Ask HN: Would you sell or diversify your startup equity if you could?

You diversify to retain or safeguard wealth, you concentrate to first create wealth. The second best way to destroy a great investment/ownership position, is to diversify the returns away with other mediocre positions. Conventional wisdom about diversification is bumper sticker investment advice, it's worthless advice without context. It gets repeated generically so often for two reasons: it's easy to repeat to amateur investors for their comfortable digestion and it's safe advice that incompetent investors (bloggers, authors, journalists, talking heads on tv, etc.) can give out everywhere.

Andrew Carnegie was right: "The way to become rich is to put all your eggs in one basket and then watch that basket."

That's also advice that Warren Buffett followed to get rich. He didn't do it through rampant diversification, rather, through intense concentration into a small number of investments that he understood exceptionally well. Nearly everyone on the Forbes 400 list followed that path in one manner or another, with few exceptions. Once you get rich, you diversify to avoid losing it (no need to get rich twice, if you hold onto it the first time; doing it once is hard enough for most people).

Firstly sharepost is curated. You need an interview and to be accepted.

Secondly, most (nearly all?) investment agreements prevent share sales that aren’t approved by the other shareholders. So unless your investors agree to a secondary, you’re out of luck.