The Liquidity Event | Money and Finance with Shane and Ally Jane

Brooklyn Fi
  • 4.8 (19)
  • Investing
  • 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. 3d ago

    Slumlord Training Camp, AI's Two Track Labor Market and the Nest Egg Protection Act — Episode 192

    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 workers Why radiologists and developers are thriving in the AI era Zillow's housing market update and why you should read who funded the research The Nest Egg Protection Act and a one-million-dollar capital gains exclusion for homeowners over 65 AJ'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

    35 min

  2. Jun 11

    The Economics of Egg Freezing, Fertility's Last Taboo and Building Cofertility with Special Guest, Lauren Makler — Episode 191

    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 for The 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 startup How to pressure your employer to offer better fertility benefits Why 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

    33 min

  3. Jun 4

    Carta's Equity Proposal, Oura Ring's IPO and Robinhood's AI Trading Tool — Episode 190

    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 accounts Oura 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

    29 min

  4. May 14

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

    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 reporting What fewer trading windows mean for employees with equity compensation and 10b5-1 plans Gemifi launching at FPA NorCal and what the platform does Rent payments counting towards credit scores and who it actually helps The 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

    37 min

  5. May 7

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

    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

    32 min

  6. Apr 30

    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

  7. 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

  8. 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
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4.8
out of 5
19 Ratings

About

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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