The Liquidity Event | Money and Finance with Shane and Ally Jane

In Episode 176 of The Liquidity Event, Shane is joined by Brooklyn Fi Senior Financial Planner Kody Sherlund to unpack a mix of personal finance headlines and real-world planning questions.

They kick things off with an IRS agent who moonlights as an NFL referee and what that says about modern "two-job" America. Then they break down what happens when a 529 plan is overfunded, whether insider stock purchases are actually a bullish signal, and why diversification still matters even when markets feel unpredictable.

The episode also covers Anthropic's reported $300B valuation and employee tender offer, including what to consider before selling private company shares. Finally, they tackle a Reddit question: can a couple earning $750K–$850K afford a $1.8M home in the NYC suburbs?

Key Time Stamps:

00:00 – Welcome + Episode Overview 00:34 – Shane & Kody intro 06:19 – IRS agent who's also an NFL referee 09:45 – What happens when you overfund a 529 plan 15:16 – Rethinking standard investment advice? 20:12 – Can you "beat" the market long term? 21:25 – Do insider stock purchases actually signal upside? 26:40 – Anthropic's $300B valuation & employee tender offer 27:47 – What to consider before selling private shares 32:22 – Can you afford a $1.8M home on $750K income?

🔔 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 episode of The Liquidity Event, Shane is joined by John Owens to dig into wealth, concentration, and how quickly the winners in American capitalism can change. They start with a look at the richest Americans in history, adjusted for inflation, and why names like Rockefeller and Carnegie still matter when thinking about today's tech billionaires. The conversation explores why extreme wealth is often built through concentration, why staying on top is so hard, and what the constantly shifting list of the largest U.S. companies tells us about diversification and long-term investing.

From there, they unpack Elon Musk's blockbuster move to merge SpaceX with xAI, creating the largest merger in history and setting the stage for what could be the biggest IPO ever. They discuss orbital data centers, AI infrastructure in space, and whether rolling multiple companies together is about innovation, valuation, or investor cleanup. The episode wraps with a thoughtful Reddit question from a listener regretting not investing aggressively enough earlier in life, and why hindsight bias, career twists, and steady saving matter more than chasing a perfect past.

(00:00) Welcome to Episode 175 and what's on deck (01:20) The richest Americans in history, adjusted for inflation (06:40) Rockefeller, Carnegie, and why power isn't the same as wealth (08:20) Why the biggest companies change and diversification still matters (10:24) Trivia: the only top-10 company still standing after 20 years (13:00) SpaceX acquires xAI in the largest merger ever (14:30) Orbital data centers, AI compute, and space infrastructure (17:00) Rolling companies together, IPO strategy, and investor outcomes (22:00) Maltbook and what happens when AI agents talk to each other (27:15) FIRE Reddit: regret, risk tolerance, and investing too conservatively (32:25) Why this listener is doing better than they think (35:05) Final thoughts and wrap-up

🔔 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 episode of The Liquidity Event, AJ is joined by Caitlin, Brooklyn Fi's Director of Financial Planning, to unpack why the math of modern life feels so broken. They start with the true cost of having a stay-at-home parent, breaking down why headlines claiming it only takes $90,000 a year fall apart once you factor in taxes, housing, childcare backups, and real-world spending.

From there, the conversation turns to how private equity is quietly reshaping essential services — from volunteer fire departments and hospitals to fertility clinics and Toys "R" Us — and why consolidation often leads to higher costs and worse outcomes. The episode wraps with a lighter discussion on sleep chronotypes and early mornings, listener questions on Botox tipping etiquette, inheritance planning and startup risk, and why holding more cash (in a high-yield savings account) can actually make investors feel more confident in uncertain markets.

