Épisodes

  • 7% Mortgages, Oura Ring Pulls Its IPO and Could AI Empty Your Bank Account? — Episode 201

    7% Mortgages, Oura Ring Pulls Its IPO and Could AI Empty Your Bank Account? — Episode 201
    Oct 8 2026

    Shane and AJ are back together after XYPN in San Diego, and they have a lot to catch up on before getting into the articles. There's the St. Louis gunfight origin story, AJ's viral BQE Instagram post that her PR team took a little too seriously, Mayor Mamdani fixing potholes, and Shane's Mexico City neighbor group chat situation.

    Then they get into it. The Wall Street Journal says 7% mortgage rates are wrecking the homebuyer playbook, and AJ, a current 7.875% mortgage holder with a condo board lawsuit on her hands, has thoughts. Scott Bessent is comparing Trump accounts to the GI Bill, and AJ has a lot of thoughts about that, too, including a deep dive into redlining and a book recommendation. Oura Ring has postponed its $2 billion IPO, which Shane and AJ saw coming, and they break down what it signals for the broader IPO pipeline, including Anthropic and OpenAI.

    They close with a Journal piece on whether AI could finally convince lazy bank customers to move their money out of low-yield accounts, and a conversation about Instinct, the hot new Silicon Valley AI assistant that saved AJ $45 on a sweater and picked a bar near the B train.

    Topics covered:

    • AJ's viral BQE Instagram post and the PR pitch that should not have happened
    • Mayor Mamdani is actually fixing things in Brooklyn
    • 7% mortgages, locked-in sellers, and why the housing market is the worst of both worlds
    • Trump accounts vs the GI Bill and the redlining connection Scott Bessent is ignoring
    • The Color of Law by Richard Rothstein, a book recommendation
    • Oura Ring postpones its $2 billion IPO and what it means for Anthropic and OpenAI
    • Could AI agents finally move your money out of low-yield bank accounts?
    • Instinct, OpenAI Dots, and delegating cognition to AI agents

    Timestamps:

    • 00:00 Intro, XYPN San Diego recap, and the St. Louis gunfight origin story
    • 03:30 AJ's viral BQE Instagram post and the PR pitch gone wrong
    • 06:30 Mayor Mamdani fixing Brooklyn and Shane's Mexico City neighbor chat disaster
    • 08:00 7% mortgages are wrecking the homebuyer playbook
    • 10:30 AJ's 7.875% mortgage, the condo board lawsuit, and why selling is hard
    • 14:00 Scott Bessent compares Trump accounts to the GI Bill, and AJ pushes back hard
    • 17:30 The Color of Law, redlining, and the Forrest Gump boomer trap
    • 23:00 Oura Ring postpones its $2 billion IPO and what it means for the pipeline
    • 26:00 IPO market update: 110 IPOs, $150 billion raised, and still down 30% from 2021
    • 28:00 Could AI agents empty your low-yield bank account and move it somewhere better?

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    33 min
  • 200 Episodes, the nScale IPO, & Oura Ring Goes Public — Episode 200

    200 Episodes, the nScale IPO, & Oura Ring Goes Public — Episode 200
    Sep 24 2026

    200 episodes. Shane and AJ are back together and they have a lot to catch up on. Ibiza, Future Proof, Martinis and Mortality, and a Time Magazine article about AI that had Shane looking at sailboats. They kick things off with a Substack piece called Travel Isn't a Hobby, whether affluent people who travel constantly are actually enjoying it or just stuck on a hedonic treadmill, and the Japanese concept of misogi, doing something hard once a year and pairing it with something luxurious.

    Then it's on to the nScale IPO, a British company going public in New York with $140 million of its $280 million in revenue not yet materialized, and the Oura Ring IPO, where the entire $2.2 billion raise is going to pay off a VC and cover employee tax withholding rather than grow the company. A viral tweet from a researcher claiming AI will wipe out humanity sent the internet into a panic and may have derailed Anthropic's IPO timeline. Shane has a conspiracy theory about it. They close with a Reddit question from a 36-year-old woman who is already financially independent but can't figure out whether to keep running the family business her dad built.

