Where were you when I was broke?

Where were you when I was broke?

Author: Startups.com June 30, 2026 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 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/


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
How to be Great at Worrying [not-audio_url] [/not-audio_url]

Duration: 35:55
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 rumina…
Can Startups Be a Team of One? [not-audio_url] [/not-audio_url]

Duration: 43:05
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 comp…
Why are we Really Building a Startup [not-audio_url] [/not-audio_url]

Duration: 33:43
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 i…
We Rarely "Control" Our Startups [not-audio_url] [/not-audio_url]

Duration: 46:35
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 ag…
Founders Need Finish Lines [not-audio_url] [/not-audio_url]

Duration: 38:33
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 fallac…
What Should My Expectations Be? [not-audio_url] [/not-audio_url]

Duration: 47:47
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.” Usi…
What Actually Happens When A Founder Runs Out of Gas? [not-audio_url] [/not-audio_url]

Duration: 34:11
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 panicki…
The Value of Distraction [not-audio_url] [/not-audio_url]

Duration: 35:04
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…
Master Failure [not-audio_url] [/not-audio_url]

Duration: 36:07
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 go…
We Can't Predict the Future Anymore [not-audio_url] [/not-audio_url]

Duration: 37:36
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 ecosyste…