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 

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🌐 Learn more about Brooklyn FI financial planning: www.brooklynfi.com

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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/

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/

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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

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

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

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?

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🌐 Learn more about Brooklyn FI financial planning: brooklynfi.com

✍️ Leave us a voicemail question for a future episode:memo.fm/theliquidityevent

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LinkedIn: https://www.linkedin.com/company/brooklyn-fi/

Instagram: https://www.instagram.com/brooklyn_f.i/

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

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🌐 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

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

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