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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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

📱 Follow Brooklyn FI:

LinkedIn: / brooklyn-fi

Instagram: / brooklyn_f.i

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

📱 Follow Brooklyn FI:

LinkedIn: / brooklyn-fi

Instagram: / brooklyn_f.i

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

📱 Follow Brooklyn FI:

LinkedIn: / brooklyn-fi

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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

In this post–Election Week episode of The Liquidity Event, AJ and Shane dive into New York City's new mayor, former rapper Zohran Mamdani, and what his win could mean for taxes, wages, and city life. AJ shares her marathon weekend adventures and Halloween highlights, while Shane talks about biking through Manhattan gridlock, watching Tame Impala, and catching the World Series.

They unpack NASCAR champ Kyle Busch's $8.5 million insurance lawsuit, OpenAI's new public benefit status, and the latest push for a global wealth tax. The conversation covers billionaire carveouts, the "Teach for America for failed politicians" idea, and closes with thoughts on fairness, community, and the economics of a changing New York.

Timestamps: (00:00) Welcome to The Liquidity Event, marathon weekends, and mime makeup (04:30) Zoran Mammadani wins NYC, a new era (and some saber-rattling) (06:00) AJ's "Teach for America, but for failed politicians" proposal (07:30) Shane's Tame Impala flex, Game 7 chaos, and fall weekend vibes (09:30) NASCAR's Kyle Busch sues Pacific Life, insurance gone wild (14:00) OpenAI's $500B milestone and the rise of "too big to fail" tech (20:00) The great wealth tax debate, guillotines, Birkins, and billionaire tears (27:00) Universal healthcare dreams and the Brooklyn FI insurance saga (32:00) Mamdani's 2% millionaire tax, free buses, and grocery-store wars (39:00) Closing thoughts, fairness, optimism, and five-star requests

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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 Halloween-week episode of The Liquidity Event, AJ and Shane gamble their way through Atlantic City stories, poker scandals, and billionaire luck. AJ checks in from self-imposed exile at the Jersey Shore to finish her book (and avoid the casinos), while Shane shares his thoughts on gambling's strange evolution from high stakes to digital dopamine.

The duo dives into Governor JB Pritzker's million-dollar Vegas win, a sprawling FBI gambling case that reads like Ocean's Eleven, and the Louvre jewel heist that has everyone rooting for "Flappy." They debate whether Bitcoin counts as investing or just fancy gambling, share their favorite open enrollment hacks, and field a listener question about when it's okay to stop sweating the $6 latte.

They wrap up with a surprisingly heartfelt segment on digital estate planning—passwords, personal finance apps, and the love letter your will should be.

Timestamps: (00:00) Welcome to The Liquidity Event — AJ live from Atlantic City (02:00) Halloween plans, weddings, and the curse of the off-season boardwalk (04:30) AJ and Shane head to San Diego for the Personal Financial Planning Summit (06:00) Gambling talk — JB Pritzker's million-dollar win (09:00) FBI's "Operation Royal Flush" and NBA gambling scandals (13:00) Ocean's Eleven in real life — marked cards and the legend of "Flappy" (15:30) The Louvre jewel heist and Shane's power tools (17:00) AI gone too far — Sora, deepfakes, and existential dread (18:00) JP Morgan's Bitcoin collateral move — investing or gambling? (20:00) Open enrollment season tips and why life insurance still matters (23:30) FSAStore.com, sponsorship dreams, and practical tax hacks (24:00) Listener question: when did you stop caring about small purchases? (27:00) Behavioral finance, Faulkner envy, and the psychology of frugality (28:00) Digital estate planning and your "password love letter" (33:00) Personal Capital, Mint, and the problem with dying apps (34:00) Closing thoughts — lattes, legacies, and leaving clean spreadsheets

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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, Shane and guest host Ed Z cover everything from Nobel laureates disappearing into the woods to Italy's flat-tax paradise for the ultra-rich. They unpack why more working-class Americans are turning to the stock market, debate whether democratized investing is empowerment or gambling, and answer a listener question about why companies are staying private longer. The duo also tackles Reddit's $750,000 cash conundrum, the truth about life insurance "wealth hacks," and end on chess, broken office chairs, and the art of tax-season survival.

Timestamps: (00:00) Shane's office chair falls apart — chaos at tax day HQ. (02:00) Meet guest host Ed Z (04:15) Disney planning with AI — Shane and Ed test ChatGPT's travel agent skills (06:30) The government shutdown, Epstein theories, and suit shopping with AI (07:25) Nobel laureate goes missing — why geniuses love the woods (09:30) Italy's "La Dolce Vita" flat-tax scheme for the ultra-rich (13:00) Corruption, $1 Italian homes, and Shane's mafia jokes (15:00) The working class joins Wall Street — Robinhood, risk, and returns (19:00) Why democratizing investing is both thrilling and terrifying (20:00) Listener question: why aren't companies going public anymore? (24:00) Private money, long horizons, and the rise of private equity ETFs (26:30) Reddit question: what to do with $750,000 in cash (29:00) Life insurance "wealth hacks" and why caps on returns are a scam (31:30) Chess, Fabiano Caruana, and why Shane's the only spectator in St. Louis

🔔 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