Total bosses

Leanne Mai-ly Hilgart, CEO & Creative Director, Vaute

Why she’s a total boss: She founded a completely vegan fashion brand before it was a thing … during that recession.

Words of wisdom: “You do your best and prepare, but it’s in your interactions with the world that you find out what actually works.”

Chicago native Leanne Mai-ly Hilgart has been passionately protective of animals since she became an activist at age 8 and vegetarian at age 10 (she grew up near McDonald’s headquarters). It makes sense that she founded the world’s first vegan fashion brand in 2008—with a focus on keeping people warm.

“I realized business was an amazing vehicle for making exponentially more impact than as an individual,” says the former model. She decided to do what no one else had: create a chic winter dress coat free of wool, silk and other animal-derived materials that also was warmer than everything else on the market—vegan or not.

Especially at the beginning, the challenges seemed endless. The fact she wasn’t driven by money or trends but by passion and her moral compass got her through. So did staying flexible.

“I never would have made it through the trials and tribulations of starting and bootstrapping a business in the bottom of a recession,” she says. “I wouldn’t have made it a month—it’s very painful.”

The biggest moment for Vaute—which combines “haute,” part of the French expression meaning “high fashion,” with a “V” for vegan and “sounds like vote, since we’re voting every time we buy something”—proved pleasure and pain often commingle. Hilgart had strep throat, a dislocated collarbone and a recent breakup to contend with during her trailblazing first solo show at New York Fashion Week in 2013. A glowing CNN story about the show led to congratulations and requests from around the world, but she couldn’t move.

“I was crying my eyes out because I was in so much pain, but I also knew we had started to really make an impact,” she says.

Hilgart keeps herself going with support and inspiration from her heroes, like author Seth Godin, her parents and a circle of “brave” women who are equally honest about “how many failures go into a success. We can all see that instead of assuming it’s luck or [that] someone else has it better than we do.”

When it’s time to make decisions, she checks her gut instinct with tree-like diagrams showing feasibility and result. “Being an enthusiastic, optimistic person, you like to say yes, but time and energy are some of our greatest resources, and they’re limited, which is hard to remember until you’ve depleted them.”

After a particularly difficult 2017, Hilgart went from a “do whatever it takes to get it done” person who rewarded herself with things like exercise to one who schedules those things that “fill her up” first. It has significantly increased her productivity.

“Yoga I do almost every day now, and I plan time for my friends. These are non-negotiable.” (She also swears by plenty of probiotics, green juice and her fave turmeric-spiked elixir.) “These are not rewards,” says Hilgart. “They’re fuel for my work. These are things I get just for being alive, because I’m worthy of taking care of myself.”

The Game Changer

Payal Kadakia, Founder & Executive Chairman, ClassPass

Why she’s a total boss: She revolutionized the concept of “fitness membership” … and when fitness is fun and flexible, people actually get fit.

Words of wisdom: “The hurdles aren’t always fun along the way, but it’s beyond exhilarating when we conquer them.”

Passion for dance directly led to Payal Kadakia’s groundbreaking idea for ClassPass, an app-based fitness membership that gives users instant, seamless access to thousands of fitness studios and classes in 50 cities around the world. ClassPass members can hit up a yoga studio one day and a barre class the next—at times that work best for them.

The MIT grad’s lightbulb moment came just hours after meeting entrepreneurs for the first time. “Entrepreneurship is a perfect vehicle for delivering soul-nourishing experiences at scale,” says Kadakia. “Meeting them, I realized that I, too, could create a business. Thirty-six hours later, I was searching for a ballet class [to] and had the inspiration for ClassPass!”

It took a lot of painstaking iteration to find the right product-market fit with the intended result, says Kadakia, but that process meant constant learning. And something unexpected happened: She realized she could do more than her original idea, like radically change the nature of gym membership. “The more we achieve, the more ambitious our goals become,” says the founder.

