So I finally did a thing I've been being lazy about...
Prior to this week of the stock I held a VAST majority was in the company that I worked for until recently. Combination of RSUs I got there, plus a very lucrative ESPP program. (add in that my RSU's priced in at the absolute low of the covid crash, and the company has been on essentially a very solid page up and to the right since and it's been a very nice windfall.) It was literally 90% of the stock holdings I had. I took the first step to finally diversity. After consulting with a wealth management person , decided to start. But they looked over things with an eye to absolutely minimize tax impact. Ended up deciding on a tax loss harvesting fund strategy. Essentially you put money into the fund, a place then buys all the stocks to basically build you own "personal ETF". Difference being you own all the individual stocks. They manage all the buying and rebalancing. They also focus on selling the losers to harvest tax losses when time to rebalance/etc so generates tax losses to offset as many profits as possible. So this year they estimated how many losses I had across my other stocks, advised the loss harvest sells there, plus I sold a chunk of the former company's stock , the losses should offset most of any actual tax liability the sell would generate.
They now take that and buy all the individual holdings. Now if there are losses they'll harvest them in December of this year, and then when the timing is right next year. Based on the expected coverage that guides if I want to divest more next year and use any tax losses to offset.. rinse and repeat. Apparently this is a strategy a lot of people are using and the government doesn't like, but it works and it isn't illegal.
Drawback, costs 1% per year in fees. I'm going to see how this plays out. Initial sell was around 15% of my previous company stock I held. When the transaction settled and before it was re-invested for around a day I had more in cash on hand than I think any person in my family has ever had.... ever. heh.
Now I look in the account the money moved into and I have 379 individual stock positions , I search down and... yeah.... it bought a little of the company stock I just sold. heh.
