Four Lessons From Fred Wilson

I really admire Fred Wilson for his clarity of thought. So when he gave a talk where he listed out four lessons from his life, I just had to write them down.

My favorite one is the last one.

First lesson

A VC's most important role is that of a cheerleader. It may seem like nothing, but it is everything.

Wilson draws this from General Georges Doriot, the "father of venture capitalism", and from whom Wilson learnt everything about venture capital.

It doesn't just apply to venture capital. If you lead a team, you have to be their biggest cheerleader: you have to be the one creating the energy around them that will spur them to say yes, to work together, to create innovative solutions, and not give up. This is true whether you are their direct manager or an indirect manager or a tech lead. Without this, they will not be able to persist or solve hard problems — which is all we do in tech. There are solved problems and there are hard problems — there are no easy problems. And no one gets paid for solving already solved problems.

Second lesson

You need a cheerleader in your life. Find one.

He says his wife was his biggest cheerleader, and calls her the secret of his success. Like Doriot, he says, she understood the importance of this support and believed in Wilson from the start.

I see this as a corollary to the first lesson. Just like you need to be a cheerleader for your team, you need a cheerleader for yourself. The world and the business environment we inhabit is more volatile than ever. To be able to persist and do our best work, you need someone who can always point out to the light through the fog.

Third lesson

Fucking up royally is good for you, if you take the time to learn from it.

The playbook he came up with after his first venture capital firm failed was the reason of his success. He says he spent a couple of years "licking his wounds" after Flatiron Partners and thinking about what had happened.

This rings true for me too. Skills do not develop linearly in life and when I look at the jumps in my abilities, they have always been after disastrous failures. If you want to convince me you are good at something, you'll have to tell me about when you were bad at it!

Fourth lesson

The best time to invest in something is when nobody believes in besides you. You have to totally believe in it, and you have to know why.

Wilson refers to his first fund, and the thesis it was based on. It was his best fund and one of the best the industry has seen, returning 15x when most people refused to participate in it and laughed at the notion of investing in the internet (there is still more in the fund to return).

The part I like the most here is: "you have to know why".
That is what creates the difference between being wrong and being perhaps right. If you are able to reason about the why, you will be able to understand when and where you are wrong and shift course accordingly. Fred Wilson, for that first fund, had written a manifesto to help himself articulate the why.

People are never entirely right or entirely wrong, just more or less. The picture starts out as blurred, and as parts of it comes into focus, it is crucial to know which parts you are right about and shift towards those.

Watch the entire lecture here: