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Startup Therapy

Startup Therapy

Startups.com 335 Episodes Jun 30, 2026

Startup Therapy is a podcast that offers a no-nonsense look at how startups are truly built, hosted by actual startup founders Wil Schroter and Ryan Rutan. They discuss the intense personal and professional struggles founders face while trying to turn their ideas into world-changing companies.

Episodes

Where were you when I was broke? Jun 30, 2026 2932 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 change
What if I'm the Best, but don't know it? Jun 23, 2026 3271 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” in
Founders Don't Retire Jun 15, 2026 2028 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 no
The Right Time to Start is Right Now Jun 8, 2026 2290 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 sc
The Most Expensive Equity Doesn't go to Investors Jun 1, 2026 2781 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 fu
How to be Great at Worrying May 25, 2026 2155 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
Can Startups Be a Team of One? May 18, 2026 2585 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-founde
Why are we Really Building a Startup May 11, 2026 2023 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
We Rarely "Control" Our Startups Apr 13, 2026 2795 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 bo
Founders Need Finish Lines Apr 6, 2026 2313 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 paran
What Should My Expectations Be? Mar 23, 2026 2867 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
What Actually Happens When A Founder Runs Out of Gas? Mar 2, 2026 2051 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, pushi

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