In my latest video, I walk through how we redesigned a $20 million concentrated stock portfolio using synthetic variable prepaid forwards (synthetic VPFs) to:

• Reduce single‑stock risk without selling the shares

• Unlock meaningful liquidity without triggering an immediate tax bill

• Transition into a more diversified, tax‑aware portfolio over time instead of all at once

I also explain how several tax-efficient strategies can work together as part of a broader plan, including:

• Capital losses from the box spread loans

• Capital losses from tax-aware long/short SMAs

• Capital gain deferral through qualified opportunity zones

• Donating appreciated stock opening the door to Roth conversions

If you’re sitting on a highly appreciated concentrated stock position, I hope this gives you a few ideas for how to diversify more thoughtfully.