0:00
/
Preview

Running a One-Man Hedge Fund

Half Year Performance + How I'm Allocating Another $100k (Every Trade for Premium members)

I Run a One-Man Hedge Fund

No investors, no office, no payroll — just capital, a handful of option structures, and an old idea of Ed Thorp's. Here is the whole system, the live trades, and — for members — the exact orders I'm placing this week.

There is a particular kind of freedom in answering to no one.

I don’t run a hedge fund in the regulatory sense; there are no limited partners, no capital calls, no quarterly letter I owe to anyone but myself and the readers who choose to look over my shoulder. It is a book of my own capital, operated from wherever I happen to be standing, built for a single purpose: to generate cash flow that does not depend on a post code.

So why would anyone want to do that? Because the alternative, for me, had stopped making sense. I came out of COVID having spent years building private businesses and rolling them up, and the world I returned to was not the one I had left. The effort-to-reward had quietly inverted. More to the point, none of it travelled. You cannot fold a service business into a carry-on. You cannot take real estate through customs. I wanted the thing that an in-person enterprise can never give you — the ability to deploy capital, and harvest income from it, from anywhere — and I set about building it deliberately. The first sketches of this idea were drawn in Panama in 2023. This publication is the documentation of where they led.

The Early Days - Hotel Sortis. Panamá City. 2023

A necessary word before any of the rest. Nothing here is advice. I share only real trades I have on or am putting on, alongside the occasional theoretical deployment, for the record. Past performance guarantees nothing. There is no guarantee of any performance whatsoever. This is a journal, not a tip sheet.

Where the book stands

Year-to-date, the number that matters most to me is twenty-two percent — those are the realised gains in 6 months. Realised = banked, already accounted for. Not a mark, not a hope: cash. That comfortably covers the income the book is supposed to throw off, and it leaves a discussion for another day about the returns on the capital I actually put down versus the capital I get to use.

That distinction is the whole game. An insurance company makes its money on the float — on money that is not, strictly speaking, theirs. I have no desire to run a property-and-casualty insurer. I have every desire to borrow its philosophy and apply it to the one asset class most people refuse to treat as an asset class at all: leverage itself, handled with respect.

The engine is sixty years old

Keeping it as simple as I can, the core of what I do is an adaptation of Ed Thorp’s warrant-hedging system. If you’ve read Beat the Market — I keep a first edition — you’ll know the shape of it. Thorp used the mathematical relationship between a warrant and its underlying stock to construct positions that locked in something close to a guaranteed profit; market-neutral, indifferent to whether the index went up or down. It worked beautifully through the 1970s, a decade in which the stock market did poorly and inflation did as it pleased.

I believe that past may be somewhat prologue. So I have spent a long time sitting with Thorp’s original idea and asking how a single operator, today, with a modern options chain instead of a warrant book, might express the same thing. The answer is Machina Capitalis — a capital machine, rebuilt out of option structures.

Among my prized possessions: Two first edition Originals from the master Ed Thorp.

3 Very Important Tactics

There are six structures I run. The three that carry the weight are the hedged longs — which is a dignified way of saying deep in-the-money covered calls, or buy-writes.

The mechanics are unglamorous, which is precisely the point. I own an asset I want to own. I write a call against it, lately quite deep in the money. In exchange I receive a fat premium that gives me a built-in downside cushion and a defined, knowable maximum upside. I can set the trade for six months, twelve, sometimes twenty-four. I know my worst case and my best case the day I enter. I have come, over time, to prefer this kind of elegant simplicity to almost anything else — because it is operationally efficient, and because, when done with patience it pays twenty, twenty-five, thirty percent implied returns simply for entering. You get paid to show up. This is my version of Thorp’s basic system.
It’s not as easy as it sounds - I need to adjust the ratio of long:short exposure as the trade unfolds if I wish to remain delta-neutral.

The second structure is the cash-secured put, and I do it the unfashionable way. I sell a long-dated, out-of-the-money put on a name I would be glad to own, collect the premium up front, and take the stock at a discount only if it ever reaches my strike. I do not sell weekly puts and roll them month over month. That sounds wonderful in a thread and works for almost no one over a full cycle. Recently I closed some Fermi puts I’d sold fifty-nine days earlier — for roughly 10% profit booked, which annualises near sixty. It does not always go that way. But selling insurance, long-dated and out of the money, contributes quietly and durably; the zero-day-to-expiration circus is fraught with peril.

The third is the leverage dial — the synthetic, or poor man’s, covered call. Instead of buying the stock outright and writing against it, I buy a deep in-the-money LEAP, the modern descendant of Thorp’s warrant, for a fraction of the capital, and sell a nearer-dated call against that. Same exposure as the basic system, more moving parts, a sliver of the cash. When it works the return on invested capital is something to behold. But leverage cuts both ways, and this is not a thing to pick up and start doing on any given Sunday.

The system in action

I am a practitioner, not a theorist, and the internet is full of theorists. So, three real trades then.

Examples from the vault

The basic system: a LandBridge buy-write. I bought the stock around $60.42 and wrote an in-the-money call at $55, for which I was paid $14.47. That locks in roughly thirty percent annualised if I’m assigned, with a twenty-four percent cushion — the stock has to fall almost a quarter before I lose a dollar. Upside is capped, but that’s the concern of the long term investment portfolios covered in The Royalty King, not an operating business.

The short put: the Fermi position above. A $2.50 strike sold into a stock trading near $5, when the volatility premium was, frankly, absurd. Ten percent returned in fifty-nine days, closed.

The leverage dial: a synthetic covered call where, rather than pay $12,500 to control a hundred shares of a $125 stock, I controlled the same notional for $3,710, sold a call just out of the money against it, and closed both legs a week later for roughly 4.85% on the capital committed. A week. That is the upside of leverage.

How Much Is Needed For Freedom? A $100K Prototype.

Before scaling anything, I ask a small question: what can a single $100,000 of working capital reasonably underwrite, and does it move the needle? If I can earn thirty percent annualised (22% so far in 2026) on $100k, that’s $30,000 and approximately equal to the median annual wage in Europe. Set against a US median wage near $60k, it implies something quietly radical; two hundred thousand dollars of working capital, run this way and if the performance holds, equals/replaces a median income. No guarantees attach to that sentence. But as a thought experiment, it is the entire reason I built the machine.


The free portion ends here.

Below the line, premium members of Machina Capitalis get the rest of this issue: the exact list of names I’m underwriting over the next six months, the full order entry — stock, short strike, and the asking price I’m posting the calls at — the contract counts behind each, the blended math (≈35% downside protection across the book, close to 25% over six months, ~50% annualised if the orders fill), and how I weighted it all between the names.

If you want the order book, it’s one click away. If not, I’ll catch you in the next issue.

The basic system more than funded this adventure — no staff = more hiking time. Glenorchy New Zealand. 2024

This post is for paid subscribers