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

When Katrina hit, we were building our new restaurant, Cochon, in New Orleans. We had already started construction, but it was only a concrete floor and beams. My father-in-law — he's my business partner — and I had a meeting: How much were we in for? If we bailed out then, what was the damage? We’d have lost about $100,000. But it was another $350,000 to go forward. I said, “Give me a day. My head is so messed up right now. My house is underwater. My staff is scattered around the country. Just give me a day.”

It was a far cry from how I started in this business, which I guess all began with a car.

The car was an old MG, and my father said I could have it if I paid to fix it up, for gas, and for everything else. So I got a job washing dishes for something like $3 an hour. Eventually, I moved up to line cook. The one time I’ve worked outside of a kitchen since that first job was two years unloading trucks when I was in college. But at first it was fry cook, hamburger cook, those kinds of jobs. I didn’t know anything about fine dining; there was no aspiring to be a sous chef or anything like that. All I knew was that I liked cooking a lot and that I was really good at it.

In college, while I was working 40 hours plus and still trying to get to class, I started to think, This sucks. Why does everybody else get to just go to school while I have to work?

I grew up in Sulphur, Louisiana, in Calcacieu Parish. My dad worked a union job at an oil refinery. My mom stocked groceries. We were pretty basic working class, I guess. We didn’t travel. Eating out was for special occasions—we’d go to Great Wall of China or whatever the local Chinese place was called. In a way, I didn’t have a concept that there were people who lived differently from us.

There were big houses in Lake Charles, near where I grew up, and now I look at them and think, “That guy’s a millionaire.” Back then I didn’t register things like that. It wasn’t until my family joined the local tennis club that I noticed we didn’t have the money some of the other members had. In college, while I was working 40 hours plus and still trying to get to class, I started to think, This sucks. Why does everybody else get to just go to school while I have to work?

After college, I became the chef at a restaurant in San Francisco called Cha Cha Cha. I made $10 an hour, plus overtime and tips. That was the most money I’d ever made! I remember thinking, I finally have money. But I couldn’t do anything with it because I was so beat. I’d work six days a week, and when Sunday came around, I was asleep on the couch with all of my cash in my pocket. I was in my 20s, I had no savings, no insurance, but I felt like I had so much money. So I bought a $400 telescope.

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It never crossed my mind that it would even be possible to have my own restaurant. I was happy simply being a chef. Then the owners of this place I was working offered to open a new restaurant with me as the chef and as a partner. That’s when I learned some hard truths about contracts and partners. The deal was that I’d be a one-third partner, and I didn’t have to put up any money: My work would be my share. But they dragged their feet getting me a contract. Meanwhile, we opened, and we were a hit. There were lines down the block. I finally got the contract, and it said that I needed to pay them $800,000 for my share. The lesson: Be careful who you’re doing business with. Make sure you understand the deal you’re making. And never do it because someone says, “Don’t worry—the contract is coming.”

In 2000, I borrowed $50,000 at 10% interest to open my first restaurant in New Orleans, Herbsaint, with New Orleans chef Susan Spicer and my father-in-law. It was terrifying. Summer came — when everybody leaves because of the heat — and business slowed to a trickle. It was like, Holy shit. I don’t know if we’re going to make it. I loved it though. I started to see how the business could be a part of the art. You’re in the kitchen less, but you feel like you’re always working—at home, on the phone, checking email. It’s not just a job; it’s all of it. After years of being in the kitchen, it was natural. It all made sense. A whole fish costs this much, you divide it by this many portions, and you get your plate cost. I knew how to do all of that.

Things changed, financially. You know how it works, you make some money, then you buy a house, and things start to get tight. So you work more, feel like you have some money, and kids come along, so it gets tight again. It’s a cycle that gets ratcheted up.

The truth is, I’ve always felt in over my head in a way.

By the time Katrina hit, we’d started to build our Cajun restaurant, Cochon, I was counting on it getting me out of the financial hole, so that added to the math. But I had that meeting with my father-in-law when we had to decide whether to eat the $100,000 we’d already spent or go all in. I took the night to decide if we were going to go ahead. When we talked again, I told him, “Look, man, New Orleans isn’t going to go away. If it was a good idea then, it’s a good idea now. Let’s push on.”

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Herbsaint has now been open for 17 years, and I’ve got two more restaurants in New Orleans, Cochon Butcher and Peche, plus a version of Butcher in Nashville. And the truth is, I’ve always felt in over my head in a way. I remember how much sleep I used to lose: Oh, my God, we have to pay all that money back! What if it doesn’t work? But we said, “It’s going to work. Because it has to.” Even if we had to do everything ourselves.

If you do things with just money in mind, it’s probably not going to work.

After a while, you get to the point where you can make decisions without spending more than you can afford to lose. That feels good. It’s the same as gambling. If I’m going to play blackjack, I’m only bringing a certain amount of money. Win or lose, I’m not going to spend any more than that. I know some people can’t do that, but I can. That’s how I survived opening an outpost of Cochon in Lafayette, which closed after 14 months. I had doubts about it even before we opened, and I could tell from the beginning that people didn’t like it. They thought the menu was weird; they thought the prices were high; they complained about everything. We thought Lafayette was going to be a big moneymaker, and that wasn’t the right way to go about it. If you do things with just money in mind, it’s probably not going to work.

My daughter is 17, and she’s starting to figure out that we have a little bit of money. I don’t make her work because she’s captain of the tennis team and makes great grades. But she’s going to have to start pulling her weight now because she wrecked her car. I’m going to make her take a few shifts.

I want her to feel it.

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

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