Episodes
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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/
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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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Missing episodes?
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Welcome to Episode 146 of The Liquidity Event!
This week AJ and Shane talk FinTech corporate espionage and then focus on the proposed GOP tax plan.
To wrap things up, they address a listener's concern about preparing for a "coming economic storm," offering insights on why fear-based financial decisions are rarely the best approach.
Key Takeaways:
(00:00) - Intro & What's Shane doing in AJ's house?
(01:52) - Spies Are Everywhere: The Cutthroat FinTech Industry
(04:54) - Remote Work & Cybersecurity: The New Frontier of Corporate Risk
(06:07) - Non-Competes: Enforceable or Not?
(06:33) - Decoding the New House GOP Tax Plan (Draft Details!)
(06:53) - AJ's Favorite: 529 Plan Expansions for Certifications!
(08:14) - Shane's Take: Standard Deductions, AMT, and the SALT Cap Saga Continues
(12:23) - No Tax on Tips? Or Overtime? The Complications!
(15:14) - Radical Tax Idea Corner: Capital Gains & Lifetime Exclusions
(18:58) - Estate Tax Exclusion: Permanent and Higher?
(19:48) - Listener Question: Preparing for the "Coming Economic Storm"
(21:26) - AJ's Hot Take: Don't Make Decisions Based on Fear!
(25:01) - Outro
🔔 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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Welcome to Episode 145 of The Liquidity Event! This week, AJ and Shane tackle some big topics: Are individual investors smarter than the "smart money" hedge funds? Why are CEOs really heading for the exits at record rates (and what's the deal with that vasectomy shirt story)? Plus, we unravel the frustrating Catch-22 of credit card fees for businesses and consumers.
Tune in for our signature blend of financial insights and (mostly) educational humor!
Key Timestamps:
(0:00) - Intro & Shane's Renovation Woes
(01:39) - Market Update: Pros Sold, Individuals Pounced – Who Was Right?
(06:30) - Hedge Fund Reality Check: S&P 500 vs. "Expert" Performance
(09:00) - The "Tiger in the Grass": Why We're Biased Towards Action in Markets
(14:50) - AJ's Big News: Announcing Her Book "Creative Money"!
(17:10) - Tipping Fatigue: Are We All Fed Up?
(21:40) - The Real Reasons Tipping Culture is Out of Control
(24:45) - The Great Credit Card Rip-Off: Fees, Oligopolies & The Catch-22 for Businesses
(28:20) - CEO Exodus: Why Leaders Are Quitting in Droves
(29:05) - Peak Ambiguity: AI, DEI & The Hilarious "Vasectomy Shirt" Anecdote
(30:00) - Burnout is the New Black: The Serious Side of CEO Turnover
Connect with us:
Email your financial problems or questions: [email protected]
Leave us a voicemail (we might play it on the air!): memo.fm/liquidityevent
Don't forget to LIKE, SUBSCRIBE, and leave us a REVIEW if you enjoy the show! Your support helps us expose more financial nonsense.
#FinancialPodcast #InvestingMyths #CEOBurnout #CreditCardFees #SmallBusinessFinance #MarketAnalysis #StockMarket #Leadership #BKFi #LiquidityEvent
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Hear your host, AJ Ayers, share her expertise on equity compensation as a special guest on Peter Lazaroff’s podcast, The Long-Term Investor!
In this focused conversation, AJ shares insights on critical year-end tax planning, developing multiyear strategies for stock options and RSUs, managing risk, preserving gains, and simplifying selling strategies.
For the video recording, check out the Long Term Investor podcast on YouTube.
Key Moments:
(00:37) - Year-End Tax Planning for Equity Comp
(03:54) - Long-Term Equity Strategy & Diversification
(09:24) - Exercising Private Company Stock Options
(14:10) - Managing Equity Compensation Risk
(22:27) - Advanced Tactics for Mixed Equity Packages
(25:38) - Strategies to Minimize Taxes on Gains
(32:49) - Automated Selling with 10b5-1 Plans
(34:56) - Final Tips & Takeaways
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In this episode of The Liquidity Event, AJ and Shane talk non-qualified stock options (NSOs), explaining the common mistakes people make, tax implications, and strategic approaches to maximize your equity compensation.
