Episodes

  • Bobby Bonilla Day, Sports Team Valuations and the Rise of Women's Sports — Episode 194

    Bobby Bonilla Day, Sports Team Valuations and the Rise of Women's Sports — Episode 194
    Jul 1 2026
    Happy Bobby Bonilla Day. Every July 1st, the New York Mets pay Bobby Bonilla $1.2 million, and they will continue to do so until 2035. It is one of the most entertaining stories in the history of sports finance, and it involves Bernie Madoff, a deferred annuity, and a baseball player who got cut in 1999 and is still cashing checks. In Episode 194 of The Liquidity Event, AJ is joined by Kody Sherlund to break down why Bobby Bonilla Day is actually a masterclass in the time value of money, how Shohei Ohtani's $680 million deferred contract with the Dodgers is the modern version of the same story, and why buying a sports franchise has quietly been one of the best investments of the last 15 years. The Clippers sold for $2 billion in 2014 and are now worth $7.5 billion. The Knicks are worth $10 billion. The annualized returns rival the S&P 500. They also get into the rise of women's sports and why the money is finally following the talent, the NCAA's name, image, and likeness revolution, and what it actually means for 19-year-olds suddenly holding seven-figure endorsement deals, and why sports gambling is the PSA nobody asked for, but everyone needs. Topics covered: Bobby Bonilla Day explained, and the time value of money behind the deal Bernie Madoff's role in the Mets' deferred payment decision Shohei Ohtani's $680 million deferred contract with the DodgersWhy buying a sports franchise has been one of the best investments of the last 15 yearsThe Clippers, the Knicks, and how sports team valuations have explodedThe rise of women's sports and the investment opportunity it representsNCAA name, image, and likeness and what it means for college athletes financially Sports gambling and why it ruins people's lives Timestamps: 00:00 Intro, Happy Bobby Bonilla Day, and the Knicks' historic comeback 02:32 Bobby Bonilla Day explained and the time value of money 04:06 Bernie Madoff's role in the Mets' deferred payment decision 05:08 Shohei Ohtani's $680 million deferred contract with the Dodgers 07:09 Why investing in sports franchises has been such a great bet 09:53 The Clippers sold for $2 billion in 2014 and are worth $7.5 billion today 12:49 The rise of women's sports and the investment opportunity it represents 17:45 NIL deals, college athletes getting paid, and what it means financially 23:08 The cottage industry of financial advisors targeting college athletes 25:15 Sports gambling PSA and why it ruins people's lives 🔔 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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    27 mins
  • SpaceX IPO Day, AI Cybersecurity Risks and When an S Corp Actually Makes Sense — Episode 193

    SpaceX IPO Day, AI Cybersecurity Risks and When an S Corp Actually Makes Sense — Episode 193
    Jun 25 2026
    AJ is joined by Ethan, BKFi's bookkeeper extraordinaire and tax expert, for a wide-ranging episode recorded on the actual day of the SpaceX IPO. They dig into whether SpaceX should be fast-tracked into the S&P 500, what BKFi clients with the opportunity to buy shares at IPO price should actually be thinking about, and a Brooklyn brownstone being listed for Anthropic stock that is either clever marketing or a sign of the times. Then it's on to a Reuters story about hackers using Meta's AI chatbot to breach high-profile Instagram accounts, what it means for protecting your financial data in the age of AI, and Americans leaving the US in record numbers for the first time since the Great Depression. Plus a website called isaiprofitableyet.com that is tracking one very simple question. They close with a listener question about whether a small business owner making $95K in profit should elect S corp status, and Ethan breaks down exactly when it makes sense and when it does not. Topics covered: SpaceX IPO day and the 12-month S&P 500 waiting period Should you buy shares at the IPO price? What BKFi tells clients Brooklyn brownstone listed for Anthropic stock and Bitcoin Meta's AI chatbot breach and cybersecurity risks in the age of AI Americans leaving the US in record numbers, and the tax consequences of renouncing citizenshipIs AI profitable yet? The website is tracking it in real timeS corps: when they make sense and when they don't for small business owners Timestamps: 00:00 Intro, Summer Fridays, and Ethan's fishing plans in Oxford, Mississippi 01:39 Today's episode preview and SpaceX IPO day 03:31 SpaceX and the 12-month S&P 500 waiting period 04:31 Should you buy shares at the IPO price? What BKFi tells clients 08:27 Brooklyn brownstone listed for Anthropic stock and Bitcoin 12:11 The tax consequences of selling your home for stock 14:45 Meta's AI chatbot breach and what it means for your financial security 17:13 Americans leaving the US in record numbers, and the citizenship question 22:24 Is AI profitable yet? Introducing isaiprofitableyet.com 28:00 Listener question: When does an S Corp actually make sense? 🔔 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
  • Slumlord Training Camp, AI's Two Track Labor Market and the Nest Egg Protection Act — Episode 192

