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

Author: Brooklyn Fi

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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.
168 Episodes
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In this episode of The Liquidity Event, AJ and Shane recap Brooklyn FI's estate planning party at Clover Club, complete with notaries, crystal balls, and millennials confronting wills, pets, and chosen family. They also cover the latest economic confusion including layoffs, tariffs, AI fears, the Shrimp Cocktail Index, and California's proposed billionaire tax. Shane breaks down Scaramucci's tariff refund theory while AJ reflects on trust in data, government transparency, and who actually pays for society. The episode closes with questions about corruption, sustainability, and whether two money nerds with a TI 83 could solve the tax code. Key Timestamps: (00:00) AJ's stiff neck and chaotic start (02:39) Estate planning party at Clover Club (04:31) Shane's three-year estate plan procrastination (05:36) Wills, chosen family, and pet guardians (08:09) The lost Tacos and Taxes era (09:26) WARN spikes, layoffs, and missing data (14:32) Scaramucci and the tariff refund theory (16:48) The Shrimp Cocktail Index returns (21:13) California's one-time five percent billionaire tax (30:13) Why neutrality is impossible when policy affects clients   🔔 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  
In this episode of The Liquidity Event, AJ and Shane cover everything from shattered mirrors to shattered housing markets. AJ shares an update on her book deadline and upcoming Thanksgiving travel while Shane recounts a chaotic morning involving a Roomba and a broken mirror. The duo unpack the hidden tax pitfalls of S-Corps in New York City, debate credit card rewards and travel perks, and react to the Frontier Airlines CEO telling customers to buy a backup ticket. They also dive into the strange slowdown in new home sales, the Trump administration's proposed 50-year mortgage, Elon Musk's massive pay package, and whether the AI boom is already bubbling over. Timestamps (00:00) Welcome, introductions, and AJ's end-of-year check-in (01:00) Shane's Roomba disaster and chaotic morning (02:30) AJ's book update and Thanksgiving travel plans (04:00) Delta, Marriott, and Chase credit card strategy for the holidays (08:45) Why S-Corps don't make sense in New York City (12:20) Frontier Airlines CEO tells customers to buy a backup ticket (15:15) AJ on the government shutdown and SNAP benefits (18:15) Housing market troubles and unsold new builds (23:10) The Trump administration's 50-year mortgage proposal (29:45) AI, crypto, and whether the boom is just another bubble   🔔 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  
In this post–Election Week episode of The Liquidity Event, AJ and Shane dive into New York City's new mayor, former rapper Zohran Mamdani, and what his win could mean for taxes, wages, and city life. AJ shares her marathon weekend adventures and Halloween highlights, while Shane talks about biking through Manhattan gridlock, watching Tame Impala, and catching the World Series. They unpack NASCAR champ Kyle Busch's $8.5 million insurance lawsuit, OpenAI's new public benefit status, and the latest push for a global wealth tax. The conversation covers billionaire carveouts, the "Teach for America for failed politicians" idea, and closes with thoughts on fairness, community, and the economics of a changing New York. Timestamps: (00:00) Welcome to The Liquidity Event, marathon weekends, and mime makeup (04:30) Zoran Mammadani wins NYC, a new era (and some saber-rattling) (06:00) AJ's "Teach for America, but for failed politicians" proposal (07:30) Shane's Tame Impala flex, Game 7 chaos, and fall weekend vibes (09:30) NASCAR's Kyle Busch sues Pacific Life, insurance gone wild (14:00) OpenAI's $500B milestone and the rise of "too big to fail" tech (20:00) The great wealth tax debate, guillotines, Birkins, and billionaire tears (27:00) Universal healthcare dreams and the Brooklyn FI insurance saga (32:00) Mamdani's 2% millionaire tax, free buses, and grocery-store wars (39:00) Closing thoughts, fairness, optimism, and five-star requests 🔔 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  
