The path from chef to entrepreneur was not an easy one for Dennis Leary, who now owns six restaurant and drink establishments in San Francisco and has won numerous awards for his culinary skills.
“I was a pretty good cook, but I was an atrocious manager because I had no real management experience,” says Leary. “I had no idea what I was doing. I didn’t know what contractors to call. I didn’t know how to deal with the city. I didn’t know what permits to get. I didn’t know anything.”
What Leary did have, however, was the drive and determination to learn the skills he would need to become a successful restaurateur.
“When I was younger and I worked for a few entrepreneurs, I saw how much they loved the hustle of doing deals and setting things up,” Leary says. “I could tell it was an exciting thing. If you’re going to be good at any one thing, you have to dedicate your life to it.”
A blue-collar chef
Leary got his start in the kitchen as a young boy cooking with his mom in his hometown of Cohasset, Massachusetts.
“I always loved cooking and I always loved to eat,” Leary says. “So the kitchen environment was really fun. I never went to culinary school. I went through the old guild system of cooking. I was an apprentice and then I was a journeyman baker for a while. I moved to San Francisco in the late 1990s and worked with a pretty fancy pastry chef.”
Leary took a job at a restaurant called Rubicon in 1999 and soon became executive chef. After a few years, he left to start his own restaurant using money he had saved along with contributions from his mother and brother.
“I built the place myself and I did breakfast, lunch and dinner,” Leary says. “I killed myself for a couple of years, but that led to where I started my entrepreneurial arc.”
Leary got some attention from the press for his efforts and was encouraged by some to take the next step to a bigger restaurant. But a friend of his had a different idea.
“He’s a comedian and he said, ‘You should do something smaller,” Leary says. “You should tell people that this restaurant called The Canteen has gotten too big for you and you need to go in a different direction. So I opened a 236-square-foot sandwich shop in 2008 right as the recession was taking hold in San Francisco.”
The new eatery struck a chord with customers looking for a low-cost, no-frills option, and Leary was on his way.
Today, Leary owns Café Terminus, Golden West, House of Shields, Natoma Cabana, RX and The Sentinel. He grows vegetables and roasts coffee for his restaurants at his 40-acre Andromeda Farm in Capay Valley near Sacramento.
“I now know a little bit,” Leary says. “But I still feel it’s about staying humble, having a sense of humor and having a very strong sense of irony as an entrepreneur. As a chef, you just need a lot of drive and it doesn’t hurt if you’re articulate.
“If you can present yourself to the public pretty well, that helps too. But I feel that aspect of being a chef is very new. That’s the post-Food Network, post-celebrity chef era. When I was growing up, even in to the early part of my career, cooking was still a pretty blue-collar thing. I’ve always had a blue-collar mentality.”
A simple mission
Leary says his approach to being a chef has changed quite a bit since becoming a restaurateur. He’s not in the kitchen every night getting his team pumped to take on that night’s service.
“My mantra now is I don’t care what it is that they’re cooking as long as it tastes good and you can sell it,” he says.
“You have to offer the client a value proposition. Not as much passion needs to go into it. It’s more about being consistent and keeping everything fresh. Good value for the dollar. I don’t think that’s as difficult to instill. It’s not like I’m trying to get people to be artists. Now I try to make things fun, but professional.”
In terms of managing the menu to keep customers coming through the door, Leary says that tends to be a moving target.
“I have one place where the ladies come in and they want the same salad every day,” he says. “They want a kale salad with chicken every day. We like a certain amount of uniformity and consistency and then what’s affordable and available throughout the year. If you have people who are excited about making something and it’s delicious, they can get pretty excited about it. In a weird way, that enthusiasm can translate to the diner’s enthusiasm.”
As for the future, Leary says he’s in a holding pattern.
“I’m waiting for the economy to give me a signal that it’s going to move in one direction or another,” he says. “Right now there is this crazy hysterical boon fueled by tech money in San Francisco. There’s more traffic, more people and it’s great for business, but I also feel the other shoe could drop. There are things I want to do, but I’m just waiting.” ●
