How to Mitigate Taxes & Diversify a Large Stock Position: Part 1

You've watched one stock turn into more money than you ever expected. And now you can't bring yourself to sell it — because the second you do, the IRS gets a check with a lot of zeros on it and you come to the realization that you are not going to receive all of that money you've been looking at on paper all these years. But on the flip side you're also wondering how that money can change your life and all the things you can do for you and your family. In this episode, we're talking about what that fear of taxation can actually cost you, and some ideas to help you take risk off the table and mitigate the inevitable tax bill. More specifically, I discuss: Why a concentrated stock position carries more risk than you think Worry more about taxes from selling or a sell off in your biggest stock position? Strategies to defer taxes or diversify a concentrated stock position Direct indexing and exchange funds Opportunity zone funds Charitable giving strategies for large, embedded stock gains ⏱️ Chapters: (04:09) Why a concentrated position is sneakier than it looks (09:37) Which is the bigger threat: taxes or concentration risk? (11:41) Thought experiment: selling today vs. waiting and potentially losing value (14:46) The biggest misconception: taxes vs. concentration risk (17:35) Strategy 1. Just sell it (18:56) Strategy 2. Hold on to it until death and receive the step-up in basis (21:10) Strategy 3. Gifting to family (25:23) Strategy 4. Direct indexing (31:04) Strategy 5. Charitable giving   Resources: Retired-ish Newsletter Sign-Up Get Show Notes Here