why founders underestimate their advisors
you're paying for access to someone's failure, not their success. the stories usually begin "this broke."
Most advisors are selected for what they've accomplished.
Wrong filter.
You want to select for what they've done wrong and survived.
I've sat on boards with two people who've scaled to $100 million+. And I've learned more from an advisor who shipped something that crashed and had to rebuild it twice.
Why? Because the $100M person is usually describing the path that worked, with the failure parts edited out. The person who crashed and rebuilt twice is giving you the actual operating knowledge.
When you're doing something new—and all early-stage startups are—you don't need someone who succeeded in a predictable way. You need someone who's failed intelligently.
The specific failures matter. Did they fail on product-market fit and then find it? Or did they scale to 50 people and realize they built the wrong thing?
Those are different lessons, and you want the one that's closest to your risk right now.
I turned down an advisory role recently because the person had succeeded big, but in a space that's nothing like what the founder's building. The success was uninformative.
I took another because the person had failed twice in spaces that looked similar to this founder's future problems.
What would change if you picked advisors for their specific failures, not their general pedigree?