In this episode of The Liquidity Event, AJ and Shane kick off the new year by unpacking the trillion-dollar AI ecosystem, including NVIDIA's soaring valuation, OpenAI's circular funding relationships, and the growing debate over whether today's infrastructure boom is progress or a fragile bubble waiting to pop. They explore the real costs of AI, from massive data centers to job displacement, and what happens if one key player breaks the chain.

The conversation then turns to SpaceX's active tender offer and what employees need to understand right now, including tax timing, ISO exercises, and planning across multiple tax years ahead of a potential 2026 IPO. AJ and Shane also touch on New York residency audits, why leaving high-tax states is harder than it looks, and the practical realities that trip people up. The episode wraps with Gemini updates, market optimism for 2026, and a characteristically tangential, mid-December dose of silliness.

(00:00) Welcome, holiday timing, and recording the New Year's episode early
(02:00) California pride, high taxes, and why people still stay
(05:00) How AJ and Shane choose podcast topics (and why tangents happen)
(08:30) Philly cheesesteaks, grills, and peak mid-December chaos
(10:30) NVIDIA, OpenAI, and the trillion-dollar AI money machine
(13:30) Circular deals, AI bubbles, and being "right no matter what"
(16:30) Infrastructure scale, data centers, and the real costs of AI
(19:30) Jobs, automation fears, and what AI actually replaces
(22:30) SpaceX tender offers, ISO exercises, and year-end tax strategy
(29:00) Gemini updates, 2026 planning optimism, and wrapping the silliness

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Today we're sharing a special rebroadcast of John Owens's appearance on The Long Term Investor with Peter Lazaroff. In this episode, John breaks down a clear, practical year-end playbook for equity compensation, including RSUs, ISOs/NQSOs, and ESPPs, and highlights the tax traps and planning opportunities clients should keep on their radar.

You'll hear John and Peter discuss:

• How to prioritize equity comp decisions at year-end
• Common RSU withholding pitfalls that lead to April surprises
• ISO/AMT basics and why late-year exercises can be risky
• Building a rules-based selling strategy to manage concentration
• When donor-advised funds and multi-year planning make sense

This episode originally aired on The Long Term Investor and is shared here with permission. To explore more of Peter's work, visit The Long Term Investor.

Key Timestamps:

• (00:00) Introduction
• (03:15) A hard-won lesson: when AMT grows larger than your stock (and what to do next)
• (04:21) Don't start equity planning on December 15 (really) (05:19) First move: build an inventory and triage the quick wins
• (08:18) AMT 101 for ISO holders: the "parallel" tax you don't want to pay
• (10:47) RSUs: why 22% withholding often sets up an April tax bill
• (12:24) ESPPs: capture the discount, control concentration (14:55) Designing a rules-based sell plan to unwind concentration risk
• (18:11) The base rates on single stocks: why a diversification plan matters more than a "feel" (20:42) 10b5-1 plans: automate good behavior and expand your ability to sell
• (23:31) Charitable giving with concentrated stock: donor-advised funds and timing across 2025/2026
• (26:11) Family gifting: UTMAs, kiddie tax, step-up in basis, and multi-generational choice
• (27:28) The year-end document checklist most people miss
• (29:17) When to hire help (and when not to) (31:19) Biggest year-end mistakes to avoid

🔔 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 dig into the trillion-dollar AI ecosystem, from NVIDIA's massive market cap to the circular funding loops tying together OpenAI, Microsoft, and the rest of the AI stack. They debate whether today's infrastructure buildout is necessary progress or a replay of past bubbles, and what happens if one key player breaks the chain.

The conversation then shifts to SpaceX's active tender offer, what employees need to know right now, and why timing across tax years can be life-changing for equity holders. Along the way, AJ and Shane explore high-tax residency decisions, year-end planning pressures, and the real-world implications of building massive data centers, including job creation, community development, and energy costs. The episode wraps with behind-the-scenes updates on Gemini, market optimism for 2026, and a refreshingly silly mid-December detour or two.

(00:00) Welcome, holiday vibes, and guest appearance from Charlie Mason
(03:00) California pride, taxes, and why people still stay
(05:00) How AJ and Shane pick articles (and why tangents win)
(08:30) Philly cheesesteaks, grills, and peak mid-December chaos
(10:30) NVIDIA, OpenAI, and the trillion-dollar AI money loop
(13:30) Circular deals, AI bubbles, and "being right no matter what"
(16:30) Infrastructure scale: AI vs. telecom vs. AWS
(19:30) Data centers, job displacement, and AI's real costs
(22:00) SpaceX tender offers, liquidity timing, and tax strategy
(29:00) Gemini updates, 2026 optimism, and wrapping the silliness

🔔 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