I haven’t seen any mention of how to approach charitable donations with maximum badassity, so I thought I’d chime in with my own example. I use stock that I purchase through my employee stock purchase plan - which is at a minimum of a 15% discount from the market price when I buy it - and then transfer the stock to a 501c3 organization. The non-profit gets the full value of the stock, I get to deduct the full value as a donation, and yet I never pay income tax on the difference between the cost basis and the price on the day of the transfer. In my best example, I transferred stock that I purchased for about $4,000 that had grown to be worth $10,000. And then my company matched the $10,000! I know I would reach financial independence sooner if I kept the money for my own stash, but honestly it felt greedy to keep the money when it could multiply into so much more good elsewhere.
