Tax Strategy · 6 min read · 2026-01-21
The 9-variable equity comp strategy.
Equity compensation builds wealth and concentration risk simultaneously. Nine variables manage both.
Equity comp builds wealth in good times and concentration risk in bad times.
RSU vesting and ISO/NSO exercises create wealth at scale but also produce concentrated single-stock exposure. Tech-employee portfolios commonly become 50%+ employer stock without deliberate management. The resulting concentration is the single largest financial risk.
The nine indicators
The nine variables of equity comp.
Each is a specific decision input. The composite produces a coherent strategy across vesting, exercise, and diversification.
Vesting schedule and cliff
Pattern: 4-year graded typical
Most tech RSUs vest over 4 years with 1-year cliff. Plan diversification around vesting schedule.
Sell-on-vest as default
Pattern: avoid concentration accumulation
Selling RSUs as they vest avoids concentration accumulation. Holding vested RSUs is identical to receiving cash and buying employer stock.
ISO vs NSO tax treatment
Pattern: AMT vs ordinary income
ISOs trigger AMT on bargain element. NSOs produce ordinary income at exercise. Different tax planning.
ESPP discount and holding period
Pattern: 15% discount + qualifying period
ESPPs typically offer 15% discount with 'qualifying disposition' requiring 2 years from offering date and 1 year from purchase.
Concentration ratio relative to net worth
Threshold: < 25% target
Single-employer stock above 25% of net worth represents concentration risk. Above 50%, the household balance sheet is fragile.
10b5-1 plan eligibility and use
Pattern: pre-set sales
10b5-1 plans permit insiders to sell during blackout periods via pre-set rules. Diversification tool for executives.
Tax-loss harvesting on declining positions
Pattern: sell underwater RSUs
Vested RSUs that decline can be sold for tax loss while preserving diversification benefit.
Charitable trust strategies for large positions
Pattern: CRT or DAF
Large concentrated positions can be donated to charitable structures, eliminating capital gains while delivering charitable intent.
Future-grant continuation expectations
Pattern: ongoing equity refresh
Companies refresh RSU grants annually. Plan for continued equity inflow rather than treating each grant as one-time.
Why equity comp creates concentration
Tech employees commonly receive RSU grants worth 20–50% of total compensation. Each vesting tranche adds to employer stock holdings if not sold. Over a multi-year career at a successful company, the holdings can grow to dominate household net worth — 50%+ in employer stock is common at senior tech roles.
The concentration is invisible to most retail because the compensation feels like income (which it is, for tax purposes). The income then sits in employer stock by default. Without deliberate diversification, the resulting concentration represents existential single-employer risk.
Sell-on-vest as the simple default
The cleanest default for vested RSUs is to sell on vesting and reinvest in diversified portfolios. The tax cost is the same — RSUs are taxed at vesting regardless of subsequent action. Selling immediately avoids accumulating additional concentration and converts the income into a diversified position.
The discipline is to set up automatic sale at vesting via the brokerage or to manually sell within a few days of each vesting event. Procrastination is the most common failure mode.
ISO complications
Incentive Stock Options have tax-advantaged treatment but trigger AMT on the bargain element if exercised and not sold in the same calendar year. The AMT can produce surprise tax bills of $30K–$200K+ for tech employees with appreciated ISO grants.
The discipline is to model AMT before any ISO exercise. Exercising and selling in the same calendar year converts the ISO into NSO-like ordinary-income treatment but avoids AMT preference. The trade-off depends on holder's specific tax situation and conviction in the underlying.
ESPP — the under-claimed benefit
Employee Stock Purchase Plans typically offer 10–15% discount on company stock with quarterly purchase windows. The discount is essentially free money for employees who participate. The discipline is to participate fully (typically 10–15% of salary) and sell shortly after purchase.
The 'qualifying disposition' rules can produce favorable long-term-gain treatment if shares are held 2+ years from offering. Most tech employees sell shortly after purchase to avoid concentration accumulation; the qualifying-disposition strategy is for holders willing to bear single-stock risk for tax efficiency.
Get the nine, every Monday.
Free weekly digest. The only U.S. equity letter that publishes a name only when nine independent signals align.
Common questions
Questions.
Should I always sell RSUs on vest?
For most tech employees, yes — to avoid concentration accumulation. Exception: high conviction in employer's specific outlook plus already-diversified balance sheet.
How do I exercise ISOs without AMT?
Exercise and sell in the same calendar year (creates ordinary income, no AMT). Or exercise small tranches annually below AMT threshold.
What's the best ESPP strategy?
Participate at maximum percentage. Sell shortly after purchase to capture discount and avoid concentration. Re-invest proceeds in diversified portfolio.
How does this affect tax planning?
Equity vesting creates ordinary-income spike in vesting years. Plan tax-loss harvesting and charitable gifting around vesting calendars.
What about pre-IPO equity?
Different framework. QSBS qualification, 83(b) elections, secondary market liquidity all matter. Specialized advice essential.
Should I exercise NSOs early?
Generally no — exercise creates ordinary-income tax without realizing actual cash. Exercise close to or at sale to align cash flow with tax.
One name. Sometimes weeks of silence. Always with conviction.
Free weekly digest. No credit card. Unsubscribe anytime.