In this Halloween-week episode of The Liquidity Event, AJ and Shane gamble their way through Atlantic City stories, poker scandals, and billionaire luck. AJ checks in from self-imposed exile at the Jersey Shore to finish her book (and avoid the casinos), while Shane shares his thoughts on gambling's strange evolution from high stakes to digital dopamine. The duo dives into Governor JB Pritzker's million-dollar Vegas win, a sprawling FBI gambling case that reads like Ocean's Eleven, and the Louvre jewel heist that has everyone rooting for "Flappy." They debate whether Bitcoin counts as investing or just fancy gambling, share their favorite open enrollment hacks, and field a listener question about when it's okay to stop sweating the $6 latte. They wrap up with a surprisingly heartfelt segment on digital estate planning—passwords, personal finance apps, and the love letter your will should be. Timestamps: (00:00) Welcome to The Liquidity Event — AJ live from Atlantic City (02:00) Halloween plans, weddings, and the curse of the off-season boardwalk (04:30) AJ and Shane head to San Diego for the Personal Financial Planning Summit (06:00) Gambling talk — JB Pritzker's million-dollar win (09:00) FBI's "Operation Royal Flush" and NBA gambling scandals (13:00) Ocean's Eleven in real life — marked cards and the legend of "Flappy" (15:30) The Louvre jewel heist and Shane's power tools (17:00) AI gone too far — Sora, deepfakes, and existential dread (18:00) JP Morgan's Bitcoin collateral move — investing or gambling? (20:00) Open enrollment season tips and why life insurance still matters (23:30) FSAStore.com, sponsorship dreams, and practical tax hacks (24:00) Listener question: when did you stop caring about small purchases? (27:00) Behavioral finance, Faulkner envy, and the psychology of frugality (28:00) Digital estate planning and your "password love letter" (33:00) Personal Capital, Mint, and the problem with dying apps (34:00) Closing thoughts — lattes, legacies, and leaving clean spreadsheets 🔔 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  
In this episode of The Liquidity Event, Shane and guest host Ed Z cover everything from Nobel laureates disappearing into the woods to Italy's flat-tax paradise for the ultra-rich. They unpack why more working-class Americans are turning to the stock market, debate whether democratized investing is empowerment or gambling, and answer a listener question about why companies are staying private longer. The duo also tackles Reddit's $750,000 cash conundrum, the truth about life insurance "wealth hacks," and end on chess, broken office chairs, and the art of tax-season survival. Timestamps: (00:00) Shane's office chair falls apart — chaos at tax day HQ. (02:00) Meet guest host Ed Z (04:15) Disney planning with AI — Shane and Ed test ChatGPT's travel agent skills (06:30) The government shutdown, Epstein theories, and suit shopping with AI (07:25) Nobel laureate goes missing — why geniuses love the woods (09:30) Italy's "La Dolce Vita" flat-tax scheme for the ultra-rich (13:00) Corruption, $1 Italian homes, and Shane's mafia jokes (15:00) The working class joins Wall Street — Robinhood, risk, and returns (19:00) Why democratizing investing is both thrilling and terrifying (20:00) Listener question: why aren't companies going public anymore? (24:00) Private money, long horizons, and the rise of private equity ETFs (26:30) Reddit question: what to do with $750,000 in cash (29:00) Life insurance "wealth hacks" and why caps on returns are a scam (31:30) Chess, Fabiano Caruana, and why Shane's the only spectator in St. Louis 🔔 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  
In this episode of The Liquidity Event, AJ and Shane cover everything from IPOs making a comeback to Hamburger Helper as a recession indicator. They dive into venture-backed companies finally going public, debate whether Hamburger Helper sales say more about wallets or Ozempic, and unpack why America's biggest companies can't quite explain the upside of AI. The duo close out with a lively discussion on the Chase Sapphire Reserve's new $800 fee, what makes rewards cards worth it, and why being a "deadbeat" might actually be a compliment in the credit card world. Timestamps:  (01:20) Hot dogs, nutritionists, and the dangers of Hamburger Helper.  (03:16) Fall in Brooklyn, waffles in Shane's background, and Mikey's Pies.  (05:00) Conference recap – XYPN in Austin  (07:05) Looking ahead to the AICPA Personal Financial Planning Symposium in San Diego.  (08:15) IPOs are back – Figma, Klarna, StubHub, and more.  (14:04) Hamburger Helper as a recession indicator – joy vs. budgets.  (16:53) Grocery inflation, rice and beans, and sardines as a distressed shopper's delight.  (18:32) AI hype vs. reality – what America's top companies aren't saying.  (22:35) Nuclear power, Chernobyl obsessions, and AI's potential to cut through noise.  (25:47) Chase Sapphire Reserve hikes to $800 – perks, pitfalls, and who it's really for.  (29:44) Why business owners get a "cheat code" with rewards cards. 🔔 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  
