Subject: De-risk a bit?
I've been a lazy, mostly "know-nothing" investor in Berkshire since the late 1990s. I ran a small business for about 28 years, and basically invested all the earnings of that business into Berkshire when I had the cash to do so. I retired around 2009, and my wife and I have been living off that Berkshire investment since. Our portfolio is currently 85/15 Berkshire/t-bills.

I thought I was well prepared mentally for the CEO transition, but my stress levels have gone up considerably since CM passed and now that WB has basically retired. So I *THINK* I'm interested in de-risking a bit and selling maybe half the Berkshire position, but I don't have a good plan on how to do that, or if I should. I will also admit the current US political environment is causing me much stress and has thrown me out of my comfort zone.

My first thought was to just sell around $600k per year to keep cap gains under 15%, but because of the position size that will take many years and could introduce more risk/stress/worry.

So I'm kind of crowd-sourcing for some ideas. I figure I have these options, but want to hear about more options that I'm not thinking about:

1. Do my multiple year 600k sale plan, which could take advantage of share price gains if new management does well, but will be a long drawn out process that will cause me more worry and stress. I will then try to invest the proceeds over time into some "easier for my wife to manage" index.

2. Do a big, one time divestment of Berkshire, which will trigger massive cap gains taxes and a large increase in income and taxes from interest on the new cash. Then I will have to worry about how to deploy that large chunk of cash. I would like to index it, but I want to time that correctly. I hate this plan as I write this. 😬

3. Just let it ride and do nothing, and hope for the best. Selling off small chunks as we need the cash or when the share price is richly valued (like I have been doing), and take advantage of the step up basis to my wife when I expire, and then to our kids when she passes. This seems like the easiest process and better tax-wise, but we would retain our very large "one stock" risk. Am I overthinking our large one stock risk? I was always pretty sanguine about this when CM and WB were running things, but now I'm not so sure.

Details:

We currently have about 10-11 years in cash and t-bills that we use for living expenses.

We spend around 2% of our portfolio annually.

We are US based and have a very low cost basis in Berkshire.

We live in a low cost state tax-wise, with no state income taxes but high property taxes.

We have two working age kids with good jobs, and would like to pass some on to them at some point.

Wife is not interested in investing and has deferred to me for all these years, and I'm a bit embarrassed I don't have a better plan set up for her. She is in better health than me and will almost assuredly outlive me. This is one of the big reasons why I think I should de-risk, because if Berkshire blows up, or becomes the next GE or whatever, I will have done her a massive disservice.