Year-End Equity Comp Playbook With John Owens (EP.230)

Your finances have layers—investments, taxes, planning for the future. If you want a second set of eyes, Peter opened up a few spots for a quick, no-obligation call. Grab yours now.

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Equity compensation can turbocharge wealth—and taxes. Brooklyn Fi managing partner John Owens joins Peter to share a clear year-end playbook for RSUs, ISOs/NQSOs, and ESPPs, including how to avoid AMT surprises, right-size withholding, and unwind concentrated stock positions. 

Listen now and learn:

► A simple order of operations for year-end equity comp decisions

► RSU withholding pitfalls (and how to fix them before April) 

► ISO/AMT basics and why late-year exercises can backfire

► How to build a rules-based plan, use 10b5-1 mechanics, and when donor-advised funds make sense

 

Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.

 

(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

Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠)

 

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