In this episode of The Liquidity Event, AJ and Shane return from the Future Proof Wealth Management Festival with stories of Weezer, Bush, and the perils of leaving conferences too early. They dig into a New York Times article about using ChatGPT to tackle credit card debt, from spreadsheets to selling watermelons, and debate whether AI is democratizing financial advice or just creating quirky side hustles. The duo also unpack the harsh realities of sudden windfalls, from Powerball winners to stock concentration, and field a listener question about holding too much employer equity in retirement. Along the way, AJ champions late-night networking, Shane shouts out his accountability coach, and both remind us: diversify, diversify, diversify. Timestamps (00:34) Intro – Ally Jane Ayers and Shane Mason kick off Episode 158. (01:18) Ally's "radio host" voice and Shane's zen brain. (02:12) Shoutout to Sherry Mason Real Estate in Cape Coral, FL. (03:22) Segues gone wrong and the Future Proof conference in Huntington Beach. (05:17) Conference quirks – Weezer, Third Eye Blind, Blues Traveler, and Bush. (07:02) Why AJ always leaves early and Shane always stays late. (09:13) Conference strategy – accountability coaches, goals, and nighttime networking. (12:04) "Your soulmate is at the afters" and why happy hours matter. (12:34) NYT article – using ChatGPT for financial advice and debt payoff. (14:37) Success stories – spreadsheets, budgeting, plasma donations, and almost selling feet pics. (16:06) Access and immediacy – why AI fills a gap financial advisors can't. (17:38) Reflections on Brooklyn FI's early late-night client meetings. (18:46) Lottery winners and hard lessons ahead of the $1.8B Powerball. (20:50) Quick Picks vs. lucky numbers – let the computer decide. (22:40) AJ's advice for sudden money windfalls – spend 1% and get a care team. (23:59) Shane's fantasy purchases: boat or flashy watch. (24:41) Building your financial "care team" for long-term stability. (25:35) Listener question – is 50% in one stock too much? (27:23) The risks of concentration and why diversification matters. (28:34) AJ's plan: sell 25% now, the rest over three years, or gift it. (30:20) Imagining being the kids of parents who "don't care" about millions. (30:41) Closing – diversify, send us your financial questions, or just post them on Reddit. 🔔 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  
In this episode of The Liquidity Event, Shane (aka Delta Juan Enjoyer) joins Ally to unpack Taylor Swift and Travis Kelsey's engagement and why it's a perfect case study in prenups. They explore the promise (and hype) of an AI-powered stethoscope, debate private equity's push into 401(k)s, and tackle a listener question about selling real estate with a $600K tax bill. Along the way, AJ shares a personal story about her parents' divorce, Shane muses on Blank Street Coffee, and the duo circle back (again and again) to the question of what truly makes for financial happiness. (00:34) Intro – Ally Jane Ayers and Shane Mason kick off Episode 157. (01:09) Austin's Juan in a Million & Private Equity "-ification" joke. (01:38) Episode topics preview – Taylor & Travis engagement, AI stethoscope, ETFs vs. stocks (03:22) Taylor Swift & Travis Kelsey engagement discussion (06:23) What prenups actually cover & why they matter (13:03) New AI-powered stethoscope & medical tech (17:03) Is it really AI, or just data comparison? (20:22) Private equity is trying to disrupt 401(k)s (23:40) Why this threatens retirement savings & financial security (27:16) Example: Blank Street Coffee & private equity "ruining" businesses (28:58) Listener question – real estate sale with $600K tax bill (31:05) Advice: simplicity vs. 1031 exchange (33:39) Risks of relying only on real estate in retirement 🔔 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  
