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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