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

Brooklyn Fi
  • 4.8 (19)
  • Investing
  • 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. 9h ago

    Anthropic's IPO, California's Billionaire Tax and Social Security's Dirty Secret — Episode 204

    AJ is joined by Stu Connelly for his very first podcast appearance. They dive straight into the Anthropic public S-1, what it reveals about the company and what it means for employees who are about to go through one of the largest IPOs in history. They also get into the uncomfortable truth about Social Security's 3.6% COLA increase and why a raise for seniors could actually accelerate the timeline to benefit cuts for everyone under 40. Then it's on to California's proposed Prop 40 billionaire wealth tax, Larry Page spending $173 million on a Miami compound to potentially dodge $15 billion in taxes, and Mark Zuckerberg threatening to leave California and somehow convincing Meta's board to create an entirely new class of stock just to protect his 60.6% voting control. Topics covered: Anthropic's public S-1 and what it reveals about the company's place in the world Why late-in-the-year IPOs are a tax nightmare for employees with RSUs IRS installment agreements and why they don't work the way most people think The ANT ticker symbol and why the Canadian company was apparently totally fine with it Social Security's 3.6% COLA increase and why it could deplete the trust fund faster California's Prop 40 billionaire wealth tax and who is trying to dodge it Larry Page's $173 million Miami compound and the $15 billion tax dodge Zuckerberg's new Class C stock and what it means for Meta shareholders Why employees with equity in publicly traded companies should stop tracking the stock price daily Timestamps: 00:52 Welcome to Stu Connelly and his very first podcast appearance 02:00 Anthropic's public S-1 and what it means for employees 04:15 Why late-in-the-year IPOs create tax nightmares for employees with RSUs 06:00 IRS installment agreements and why they are based on your assets 07:30 The ANT ticker symbol and the ant colony as an AI metaphor 09:15 Below on Apple TV, Josh Hartnett and Jaws meet Gilmore Girls 10:45 Social Security's 3.6% COLA increase and why it could be bad news for younger generations 13:30 California's Prop 40 billionaire wealth tax and who is trying to dodge it 16:00 Larry Page's $173 million Miami compound and the $15 billion tax dodge 21:00 Zuckerberg threatens to leave California, and Meta creates a new class of stock to keep him   🔔 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

  2. Oct 22

    Trump Accounts Get Complicated, SpaceX Lockup Updates and 351 Exchanges After the IRS Ruling — Episode 203

    Shane and AJ are back, spooky season is in full swing, and AJ's book comes out in three weeks. They kick things off with a Reddit question from someone who has a Finnish sauna, a Turkish bath, a cold plunge, and a heated pool, and just wants to redo their spa. AJ and Shane weigh in. Then it's into the articles. The Wall Street Journal has new details on Trump accounts, including a rule that allows individual stock contributions and a new auto-enrollment mechanism. AJ is broadly in favor of the concept and broadly annoyed at the potential for corporate abuse. Anthropic has committed 5% of its shares to a public benefit fund ahead of its IPO, which AJ and Shane think is the right instinct even if the PR is a little much. SpaceX stock is up 50% since its IPO, and the lockup release data is encouraging, with most unlocked shares not flooding the market as everyone feared. They close with the IRS ruling on 351 exchanges and what it actually means for advisors and clients with concentrated positions. Spoiler: it is not as bad as it sounds, and Brent Sullivan of Tax Alpha gets a well-earned shout-out. Topics covered: Reddit question: How do I redo my spa with a Finnish sauna, Turkish bath, cold plunge, and heated pool? Trump accounts: new auto-enrollment rules and individual stock contributions explained The corporate abuse edge case that has AJ worried about Trump account contributions Anthropic commits 5% of shares to a public benefit fund ahead of IPO SpaceX stock is up 50% since IPO, and what the lockup release data actually shows Why phantom income from vested but unsellable shares is the worst type of income 351 exchanges: what the IRS ruling actually closed and what is still viable Shout out to Brent Sullivan of Tax Alpha and his concentrated position strategies Timestamps: 00:52 Halloween costumes, Dr. Shots, and AJ's book coming out November 10th 03:45 Reddit question: How do I redo my spa? 07:30 Trump accounts: auto-enrollment and new individual stock contribution rules 10:15 The corporate abuse edge case and why AJ is worried 13:00 Anthropic commits 5% of shares to a public benefit fund ahead of IPO 16:30 AI optimism vs doom and the Elizabeth Holmes documentary conspiracy theory 19:00 LinkedIn bots, Russian bot farms, and Elon's response to Anthropic's announcement 22:30 SpaceX stock up 50%, and what the lockup release data actually shows 27:00 Phantom income, double triggers, and what the December lockup means for employees 29:00 351 exchanges after the IRS ruling: what closed and what is still viable   🔔 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

  3. Oct 16

    Estate Planning Gone Wrong, Anthropic's Investor Day and Rising Interest Rates — Episode 202

    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 🔔 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

  4. Oct 8

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

    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?   🔔 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

  5. Sep 24

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

    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

  6. Sep 10

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

    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

  7. Aug 27

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

    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

  8. Aug 13

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

    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 🔔 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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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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