What does it feel like when the company you work at goes IPO?
At least for me, it felt great for about a day. Big bottles of champagne, recognition “we did it”, etc. IPO’ing truly is one of the most iconic Silicon Valley and startup moments. It is special. But then, the next day … everyone sort of goes back to work. Although, it’s different afterwards. People act differently. The goals are different. Everything is at least a little … different.
Then odd for about a month. When can I sell? What do I do? How do taxes work on options? I’m supposed to figure this out and do regular work, too? Aunts and Uncles calling, FBs from old classmates. People you know grab you at restaurants. You’re a genius now. No matter what your role was, or when you joined.
Then distracting for a year. The stock price went down 20% this quarter? It’s hopeless. This company is struggling. The stock price went up 30% this quarter? What do I do?! Do I sell? Would it be stupid to sell? What do I do?
Then, sometimes, 6–12 months out … it’s a slight bummer. Because then, you know what the options are worth — there’s no more mystery of what you’ll make — and the start-up phase is … gone. The mystery is gone, at least on the economic side. For early-stage folks especially, the struggle and not knowing is the key part of the journey. If you don’t love your boss, your team, and your mission … you sometimes want to move on after this. The best companies know this and do what they can to manage it. And they know some of the earliest folks will sort of move on after this. To the next highly uncertain, but potentially amazing, journey.
I’d like to go through it just one more time.