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.

I realized that we weren’t rich when I was 10 or 11, and I was a little miffed. I come from a family with three kids. My mom was a registered nurse, and my dad worked with Boeing. We didn’t worry about money — we were comfortable, went on family vacations — but my parents were frugal and clearly aware of the value of money. We didn’t get Levi’s jeans; we got Big Yank jeans, to no end of shame — we were those guys. We didn’t really go out to dinner. You had to get 30 gold stars in a row for perfect table behavior, and even then, we might go to a fast-food restaurant. Our allowance was tied to our chores, and we had to have a job if we wanted spending money. I picked strawberries one summer, then got a paper route.

My siblings and I always knew we would go to college. Our parents saved for it. They paid for me to go to Rutgers, which at that point, in the late 1970s, was $900 a semester for tuition, room, and board. Before I left for college, my dad took me to get a checking account and told me that I’d get $25 a week for spending money. It would be released on the Monday of each week, so I’d learn what $25 a week is worth instead of what it was worth over the course of a weekend. This was 1978. I was happy — it was free money!

It wasn’t cool to be a cook. It was the last thing people did after the Army and before jail.

I also got a job in the dining hall, making about $6 an hour; the minimum wage was $2.20. When I began working at Stuff Yer Face, a pizza and stromboli place, in my second year, I started at $7.50, but pretty quickly I was up to $10, $11, $12 an hour because I was fast, a good motivator, and a team player, and the business was successful. I was paying my own rent by junior year. I’d get paid, go to a fancy beer bar, and order a $7 beer. Every now and then I’d take a girl out on a date. One time I brought $250 cash into New York City —
dinner, taxis, a concert — and we ran out of money in the middle of the night. I didn’t have a credit card: Regular college kids didn’t qualify for them. They were an adult luxury, and my parents weren’t about to pay the bill.

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I got degrees in Spanish theater and economic portfolio theory, but I never wanted to cut my hair, wear a suit, and work on Wall Street like a lot of my friends did. Some of them were partners at Goldman before it went public and they retired early. Now they live in Marin County, California, and cultivate bonsai trees. My brother retired last year from Pixar; he builds experimental musical instruments. They all had stock options, worked hard, and enjoyed their work. But their goals were to not work. My goal is working as long as I feel like it. I love what I do.

After college I attended cooking school in London, where my parents were living. We split the tuition. It wasn’t cool to be a cook then. It was the last thing you’d do after the Army and before jail. I was a bartender, then basically an indentured servant to chef Marco Pierre White, who has been called the first celebrity chef. I made a couple hundred pounds a week — shift pay, six nights a week — but I would’ve done that job for free. After that I had a few jobs. I did catering in San Francisco for $70 a shift, five or six shifts a week. I worked at a Four Seasons hotel as a sous chef, and I made $50,000 annually, which was big time. When I went to the Four Seasons in Santa Barbara, California, I had a $70,000 salary, making me the company’s highest-paid sous chef. And I was probably the only person in Santa Barbara earning $70,000 a year who didn’t have 10 cents to his name. My rent was $185 a month, with a couple of roommates, and we lived really large. I lived my paycheck, every week.

Then the Four Seasons asked me to help open a property in Hawaii. For me, it would have been a death sentence, plus I was prone to island fever. So I started saving a little bit and asked around to anyone who could help me get a job in Italy, working for free in exchange for room and board. One person responded, and I took a job at Trattoria la Volta in Poretta Terme. I had about $3,000 to my name. I thought I’d stay for three months, and it turned into two and a half years. After my money ran out, the two brothers who owned the place would slip me 100,000 lire here or there, which was about $80, to help me get by. It was a good experience, a formative experience for me.

When I got back to the States, I worked for awhile at the Café Tabac in New York for $1,200 a week. This was in the East Village in the '90s, when Café Tabac was legendary. It was not the most important money I ever made, but I loved that place. Crazy supermodels would come into the kitchen and spray each other down with the dishwasher hose. I hung out with Ray Charles one night. But that’s when I met my wife, Susi, and I started the transition from employee to owner.

