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

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

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In this episode of The Liquidity Event, AJ and Shane dig into the trillion-dollar AI ecosystem, from NVIDIA's massive market cap to the circular funding loops tying together OpenAI, Microsoft, and the rest of the AI stack. They debate whether today's infrastructure buildout is necessary progress or a replay of past bubbles, and what happens if one key player breaks the chain.

The conversation then shifts to SpaceX's active tender offer, what employees need to know right now, and why timing across tax years can be life-changing for equity holders. Along the way, AJ and Shane explore high-tax residency decisions, year-end planning pressures, and the real-world implications of building massive data centers, including job creation, community development, and energy costs. The episode wraps with behind-the-scenes updates on Gemini, market optimism for 2026, and a refreshingly silly mid-December detour or two.

(00:00) Welcome, holiday vibes, and guest appearance from Charlie Mason
(03:00) California pride, taxes, and why people still stay
(05:00) How AJ and Shane pick articles (and why tangents win)
(08:30) Philly cheesesteaks, grills, and peak mid-December chaos
(10:30) NVIDIA, OpenAI, and the trillion-dollar AI money loop
(13:30) Circular deals, AI bubbles, and "being right no matter what"
(16:30) Infrastructure scale: AI vs. telecom vs. AWS
(19:30) Data centers, job displacement, and AI's real costs
(22:00) SpaceX tender offers, liquidity timing, and tax strategy
(29:00) Gemini updates, 2026 optimism, and wrapping the silliness

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

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

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In this episode of The Liquidity Event, AJ and Shane dive into billionaire wealth gaps, UK "rags to riches" stories, and what happens when fast financial success reshapes friendships. They unpack media narratives, economic inequality, and why Business Insider profiles might not tell the full truth. The conversation expands into EU vs. US tech power, streaming-platform consolidation, and the rise of "enshittification" across the internet.

AJ and Shane also cover year-end money moves, including FSA/HSA spending strategies, Trump Accounts, and how early-life investment programs could change generational wealth. They discuss credit-building hacks, life-changing compounding math, and the personal finance implications of giving every American baby a federally funded investment account. The episode closes with a look at what to do with an extra $100K at year-end — plus a few fun ideas for how to blow it in six hours.

Key Timestamps

(00:00) Bemelmans Bar recap and the Shrimp Cocktail Index
(03:00) Rags-to-riches story: £20M in 8 years and the fallout of fast success
(05:00) "Self-made" narratives, Bill Gates' daughter, and privilege vs. perception
(08:10) UK vs. US GDP, economic decline, and foreign ownership concerns
(09:30) Big Tech fines in the EU and the power imbalance with U.S. platforms
(11:45) Streaming chaos: Netflix, Warner Bros., pirating, and lost media access
(12:50) "Enshittification" explained — how platforms get worse over time
(13:20) FSA/HSA hacks, eligible gift ideas, and Peloton letters of medical necessity
(16:30) Trump Accounts, Dell family matching, and life-changing compounding math
(26:00) What to do with an extra $100K — loans, DAFs, mortgages, and dream spending

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🌐 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

In this episode of The Liquidity Event, AJ and Shane regroup after a failed recording attempt and dive straight into Thanksgiving chaos, rising ACA premiums, and the political fight over healthcare subsidies. Shane shares his 35% insurance shock while AJ breaks down what subsidy cuts mean for millions of Americans. They also explore the push to privatize federal student loans, Google's plan to run AI models in space, and why real estate inheritances are a wealth-management minefield. The episode wraps with estate-planning talk, holiday-table conversations no one wants to have, and a reminder that the U.S. tax and policy machine rarely chooses the simplest path.

Key Timestamps:

(00:00) Recording chaos, travel mishaps, and Thanksgiving greetings
(02:01) Epstein's accountant and the episode's finance lineup
(03:05) Holiday plans: Mexico City, Palm Springs, and stove-top traditions
(04:27) Notion, favorites tracking, and the Clueless digital closet dream
(08:51) What AJ and Shane are grateful for this year
(14:22) ACA subsidy expiration and national healthcare fallout
(14:59) Shane's 35% health-insurance surge and enrollment nightmare
(19:41) Student loan privatization and servicer failures
(26:15) Google's Project SunCatcher and AI computing in space
(29:48) $5M inheritance question and real-estate-heavy estate planning

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

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

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In this episode of The Liquidity Event, AJ and Shane recap Brooklyn FI's estate planning party at Clover Club, complete with notaries, crystal balls, and millennials confronting wills, pets, and chosen family. They also cover the latest economic confusion including layoffs, tariffs, AI fears, the Shrimp Cocktail Index, and California's proposed billionaire tax.

Shane breaks down Scaramucci's tariff refund theory while AJ reflects on trust in data, government transparency, and who actually pays for society. The episode closes with questions about corruption, sustainability, and whether two money nerds with a TI 83 could solve the tax code.

Key Timestamps:

(00:00) AJ's stiff neck and chaotic start
(02:39) Estate planning party at Clover Club
(04:31) Shane's three-year estate plan procrastination
(05:36) Wills, chosen family, and pet guardians
(08:09) The lost Tacos and Taxes era
(09:26) WARN spikes, layoffs, and missing data
(14:32) Scaramucci and the tariff refund theory
(16:48) The Shrimp Cocktail Index returns
(21:13) California's one-time five percent billionaire tax
(30:13) Why neutrality is impossible when policy affects clients

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

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

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In this episode of The Liquidity Event, AJ and Shane cover everything from shattered mirrors to shattered housing markets. AJ shares an update on her book deadline and upcoming Thanksgiving travel while Shane recounts a chaotic morning involving a Roomba and a broken mirror. The duo unpack the hidden tax pitfalls of S-Corps in New York City, debate credit card rewards and travel perks, and react to the Frontier Airlines CEO telling customers to buy a backup ticket. They also dive into the strange slowdown in new home sales, the Trump administration's proposed 50-year mortgage, Elon Musk's massive pay package, and whether the AI boom is already bubbling over.

(00:00) Welcome, introductions, and AJ's end-of-year check-in
(01:00) Shane's Roomba disaster and chaotic morning
(02:30) AJ's book update and Thanksgiving travel plans
(04:00) Delta, Marriott, and Chase credit card strategy for the holidays
(08:45) Why S-Corps don't make sense in New York City
(12:20) Frontier Airlines CEO tells customers to buy a backup ticket
(15:15) AJ on the government shutdown and SNAP benefits
(18:15) Housing market troubles and unsold new builds
(23:10) The Trump administration's 50-year mortgage proposal
(29:45) AI, crypto, and whether the boom is just another bubble

🔔 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