    Topics covered:

    • Travel Isn't a Hobby: the hedonic treadmill and the misogi concept
    • Future Proof festival recap and Martinis and Mortality event
    • nScale IPO: a house of cards built on contracts that haven't materialized
    • Oura Ring IPO: $2.2 billion raise that goes entirely to pay off a VC and employee taxes
    • How to read an S-1 and what the story they're telling actually means
    • The viral AI doomsday tweet, Shane's conspiracy theory, and the race to regulate
    • Reddit: would you keep running a profitable family business if you were already financially independent?

    Timestamps:

    • 00:00 Intro, episode 200, Ibiza, Italy and Future Proof recap
    • 03:30 Travel Isn't a Hobby: the hedonic treadmill and the misogi concept
    • 07:00 Luxury hotels, the First Class Jerk Substack and pairing hard things with rewards
    • 10:00 Martinis and Mortality: 15 estate plans done in one night
    • 11:30 nScale IPO: a British AI company going public with mostly unearned revenue
    • 15:30 Oura Ring IPO: $2.2 billion raise, none of it going to grow the company
    • 19:00 How to read an S-1 and what investors actually love about subscriptions
    • 22:00 Wall Street banning GLP-1s and the Oura Ring placebo sleep effect
    • 24:00 The viral AI doomsday tweet and Shane's conspiracy theory about OpenAI and Anthropic
    • 28:30 Reddit: financially independent but can't walk away from the family business

    🔔 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 min
  • Rest in Peace Dolly Parton, Summer Reading, and Billionaire Philanthropy — Episode 199¾

    Rest in Peace Dolly Parton, Summer Reading, and Billionaire Philanthropy — Episode 199¾
    Sep 10 2026

    AJ is back, and she brought senior planner Melanie Taylor along for a special episode that has absolutely nothing to do with markets, IPOs, or interest rates and everything to do with books, billionaires, and Dolly Parton.

    AJ and Melanie kick things off with their summer reading lists, trading recommendations on everything from Lonesome Dove and The Historian to Dungeon Crawler Carl and Lena Dunham's memoir Fame Sick. They also dig into the If Books Could Kill podcast and the story of Three Cups of Tea, a book that turned out to be less about building schools in Pakistan and more about a very creative money laundering operation.

    Then it gets a little more serious. AJ pulls the Forbes list of America's most generous philanthropists, and the numbers are not flattering. Charitable giving rose 14% last year, but billionaire fortunes rose 18.5%, meaning the giving is not keeping pace. They also celebrate the life and legacy of Dolly Parton, who died on August 25th at 80 years old and somehow managed to give more meaningfully on a $450 million fortune than most billionaires do with hundreds of billions. They close with a conversation about Trump accounts, donor-advised funds, and how Brooklyn Fi matched employee donations to the Imagination Library in Dolly's honor.

    Topics covered:

    • Summer reading lists: Lonesome Dove, The Historian, Dungeon Crawler Carl, Fame Sick, and more
    • The If Books Could Kill podcast and why Three Cups of Tea was a grift
    • AJ's book Creative Money is coming out on November 10th
    • Forbes list of America's most generous philanthropists and why the numbers are embarrassing
    • Why donor-advised funds create a bottleneck between billionaire giving and the people who need it
    • Dolly Parton's Imagination Library and the economics of her philanthropy
    • Trump accounts: should you open one and should you contribute?
    • Brooklyn Fi matches team member donations to the Imagination Library in Dolly's honor

    Timestamps:

    • 00:00 Intro, welcome Melanie Taylor, and saving episode 200 for Shane and AJ together
    • 01:30 Melanie's summer reads: Dungeon Crawler Carl and Heart the Lover by Lily King
    • 04:00 AJ's summer reads: Lonesome Dove, The Historian, Fame Sick, and London Falling
    • 07:30 Books they DNF'd this summer and the art of abandoning a book
    • 10:00 If Books Could Kill podcast and the Three Cups of Tea money laundering grift
    • 15:30 AJ's book Creative Money is coming out on November 10th
    • 18:30 Forbes list of America's most generous philanthropists and the numbers that don't add up
    • 21:00 Why donor-advised funds create a bottleneck and the Yale endowment problem
    • 24:00 Rest in peace, Dolly Parton, and the economics of her Imagination Library
    • 27:30 Trump accounts: open them, grab the match, but maybe stick with your 529

