When most of your net worth is tied to a stock of a single potentially volatile company like UBER, you sure as hell want to sell that off and diversify your por

When most of your net worth is tied to a stock of a single potentially volatile company like UBER, you sure as hell want to sell that off and diversify your portfolio. He's not involved with the company any-longer, he has no reason to keep his stock. If he was still in-charge I get that you want to display confidence in the business and keep the stock. TLDR: Most of your net worth in a single stock is insane.