How to Mitigate Taxes & Diversify a Large Stock Position: Part 2

Five people. Five completely different net worths, ages, and family situations. And every single one of them is sitting on a stock position that's grown so large it's now the single biggest risk in their financial life. In Part 2 we're taking the strategies we learned about in Part 1 of this mini-series and we're running it through five real case studies with real numbers, so you can see exactly which strategies fit different situations, and more importantly, why the "obvious" answer is wrong more often than you'd think. More specifically, I discuss: 5 case studies for diversifying and managing taxation Selling stock, direct indexing and using charitable giving strategies Avoiding unnecessary taxation from mutual funds Diversifying after utilizing the Net Unrealized Appreciation (NUA) strategy for stock in 401(k) and ESOPs Managing continuing awards of Restricted Stock Units (RSU) Resources From The Episode: Retired-ish Newsletter Sign-Up Ask a Question Get Show Notes Here   Key moments: (02:20) Case study 1: Combine selling, direct indexing, and charitable tools (11:40) Case study 2: Sequence charitable giving and direct indexing (16:16) Case study 3: Avoid unnecessary taxation from mutual fund distributions (24:24) Case study 4: Use NUA and patient diversification (33:28) Case study 5: Manage a moving target of employer equity (40:30) Match diversification to each person's timeline and goals (42:38) Prioritize diversification over avoiding taxes