Key Timestamps:
(00:00) - Intro and a few laughs
(03:45) - The biggest mistake with NQSOs
(06:45) - How taxation works upon exercise
(10:15) - NQSOs and Alternative Minimum Tax
(15:45) - Multiple grant strategies: the Goldilocks approach
(19:45) - When to exercise and hold vs. wait
(23:30) - The "least regret" strategy
(26:15) - Overconfidence and substantial risk of forfeiture
(28:45) - Real-world Reddit question about forgotten options
Connect with us: Email: [email protected]
Ask us financial questions via voicemail: memo.fm/liquidityevent
Don't forget: please like, subscribe, and leave a review!
#EquityCompensation #StockOptions #NQSOs #FinancialPlanning #TaxStrategy
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Happy 7th Anniversary to Brooklyn Fi! 🎉 In this special episode of The Liquidity Event, Shane Mason & AJ Ayers reflect on the seven biggest lessons they've learned running a financial planning firm for seven years (though they might have come up with more than seven!).
From the surprising rewards (and demands) of entrepreneurship to navigating hiring challenges, managing relationships, and the power of 'disagree and commit,' they share candid insights for anyone running or thinking about starting a business.
Plus, they tackle a listener's question about handling an unexpected, large tax bill when income is lumpy – learn about IRS installment plans and other options.
⏱️ Timestamps:
(00:00) - Intro, Happy Tax Day & Shane's Stained Shirt
(02:48) - Listener Voicemail: Handling a Surprise Tax Bill
(05:11) - Brooklyn FI's 7th Anniversary: Intro to 7 Lessons in 7 Years
(07:37) - Lesson: The Uncapped Reward of Entrepreneurial Hard Work (Shane)
(11:28) - Lesson: Burn the Candle in Your 20s (Shane)
(17:26) - Lesson: Entrepreneurship as a Creative Act (Shane)
(20:03) - Lesson: Work on Relationships (Coworkers, Employees, Vendors) (Shane)
(21:19) - Lesson: Why Hiring Your First Employees is So Hard (AJ)
(23:05) - Lesson: The Power of 'Disagree and Commit' (AJ)
(24:42) - Lesson: Steal Like an Artist (Borrowing Ideas) (Shane)
(28:45) - Final Thoughts & Would They Do It Again?
🔔 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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Market shocks, crypto moves, windfalls, and punk rock?
Shane Mason & AJ Ayers unpack the latest financial news and listener questions in this episode of The Liquidity Event.
🚨 IMPORTANT NOTE: This episode was recorded on April 8th, 2025, before the April 9th pause on most newly proposed U.S. tariffs (excluding China). While our specific tariff critique reflects the situation known at that moment, the policy landscape remains dynamic and could change again.
Therefore, our discussion on the history of U.S. tariffs and the fundamental pros and cons of using them in economic policy offers valuable context for understanding potential future shifts.
In this episode, hear AJ's sharp critique of the initial approach to the widespread tariff proposal and the market uncertainty it created. We also break down the Circle (USDC) stablecoin IPO filing – what does it mean for crypto and digital dollars?
Plus, practical advice for tackling angel investing after an inheritance, and the story of how Henry Rollins got a Brooklyn FI Roth IRA t-shirt!
⏱️ Timestamps:
(00:00) - Intro & Catching Up (Mexico, California, Remembering Grandpa)(03:09) - The Roth IRA / Henry Rollins T-Shirt Story
(06:45) - Tariff Turmoil: Discussing the Initial Broad Proposal (Recorded BEFORE Pause News)
(08:15) - Historical Tariffs & Manufacturing Job Trends
(10:40) - Critiquing the Abrupt Policy Rollout Strategy
(13:50) - Context: Existing China Trade Friction & Why Tariffs Elsewhere?
(16:40) - Potential Business & Personal Impacts of Widespread Tariffs
(18:05) - Circle (USDC) Stablecoin IPO Filing: What You Need to Know
(19:40) - Explainer: How Stablecoins Like USDC Work & Generate Revenue
(21:15) - The International Use Case for Digital Dollars vs. Traditional Banking
(24:30) - Reddit Q&A: Angel Investing an 8-Figure Inheritance?
