conditioned to Fear Failure (School, Work, Relationships)11:59 Will’s Origin Story: Jason Barker and Learning to Beat the Monster14:48 Choosing to Fail on Purpose: Turning Fear into a Superpower17:06 Ryan’s First Big Failure: The Farm/Cattle Business Lesson Begins17:45 Cash-Strapped Expansion: Inventory Leverage & a Brutal Winter18:09 When the Side Hustle Needs a Side Hustle (and the Cost of Neglect)18:35 Failing Hard at 12: Losing Animals and Learning to Plan19:51 Founders Don’t Win by Being Right—They Win by Taking Hits21:36 Shipping While Wrong: Marketing Experiments, MVPs, and Momentum22:51 Hiring, Co-Founders & Investors: Why Nobody Can Pick Perfectly24:00 The Real Skill: Recovering From Failure (Resilience as a Reflex)30:26 Small Blast Radius, High Frequency: Reversible Bets & Kill Switches31:13 Failure Is Portable: Building a House, Living ‘Why Not,’ No RegretsResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/
• We Can't Predict the Future Anymore 09.02.2026 37นาที

  Is AI truly the game-changer for startups, or does it bring unexpected chaos? This episode dives into how AI is transforming forecasting, marketing, product development, employment, and investment in the startup ecosystem. Ryan Rutan and Will Schroter discuss the rapid pace of change brought by AI, including the exciting opportunities and the unsettling uncertainties. They explore how traditional pillars of business like hiring, marketing, and customer acquisition are being upended, creating both new challenges and avenues for innovative founders to thrive. Tune in to understand how to navigate this AI-driven landscape and leverage the chaos for maximum impact.Resources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:00 Introduction and Future Predictions00:49 The Impact of AI on Business Models02:06 AI's Rapid Advancement and Market Disruption04:17 Challenges in Marketing and Content Creation10:04 Hiring and Talent Management in the AI Era15:18 Product Development and Market Relevance17:04 Industries Vanishing Overnight17:32 The Accelerating Pace of Change18:20 Investment in the Age of AI19:07 The Future of Startup Funding22:31 The Shrinking Moat of AI24:54 Compounding Anxiety in the Startup Ecosystem33:37 Founders: Built for Chaos35:53 Embracing the Problem Business
• We wanted efficiency. We got isolation. 02.02.2026 41นาที

  How has the relentless pursuit of efficiency, aided by tools like remote work, Zoom, Slack, and AI, affected our human connections? In this episode, we're exploring the cost of optimized workflows on our humanity. We delve into personal anecdotes and discuss the ramifications of isolation in the workplace and the loss of shared experiences. We also contemplate the importance of reintroducing human interactions to ensure a balanced, connected, and more fulfilled work environment.Resources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:31 The Loneliness of Optimized Efficiency01:48 The Impact of Remote Work on Human Connection04:14 The Rise of AI and the Decline of Human Interaction12:41 The Evolution of Remote Work Culture17:20 The Dystopian Reality of AI Conversations20:22 The Importance of Laughter and Human Interaction21:23 Leveraging GPT for Problem Solving22:18 The Downside of Relying on AI23:45 The Value of Human Interaction in the Workplace25:09 The Impact of AI on Team Dynamics27:04 Balancing Efficiency and Human Connection29:05 The Future of Startups and Human Connection30:33 The Need for Human-Centric Work Cultures32:06 Conclusion: Embracing Humanity in the Age of AI
• Are startups the future of employment? 03.12.2025 47นาที

  What will AI do to everything? In this episode, we explore how AI is set to create a surge in new startups, reshaping employment as we know it. As jobs get displaced, the concept of big employment shifts, giving rise to smaller, more agile companies using AI tools. Drawing parallels with past technological revolutions, we highlight the opportunities that lower costs and new market demands present for founders. We discuss the transformation in various sectors, from customer service to content creation, and emphasize how AI can democratize entrepreneurship globally. Finally, we delve into the exciting potential for startup growth and the role of AI as both a tool and a transformative force in the startup ecosystem.Resources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:24 The Impact of AI on Employment01:16 Historical Parallels: Internet and Industrial Revolution02:32 The Shift from Big Employment to Entrepreneurship03:16 The Decline of Traditional Jobs05:25 Opportunities in the New Economy11:48 The Rise of the Creator Economy20:15 Macro Trends and Future Outlook23:52 The Rise of Billion-Dollar Startups24:24 Price Collapse and Premium Experiences26:01 The Impact of AI on Startups26:44 The Creator Economy and Niche Markets29:06 The Evolution of eSports31:09 The Dawn of Young CEOs33:22 The Future of Entrepreneurship39:43 Global Entrepreneurship and Accessibility45:56 The Age of the Startup
• The Founder Hard Reset 25.11.2025 25นาที

  Ever felt like vacations just aren't cutting it when it comes to startup burnout? In this episode, Ryan Rutan and Will Schroter dive deep into why burnout is inevitable for founders and how quick fixes like vacations often fail to address the root of the issue. They explore how to truly recover and maintain that all-important spark in your work. Learn why it's crucial to inventory what drains and fuels your energy, and how making meaningful changes—not just taking time off—can lead to sustainable recovery. Real-life examples and practical advice make this a must-listen for any founder feeling the grind.Resources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:34 The Misconception of Business Success and Burnout01:00 Personal Stories of Burnout02:10 The Ineffectiveness of Vacations03:49 The Importance of Meaning in Work04:11 Personal Struggles with Burnout07:27 The Real Cause of Burnout10:23 Balancing Tasks to Prevent Burnout11:59 The Battle Within: Struggles in the Workplace12:58 Startup Expectations vs. Reality13:46 Finding Energy and Avoiding Burnout15:34 The Importance of Positive Energy18:22 Active Breaks for Founders22:32 Identifying and Addressing Burnout25:31 Join the Startups.com Community
• Is there a line between Founder optimism and delusion? 17.11.2025 37นาที

  Can founders turn delusion into success? In this episode, Ryan and Will discuss the essential role of optimism in startups. Drawing parallels between founders and firefighters, the duo explores how belief against all odds drives entrepreneurs forward. They explain how maintaining optimism is not just about having a positive outlook but about creating momentum from minor wins and leveraging chaos as an opportunity. The hosts also address the fine line between optimism and dishonesty, emphasizing the importance of an 'educated wish.' Whether you're battling to raise funds or struggling to maintain morale, this episode delves into why a founder’s unyielding belief is crucial for startup survival and growth.Resources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:07 The Delusional Optimism of Founders01:02 Creating and Living in a Fantasy02:00 Running Toward Chaos04:54 The Passion and Drive of Founders05:59 The Reality of Startup Life12:08 The Role of Belief and Proof14:31 Finding Optimism in Small Wins16:40 Persistence in the Face of Rejection18:56 The Power of Hope in Business19:52 The Role of Optimism in Startups21:41 Balancing Optimism and Honesty23:03 The Fine Line Between Optimism and Deception26:07 The Importance of Optimism in Leadership28:55 The Role of Optimism in Overcoming Challenges32:05 The Founder's Mindset: Manufacturing Optimism
• Prioritize Productivity Over Popularity 07.11.2025 31นาที

  Ever find yourself caught in the trap of confusing visibility with progress? In this episode, we'll delve into why seeking attention can often feel like momentum but doesn't necessarily translate to business traction. Will Schroter shares a cautionary tale from his own experience, revealing how his focus on brand-building and networking kept him from truly building his company. We explore the fine line between personal branding and productivity, and why many founders need to prioritize the latter to achieve real success. It's a reminder that until your product and business are fully developed, every external interaction could be costing you more than it's worth.00:30 The Trap of Visibility: A Personal Story02:24 The Illusion of Popularity vs. Productivity06:21 The Modern-Day Equivalent: Social Media09:24 Balancing Publicity and Productivity11:23 Cautionary Tales and Lessons Learned12:55 The Importance of Focus and Balance14:48 Earning the Right to Brand Build15:29 The Pitfalls of Prioritizing Popularity Over Business16:07 The Honeymoon Period of Venture Funding17:40 The Dangers of Personal Branding for Founders18:47 When Personal Views Hurt Business21:39 Balancing Personal and Company Brand23:48 Focus on Building the Business First30:22 The Cost of External InteractionsResources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:
• Better is Better than Bigger 27.10.2025 35นาที

