In this episode of The Liquidity Event, AJ and Shane kick off the new year with a wide-ranging conversation that spans data privacy, tax policy, real estate, and retirement planning, with a few dragon-filled detours along the way.

They start with California's push to rein in data brokers, breaking down how personal data is bought and sold, why spam calls are nearly impossible to stop, and whether privacy legislation can realistically make a difference. The conversation then shifts to the winners and losers of the 2026 tax and benefit changes, unpacking the idea of a K-shaped economy and why tax cuts tend to benefit asset owners far more than workers.

AJ and Shane also dig into Manhattan's all-cash real estate boom, why wealthy buyers did not flee New York despite repeated tax threats, and how liquidity, SBLOCs, and market gains are reshaping who wins bidding wars. The episode wraps with a candid discussion on annuities, why they are often misunderstood, when they can make sense, and how bad actors have given them a deservedly complicated reputation, before teasing a future deep dive into nuclear energy.

Taxes, policy, privacy, and practical planning to start 2026.

(00:00) Welcome to Episode 171, New Year energy, and dragons
(02:00) New Year's Eve stories and West Coast midnight celebrations
(05:15) Romantasy books, dragons, and travel tangents
(07:00) This week's lineup: data privacy, taxes, real estate, annuities, and nuclear energy
(08:20) California data brokers, spam calls, and personal data for sale
(12:00) Winners and losers of 2026 tax and benefit cuts
(14:45) The K-shaped economy explained
(20:00) All-cash Manhattan real estate deals and why the wealthy stayed put
(24:40) SBLOCs, liquidity, and beating traditional buyers
(25:45) Annuities explained, when they work and why they are so controversial

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In this episode of The Liquidity Event, AJ and Shane kick off the new year by breaking down why leaving New York to avoid taxes is far harder than many high earners expect. Using a recent New York Times article as a starting point, they explain how New York residency audits actually work, the difference between quantitative and qualitative tests, and why most people who try to leave the state ultimately fail.

They then shift to OpenAI's decision to finally allow employees to donate equity to charity, why the move matters in the ongoing AI talent war, and how equity structure and tax timing play into charitable planning. The episode wraps with a deep dive into IPO scams, explaining how regulatory carveouts meant to encourage public listings instead enabled a wave of fraudulent foreign companies — and why retail investors are often the ones left holding the bag.

Taxes, equity, audits, and a classic Reddit money question to close out the year.

(00:00) Welcome, New Year timing, and recording Episode 170 in December
(02:00) New Year's plans, hosting fatigue, and seafood traditions
(04:00) The grill disaster and calling an audible on a holiday party
(06:50) Rich New Yorkers threatening to leave and why it's harder than it sounds
(08:15) New York residency audits and the two tests you must pass
(10:10) Qualitative residency rules: holidays, dogs, storage units, and intent
(13:30) Why most people fail New York tax exit strategies
(19:50) OpenAI allows employees to donate equity to charity
(22:30) IPO scams, the JOBS Act, and why fake companies keep slipping through
(26:45) Reddit question: what to do with $1.8M in liquid assets at a young age

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✍️ Leave us a voicemail question for a future episode: memo.fm/theliquidityevent

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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

🔔 Subscribe to The Liquidity Event on YouTube: YouTube Channel

🌐 Learn more about Brooklyn FI financial planning: brooklynfi.com

✍️ Leave us a voicemail question for a future episode: memo.fm/theliquidityevent

📱 Follow Brooklyn FI:

LinkedIn: / brooklyn-fi

Instagram: / brooklyn_f.i