(25:40) - Key Advice for Aspiring (or Accidental) Angel Investors
(27:10) - Alternatives: Angel Investing ETFs & Pre-IPO Funds
(28:15) - Outro & How to Connect
🔔 Subscribe to The Liquidity Event on YouTube: https://www.youtube.com/@brooklynfi/?sub_confirmation=1🌐 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/
#LiquidityEvent #BrooklynFI #PersonalFinance #Investing #Economics #Tariffs #TradePolicy #MarketVolatility #Crypto #Stablecoin #USDC #IPO #AngelInvesting #WealthManagement #Fintech #Podcast #FinancialPlanning
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In this episode of The Liquidity Event, AJ and Shane dive into tech drama, AI disruption, and financial advice with a little spice.
Key Timestamps:
(00:00) - Intro & Japan Travel Reflections
(03:00) - Corporate Espionage: Rippling vs Deel
(13:06) - Student Uses AI to Beat Amazon Interview
(18:00) - Hinge Health: Revolutionizing Physical Therapy?
(23:24) - Listener Question: Best Retirement Account for Musicians
(28:00) - Reddit Question: 26-Year-Old Making $400K From Business
Like us? Have financial questions? Connect with us.
Email: [email protected]
Leave a voicemail: memo.fm/liquidityevent
Don't forget to like, subscribe, and leave a review! New episodes every Friday.
#FinancialAdvice #CorporateEspionage #AIEthics #RetirementPlanning #Entrepreneurship
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In this episode of The Liquidity Event, BKFi’s AJ Ayers and Eduard Zolotarev tackle market volatility head-on, explore the recent Taco Bell product launch event, and share honest thoughts on Dave Ramsey's controversial rental property comments.
Key Timestamps:
(00:00) - Intro & Episode Overview
(00:34) - Meet Ed & An All Important Update on Taco Bell
(03:33) - Market Volatility & Recent Corrections (We aren’t scared)
(08:49) - Long-Term Market Performance Charts
(13:05) - Why Timing the Market Is So Hard (and pointless)
(17:20) - Lessons from Those Who Left the Market in 2008
(21:43) - Global Investment Beyond US Markets
(23:23) - Dave Ramsey's Controversial Comments
(29:19) - The Value of Having a Financial Advisor
Don't forget to like, subscribe, and leave a review! New episodes every Friday.
If you have anything to add, comment below! We value thoughtful & intelligent perspectives.
Connect with us: Email: [email protected]Leave a voicemail: memo.fm/liquidityevent
#FinancialAdvice #IPO #StartupTips #AIInfrastructure #TacoBell
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In this special episode of The Liquidity Event, BKFi leaders John and AJ interview tax attorney Christopher Karachale about Qualified Small Business Stock (QSBS) - a powerful tax benefit allowing founders to exclude up to $10 million (or more) from capital gains taxes when selling shares.
Key Timestamps:1:50 - What is QSBS? The $10 million exclusion explained
3:16 - History of QSBS: From 1992 to today's 100% exclusion
8:15 - Qualification requirements: Company & shareholder criteria
11:13 - "Qualified trade or business" explained
12:18 - Prohibited business categories
14:14 - Tips for founders to qualify for QSBS
18:30 - LLC conversion strategies for QSBS
20:45 - Fixing past entity mistakes to qualify
22:54 - LLC to C-Corp conversion: FMV basis benefit
26:15 - 1045 rollovers: Strategy for selling before 5 years
29:04 - QSBS stacking: Advanced strategies with trusts
35:38 - Practical advice for early-stage founders
Connect with us: Email: [email protected] Leave a voicemail: memo.fm/liquidityeventDon't forget to like, subscribe, and leave a review! New episodes every Friday.
#FinancialAdvice #IPO #StartupTips #AIInfrastructure #Entrepreneurship
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In this episode of The Liquidity Event, AJ and Shane analyze CoreWeave's transformative journey from crypto trading platform to AI infrastructure powerhouse & share highly anticipated Initial Public Offering (IPO) tips, plus unfiltered advice on what it really takes to start a business (from two people who actually did it).
Key Timestamps:
0:00 - Intro & Market Updates
2:51 - The IPO Market Landscape 2020-2025
8:49 - What Does CoreWeave Actually Do?
