Startup Therapy

Latest Episodes:

100 CEOs Oct 26, 2026

Show notes

What if the reason so many former employees become CEOs isn’t genius hiring, but creating the conditions that let CEO-level potential show up? The conversation breaks down how to spot and develop high-upside talent by treating people like peers, inviting them to take on responsibilities above their current role, and gradually increasing the difficulty of tasks to build confidence and capability. They argue most people aren’t “CEO-ready” when hired, but can grow quickly when given respect, room to run, and a safe-to-fail environment with repeat chances instead of punishment. The hosts contrast this with corporate cultures that train people to avoid risk, and suggest founders should think like VCs: make broad bets, expect failure, and invest in the few breakouts who become game changers—often leaving to start their own companies.

02:01 Potential Not Pedigree
04:04 Thrown Into Deep End
07:01 Invitation Not Pressure
10:04 Early Talent Tells
11:11 Torch And Google
12:43 Progressive Challenges
15:32 Sales Lessons Learned
18:29 Avoid Spreadsheet Traps
20:21 Founder Mentality Culture
21:01 How Many Miss Out
21:38 Groups Startup Plug
22:10 Back To Age 19
22:34 Raising Your Ceiling
23:27 Fork in the Road Skills
24:20 Unlocking Potential Energy
25:09 Superstars and Deep Benches
26:44 Big Bowl Expectations
27:41 Let Them Crash and Learn
29:58 Failure as the Business
32:22 Fertilizer Not Molding
33:54 Hittable Pitches and Wins
39:15 Mistake Budgets vs Allowances
39:48 Alumni Founders and Pride
40:55 Send Them Off to Build
42:40 A Thousand New CEOs

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/

We Need "Unfireable" Founders Sep 08, 2026

Show notes

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 must keep going long enough to find the few bets that work. Unlike traditional executives who operate with guardrails, founders need extreme autonomy to make unconventional, often irrational decisions that can produce outsized outcomes, as illustrated with Steve Jobs, Elon Musk, and Travis Kalanick at Uber, contrasted with operator CEOs like Tim Cook and Dara Khosrowshahi. The hosts also warn that the same freedom is a founder’s kryptonite, citing WeWork as an example of hubris and lack of accountability. They close by noting AI is increasing founder latitude, raising both opportunity and danger, and emphasizing the value of rational advisors without letting them control the vision.

00:00 Founders Cant Be Fired
01:32 Wrong Most Of The Time
02:59 Comprehensively Wrong Bets
08:53 Unbridled Risk And Returns
19:06 When Praise Enables Madness
22:47 Critics Are Always Right
23:36 Mentors Weren't Built Yet
24:25 Old School Advice Mismatch
29:57 Choice Paradox Everywhere
36:55 Unfireable In Early Years

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 a Horrible Startup Advisor Aug 17, 2026

Show notes

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-awareness about their bias and the weight their words carry. Ryan and Will unpack how founders, who often can’t tell “ground truth” from bravado, can be pushed into bad decisions by overconfident feedback—particularly from investors and local “yokels” with narrow worldviews. They share examples from pitch competitions and boardrooms, argue that delivery is often more harmful than the advice itself, and highlight “you might consider” as a simple way to add humility and optionality. The key takeaway: great advisors avoid ego, disclose uncertainty, and help founders synthesize perspectives rather than obey directives.

00:00 Why Advice Needs A Test

01:17 Confidence Becomes Fact

03:39 Pitch Judge Hyperbole

10:30 VC Power Dynamics

15:10 Advice Not Facts

17:03 You Might Consider

18:28 Conflicting Perspectives

22:53 Bias And Obedience

28:07 Do No Harm

32:59 Community Outro

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/

Which Version of Me is Coming to Dinner Tonight Aug 03, 2026

Show notes

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, calm leader, guarded partner—because the honest answer (“I don’t know” or “we’re struggling”) can carry real consequences with investors, employees, customers, friends, and family. The conversation explores the difference between confidence about an uncertain future versus crossing into deception, the emotional burn rate founders pay to stay composed, and how compartmentalization becomes muscle memory—even through illness, grief, or shutdowns. They highlight how group dynamics push founders to match the room’s tone, and why having one place to take the mask off—like a trusted founder group—can be essential to staying sane and healthy.

03:27 First Pitch Meeting Lesson
04:33 Choosing What To Share
07:26 Buckets Of Consequence
15:54 Gray Area Of Belief
19:07 Founder Pressure Cooker
20:50 Founder Groups And Leaks
27:55 Working Through Pain
30:52 Joy Versus Consequence
36:23 Honesty Sets The Tone
42:06 You’re Not Alone

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 Death of the Technical Cofounder Jul 20, 2026

Show notes

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 Requests
03:14 The Old Quest for Coders
07:50 When Coding Got Too Hard
10:16 VC Bias Toward Technical
21:59 Prototype Value Myth
29:32 Chaff Skills Explained
31:04 Builders Get The Rocket
42:27 Golden Era For Founders
42:50 Bionic Co Founder Future

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/

We Do What Other's Won't Jul 14, 2026

Show notes

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 Do
04:41 Why Founders Get Paid
09:47 Rejection and Being Wrong
12:31 High Achievers vs Founders
15:58 Building the Willingness Muscle
18:45 Willingness Beats Talent
29:36 Real Reward Is Autonomy
32:51 Aspiring Founder Reality Check
34:52 Worth It in the End

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/

Everyone is a startup... Again Jul 06, 2026

Show notes

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 Overnight
02:57 Three Switches Flipped
04:07 Startups.com Case Study
06:48 Speedrun Not Disruption
10:01 Competitors That Never Die
16:45 The Staffing Reckoning
17:28 Answers Already Exist
18:00 AI Pivot People Fallout
20:05 Hard Reset Reality
23:10 Big Company Politics
34:09 Level One With XP
36:03 Founders Win Again

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/

Where were you when I was broke? Jun 30, 2026

Show notes

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 Opinions
02:55 Guidance Counselor Doubt
04:13 Early Support Matters
05:44 Nineteen Dollars Start
06:53 Ten Thousand Loan
09:55 Wide Angle Victory
10:38 Doubt Chokes Founders
11:38 Young Founder Respect
14:59 I Told You So Bias
18:49 Funding Round Whiplash
20:20 Recruiters Disappear
21:30 Success Rewrites History
23:03 Sam Altman Backlash
25:40 Founders After Success
28:32 Timing Is Support
32:00 Must Be Nice Myth
35:56 Bricks in Foundation

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/

What if I'm the Best, but don't know it? Jun 23, 2026

Show notes

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/

Founders Don't Retire Jun 15, 2026

Show notes

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 Relief
00:57 Carpenter Story and Pain
03:06 Four Minute Founder Brain
04:31 Broken Retirement Dream
05:13 Reload and Retire Again
06:31 Beach Metaphor Explained
09:58 Athletes vs Founder Longevity
12:00 Vacation Checklist Trap
15:35 No Substitute for Mission
17:29 Finish Line Fantasy
18:45 Recovery Not Retirement
20:35 Builders Need Purpose
25:14 Retired But Uncharged
27:00 Creation Over Consumption
30:16 Retirement On Your Terms
32:26 Design Better Circuits

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/

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