10 Years In VC: What I Got Wrong at the Start
"VCs are like LLMs - they feel compelled to give you an answer if you ask a question, even if they have no knowledge or experience of the topic."
A founder recently said this to me, and after laughing out loud for real, it made me reflect on my own experience as a VC.
After a decade in venture capital, I've learned a counterintuitive truth of this business:
The best thing you can do for a founder is often nothing at all.
When I started, I thought my job was to help.
To have answers. Hustle like hell to find them if I didn’t have them.
To share “wisdom” from other companies I’d seen.
It came from a good place—wanting to add value.
But it was wrong.
Because most advice is context-poor.
What worked in one company, in one market, in one decade…is often irrelevant, or even harmful, in another.
Founders need real, relevant perspective—from people who are in the arena building right now, or customers adopting today, so they can decide for themselves. So now I spend my time helping by keeping my network more refreshed than theirs so I can get them to these people faster. Or I help by just listening when they need it.
Another uncomfortable truth we don't always want to admit as VCs: exceptional founders don't need us. They will stop at nothing to achieve their mission. We might help them get a key hire or a customer faster, but they would have gotten there anyway.
The reality is liberating once you accept it. Instead of trying to be indispensable, you can focus on being genuinely useful in the moments that matter.
This shift has required growth on my side too. In a session with a coach, I once realized my own sense of self worth came disproportionately from feeling like I helped someone. I was optimizing for feeling useful, not founder success. The two aren't the same thing.
I now think about it as finding exceptional people and enabling them to truly thrive.
How you enable someone to thrive is so different and specific to that person.
But largely, if it’s something I can uniquely help with, I’ll push like you wouldn’t believe - just ask my founders. If not, I leave teams alone to build and minimize annoyance, which they truly appreciate.
The best investors are probably like great jazz musicians - they know when to play and when to stay quiet.
My approach today:
- Connect, don't correct. Prescribe almost never. Always connect founders to someone with recent, relevant experience.
- Listen, don't lecture. The founder journey is isolating & hard. Sometimes the most valuable thing to offer is listening without judgement.
- Enable, don't dictate. Create the conditions for amazing founders to thrive.
And then… just get the fuck out of the way.
Great venture capital isn’t about having all the answers.
It’s about helping founders unlock their own.
Founders — what’s the most useful thing a VC has ever done for you?
VCs — what’s the most counterintuitive thing you've learned about venture?
