An Early Investor’s Postmortem of The Wing

a Dall-e variation on a variation on a variation of an image of The Wing, warped with the canva wobble filter

“I remember you mentioning The Wing before it opened, and I am right now enjoying my first morning working there (I never want to work anywhere else). It makes me feel productive, self-assured, and feminine all in a way I didn't expect. Thought I'd share...”

That was a note that I got from a friend back in September of 2018. She knew I was a seed investor in the company.

For a good long while, it seemed like a fund-returning investment. I wasn’t privy to the financials at the time, but by the end of 2019, I had penciled out a guess that they were at a $50 million run rate—or at least on a clear path to it. Audrey Gelman was on the cover of Inc magazine, visibly pregnant. Sequoia, the top venture capital firm on the face of the earth, put in a growth round that valued the company at close to half a unicorn.

Things looked more than great. It looked like I had invested in a company making a generational impact. I imagined a future Wing media arm with a TV channel, a venture capital fund…

…and then it all came crashing down.

So, what happened? And why am I writing about it?

I’m writing because a lot of how the story played out obscures real lessons to be learned here, oversimplifies the issues, and (Read more...)