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

    Two Americas, Financial Infidelity and SpaceX's $60 Billion Bet — Episode 187

    Corporate America is printing money. Everyday Americans are paying $7 for a gallon of gas. And somehow both things are true at the same time. In Episode 187 of The Liquidity Event, AJ and Shane dig into a Wall Street Journal piece on the growing divide between corporate profits and consumer reality, why the Amex CEO's earnings call comments should give everyone pause, and what a 90% marginal tax rate in the 1950s actually tells us about wealth inequality today. Then they turn to SpaceX's reported bid to acquire Cursor, the AI coding app, for $60 billion, and why Shane thinks it's less about the product and more about owning the distribution channel in the age of AI. Plus a tangent about Word document intake forms at high-end law firms that somehow makes a lot of sense. The episode closes with a deep dive into financial infidelity, secret bank accounts, DraftKings addiction, and why AJ and Shane believe that any kind of scorekeeping in a relationship is a slow road to couples therapy. Spoiler: they ran out of time before getting to RAMP and the grandchildren trust listener question, so stay tuned for next week. Topics covered: The two-track American economy and who is actually benefiting Why the Amex CEO's earnings call comments reveal something uncomfortable SpaceX's $60 billion bid for Cursor and the vertical integration play Software as the new hardware and why distribution is the new moat Financial infidelity, secret accounts and the real cost of money secrets in marriage Joint vs. separate finances and what actually works for couples Timestamps: 00:00 Intro and Shane's Ohtani Dodgers jersey from Japan 01:53 Today's episode preview: corporate profits, SpaceX, divorce and more 03:30 Corporate America is minting money while consumers struggle to buy eggs 04:46 The 90% marginal tax rate and what it tells us about wealth inequality 08:03 SpaceX wants to buy Cursor for $60 billion and what that actually means 11:25 Why distribution is the new moat in the age of AI 15:11 Software fatigue is real and why companies are slow to change 19:40 Financial infidelity: secret bank accounts and the real cost of money secrets 21:37 Joint vs. separate finances and what actually works for couples 25:10 Scorekeeping in relationships and why it's a slow road to divorce 🔔 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

    29 min

  2. APR 23

    Money, Kids and Generational Wealth with Special Guest Charlotte Geletka — Episode 186

    What if the most important financial conversation you ever have isn't with your advisor, it's with your kids? In Episode 186 of The Liquidity Event, AJ is joined by Charlotte Geletka, CFP and author of the children's book "Battery the Bulldog and the Funny Money Tree," for a wide ranging conversation about raising financially literate kids in a world where cash is disappearing and TikTok is handing out investment advice. Charlotte and AJ dig into when to start talking to kids about money, how to raise children who understand the value of hard work without shielding them from reality, and how to course-correct when your 8-year-old starts critiquing the star rating of hotel rooms. They also tackle the harder questions around inheritances, trust funds, and why financial literacy matters just as much at the top of the wealth ladder as it does at the bottom. The episode wraps with a practical breakdown of 529 plans, how grandparents and family members can contribute meaningfully, and a quick-fire round covering the worst money advice parents give, the right age for a first credit card, and whether meme stocks are a teaching tool or a gateway to a gambling problem. Topics covered: When and how to start talking to kids about money Raising financially grounded children in high net worth households Allowances, chores and kid-friendly financial tools like Greenlight Inheritances, trust funds, and spendthrift clauses 529 plans: who they work for, who they don't, and how to superfund them Generational wealth vs. generational knowledge Timestamps: 00:00 Intro and welcome to Charlotte Geletka 01:09 Charlotte's background, her CFP practice and the children's book 03:57 When should you start talking to kids about money? Earlier than you think 07:33 How the words adults use around money shape kids' relationship with it 09:20 How to raise kids who appreciate what they have without becoming spoiled 11:28 Chores, allowances, and giving kids real financial responsibility 16:38 Why kids are learning about money from Zillow and TikTok, whether you like it or not 19:10 Inheritances, trust funds and what happens when big money meets young adults 22:00 529 plans: AJ and Charlotte break down everything you need to know 28:01 Quick fire round: worst parent money advice, first credit cards and meme stocks 🔔 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

  3. APR 16

    Tax Day Confessions, The Upper Middle Class Trap, and the SpaceX IPO — Episode 185

    It's Tax Day, and Shane and Kody are in their element. In Episode 185 of The Liquidity Event, they kick off with a behind-the-scenes look at what tax season actually looks like for financial planners, from correcting misclassified stock options to saving clients tens of thousands of dollars that TurboTax Live told them they owed. They also dig into how Intuit used large language models to compress 900 pages of new tax legislation into weeks of implementation instead of months, and whether a viral Reddit post claiming Claude Code can replace TurboTax entirely is onto something or a cautionary tale. Then it's onto the Wall Street Journal's finding that the upper middle class has tripled since 1979, why income alone doesn't tell the whole story, and what a $2 trillion SpaceX IPO valuation actually means for investors with private stock heading into a potentially wild summer debut. Topics covered: Tax season war stories and common filing mistakes with equity compensation How Intuit used AI to implement 900 pages of new tax legislation in weeks The upper middle class defined: who qualifies and why income alone isn't enough Cost of living, housing affordability, and purchasing power by geography SpaceX IPO outlook, valuation history, and what private shareholders should consider Can Claude Code actually do your taxes? A Reddit experiment reviewed Timestamps: 00:00 Intro and Tax Day with Kody 01:19 What tax season actually looks like for financial planners 03:52 TurboTax Live told my friend he owed $50k more than he did 05:45 Shoutout to AJ on digital detox and today's episode preview 08:31 How Intuit used AI to process 900 pages of new tax law in weeks 13:33 More Americans are breaking into the upper middle class 15:17 Why income alone doesn't define middle class and what's missing from the data 22:58 SpaceX eyes a $2 trillion IPO valuation amid C-suite shakeups 28:29 SpaceX valuation history: from $10B in 2015 to $1.75T today 30:59 Reddit: Claude just did my taxes and I'm shorting Intuit $100k 🔔 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. APR 9

    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

  5. 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

  6. 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

  7. 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

  8. 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
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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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