In this episode of The Liquidity Event, AJ and Shane dive into how they're using AI in everyday life, from food tracking to coding help, before tackling bigger questions about money, dating, and the future of work. They unpack OpenAI's bold claim that AGI could make money obsolete, break down the latest IRS updates—including changes to Qualified Small Business Stock—and debate whether it's better to be a public or secret billionaire. (00:02:00) Shane Talks About Camp (00:09:20) Shane's AI Experiments & Selling His Boat (00:13:00) Money and Modern Dating (00:18:00) OpenAI and the "End of Money" (00:24:00) Burning Man & Billionaire Pizza Analogy (00:26:00) IRS Updates & The Big Beautiful Bill (00:30:00) Public vs Secret Billionaires 🔔 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  
In this episode of The Liquidity Event, John guest stars alongside AJ to celebrate and mourn the end of AOL dial-up after 30 years, reminiscing about AIM screen names along the way. They dive into AI's role in everyday life, from fixing your Dyson to shaping the hiring and job application process, and explore creative childcare alternatives (Auntie AJ is available for a modest $10k). They also discuss the four-day work week, calculating your net worth, and offer guidance on leveraging a million dollars and optimizing your savings. (00:00) Introductions - John guest stars! (01:00) AJ and John give you their best dial-up impression (02:19) Can AI fix your Dyson products? (03:21) Can you define moving the ball forward? (04:27) AI aiding the hiring and job application process (08:33) JohnTFO and PeachesNPunk bid their farewell to AIM and dial-up (12:28) Creative solutions to childcare alternatives (Hint, Auntie AJ will do it for a small fee of $10k) (17:59) Why the four-day work week is working and how you could benefit from it (21:45) How do you calculate your own net worth? (24:47) Read AJ's newest Substack post to find out if you're saving enough money (26:30) Reddit Question: What is the best way to leverage a million dollars? (30:16) How a financial planner thinks you should allocate your savings account for the maximum benefit 🔔 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  
In this episode of The Liquidity Event, Shane and Kurtis dive into the start of Tax Planning Season at BKFi, unpack Figma's billion-dollar breakup, and discuss when employees can finally sell their shares. They explore why Silicon Valley's free perks are disappearing, what the rise of generally intelligent AI could mean for your work, and how new rules are letting you put real estate, crypto, and private equity into your 401(k). Plus, the debate over being friends with your kids, whether spending 60% of your net worth on a "forever home" is ever a good idea, and a fresh take on the "core and explore" investing strategy. (00:00) Introductions - Kurtis guest stars! (02:27) BKFi Clients, it's TPS season! (formerly YEP) (03:28) Figma goes through a billion-dollar breakup (08:47) When can Figma employees sell their shares? (09:32) No more nap pods or free lunches in Silicon Valley (12:56) AI that is generally intelligent (ChatGPT 5) (19:33) Real estate funds, cryptocurrency, and private equity are allowed in 401k's now?! (26:15) Can you be friends with your kids? FAAFO (29:42) Should you spend 60% of your net worth on your "forever home?" Find out what a BKFi senior financial planner has to say! (33:01) Core and explore 🔔 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  
In this episode of The Liquidity Event, AJ and Shane reflect on their first-ever company retreat where AJ admits to being a sore loser, break down the surprising connection between Toys R Us and crypto, and explain why you should give your parents a secret code word to avoid AI scams. Plus, the latest on UK tax loopholes, how many streaming apps are too many, Iceland's new four-day work week, and a few surprising lessons about monetizing unused flights and hotel rooms. (00:00) Introductions (01:09) Certified pre-owned food (02:48) Are home renovations ever finished in their projected time window? (03:42) BKFi client event and classic, corporate forced fun work retreat (04:35) Give your parents a code word, don't let them get scammed by AI (10:06) Will you buy the new Apple flip phone? (14:10) AJ is a sore loser at the first company retreat (16:35) How are Toys R Us and Crypto related? (22:44) Be real, how many streaming apps does your household use? (24:40) Shane doesn't know the difference between Gossip Girl and Gilmore Girls (25:38) Lifesyles of the rich and the famous, they're always complaining, always complaining - How the infamous Good Charlotte song applies to the new closed tax loophole in the UK (31:41) Iceland approved a new four-day work week (35:07) Monitizing your own unused flights and hotel rooms 🔔 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  
