If I had multiple lots of stock at different price points, and my goal was to diversify a portion of the holdings, I would prioritize selling the lots with the largest gains last in most cases.
If those were the only lots I held, and my goal was diversification, I would sell but look for opportunities to offset the capital gains (ie maybe from losses elsewhere). This could change depending on if we are talking about <$10,000 vs $100,000+.
Thank you so much for doing such detailed analysis and sharing it.
Andre
Great deal of detailed work here. Thank you. You've reduced my anxiety level around occasionally missing v+2 for sell !
How do you feel about selling some units under $100 while the stock is 5x higher recently?
If I had multiple lots of stock at different price points, and my goal was to diversify a portion of the holdings, I would prioritize selling the lots with the largest gains last in most cases.
If those were the only lots I held, and my goal was diversification, I would sell but look for opportunities to offset the capital gains (ie maybe from losses elsewhere). This could change depending on if we are talking about <$10,000 vs $100,000+.