I knew a few people that required the company to issue stock certificates so they could then sell them later and obfuscate the cost basis to avoid capital gains. Illegal? Yes. I chose sell, hold a year and pay capital gains on some. In more volatile times, I just sold and took the income tax hit. For me, it worked to *not* focus on or even understand what could have been. I focused on what to invest in once I had it in my pocket. On that front, I chose a lot of blue chip, high dividend paying companies. I bought companies that are in every Walmart cart and in technology that everyone uses. In (early) retirement, I live off the dividends and and get nearly free healthcare. I’ve discovered it is pretty cheap to not work.
That’s awesome to hear. I’m following a similar path. Just need the next 2 years to pan out. Biden’s reign couldn’t have come at a worse time for us.