10:37 - CoreWeave's Explosive Revenue Growth
11:56 - Risk Factors: Microsoft Concentration
14:53 - Founders' $150M Pre-IPO Cash Out
19:23 - GPU Infrastructure & Market Position
21:33 - Starting a Business Reality Check
24:00 - The Truth About Side Hustles
25:42 - Why "Setting Your Own Hours" is a Myth
29:00 - Basic Excel Skills: Non-Negotiable
31:35 - Software vs Revenue: What to Prioritize
32:20 - Do You Really Need an LLC?
34:15 - The Truth About Business "Write-offs"
37:22 - Business Plans: Necessary or MBA Fluff?
40:16 - Final Thoughts on EntrepreneurshipConnect with us: Email: [email protected] Leave a voicemail: memo.fm/liquidityevent
Don't forget to like, subscribe, and leave a review! New episodes every Friday.
#FinancialAdvice #IPO #StartupTips #AIInfrastructure #Entrepreneurship
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In this episode of The Liquidity Event: Money & Finance with AJ and Shane, we explore how demographics shape friendship networks, examine Elon Musk's exaggerated claims about DOGE savings, and answer a retirement planning question from a business owner.
Key Timestamps:
0:34 - Introduction and episode topics
1:55 - Mexico City update and lifestyle chat
3:17 - Billionaire Brian Johnson's extreme anti-aging efforts
6:18 - AJ's Certified Exit Planning Advisor (CEPA) designation
9:04 - Hedonic vs. eudaimonic happiness discussion
12:21 - How demographics and education affect friendship patterns
16:18 - Analysis of gathering spaces and COVID's impact on socializing
21:22 - DOGE's questionable $55 billion savings claims
24:24 - Concerns about public lands and national parks
25:24 - Reddit Q&A: Should you contribute to self-employed 401k or Roth 401k? -
In this episode of The Liquidity Event: Money & Finance with Shane and AJ, we unpack everything you need to know about Incentive Stock Options (ISOs) - from basic tax implications to advanced strategies for maximizing your equity compensation.
Key Timestamps:
0:28 - Introduction to Incentive Stock Options (ISOs)
10:26 - Why ISOs get special tax treatment
13:29 - Exercising ISOs: Common pitfalls and best practices
15:45 - Case Study: Recovering $50k in lost tax credits
23:52 - The 5% rule: When to exercise your ISOs
25:39 - Breaking down ISO exercises into manageable chunks
27:28 - AMT credits explained: Getting your money back
28:30 - Year-end timing strategies for ISO exercises
31:28 - How to avoid losing valuable tax creditsConnect with us: Email: [email protected]
Leave a voicemail: memo.fm/theliquidityevent/
Please like, subscribe, & leave us a review! New episodes drop every Friday.
#EquityCompensation #StartupLife #StockOptions #PersonalFinance #TaxStrategy #FinancialPlanning #WealthManagement #TechCompensation
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In this episode of The Liquidity Event: Money & Finance with Shane and AJ, we discuss Spotify's soaring stock price, the reality of New York real estate's "open secret," and why successful entrepreneurs struggle to relax even after achieving their goals.
Key Timestamps:
0:01 - Intro and Valentine's Day musings
6:48 - Spotify's journey from IPO to $620/share
8:44 - Evolution of Spotify's equity compensation
11:21 - The Great Wealth Transfer and NYC real estate secrets
15:52 - Millennial housing affordability crisis
19:48 - Are things really better for our generation?
22:02 - Listener Question: Tax strategy for high-earning couple
30:32 - Tax optimization strategies for business ownersConnect with us: Email: [email protected] Leave a voicemail: memo.fm/liquidityevent
Don't forget to like, subscribe, and leave a review! New episodes every Friday.
#FinancialAdvice #WealthManagement #EquityCompensation #Entrepreneurship #PersonalFinance
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In this week's episode of The Liquidity Event: Money & Finance with Shane and AJ, we tackle Trump's tariffs, humanoid robots in manufacturing, and baby boomer women deciding the fate of trillions of dollars.
Key Timestamps:
0:00 - Intro and updates
4:44 - Baby boomer women & the $82T great wealth transfer
10:29 - Humanoid robots: Manufacturing's future
16:06 - Breaking down Trump's trade war with Mexico & China
22:59 - The impact on domestic manufacturing
27:19 - Reddit Q&A: Real estate diversification strategies
Connect with us:
Email: [email protected]
Leave a voicemail: memo.fm/liquidityeventDon't forget to like, subscribe, and leave a review! New episodes every Friday.
