Three Founders on Their Origin Stories, Fundraising, and Their Decision to Sell

Sadly, the odds of launching a successful business venture are slim—about half of small businesses fail within their fifth year. But the female founders featured on Marie Claire’s 2022 Power Trip summit about making a grand exit defied those odds. On November 15, author and CNBC senior media and tech reporter, Julia Boorstin, spoke with panelists Tracy DiNunzio, founder of Tradesy, Michelle Cordeiro Grant, founder of Lively, and Jaclyn Johnson, founder of Create & Cultivate, with each leader detailing their company’s unique origin story and what ultimately led to their decision to sell.

The road to success looked different for each woman. For Johnson, who founded and sold her first company No Subject by age 28 (nbd), becoming a business owner wasn’t something she planned. While running her first business and “making a ton of mistakes,” Johnson took to Google to search for answers. “I realized that there was nothing online that looked, felt, or spoke to me as a young millennial female founder,” she said. “So I decided to [start] Create & Cultivate as a complete side project of the existing business that I had. And it really took on a life of its own.” After going through the process of selling her first company, Johnson thought to replicate that process again. “Going into Create & Cultivate, I knew I was building to sell that company, so there were very specific steps I took along the way to create a company that would be viable for a sale,” she explained. 

Johnson decided to self-fund both of her businesses, which she says came with its own set of problems. But, ultimately, she had a few good reasons for bootstrapping rather than fundraising, she said. Firstly, Johnson explained that Create & Cultivate was already extremely successful and didn’t need the cash. Her second reason was a matter of control; Johnson loved being able to move quickly and make her own decisions. Lastly, she explains, “I think it would've been extremely challenging to fundraise for a women's media and conference business given that, you know, 98 percent of venture capital are people who we are not advertising to or would understand our company.” 

Meanwhile, the founder of lingerie brand Lively, Michelle Cordeiro Grant, was inspired to create her business from window shopping on New York City’s Fifth Avenue. As the only Indian family in the small Pennsylvania town where she grew up, “Brands were the way that I assimilated, it's how I connected with people around me.” After finding success as a director at Victoria's Secret, Grant noticed that the female leaders she worked with were making major compromises in their lives. “They weren't killing it in their personal relationships, they weren't killing it in their families, but they were killing it at work—and they were killing themselves,” she explained. Eventually, Grant grew frustrated that these women were running companies, but not owning them, and grew tired of speaking her mind with little to no change. “I thought, Wait, why am I trying to convince this giant mothership? I should just go create a dinghy and see what happens on my little speedboat.” Then came Lively. “When I came to New York, I said, 'I wanna create a brand for women like me, like others that just really inspire that feeling of passion, purpose, and confidence.'”

For capital, Grant decided to reach out to suppliers directly rather than venture firms, since she knew her product was expensive to make. When deciding on her investors, Grant said: “I just like kind of thought about who do I wanna surround myself with that's really gonna help me propel this business fundamentally?” A key takeaway she learned from the fundraising process? “As women, we don’t know what to ask for,” she said. “It was interesting to me, looking back, no one told me that these were options or these were questions or these are things I should have thought about… but now I realize, you know, we gotta get educated.” 

Tracy DiNunzio’s story looks very different. DiNunzio went to art school and spent most of her twenties pursuing a career as a painter. Her last project for art school eventually became the premise of Tradesy. “I thought, Wouldn't it be cool to leverage this new technology (mobile technology) and how everybody's on their phone to feel like you have a million sisters and always have something to wear,” she recalled. “Then we can stop buying so many things and disposing of so many things and it'll be sustainable and circular and communal and a way for women to connect and do things better.” 

After realizing her idea of an online closet could be a business opportunity, DiNunzio bootstrapped it by sleeping on her own couch and renting out her room on Airbnb. She taught herself the different sides of a business, from coding to marketing to customer service. “We were off to the races and that was 13 years ago that I started it. So it's been a journey,” she said. After a few years of self-funding, DiNunzio started down the venture path after realizing her brand needed a massive amount of capital to scale very quickly. She said: “So over time I ended up raising like $145 million, which is like 145 million heart attacks. And it was always uphill. It was never easy.” During the process, DiNunzio connected with investors who “made life difficult,” but also met supportive investors who would later become her mentors. “So it's not all horror stories. And if you're in a category where there's potential to kind of do like a world takeover, raising that capital can make a lot of sense and really fuel rocket ship growth.” 

Since launching their businesses, all three women have decided to exit their companies and move on to their next big thing. DiNunzio has sold Tradesy to Vestiaire Collective and is now running their North American division. Grant is now pursuing ventures in wellness and Web3, although she needed a bit of persuasion to allow Lively to be acquired. “Fundamentally, I had to take the ego out of the equation and I looked at the opportunity and I was like, Wow, this is what I always said. [Lively] will now live on well beyond me,” she explained. As for Johnson, she sold Create & Cultivate with the company in a strong position after the pandemic. With such a specific product that required capital to grow, acquisition was the “right decision,” she said. Johnson has since launched a venture fund. “And I don't think that a lot of people know that there are so many key players you need to have in the mix and it is a full-time job on top of your full-time job to sell your company,” Johnson explained.  “And so I wanted to be able to provide both money and mentorship to women moving forward and be able to help other women grow, sell, build, businesses.”