Anonymized case study · Illustrative only

A Meta Staff Engineer with $2.3M in concentrated stock

One California-based engineer's RSU position grew over six years to dominate their net worth. Here's what selling would have cost — and how a coordinated plan brought that number down meaningfully.

The situation

Stock value: ~$2.3M (single-stock concentration in their employer's equity)
Cost basis: ~$400k across multiple grant tranches
Embedded gain: ~$1.9M
State: California (highest state LTCG burden — 13.3% treats capital gains as ordinary income)
Household income: ~$800k (top federal LTCG bracket)
Charitable giving: ~$50k/year, recurring

What a naive sale would have cost

Federal long-term capital gains tax (20%)$380,000

Net Investment Income Tax (3.8% on investment income)$72,200

California state tax (13.3%)$252,700

Total tax if sold at once~$704,900

That's about 37% of the gain. Their $2.3M would have netted to roughly $1.6M.

What a coordinated plan looked like instead

Rather than one transaction, the position was unwound across four mechanisms working together:

~40% — Long/short direct indexing SMA. A managed account that books tax losses on individual stocks alongside the user's gradual sales. Over five to seven years, those losses offset a meaningful portion of the embedded gain on a tax-neutral basis.
~30% — Exchange fund. The contributed shares went into a pool with other concentrated holders; the user got a diversified basket back without triggering a sale. Seven-year lockup applies.
~20% — Donor-advised fund. Since the user already gave roughly $50k/year, the appreciated stock went directly into a DAF. The tax on that slice disappeared, the user got a current-year deduction at fair market value, and granting to charities runs on their own schedule.
~10% — Protective collar. Caps the downside on the slice still held while the rest of the plan plays out over two to three years.

Illustrative outcome

Naive sale (one transaction)~$704,900 in tax

Coordinated approach (range)~$180,000 – $240,000 in tax

Illustrative savings~$460,000 – $525,000

Illustrative scenario only. Actual outcomes depend on factors not captured here — other holdings, future income trajectory, charitable goals, family situation, and timing. Not investment, tax, or legal advice.

What this took

Picking and combining strategies isn't a one-time decision — it's a multi-year sequencing problem that depends on the user's full picture. The 30-minute Strategy Session is where Sumeet builds the actual mix; this case study is to show the shape of what's possible.

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