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The Liquidity Event

The Liquidity Event

By: Brooklyn FI
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Summary

 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. Career Success Economics Personal Finance
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
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