Girlboss Rise and Fall

A story about how Sofia Amoruso's Girlboss company went from venture-backed startup to a lean media operation under new ownership.

"Sofia started Girlboss about 6 years ago and built up this massive following with events, podcasts, and a social network. I met her when she was first starting it after her previous company Nasty Gal had a big flame out. She had built Nasty Gal into an amazing business doing $30 million a year in online clothing retail. She didn't need the money but ended up raising venture capital to take some money off the table.

The venture investors pushed her to take big risks and start retail stores. It all blew up - a horrible story where she had a good thing and risked it. Fresh off that experience, she started Girlboss saying she wanted to bootstrap it. We invested, but she ended up raising venture capital again and decided to build expensive projects like a social network and app.

It wasn't working at venture scale so she sold it to Attention Capital. They focused on events but then COVID hit and the numbers didn't make sense - they were burning too much money. They approached me about buying it. We looked at the assets - 2 million social followers, huge newsletter, massive podcast feed - and figured we could run it with just 5 employees instead of their venture-scale cost structure.

We started with basically one person doing newsletter, one doing podcast, one doing social and said we'd hire more as we sold more ads. We ran it like a bootstrap business. Sofia was nervous when we bought it, didn't want us to embarrass her, but she's been really happy with what we've done."