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I had a lot of SBC over more than 20 years at a large tech company. Upon vesting and exercise, the Broker just withholds the equivalent number of shares to satisfy the estimated tax.
That is the typical way they do it. But it isn't the only way. There were a few times that I opted to pay the taxes with cash instead of with shares. One time, maybe 15-20 years ago, my company was hard up for cash, so they gave us stock in lieu of bonus that year. At the time, the stock was really low due to the imminent threat of bankruptcy. So they ended up giving us LOTS of shares. Instead of selling those "cheap" shares, I opted to keep them and pay the tax using my own cash. Turned out to be a great decision because the company avoided bankruptcy, got some last minute financing, and those shares were worth 10 to 15X when I finally sold them sometime later after the company was on much firmer financial footing.
