Startup Therapy

Osad

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  The Death of the Technical Cofounder 20.07.2026 43min

  What if you could build a working prototype without giving away half your company? The episode argues that tools like Claude have ended the old “technical co-founder as early-stage gatekeeper” dynamic: founders used to need a developer to cross the first binary hurdle from idea to product, and some investors also pushed for technical co-founders before funding. Now, founders can ship prototypes in a weekend with an AI subscription, pushing the vulnerability window later and repricing equity. The hosts stress technical talent still matters—especially for scaling and real engineering—but AI exposes the difference between people who only had scarce, auditable-by-no-one skills and those with true product, systems, and architecture value. They compare this shift to past disruptions like TemplateMonster commoditizing million-dollar websites, predicting a sorting of technical roles and a “new” bionic technical co-founder focused more on architecture than gatekeeping.What to listen for:00:47 Claude Ends the Requests03:14 The Old Quest for Coders07:50 When Coding Got Too Hard10:16 VC Bias Toward Technical21:59 Prototype Value Myth29:32 Chaff Skills Explained31:04 Builders Get The Rocket42:27 Golden Era For Founders42:50 Bionic Co Founder FutureResources: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/
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  We Do What Other's Won't 14.07.2026 35min

  What are you actually willing to do to get what you want as a founder? Using Will’s 6:00 a.m., 15-degree framing session and a dumpster-diving Bobcat mishap as metaphors, this episode breaks down what separates founders from everyone else: an “unreasonable” willingness to do hard, risky, uncomfortable things repeatedly—often without any guarantee of payoff. The conversation explores the real price founders pay (uncertainty, rejection, sacrifice, and daily grind), why high achievers used to clear reward loops can struggle in startup chaos, and why outsized outcomes tend to follow people who endure what others won’t. They also unpack common misconceptions about wealth and merit through examples like Jason Calacanis, Elon Musk, and elite athletes, and argue that the deeper reward isn’t money—it’s autonomy and ownership of your outcome.What to listen for:02:13 Nothing I'm Not Willing to Do04:41 Why Founders Get Paid09:47 Rejection and Being Wrong12:31 High Achievers vs Founders15:58 Building the Willingness Muscle18:45 Willingness Beats Talent29:36 Real Reward Is Autonomy32:51 Aspiring Founder Reality Check34:52 Worth It in the EndResources: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/
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  Everyone is a startup... Again 06.07.2026 38min

  What happens when AI turns your hard-won moat into a weekend project? This episode argues that AI has effectively forced established companies back into “startup mode,” wiping out long-held assumptions about products, staffing, and competitive advantage. Will and Ryan break the reset into three shifts: the cost to build and operate has collapsed, big teams and legacy systems have become liabilities, and “everything is buildable” faster than incumbents can adapt. They warn that competitors can now reach product parity quickly and survive with tiny teams that don’t have payroll to protect, making old “wait them out” strategies obsolete. The hardest part is the human reset: org charts, roles, and business models must change even when it means cannibalizing what currently pays the bills. The companies that survive are those willing to restart deliberately, think like founders again, and use experience as the edge.01:09 Moats Filled Overnight02:57 Three Switches Flipped04:07 Startups.com Case Study06:48 Speedrun Not Disruption10:01 Competitors That Never Die16:45 The Staffing Reckoning17:28 Answers Already Exist18:00 AI Pivot People Fallout20:05 Hard Reset Reality23:10 Big Company Politics34:09 Level One With XP36:03 Founders Win AgainResources: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/
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  Where were you when I was broke? 30.06.2026 48min

  Ever notice how people show up loudest after you’ve already won? This episode digs into why founders often get the least support when the risk is highest—and the most opinions once success is “de-risked.” Will shares early moments of having virtually no safety net (including starting with $19, dropping out, and getting doubted), contrasted with the few timely “bricks” that actually changed his trajectory—like a risky $10K loan and a friend’s family offering a place to stay for the holidays. They unpack how funding wins, press, and exits attract late-arriving fans, opportunists, and advice that can derail post-success decisions, and why founders should take inventory of who truly showed up when things looked impossible—and be that kind of support for other founders.00:39 Elon Money Opinions02:55 Guidance Counselor Doubt04:13 Early Support Matters05:44 Nineteen Dollars Start06:53 Ten Thousand Loan09:55 Wide Angle Victory10:38 Doubt Chokes Founders11:38 Young Founder Respect14:59 I Told You So Bias18:49 Funding Round Whiplash20:20 Recruiters Disappear21:30 Success Rewrites History23:03 Sam Altman Backlash25:40 Founders After Success28:32 Timing Is Support32:00 Must Be Nice Myth35:56 Bricks in FoundationResources: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/
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  What if I'm the Best, but don't know it? 23.06.2026 54min

