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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Lingerie Brand Expands Options for Breast Cancer Survivors

AnaOno Intimates offers bras and lingerie for women of all shapes, sizes and surgeries

Having undergone major surgery, the last thing breast cancer survivors need is problems with a simple task like getting dressed. But up until now, they have had limited options in terms of bras that fit, let alone that look and feel good. A new US-based lingerie company, which is exclusively for breast cancer survivors, aims to solve this issue. AnaOno Intimates offers styles for women of all shapes and sizes who have undergone unilateral to FLAP surgery, or enhancement.

Dana Donofree, founder of AnaOno and breast cancer survivor, explains:

I launched AnaOno Intimates after my own struggle with finding beautiful and comfortable lingerie after my double mastectomy at the age of 27. My diagnosis rocked my world, I didn’t expect to change many parts of my lifestyle as well.

Following surgery, Donofree found that she couldn’t find lingerie or bras that fitted.

When going through the surgical process of the reconstruction, you can understand why you don’t fit into your clothes, you feel like you are on a medical journey and the excuses make sense. It wasn’t until after I got my swap out into the implants, that I went back to my underwear drawer that wasn’t touched for a year, to find out that NOTHING fit me. It was really a struggle at that point, in and out of lingerie stores, leaving in tears, and frustrated that I was not prepared for something so simple to now be one of my many challenges presented because of breast cancer.

As a fashion and design graduate from Savannah College of Art and Design, she set up AnaOno Intimates to ensure that women no longer faced these challenges after battling cancer.

As well fitting perfectly, AnoOno Intimates are designed to look stylish and beautiful. Up until now, many breast cancer survivors have resorted to lingerie that is purely functional and not designed for the different needs of women post-surgery.

Donofree tells PSFK:

I think the conversation is changing and women are getting more vocal about their bodies and their treatments. I have women emailing me telling me how exciting it is to see my line because they have been wearing a sports bra for five, 10, 15 or even 20 years.

I’m not sure we were having the conversation that this was not OK, that we deserved to feel beautiful and confident after surgery and if a pretty bra does that, then we should have it!

Underwear for survivors has previously been regarded as an extension of medical needs and it has not adapted to the rise of women with reconstructions, Donofree explains:

We have been viewed in many cases as “medical needs” and devices due to the need of using breast forms and prosthetic, so insurance companies get involved and get coverage for those women, but women with reconstruction do not have those same options, so maybe current companies that supply mastectomy bras did not expand for reconstructed patients.

Donofree designed AnaOno Intimates to be inclusive, offering options for women who have undergone many different types of surgery and for those with or without reconstructions. The line has unparalleled range of sizes and styles, including wire-free bras, bralettes, pullover bras and sports bras.

For Donofree, one of the highlights of launching the brand is receiving feedback from survivors who appreciate the fact that they can now access fashionable and well-fitting underwear.

I am so thankful for the support and generosity of many of the women sending me emails, telling me about how putting on something beautiful changed their day for the better! There is also this reference to finding your “new normal,” and this may be a step in that direction for some.

In the future, Donofree would like to make AnaOno Intimates available internationally.

It breaks my heart to read some of the emails I receive from women in other countries with the same struggles finding a bra and the emotional impact that comes with that, I just want to reach as many of them as possible, to feel beautiful, confident and proud. I want them to know that they are never alone.

Not only is AnaOno Intimates the first lingerie line adapted to the many different needs of breast cancer survivors, it also donates 10 percent of all sales to breast cancer foundations. The line offers survivors comfortable, stylish underwear options as well as the ability to support others with the disease with every purchase.

AnaOno Intimates

Photography by Tracy Birdsell Photography for AnaOno

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