However long we go back, you've only seen me in one place: the game of business. Six years ago I picked Oren Klaff to learn from. He wrote Pitch Anything, sat on more than two hundred and fifty deals, and raised over two billion dollars in capital. Everything I've done since has his fingerprints on it. He taught me early: ask for money and you get an opinion. Ask for an opinion and you get money. So this summer I asked him for one. He told me why my idea was terrible. Then he told me the truth: I was done with the game of business. Not because I'd lost. Because I'd run out of board. He wasn't offering me a seat at his table. He was offering to build one with me. Which is where you come in. He opened the door for me. I'm holding it for you.
The game of money
Oren's rule: positioning is everything.
The catch is that it does not run on the rules of the game of business. He calls it upside-down land.
New character, new world. And each new world means much bigger wins.
Paid for time. Trades hours for a salary, owns nothing on the table, and finds out what the table was worth by reading about it later. Everyone starts here. You did.
Paid for results, in a game where the number in the press is never the number in your account. "I sold my company for forty million" can mean twenty, or five, or less than zero once the structure unwinds. Oren's picture of the trap: fifty million in revenue, forty in expenses, ten in income, a little debt, two in taxes, eight hundred thousand left, while your best salesperson takes home four. This is where you are, and you're good at it.
Paid for the position. Owns the paper, doesn't run the company, and gets paid in proportion to how early and how clean he got in. Two rules come with the seat. Every proof point you wait for costs you entry price, because time moves on. And the paper is only as good as the person, because you cannot sue a small business. Which is why the game starts with people.
Paid for structure. Finds the company, writes the terms, builds the deal, and collects whether or not it works. Oren's first rule of banker fees: hide the fees. His second: moving money is easier than moving dirt. In every deal you get structure or terms, never both, and the banker is the one who knows the difference.
Paid for control. Five seats. You give up two, they flip the independent, three to two, they terminate you, four to one. You keep a title: director of marketing ideas, work from home, no direct reports. The board never appears in the pitch. It always appears at the exit.
Players one and two are the game of business. It's real, it's hard, and winning it is what made you the kind of person who can read this page. Now look at the right-hand column. Two of the five get paid for work. Three get paid for the seat. They don't work harder than you. They sit in a different seat.
You already know what a change of seat does, because you made one. It's simple. Think about your life as an employee. Think about your life as a CEO. Position is everything.
Now run that same jump one more time. The CEO builds the thing and takes home whatever is left after everyone else is paid. The investor owns the paper and gets paid on the whole thing, not the leftovers. The banker writes the terms and collects whether it works or not. The board decides the order everyone gets paid in. Same company, same year. The seat decides the outcome again, and by more than the first jump did.
Here's why the second jump feels different from the first. When you went from employee to CEO, the rules were written down. Books, mentors, a thousand podcasts. The jump into seats three, four, and five has no manual, because the people who know the rules get paid by you not knowing them.
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 the jump actually is
The first thing Oren corrected in me was the word I kept using. I was talking about companies. He stopped me. The investor game is the game of securities.
There's a hierarchy, and where you look on it tells everyone at the table how long you've been playing. Product. Company. Security. Each one is a different question, and only one of them is the investor's.
Is it good? Do people want it? That's a customer's question. You already know how to answer it, which is exactly why it's the trap. Where you're strongest is where you're most likely to stop looking.
Revenue, margin, management, the competition. The operator's question, and a better one. It's still the question you'd ask before buying the business. You're not buying the business.
The mature investor asks two things and stops. Is this a good piece of paper? And can I trade it? Who wrote it, how it's built, what it's worth to the next buyer, and how I get out. Everything else is homework somebody should already have done.
Oren's line for it: good products are not necessarily good companies, and good companies are not necessarily good investments. He brought a deal to a group once and they came back confused. We don't understand the product. It was an industrial thermostat. Who cares. When he takes the same deal to bankers, nobody asks what it does. They ask what the structure is, who's managing it, and what the timeline looks like. It's a financial product. Your ownership is a piece of paper, and the paper is what you're buying.
Think of a graded Jordan rookie card. Everything about Jordan, the flu game, the seventy-two wins, the shoes, gets compressed into a grade, a number, a year, and a condition, in a market with a set price and buyers waiting. You don't need to know basketball to buy it. You need to know what a grade nine is. The grading is the work.
So here's the definition, word for word from the call. An investor turns money into assets that can be sold for more than they were bought, with liquidity. Do that and you're an investor. Do anything else and you're a customer with a bigger check.
Which means the jump looks like less, not more. Less time on the product, because you can't help understanding it anyway. No time falling in love with the company. All of your time on the paper: the people who wrote it, the way it's built, and the door out. That's the whole discipline.
Is this a good security, and can I trade it?
Oren Klaff
What I'm doing with Oren
In August, Oren and I opened a desk. We pick from the thirty most valuable private companies in America, the ones you read about every week and can't buy a share of. One position at a time, with a small group of people we actually know. Then we do it again.
Why only those? Because there are three places to buy a company, and two of them are rigged against you. Early, you're betting the thing exists. Two hundred ninety-nine of three hundred die, and even the pros can't pick the one. Public, everyone gets the same information the same second, so you're riding the swell, and by the time a story reaches you, you're the exit. In between is a window. The company has already won, real revenue, real customers, but it hasn't listed, so there's no perfect information and no public price. That's the only place where homework beats a payroll. The risk stops being does it exist and becomes did I pay the right price. And price is the one risk you can actually underwrite.
That group doesn't scale past the number of people I can know.
Here's our thesis, and it isn't everybody's. We're here to 3x our money. Not beat an index. Not chase the 100x lottery ticket. A 3x, with the same people, then do it again. Ask yourself how many times you'd have to 3x your money before you could say, if you need me, call the satellite phone. Not many. That's the whole idea. You stop looking at a deal and start looking at an endeavor. The deal is turn one. A 3x is the target we underwrite to, not a forecast, a projection, or a promise of any return, but that is our target and thesis.
The names come from Oren's partner Jim, a career venture capitalist who kept saying things about AI in private that hit the cover of the Wall Street Journal a few weeks later. Eleven times in a row. So the desk invests along his insights and asks two questions of every name. Can we afford it, and can we get in.
Getting in is the whole job. The round is full before you hear it exists, the minimum bite starts at fifty million dollars, and there's no public price because there's no market. It's a people business.
The first company the desk underwrote this year was Databricks, the data layer under most corporate AI. Here's the line forming, straight from the newspapers.
Sources: company announcements; Forbes and TechCrunch, 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
Oren is not the guy who wrote the book. He's the guy who did the deals the book is about. I'm his partner on the desk, and this page is what I'm learning next to him.
Before you reach out
No pitch · no deck · a phone call
Twenty minutes by phone. I'll tell you what I'm learning, you tell me what you think of it, and we'll both know whether this is a game you want to spend more time in. If it isn't, you'll hear it from me first.
Worth a conversationOr reply to any Thursday note