On this episode of The Liquidity Event, AJ and Shane are finally reunited, and they cover everything from Missouri's wild proposal to eliminate capital gains tax to why the return-to-office push might be hurting women more than expected. Plus, Greece's crumbling infrastructure, sky-high babysitting rates, revoked science grants, and how to track down your long-lost 401(k). Oh… and of course, a little pasta talk. Key Timestamps: (00:00) Introductions (02:37) Where in the world has Shane been? (05:21) Greece's crumbling infrastructure and economy (09:51) AJ's childhood neighbor has a fascinating way of cooking chicken (11:00) A new bill in Missouri could eliminate capital gains altogether (16:00) Why women are struggling with returning to work in the office (hint, they're not) (20:37) Babysitters make HOW much money in 2025? (21:13) Is New York the place for you? (Go read AJ's Substack, Money Changes Everything, to get the low down) (24:10) Capitol Hill Science fair - Grants get revoked (29:05) Check the lost and found for your old 401(k)   Want to know more about the One Big Beautiful BillTax and how it will affect you, register here for our webinar on July 23. We'll explain everything you need to know.    🔔 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  
What's in the One Big Beautiful Bill Act — and how does it impact your taxes, family, equity comp, and retirement? In this episode of The Liquidity Event, AJ Ayers and John Owens break down the OBBB and what it means for high earners, tech professionals, parents, retirees, and everyone in between. We also chat micro-retirements, the new NYC mayor, charitable gifting changes, and yes, beavers with zoning issues. Key Timestamps: (00:00) Introductions (03:09) Zohran Mamdani the new mayor of NYC (07:30) Gen Z discovers micro-retirement and taking vacations (11:01) Beavers build a local dam in the Czech Republic while authorities await permit (12:54) One Big Beautiful Bill: What does this mean for Brooklyn Fi clients? (14:49) OBBB and QSBS (18:23) What does the OBBB have to do with parents of young children? (22:34) BKFi Boomers: What can the OBBB do for senior citizens (26:01) How to give back to those negatively affected by OBBB (28:03)Charitable Gifting Changes and the OBBB (31:09) Listener Question: How do I find the right accountant?   If you're still curious about the One Big Beautiful Bill and how it will affect you, register here for our webinar on July 23. We'll explain everything you need to know.    🔔 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    
John Owens CFP®, EA, ECA, CPWA® and Ed Zolotarev CPA, MST, CFP® fill in for AJ and Shane on this milestone 150th episode of The Liquidity Event. FICO (Fair Isaac Corporation) is finally figuring out what to do about your outstanding Klarna loans. We discuss how "buy now, pay later" services might soon impact your credit score.   TLDR: It probably isn't the best idea to finance your DoorDash order over 4 months. Plus, alternative investments are getting a lot of attention right now.  Why are private equity firms suddenly sliding into your DMs?  We examine the dry IPO market as one of the root causes. Then a Reddit question: how many kids should you have from a financial perspective?  Finally, our biggest takeaways from the first half of 2025. Key Timestamps: (6:25) FICO's buy now, pay later integration rollout (9:30) Why financing experiences is financial quicksand (12:20) Ed's Affirm baby monitor financing experiment (15:56) Alternative investments moving down market (19:20) Why the IPO drought is forcing PE firms to get creative (24:10) Reddit question: How many kids should you have? (29:25) First half of 2025 takeaways 🔔 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: https://www.linkedin.com/company/brooklyn-fi/ Instagram: https://www.instagram.com/brooklyn_f.i/    
Hear your Liquidity Event host, Ally Jane Ayers, share expert insights on budgeting, investing, and managing money on the Hello Prenup Podcast with Julia Rodgers, Esq. AJ discusses how to take control of your personal finances, talking money in a relationship, and why a prenup is an important part of financial wellness. For the video recording, check out the Hello Prenup podcast on YouTube. Key Moments: 01:51 Critiquing Traditional Finance 06:51 Importance of Prenups 09:33 Starting Money Conversations w/ Partner 12:52 Quarterly Money Dates & Goal Planning 16:47 Student Debt Conversation 20:25 Prenups in Practice 30:29 Budgeting & 50/30/20 Rule 37:22 Inheritance Conversations 44:10 Teaching Kids about Money