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Join AJ Ayers, CFP®, EA, CEP, and John Owens, CFP®, EA, ECA, CPWA® as they dive into the biggest financial headlines of early 2025, from AI market shakeups to real estate trends and credit score strategies. Plus, they tackle a listener question about luxury car decisions when you've "made it."
Key Moments:
0:36 - Welcome & 2025 check-in
5:42 - Deep Seek's AI breakthrough and market impact
12:01 - Making sense of market headlines and volatility
15:06 - Credit score gaming: privilege and problems
19:37 - Denver's rental market "plunge" explained
22:52 - Reddit Question: $6M net worth car buying dilemmaWatch for insights on:
How AI developments are affecting the market
Why credit score systems may need reform
Real estate market cycles
Luxury car buying vs leasing debate
Don't forget to like, subscribe, and leave your questions in the comments! New episodes every Friday.
#FinancialAdvice #AINews #PersonalFinance #StockMarket #TechNews #MoneyTips
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In this episode of the Liquidity Event: Money and Finance with Shane and Ally Jane, we cover everything you need to know about RSUs, from basic tax implications to advanced strategies for managing your equity compensation.
Key Timestamps:
0:28 - Introduction to RSUs & today's topics
6:38 - What makes RSUs unique among equity compensation
9:20 - How RSUs vest & the one-year cliff explained
12:33 - Tax implications: The crucial moment of vesting
22:08 - Understanding RSU withholding challenges
24:19 - Double trigger RSUs explained
27:09 - Sell to cover strategy breakdown
31:02 - Watch out for wash sales with RSUs
32:39 - Blackout periods (preview for future episode)Connect with us: Email: [email protected]
Leave a voicemail: memo.fm/theliquidityevent/
Don't forget to like, subscribe, and leave a review! New episodes every Friday.
#FinancialAdvice #RSUs #StockOptions #TechNews #PersonalFinance
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In this episode, AJ & Shane discuss Alaska Airlines' ambitious challenge to Delta, financial frauds in the FinTech space, and tackle a trending Reddit question about timing your exit.
KEY MOMENTS:
[2:25] - AJ's Punishment Travel Story: Getting stranded in a Mississippi blizzard
[7:20] - Alaska Airlines vs Delta: Breaking down their new international routes, premium offerings, and what it means for the airline industry's recovery
[11:28] - Financial Fraud: How a Fidelity employee stole $750k from stock plans and why Deel's $12B platform is facing money laundering allegations
[21:04] - The $2M Question: Should you take guaranteed money now or wait for a potentially bigger payday?
[26:54] - Financial Advisor's Perspective: Strategies for minimizing regret in exit timing and why taking some chips off the table might be your best betConnect with us: Email: [email protected]
Leave a voicemail: memo.fm/heliquidity
Don't forget to like, subscribe, and leave a review! New episodes every Friday.
#FinancialAdvice #StartupLife #StockOptions #TechNews #PersonalFinance
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Happy 2025! Ally Jane and Shane kick off the year with a deep dive into which major private companies might finally go public.
From SpaceX to Canva, we break down who's ready to make the leap (and who's still playing the IPO waiting game). Plus, an honest discussion about reaching financial independence and whether FIRE is all it's cracked up to be. Society isn’t built for early retirement. What happens if you’re rich and have lots of free time with no one to share it with?
Key Moments:
0:00 Welcome to 2025 & reflections on 2024
5:51 IPO Market Analysis: From winter to spring? A look at the numbers
13:34 Deep dive into potential 2025 IPOs (Canva, DataBricks, Rippling & more)
20:37 The Mystery Trip Reveal: Shane's diabolical plan for AJ
24:31 Real Talk: When reaching financial independence isn't what you expected
Between Shane plotting AJ's mystery destination and frank discussions about post-FIRE regret, this episode balances market insights with real talk about money and life.
And yes, there's a detour into dental drama because even financial advisors have to deal with crown complications. 🦷
Want more insights on equity compensation and financial planning? Visit us at brooklynfi.com
Follow us:
Instagram: @brooklyn_f.i LinkedIn: /brooklyn-fi
Twitter: @BrooklynFi
#FinancialPlanning #IPO #FinancialIndependence #TechIPO #EquityCompensation #FIRE #PersonalFinance
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