Vertical 02 of 06
Concentrated Equity & Portfolio Capital
How do I de-risk single-stock exposure and engineer tax-sheltered wealth?
The core problem
Engineers hold company stock because it keeps going up, while their salary, bonus and unvested equity are tied to the same employer. That is double jeopardy: one bad quarter cuts income and liquid net worth together. The fix is deterministic — price the concentration, then decide where the proceeds live.
What this vertical answers
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01
The RSU vest fallacy
Shares taxed as ordinary income on vest and then held are economically identical to taking the cash bonus and buying company stock at today’s price. If you would not buy it with new cash, auto-selling on vest is the same decision in reverse.
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02
10b5-1 plans and systematic de-risking
How directors and staff engineers schedule quarterly sales without insider-trading exposure — and why the plan has to be adopted while you are not in possession of material information.
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03
Exchange funds vs. direct indexing
When a $500k+ single-stock position justifies a seven-year exchange-fund lockup, and when systematic tax-loss harvesting in a separately managed account is the cheaper diversifier.
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04
Asset location and the $72k ceiling
High-dividend, REIT and bond exposure belongs in tax-deferred; high-growth equity belongs in Roth; the harvested core sits in taxable. The Mega Backdoor Roth is how the Roth bucket gets funded past the elective deferral cap.
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05
Secondary tenders and QSBS
A tender offer is a price, not a verdict. Model the haircut against the risk-adjusted IPO path, then check whether §1202/§1045 rollover treatment survives the transaction.
Flagship engine
RSU Hold vs. Sell & Mega Backdoor Roth Simulator
2026 IRS statutory model quantifying employer concentration risk, double-jeopardy exposure, and $72,000 Section 415(c) Mega Backdoor Roth asset allocation.
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