While our team is on a quick break, tune in as our co-founder Shane Mason joins the always entertaining Accounting High podcast to talk about the journey of building BKFi.    Shane shares insights on BKFi's team structure and remote work and how we have built a company culture that's ALWAYS focused on how to best serve our clients. He also discusses his and AJ Ayers' new Gemifi software for equity compensation and how they have leveraged marketing partnerships to drive growth. Check out the Accounting High podcast on YouTube. Key Moments: 00:28 Welcome Back Shane and BrooklynFI   09:59 Team Structure and Remote Work   13:04 Client Services and Financial Planning   22:28 The Liquidity Event Podcast   25:36 New Ventures: Gemify Software   34:50 BrooklynFI's Continued Success   35:30 Marketing Strategies and Partnerships   40:26 Investment Strategies and Market Insights 46:41 Final Thoughts and Advice
In this episode, AJ and Shane break down why every VC-backed IPO in the past 12 months has been a "down round" and what that means for your equity. Then they tackle a juicy Reddit question from a 32-year-old tech worker vesting $400,000 per month (!) who's considering walking away from $5 million in future equity. Key Timestamps: (0:00) Introductions and summer traipsing vs. gallivanting exploration (4:40) IPO "down rounds" explained (8:45) The economics behind down rounds: cheap COVID money meets high interest rates (12:30) Circle and Chime IPO examples - companies going public at lower valuations (15:45) Why tender offers might be your best bet in this market (17:45) Reddit question: "Is $10 million enough to retire on?" (21:00) The $400K per month dilemma - stay for more money or quit while ahead? (26:30) Team Quit vs. Team Stay - Opposing views on leaving $5 million on the table (29:30) What being really rich buys you (spoiler: private jets) The Debate: AJ argues for quitting: Take the money, buy the house, live the good life before kids arrive. Shane argues for staying: You're making $3,000 per hour.  Don't walk away from generational wealth. Who's right? Let us know in the comments. 🔔 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: https://www.linkedin.com/company/brooklyn-fi/ Instagram: https://www.instagram.com/brooklyn_f.i/
In this episode of The Liquidity Event, hosts Shane Mason (reporting from Ireland! ) and AJ Ayers discuss the showdown between President Trump and Harvard and some of the current cash challenges felt by universities, even those with massive endowments. They also talk through the IPO market ecosystem and which factors may be keeping it frozen. Key Takeaways: (0:00) Introductions and AJ's Broadway theater review  (4:18) Shane reports from Ireland, scotch eggs & shoutout to Rubin (6:07) Trump vs Harvard - theories on the real motivation  (12:17) College endowments cash crunch - Harvard's $86B problem  (14:28) Endowment size reality check and college reunion prep  (18:33) Should we tax endowments like billionaires?  (21:05) Meet the portfolio pruner - VCs' new cleanup crew  (26:28) The valuation baggage problem and down rounds  (28:26) Secondary sales surge as IPO market stays frozen  (31:00) Sequoia's "patient capital" and wealth inequality connection    🔔 Subscribe to The Liquidity Event on YouTube: YouTube Channel 🌐 Learn more about Brooklyn FI financial planning: www.brooklynfi.com ✍️ Leave us a voicemail question for a future episode: memo.fm/theliquidityevent 📱 Follow Brooklyn FI:  LinkedIn: https://www.linkedin.com/company/brooklyn-fi/ Instagram: https://www.instagram.com/brooklyn_f.i/
In this episode of The Liquidity Event, AJ Ayers hosts two Chief Investment Officers, Peter Lazaroff CFA, CFP® from Plancorp and Rubin Miller CFA from Peltoma Capital Partners, for a chat on cash management strategies, investment philosophies, and calling BS on industry trends.   Key Timestamps: (0:00) Introductions and background (2:48) Career paths in investment management (12:43) Cash management strategies in today's high-interest environment (13:57) Risk-free rates and building portfolios around them (30:00) Tax loss harvesting: overhyped or valuable strategy? (31:13) Direct indexing and SMAs - worth it or not? (37:01) Dumbest purchases - from $13k couches to levered ETFs   🔔 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: https://www.linkedin.com/company/brooklyn-fi/ Instagram: https://www.instagram.com/brooklyn_f.i/
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