Has anyone ever regretted selling their equity too early? I’ve been tempted to step back and take some chips off the table, but the idea of watching someone else steer what I helped build feels strange. I’m trying to balance financial security with pride of ownership. How do you know when it’s time to cash out?

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Yes. Not mine, but my wife's. Sold a bunch of her equity in Meta at $90/share. Now it's $700+ 🤦

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Your equity allows you to steer things? You are in a true partnership then. Mine is useless to steer anything.

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No big4, no Acn, no witch (if that is the right acronym). And yes, I expected it to be different.

If the financial and business benefits of letting someone else steer are less than the value you will accrue steering it, you should not sell. If you sell partially, and the net outcome is better than holding on …..

That’s the sort of framework. Best of luck. Make it a pure robust forecasting decision.

I thought the question was related to equity owned in a consulting/accounting firm —- maybe I was wrong.

In two past companies, I waited too long to sell equity, and didn't make the same returns I would have in the market. So now I try and sell at least 50% a year.

My first company IPO’d at $18, climbed to $35. I sold at $10 and it dropped to 35 cents within 6 months. It taught me the importance of diversification. I have also come to realize I enjoy the rush of the start but not the ongoing management and status quo.

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