However long we go back, you've only seen me in one place: the game of business. Dozens of companies scaled to millions a month, and the most recognizable names in business on the client list. My secret ingredient was my mentor, Oren Klaff. Oren is the guy who wrote Pitch Anything, sat on more than two hundred and fifty deals, and raised over two billion dollars. Oren taught me how to pitch. Then he showed me who really gets paid when the pitch works. Together, we play the game of money, and this time we have all the cheat codes. He opened the door for me. I'm holding it for you.
Hear the whole thing from him
Oren's Game of Money, twenty-five minutes. Everything on this page comes out of it.
The board
The game of money has rules, just like every other game. Rule number one: not too early, not too late. Every company that makes it draws the same line, revenue going up and to the right. You want in when that line starts to accelerate and out when it starts to flatten, and you want that to take 18 to 36 months, not 7 to 10 years.
Most people get shown two ways to build wealth. Neither one builds it. The board looks like this.
The middle. Where family offices live, and the only part of the board worth playing.
The players
You've changed seats once already. Out of the paycheck, into the business.
If you've played a video game you know the difference between the player characters and everyone else on the screen. These are the player characters in the game of money, and the rule that runs the whole game is the one you already know: position is everything.
Brings in the revenue and follows the plan.
Paid for time. Owns nothing on the table. Everyone starts here. You did.Paid for workDrives the growth and allocates the investors' capital.
Paid for results. Takes home whatever's left after everyone else gets paid. This is where you are, and you're good at it.Paid for workThe passive capital partner. Buys the security from the banker and expects a return on capital.
Paid for the position. What he makes was decided the day he bought in, by how early and how clean.Paid for the positionSets the rules of the game and coordinates the play. Creates a security, then sells it to the other players.
Paid for the terms. Takes his fee on the way in, whether the company wins or not.Paid for the termsApproves the business plan and the capital raising plans.
Paid for the decision. Five seats decide everything. Three decide if the founder stays.Paid for the decisionEach new character is a new level of wealth. We've unlocked all of the characters in the game.
The game of money is played on a board you have never seen before, by players you are not familiar with, using rules that only insiders understand.
Oren Klaff
What I'm doing with Oren
Start with the default, in numbers. Two hundred grand in the index for ten years has historically come out somewhere around six-eighty. Take ten years of inflation out and it's more like five-forty. That's the plan most people are on, and nobody ever says it out loud to them. It hedges inflation. It doesn't build anything.
Ours is different, and it isn't everybody's. We're here to 4x our money. Not beat an index. Not chase the 100x lottery ticket. Ask yourself how many times you'd have to 4x your money before you could say, if you need me, call the satellite phone. Not many. Three, maybe four. That's the whole idea. You stop looking at a deal and start looking at an endeavor. The deal is move one. A 4x is the target we underwrite to, not a forecast, a projection, or a promise of any return, but that is our target and thesis. Positions miss. We say that out loud because the people who don't are selling something.
I'm from Detroit. This city built more than any city in America and owned less of it, because the work was here and the paper was somewhere else. I'm not spending my life on that side of the line, and neither are the people I bring with me.
How does anyone get in? Relationships. The people who funded these companies early are sitting on enormous positions, many times what they paid, and at some point they want to take some off the table. They can't do it on an exchange, because there isn't one. So they sell quietly, in blocks, to people they already know, at a price the two sides agree on in a room. Nobody lets a stranger into a private company. They let in the guy they've done ten deals with, and he brings a few people through with him. Oren has spent twenty years in those rooms. That's the edge, and it's the only one there is.
The first name was Databricks.
Every company is sitting on twenty years of data it can't actually use.
Customer records, transactions, documents, sensor logs. It exists, but it's scattered across systems that don't talk to each other, in formats AI can't read, with no one in control of who can touch what. Databricks is the software that takes all of that mess, puts it in one place, cleans it, governs it, and makes it usable, so the company can actually run AI on its own data.
The software the world's biggest companies use to organize their data, and build AI on top of it.
It's private, so there's no ticker, no market, and no way in unless someone already at the table lets you in. The last round was full before it was announced. Here's what the price has done in twenty months, straight out of the newspapers.
Sources: company statements, August 2026; Forbes, August 13, 2026; PitchBook, August 14, 2026. Reported figures. Nothing projected.
The other side of those numbers: at a hundred and ninety billion, that's roughly twenty-seven times revenue.
When a 100x story finally gets to you, you're not early. You're the exit.
Oren Klaff
Getting into the room is step one, and it starts with a single deal. Databricks is just one example of the level we are playing at.
Detroit Dealmaker
Now you've seen the other three seats. Stay in yours if you want. Just don't say nobody told you.