The Engine and The Network

There was a guy who worked in my building on Wall St but at a different firm, let’s call him Sal.

Sal was a Managing Director in the structured products group, which in the mid-2000s was like being the guy who owned the only oxygen concession on Mount Everest. He had a machine in his corner of the building that printed money.

Or rather, it took things that were not quite money, chopped them up into things that were even less like money, and then, through the dark magic of financial alchemy, sold them to Germans and Swiss as if they were gold bars. It was a beautiful thing to behold, in the way a black hole is beautiful. It just worked.

Sal’s entire life was a single, glorious engine. He’d arrive at 6:00 AM, his face already a mask of grim determination, and plug himself into the Bloomberg terminal like a pilot jacking into a fighter jet. The engine was the bank. The fuel was unlimited black coffee, his preternatural ability to smell fear, and a global demand for mortgage-backed securities that seemed as infinite as the heavens. The exhaust was a plume of cash so thick it distorted reality around him. He had the seven-figure bonus, the nine-bedroom house in Greenwich that looked like a resort hotel, the wife who chaired charities for endangered tadpoles. He had a single, high-torque, gas-guzzling V-12 engine of wealth, and he kept his foot pressed firmly to the floor.

Sal owned an island in the Caribbean and 6 properties in the United States.

Many worshipped Sal, money is their religion after all. Most wanted to be Sal. We saw his engine and thought, I need to get me one of those.

Then came 2008.

The infinite demand for his particular brand of structured nonsense turned out to be, shall we say, finite.

The machine didn’t just sputter… it exploded.

One day Sal was the master of the universe; the next he was a guy with a suddenly very quiet phone and a portfolio of assets that had the approximate value of confetti. He was wiped out. Not just financially, but spiritually. He had only ever known how to operate this one magnificent engine, and when it seized up, he didn’t have a bicycle, a skateboard, or even a decent pair of walking shoes to fall back on. The last I heard, he was selling “alternative asset advisory services” which is Wall Street for unemployed.

Sal’s ghost haunts me.

It’s the ghost that pushed me out of that world and into this one, a world of exposed brick, kombucha on tap, and the quiet hum of a thousand different engines, all running at once.

I traded a corner office in Midtown for a shared desk in a Flatiron WeWork, and it was the best trade I ever made. Because I learned the secret that they don’t teach you in business school, the one Sal never figured out: The key to building real, unshakable wealth isn’t owning one giant engine. It’s having a whole garage full of them.

From V-12 to a Portfolio of Go-Karts

My life as an investment banker was a study in monolithic dependence. My salary, my bonus, my identity… it all came from one source. The bank.

I wasn’t building my own wealth; I was a compensated cog in their machine. They owned the engine; I was just allowed to siphon off some of the fuel as a reward for keeping it running.

When I left, I didn’t have the capital to build another V-12.

So I started with go-karts.

My primary engine now is a smaller one, but I own the vehicle outright and I can drive it where I want. I am a single family office. I spend my days listening to pitches from twenty-five-year-olds who are convinced they can disrupt the global supply chain for everything using the blockchain. Ninety-nine out of a hundred are certifiably insane.

But one of them… one of them might just be right.

My job is to find that one. This engine doesn’t pay a salary; it’s a series of lottery tickets. But if one of them hits, it pays for all the losers, and then some.

But you can’t live on lottery tickets.

So, I built other, smaller engines.

Engine number two is my advisory business. It turns out that a lot of those disrupting founders don’t know how to read a balance sheet. They can write elegant code, but they think a term sheet is what you put over a mattress. I speak their language, but I also speak the language of the people with the money. I’m a translator. For a slice of equity and a retainer I’ll help a brilliant young company build a financial model that doesn’t look like it was drawn by a child in crayon. I’ll sit on their board and be the designated adult in the room. This engine is a steady-droning generator. It won’t make me rich, but it keeps the lights on.

Engine number three is what I call “The Weird Stuff” I co-own a piece of a company that’s building a levitating rotor that could solve our energy storage problems one day. I have a small investment in a startup that uses AI to write marketing copy, which feels both brilliant and vaguely terrifying. I have another investment into an AI play, but this one is focused on accounting and financial operations. I write a paid newsletter breaking down technology trends for people who want to sound smart at cocktail parties. Each of these is a tiny, sputtering motor. A little outboard on the back of the boat. They don't generate much power on their own. But they do two things: they generate a little bit of cash, and more importantly, they generate information. They are my feelers, my outposts in different corners of the economy.

This is the portfolio approach to a career. The goal isn’t just to get rich; it’s to become un-ruinable. To become the anti-Sal.

If my investments have a bad year, the advisory work and the weird stuff carry me through. If a new technology upends one of my companies, the AI copywriter might be taking off. It’s a web of interconnected, mutually reinforcing systems. It’s messy and chaotic and requires a staggering amount of context-switching. But it’s mine. I own the whole garage.

The Human API

On Wall Street, your network is a ladder. It’s hierarchical and transactional.

You suck up to the guy above you and kick down at the guy below you. A relationship is a means to an end: a deal, a bonus, a promotion. The value of a person is what they can do for you, right now.

