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

Brooklyn Fi
  • 5.0 (18)
  • INVESTING
  • UPDATED WEEKLY

The Liquidity Event is a show about all things personal finance with a laser focus on equity compensation. Your hosts AJ and Shane will take you through the week's news on #fintech, IPOs, SPACs, founder wins and fails, crypto, and whatever else these two nerds think is interesting. AJ and Shane are the financial advisors behind wealth management and tax firm Brooklyn FI, and have helped hundreds of clients plan for successful exits and financial independence. As proud millennials, they have a deep skepticism of the traditional financial services industry. They'll dish about the tools they use to help their clients and give you a look under the hood of how they run their modern, tech-forward wealth management firm. Whether you've got worthless stock options or work for a company about to go public at a 10-billion dollar valuation, every Monday morning your hosts will demystify the headlines and take you through the money stuff that matters – like a diversified portfolio and getting to financial independence as fast as possible. Warning: There may be swearing and lukewarm takes. Learn more at Brooklynfi.com/podcast and subscribe to hear new episodes Monday mornings.

  1. 6D AGO

    Anthropic vs The Pentagon, Boomers Control the Market, and the AI Era Debate – Ep 178

    Are AI companies about to clash with the U.S. government? On this week's episode of The Liquidity Event, AJ and Shane break down rising tensions between Anthropic and the Pentagon, what it means when an AI company draws ethical lines around military use, and why vendor dependency at scale is becoming a real risk — even for the Department of Defense. They also dig into new data showing Americans over 65 now control nearly 40% of equities, how federal spending tilts toward retirees, and what that means for younger generations trying to build wealth today. The episode wraps with a conversation about the AI boom versus the dot-com era, why public sentiment feels different this time, and what automation could mean for white-collar workers. Plus: estate planning reminders, AI "afterlife" tech, and why IPO liquidity events are never as simple as they look. Key Timestamps 0:34 – AJ Is Back and Episode Preview 2:55 – AJ's Dental Saga 3:24 – Anthropic Tender Offer Reminder 4:12 – Anthropic vs The Pentagon and AI Safety 8:21 – Autonomous Weapons and Ethical Limits 11:48 – Americans Over 65 Now Control the Market 14:33 – Federal Spending and Generational Wealth Shift 22:10 – AI Posting After Death and Digital Legacy 25:32 – Estate Planning Soapbox 27:54 – AI Boom vs Dot Com Era and What Comes Next 🔔 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

    32 min

  2. FEB 19

    SpaceX's $50B IPO, AI Salary Gaps & Trusting ChatGPT With Your Taxes? – Ep 177

    Is SpaceX about to break the IPO playbook? And what happens when AI salaries completely reshape relationship dynamics? On this week's episode of The Liquidity Event, Shane is joined by BKFi Senior Tax Associate Ethan Burroff to break down SpaceX's potential $50 billion IPO and what it means for retail investors, equity holders, and tax planning. They also dig into how massive AI compensation is shifting power dynamics in relationships, why techies are swapping wedding bands for Oura Rings, and what to know before trusting ChatGPT with your tax return. The episode wraps with a Reddit tax cautionary tale and a reminder that AI still isn't your CPA. If you work in tech, hold equity, or are navigating a big financial transition, this one's for you. Timestamps 00:00 – Welcome to Episode 177 00:01:00 – Ethan's Origin Story: From Listener to BKFi Tax Associate 00:04:20 – SpaceX's $50B IPO & Retail Investor Access 00:09:20 – IPO Tax Complications & What Employees Should Expect 00:11:40 – Oura Rings as Wedding Bands? Tech Culture & Biometrics 00:17:55 – AI Salaries & Income Disparities in Relationships 00:24:40 – Why This Winter Has Been So Extreme 00:29:10 – Can You Trust ChatGPT to Do Your Taxes? 00:31:00 – Where AI Still Falls Short in Tax Planning 00:32:30 – Final Thoughts & Listener Call-Out 🔔 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

    33 min
  3. An IRS Agent's Side Hustle, Anthropic's $300B Tender, & Can You Afford a $1.8M Home? – Ep 176

    FEB 12

    An IRS Agent's Side Hustle, Anthropic's $300B Tender, & Can You Afford a $1.8M Home? – Ep 176

    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

    37 min
  4. The Richest Americans Ever, SpaceX's Mega Merger, and Regret Investing Too Conservatively – Episode 175

    FEB 5

    The Richest Americans Ever, SpaceX's Mega Merger, and Regret Investing Too Conservatively – Episode 175

    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. Key Timestamps (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

    36 min
  5. Childcare Costs, Private Equity Ruining Everything, and When to Wake Up – Episode 174

    JAN 29

    Childcare Costs, Private Equity Ruining Everything, and When to Wake Up – Episode 174

    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. Key Timestamps (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

    31 min

  6. JAN 22

    Rebroadcast: Roadie. Atlantic Crossing. RIA Founder: The Shane Mason Story

    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

    39 min
  7. Nuclear Energy, Tax Reform, and the Med Spa Economy – Episode 172

    JAN 15

    Nuclear Energy, Tax Reform, and the Med Spa Economy – Episode 172

    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. Key Timestamps (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

    27 min
  8. New York Data Privacy, K-Shaped Tax Cuts, All-Cash NYC Real Estate, and Annuity Myths – Episode 171

    JAN 8

    New York Data Privacy, K-Shaped Tax Cuts, All-Cash NYC Real Estate, and Annuity Myths – Episode 171

    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. Key Timestamps (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

    33 min
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The Liquidity Event is a show about all things personal finance with a laser focus on equity compensation. Your hosts AJ and Shane will take you through the week's news on #fintech, IPOs, SPACs, founder wins and fails, crypto, and whatever else these two nerds think is interesting. AJ and Shane are the financial advisors behind wealth management and tax firm Brooklyn FI, and have helped hundreds of clients plan for successful exits and financial independence. As proud millennials, they have a deep skepticism of the traditional financial services industry. They'll dish about the tools they use to help their clients and give you a look under the hood of how they run their modern, tech-forward wealth management firm. Whether you've got worthless stock options or work for a company about to go public at a 10-billion dollar valuation, every Monday morning your hosts will demystify the headlines and take you through the money stuff that matters – like a diversified portfolio and getting to financial independence as fast as possible. Warning: There may be swearing and lukewarm takes. Learn more at Brooklynfi.com/podcast and subscribe to hear new episodes Monday mornings.

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