If you’re sitting on a big concentrated stock position, this is what I’d be looking at:

Synthetic VPF - a combination of a collar and a box spread loan to protect downside, maintain some upside, and get ~ 80% of the positions value in cash. The interest on the loan is treated as a capital loss which can offset gains on the stock.

Direct indexing - if you are going to invest in the stock market, you should consider direct indexing so you can harvest some capital losses while you do it. These losses can offset gains on the concentrated stock.

Tax-aware long/short - if you want to try and beat the market and potentially harvest more losses in the process, this solution is worth considering.

Opportunity zones - can buy you 5 years of deferral, 10% reduction in the capital gain, and a whole lot of potential appreciation and bonus depreciation that gets stepped up at the end of 10 years.

QSBS - always check if your company is eligible, especially after the enhancements that were made.

The optimal approach is going to be different for everyone because there are pros and cons to each. They also are not mutually exclusive and you’ll likely want a combination of them.