Today we're sharing a special rebroadcast of John Owens's appearance on The Long Term Investor with Peter Lazaroff. In this episode, John breaks down a clear, practical year-end playbook for equity compensation, including RSUs, ISOs/NQSOs, and ESPPs, and highlights the tax traps and planning opportunities clients should keep on their radar.
You'll hear John and Peter discuss:
- How to prioritize equity comp decisions at year-end
- Common RSU withholding pitfalls that lead to April surprises
- ISO/AMT basics and why late-year exercises can be risky
- Building a rules-based selling strategy to manage concentration
- When donor-advised funds and multi-year planning make sense
This episode originally aired on The Long Term Investor and is shared here with permission. To explore more of Peter's work, visit The Long Term Investor.
Key Timestamps:
- (00:00) Introduction
- (03:15) A hard-won lesson: when AMT grows larger than your stock (and what to do next)
- (04:21) Don't start equity planning on December 15 (really) (05:19) First move: build an inventory and triage the quick wins
- (08:18) AMT 101 for ISO holders: the "parallel" tax you don't want to pay
- (10:47) RSUs: why 22% withholding often sets up an April tax bill
- (12:24) ESPPs: capture the discount, control concentration (14:55) Designing a rules-based sell plan to unwind concentration risk
- (18:11) The base rates on single stocks: why a diversification plan matters more than a "feel" (20:42) 10b5-1 plans: automate good behavior and expand your ability to sell
- (23:31) Charitable giving with concentrated stock: donor-advised funds and timing across 2025/2026
- (26:11) Family gifting: UTMAs, kiddie tax, step-up in basis, and multi-generational choice
- (27:28) The year-end document checklist most people miss
- (29:17) When to hire help (and when not to) (31:19) Biggest year-end mistakes to avoid
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