A career in food seemed to be predestined for Singh. Her parents emigrated from the Fiji Islands in the 1970s and landed in Monterey, California, where Singh was born and raised. They opened an ethnic food store, after having both worked in the hospitality industry. Singh developed an affinity for restaurants at an early age.
“I really just love restaurants. Even as a kid, the most exciting thing you could do for me was take me to a restaurant. That was how you could bribe me. I love that you could just go in and order whatever you wanted, and it was different from what we always ate at home.”
After working at a Baker’s Square in high school, Singh ended up at a fine dining restaurant and started studying for the Master Sommelier exam as a way to remain in the business. At the age of 23, Singh moved to Chicago to run the wine program at Everest. She passed the final level of the Master Sommelier exam at 26, becoming the youngest woman to ever achieve the rank. It was also at this time that Singh took over the hosting duties of the WTTW show Check, Please!, where viewers were able to catch a glimpse of Singh’s vast knowledge of wine and the city’s culinary landscape. While working a “9 to 5 job in an office” as Lettuce Entertain You’s director of wine and spirits, Singh says she began to hear the siren song of entrepreneurship calling her name. “It kept haunting me, and I didn’t want to listen at first, because it is very comfortable to stay where you are. Answering that calling can be hugely terrifying, and you don’t want to rock the boat. But I knew there had to be something more than what I was doing.”
The opportunity to open her first venture, The Boarding House, with her business partner Matt presented itself, and the restaurant opened in December 2012. “I just decided to take a leap of faith and do it,” she recalls. Seven Lions followed in 2015, with Terra & Vine opening its doors in 2016 in Evanston.
So what has entrepreneurship been like for her over the past four years? “I once read an entrepreneur describe it as messy. It’s messy. It is filled with self-doubt and self-criticism, but it really forces you to hone your sense of instinct and intuition. It forces you to get in tune with yourself,” she explains. Singh echoes the inner voice of many who dive headfirst into starting their own businesses in realizing that you have responsibilities to more than just yourself.
“I don’t work for myself. I work for 230 employees. I have to make split-second decisions. You just saw one in action: regarding whether to 86 (cut from the menu) the steak for tonight.” (Prior to the start of this interview, Singh had been informed that her meat supplier had just been held up at gunpoint for the steaks that were en route to Terra & Vine. Fortunately, he was okay. The steaks were not, however, and never made it to the restaurant for that night’s service.) “Every day I am faced with 100 decisions like that. Sometimes, it is as simple as the steak, other times it’s deciding which health insurance plan to go with.”
Changing the Conversation
Hijacked meat aside, Singh also makes time to empower women and be honest about what life is like as a successful woman, messiness and all. In a recent speech to the Professional Women’s Club of Chicago, she vowed to tell the truth to the 300 women in attendance.
“I had a year to prepare for this speech. I decided that I just wanted to tell the truth about how emotionally turbulent it can be to follow your calling. Especially for a woman. We should share our stories of imperfection, embrace them, and realize that we don’t have everything and that we shouldn’t have to have it all.”
Singh, like many professional women, bristles at the double standard when it comes to how women are expected to fire on all cylinders—career, family, friends, and maintaining their looks, while the metrics for men have been slow to catch up to those demands.
Paying It Forward
Singh’s work for and with women recently extended beyond the professional sphere when she became involved with Deborah’s Place, an organization that offers housing and services for homeless women. In 2016, The Boarding House hosted a benefit, Women in Whites, featuring an all-women, chef-led collaborative dinner, with proceeds benefiting the organization. Talking about the first time she toured Deborah’s Place space, Singh says, “It was overwhelming and humbling. I met a woman who was living there, and she showed me her apartment. I will never forget the look of pride on her face. I just felt so humbled in that moment to be in her home.” After the tour, she asked what she could do directly to help and was told of their “wish list.” Thinking that they would need things such as clothes and more volunteers, she looked at the list and was immediately heartbroken over the everyday items that were on the list. “It was things like laundry detergent, sheets, socks, deodorant, body wash. Things that I go to CVS to buy and don’t think twice about it,” she explains. “It gives you a moment to be grateful for everything that you have.” Another event, a wine-tasting event at Seven Lions, asked guests to donate items from the wish list. Singh will serve as the Honorary Chair for their annual fundraiser this spring.
The Future Is Female
The women leaders of the future, the way they view feminism and the world at large is also intriguing to Singh, especially her teen niece and business partner’s daughters. “The greatest gift that has been given to me are the young women in my life. I know what values I hold and what is important to me based on what I say to these young girls. I hear myself say things to them, and I think, ‘Wow, I should take my own advice! That was pretty good!’ But these girls are empowered. They know what’s right and they hold people accountable.” cw