Spies in FinTech, Tax Shakedowns, & Surviving Market Storms
The Liquidity Event | Money and Finance with Shane and Ally Jane
Release Date: 05/20/2025
IPO Down Rounds & Why Tender Offers May Be Your Best Bet in this Market
The Liquidity Event | Money and Finance with Shane and Ally Jane
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...
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Trump vs Harvard, College Endowments and Why the IPO Market is Still Frozen
The Liquidity Event | Money and Finance with Shane and Ally Jane
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 -...
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Cash Management & Investment Strategies with CIOs Peter Lazaroff & Rubin Miller
The Liquidity Event | Money and Finance with Shane and Ally Jane
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...
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Spies in FinTech, Tax Shakedowns, & Surviving Market Storms
The Liquidity Event | Money and Finance with Shane and Ally Jane
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...
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Market Myths BUSTED, CEO Burnout & The Great Credit Card Rip-Off
The Liquidity Event | Money and Finance with Shane and Ally Jane
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) -...
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AJ Ayers on The Long Term Investor: Got Stock Options? Don’t Miss These Year-End Moves
The Liquidity Event | Money and Finance with Shane and Ally Jane
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...
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NSOs Explained: Don't Let Your Non-Qualified Stock Options Expire Worthless
The Liquidity Event | Money and Finance with Shane and Ally Jane
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...
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7+ Lessons from 7 Years: Entrepreneurship, Taxes & Building a Business
The Liquidity Event | Money and Finance with Shane and Ally Jane
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...
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Tariff Chaos, Circle IPO & Angel Investing
The Liquidity Event | Money and Finance with Shane and Ally Jane
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...
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Corporate Espionage, AI Exam Hacks & Money Questions From Reddit
The Liquidity Event | Money and Finance with Shane and Ally Jane
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: Leave a voicemail: memo.fm/liquidityevent Don't...
info_outlineWelcome 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
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