Susi heard about an available restaurant lease and asked to see the space. I loved it, and it was inexpensive. I borrowed money from three people, my business partner got some money together, and for $32,000, we opened Pò, our first restaurant, in 1993. Three months in, The New York Times gave us a glowing review. It was kind of a dream. Our prices were $8 to $10 for appetizers, $10 for pastas, and $15 or less for entrées. We did a six-course tasting menu for $29. Our monthly rent was $3,200. We paid our investors back in eight months and owned a really good restaurant that, in its day, was doing about $2.5 million a year, which was — and is — a lot of fucking money.

A year later I got on the Food Network, doing Molto Mario. I was paid $400 per episode, 75 shows per cycle, so in the space of a few weeks I’d make $30,000, which felt like a lot. Then, right after I sold my first book, I met Joe Bastianich. Between my advance and Joe’s money from his first restaurant, Becco, we opened Babbo for about $200,000 and started turning a profit pretty early. Within the first year, I was making a couple hundred grand.

Just like when you buy that first ounce of weed and sell three-quarters of it (or so I’m told), we started to reinvest our capital in new ventures. We now have 28 restaurants and a $200 million a year business, so we’re doing alright. Of everything I do—TV, books, product lines — restaurants are by far the most lucrative. Almost all of our restaurants are partnered, meaning that the chef and general manager have a small piece of equity, even if they didn’t chip in. When you give someone equity, they operate like owners — no one steals chickens, no one walks out with a case of wine because they feel like they’re being screwed by the man.

If you don’t owe anybody money, you don’t have to take any shit from anybody, ever.

To anyone trying to get ahead, in the restaurant business or really any industry, I’d say, set goals — short, mid, and long term. You don’t have to be a slave to them, but you need to get on a path to what you think is a better place, whether that’s owning a restaurant, working in Aspen in the summer and the Caribbean in the winter, or whatever. Find the lifestyle that is conducive to making you extremely happy. Happiness is so much more important than money. I know a bunch of stoned-out bus drivers in San Francisco who are happier than many of my friends in New York who make more than $1 million a year.

Also: Live within your means and don’t accumulate debt. Debt limits your freedom to make decisions. Debt’s good for buying real estate; it’s not good for paying for vacations. If you don’t owe anybody money, you don’t have to take any shit from anybody, ever. Only take on debt for a good investment that will eventually buy you freedom, and evaluate your ability to repay that debt load.

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I don’t spend a lot of money on myself. Clearly my wardrobe costs pennies compared with most other people. I have one watch. My car is a Ford Flex. I ride a Vespa. But we have really good vacations, and I’ll upgrade to first class when I fly. I don’t care about anything else. We’ve lived in the same apartment since we bought it in 2000; we have plenty of space. I’m not buying a house in the Hamptons. About 10 years ago I bought a vacation house in Michigan for $400,000, which at the time was the price of a cheap studio apartment in Manhattan. We’re definitely not on the same treadmill as some very successful people in New York.

My kids are in college now. They know the value of money and appreciate what it can buy. But I worry that they’ll become obsessed with making money. The last thing I want is for them to pursue a job solely because it will make them rich. Several of their friends’ dads are hedge fund guys or Wall Street guys. It’s huge money, but I tell my kids, “If you love that, then do that. But if you’re doing it just for cash, you’re going to be real bitter at 40.” It’s hard to tell them how to get that job. Lots of those guys are hired by an old-school, take-care-of-my-buddies system.

I like to ask my kids, “Who’s the happiest dad you know? Me! Because I love what I do.” I don't want them to treat college education like it's a trade. You should go to college to learn to be fascinating — and fascinated — which makes you invaluable for every single company. If you’re solution-oriented, with a vocabulary, and can speak and behave in a way that makes people feel good, you can work at any multinational, doing something, for a lot of money. My wife has said all along that if our kids become circus performers, she’ll support them until the day they die. No one has yet gone for the circus performer option.

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

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