    Slumlord Training Camp, AI's Two Track Labor Market and the Nest Egg Protection Act — Episode 192
    Jun 18 2026
    AJ is fresh off the best concert of her life, and Shane is headed to the World Cup, so episode 192 kicks off with appropriate energy before diving into some of the meatiest topics the pod has covered in a while. They start with a Wall Street Journal piece about an elite retreat where children of ultra-high-net-worth families learn how not to blow their inheritance. AJ renames it Slumlord Training Camp, and she is not wrong. The conversation turns into a broader discussion about wealth hoarding, trickle-down economics, and why the top 0.001% of Americans added $2.7 trillion in wealth between 2020 and 2025 — roughly 250 people, for the record. From there, AJ and Shane dig into PwC's report on how AI is splitting the labor market into two distinct tracks, what it means for entry-level workers, and why your intern is now literally Claude. They also break down Zillow's latest housing market report and why you should always read the fine print on who is paying for the research. And they close on the Nest Egg Protection Act, a Republican proposal to give homeowners over 65 a one-million-dollar capital gains exclusion, and why AJ thinks we will never hear about this bill again. Topics covered: The R365 retreat for ultra high net worth kids and what it actually teaches them Wealth hoarding, trickle-down economics, and the $2.7 trillion wealth increase for 250 Americans PwC's two-track AI labor market report and what it means for entry-level workersWhy radiologists and developers are thriving in the AI era Zillow's housing market update and why you should read who funded the researchThe Nest Egg Protection Act and a one-million-dollar capital gains exclusion for homeowners over 65AJ's book Creative Money: New Financial Rules for Artists, Innovators, and Misfits Timestamps: 00:00 AJ went to Rosalía at MSG, and it was the best show of her life 03:17 Shane is wearing a Colombia jersey and headed to the World Cup 05:30 The Wall Street Journal's elite retreat, where wealthy kids learn not to blow their inheritance 10:41 The $2.7 trillion wealth increase for the top 0.001% and why this is getting out of control 15:06 PwC's AI labor market report: the two-track economy and what it means for entry-level workers 19:15 Why companies using AI are hiring more, not less 21:52 Zillow's housing market update and the fine print on who benefits 24:09 The Nest Egg Protection Act: a one million dollar capital gains exclusion for homeowners over 65 30:53 Why this bill is not a real solution to housing inventory 35:35 AJ's book Creative Money and a teaser for next week's Peter Thiel secret society episode 🔔 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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    35 mins
  • The Economics of Egg Freezing, Fertility's Last Taboo and Building Cofertility with Special Guest, Lauren Makler — Episode 191

