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The best-selling author is back with a guide to the creative ways that people—including himself—are earning money in this new, strange, tech-driven economy.
Chris Guillebeau has always embraced an unconventional career path. He’s the author of several best-selling books about living and working on your own terms, including Side Hustle, The $100 Startup and The Art of Non-Conformity, and he runs the popular daily podcast “Side Hustle School.” In his new book, Gonzo Capitalism: How to Make Money in An Economy That Hates You (Little, Brown Spark), Guillebeau explores how Millennials and Gen Z are finding new ways to make money with tech tools and platforms. These creators and entrepreneurs include AI artists, TikTok influencers, crypto stakers, blockchain gamers and more—all trying to earn income in a post-pandemic economy that Guillebeau describes as “fast, weird and decentralized.” (Read an excerpt from Gonzo Capitalism.) Below, he shares his thoughts on carrying debt, experiences versus stuff, and a money mindset it took him years to shake.
Spend your money on things that make you happy, and things you find purposeful and meaningful. This was surprisingly difficult for me to learn, because I’d grown up hearing how important it was to delay gratification, limit your spending and so on. For a long time, I was frugal to a fault—I wouldn’t spend small amounts of money even if the purchases would make my life better.
What’s that? Just kidding. I like running, reading, travelling—all typical “down time” activities. That said, I feel very fortunate to be able to do work I really enjoy, so I don’t long to do less of it or feel any pressure to escape.
Pretty much the same thing I’m doing now. Well, almost. At the moment, I’m waiting for a flight that’s been delayed more than an hour. I guess if money were truly no object, things like that would be less of a factor? But flight delays are a small price to pay for the chance to live the way I do, travelling frequently from my home base in Portland, Oregon, and speaking to groups.
This probably isn’t the earliest memory, but here’s what comes to mind: I lived in the Philippines for two years, starting from when I was six. I was with my mom, and my dad was back in the U.S. Every week he’d write me a letter—this was when long-distance calls were expensive—and he included a one-dollar allowance in it.
After the first year, I asked if he could send an extra dollar so I could buy something local to bring back for him. I’m not sure how seven-year-old Chris framed that argument, but it won him over, and I started getting two dollars in the mail every week. Perhaps this was the beginning of my entrepreneurial journey!
Definitely video games, both at the arcade and then for a series of consoles. I had an Atari 2600, then an original NES, and then many others over the years.
Before the entrepreneurial urge kicked in, I had a number of jobs, starting at age 14. The first one was as a dishwasher for a restaurant where I’m fairly certain some illegal things were happening. I think I was paid in cash. The job didn’t last long, and neither did the restaurant.
I started working on my own at age 19, so I’ve never actually had a “real job” as an adult. At first, I resold toys and coffee on eBay. That eventually led to other things, including four years as an aid worker in West Africa and then my quest to visit every country in the world—which I’ve done!
Buy experiences and stuff. If buying a couch makes you happy, buy the couch and be happy! There’s way too much guilt-tripping over the whole minimalism thing.
“All debt is bad.” Ironically, this isn’t just advice I’ve received—I used to offer it to others. I’ve had a change of heart in recent years as I’ve seen how governments and corporations accumulate large amounts of debt without experiencing any serious consequences. Apple, the largest corporation in the world, currently has $100 billion in debt, but it’s also sitting on $200 billion in cash. You might think, wow, why not just pay off the debt? But clearly they know what they’re doing.
There’s more to this argument, of course—I have a whole chapter on it in Gonzo Capitalism. I’m just saying that if you’re in debt, a) you’re not a terrible person, and b) you’re not in the worst position. Pay off and consolidate high-interest debt, but some debt—like a mortgage or car loan—can be a tool to improve your life.
If it’s truly guaranteed to last, I’d choose the weekly or monthly option. But finding something that’s truly guaranteed is hard to come by. Insurance companies and multinational financial corporations go bankrupt. Even governments default on their debts at times. Given that reality, I’d choose the lump sum.
That all they need to do is save and invest like everyone else, and somehow they’ll be better off than most people. One of the things I stress in the book is: “If you want average results, follow an average system.”
The thing is that systems are designed for average. If you’re running a large company, for example, you need to make sure your policies and procedures can accommodate all of your employees. So that’s fine—but as an individual, you may have different needs and preferences.
That’s how it works with personal finance, too. If your goal is to have an average retirement, there are plenty of average retirement plans that will get you there. Which is fine for many people! If you want to become wealthy, however, you’ll need to do something differently. Most of the time, that means you need to take different kinds of risks in terms of investing, side hustling and so on.
I paid $32,000 and spent two years studying for a piece of paper that stated I’d earned a graduate degree in international studies. While I’m grateful for parts of the experience, as well as the relationships I formed during that time, overall I’m pretty sure it wasn’t the best investment. And it wasn’t just me—many of the students in my cohort who had a more direct connection between the degree and their careers also seemed dissatisfied in the end.
In the personal finance world, value means enjoyment. Did I enjoy that purchase? When I think about the amount of money I traded for it, does it seem like a fair trade? If so, great! I really value my time and am a big fan of “buying” it back whenever possible. I work on my laptop in the back of Ubers, I won’t call about small refunds I’m due just because I hate talking on the phone, and so on.
Other people will make different choices, and that’s fine. The important point is to know yourself and understand what matters to you.
I bought my first round-the-world plane ticket after moving back from Africa. It cost $5,000 and was a wonderful investment. I used it to visit more than 15 countries over the course of several months, and it set many other things into motion.
The delays for this flight have continued—we’re now at the end of hour two. I often fly economy, especially for short flights, but on this one I’m very glad I spent more for first class. Having a modest amount of extra space goes a long way when you’re sitting with 200 other people.
I really liked Money: A Love Story by Kate Northrup. And I like anything by Jill Schlesinger. Otherwise, I don’t read a lot in the business or personal finance genres. Since that’s what I write about, I prefer to read more fiction and narrative non-fiction.
Now that Apple Pay is much more ubiquitous, I don’t always carry a wallet! That was a big shift after carrying one for decades. For the times when I do have a wallet on me, I downsized to a very thin one that just has my driver’s license, three credit cards and $100 in cash, tucked away for the occasional time that cash is required.
I love this question and had to think about it for a long time. I’m not anti-possessions, and I think it’s totally OK to “buy stuff” in addition to valuing experiences. But I can’t think of any possessions that feel particularly special. Maybe I should buy one of those cold plunge tubs everyone’s getting.
In Gonzo Capitalism, I wrote a lot about the play-to-earn movement, which is basically blockchain video games where you can earn real money. I really got into it during the pandemic. Much of the sector took a big hit with the rest of the crypto crash, but some games are still thriving. I’d like to earn $100,000 a year from online gaming, without it taking so much time away from my “real” career. I think it will happen.
I don’t have a spreadsheet-style budget anymore, but I try to identify major priorities at the end of every year, then make spending decisions for the next year accordingly.
Some of both.
I assume this is for a car? I don’t own or lease one. Driving stresses me out, so I think it’s better for everyone that I usually stick with Uber, Lyft or public transit.
Team Rent all the way. Don’t believe the hype that home ownership is for everyone. If it’s good for you as an existing home owner, that’s cool. Just don’t pretend it’s the right choice universally, because it’s not.
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