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. 1d ago

    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

  2. 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

  3. 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

  4. Aug 6

    Gambling Is Now America's Favorite Pastime, The OpenAI vs Anthropic IPO Race and AI Solopreneurs — Episode 198

    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 🔔 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. Jul 30

    Flock Safety Under Fire, SpaceX's IPO Disaster and the Millennial Wealth Split — Episode 197

    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 🔔 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. Jul 23

    AI Bodyguards, Childcare Deserts and Private Market FOMO — Episode 196

    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? 🔔 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. Jul 16

    Nepo Sandwich Babies, Billionaires Buying Sports Teams and the Pied-à-Terre Tax — Episode 195

    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 🔔 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. Jul 1

    Bobby Bonilla Day, Sports Team Valuations and the Rise of Women's Sports — Episode 194

    Happy Bobby Bonilla Day. Every July 1st, the New York Mets pay Bobby Bonilla $1.2 million, and they will continue to do so until 2035. It is one of the most entertaining stories in the history of sports finance, and it involves Bernie Madoff, a deferred annuity, and a baseball player who got cut in 1999 and is still cashing checks. In Episode 194 of The Liquidity Event, AJ is joined by Kody Sherlund to break down why Bobby Bonilla Day is actually a masterclass in the time value of money, how Shohei Ohtani's $680 million deferred contract with the Dodgers is the modern version of the same story, and why buying a sports franchise has quietly been one of the best investments of the last 15 years. The Clippers sold for $2 billion in 2014 and are now worth $7.5 billion. The Knicks are worth $10 billion. The annualized returns rival the S&P 500. They also get into the rise of women's sports and why the money is finally following the talent, the NCAA's name, image, and likeness revolution, and what it actually means for 19-year-olds suddenly holding seven-figure endorsement deals, and why sports gambling is the PSA nobody asked for, but everyone needs. Topics covered: Bobby Bonilla Day explained, and the time value of money behind the deal Bernie Madoff's role in the Mets' deferred payment decision Shohei Ohtani's $680 million deferred contract with the Dodgers Why buying a sports franchise has been one of the best investments of the last 15 years The Clippers, the Knicks, and how sports team valuations have exploded The rise of women's sports and the investment opportunity it represents NCAA name, image, and likeness and what it means for college athletes financially Sports gambling and why it ruins people's lives Timestamps: 00:00 Intro, Happy Bobby Bonilla Day, and the Knicks' historic comeback 02:32 Bobby Bonilla Day explained and the time value of money 04:06 Bernie Madoff's role in the Mets' deferred payment decision 05:08 Shohei Ohtani's $680 million deferred contract with the Dodgers 07:09 Why investing in sports franchises has been such a great bet 09:53 The Clippers sold for $2 billion in 2014 and are worth $7.5 billion today 12:49 The rise of women's sports and the investment opportunity it represents 17:45 NIL deals, college athletes getting paid, and what it means financially 23:08 The cottage industry of financial advisors targeting college athletes 25:15 Sports gambling PSA and why it ruins people's lives 🔔 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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