As I’ve argued before, you have to pick your game before you can start winning.

But that’s of course easier said than done.

How do you actually find out which game is the right one for you?

The most common approach is to just try whatever sparks your attention; oftentimes everything at the same time.

This is quite obviously a recipe for failure.

You will always be distracted by whoever screams the loudest that their approach is the best. And the most interesting games will always remain hidden from your sight since people rarely make YouTube videos on them.

Moreover, you will never get any clear data when you try things in parallel.

Maybe dropshipping would’ve worked if only you’d gone all in? You’ll never know since you got distracted and started building affiliate niche sites.

Now I’m pretty sure you can see where I’m going with this.

You need to do proper research. You need a plan. And you need test things one after another instead of multiple things at once.

The first step is getting a lay of the land. Start with a list of all the options available. Try to make it as granular as possible.

For example, when your goal is to make a living “doing sports”, it’s not enough to just write down soccer as one of the options. There’s futsal, 7 vs. 7 soccer, and 11 vs. 11 soccer. Each of these options requires unique skills and has a different risk-reward profile.

The same is true for entrepreneurship. For example, even within a category like media businesses there are lots of different options:

• You could monetize content via an agency, like VaynerMedia.
• You could start with an email list and then monetize it by selling your own products like Thrillist.
• You could publish a physical magazine like Offscreen Mag.
• You could start a network of automated newsletters like HN Digest or Arkwatcher.
• Or you could go down the indie route and start a newsletter under your own personal brand like Lenny Rachitsky.

The next step is to figure out what style of business model fits your interests but also helps you succeed faster depending on what your goals are.

For example, owning a content agency is definitely a great conversation starter. But it also requires managing a ton of people.

To build a media company like Thrillist you will have to raise funding to get if off the ground. So this is only a good fit if you know how to raise money or are interested in learning how to do it. It also requires hiring and managing writers.

And building a network of automated newsletters requires technical skills. Otherwise, you won’t have any ideas of what’s possible. But they’re also hard to grow, there’s no moat, and always the risk that they stop working when your data source gets shut down.

The key lens to evaluate all these different options through are your personal unfair advantages.

For example, if you have lots of investors in your network, the Thrillist model definitely should be high up on your the list.

Similarly, if you know how to code, it definitely makes sense to add some additional weight to business models that require technical skills. After all, most people in the media industry can’t. So this is definitely something you should leverage in some way.

Other examples of unfair advantages would be if you have some savings, unique insights, and are a great writer yourself. In that case, the indie newsletter playbook should get a few additional points.

I could now of course give you my list with all the pros and cons of different business models I identified. But I’m convinced that all the value is in thinking things through for yourself.

Your list will and should be heavily colored by your personal preferences and biases.

It’s a bit like with the famous coin flip trick you can use whenever you can’t decide between two options. The moment the coin is up in the air, you suddenly know what you’re hoping for.

In the same way, you will subconsciously favor business models you’re truly passionate about when you prepare the list. And being passionate is definitely another huge unfair advantage.

The next step is to let your list sit for a few days.

Then you look at it again, pick the best option, and go all in.

In the unlikely case that it doesn’t work out, rinse and repeat.