I first came upon Chris Guillebeau nearly 15 years ago. He was promoting travel education to broad audiences, much broader than this website reached at the time. He had an e-book on your credit, and making the most of credit card offers. He traveled to every country in the world. And he was on the cusp of publishing his first book, The Art of Non-Conformity, which was excellent.

He’s written extensively on the new economy, entrepreneurship, and finding personal freedom in an unfree world. He founded the World Domination Summit where thousands of people descended on Portland, bringing their own dreams and schemes and bound together by a desire to live life by their own rules and still live it well (I spoke there twice).

His $100 Startup made the case that people could become entrepreneurs and didn’t need to raise a bunch of money to do it (the book made #6 in its category on the New York Times best-seller list). He championed small-scale success, grinding it out, experimenting and building. He featured my award booking services as a stand-in for the idea that this didn’t even need to be a scary ‘taking the plunge’ but could be something done on the side while you still worked. It was more than a decade ago before this became standard fare, and Chris was a part of making it so.

And Chris Guillebeau is out with his latest book, Gonzo Capitalism: How to Make Money in An Economy That Hates You. It comes with book blurbs from Daymond John, Gretchen Rubin, and Dan Pink.

Now, there’s a certain ‘none of this is real’ element in Guillebeau’s narrative. Early on he posits, Why can’t Venmo or a bank decide everyone has $10,000 more?

And the answer is actually simple: because then Venmo wouldn’t have money to back up those deposits. That works for a little while, because not everyone seeks to withdraw all their money itself. But pretty quickly someone figures out what happened, that Venmo wouldn’t survive a bank run, and suddenly there’s a bank run. That’s what happened to FTX – they looked fine until they weren’t, because the underlying reality ultimately matters.

It certainly seemed in 2021 that the rules of finance and economics no longer applied. As Matt Levine is wont to say, things were valuable in relation to their proximity to Elon Musk. Interest rates were effectively zero, the federal government was airdropping cash and so was the Fed. But there’s been a cost to all of that, and it’s one we’re not yet done paying.

Ultimately we exchange something from ourselves with another person (or business). We provide something they value, and in exchange we get things that we value from other people. That’s intermediated by ‘money’ in a modern economy that’s moved from personal to impersonal exchange. But we ultimately prosper by creating something that others value.

• It’s totally fine to criticize the things that others value, and say that they shouldn’t or that those things ought not be allowed!

• Or to point out ways that in the short run some people prosper through fraud (selling people something and not deliver, convincing them they’ll provide something of value that they don’t, etc) or by ‘gaming’ a system that’s usually set up by government (government usually benefits the powerful even when they’re ostensibly doing things to help people).

• But even there, it’s doing something that people value (bad values, governments) that generates prosperity. I’d sign on to reforming some of these things, but they’re consistent with the model.

But Chris doesn’t need to be right about money as an illusion for the rest of his book to be useful and actionable.

• Everything you can imagine can be bought or sold, with the internet creating enough scale to support the smallest niche. Whatever service you might offer there’s a buyer, and a marketplace (or you can set one up for yourself, with virtually no barriers to entry or gatekeepers anymore).

• While in the $100 startup, you might ask yourself what questions to people ask you about to get a sense for your area of perceived expertise that you might charge for, during the ZIRP era people sold NFTs of monkeys. Those were extreme times, and the NFT craze has passed (at least for now!), but we’ve reached a scale where if we can identify niche subjective value we can get paid for delivering on it.

• You can gamble online, including in prediction markets. You can take more than one job (how much you work at any of them depends on the job, and your level of commitment – I’ve effectively had more than one job for years but am highly committed to each and easily do 80 hour weeks at what I love.

  He talks about how to juggle multiple jobs, avoiding meetings and other techniques, but ultimately in a world where what’s valued is outputs the ethics of this changes – it isn’t actually about what job you’re clock punching into and more about whether you’re delivering the value the job requires.

  I’m less on board where he writes about ‘play to earn’ which was popularized during the crypto craze. This is simply not a long-term business model, though of course if people want to light money on fire offering it then it’s fair play to take the other side of that bet.

• If you want to make money as a livestreamer, or an AI creator, this is a good simple introduction. If you don’t know what Midjourney is, but would like to have computers design art that you sell, buy this book.

At the end of the day, for all of the entertaining and weird (and dare I say crazy!) ways that people make money, Chris points out that they’re usually quite rational and consistent with time-tested business principles – scarcity, moats, subjective value, and ultimately delivering value to other people. The crazy stories are simply an accessible way through which he teaches basic principles for the new economy, whether you want to be a creator or a side hustler.

And he’ll help you ask what it is all even for? Are you really just trying to make as much money as you can, for its own sake, or are you trying to support a certain kind of life or create a certain kind of world where money is a byproduct?

There are places where he’s right – about not always worrying about debt, that it’s a function of the interest rate and relevant alternatives for the money – where the ideas may be underexplained or under-argued. But embedded throughout the book is the idea that you have goals, those goals aren’t just about numbers of a spreadsheet, and if you’re alert there are increasingly ways that never existed before to reach your own subjective goals while charting your own path.

He lightly criticizes the FIRE movement at the end, but for different reasons than I do: “work” is different than it was in the time of Maynard G. Krebs. Or at least it can be. We can create value for others in a way that is personally meaningful to ourselves, too. At least many of us that will consider reading Gonzo Capitalism can.

And I genuinely love the symbolism of the raised fist of revolutionary socialist movements… stuffed with cash in its hand… on the cover of the book.