Earlier this month, I headed out east to the Hamptons with Female Founders Fund. The venture capital firm founded by Anu Duggal hosts a gathering each summer for the founders in its portfolio and others who make up the female founder universe. I was there to moderate a panel about what really happens after a founder sells their company. The moment when they look at their bank account and see a few more zeroes than usual, their biggest lifestyle changes since, how securing an exit changed their relationships with their friends and family—the real stuff. Sadly, the conversation was off the record so I can’t share too much more. But one theme translated to the rest of these three days in Montauk: the rise of the second-time founder.
On my panel were Gwen Whiting and Michelle Cordeiro Grant. Both sold companies, Whiting the cleaning brand the Laundress to Unilever (which didn’t go as she expected—my story on that saga is here). Cordeiro Grant sold the lingerie brand Lively to Wacoal for more than $85 million. And both are now building new brands, Whiting the cleaning club the Fill and Cordeiro Grant the energy drink Gorgie.
They’re hardly the only ones. Other second- or even third-time founders among this cohort include Mariah Chase (sold the plus-size brand Eloquii to Walmart; is now building the retail tech startup Ekyam.ai); Bobbi Brown (who of course went from her namesake brand to Jones Road Beauty, as I wrote about last week); retail and tech vet Julie Bornstein (sold The Yes to Pinterest; is now building fashion tech platform Daydream); and Audrey Gelman, who has moved on from the Wing to her hospitality business the Six Bells. Female Founders Fund itself is now on its fourth fund, with a total of $140 million in capital under management; Chase was the first founder that Duggal invested in twice.
“It doesn’t get easier the second time,” Bornstein told me. “You either make new mistakes or you can’t help it, you still make the same mistakes.”
Some founders on the second go-around choose to self-fund and avoid the pitfalls of venture capital. Bornstein took the opposite lesson; “I realized how hard it is to raise again while you’re still finding product-market fit,” she says. So she raised more than she immediately needed—$50 million—as a seed round. Another practical tip: this time, Bornstein waited longer to hire marketing talent. After all, if the product isn’t up to snuff yet, there’s nothing for them to market. And she gave away more equity to her employees this time; at her prior company, she’d just followed industry standards for how much equity to share. Now she realized, “I don’t have to follow any rules, I can do it how I want.”
Another pair of second-time founders are Erica Cerulo and Claire Mazur. They were behind the indie ecommerce platform Of a Kind, which sold to Bed Bath & Beyond, and are now building 831 Stories, a trendy romance publisher that is tapping unexpected talent to write romance novellas. Their approach, with signature minimalist covers, is bringing new audiences to romance, and they inked a first-look deal with Hulu.
Even though Of a Kind eventually shut down under Bed Bath & Beyond, the outcome was still critical to building 831 Stories today. “We’re able to go to people, while starting a new business, and say we sold our first business to a Fortune 500 company,” Mazur says.
And it’s easier now to weather the ups and downs. Cerulo and Mazur built Of a Kind in their 20s; now they’re in their 40s. “We worry a lot less,” Mazur says. “Disasters happen every day. That is part of building a business. Nothing feels as much like a crisis as it used to.” “There’s a certain amount of uncertainty we’re more comfortable with now,” says Cerulo. “It’s less existential.”
Emma Hinchliffe
emma.hinchliffe@fortune.com
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PARTING WORDS
"Stepping into shoes that are enormous and pink and six inches tall can be scary."
— Lexi Minetree, who plays a young Elle Woods (aka Reese Witherspoon) in the new Legally Blonde prequel and Prime Video series Elle
