Why You Should Go for $100M. Moonshot Your Career.

“What’s Your Number?” - asked my Wall Street friend

I’ve never heard this question off Wall Street, even among friends minting millions in hot startups.

But on Wall Street, this question is common.  The number is the amount of money you’d need to say goodbye, adios, arrivaderche, and vamanos to working life and live on what you’ve made.

My reply?

“Don’t we all have enough?”  

“Simply working on Wall Street puts us in the top 1% in the world.  All we’d need to do to have plenty is to cut costs and live within our means.” - I continued…


He looked at me as if I had lost my everloving mind.

Everyone on Wall Street had a number.  Except me.  That ended up being a problem.

While it may seem more evolved to not need a number, anything you do, including making money, turns out better when you have a goal.  

I ran the #1 fund in the world, up 495% in 1999.  I knew how to make big returns. And the money from those returns? That went to someone else.   

I’ve worked for 4 billionaires. I made one boss $24M in one year. He then refused to give me a $5K raise to $150K.  I made my next boss over $150M personally in one trade. 

My take was tiny compared to theirs because I was playing the wrong game. Why?

I didn’t have a Moonshot goal.

Why You Need to Moonshot Your Career

60 years ago, President John F. Kennedy gave his famous “We Choose the Moon” Speech at Rice University.  He rallied the nation to support NASA’s mission to the moon.  He put a stake in the ground by promising to put a man on the moon by the end of the 1960s.

NASA had no idea how they would accomplish this promise.

Worse yet, they didn’t have access to the technology they needed because it didn’t exist.

What happened was the greatest period of rapid technological innovation our nation had seen

The entire US was mobilized behind a single goal.  On the way to that huge goal, surprising technologies needed to be invented.  They included small-form water purification, breathing masks (now used for firefighters), polymer fabrics, cordless tools, rockets, satellites, miniaturization, and long-distance wireless communication.

Rallying behind a huge goal led to many advances.

Is your moonshot $100M?

Here’s my short tale of success without moonshots.

I kept “arriving” and even overshooting my targets.  When I overshot, I had nowhere to go.  

Goals are that powerful.

I never had a goal to run a #1 fund, but the woman who hired me told me that’s what she wanted me to do.  So I figured out how and did it. Soon after that, I joined the #1 hedge fund at the time.  

I thought my aim to work at the #1 hedge fund was lofty.  It was.  But not enough.

That hedge fund boss told me why he hired me:

“I hired you to call the semiconductor cycle correctly.”  

I loved clear goals.  (Too bad I didn’t have a clear moonshot goal for myself.) 

The moment came for that trade.  In late June 2000, I called the top of the semi cycle to the day, and our position changed from $1 billion long to $1 billion short (a $2 billion swing), in a week.  That trade made my boss more than $150M personally.

In 2003, he retired as a billionaire.

He was the fund.  So our company shut down.  I felt lost. 


Having achieved my goal of working at a #1 hedge fund, I was like a sailboat listing in the wind, having already arrived. 

As Vicktor Frankl showed in Man’s Search for Meaning, having a sense of purpose gives us a strong life force. 


Some might argue money and purpose don’t belong in the same sentence. A sense of purpose can mean different things to different people.  It can mean living a spartan life serving others.  Or it can mean a mission to create software enabling anyone to code.  Or it can be making $100M to give generously to charities. Or it can simply mean having a clear goal that gives you purpose. 


If President Kennedy had just said we need to go to the moon, it wouldn’t have set the nation on fire.  What he did was paint it as a race with our biggest enemy, Russia.  That attached purpose to an unattainable goal.  

Combine an audacious goal with a purpose that has meaning to you.

Reach for the moon even if your goal isn’t money.  

Fall 2004, I visited Anky van Grunsven at her barn after her second consecutive Olympic Individual Gold (2000 and 2004).   

For most people, one win would be such a thrill.  That was her aim. Yet, her horse stayed in top form, and they won again. 

She should have been on cloud nine, beating her goals by so much.

Instead, like coming off a sugar high, she was listless. She shared she didn’t know what was next for her.

I saw Salinero, an unassuming 5 year old horse in her barn.  He looked a bit skittish in the stall. As Salinero came out of his shy shell, he gave Anky a feeling of possibility. 

Anky became the only rider to record three successive Olympic wins in the same event.  

It was much harder for her to re-energize herself and think of a new goal vs having set a bigger goal to start.

She should have set seemingly impossible goals and then enjoyed each milestone along the way.


Reach for the moon and land amongst the stars.

There’s only one issue: when you have nothing, how can you dream big?  


How could Anky, a simple girl from the Dutch countryside, know ahead of time that winning two Olympic golds was too small?  She couldn’t.  And you can’t.

That’s why Moonshots work. They are so big, you won’t overshoot. And you don’t have to know everything in advance.

On the way to $100M, you will strive to learn faster, reinvent yourself multiple times, and meet motivated smart people who are aiming at the same goal.  You won’t be alone.  There are 25,000 US households worth more than $100M.  

The MOST important step is to set a huge goal.  Bigger than your wildest dreams.  This big goal, your Moonshot, will keep you pushing forward.

After you set your goal, you may wonder, what else?  This can’t be it?

The next steps (covered in my book and blog) are:

  1. Getting into a high-leverage career early

  2. Moving from employee to owner 

  3. Keeping the accelerator on

It could have been me.  It’s happening to my mentees.  It happened to my friends.

My book shows you the path.

So I have to ask…

Why not you?

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