Someone with a $100m exit reach out yesterday

They were going to split the payment in two, with the first in December and the next in January.

I’m begging them to kick the whole thing to January.

From a tax‑planning perspective, that date shift is a big deal.

If you close in late December:

• The gain hits your current tax year
• You have days or weeks to react
• Anything you do after 12/31 (loss harvesting, REPS, charitable planning, etc.) generally can’t offset that prior‑year gain

You’re basically stuck with:

• Whatever structure you had going in
• Limited options to soften a 7‑ or 8‑figure tax bill

If you close in January:

• The gain hits next year’s return
• You’ve got 12 full months to plan before you file
• You can deliberately build a “tax shield” around the gain

That gives you time to:

• Fund a tax‑aware long/short SMA and let it harvest a very large amount of losses over the year
• Use tax‑aware hedge funds and real estate to realize ordinary and passive deductions
• Coordinate charitable strategies, Roth conversions, and entity moves in the same tax year as the gain

On a $100M+ outcome, the difference between “we had 3 weeks” and “we had 12 months” can easily be 8 figures over time.

Not everyone can control their closing date.

But if you have any say in December vs January, it’s not just a timing preference. It’s a planning window.

If you’re staring at a 7‑, 8‑, or 9‑figure liquidity event in the next 12–24 months and want that kind of runway used intentionally – long/short, hedge funds, real estate, charitable, estate – that’s exactly what I build for clients.