An advisor booked a 1:1 consult with me last week.
He’d been managing $1M for a couple.
They were considering moving the other $5M of their assets… but weren’t convinced yet.
Here’s what we did together in 30 minutes:
Their situation:
- Big, concentrated stock positions
- Multi‑million dollar IRAs creating a future tax bomb
- Expensive debt on a rental property
- Already living off largely tax‑free rental income
Most advisors would respond with “let’s diversify a bit and rebalance.”
Instead, we built a tax‑aware story:
1️⃣ Concentrated stock
→ Use a tax‑aware long/short SMA to diversify quickly and tax‑neutral.
2️⃣ Large IRAs
→ Add tax‑aware hedge funds in taxable accounts to generate ordinary deductions.
→ Use those deductions to execute Roth conversions with little or no net tax.
3️⃣ Rental debt
→ Use a box spread loan secured by the portfolio to refinance higher‑rate debt,
instead of liquidating appreciated securities.
4️⃣ Already-tax‑advantaged real estate
→ Keep lifestyle funded by rentals, and let the restructured portfolio focus on growth and tax alpha.
Then we worked on how he’d present it:
- The sequence of the meeting
- The language to use with the couple
- The documents to show the CPA (redacted K‑1s & tax code references)
The result: he’s walking into that next meeting with a clear, compelling plan that actually solves their problems. I’d be very surprised if that extra $5M doesn’t move.
We knocked all of this out in a 30‑minute consult for $500.
If that meeting lands the way it should, he’ll likely add $5M+ in new AUM from one existing relationship. And the real winner is the client, who now has a path to save millions in taxes and compound their wealth faster with the same pool of assets.
If you’re an advisor sitting on clients with:
- Concentrated stock
- Large IRAs / RMD issues
- Complex real estate and business income
…and you know there’s more value on the table but you’re not fully confident in the mechanics or messaging, that’s exactly what my 1:1 consulting is for.