We all want to believe we “knew” our company was going to the moon.

But a $5M+ single‑stock position in your 20s isn’t genius. It’s concentration and luck.

Here’s what I told him I would do in his situation:

1️⃣ De‑risk aggressively

If you’re in your 20s with multi-million wealth and a long career ahead, the game is simple:

Turn one lucky bet into a durable balance sheet without detonating your tax return.

A long/short SMA lets you:

• Sell 90% of the stock day 1
• Track (or beat) the index
• Harvest capital losses for years

2️⃣ Add tax‑aware hedge fund exposure

Layer in tax‑aware hedge strategies that:

• Diversify away from equity risk
• Aim for double-digit returns
• Generate ordinary deductions that can help offset W‑2 income each year

3️⃣ Add tax‑aware real estate

Take advantage of preferred equity deals today with:

• Mid-teen return profiles
• Current yield shielded by depreciation
• Long/short SMA losses available to help offset recapture on the back end

4️⃣ Super duper mega tax-free Roth conversion™

Use this simple strategy to get all of your retirement assets into Roth IRA

• Pair realized deductions from tax‑aware hedge funds
• With converting pre‑tax balances to Roth

You’re buying decades of tax‑free growth while you’re still young.

5️⃣ Add Privates (in the Roth)

Once the core is stable:

• Put private equity, infrastructure, and credit in the Roth
• Seek diversified, multi-style exposure
• Let it compound untouched for decades

This is how wealth becomes multi-generational.

If you’re in your 20s or 30s with a few million tied up in one stock and no written plan to get out of it tax‑aware, this is exactly what I help people build.