How to be a Horrible Startup Advisor

How to be a Horrible Startup Advisor

Author: Startups.com August 17, 2026 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-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/


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…