Right, When Others are Average

Lazy, or obsessed over efficiency

TLDR: Game everything. By definition, to be better than average, you need to be different.

There’s a pretty obvious reason I like what I do for work.

Growing up, I felt like I saw obvious things other people didn’t, or maybe I had a greater belief in myself than others did in me.

I felt like I was always right and other people never took the time to understand my point of view.

Teachers, mainly. I think that’s why I hated learning and studying as a kid.

Compare that to venture capital though—I get paid to be right when others are wrong. I get paid to be counterintuitive, non-consensus, unilateral, unique, and creative.

Of course you can be right when others are right, but usually that market prices that risk in. Crypto, AI, etc etc — all over-priced in their hype cycles because the edge is lost and the price is too high.

To make money, and not just money, but top 1% kind of money, you need to see those things before they’re happening and make big bold bets giving you both the edge and the entry price. You need Black Swan type of outcomes; like betting against the housing market in 2007.

Ok you don’t “need” those things—sure you can walk into a casino and put it all on 11, but even that only pays 35:1. Where are you going to get 10,000 to 1?

Uber. Airbnb. Ethereum. Bitcoin. But you need to have done it 10+ years ago.

So what’s today’s version of that? The answer is very simple, and it’s the same thing that it has always been.

It’s people.

You can hypothesize all you want about Moore’s Law, or the timing of physics breakthroughs that’ll bring quantum computing mainstream. You can go down the rabbit hole of a new kind of periodic table. You can even find ideas that purely sound crazy like building new kinds of rockets and airplanes, or back longevity drugs that promise to extend not just the lifespan, but the healthspan of every living organism.

I mean yes, do that, why not, but at the end of the day, it’s people.

Pick asymmetric people. People who work harder than you. People who are smarter than you. People who know things that you don’t. People who are students of the game they’ve chosen to play and understand how to beat it.

Ultimately that’s what succeeding in life is isn’t it? Picking a game you’re asymmetrically good at?

That’s what family is for some. Work for others.

For me, that’s what school was. How can I get through this with as little work as possible, but still at a level that won’t ruin the rest of my life? A top 20 school without doing a single night of homework? Transfer in. A respectable 3.2-3.4 GPA with the minimal work? A course load with easy teachers and topics that actually interested me. School arguably did teach me something—how to play the game.

That’s what baseball was for me too. I wasn’t the tallest or strongest or fastest, but I one hundred percent without question outworked and had a higher baseball IQ than every single team we played against. We won 3 championships. And 2 more in the summer league I coached after that.

And the same was true in sales. It’s a game to play, and the way you win is by being different to create asymmetry. You find what works, while also challenging every detail of the job in order to get the outcome you want. Game the compensation plan. Game the sales playbook. Game the product offerings. Game the impact numbers. Game the relationships. Game the hours you work. Game everything.

It’s the obsession over the details that matter. It’s where little edges developed turn into massive competitive advantages.

Most people see it as strange or lazy, but in reality it’s an obsession over efficiency. What’s actually lazy is simply doing the best practices of everyone else. Doing the same homework, running the same sales plays, working the same defined hours, filling out the same TPS reports.

I got three messages last week from former teammates at LinkedIn. Even to my surprise, they all shared a similar sentiment, unprompted, about the one thing I imparted on them that has stuck with them to this day—the creativity in deal structure and how to work the game.

I simply cannot understate how important this is.

By definition, to be better than average, you have to be different.

People underestimate it. They don’t get it. They don’t obsess. They don’t see creativity in the cracks of the details.

That’s, I think, why I always felt right when others thought I was wrong. And I probably was wrong a lot. But, in the cases where I was right, the payoff was material.

Championships won. Degrees achieved. Commission checks. Promotions. You name it. You’re rewarded more for being right when others are wrong.

In fact, you’re even rewarded for being right when others are average.

And that’s my big bet on my career in venture. Challenging all of the details.

Don’t invest up front. Follow-on with mathematical consistency. Find people who resemble the above thought patterns and beliefs in themselves. Invest in the people who play the game better than others, who take risks when others won’t, who work harder than others, but smarter and more creatively too. That’s how you win anything.

See you Monday.