How to be Great at Worrying

The Right Time to Start is Right Now

Ever feel like you’re “almost ready” to launch—just one more feature, plan, or credential away? This episode argues that “ready” isn’t a prerequisite for startups; it’s the result of starting and getting real market feedback. Using examples like selling early software for $1,500, learning web building on the fly, a disastrous (but educational) client pitch moment, and even an impulsive scuba dive, the discussion shows why planning can become productive-looking theater when nothing is being tested. The real cost of waiting isn’t just lost time—it’s lost learning, missed customers, and negative compounding versus competitors who take action. Planning has value only when it directly leads to action, because failure and iteration are the mechanism that reveals what works. What to listen for: 01:14 Plans Meet Reality 02:00 Readiness Comes After 02:34 First Founder Breakthrough 07:41 Micro Center Origin Story 10:07 Cost of Waiting 11:14 Planning Versus Theater 12:23 Test With Customers 14:09 Ecommerce Pitch Fail 16:41 Whiteboard Versus Field 18:48 Learning By Building 19:35 Learn By Doing 20:05 Founder Skill Stack 20:45 Econ 101 Mindset Shift 22:45 Human Potential Unlocks 24:27 Momentum Beats Certainty 25:58 Plan To Learn Fast 30:26 Conditioned To Avoid Failure 34:34 Cost Of Waiting 35:50 Action Over Perfection 36:47 Stop Waiting Start Now Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin LinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroter https://www.linkedin.com/in/wilschroter/ Ryan Rutan https://www.linkedin.com/in/ryan-rutan/

The Most Expensive Equity Doesn't go to Investors

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 Equity 01:26 Equity Is Priceless 03:43 Co-Founder Split Hangover 06:04 Why People Underperform 11:15 Fairness Turns To Resentment 12:44 Will's Unsubscribe Story 15:53 Vesting And Breakup Terms 18:17 Early Employees Option Pool 20:26 Equity As Compensation Trade 21:59 Paying Twice With Equity 22:14 Does Equity Change Effort 23:10 Lottery Ticket Reality 27:23 Equity Rewards Three Things 27:37 Advisor Equity Math 31:00 Reputation Versus Contribution 33:30 Network Intros Social Capital 35:56 Advice Has Shelf Life 40:24 Pricing Advisor Time 44:06 Treat Shares Like Cash Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin LinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroter https://www.linkedin.com/in/wilschroter/ Ryan Rutan https://www.linkedin.com/in/ryan-rutan/

How to be Great at Worrying

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 Worry 01:21 Walk the Lot Mindset 03:28 Fear as Responsibility 05:07 Paranoia and 3AM Ceilings 06:25 Anxiety Superstition Loop 08:18 Vacation Disaster Mode 10:21 Thinking vs Rumination 13:10 Breathwork Replacement 14:14 Milestones Won't Fix It 15:53 Experience Adds Knives 18:47 Fear Makes It Worse 19:39 Worry As Energy 21:24 Productive Distractions 22:29 Finish Small Tasks 23:39 Save It For Morning 27:17 Worry Versus Solving 31:13 One Pebble At A Time 34:59 Make Worry A Superpower Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin LinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroter https://www.linkedin.com/in/wilschroter/ Ryan Rutan https://www.linkedin.com/in/ryan-rutan/

Can Startups Be a Team of One?

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 Founders 02:38 Economics Meets Capability 03:01 Generational Shift in Startups 05:58 From Co-Founders to AI 09:09 Equity as Quality Filter 10:44 Humans Optional Now 12:04 One Person Startup Math 14:23 Moats Erode Overnight 15:32 Jobs First to Disappear 18:14 Disruption and New Demand 19:59 Next Roles on the Chopping Block 21:00 Gatekept Knowledge Flips 22:01 AI Becomes Hygiene 23:45 Where Humans Matter 24:33 Pushback And Refinement 28:33 Loneliness Rubber Band 30:36 Humans As Luxury 34:20 Hiring Math Breaks 39:02 Culture Versus Cost Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin LinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroter https://www.linkedin.com/in/wilschroter/ Ryan Rutan https://www.linkedin.com/in/ryan-rutan/

Why are we Really Building a Startup

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 Themselves 01:53 Public Why vs Private Motive 02:58 Freudian Roots of Drive 03:37 Will’s Safety and Control Story 07:11 When the Why Leaks Out 07:35 Selling and Not Being Needed 09:57 Validation as True North 12:01 Ryan’s North Star Revealed 13:45 Will’s Revenge and Proving 16:07 Steve Jobs Still Hurt 17:57 Haters And Criticism 18:44 Minimum Viable Ego 19:29 Different Success Thresholds 20:47 Stop Trying To Prove Them 21:22 Pick The Right Vehicle 22:05 The Villain You Invent 23:45 Success Doesnt Fix You 29:17 Money And Marriage Myths 30:25 Alignment Over Ego Death 31:03 Autonomy As The Real Goal 32:34 Own Your Motivation Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin LinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroter https://www.linkedin.com/in/wilschroter/ Ryan Rutan https://www.linkedin.com/in/ryan-rutan/