Kadakia was fortunate to be raised by forward-thinking parents (“the strong, brilliant woman, and the equally brilliant man who supported her”) who modeled positive behavior. “My mom approaches every challenge as an opportunity to grow, and my dad loves this about her, so I grew up believing that strong women should be encouraged and celebrated,” says Kadakia.

She believes women should comprise 50 percent—or more—of successful entrepreneurs. “It’s of critical importance to encourage more women to dare to dream big,” she says. “They must believe they can be anything they want.”

Kadakia balances her strong creative side as a dancer and choreographer with an analytical and methodical business mind. Unsurprisingly, making time to move and work out daily is a top priority. She and her employees go to work dressed in activewear and take breaks to attend their favorite classes (she personally loves blending traditional Indian dances with contemporary styles, and she’s a fan of cycling, Pilates, barre and strength training).

She also runs The Sa Dance Company, which, along with ClassPass, requires hyper-organization, laser focus and a ruthless approach to prioritizing what’s important. Her secret to success boils down to perseverance, work ethic and focus. “I simply won’t stop until I’ve accomplished what I’m after!”

Case in point: “When I was 25, I wrote a check for $30,000 to the Alvin Ailey [American] Theater guaranteeing we’d find a way to sell out three dance shows. I figured out how to do it, took the risk and made it happen.”

The best lesson Kadakia has learned so far? “Regardless of our roles in life, we all need to evolve. It’s as true for founders and artists as it is for any human being. We all need to grow and keep growing.”

The Empowerer

Meghan Asha, CEO, FounderMade

Why she’s a total boss: She’s turning other people’s wellness, food and beauty products into success stories … and that’s a win for anyone who’s a healthy lifestyle fanatic.

Words of wisdom: “To own the restaurant, you gotta do the dishes.”

It’s Meghan Asha’s imaginary 90-year-old self, “the hottest, coolest lady,” who’s actually responsible for FounderMade, a company that hosts curated summits to help inspiring lifestyle brands grow. Basically, Asha has made a business of empowering others.

“I was working in venture capital and I was a little depressed,” says Asha. “I asked myself, ‘When you’re 90, what will make you happy?’” She decided to host a dozen monthly dinners in her apartment complex and call the dinner series FounderMade. Entrepreneurs in the consumer sector—think founders of groundbreaking makeup or healthy snack bar companies—would speak about their journeys.

When one speaker’s publicist requested that 300 people attend, FounderMade naturally evolved into something bigger, organically becoming the comprehensive conference series it is today. Now, FounderMade connects entrepreneurs with distributors, influencers and investors. On the flip side, it helps people discover new wellness, beauty and food brands that will actually make their lives more awesome.

At FounderMade’s first official summit in January 2016, “my 90-year-old self was smiling at me like, ‘This is what you’re supposed to be doing. It’s the happiest day of your life,’” says Asha. “You can’t put a price tag on the joy I derived from that day.”

Because she was doing it as a “labor of love,” Asha wasn’t even aware she’d started a business. But the universe kept leaving her breadcrumbs that pointed to this being her purpose. She received cosmic messages like half-price office space in Soho that said, “You’re on the right track.” Old-school thinking requires extensive business plans before launching something, but Asha, who calls these “learning docs,” happily didn’t play by the rules, instead earning her confidence in the business as it grew.

She does, however, advocate being crystal clear on mission and goals—even those that change later—in order to track progress. Her mission, which she wants on her tombstone, is that she loves helping people build businesses and reach their full potential. And on a recent solo truffle-hunting trip to Rome, Asha wrote her goals over and over on her phone. She looks through them daily.

She also regularly schedules time off (to train for the Paris Marathon, for example). Every morning, she does “meditative and super intense” interval training to keep her mind sharp.

Valuing humility and integrity more than her MBA, Asha feels she truly hit her stride as a leader when she was able to admit, and proclaim, that she’s bad at many things. The epiphany allowed her to focus on the areas in which she excels and hire colleagues talented at the other things. Even so, she debunks any fantasies of success without continuous challenges.

“You know what? All businesses are hard,” she says. “Everything in life that is worth anything is hard.”