8 min 11 sec

Underwear Side Hustle Turns Into $500,000/Month Business

Two women launch an underwear brand in their spare time. It grows from an early Kickstarter campaign to a multi-million dollar company with more than a dozen employees.
High Profit Niche Ideas Partnership Retail

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What It's About

An inclusive underwear company for every body.

Business Model
Skills Required
Design & Experimentation
Profit Potential

Words of Wisdom

Fran and Naomi did a lot of research prior to launching and while they were building TomboyX, and one of the most important things they learned along the way was that lifestyle brands with real staying power started by focusing on one "hero" product and building from there. Their customers had been asking them to make boxer briefs for women, so they listened. And that's how they found their hero product that paved the path for new products!

Fun Fact

Fran and Naomi have quite a knack for spontaneity—in 2014, they surprised friends by staging a surprise wedding during a flag football game. "At halftime, the ref, who was an ordained clergy, blew a whistle and married us right there,” Fran remembers with a laugh.

Notes from Chris

Episode 556

Fran Dunaway is the CEO and Co-Founder of TomboyX. The company makes underwear, swimwear, and loungewear that isn’t for everybody but is for anybody. They’re focused on fit and quality, offering every style in sizes XS to 4X. They’ve gone from zero employees 2 years ago to 15 today.

Before they started what was supposed to be a side project, Fran and her co-founder Naomi (who is also her wife) weren’t experts in fashion. Both of them had careers they enjoyed. But they also had a burning desire to make beautiful button-up shirts for women. They wanted to create a shirt with fine quality fabric, fun details and fit for a woman’s body. They chose the name TomboyX because they thought it was cute.

To compensate for their lack of background in the fashion industry, Fran and Naomi did a lot of research. They wanted to see what made a lifestyle brand truly “stick” with a dedicated fan base, as opposed to all the ones that came and went. They discovered something important: the lifestyle brands with staying power started by focusing on one ‘hero’ product and building from there. This doesn’t mean that they don’t expand and add products, but it does mean that they build the core business around that one hero product.

A Kickstarter project for TomboyX shirts out-raised its $75,000 goal, but they also learned something important through the process. The hero product for TomboyX was boxer briefs for women. They got more requests for that than anything else.

With this brief front in mind, they set out to make the softest, longest lasting waistband out there. They were determined to create one that you don’t even notice because it’s so comfortable, doesn’t leave a mark, and doesn’t cut off your circulation.

Since then they’ve perfected the formula for spending on ads and bringing in new customers, especially through Facebook ads, but also through podcast ad buys and other mediums. They have a team that does nothing but work on this. Instagram has been especially important for engagement, and they communicate daily with more than 75,000 followers.

If that sounds intimidating, remember, this is now a company. It wasn’t their goal to turn their side project into a multi-million dollar operation.

They found their hero product, but they also made their customers their heroes. Images on that Instagram profile and their website tell the stories of the target market they started with: not everybody, but anybody. They’ve clearly struck the right tone with the right products and the right audience.


  • TomboyX: Life is too short to wear underwear you're not comfortable in. There's something for everybody over on Fran and Naomi's website!
  • Kickstarter | TomboyX: The Kickstarter campaign that started it all!
  • Shopify & Amazon: The two platforms that Fran and Naomi used to sell their products
  • ShipStation & Stamps.com: The two platforms that they used to ship out all of their products
  • MailChimp: The email marketing platform that the duo used to help manage their subscribers
  • Google Suite, Dropbox, Slack & Asana: The multiple platforms and programs that Fran and Naomi used for productivity


Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"Our research taught us that the lifestyle brands with legitimate staying power started by focusing on one ‘hero’ product and building from there."
—Fran Dunaway #SideHustleSchool

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Chris Guillebeau