The road from analyst to lingerie company founder — and the mentor who …

When Heidi Zak was a young investment-banking analyst, stuck at the office until 3 a.m. with her supervisor Lisa Kaplowitz, she couldn’t imagine that one day she would start an online lingerie company.

Or that her supervisor-turned-mentor would encourage her to do it.

But now, 15 years later, Zak, 36, and her husband, Dave Spector, are running San Francisco-based ThirdLove, a startup that designs and sells lingerie at a mid-range price point. The company offers half-sizes and has a patented bra-sizing app that’s designed to make shopping for lingerie an easier, less invasive proposition.

The couple launched the concept in 2014 to much fanfare: ThirdLove’s app has been featured by Apple as “best new app” or “best lifestyle app” more than 20 times.

And Zak points to several key advice sessions with Kaplowitz — now the CFO of Hello, an oral care products startup — that helped her transition from finance to retail and, ultimately, to the world of startups.

“Those moments when I’ve been thinking about making a large decision … she’s been there to push me to make those big decisions,” Zak told Bizwomen.

Here are three of those moments:

1. Debating a career change: When Zak and Kaplowitz first met, the elder was fresh out of Northwestern’s Kellogg Graduate School of Management and an associate investment banker at Bank of America. Zak, an analyst, was straight out of undergrad at Duke University.

There weren’t many women in either of their programs, and they connected. Both had been competitive gymnasts. Both had a lot of energy. And both had similar aspirations.

Zak wanted to move into retail operations. But she was struggling to get interviews. Kaplowitz — who left Bank of America to become the treasurer of Bed Bath Beyond — suggested business school. It gives you options, she advised.

“She’s probably the biggest reason I took my GMATs and why I applied,” Zak said. “It was instrumental in changing my career path.”

Kaplowitz also was a reference. And Zak got accepted to one of the nation’s top MBA programs, at Massachusetts Institute of Technology’s Sloan School of Management.

2. ‘Company or baby?’: After business school, Zak spent four years on Aeropostale’s corporate team, getting the retail experience she’d desired. Then she took a job on the marketing team at Google — a position with the kind of perks most wouldn’t abandon, particularly when you’re considering starting a family, as she and her husband were. Google offers six months of paid maternity leave.

But Zak had a business idea that would make shopping for bras simple and convenient. So she called Kaplowitz, a mother of two. Zak shared her idea for ThirdLove, as well as her desire to have a baby. Could she reconcile the two? she asked.

Kaplowitz offered some unexpected advice: It may be the ideal time — to do both.

“I said…’The reality is, if you’re not going to do it now, you’re not going to do it,’” Kaplowitz recalled. “‘You’re financially secure enough to take this risk. …You could work from home with the baby.’”

Zak admits that the advice wasn’t conventional: “People were like, ‘Why are you leaving a well-paying job to not take a salary, to bootstrap a company, to work way more, potentially while getting pregnant at the same time?’” Zak recalled. “And I thought, ‘I have to be a little crazy to be doing this.’”

But Zak did it — and then followed another key piece of Kaplowitz’s advice: Hire a top-notch and flexible nanny.

3. The investor game: More than a decade after Kaplowitz began advising Zak, their roles reversed: Kaplowitz, 41, needed Zak’s wisdom.

As CFO at Hello, New York City-based Kaplowitz was in charge of raising venture funding. Many of the firms were based in San Francisco — Zak’s territory — and Zak knew the fundraising process well, having brought in $5.6 million for ThirdLove.

She advised Kaplowitz on the kinds of investors to approach, the challenging questions to prepare for, the type of growth investors would get excited about.

“The best kind of mentor,” Zak said, “is somebody who’s made similar types of decisions in her life.”

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