Advice is earned by understanding the work

Zach DavidsonOct 2, 2026

A line from Matt Cynamon’s conversation with Fred Wilson and Nikhil reminds me of a useful standard for advising founders: writing a check doesn’t automatically qualify you to tell someone how to run their company. When Fred was 29, a founder challenged him to spend a week doing every job in the company before offering advice. Fred flew to Buffalo and did it. He quickly learned that advice lands differently when it comes from someone who has taken the time to understand the work and the people doing it. The conversation also touches on the other side of the job: building conviction when your partners disagree, while staying open to evidence that challenges your strongest beliefs. That balance seems hard to maintain. Confidence without curiosity turns into stubbornness; curiosity without conviction makes it difficult to act. I’m curious how founders and investors here think about this: What earns someone the right to give you advice? And what makes advice useful even when the person giving it hasn’t done your job?