  What if building a company is the fastest way to find out what you’re actually capable of? This episode explores how startups don’t just get built by founders—startups build founders by forcing them into new roles like finance, sales, marketing, design, legal, and leadership, often before they feel ready. Will shares how real stakes (like cash flow and payroll) turned “I’m bad at math” into practical financial skill, and why getting to ~80% proficiency across key areas creates leverage, better decision-making, and protection against getting bullshitted. The conversation digs into how exposure and environment unlock hidden potential (from Lars Ulrich’s story to personal career turning points), why most “I can’t” is really “I haven’t,” and how repeated reps, feedback, and humility turn competence into confidence—plus a cautionary backup-dancer story about confidence without practice.What to listen for:02:10 Creating Your Own Role03:59 From Math Failure to Finance07:04 Asking Dumb Money Questions09:35 Become What Company Needs10:47 The 80 Percent Rule11:42 Agency Skills Stack15:12 Cross Skill Superpowers16:44 No One Can Bullshit You19:05 AI as Private Tutor20:13 Exposure Creates Greatness27:03 Defining Moments Reframed29:18 Dad Versus Computers32:48 Reinventing Your Identity39:26 Founder Reinvention Loop42:27 Craftsmanship And Parenting45:36 Dance Off Reality Check52:28 What If And Keep MovingResources: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/
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  Founders Don't Retire 15.06.2026 33min

  What if “retirement” for founders isn’t about stopping work, but finally getting relief? The conversation unpacks why builders rarely stop building: founders are wired to create, not to consume, and the fantasy of beach life usually shows up at a low-energy point when what’s really needed is recovery. They compare founder burnout to wanting the finish line without running the race, and note how exits often lead from “margaritas” to “domain names” within months because the calling returns once the nervous system resets. The key reframe: separate a recovery plan from a retirement plan, and define “retirement” as creating on your own terms—less panic, fewer hated parts (like investor pressure or endless hours), more control, and a sustainable way to keep doing the work you love.What to listen for:00:49 Builder DNA and Relief00:57 Carpenter Story and Pain03:06 Four Minute Founder Brain04:31 Broken Retirement Dream05:13 Reload and Retire Again06:31 Beach Metaphor Explained09:58 Athletes vs Founder Longevity12:00 Vacation Checklist Trap15:35 No Substitute for Mission17:29 Finish Line Fantasy18:45 Recovery Not Retirement20:35 Builders Need Purpose25:14 Retired But Uncharged27:00 Creation Over Consumption30:16 Retirement On Your Terms32:26 Design Better CircuitsResources: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/
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  The Right Time to Start is Right Now 08.06.2026 38min

  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 Reality02:00 Readiness Comes After02:34 First Founder Breakthrough07:41 Micro Center Origin Story10:07 Cost of Waiting11:14 Planning Versus Theater12:23 Test With Customers14:09 Ecommerce Pitch Fail16:41 Whiteboard Versus Field18:48 Learning By Building19:35 Learn By Doing20:05 Founder Skill Stack20:45 Econ 101 Mindset Shift22:45 Human Potential Unlocks24:27 Momentum Beats Certainty25:58 Plan To Learn Fast30:26 Conditioned To Avoid Failure34:34 Cost Of Waiting35:50 Action Over Perfection36:47 Stop Waiting Start NowResources: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/
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  The Most Expensive Equity Doesn't go to Investors 01.06.2026 46min

  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/
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  How to be Great at Worrying 25.05.2026 35min

  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/
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  Can Startups Be a Team of One? 18.05.2026 43min

  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/
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  Why are we Really Building a Startup 11.05.2026 33min

  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/
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  We Rarely "Control" Our Startups 13.04.2026 46min

  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/
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  Founders Need Finish Lines 06.04.2026 38min

  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/
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  What Should My Expectations Be? 23.03.2026 47min

  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/
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  What Actually Happens When A Founder Runs Out of Gas? 02.03.2026 34min

  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/
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  The Value of Distraction 23.02.2026 35min

  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/
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  Master Failure 16.02.2026 36min

  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/
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  We Can't Predict the Future Anymore 09.02.2026 37min

  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
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  We wanted efficiency. We got isolation. 02.02.2026 41min

  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
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  Are startups the future of employment? 03.12.2025 47min

  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