Sophia Amorusothe the creator of Nasty Gal and Girlboss, has started a movement, empowered generations of women, and done a victory lap of entrepreneurs — the latter of which she doesn’t necessarily recommend to other founders because “it’s a distraction.” It also raised rounds, ran out of venture capital funding, filed for bankruptcy and was sued.
“I saw the whole spectrum of what worked and what didn’t,” the entrepreneur said in an interview with TechCrunch. “It’s the not-so-great things that can often help founders anticipate or simply avoid.”
Her high-profile and rocky experience in the Silicon Valley spotlight finally gave Amoruso the operational experience she needed to launch her own investment firm, Trust Fund.
The Trust Fund, named ironically, Amoruso says, because “nobody gave her anything,” is launching with a goal of $5 million, aiming for a check size between $50,000 and $150,000. She’s already received checks from the who’s who in tech. Featured investors include a number of a16z partners such as Marc Andreessen, Andrew Chen and Chris Dixon, entrepreneur Eve Williams and icon Paris Hilton, as well as backing from investors Ryan Hoover and Sarah Kunst of Cleo Capital.
The trust fund wants to back digital consumer companies and has already invested in an undisclosed workplace collaboration tool. Amoruso has been an angel investor for four years and has invested $1 million of her own capital in 23 startups, including Pipe, Liquid Death and Public.
“As a small fund, I’m not necessarily looking for diamonds in the rough,” Amoruso said. She noted that other funds have the resources to do more due diligence and legitimize companies, while the Trust Fund will somehow look for social proof. She prefers lean companies that make money and act like they’re trapped.
Along with the launch, Amoruso tells TechCrunch that she’s committing $1 million from the fund to people outside her network. Accredited investors are invited to apply to write checks, between $2,000 and $10,000, to the debut investment vehicle.
She looks for diversity on her desk — “because there are a lot more women who can write $2,000 checks than there are women who can write $200,000 checks. Community upliftment aside, it has no mandate for diversity when it comes to portfolio building.
“I plan to invest in men and women, and everything in between.” And if nothing else, like, why not invest in the privilege and ride in a guy’s coat?” Amoruso said. “As a woman, why wouldn’t I want to invest in an advantage that a man has, like, feel free to put it out there – it’s true.”
While the entrepreneur is certainly looking outward to fuel her next venture, she’s also looking inward. Much of the Amoruso brand is associated with the Girlboss, a word she coined to describe independent, entrepreneurial women. Girlboss became a memoir, a company, a Netflix show, and an empowerment movement—before it devolved into a sexist trope used to describe controversies surrounding high-profile women in leadership who often step down from their positions.
Amoruso is no exception to this instability. The entrepreneur left her company, Nasty Gal, in 2015 after being embroiled in multiple lawsuits, as well as difficulty thinking about growth at any cost. “I overvalued Nasty Gal, we were $12 million profitable when Index valued us at $350 million.” Expectations that the next increase would be $1 billion plus were unrealistic.
When asked about Girlboss, Amoruso said it “was a big part of my story. But also … at what point can I tell a new story?”
The entrepreneur sees her past as both a fading story and a competitive advantage, adding that she “doesn’t consider honesty a risk.” Among the attributes the Trust Fund touts as added value, she included: “building a no-bullshit culture because we’ve done it wrong… and right” and “navigating the media when they love you and when they don’t.”
What is clear is that, much like her past ventures, the Amoruso brand is what keeps people betting on her again. She has more than 120,000 newsletter subscribers, over 100,000 Twitter followers and more than half a million Instagram followers. It’s a following he believes he can use to “evangelize” his portfolio of companies, akin to celebrities but also with the operational experience that founders value during a crisis.
A16z’s Andrew Chenwho says he personally invested in Amorus’ new fund, described her as “an 0-1 founder who has seen and done it all…[there are] very few people who have done all this and want to dedicate their careers to helping the next generation of founders.”