    The Economics of Egg Freezing, Fertility's Last Taboo and Building Cofertility with Special Guest, Lauren Makler — Episode 191
    Jun 11 2026
    AJ is joined by special guest Lauren Makler, co-founder and CEO of Cofertility, for one of the most honest and eye-opening conversations The Liquidity Event has had to date. Lauren spent almost a decade at Uber before founding Cofertility, a company that helps women freeze their eggs for free when they donate half of the eggs retrieved to intended parents who need an egg donor to have a baby. AJ and Lauren dig into the real economics of egg freezing, what it actually costs in 2026 with and without employer coverage, and why the window in which you benefit most from egg freezing is almost always the window in which you can least afford it. They also get into third-party reproduction, why egg donation is fertility's last taboo, and how Cofertility is flipping the traditional transactional model on its head. The conversation goes deeper from there, covering what it is like to raise money as a woman for a women's health startup, why getting men to actually take their paternity leave might be one of the most powerful things we can do to advance workplace equity, and the biggest misconception Lauren hears about fertility that she wishes she could correct at scale. Topics covered: How Cofertility's split program works and who it is designed forThe real cost of egg freezing in 2026 with and without insurance Third party reproduction and why egg donation is fertility's last taboo Freezing eggs vs. freezing embryos and what the science actually says Raising money as a woman for a women's health startupHow to pressure your employer to offer better fertility benefitsWhy equal parenting at home is the key to workplace equity Timestamps: 00:00 Intro and welcome to Lauren Makler, co-founder and CEO of Cofertility 01:37 How Cofertility works and why Lauren founded the company 03:56 Why egg donation pricing felt like surge pricing and how Cofertility changed it 05:35 What egg freezing actually involves, explained simply 08:34 What does egg freezing cost in 2026 with and without employer coverage 11:03 How long can frozen eggs last and what the science says about vitrification 13:30 A real case study of Cofertility's split program in action 19:39 What it is like raising money as a woman for a women's health startup 25:34 How to pressure your employer to offer better fertility benefits 30:33 The biggest misconception about egg freezing, Lauren wishes she could correct 🔔 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
  • Carta's Equity Proposal, Oura Ring's IPO and Robinhood's AI Trading Tool — Episode 190

    Carta's Equity Proposal, Oura Ring's IPO and Robinhood's AI Trading Tool — Episode 190
    Jun 4 2026
    IPO season is heating up and AJ and Shane West are back after a whirlwind few weeks that included a company retreat upstate, a client event in Williamsburg, the launch of Gemifi at FPA NorCal in San Francisco, and a pod of orcas off the coast of Seattle. In Episode 190 of The Liquidity Event, they dig into Carta's proposal to allow employees to contribute vested equity directly into a 401k or IRA, and whether it actually helps everyday startup employees or just adds another tax break for the wealthy. They also break down Oura Ring's confidential IPO filing, why wearable health tech is having a moment, and whether the growth story holds up once everyone who wants one already has one. Then it's on to Fidelity's Q1 2026 retirement analysis, which shows record high contributions to retirement accounts while the K-shaped economy quietly widens. Robinhood's new AI trading tool gets the full treatment, including whether letting a bot make credit card purchases is innovation or a liability waiting to happen. And AJ has thoughts on Phoebe Gates closing a $35.5 million oversubscribed Series A while calling herself a scrappy startup. Topics covered: Carta's proposal to put vested equity into 401k and IRA accountsOura Ring confidential IPO filing and the wearable health tech wave SpaceX IPO lockup period and what it means for employees with equity Anthropic confidential S1 and the 2026 IPO pipeline Fidelity Q1 2026 retirement analysis and record high 401k contributions Robinhood AI trading tool and using natural language to invest Phoebe Gates, nepo babies and a $35.5 million Series A Timestamps: 00:52 Shane West, the Mexico World Cup and two weeks of nonstop travel 02:52 Company retreat upstate, client events and the launch of Gemifi in San Francisco 05:16 Carta's proposal to contribute vested equity directly into a 401k or IRA 09:03 The steel man case for Carta's proposal and who it actually helps 11:54 Oura Ring files confidentially for IPO and the wearable health tech wave 15:38 Fidelity Q1 2026 retirement analysis and record high 401k contributions 18:43 43% of stock plan participants became first-time investors through equity comp 19:00 Robinhood lets customers use AI to trade stocks and make credit card purchases 23:26 SpaceX IPO lockup period, Anthropic S1 and the 2026 IPO pipeline 24:36 Phoebe Gates raises a $35.5 million Series A and says she is not a nepo baby 🔔 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
  • 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