In the tech world, your network is a web. It’s decentralized, chaotic, and built on a strange currency of favors and information. To survive, you have to stop thinking of people as rungs on a ladder and start thinking of them as nodes in a system. You have to become a human API, an Application Programming Interface. Your job is to connect disparate systems.

My old network was a list of names in a Rolodex. My new network is a living, breathing organism. It includes people like “The Connector” a woman who seems to have had coffee with every single person in the tri-state area and whose entire value lies in her ability to make introductions. It includes “The Deep Thinker” a brilliant but painfully awkward coder who is building something that could change the world, but who you can only access if you first prove you’ve read the same obscure sci-fi novels he has. And it includes “The Money” the newly-minted founder who just sold his company for a billion dollars and now wants to reinvest, but doesn’t have the time to listen to a thousand pitches about paperclips.

These people don’t trade on transaction.

They trade on trust.

The rules are different here.

You give before you get. You make an introduction for someone without any expectation of a return. You share information freely: a tip about a new market, a warning about a difficult investor. You are playing a long, infinite game.

The junior engineer you help today might be the founder of the next Google in five years, and she will remember that you treated her like a human being.

Just last month, this human API fired on all cylinders. A casual conversation with a UX designer I know through my “weird stuff” portfolio (Engine 3) led to a discussion about the abysmal state of software for managing clinical trials. “You know who you should talk to?” she said.

(I love when she says that)

She introduced me to a former emergency room nurse who had been sketching out a solution on nights and weekends (Network). I spent a month talking to her, digging into the market, and using my "Wall Street translator" skills to turn her sketches into a compelling financial model (Engine 2). I then took that model to the family offices I co-invest with (Network) and led a seed round investment from my own family office (Engine 1).

The whole sequence was a symphony of interlocking parts. Not a single, linear transaction, but a cascade of trust and information flowing through the web.

That’s a kind of power that Sal, with his single engine and his transactional ladder, could never have understood.

The Gospel of the Grind

Here’s the final, and most important, piece of the puzzle. You can have all the engines and the best network in the world, but if you don’t have a reason to get out of bed in the morning, you will eventually run out of fuel. The money can’t be the mission. It’s a byproduct of the mission.

My mission isn’t just to make money. My mission is to find and fund the people who are building the next New York. For a century, this city’s identity was finance. The skyscrapers, the culture, the power… it was all built on the engine of Wall Street. But that engine is old and sputtering. The future of this city, and the world, is being built in the chaotic, creative, and terrifyingly ambitious world of technology. I want to have a front-row seat. I want to be a part of it. That’s the gospel that gets me through the deals that fall apart at the last minute, the founders who ghost me, and the investments that go to zero.

And pursuing that mission requires a set of personal qualities that are far more important than a Wharton MBA.

First is consistency. It’s the unglamorous, un-Instagrammable work of showing up, every single day. Answering the emails. Taking the meetings. Doing the reading. Momentum in this world is built brick by boring brick.

Second is intensity. Not the chest-pounding, Red Bull-fueled intensity of a trading floor, but a deep, focused, intellectual intensity. It’s the ability to become the fifth-leading expert in the world on a niche enterprise SaaS product for three weeks, and then forget all of it and move on to the next thing.

Third is resilience. You have to be able to take a punch. I had an investment in a company that I was sure was the next big thing. Great team, great product, huge market. It failed spectacularly. Ran out of money and plagued by co-founder drama. My entire investment was vaporized. In the old world, a failure like that was something to be hidden, a source of shame. In this world, it’s a data point. I wrote a long post-mortem for my partners explaining exactly what went wrong and what I learned from it. My failure became a lesson for the entire network. You have to be able to treat failure not as an indictment, but as tuition.

Finally, there’s resourcefulness. When you’re a smaller investor, there’s no IT department. There’s no legal team down the hall. There’s no army of analysts to build your models. There is you, your laptop, and your ability to figure shit out. You become a master of the LLM back-and-forth conversation, of the duct-tape workaround, of the favor-based economy. You have to be relentlessly, creatively resourceful.

The New Rich

I sometimes see guys like Sal on the Metro-North when I pop up to CT from NYC.

They look older, grayer. They still wear the uniform. Brioni suit, the Ferragamo loafers… but it hangs on them differently now, like a costume from a play that closed a decade ago. They have the haunted look of men who were promised the world and were given only a single, fragile engine.

I don’t have a house in Greenwich. I live in a two-bedroom apartment in Manhattan. My net worth on paper is probably 1/5th compared to what Sal’s was at his peak. But I feel like the richest man in the world. My wealth isn’t a number in a bank account. It’s the robust, anti-fragile, interconnected system I’ve built around myself. It's the multiplicity of my engines. It's the strength of my network. It's the clarity of my mission.

From a rooftop bar in NYC, you can look across the way at the glittering skyline of Manhattan. It’s a monument to a century of wealth built on the old model. But the view from here is better. Because you’re not just looking at the past. You’re looking at the people all around you, hunched over their laptops, sketching on napkins, building the thousand little engines that will power the future.

And being a small part of that creates the kind of wealth they can never take away from you.

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I started Wealth Systems in 2023 to share the systems, technology, and mindsets that I encountered on Wall Street. I am a Wall St banker became ₿itcoin nerd, ML engineer & family office investor.

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