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...

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 Te...

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 (1...

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 po...

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,...

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 Accoun...

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 Correction...

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...

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 Landsc...

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 a...

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 an...

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 co...

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 wi...

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 -...

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 -...

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 f...

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. Wha...

In this final episode of 2024, hosts AJ and John explore the complexities of handling sudden unexpected windfalls, major financial decisions like purchasing a home (or vacation home), and some last-minute year-end planning tips.   Key Moments & Topics: 0:00 Show introduction and 2024 wrap-up The psychology of sudden wealth and how to avoid common pitfalls 4:35 Handling unexpected windfalls Smart s...

In this episode of The Liquidity Event, hosts AJ and Shane discuss year-end business planning and tax optimization strategies.   They break down: Essential business credit card decisions for startups and growing companies Year-end tax planning moves business owners should consider now Key business deductions you might be missing, from travel to home offices Special considerations for remote busine...

In this episode of The Liquidity Event, hosts AJ and Shane tackle year-end tax planning strategies (what you can still do!).   They break down: The importance of optimizing tax-advantaged accounts like 401(k)s, Roth IRAs, and HSAs The debate around charitable giving for young professionals Smart timing for exercising stock options and equity compensation Tax loss harvesting opportunities in volati...

In this episode of The Liquidity Event, hosts AJ and Shane demystify airline loyalty programs and credit card rewards. They break down: When airline status is (and isn't) worth pursuing The true value proposition of airport lounges and premium credit cards How to optimize your spending between airline miles and cash back rewards Inside tips on Delta's Diamond Medallion program and its changing ben...

As the election dust settles, we're discussing what a Trump-led administration will mean for tax policy and your finances in 2025 and beyond.   A lot of promises were made on the campaign trail. Join hosts AJ and Shane as they try to separate fact from fiction and forecast what Americans can expect:   -Implications for the Tax Cuts and Jobs Act (TCJA) -Impacts on Social Security taxation -What may...

In this episode of The Liquidity Event, hosts AJ and Shane talk donor advised funds & charitable giving. They discuss: Why Donor Advised Funds were created How they can be used a strategy to give more thoughtfully, particularly if you are not sure how exactly you want to give at year's end The dark side of DAFs - how the ultra wealthy have misused this strategy for their own benefit Give it a list...

In this episode of The Liquidity Event, hosts AJ and Ed dive into the annual workplace tradition we all love to hate: Open Enrollment Season. While logging into the HR portal and clicking through endless benefit options might feel like watching paint dry, making the wrong choices could leave your future self holding a much lighter wallet. Join them as they discuss: Health insurance (PPO vs HMO) Ho...

In Episode 122 of The Liquidity Event , Shane and AJ discuss the latest news surrounding OpenAI's funding and valuation, including a potential tender offer for employees. If you're an OpenAI employee, you'll want to pay close attention—serious tax planning could be on the horizon!   Shane and AJ also break down what a tender offer means, why timing is crucial for employees, and the importance of h...