How Much $$ Would I Have If I Wasn’t An Idiot?

Lessons learned the hard way and what I would have done differently.

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Failure > Success?

I talk a lot here about my brilliant (read: mostly other people’s brilliant ideas) for wealth creation. The goal is you grow, I grow, we all grow.

And yet, one of my mentors at Goldman back in the day said it perfectly.

“Never invest in a first time investor. They have to lose before they learn how to win. Do you want that to be your money lost or theirs?”

I have not met one human who is monetarily successful who hasn’t had massive fails, both in investing and more importantly in decision making. So I’m going to break down for you my biggest losses, full transparency. Why?

Because the only way mistakes are truly that, is if you don’t learn from them…


BUT FIRST: A MONEY SUPERPOWER

I’d like to propose a question:

What if life is just a game and we are simply the engineer tasked with coding it in?

What if Making Money Is Simply A Game?

The older I get, the more convinced I am that this is true.

Money, is a game.

Success, is a game.

Here’s the Rub.

Those on high know the game, those of us in the grind were never told. We went to school to learn one thing, to be pawns. We sit on boards to be moved by those who have more use for workers than thinkers. We were taught to recite, to follow the path, to fit into our one step forward, one step back constraints.

I see it this way:

Close your eyes and picture a chess board. If you’ve watched the Queen’s Gambit, you’ll know. Picture yourself laying in bed, a black and white chessboard projected on the ceiling above. It’s harsh squares aligned in tidy rows waiting to be filled with ornately carved pieces. You’re a master here. You can see it all. You play the scenarios over again and again, moving, counter moving until AHA, a victory you hold. You win by skill yes, but also by knowing the rules.

Now imagine that same board in front of you, the king and queen’s stern eyes staring out from ivory-carved players. But here, you see the board but you don’t know the rules. You’re paralyzed. A pawn vs a horse is as meaningless to you as Russian is to a Greek. You, my friend, will never win. Because you don’t even know the name of the game you’re playing.

I hate to tell you, but most of us, we’re the latter. We sit buffeted by pieces taking us out left and right, pounding us as they move to capture the King. Because they know the truth. Those who know the rules and push the limits—why—their bounty is endless. Those who don’t… well.

What’s the point?

How do you keep sheep in line to provide you with wool, with delicious lamb chops? You make them believe they are safer with than without you. They are small, victimized, and the world is a terrifying place full of chance. And they, well THEY, are here to protect and save us. The truth is, they are not here to enable us, to teach us, to pull us up with them. They are here to be our shepherds.

But, Codie, is that so bad? What’s the problem with shepherds?

Shepherds don’t turn sheep into wolves, they tell them what to do, they “protect” them from dangers. But they never set them free.

So, if I had to beseech you one single thing it would be, decide you’re not a pawn, not a sheep. Learn the rules of the money game.

Instead question everything, and turn the rules in your favor.


All the Money I Lost, All the Lesson I Learned

Divorce: A Real Peach

Let’s just say… it' wasn’t a cheap lesson.

If you’ve ever been through one you know the personal and actual expense. It was HARD. It felt like I had to start all over, that I was a massive failure. I remember vividly sitting in my attorney’s office, going back and forth in arbitrage, slowly and meticulously putting a dollar amount on everything we had together. I never tracked the finances much to be fair, I was always working. I sat in awe at the miraculous ways you can spend money. I can still hear him yelling through the wall separating us. I can still remember the tears.

I remember odd moments… his attorney in a short skirt and sky high stilettos clacking up to me to tell me that I better, “Get right in my thinking, honey.” I remember being oddly proud of the way I towered over her in jeans and a t-shirt, smiling while saying, “HONEY, I’ve oddly never been happier to use the words, “You can speak to my attorney.” Despite my false bravado, I was anything but ok. TBF - I’m sure underneath the entire Mac cosmetics store on her cranium, that attorney was a good human. Cough.

But it didn’t really matter, all these ego games. My father said it best,

“There is an exit tax to your freedom.”

He was right. It was worth every penny.