    🔔 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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    34 min
  • AI Compute Futures, Stripe's Singularity Announcement and Wealth Management's $3 Trillion Problem — Episode 199.5

    AI Compute Futures, Stripe's Singularity Announcement and Wealth Management's $3 Trillion Problem — Episode 199.5
    Aug 27 2026

    Shane is joined by BKFi tax manager Tiffini Parker for a jam-packed half episode covering AI compute markets, Stripe's singularity announcement, wealth management's cash hoarding problem, South Korean dating culture, and a Reddit question that every financial advisor will have opinions about.

    They kick off with AI computing power becoming a tradable futures contract at the CME, what that actually means for transparency in the compute market, and why Stripe buried a four-page memo about the singularity inside an acquisition announcement. Then it's on to the Wall Street Journal's $3 trillion problem — why investors are keeping too much cash in money market funds and why advisors can't seem to convince them otherwise.

    They also cover the dating scene in South Korea, being completely overtaken by Samsung chip engineers and what massive AI-era bonuses are doing to the marriage market, Spirit Airlines' flight attendant data privacy fight against Google's bankruptcy bid, and close with a Reddit question from a $17 million net worth individual who sold his company and wants to know if he should hire a financial advisor. Shane and Tiffini have thoughts.

    Topics covered:

    • AI computing power becomes a tradable futures contract at the CME
    • Stripe says the singularity has started and acquired OpenRouter for billions
    • Wealth management's $3 trillion cash hoarding problem and why advisors are losing the battle
    • Investment-grade bonds, munis, and what advisors are actually recommending
    • South Korea's dating scene is now dominated by Samsung chip engineers
    • Spirit Airlines flight attendants fight to keep their data out of Google's bankruptcy bid
    • Reddit: $17 million net worth, recent company sale, should I hire a financial advisor?

    Timestamps:

    • 00:00 Intro, welcome back, Tiffini Parker
    • 02:30 AI computing power is now a tradable futures contract at the CME
    • 05:30 Stripe says the singularity has started and acquired OpenRouter for billions
    • 09:00 Stripe's valuation, the potential PayPal acquisition, and why it built for AI by accident
    • 12:00 Wealth management's $3 trillion cash hoarding problem
    • 15:00 Why investors don't trust advisors and what it would take to change that
    • 17:30 South Korea's dating scene is now dominated by Samsung chip engineers
    • 21:30 Spirit Airlines flight attendants fight to keep their data out of Google's bankruptcy bid
    • 26:00 Reddit: $17 million net worth, should I hire a financial advisor?
    • 30:00 Why 50 bps is probably worth it and what this person actually needs

    🔔 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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    34 min
  • Trump Accounts, California's Wealth Tax and Do You Actually Need an LLC? — Episode 199

    Trump Accounts, California's Wealth Tax and Do You Actually Need an LLC? — Episode 199
    Aug 13 2026
    Shane and Kody Sherlund are back for episode 199, one away from a big milestone, with a packed slate covering tax policy, tech layoffs, opportunity zones, private fund pitfalls, and California's groundbreaking wealth tax. They kick off with the IRS issuing proposed regulations on employer contributions to Trump accounts, what Section 530a actually means, and where these accounts fit in the order of operations next to a 529. Then it's on to the latest wave of tech layoffs at Google, TikTok, Etsy, and Zillow, whether AI is really the culprit nobody wants to name, and why creative destruction has always worked this way. They also cover Opportunity Zone 2.0 and deferring 2026 capital gains into 2027, the Wall Street Journal's warning that private funds come with big tax bills most people aren't factoring in, and California's new wealth tax, which saw only six billionaires leave but take $27 billion in potential revenue with them. They close with the most common question on the internet: " Do I need an LLC?" Topics covered: IRS proposed regulations on Trump accounts and employer contributions Section 530a explained and where it fits next to a 529Tech layoffs at Google, TikTok, Etsy, and Zillow, and the AI elephant in the roomThe golden era of AI-enabled solopreneurs and creative destruction Opportunity Zone 2.0 and deferring 2026 capital gains into 2027 Private funds come with big tax bills, and most investors are not factoring in California's wealth tax: six billionaires left and took $27 billion with them State clawbacks and what Anthropic employees moving out of California need to knowDo I need an LLC? Yes, and here is why Timestamps: 00:00 Intro, England jerseys, Brighton FC, and Wonderwall at Minnesota MLS games 05:30 IRS proposed regulations on employer contributions to Trump accounts 09:00 Section 530a explained and non-discrimination rules 11:00 Tech layoffs at Google, TikTok, Etsy, and Zillow, and the AI factor 14:30 The golden era of AI-enabled solopreneurs and creative destruction 20:00 Opportunity Zone 2.0 and deferring 2026 capital gains into 2027 26:30 Private funds come with big tax bills; most investors are not factoring in 31:30 California's wealth tax and who actually left 35:00 State clawbacks and what equity comp employees moving out of California need to know 38:00 Reddit: Do I need an LLC? Yes, and here is why 🔔 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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    40 min
  • Gambling Is Now America's Favorite Pastime, The OpenAI vs Anthropic IPO Race and AI Solopreneurs — Episode 198

