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What did Nasty Gal founder Sophia Amoruso learn from failure?

Amoruso, now the founder and CEO of Girlboss, says she told investors that her new company is “Oprah for millennials and Supreme with boobs.”

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Girlboss founder Sophia Amoruso takes a close-up picture with her phone of a wall mural at a Girlboss rally. Cindy Ord/Getty Images for Girlboss Media

When she was 22, Sophia Amoruso started the women’s fashion brand Nasty Gal. Fast-forward 10 years, and she has stepped down as Nasty Gal’s CEO and watched that company file for bankruptcy — not to mention, she’s been through a divorce and had to contend with critiques of her life story as portrayed in a short-lived Netflix show.

“A decade later, in the afterlife, it feels like I can’t be killed,” Amoruso said on the latest episode of Too Embarrassed to Ask. “It feels like a video game.”

She told Recode’s Kara Swisher and The Verge’s Lauren Goode that, in hindsight, she raised venture capital money too eagerly and hired too quickly, lessons she’s applying to her new company, Girlboss. She has also realized that being CEO is “not that fun of a job” and is taking stock of what she does best: Making media, not managing other executives.

“I was a young, naive founder,” Amoruso said. “I think I thought I could hire C-level executives who would just write their job descriptions for themselves, hold themselves accountable. At the end of the day, I think scientifically we’ve proven that an observed object behaves differently than when it’s not observed.”

“It doesn’t mean I lead the company now, breathing down everybody’s necks,” she added. “[But] I have a firmer grasp today of the way the company spends its money, when the company becomes profitable, how ready we are for a series A … all the things that I need to back into now and plan for and understand what my success metrics are that are reasonable and not pulling numbers out of the sky.

You can listen to the new podcast on Apple Podcasts, Spotify, Pocket Casts, Overcast or wherever you listen to podcasts.

On the new podcast, Amoruso explained that the slide deck for Girlboss described it as “Oprah for millennials and Supreme with boobs.” Through written pieces, videos and a podcast called Girlboss Radio, she’s hoping to reclaim the power of “advice for women,” which has been dominated by fashion magazines.

“I don’t want to knock Cosmo, but historically, women have been spoken to in a way that is kind of fearmongering,” Amoruso said. “‘This is what you need to be to get this.’ Women, it feels like we’re beginning to write our own history and our own version of what success can look like for ourselves, individually.”

And there’s an audience ready and willing to take better advice than “look cute and smell good,” she said. Girlboss has also hosted several live events, called Girlboss Rally, at which 50 percent of surveyed participants were business owners and 100 percent wanted to be, Amoruso said.

“I used to say at Nasty Gal, we had ambitious customers, but I think I was flattering myself,” she said. “This is an ambitious generation. These women have access to more than we ever had. The opportunity feels like it’s at our fingertips.”

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