♟ Play the right games

This is the most important skill to master when you're young

Morning, Players.

Today’s piece is on the concept of game selection. I think it’s probably the most important skill you can master as a young person trying to make your way in the world.

Enjoy.

Play the right games

In poker, the most important skill to make a lot of money is not playing a tight range of hands. It’s not stylish post-flop play or adhering to a game theory optimal play style. And it’s certainly not “reading the man” as the movies would have you believe.

It’s a much less sexy skill called game selection.

Daniel Negreanu, widely considered to be the best poker player in the world, recently explained this concept:

“Good is relative. You could be the seventh-best player in the whole world. But if you’re playing with the other six, you’re the sucker.”

In other words, where you sit down to play is infinitely more important than your actual ability. If you can nail your game selection, you’ll be incredibly successful in whatever game you choose to play.

Joining Morning Brew at the right moment

When I came across Morning Brew, I was nobody. I hustled my ass off to get my foot in the door, not really sure if I belonged at the table or not.

I went from cold emailing random people in Portland Maine to writing one of the biggest business newsletters in the world. I had gotten a seat. But now it was time to try and win the game.

And here is where the poker metaphor gets even cleaner.

I was immediately dealt a winning hand. During my time running the Brew’s Twitter account, GameStop mania happened. It was one of the craziest periods in financial history and I was in control of the Twitter account of one of the fastest-growing business media brands in the world.

I remember posting tweets and watching as they’d rack up 1,000 likes in the first 60 seconds.

By the time the dust had settled, I had grown the account by nearly 45,000 followers in a single month and over 270,000 in less than 18 months.

I had risen to the top of my field and was considered an expert at running and growing brand accounts. I went on podcasts. I had job offers left and right…and yet hindsight has allowed me to realize that a healthy portion of my success could be attributed to being in the right seat at the right game.

Yes, I made the right moves, but honestly, the game was so good it was hard to lose.

Milk Road

There is a popular newsletter called Milk Road started by My First Million’s Shaan Puri. Shaan is a good dude, well-liked in the content game, and someone who I have a great deal of respect for.

Yet, he pulled off one of the heists of the century with his latest business venture.

If we think back just 12 months ago, the web3 boom was well underway, bitcoin was pushing $60,000, and the entire world was sucked into the crypto moon cycle.

Shaan saw this, selected his game, and decided to take a seat. He started a newsletter called Milk Road that covered the web3 and crypto world. It had a recognizable slapstick tone and the content was good enough to keep people opening frequently.

The Milk Road team hammered Facebook ads to acquire readers and quickly grew it to over 250,000 subs. Then as the crypto clock stuck midnight, he sold it for a cool 7-figures.

Looking back it’s clear as day that Shaan’s greatest skill that netted him millions was not being a fantastic newsletter writer or a freak in the Facebook ad sheets.

Instead, his best skill was choosing to start a crypto newsletter when everyone and their mother was diving headfirst into space.

It’s game selection all the way down.

The cycle continues

We’re seeing Shaan’s playbook being executed in front of our eyes in real-time as the AI boom gets underway.

Yes, it’s annoying to read the thousands of “99% of you are using AI wrong” threads that sound like AI wrote them.

But all these people are doing is choosing an easy game to play and reaping the rewards.

I kinda despise these people, but deep down I have a grudging respect. They are the one’s making money while I’m writing 1,000 words hating on them.

Hell, I am playing an easy game once again. I joined Morning Brew for a second right in time for a once-in-a-decade banking crisis to hit. I got a GameStop moment two weeks into being on the job.

So while people might look at the success of my time at the helm of the new Morning Brew Daily account as a product of Toby bringing the magic touch back, I know that I was dealt another incredible opportunity that helped maximize my chance of success.

Final thoughts

Yes, execution is important. As is putting in the work. But as you take stock of your career and life, make sure you are playing the right games.

That doesn’t mean always playing the easiest—Elon is the richest man on Earth because he chose to solve some of the hardest problems facing humanity.

But even he is game selecting. Buying Twitter was a stupid game and even though he is a smart guy, he won’t win it at the scale of a Tesla or a SpaceX.

So before you apply for your next job, hit on someone at a bar, or play some poker, remember skill isn’t nearly as important as you think.

Just choose to play the right game.