What if I'm the Best, but don't know it?

What if I'm the Best, but don't know it?

Author: Startups.com June 23, 2026 Duration: 54:31

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 Role
03:59 From Math Failure to Finance
07:04 Asking Dumb Money Questions
09:35 Become What Company Needs
10:47 The 80 Percent Rule
11:42 Agency Skills Stack
15:12 Cross Skill Superpowers
16:44 No One Can Bullshit You
19:05 AI as Private Tutor
20:13 Exposure Creates Greatness
27:03 Defining Moments Reframed
29:18 Dad Versus Computers
32:48 Reinventing Your Identity
39:26 Founder Reinvention Loop
42:27 Craftsmanship And Parenting
45:36 Dance Off Reality Check
52:28 What If And Keep Moving

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/


Building a company is far more chaotic and personal than any business school case study lets on. Startup Therapy from Startups.com digs into that reality, moving past polished success stories to focus on the raw, unvarnished journey. Hosts Wil Schroter and Ryan Rutan, who have each navigated these trenches themselves, lead conversations that feel more like essential conversations between founders than a standard interview show. They tackle the specific pressures that come with trying to transform an idea into something meaningful-the financial strain, the team dynamics, the personal sacrifices, and the frequent moments of doubt that rarely make the keynote speech. This podcast operates on a simple premise: the best guidance comes from those who have been there, not from abstract theory. Each episode is a candid session, dissecting the professional hurdles and the intense emotional toll that founders manage daily. You’ll hear direct talk about fundraising fails, partnership conflicts, burnout, and the small victories that keep everything moving forward. It’s a resource for anyone in the thick of building something, offering practical perspectives and a sense of shared experience when the path gets especially tough. The dialogue is straightforward and focused on actionable insight, providing a genuine look at the resilience required to change the world, one startup at a time.
Author: Language: English Episodes: 50

Startup Therapy
Podcast Episodes
We Need "Unfireable" Founders [not-audio_url] [/not-audio_url]

Duration: 38:33
Why do founders have to be “unfireable” for a startup to work? The episode argues that founding is the only job where you create the role yourself, have no real credentials, and will be wrong most of the time—yet you mus…
How to be a Horrible Startup Advisor [not-audio_url] [/not-audio_url]

Duration: 33:22
Ever gotten startup advice that sounded like a fact—but was really just someone’s confident opinion? This episode breaks down why so much startup advice is dangerous, especially from well-meaning advisors who lack self-a…
Which Version of Me is Coming to Dinner Tonight [not-audio_url] [/not-audio_url]

Duration: 43:50
Ever wonder which “version of you” should show up to dinner, a board meeting, or a team update? This episode breaks down why founders feel like they’re constantly auditioning different personas—optimistic forecaster, cal…
The Death of the Technical Cofounder [not-audio_url] [/not-audio_url]

Duration: 43:48
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 n…
We Do What Other's Won't [not-audio_url] [/not-audio_url]

Duration: 35:41
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…
Everyone is a startup... Again [not-audio_url] [/not-audio_url]

Duration: 38:17
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, st…
Where were you when I was broke? [not-audio_url] [/not-audio_url]

Duration: 48:52
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 ear…
Founders Don't Retire [not-audio_url] [/not-audio_url]

Duration: 33:48
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…
The Right Time to Start is Right Now [not-audio_url] [/not-audio_url]

Duration: 38:10
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 feed…
The Most Expensive Equity Doesn't go to Investors [not-audio_url] [/not-audio_url]

Duration: 46:21
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…