    Gambling Is Now America's Favorite Pastime, The OpenAI vs Anthropic IPO Race and AI Solopreneurs — Episode 198
    Aug 6 2026
    Shane is joined by senior financial planner Ed Zolotarev for a wide-ranging episode covering gambling, tattoos, sleep trackers, IPO races, and the golden age of the AI solopreneur. They kick off with a Fortune piece revealing that Americans now spend more on sports betting than on movies, art, museums, and music combined, close to $165 billion a year on the books. Shane and Ed dig into who is driving the growth, what the 2018 Supreme Court ruling unlocked, and why the bankruptcies and credit card debt data from legalized-gambling states should have everyone paying attention. Then it's on to a YC founder asking desperate job seekers to tattoo the company logo for an interview, and the New York Times opinion piece on whether all this body data from Oura Rings and WHOOPs is actually making people healthier or just more anxious. They close with the race between OpenAI and Anthropic to be first to IPO, SpaceX's first post-IPO earnings report, which sent the stock down 13% on the day a billion shares were released from lockup, and a Wall Street Journal piece on the growing world of AI-enabled solopreneurs doing millions in revenue with zero employees. Topics covered: Americans spend more on sports betting than on movies, art, museums, and music combinedThe Supreme Court ruling that opened the floodgates for online gamblingYC founder asks job seekers to tattoo the company logo for an interviewIs more body data from wearables actually good for you? A doctor weighs in OpenAI vs Anthropic: who goes public first and why it matters SpaceX first post-IPO earnings: stock down 13% as lockup expiresAI solopreneurs doing millions in revenue with no employees Timestamps: 00:00 Intro, welcome back from paternity leave, Ed! 02:30 Americans spend $165 billion a year on gambling, more than movies, art, and music combined 06:15 Who is driving the gambling boom, and what the 2018 Supreme Court ruling unlocked 09:45 YC founder LemonLime asks job seekers to tattoo their logo for an interview 13:00 Is more body data from wearables actually making people healthier or just more anxious 17:30 The sleep tracker placebo effect and why the doctor stopped wearing hers 20:00 OpenAI vs Anthropic: the race to IPO and why being first matters 23:15 SpaceX first post-IPO earnings: stock down 13% as a billion shares hit the market 26:30 AI solopreneurs: new business formations nearly doubled, and the golden age of the solo founder 31:00 The liability question nobody is asking about AI-built businesses 🔔 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 min
  • Flock Safety Under Fire, SpaceX's IPO Disaster and the Millennial Wealth Split — Episode 197

