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

Brooklyn Fi
  • 5.0 (18)
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  • 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. 4D AGO

    Episode 184: Expat Retirement Planning, Dual Citizenship Taxes, and the Babylist IPO

    Can you keep your 401k when you move abroad? What happens to your Roth IRA if you live in France? And is a baby registry company really worth watching as an IPO? In Episode 184 of The Liquidity Event, Shane and AJ tackle one of the most common questions they get from American expats and dual citizens: how do you build a retirement plan when you're living abroad, paying taxes in another country, and still filing as a US person? Shane breaks down how income tax treaties work, what expats need to know about 401k and Roth IRA distributions overseas, the real cost of moving money between countries, and why accidental Americans can face some surprising IRS consequences. Then they dig into Babylist, the baby registry platform approaching $1 billion in sales and eyeing a 2027 IPO. It's been profitable for eight straight years, raised only $40 million in outside capital, and sat out the 2021 IPO rush entirely. AJ and Shane break down why the asset-light model works, what it has in common with Etsy, and why babies aren't going anywhere. Topics covered: Expat retirement planning and 401k rules for Americans living abroad Dual citizenship tax strategy and income tax treaties Roth IRA distributions for US citizens overseas Currency hedging and moving money internationally Babylist IPO outlook and what makes it different Financial planning for Americans with dual citizenship in Europe Timestamps: 00:00 Intro and AJ's desk flooding incident 01:55 Iran ceasefire reaction and NYC nuclear anxiety 07:45 The Brooklyn of New Delhi and global culture 12:20 Listener question: retirement planning as an American abroad 13:58 How income tax treaties protect expat 401k holders 18:24 Moving money internationally and currency hedging 21:17 Why financial planning abroad is uniquely complex 24:28 Babylist approaches $1B in sales and eyes 2027 IPO 🔔 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

  2. APR 2

    Q1 Market Whiplash, Millionaire Tax Strategies and Bitcoin Backed Mortgages - Episode 183

    Q1 started strong and then the final stretch changed everything. In Episode 183 of The Liquidity Event, AJ and John break down what actually happened in the markets this quarter, from oil's sharp rise and renewed inflation concerns to why both stocks and bonds felt pressure. They walk through how global conflict impacts commodities, rate cut expectations, and what investors should really be paying attention to as we move into Q2. The conversation also covers the growing world of advanced tax strategies for high net worth investors, including direct indexing, 351 exchanges, and exchange funds. These tools are becoming more accessible, but they are not one size fits all. AJ and John explain how they work, who they are actually for, and why complexity does not always mean better outcomes. They also unpack a headline making the rounds about a major league baseball player suing his parents over alleged financial mismanagement, and what it reveals about family dynamics and sudden wealth. Finally, they explore the new Bitcoin backed mortgage structure entering the market and whether it is financial innovation or leverage risk in disguise. Key Timestamps 2:05 – Q1 Market Recap and the Oil Spike 4:10 – Inflation Concerns and Shifting Rate Cut Expectations 6:30 – How Gas Prices Hit Everyday Investors 9:00 – MLB Player Sues Parents Over Millions 12:15 – NIL Deals and Young Athletes Managing Wealth 16:05 – The One Trillion Dollar Industry of Tax Reduction 18:40 – Direct Indexing and When It Makes Sense 21:30 – 351 Exchanges and Exchange Funds Explained 25:10 – Tax Aware Long Short Strategies and the Risks 29:45 – Bitcoin Backed Mortgages and Leverage Concerns 🔔 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

  3. MAR 26

    BuzzFeed's AI Collapse, Coinbase vs. Big Banks, and the SpaceX IPO Is Official - Episode 182

    In Episode 182 of The Liquidity Event, Shane and Kody break down a week of major financial headlines that highlight just how fast markets and technology are shifting. They discuss BuzzFeed's dramatic fall after its aggressive AI pivot, why Coinbase's push into stablecoin yields has traditional banks on edge, and what SpaceX's potential record-breaking IPO could mean for employees and investors alike. They also answer a listener question on how to invest $10,000 per month over a 20-year horizon without trying to time the market. If you work in tech, hold equity, or are building long-term wealth, this episode is for you. Key Time Stamps: 0:00 – Intro and hockey injuries 3:10 – BuzzFeed's AI pivot and stock collapse 6:45 – Why employees need a trading plan 9:30 – Coinbase vs. traditional banks at Davos 12:15 – Stablecoins and 3.5% yield controversy 15:40 – Is crypto still mostly speculation? 18:20 – SpaceX IPO targeting June 21:05 – Lockups, insider selling, and IPO risk 24:10 – What to do if you hold SpaceX shares 27:45 – How to invest $10K per month long term 🔔 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

