How to be a Horrible Startup Advisor

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 Test01:17 Confidence Becomes Fact03:39 Pitch Judge Hyperbole10:30 VC Power Dynamics15:10 Advice Not Facts17:03 You Might Consider18:28 Conflicting Perspectives22:53 Bias And Obedience28:07 Do No Harm32:59 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/