    Flock Safety Under Fire, SpaceX's IPO Disaster and the Millennial Wealth Split — Episode 197
    Jul 30 2026
    Shane is joined by Kody Sherlund for a packed episode covering surveillance cameras, rocket ships, World Cup tax bills, and why the millennial generation is splitting into two very different financial realities. They kick off with the Flock Safety CEO speaking out after the LAPD suspended use of the company's surveillance cameras, and why Shane thinks "we just read license plates" is not the whole story. Then it's on to Anthropic's unusual plan to allow all employees to submit 10b5-1 trading plans post-IPO, what that actually means for the thousands of people sitting on life-changing equity, and why it is a smarter approach than a traditional lockup. Then they dig into the SpaceX IPO, now one of the worst-performing large IPOs in recent history, down 30% to 40% from its peak and sitting well below its debut price. Shane and Kody break down who was really selling at $200 and who is holding the bag. They also get into Spain, potentially owing the IRS a chunk of its $50 million World Cup prize, the corruption history of FIFA, and new Fed research showing that millennial homeownership and wealth are splitting dramatically based on when you were able to buy a home. Topics covered: Flock Safety CEO speaks out after LAPD suspends its surveillance camerasWhy license plate data is more revealing than Flock wants you to think Anthropic's plan to allow all employees to submit 10b5-1 trading plans post-IPOHow 10b5-1 plans work and why they are better than a traditional lockup SpaceX IPO: down 30% to 40% from its peak, and why retail investors are holding the bag Spain potentially owes the IRS a cut of its $50 million World Cup prize FIFA's corruption history and why it never got a US tax exemptionNew Fed research on the millennial wealth split and the housing supply problem Timestamps: 00:00 Intro, dog days of summer, wedding planning, and the USS Midway 04:15 Flock Safety CEO speaks out after LAPD suspends its surveillance cameras 07:30 Why license plate data is more revealing than Flock wants you to think 10:45 Anthropic considers allowing all employees to submit 10b5-1 trading plans 14:00 How 10b5-1 plans work and why they are smarter than a traditional lockup 18:30 SpaceX IPO: one of the worst large IPOs in recent history 21:00 Who was really selling at $200 and who is holding the bag 24:00 Spain could owe the IRS a cut of its $50 million World Cup prize 26:30 FIFA's corruption history and the hotel lobby bust in Zurich 29:30 New Fed research on the millennial wealth split and the housing supply problem 🔔 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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    36 min
  • AI Bodyguards, Childcare Deserts and Private Market FOMO — Episode 196

    AI Bodyguards, Childcare Deserts and Private Market FOMO — Episode 196
    Jul 23 2026
    Shane and Ethan are back for another week, this time with gin and tonics and World Cup jerseys. Episode 196 covers a Wall Street Journal piece on the AI backlash, which has tech executives hiring bodyguards, installing security measures, and concealing where they work as public sentiment toward AI turns sharply negative. They also dig into Trump's 50% tariff on Canadian goods using a 1930s trade law, the blockbuster wave of new stock issuances that is raising questions about the bull market, and a Business Insider piece on why working moms with children under five are dropping out of the labor force at an alarming rate and what it would actually take to fix it. They close with a Reddit post from someone in the Rich People Personal Finance subreddit who wants exposure to private companies like Anthropic, Stripe, and Eleven Labs through a private-market fund charging 1.5% plus 15% of profits. Shane and Ethan have thoughts on whether that itch is worth scratching. Topics covered: AI backlash and why tech executives are hiring bodyguards and concealing where they workThe sevenfold increase in online threats against AI company employees Trump's 50% tariff on Canadian goods and the 1930 Trade Act Blockbuster stock issuances and what they mean for the bull market Working moms with children under five are dropping out of the labor forceThe childcare desert problem and what employer and government solutions could look like Private market funds: the fees, the FOMO, and whether it is worth it Timestamps: 00:00 Intro, World Cup jerseys, gin and tonics, and The Odyssey review 05:45 AI backlash: tech executives are hiring bodyguards and hiding where they work 09:10 The sevenfold increase in online threats and the DeFlock movement 13:30 Trump imposes a 50% tariff on Canadian goods using a 1930 trade law 17:45 Blockbuster stock issuances and what they mean for the bull market 21:30 Working moms with children under five are dropping out of the labor force 24:00 The childcare desert problem and Shane's hot take on employer-funded solutions 28:15 The man who runs both the IRS and Social Security spied on colleagues at JPMorgan 29:30 Reddit: Should you get exposure to Anthropic and Stripe through a private market fund? 🔔 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 min