Webinar with Highland Private Wealth and Jacobson Lawrence
ensembleadvisorOur guest speakers are James Norbeck, CPA from Jacobson Lawrence and Michael Greene, CFP from Highland Private Wealth.
Live discussion about how highly compensated employees with stock options, RSU's, ISO's, NSO's, NUA and awards can plan and mitigate their tax consequences.
Highlights:
- Tax Risk (Bigger than Market Risk)
- AMT owed even if stock later falls
- Large tax bills without liquidity - "I exercised, paid tax, and then stock dropped"
- Modeling AMT across multiple tax years
- AMT can be owed even if shares aren't sold
- AMT triggers and credit recovery
- Liquidity planning - “I made money on paper but owe tax in cash.”
- Concentration Risk - "My job, bonus, portfolio all depend on one stock"
- Expiration risk
- Strategies for liquidation - Short Term Rentals, Option Protection, Exchange Funds, Leveraged Long/Short
- Capital gains vs Ordinary Income tradeoff (NIIT)
- High income ≠ high liquidity - “I’m a high earner but feel cash-constrained.”
- Blackout windows and insider trading rules - 10b5-1 requirements - “I want to diversify, but I’m legally blocked.”
- Leaving before major vesting events - “Should I stay for vesting—or leave for a better role?”
- How to integrate into your overall Financial Plan (College financial aid implications, Medicare IRMAA, Charitable Strategies, Estate Planning)
- We will also have time for a live Q and A.
