Marcus

Early Employee at OpenAI

ISOs, RSUs & IPO Planning

Chapter 1

Their World

Marcus joined OpenAI as employee #47. What started as a bold career bet is now worth more than he ever imagined. His equity compensation is complex: ISOs on multiple vesting schedules, RSUs from a recent refresh grant, and the looming question of an IPO. He spends late nights running scenarios in spreadsheets, wondering if he should exercise early, hold, or diversify. The stakes feel enormous because they are.

Chapter 2

The Complexity

Marcus faces a web of interconnected decisions. Exercising ISOs triggers AMT calculations that cascade through his entire tax picture. His net worth is 90% concentrated in one company. He needs a diversification strategy that accounts for lockup periods, blackout windows, and 10b5-1 plan requirements. Every decision has tax implications that compound over years.

ISO exercise timing and AMT exposureConcentration risk in a single stockIPO lockup strategySecondary market opportunities
Chapter 3

The Tesseract Way

Your Personal CFO builds a multi-year equity strategy: optimal ISO exercise timing based on AMT projections, a systematic diversification plan that respects lockup windows, and a comprehensive financial model that shows the impact of each scenario. You see the numbers, the tradeoffs, the roadmap. Then you decide.

Your Dashboard View

A glimpse of what Marcus's Personal CFO dashboard looks like.

Tesseract Dashboard

Marcus

Total Net Worth

$12,500,000

Equity60%
Cash & Fixed25%
Other15%

Projected Annual Tax Savings

$340,000

Through optimized strategy

Action Items

  • 1Review ISO exercise strategy for Q2
  • 2Update 10b5-1 plan parameters
  • 3Evaluate secondary sale opportunity

Upcoming Deadlines

ISO Exercise Window

Apr 15, 2026

31d

RSU Vest Date

Jun 1, 2026

78d

This Could Be Your View

See your complete financial picture in one place.