Episodes

  • Semi-Annual Reporting, Rent on Your Credit Score and ChatGPT's Portfolio Fail — Episode 189

    Semi-Annual Reporting, Rent on Your Credit Score and ChatGPT's Portfolio Fail — Episode 189
    May 14 2026
    AJ and Shane are back and gearing up for two weeks of back-to-back travel, a BKFi team retreat in New York and the launch of Gemifi at FPA NorCal in San Francisco. They kick off with the SEC proposal to move public companies from quarterly to semi-annual reporting and why the real story is what fewer reporting periods mean for employees with equity compensation and their trading windows. Then they dig into the government proposal to allow rent payments to count towards your credit score, who it actually helps, who it might hurt, and why the anticipated Anthropic IPO could do to San Francisco housing prices what the Meta IPO did in 2012. They close with a Wall Street Journal experiment where a reporter asked ChatGPT to build and manage a stock portfolio, and a Reddit question about whether it makes sense to have accounts at multiple brokerages. The AI got some things right, made some math errors, and completely missed the point of what a financial advisor actually does. Topics covered: SEC proposal to move public companies to semi-annual reportingWhat fewer trading windows mean for employees with equity compensation and 10b5-1 plans Gemifi launching at FPA NorCal and what the platform doesRent payments counting towards credit scores and who it actually helpsThe Anthropic IPO and its potential impact on San Francisco housing ChatGPT as a portfolio manager: what it got right and where it fell short Multiple brokerages vs. consolidating: what the AI wealth management plugin said Timestamps: 01:13 Team retreat in New York and Gemifi launching in San Francisco 02:10 Palm Springs blue zone campaign and the pickleball scene 06:12 SEC proposal to move public companies to semi-annual reporting 08:08 What fewer trading windows mean for employees with equity compensation 11:25 Gemifi's 10b5-1 plan builder and what the platform does 16:37 AJ's NAPFA keynote recap and the same steakhouse three nights in a row 17:16 Rent payments counting towards credit scores and who it actually helps 21:31 Anthropic IPO and what it could mean for San Francisco housing prices 24:19 ChatGPT as a portfolio manager: what it got right and where it fell short 31:28 Multiple brokerages vs. consolidating: what the AI wealth management plugin said 🔔 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
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    37 mins
  • Spirit Airlines, Rising Insurance Premiums and the $165 Billion Annoyance Economy — Episode 188

    Spirit Airlines, Rising Insurance Premiums and the $165 Billion Annoyance Economy — Episode 188
    May 7 2026

    AJ is in Minneapolis keynoting at NAPFA, so Shane holds down the fort with BKFi Tax Manager, Tiffini Parker. They kick off with the official end of Spirit Airlines and why its collapse is actually bad news for everyday flyers, then Tiffini gives a behind-the-scenes look at tax season at BKFi, four hundred plus returns filed and one of the smoothest seasons yet. From there, they dig into Deloitte and Zoom, trimming parental leave, rising home insurance premiums in unexpected places like Iowa and Duluth, and the Republican proposal to index capital gains to inflation and who it actually benefits.

    They close on the annoyance economy, a New York Times piece revealing that the friction companies build into cancellations and subscriptions costs Americans $165 billion a year. Spoiler: the incentives are all pointing the wrong direction.

    Topics covered:

    • Spirit Airlines shutting down, and what it means for airfare competition
    • BKFi tax season debrief: four hundred plus returns and what changed this year
    • Deloitte and Zoom cutting parental leave, and the ripple effect on the workforce
    • Rising home insurance premiums in unexpected Midwest and Southeast markets
    • The Republican capital gains indexing proposal and who it really helps
    • Backdoor Roths for high income households: still worth it?
    • The annoyance economy and the $165 billion cost of friction

    Timestamps:

    • 00:00 Intro and welcome to Tiffini Parker, BKFi tax manager
    • 00:45 Tiffini's background: Deloitte, Big Four, and her road to BKFi
    • 01:54 Today's episode preview: Spirit, parental leave, insurance, capital gains and more
    • 03:53 Spirit Airlines is officially done, and why that's bad news for flyers
    • 07:16 Tax season debrief: how BKFi handled four hundred plus returns
    • 09:10 Deloitte and Zoom trim parental leave and what it signals for everyone else
    • 11:29 Rising home insurance premiums in places nobody expected
    • 17:16 The Republican capital gains indexing proposal and who it actually benefits
    • 24:12 Backdoor Roths for a $700K household: should they keep going?
    • 25:29 The annoyance economy: cancellations, chatbots and $165 billion in friction

    🔔 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

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

    Two Americas, Financial Infidelity and SpaceX's $60 Billion Bet — Episode 187
    Apr 30 2026
    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 benefitingWhy the Amex CEO's earnings call comments reveal something uncomfortableSpaceX's $60 billion bid for Cursor and the vertical integration playSoftware as the new hardware and why distribution is the new moatFinancial infidelity, secret accounts and the real cost of money secrets in marriageJoint vs. separate finances and what actually works for couples Timestamps: 00:00 Intro and Shane's Ohtani Dodgers jersey from Japan01:53 Today's episode preview: corporate profits, SpaceX, divorce and more03:30 Corporate America is minting money while consumers struggle to buy eggs04:46 The 90% marginal tax rate and what it tells us about wealth inequality08:03 SpaceX wants to buy Cursor for $60 billion and what that actually means11:25 Why distribution is the new moat in the age of AI15:11 Software fatigue is real and why companies are slow to change19:40 Financial infidelity: secret bank accounts and the real cost of money secrets21:37 Joint vs. separate finances and what actually works for couples25:10 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
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    29 mins
  • Money, Kids and Generational Wealth with Special Guest Charlotte Geletka — Episode 186

    Money, Kids and Generational Wealth with Special Guest Charlotte Geletka — Episode 186
    Apr 23 2026
    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 moneyRaising financially grounded children in high net worth householdsAllowances, chores and kid-friendly financial tools like GreenlightInheritances, trust funds, and spendthrift clauses529 plans: who they work for, who they don't, and how to superfund themGenerational wealth vs. generational knowledge Timestamps: 00:00 Intro and welcome to Charlotte Geletka01:09 Charlotte's background, her CFP practice and the children's book03:57 When should you start talking to kids about money? Earlier than you think07:33 How the words adults use around money shape kids' relationship with it09:20 How to raise kids who appreciate what they have without becoming spoiled11:28 Chores, allowances, and giving kids real financial responsibility16:38 Why kids are learning about money from Zillow and TikTok, whether you like it or not19:10 Inheritances, trust funds and what happens when big money meets young adults22:00 529 plans: AJ and Charlotte break down everything you need to know28:01 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
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    31 mins
  • Tax Day Confessions, The Upper Middle Class Trap, and the SpaceX IPO — Episode 185

    Tax Day Confessions, The Upper Middle Class Trap, and the SpaceX IPO — Episode 185
    Apr 16 2026

    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

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

    Episode 184: Expat Retirement Planning, Dual Citizenship Taxes, and the Babylist IPO
    Apr 9 2026

    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

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

    Q1 Market Whiplash, Millionaire Tax Strategies and Bitcoin Backed Mortgages - Episode 183
    Apr 2 2026

    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

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

    BuzzFeed's AI Collapse, Coinbase vs. Big Banks, and the SpaceX IPO Is Official - Episode 182
    Mar 26 2026

    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

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    33 mins