I Quit 7 Days Before My Shares Vested

The decision just cost me $60,100. Here’s what not to do.

Photo by Robert Bye on Unsplash

9 years ago I joined a tech company that promised to democratize its industry.

It had all the tell-tale signs of a start-up that would make it — A high burn rate but a seemingly replenishment of capital, hungry recent graduates, ping-pong tournaments, beer on tap, art murals on the walls, a nauseating company chant, and a healthy dose of office hook-ups.

I was 24 at the time and proud to join the company as lucky employee number 100. During my time there, the company grew rapidly, nearly tripling in headcount.

I left exactly 7 days before my shares vested. The company went public last week and the decision cost me $60,100 as of the closing bell on Friday.

I always said I live with no regrets. Now I feel like I’d be lying. How did I end up here? And how would someone else in a similar position avoid the same fate?

To understand what happened, we have to go back to November 2012 when I received the job offer.

I drank the cherry kool-aid for the first 6 months. I had a compassionate boss, I was learning more about marketing, and had made new friends.