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The New Rules of Money

Before we had the title GONZO CAPITALISM, we thought about calling my new book The New Rules of Money. Overall, Gonzo Capitalism is much better—the book is about more than personal finance, and no one likes to read about rules. 🙂

Still, I had the working title for a while because one of my goals was to challenge the orthodoxy of the personal finance world. For decades, finance experts have been saying almost the same things over and over.

Every once in a while, someone comes along and offers stylistic updates to the conventional wisdom, but the core advice remains much the same. This is true even as the rest of the world changes, and even as large groups of people want to live differently.

With that in mind, in the book I offer eight new rules of money. I’ll share four of them with you here in this post. (This is just a small selection of one chapter. The whole book is 250 pages. As they say, pre-order now!)

1. Stop Trying to Take It with You

No one will tell you that their primary goal in life is to save up as much money as possible—yet many people live this way. With this mindset, accumulating money becomes the goal itself, not the means to something else.

An entire industry has been built around the idea that your ultimate mission in life is to end up with the most money—as though life were a game of Monopoly. Just think about how crazy it is: unless you’re keeping a stash of cash under your mattress, whatever money you possess is just a number in a computer—it has no objective value until the moment you spend it. Yet this philosophy has millions of adherents who base all of their big decisions on it.

Ask yourself: If you had all the money you could ever need and more, what would you do? For many people fortunate enough to achieve this goal, the answer lies in their behavior: they simply redirect their time and talents into trying to get more money.

Whenever you’re feeling stressed out about money, remember that it isn’t the purpose of life. Life is about relationships, experiences, growth, happiness, pain, and everything else that happens along the way.

I know what someone out there is thinking: Well, that’s easy to say for people who already have money. And yes, it’s mostly true that privilege and wealth make things easier. We don’t all begin at the same starting line.

But just consider another truth: Some of the wealthiest, most privileged people are also constantly stressed about money. They may own multiple homes and take lots of fancy vacations, but they are no less miserable than anyone else.

So while there’s nothing wrong with wanting more money— in fact, I think having more money is generally good—it’s important to keep it in perspective.

Conveniently, this brings us to rule number two.

2. Avoid the Frugality Trap (or, Buy Experiences AND Stuff )

If you’ve ever sought out advice on how to save money, you’ve likely come across the mantra Buy experiences, not stuff. The idea is that “stuff” (material possessions) provides less of a return on investment in terms of happiness than “experiences” do.

This aphorism is long overdue for a takedown. Not because it’s categorically false, but because, like many memes or bumper stickers, it’s just a bit too lacking in nuance. Sure, experiences can deliver more happiness than stuff. But the opposite can also be true. And if you’ve ever felt guilty when buying stuff that makes you happy, it’s probably the fault of this philosophy.

Long ago I used to worry a lot about spending money, even when it was trivial amounts. It made me feel anxious for reasons that lacked any rationality—I wasn’t going to go broke if I paid for a sandwich, but that’s what it felt like.

Could I have saved a few dollars by making my lunch at home? Maybe so. All I know is, my life got a lot better when I stopped questioning every little purchase I made.

Yeah, it’s cool to see the sunset—but also, sunsets are free, so there’s no trade‐off between seeing them and not seeing them. There’s also nothing wrong with wanting to buy a new couch.

3. Learn to Take Asymmetrical Risks

Learning to take the right kinds of risks can serve you well throughout life. Some of the best risks are asymmetrical, which means the probability of something going catastrophically wrong is much smaller than the potential for gain.

The classic example is investing in stock options. With options, you bet on the price of a security for a predetermined future date. If you don’t hit your target, you lose the opportunity to purchase at that low price—but that’s all. You can never lose more than you paid. The potential gain, however, is unlimited. If the security rises (or falls, depending on the bet) 500 percent, your profit is 500 percent.

Just to be clear: I’m not saying you should become a day trader. Actively trading stock options is not for the faint of heart — but there are two larger principles here: The right kinds of risks are worth taking, and inaction can sometimes be riskier than the risk itself.

Put another way, if you don’t buy the lottery ticket, your odds of winning are zero.

This principle applies well beyond financial trading. Where else can we find asymmetrical risk? Let’s take a career example. When Damion Taylor was laid off from his job in social media management, he decided to try his hand at the freelance life.

But rather than post his services on a platform like Fiverr, which is essentially a giant marketplace for freelancers, he had a different idea. He logged on to LinkedIn and started contacting companies that had posted job listings in search of full‐time social media managers, even though Taylor wanted to work strictly on a contract basis.

His pitch was unconventional, but compelling: “Hey, I know you’re looking to hire a permanent employee, but I can do this task for you on an outsourced basis for much less money.” Most companies he contacted ignored him, but some listened and gave him the gig. He now earns $10,000 a month from a roster of clients that has grown to the point where he has to turn down work so he doesn’t burn out.

Damion’s method was a classic asymmetrical bet, with limited downside and unlimited potential. So now it’s your turn: learn to identify activities that have little or no risk and the potential for 10x gains.

Ask yourself: “What could I try that wouldn’t be that bad if it failed, but would be amazing if it worked?”

4. Stop Worrying About Debt

Millions of people live in a state of anxiety over consumer debt and student loans—and who can blame them, given how many financial gurus send the message that all debt is bad, and that the ultimate goal is to live debt‐free? For many people, however, this goal falls into the category of “nice work if you can get it.”

What if, instead of worrying about debt, you sought to put off repaying it for as long as possible? That’s what governments and other large institutions do, after all: they just keep borrowing lots of money, over and over, without worrying about the consequences. So why shouldn’t you?

Some of the world’s wealthiest individuals routinely take on debt. Even Mark Zuckerberg, worth approximately $110 billion at the time, took out a mortgage for his $6‐million house. Larry Ellison, whose net worth hovers around $103 billion, uses a portfolio line of credit to borrow on his shares in Oracle. Depending on which media source you read, his line of credit is anywhere from $4 to $11 billion. He then uses this credit line to pay for, well, pretty much anything he wants.

It’s true that Larry’s living expenses are different from yours or mine: he has to cover expenses on five homes in Malibu, at least one James Bond villain–style yacht, and the sixth‐largest island in Hawaii—which he now owns. The point is, Mark and Larry take on debt because they know they can earn more with their money in the market than they could if that money was tied up in “home equity.” And this isn’t just true for billionaires — it’s also true for the rest of us.

So instead of stressing out over how quickly you can pay off debt, consider how you could put that money to work for yourself instead. Pay down or consolidate high‐interest debt, sure, but some debt can be a tool to improve your life, not a burden that leaves you feeling miserable.


As I said, I want to challenge conventional wisdom and the personal finance orthodoxy with this new book. I’m excited to share it with you in just two weeks. 🙂

Pre-order GONZO CAPITALISM and get a free audio series. Thanks for your support!