Sartorial frustration--and some encouragement from her wife, Naomi Gonzalez--drove Fran Dunaway to launch a clothing line for women with a masculine streak. But when the couple noticed that it was boxer briefs--not button-up shirts--that were flying off the shelves, they realized they had found their hero. --As told to Kate Rockwood

Fran: I wanted a cool button-up shirt, like a Ben Sherman or Robert Graham, and I couldn't find it.

Naomi: I encouraged her to start the business because, well, she was complaining so much.

Fran: Neither of us was looking for a new job--I was an executive producer for a political media strategy firm, and Naomi was a massage therapist. We picked the name TomboyX because Naomi and I both identified as tomboys as kids, and we launched a Kickstarter to raise $75,000 in 30 days.

In that first month, we almost quit. We started with this bang, and then the response energy dipped. By week four, we had basically decided to walk away, when our friend said: "You're not quitting." So we threw ourselves into that week--being funny, trying to get people's attention--and we pushed it over the line.

Honestly, that was a terrifying moment. I was 53, and suddenly I had to not run out of money and to not screw it up. You're looking at a bank account that's dwindling, and it's so easy to doubt yourself. My parents are from Mississippi and I have a small rental home there, and we'd joke about that being our backup retirement plan.

Naomi: We had some friends early on who thought TomboyX wasn't a great name. They worried we'd turn people off.

Fran: But we noticed almost immediately that the name was attracting a lot of attention. So we tried putting it on different things: shoes, belts, hats. Naomi handled customer service calls, and she said someone had called asking us to make boxer briefs for women. I typed "boxer briefs for women" into a department-store site, and the only thing that came up was Spanx. I'm pretty sure that's not what most tomboys want. So we decided to order 600 pairs of underwear, adapted specifically for women, and we had 450 pairs sell before the inventory even arrived at our office. The shirts were selling fine, but when we started selling underwear, our revenue tripled in six months.

Naomi: We met with the founder of Tommy Bahama, who told us: "Find your hero product and go deep with it. Build a strong following." With underwear, we thought we'd hit a vein, but we'd hit an artery. It just took off.

Fran: In 2015, we joined MergeLane, an accelerator in Boulder, Colorado, and, through a cash-equity split, got branding help from ad agency Crispin Porter + Bogusky. That was our rainbow-unicorn opportunity. Naomi and I really wrapped our minds around the idea that this was a true business, and we recentered the entire brand on underwear. We're not telling anyone--tomboys or women or men or gender-neutral people--how to be cool. We think you're cool the way you are, and underwear is this perfect "next to your skin" layer to affirm that. That extends beyond gender, to size and complexion. We're not for everybody--but we are for anybody.

Because our hero product started with a customer suggestion, we're a bit obsessed with customer input. To have people tell you this is the first time they've felt comfortable in their own skin? That stirs this deep sense of responsibility. Our latest category, swimwear, came from customers saying they were hungry for something they could wear to the beach. You don't know what you're going to hear until you listen.

We were in our office one day when this 11-year-old, Zoey, came in with her parents. She was from Cheyenne, Wyoming, and taking an RV trip with her family, and she begged them to stop in Seattle so she could visit our headquarters. She had us all in tears, the brand meant so much to this young tomboy in Wyoming. Zoey was the first girl to make the local football team. She was wearing TomboyX temporary tattoos under her football helmet when she hit the field.

Finding Comfort In Their Own Skin

Before starting our company we were: An executive producer for a political media strategy firm (Fran) and a massage therapist (Naomi).

How to cope with stress: Laughter.

The most important social media platform for our business: Facebook.

Biggest challenge facing your business today? Attracting and retaining employees.