  4. MAR 19

    Mega IPOs, AI at Work and Why Everyone's Exhausted - Episode 181

    AI is everywhere right now. In IPO markets, in SaaS business models and in your day to day workflow. On this week's episode of The Liquidity Event, Shane and AJ break down why mega IPOs like OpenAI and SpaceX are creating a gravity well in the public markets, what that means for smaller companies waiting to go public and whether the IPO pipeline is actually reopening in 2026. They also dig into the growing tension inside software companies as AI agents begin to threaten seat based pricing models and what recent disclosures are quietly admitting about the competitive risks. Finally, they unpack new research showing that AI may not be lightening workloads at all. Instead, it may be increasing email volume, decision fatigue and what researchers are calling AI brain fry. Is AI making us more productive or just more overwhelmed? Key Timestamps 01:45 – Vibe coding, Claude inside PowerPoint and AI workflow shifts 06:10 – Is the IPO winter actually over? 08:25 – The gravity well effect of mega IPOs like OpenAI and SpaceX 11:40 – Why smaller IPOs are stuck in the pipeline 14:05 – SaaS companies quietly disclosing AI as a material risk 17:20 – Will AI agents break the seat based pricing model? 21:10 – AI is not reducing workload, it is increasing intensity 24:35 – Email volume, messaging overload and deep work decline 27:50 – AI brain fry and the rising intent to quit 31:15 – Mastery, autonomy and purpose in an AI driven workplace 🔔 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

    35 min

  5. MAR 12

    AI Replacing Advisors, 401(k) Hardship Withdrawals, & 24/7 Tokenized Stocks – Ep 180

    On this week's episode of The Liquidity Event, AJ and Shane unpack what's happening at the intersection of AI, financial advice, and investor behavior. Shane joins from the T3 technology conference in New Orleans, where artificial intelligence dominated nearly every conversation. They explore how AI tools are being integrated into advisory firms, whether real-time financial planning during client meetings is closer than we think, and react to a bold claim from a venture-backed RIA that advisors may eventually be replaced by AI. The conversation then shifts to a Wall Street Journal report on rising 401(k) hardship withdrawals. AJ and Shane discuss what the data actually shows, how automatic enrollment has changed participation rates, and whether easier access to retirement funds is a positive development or a long-term risk. They also break down Kraken's proposal to tokenize publicly traded stocks and enable 24/7 trading, debating whether constant market access improves liquidity or amplifies behavioral mistakes. The episode wraps with a listener-inspired question on protecting net worth from lawsuits and market losses, including what umbrella insurance can realistically accomplish and where its limits lie. As always, the discussion blends industry insight with practical takeaways for navigating an increasingly complex financial landscape. Key Timestamps: 01:08 – Shane reports live from the T3 technology conference 03:12 – AI University and what advisors are actually building 06:40 – The future of real-time financial planning with AI 10:18 – Range says AI will replace advisors… should we believe it? 14:02 – Why humans are still the "hardware" in financial advice 17:36 – Record 401(k) hardship withdrawals and what's really happening 20:44 – Are hardship withdrawals actually good for 401(k) adoption? 23:18 – Kraken wants to tokenize stocks and trade 24/7 26:05 – Is 24/7 stock trading a feature or a bug? 28:42 – Reddit: How do you protect your net worth from lawsuits? 🔔 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

  6. MAR 5

    AI Doomsday Scenarios, Power Plants in Small Towns, & The $10M Advisor Fee Debate – Ep 179

    On this week's episode of The Liquidity Event, Shane and AJ break down the viral "Settrini Report," a fictional yet plausible AI scenario that rattled markets and raised serious questions about productivity, white-collar job displacement, and the future of labor's share of GDP. They discuss whether AI pricing is sustainable, what new data center infrastructure means for small-town America, and why we may be closer than ever to a zero-employee unicorn company. The conversation then shifts to the ethics and economics of organ donor compensation, including whether families should be reimbursed for funeral expenses and how incentives shape real-world outcomes. The episode wraps with a Reddit debate about paying 1.25% on a $10 million portfolio, what that fee should actually buy you, and why behavioral discipline often matters more than cost. Key Timestamps: 01:52 – How the "Settrini Report" went viral and moved markets 04:18 – AI agents replacing $180K product managers 07:02 – What happens if labor's share of GDP collapses 09:40 – Is AI pricing real, or just VC-subsidized for now? 12:11 – AI infrastructure, power plants, and small-town impact 15:03 – The rise of the zero-employee unicorn founder 18:27 – Organ donor compensation and the ethics debate 22:10 – How other countries structure organ donor incentives 24:54 – Paying 1.25% on a $10M portfolio… is it worth it? 28:41 – Market volatility, geopolitical tension, and staying disciplined 🔔 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

  7. FEB 26

    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

  8. 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
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About

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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