There is no greater value than an incredible partnership and no greater cost than a bad one. That holds true in all partners —> so the lesson, choose wisely. Partnerships are so easy to get into, and $$ to exit.

Ah, if that was the only lesson…

Sayonara Goldman Sachs: Loss $1M to $5M

I was at Goldman Sachs during the financial crisis. It was surreal.

People were getting fired left and right. Boxes permanently sat in our break room for the unlucky few. Managers camped in “the fish tank,” with people coming in to be let go and security guards walking them out. It felt like the world was going to collapse. We walked through protest lines to get into work, my own grandmother called wondering how I could work for the Giant Succubus Squid - a la Rolling Stone (which is funny, now I’m a columnist there).

But remember.. chaos breeds opportunity. When I got there I got stock in the company with each bonus allocation. I can’t remember the exact amount but for my level from analyst to associate let’s assume:

  • I got $150k in stock annually at $82 a share (I was there during one of the biggest downturns in the stock price ever).

  • That stock today would be worth $414,775.

  • So it would have been about a 3x my money (move from $82 to $235 today).

  • Assuming I never got promoted (unlikely) that’s another $150k of stock a year

  • Total 17,560 shares over 10 years

  • Average price of stock still at a 2.5x to todays value ($235)

  • Means I would have had $4,147,750 in GS stock

This path probably would have led to me increasing equity in the company and walking with more like $10Mish. BUT - I led a fast life then. I have a feeling I would have cost adjusted (aka spent more on stupid things) and been miserably materialistic.

I am way too Contrarian (ha), to have worked up the corporate ladder there. I need change and moves, and risks.

Lesson: Buy low, hold long, sell high.

Just because you leave a company doesn’t mean you shouldn’t hold the stock.

Left Senior Role at Financial Firm: Also left lots of $0s

I was doing well at the firm but wanted to grow and do it my way, SURPRISING I KNOW. Thus, I butted heads with the CEO of my company and the managers. Culture fit is REAL and important. Not playing the victim card here, just facts. I was the only woman, I hated golfing, I don’t love drinking, know nothing about fast cars, and I definitely am not into strip clubs or casinos, so basically we had nothing in common. I remember talking to the CEO (whom I respect the sh*t out of, he’s brilliant) but many of his managers are just not my people. He said to me at the time, “You can’t hide passion.” He was right. Time to move on, leaving a LOT of ZEROs on the table.

Lesson: You can become a multi-millionaire while working for someone. What you can’t do is have complete freedom. Often when you are climbing the big company corporate ladder you have to walk from golden handcuffs in order to buy back your freedom.

Robinhood: Steal from the HF Traders - Give to Codie

I had an opportunity to buy into Robinhood on a secondary round at a $700M valuation. It’s now sitting at a cool $11.7B allocation. Le sigh. Let’s break that down…

  • $100k invested

  • $700M valuation to $11.7B valuation or a 1571.43% increase

  • So $1,671,000 left on the table (highly simplified w/o dilution etc)

The lesson here, sometimes don’t fight the trend. In this case I thought the $700M valuation was high AND I don’t like high frequency trading platforms. I think it’s by and large a waste of peoples money.

Lesson: Money isn’t everything.

These are just a few of the stories, I’ve invested in friends companies just because we were buds (generally terrible idea), I’ve gotten excited on ideas and launched them before really understanding the time commitment needed to win (I call this over eager puppy syndrome). I’ve launched companies I HATED running.

The only thing I’ve never done (knock on wood) is lost investors money. All bets were my own dimes. One day that may change if I take a really big hairy risk but for now…

The Moral of The Story:

If' I’ve learned anything... it’s all a game. The only way you truly lose is if you give up, if you stop learning and if you stop trying to get better. There’s no one way to play it. There’s no human who has hit a home run at every at bat (ugh is that a sports reference - this is devolving quickly).

Don’t believe those who only show you their light, there is always a dark side.

So remember, there is always an exit tax for the life you want.

And, don’t worry, it’s pretty awesome on the outside. Money, it’s all around if you want to go get it.

Questions everything and don’t worry about too much about mistakes they’re just exit taxes,

Codie


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