I attribute a lot of my success to running every major career decision through this test from age 20 onward:

Which route increases the odds of me being able to do whatever I want with 100% my time when I’m 35 yrs old?

It turns out, when I really did the math, I didn’t need a unicorn startup.

I needed to stash about $1MM (after tax) by 27 and then invest it wisely from there.

Definitely wasn’t going to happen with grad school or law.

And most normal jobs didn’t cut it either.

So I started a small biz with really crappy competition and a sure-bet way to make $250k a year for a few years straight.

The rest is history.

And I achieved my goal 5 yrs early.

15 yrs (the time horizon back when i was 20) was a long time I guess.

And I ate ramen and skipped a few fun party trips I couldn’t afford.

And didn’t buy a new car or a big house as soon as I had the cash to do it sitting in the bank.

The funny thing is how fast it happened.

It took me to 28 to have a $1MM net worth.

I was behind schedule.

But by 31 it’s well beyond my stretch goals.

It turns out you get better at life and making money becomes easier as you can take larger and larger high-probability bets.

Momentum is a hell of a real thing.

If I would have shot for the moon on day one I would have failed.

I’d have a job right now. And you wouldn’t be reading this tweet.

For those who care:

My partner and I leveraged about $250k each + $500k from investors to build a self storage facility.

Kept the rest of the cash on the sidelines just in case.

Kept our service business running too.

2.5 years later that $2.5MM building was worth $5MM.

We did a cash-out-refinance and pulled out $2MM in cash.

And used that to buy 10 more buildings.

And then it really started piling up fast.

And then stuff started happening on the internet and it got even crazier. https://twitter.com/sweatystartup/status/1366557990225117184

And that’s it folks.

I’m just a guy who got a 23 on his ACT and was the last guy accepted into college (and only because the track coach worked to get me in).

But now I just do what I want all day.

And it turns out for 30 hrs a week or so that’s work.

But it’s fun work!

The interesting thing about all this:

The choice that leads to the most ego / status is rarely the choice that leads to the most likely chance of doing what you want when you’re 35.

Also the choice that leads to the “possibility” of big money in the near term isn’t the way.