(00:00) Welcome to Episode 174 and what's on deck (01:15) Introducing Caitlin and her role at Brooklyn Fi (03:09) How much it really costs to have a stay-at-home parent (04:18) The K-shaped economy and why middle-class math doesn't work (06:41) Private equity and volunteer fire departments (08:15) Consolidation, monopolies, and rising fire truck costs (10:32) Toys "R" Us, hospitals, and private equity fallout (12:04) Fertility clinics, healthcare consolidation, and service breakdowns (14:34) Sleep chronotypes, early risers, and waking up at 5 a.m. (19:18) Botox tipping etiquette and the med spa economy (22:46) Inheritance planning, startup risk, and how much is okay to invest (26:04) Market fear, cash cushions, and why high-yield savings matter

🔔 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

Note: This episode is a rebroadcast of Shane Mason's appearance on the Only Fee-Only podcast.

This week on The Liquidity Event, we're sharing a rebroadcast of a recent conversation featuring Shane Mason on the Only Fee-Only podcast.

In this episode, Shane shares his unconventional founder story, from Big Four tax to touring life, before teaming up with AJ to build Brooklyn FI into a 20-person advisory firm rooted in transparency, productized service, and genuine hospitality. He walks through the early days of the firm, including running a tax practice out of a bar booth, pricing low to gain experience, and taking weekend prospect meetings to refine the offer.

The conversation quickly turns practical, covering why most equity compensation issues are really tax issues, how offering refunds can protect long-term trust, and why turning estate planning into a social, notarized event helps clients finally take action. Shane also discusses building an enterprise rather than a lifestyle practice, documenting workflows for consistency, evolving the firm's niche from creatives to tech employees, and what changes when founders step back from day-to-day client work. The episode wraps with a look at Gemifi, the fintech platform Brooklyn FI built to help advisors visualize vesting schedules and future balance sheets.

If you're building or scaling an RIA, this rebroadcast is full of hard-won insights on processes, client experience, and leading through growth.

Key Timestamps:

• (00:00) Meet Shane Mason and Brooklyn Fi
• (01:38) Career Origins and Early Accounting
• (05:00) Quarter-Life Crisis and Adventures Abroad
• (08:20) Sailing The Atlantic and Roadie Tales
• (11:30) Building A Tax Practice In A Bar Booth
• (14:55) Meeting AJ and Forming The Partnership
• (19:10) Finding XYPN and Learning The RIA Game
• (22:50) First Hires and Evolving The Niche
• (27:00) Estate Planning Parties and Execution
• (34:50) Advice For New Firms And Equity Comp
• (38:50) Taking L's, Refunds, and Reputation

🔔 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 episode of The Liquidity Event, AJ and Shane cover a wide-ranging mix of energy policy, tax reform, tech culture, and the strange economics of looking younger.

They dig into nuclear energy's comeback in the U.S. and why AI, data centers, and crypto are driving a massive surge in energy demand, leaving America far behind countries like China and France. The conversation then shifts to Mitt Romney's New York Times op-ed arguing that the wealthy should pay more in taxes, unpacking the Social Security trust fund cliff, student loans, and the tax "caverns" that delay revenue collection. The episode wraps with a tour of the strangest CES tech, from AI companions to silent ice makers, and a candid look at med spas, Botox as a subscription business, and why injectables have quietly become one of the fastest-growing corners of the economy.

(00:00) Welcome to Episode 172 and what's on deck (02:00) Nuclear energy, tax policy, and this week's agenda (06:15) Why nuclear power is back and what's driving demand (09:30) Nuclear meltdowns, Chernobyl, and reactor risk (12:20) Mitt Romney's "Tax Me" op-ed and the Social Security cliff (14:55) Step-up in basis, payroll tax caps, and tax loopholes (17:30) CES highlights: AI companions and weird consumer tech (19:30) Tech, isolation, and replacing human interaction (22:40) Med spa crackdowns and Botox economics (26:20) Final thoughts and wrap-up

🔔 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 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

🔔 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 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

🔔 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

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

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

🔔 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 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

🔔 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