Dream Big - $100M Big. Kill Your Imposter Syndrome.

With a $100M goal, you won’t languish

I’ve spent more than half of my adult life languishing. 

My friends might disagree.  

They’ll tell you I ran the #1 fund in the world, worked for a top hedge fund manager, worked for 4 billionaires, ran marathons, won races, and competed in the Dressage World Cup Trials. 


Goals don’t have to only be about money.  Mine were: 

1. Work at a top hedge fund

2. Be an effective Grand Prix dressage rider.

Once I hit them, I languished. I wasn’t looking for what was next.

My first goal was to work at a top hedge fund.


Once I got to the top hedge fund, I made a billion-dollar trade, making my boss more than $100M, and that followed making my prior boss $24 million in one year.  But I felt I had arrived, so I didn’t take the next step and go for ownership.


The next step to $100M would have been ownership in a fund or company.  Equity. 

Instead, I kept working as an analyst for other companies (and for less money as the industry went through downward fee pressure).

My second, non-monetary goal was to be an effective Grand Prix rider.

I made it to the 2005 World Cup Trials at the Grand Prix level.  I was 9th in the US.  But my horse and I were better than that.  I turned down riding on German National TV, riding at the Washington Invitational, and at the Las Vegas Invitational.  I didn’t take full advantage of where I was.

I saw myself as overshooting my plans rather than on a path to greater things.

So I languished.

What did I learn?

  • No one dreams big enough.

  • Enough is the enemy of progress.

  • If you want a great journey, set audacious goals.


Start with a $100M goal is starting with self-belief

I write about the steps to $100M:

  • Take risks to make a few million by age 30

  • Get ownership of what you are doing

  • Compound that money for 30+ years.  


How soon (or if) you reach $100M depends on the amount you start with, when you start, how long you compound, and the rate of return you earn.  Period.  That’s it.

But none of it works if you languish.  


None of it works without a big goal.  Each time you hit a little target, you will have to re-energize yourself and set another.  You risk saying you don’t have the energy to gear up for another goal.


This start-and-stop grind isn’t nearly as exciting as setting an audacious goal early.


A $100M goal starts with self-belief

Imposter syndrome starts early. Parents, siblings, and school rivals treat you as small. 


A huge goal, like a $100M Career, reboots your self-belief.


You’d have to be crazy to set such a high goal.  Yet, someone makes it.  25,000 households in the US are self made and worth over $100M.  


Might as well be you!

Is $100M enough?

Before you laugh…hear me out…You may overshoot.  

Of the 25,000 US households worth over $100M, the US has 720 billionaires.  These are people who grew up like you and me.

Bill Gurley, for instance, grew up in Texas, and started as a computer programmer at Compaq.  I met him when he was a computer analyst for Credit Suisse and I was working in New York at the hedge fund Palantir.  He is extremely smart and was often ranked as #1 in his sector.  He used his performance to grab a spot in an emerging area: the internet.  He joined Deutsche Bank which was building out its US team, and he led the IPO of Amazon.  From there, he joined Benchmark as a venture partner, earning billions over the years by betting big and betting right on internet platforms like Uber. 

Did he know he was going to become a billionaire?  Unlikely.

But Gurley knew:

  1. Set huge goals

  2. Move to the right career

  3. Get ownership and take risks.

The first step: believe in yourself enough to set a crazy big destination on your map.

The next step after setting this huge goal is to know the careers and choices that will increase your chance of reaching your $100M goal.  For these, check out my book and blog on How to Make $100M.

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Health: Your $100M Foundation

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How I went from Horse Trainer to #1 Fund Manager in under 5 years.