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

It's Tax Day, and AJ is joined by Senior Financial Planner Ed Zolotarev for a wide-ranging episode that covers estate planning horror stories, AI models going rogue, and why older Americans keep getting richer while everyone else treads water.

They kick things off with a fascinating New York Times story about a professor who left a $6.4 million estate to a political organization he cared about in the 1980s, never updated his will, and now his family is suing to get the money back. AJ and Ed break down who should get it, what the law says, and what the real lesson is for anyone who has not looked at their beneficiaries recently. Then it's on to an Anthropic AI model that went rogue and submitted a fake anonymous tip to Philadelphia's unsolved murders database, which the police flagged as spam, but Anthropic did not find out about for three months.

They also cover Anthropic's Investor Day and what it signals about the timing of an IPO, a Wall Street Journal piece on why affluent older Americans have seen their net worth grow 37% since the pandemic while younger generations are stuck at 4%, and what a potential Fed rate hike means for clients trying to make housing decisions right now.

Topics covered:

• Tax Day PSA: Please respond to your accountant
• Estate planning horror story: $6.4 million meant for a political org and a family that disagrees
• The importance of updating your beneficiaries and your will
• Anthropic AI model submits fake tip to Philadelphia unsolved murders database
• Anthropic Investor Day and what it signals about the IPO timeline
• Affluent older Americans are up 37% since the pandemic. Everyone else, not so much
• A potential Fed rate hike and what it means for housing decisions
• Reddit question on overspending with a high income

Timestamps:

• 00:52 Tax Day PSA and the client who reformed after being put on the shit list
• 04:15 Estate planning horror story: $6.4 million and the Democratic Socialists of America
• 07:30 Who should get the money and what the law actually says
• 09:30 Donor-advised funds and why you need to leave instructions
• 10:45 Anthropic AI model submits a fake tip to Philadelphia's unsolved murders database
• 15:45 Anthropic Investor Day and what it signals about the IPO timeline
• 18:45 Affluent older Americans up 37% since the pandemic, while younger generations sit at 4%
• 24:45 A potential Fed rate hike and what it means for clients making housing decisions
• 28:30 Who actually got those 2.5% mortgages in 2020 and 2021
• 31:30 Reddit question on overspending with a high income and Pokémon cards as an investment

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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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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

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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

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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

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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 529
• Tech layoffs at Google, TikTok, Etsy, and Zillow, and the AI elephant in the room
• The 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 know
• Do 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

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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 combined
• The Supreme Court ruling that opened the floodgates for online gambling
• YC founder asks job seekers to tattoo the company logo for an interview
• Is 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 expires
• AI 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

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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 cameras
• Why 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-IPO
• How 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 exemption
• New 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

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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 work
• The 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 force
• The 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?

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Shane and Ethan are back, and the World Cup jerseys are out. Episode 195 covers the Jersey Mike's IPO and the Forbes disclosures revealing that family members collected around thirty million dollars in compensation ahead of the company going public, Jeff Bezos co-leading an AI startup called Prometheus and declaring that AI will make single income households viable again, and Vinod Khosla's ten billion dollar purchase of the Seattle Seahawks plus the 20-year beach access lawsuit he has been fighting with the state of California.

They also break down New York City's new pied-à-terre tax targeting non-resident property owners and what it actually means for people like Ken Griffin who own a $238 million penthouse but live in Florida, and close with a Reddit question from a business owner going from $500K to three million dollars in income who wants to know what to do with his money and why Reddit keeps telling everyone not to hire a wealth advisor.

Topics covered:

• Jersey Mike's IPO valuation and the family compensation disclosures
• Bezos is co-leading an AI startup, and his case for AI optimism
• Vinod Khosla is buying the Seattle Seahawks for $10 billion
• The 20-year beach access lawsuit and how it went to the Supreme Court
• New York City's pied-à-terre tax explained and who it actually affects
• Reddit question: business owner going from $500K to $3M in income needs a plan
• Why Reddit keeps telling people not to hire a wealth advisor and what to do instead

Timestamps:

• 00:00 Intro, World Cup jerseys, and the Argentina vs England matchup
• 03:15 Jersey Mike's IPO and the family nepo baby compensation disclosures
• 07:00 Bezos co-leads AI startup Prometheus and says AI will fix the economy
• 09:30 Vinod Khosla buys the Seattle Seahawks for $10 billion
• 11:45 The 20-year California beach access lawsuit that went to the Supreme Court
• 14:00 Khosla Ventures and the investments that made him fantastically wealthy
• 15:10 New York City's pied-à-terre tax and Ken Griffin's $238 million penthouse
• 20:15 Reddit question: $3M income S corp owner needs a financial plan
• 24:00 Why Reddit tells everyone not to hire a wealth advisor and what to do instead

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