Find the rabbit hole 🐇

For anything you've ever dreamed of doing, a community is already obsessing over how to do it cheaper, better, or sooner than you'd think possible.

Not a Reddit thread. Not a single influencer. A full subculture — vocabulary, gurus, internal arguments, beginner mistakes, advanced moves, a paid course worth the money, a free public layer that gets you most of the way.

The skill isn't doing the thing. The skill is finding the people who have already figured out the thing.

Here are four rabbit holes I've gone down, at different depths. Each taught me a version of the same lesson.

Paris and Ireland for the price of taxes

A roundtrip to Paris. Another to Ireland. Flights and hotels both, paid almost entirely in points I'd built up by opening credit cards in the order 10xTravel told me to. The taxes and fees were a rounding error against the retail cost.

That's the gist of travel hacking, and there's a machine behind it — a free Facebook group, a starter course, a community always arguing about transfer partners and sweet spots. The whole thing reads like a foreign language for the first week. By the second, you can run a transfer that nets you a business-class seat to Europe.

The takeaway wasn't "open more credit cards." It was that there's a public, organized body of knowledge about flights, and most people pay full freight because they don't know it exists.

Trading $80k in watches before graduation

Senior year of college, I moved $80,000 worth of watches through my hands. I was not rich. My starting bankroll was embarrassing next to that number. The only thing standing between me and a market I had no business being in was a paid membership to Watch Trading Academy.

WTA taught me to authenticate, to negotiate, and to read a market that looks opaque from outside and structured from inside. Buy under, sell at, fund the next one. The spread is real. Some people run it as a side business. Others run it for a living.

The takeaway was bigger than watches. Real markets run in the open — published prices, active dealers, predictable spreads — and they translate cleanly once you have the vocabulary. The subculture is the translator. Without it, you're staring at a luxury watch wondering how anyone could afford one. With it, you're asking which dealer to call.

Making exotic cars affordable

The math sounded made up the first time I heard it. The car cost more than most people's homes. The guys I knew had been driving cars like it for years. Their explanation: at the right end of the depreciation curve, with the right financing and a willingness to rotate every 18–24 months, the cost of ownership lands closer to a leased luxury sedan than a six-figure purchase.

I haven't pulled this one personally. I've spent real time with people who run the Exotic Car Hacks playbook, and watching them do it taught me the same lesson the first two had: the gap between "I could never afford that" and "I could afford that" is almost always a gap in information, not income.

I trust this one on the strength of who's inside. Small community, real operators, math that holds up when you watch it run.

Multiple passports like Jason Bourne

I haven't run the Nomad Capitalist playbook. I read it.

The premise: tax codes, banking rules, and residency laws assume you operate inside one country. Stop assuming that — second passport, banking in a different jurisdiction, residency in a third — and your financial life changes shape.

I'm not the audience for the answer yet. I am the audience for the question. Most people inherit a single-jurisdiction default and never look up. That's the value of lurking in a subculture you haven't joined. The menu of options widens. You stop accepting defaults you didn't choose.

Finding your own rabbit hole

Notice what these have in common.

From outside, each community looks like something only the rich or lucky can access. From inside, it's a set of moves anyone willing to learn can run. The barrier wasn't money. The barrier was knowing the moves exist.

The answer is almost always the same shape:

1. A paid course or community run by a practitioner, not a guru.
2. A free public layer — newsletter, Facebook group, podcast — that gets you most of the way.
3. A small core of operators doing the thing, not just talking about it.

Find them. Lurk first. Pay once you've confirmed the people inside have receipts, not photos of themselves standing next to a Lamborghini. Then run the playbook.

You'll do this once and feel like you got away with something. You'll do it three times and realize this is just how the world works for people who pay attention.

I'm still hunting for new ones. The less obvious, the more exotic, the better — small communities, real operators, knowledge that hasn't leaked into the mainstream. If you're inside one, send it my way.

There's the version of reality you assume works a certain way, because that's what you've been told. And there's the version you only see once you've peeked behind the curtain, where everything works differently than you could have imagined. That's where the fun lives.