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The Liquidity Event

The Liquidity Event

By: Brooklyn FI
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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. Career Success Economics Personal Finance
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
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