⭐️ It's time to win

16 months ago I decided to pursue a Bootstrap MBA instead of a traditional career.

During these months my online ventures generated a very comfortable 6-figure income. I got featured on my favorite podcast, launched 16 projects, sold some of them, grew my newsletters and Twitter account from zero to 5000+ subscribers, wrote tweets, threads, and essays that went viral, people started citing me as a source of inspiration and I met many amazing fellow online hustlers.

But I’m still hungry. Hungrier than ever. I definitely don’t feel as if I’ve made it.

As I reflected on my progress so far and my plans for the new year, it clicked.

Step 1 was to leave the sidelines, put myself out there and join the fun. This is what the Bootstrap MBA was all about. Thanks to the systems I set up for myself I successfully left my comfort zone and started building up my serendipity surface. Just as I had hoped, amazing things started to happen.

But what’s Step 2?

There are plenty of A-list players that operate at a level I can’t even start to comprehend. But I’m not even on the B-list or C-list. Realistically, I would put myself on the D-list right now. (In the film industry, the “D-list is for a person whose celebrity is so obscure that they are generally only known for appearances as celebrities on panel game shows and reality television”. As an analogy this seems quite fitting.)

On the A-list we have guys like Elon Musk or Jeff Bezos. And to be honest, I don’t think I can learn much from them. They are too far ahead and definitely have long forgotten what it’s like to be a beginner. It’s always smarter to learn from people just one or two steps ahead of you instead.

With this in mind, Step 2 is obvious: Figure out how who’s on the B-list and C-list players in the world of entrepreneurship and how I can get to their level.

My current systems that helped me get onto the D-list definitely won’t get me there. Just as I did with the Bootstrap MBA, I need to come up with a new plan, new systems, new processes.

So far I barely scratched the surface. I learned the most basic rules and how to make a living online.

I learned how to play. Now it’s time to learn how to win.

You probably wonder: win at what?

The Great Online Game

Packy McCormick recently coined the term The Great Online Game for online entrepreneurship. And as Dror Poleg observes, “the game is no longer optional. Everyone must play. We have little to lose because we already lost everything: Stable jobs, affordable homes, education that lasts a lifetime, and worry-free retirement are no longer an option.”

Unfortunately, Packy and Dror both left out the most interesting part: how to win.

Packy claims that “every tweet is a free lottery ticket” which is obviously wrong. Twitter is not entirely a game of luck. While there are no guarantees that any given tweet will do well, there are strategies you can use to improve the odds in your favour. The same is true for every product launch, every essay or podcast you publish, and every cold email you write.

There are guys like Anthony Pompliano who play the Great Online Game like a fiddle. They are not simply playing, they’re winning.

And I want to learn how to do that.

Learning how to win

Now here’s a secret.

Guys like Pomp are winning because they’re playing a completely different game, the metagame.

So I started by reading everything about metagames in all kinds of contexts, looking for patterns. How do people play them? What are the patterns and generalizable lessons?

Here’s what I learned:

Lesson 1: The prerequisites for playing the metagame are mastery of the boring fundamentals and clarity on what game exactly you want to play.

Mastering the fundamentals is pretty much what I did during the past 16 months.

Lesson 2: The recipe for winning the metagame is: expertise + reasoning from first principles + a system for staying on top of things, where you can substitute expertise for pattern matching.

This led me to the following plan:

  • I need to actively study how the best players are operating until I’m able to spot patterns and generalize them. Importantly, I need to focus on what they do, not just on what they say. This is how I will build the necessary expertise.
  • Then, starting from first principles and using the patterns I identified, I will try to come up with novel strategies and ideas.
  • The system that will allow me to stay on top of things will have two components. Firstly, I will actively work on increasing my serendipity surface area. Many of the best opportunities come in the form of inbound messages. I will do this by publishing regularly on this site and then distributing my ideas on platforms like Twitter and Reddit. Secondly, I will schedule every week at least three hours to research new trends and opportunities. (I’m kind of lucky that some very generous readers pay me to do this.)

But most importantly, I will take a ton of swings. Expertise and ideas are worthless until you put them into action. Moreover, real world data beats opinions any day, in particular if it’s your own data.

This is obviously just a high level overview. But I already compiled of players I want to analyse, started to collect patterns, and rebooted this website and my Twitter profile with fresh content.

Now it’s time to get back to work.

Speak soon,


Written on January 13, 2022

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