Wealthsimple is a whole new kind of investing service. This is the latest installment of our recurring series “Money Diaries,” where we ask interesting people to open up about the role money has played in their lives.

OK. Best financial move I ever made. In 2008, when I was a journalist covering this world, I was like a man possessed about the stock market. I was telling everyone I knew, “This thing is going to come down; this thing is going to come down; this thing is going to come down.” And in fact, I actually pulled my money out of the stock market at a certain point before the huge crash. And then I put it back in at some point after the bottom. I didn’t time it perfectly, but I timed it well enough to preserve a lot of money that would have been lost. So then I fancied myself smart, and I was like, I know how to do this. And so I bought a couple of stocks. I remember thinking, It’s a no brainer: Visa’s gonna go through the roof. Everybody’s gonna be buying stuff online, and of course they’re going to use Visa. And then Visa tanked. And it was just very clear that I had gotten lucky, and I have no idea what I’m doing.

But I just took out that money in 2008, and I put it all into government bonds. (Side story: I put it in government bonds because at the time I wanted it to be in something real, and I thought these bonds were essentially dollars. And then when I started Planet Money for NPR in the States, I learned about what money actually is, and I learned that money is not real, either. Anyway.) I mean, it’s not like it made me a fortune or anything. All it did was preserve, like, a month of nursing home bills when I retire. Well, maybe it’s a couple of days of nursing home bills given the way health-care costs are rising.

If you think you’re smarter than the market. You’re wrong.

But that’s actually the opposite of the lesson I learned about what to do with your money when I was a journalist. The single best piece of investment advice I’ve ever gotten is really simple: Nobody knows anything. If you think you’re smarter than the market? You’re wrong. Or maybe you’re right once, but then you’re going to be wrong later. See my Visa example. And that, to me, was sort of shocking. There’s a massive, massive, massive amount of infrastructure—multibillion-dollar businesses—built around telling people what to do with their money. And yet: Nobody knows. And everybody knows that nobody knows, but still people look for people to give them advice.

Wealthsimple is investing on autopilot

We know that the future is inherently unknowable, and that tells us that the more we try to predict it, the more we will fail. And it’s so scary. You’re always looking for help dealing with that anxiety. If you are, say, Warren Buffett and you can move markets on your own and you can get access to information earlier than other people, then you can probably put your finger on the scale a little bit. But most of us aren’t Warren Buffett. For the vast, vast majority of people probably the best thing to do with your money is stick it in an index fund, check the balance once a year, and never think about it otherwise. And since it’s almost impossible for most of us to know anything, my advice is pay as little as you can to people to manage your money!

But that’s the biggest thing: People know lots and lots and lots of stuff, but nobody knows the key thing, which is what’s going to happen in the future.

Sometimes I worry that being a business owner has affected my ability to see money stuff clearly. I think it’s common. When I was a journalist, there was always some part of me that was a little dismissive of people who seemed to refuse to see the truth. Like, How can you have been so blind? I remember thinking that during the last stock market crash. I thought, How does everyone not see this coming?!

And now that I’m running Gimlet Media, it’s different. If there’s a financial crisis, for a journalist that’s a great story—not that I wanted it to happen, but I saw it as a journalistic opportunity. But as a business owner, if the economy is tanking, that’s really bad news for me. I need the economy to not tank. I need advertisers to not pull back on their budgets dramatically. I need people to be willing to pay for premium content on a podcast network. So when the stock market crashed last summer, my attitude—unlike in 2008—was: Oh yeah, the Dow’s down. Yeah, it’s a correction. Whatever. And it made me wonder whether that was just wishful thinking.

I remember when my concept of money changed. I was raising funds for Gimlet, and I can’t remember whom it was, but I was talking to somebody who was associated with some big-time billionaire investor. And he said, “How much are you looking to raise?” And I said, “I don’t know, a million, million and a half.” And he was like, “Oh, so a small amount. Yeah, that shouldn’t be a problem.” That was the first time someone referred to a million and a half dollars as a “small amount,” and “no problem.” I was shocked. Because obviously that would be shocking to just about everybody, unless you yourself were a billionaire. I’m continually amazed at the craziness of the world of investing.

Investing is complicated. We made it simple.

Learn more

But I also began to understand what’s good about billionaires thinking a million dollars is no problem. The fact that there are people not only willing to give you that money, but who, given a certain set of dynamics, would line up begging to invest that money in your idea that at this point is purely an idea…that is insane and wonderful. Now, they’re not doing it for charity. They need you. But this is what’s sort of exciting about it: You can look at a guy who has a billion dollars and think the way most of us think: Warren Buffett has the billion, and nobody else has the billion. But of course that’s not the way it works. Warren Buffett puts it somewhere—you know, he puts it in a bank, and then the bank has a billion, but they don’t just sit on it; they lend it out to somebody so they can get a mortgage or something like that. Or Warren Buffett doesn’t want it to sit in a bank because he has a family trust and needs to earn a bigger return, so he puts it into something riskier. Maybe he puts it into a hedge fund. But there is a system in place so that billionaire money can be funneled to me when I have an idea for a company.

And in a weird, weird way, the more billionaires there are with billions of dollars that they don’t know what to do with, the better it is for people like me with business ideas. We need each other. They need to do something with their money, and they want the possibility of hitting a couple of home runs with businesses because there are so many failures. And I get to be the bet that they take.

As told to Sarah Goldstein exclusively for Wealthsimple. Illustration by Jenny Mörtsell. We make smart investing simple and affordable.

Share this article