Did you consider moving states to avoid high income taxes (California, New York) when you sold your company?
No, but I do think about it now.
When I started my first company in California, I had $0 in the bank anyway. You don’t think about it. Everything is upside. I couldn’t have founded it anywhere other than Silicon Valley, anyway. I did buy my founders stock to get long-term capital gains, but that was it.
When I started by second company in California, I thought about it a little more. But taxes were lower then than today, and again, I needed to build it in Silicon Valley. However, I began to think of M&A returns on an after-tax basis.
Today, after two exits — I think about it a lot. Probably every week. Federal + California taxes on both capital gains and ordinary income are at a personal maximum for me. I think about every financial action I take in terms of tax inefficiency.
And today, right or wrong, I would certainly invest — and hire people — more aggressively if tax rates were lower today. You can argue this isn’t rational, but what I can honestly tell you is it true.
I would even consider moving. Now, at least.