  Is getting bigger always better for startups? This episode dives into the hidden costs of scaling up and how growth can sometimes make a company worse, not better. Ryan and Will discuss the trade-offs between size and quality, using examples like Google and PayPal. They explore how rapid growth can diminish company culture, slow down decision-making, and introduce inefficiencies. The conversation also covers personal experiences in startup growth, emphasizing the importance of optimizing for better rather than just bigger. Whether it's adding more staff or raising capital, they advocate for making decisions that enhance company quality and founder life satisfaction.Resources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:14 The Myth of Bigger is Better00:43 Examples of Companies That Grew and Suffered02:00 The Hidden Costs of Scaling05:08 Personal Experiences with Growth Challenges13:01 The Importance of Freedom and Quality17:18 The Hidden Costs of Growth17:58 Balancing Growth and Quality of Life20:39 Defining Non-Negotiables for Better Business22:33 Scaling with Soul: Maintaining Company Culture24:41 Quality Over Quantity: Making Strategic Decisions28:07 The Power of Saying No31:15 Sticking to Your Values for Sustainable Growth
• Founder Authenticity: Use with Caution 22.10.2025 31นาที

  Ever wonder if being your authentic self at work might sometimes do more harm than good? The delicate balance of authenticity and diplomacy in leadership. From discussing the rare contexts where pure honesty works, to sharing personal anecdotes about navigating the consequences of unfiltered truth, this episode unpacks how transparency can impact your team, brand, and personal relationships. Find out why being your true self might only be great advice 6% of the time and how effective communication can save you from unintended fallout.Resources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:01:01 The Consequences of Unfiltered Honesty01:26 Generational Differences in Professionalism02:44 The Power Dynamics of Founders04:45 Balancing Honesty and Diplomacy06:01 The Luxury of Honesty and Risk08:04 The Importance of Filtering Communication12:56 The Duality of Professional Personas15:21 The Consequences of Honesty in Leadership16:19 Balancing Honesty and Diplomacy17:10 The Importance of Empathy in Communication18:26 The Cost of Unfiltered Honesty19:51 Frameworks for Effective Communication20:55 Lessons from the Terminator: Choosing Responses Wisely22:07 The Role of Diplomacy in Leadership28:17 The Medium Matters: Hot, Warm, and Cold Communication29:56 Prioritizing Outcomes Over Authenticity
• Founders, Embrace Your Flaws 14.10.2025 41นาที

  Are you convinced that you need to fix all your flaws as a founder? In this episode, we explore why that's not necessarily true. Ryan and Will dive deep into the idea that both startups and their founders are loaded with problems, some of which aren't really 'problems' at all but hidden superpowers. From obsessive tendencies to ADHD, they discuss how to harness these traits for success rather than trying to fix them. Drawing from personal experiences and industry insights, they touch on the influence of pharmaceutical marketing, the role of social media in shaping perceptions, and the importance of finding context for your strengths. This episode challenges you to rethink how you view your weaknesses and offers a fresh perspective on founder self-acceptance and leveraging inherent traits for entrepreneurial success.Resources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:33 Founders and Their Problems01:15 Pharmaceutical Industry Insights02:36 Social Media and Problem Creation03:46 Personal Struggles of Founders05:07 Overthinking and Control Issues11:15 ADHD and Academic Challenges17:11 Harnessing Obsessiveness for Success20:40 Evaluating Self-Help Advice21:09 Struggles with Attention Span21:31 Learning Outside Traditional Education22:15 Emphasizing Strengths Over Weaknesses23:29 Founders and Their Strengths28:08 Anxiety as a Superpower34:46 The Importance of Context in Learning38:36 Self-Acceptance and Utilizing Strengths
• Is Remote Culture, Actually Culture? 06.10.2025 38นาที

  Have you ever wondered if remote work is better than being in the office? Ryan and Will dive into their experiences and how their work culture has evolved over 20 years. They discuss the pros and cons of remote work, the importance of autonomy, and how remote setups have stripped away some of the overhead, revealing who truly thrives in this environment. They also explore whether it's possible to create a strong company culture remotely and how the shift has amplified the best and worst in employees. Tune in as they break down their journey from being die-hard office goers to embracing the flexibility and autonomy of remote work.Resources:Startup Therapy Podcasthttps://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedInhttps://www.linkedin.com/company/startups-co/Join our Network of Top FoundersWil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:36 The Shift from Office to Remote Work01:01 Challenges of Remote Work01:57 Socialization and Remote Work04:42 Remote Work Rituals and Failures07:26 Digital Culture and Transactional Work12:06 Evolving Company Culture19:14 The Evolution of Workplace Culture19:34 Starting Fresh: Can We Be Transactional?20:20 The New Culture: Autonomy and Responsibility21:37 Balancing Work and Personal Life23:49 The Value and Challenges of Remote Culture25:34 Autonomy: The Ultimate Compensation26:10 Remote Work: Amplifying Strengths and Weaknesses32:13 The Social Aspect of Work37:22 The Future of Work: Remote vs. In-Office