It's Tax Day, and Shane and Kody are in their element. In Episode 185 of The Liquidity Event, they kick off with a behind-the-scenes look at what tax season actually looks like for financial planners, from correcting misclassified stock options to saving clients tens of thousands of dollars that TurboTax Live told them they owed.

They also dig into how Intuit used large language models to compress 900 pages of new tax legislation into weeks of implementation instead of months, and whether a viral Reddit post claiming Claude Code can replace TurboTax entirely is onto something or a cautionary tale.

Then it's onto the Wall Street Journal's finding that the upper middle class has tripled since 1979, why income alone doesn't tell the whole story, and what a $2 trillion SpaceX IPO valuation actually means for investors with private stock heading into a potentially wild summer debut.

Topics covered:

• Tax season war stories and common filing mistakes with equity compensation
• How Intuit used AI to implement 900 pages of new tax legislation in weeks
• The upper middle class defined: who qualifies and why income alone isn't enough
• Cost of living, housing affordability, and purchasing power by geography
• SpaceX IPO outlook, valuation history, and what private shareholders should consider
• Can Claude Code actually do your taxes? A Reddit experiment reviewed

Timestamps:

• 00:00 Intro and Tax Day with Kody
• 01:19 What tax season actually looks like for financial planners
• 03:52 TurboTax Live told my friend he owed $50k more than he did
• 05:45 Shoutout to AJ on digital detox and today's episode preview
• 08:31 How Intuit used AI to process 900 pages of new tax law in weeks
• 13:33 More Americans are breaking into the upper middle class
• 15:17 Why income alone doesn't define middle class and what's missing from the data
• 22:58 SpaceX eyes a $2 trillion IPO valuation amid C-suite shakeups
• 28:29 SpaceX valuation history: from $10B in 2015 to $1.75T today
• 30:59 Reddit: Claude just did my taxes and I'm shorting Intuit $100k

🔔 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

Can you keep your 401k when you move abroad? What happens to your Roth IRA if you live in France? And is a baby registry company really worth watching as an IPO?

In Episode 184 of The Liquidity Event, Shane and AJ tackle one of the most common questions they get from American expats and dual citizens: how do you build a retirement plan when you're living abroad, paying taxes in another country, and still filing as a US person? Shane breaks down how income tax treaties work, what expats need to know about 401k and Roth IRA distributions overseas, the real cost of moving money between countries, and why accidental Americans can face some surprising IRS consequences.

Then they dig into Babylist, the baby registry platform approaching $1 billion in sales and eyeing a 2027 IPO. It's been profitable for eight straight years, raised only $40 million in outside capital, and sat out the 2021 IPO rush entirely. AJ and Shane break down why the asset-light model works, what it has in common with Etsy, and why babies aren't going anywhere.

Topics covered:

• Expat retirement planning and 401k rules for Americans living abroad
• Dual citizenship tax strategy and income tax treaties
• Roth IRA distributions for US citizens overseas
• Currency hedging and moving money internationally
• Babylist IPO outlook and what makes it different
• Financial planning for Americans with dual citizenship in Europe

Timestamps:

• 00:00 Intro and AJ's desk flooding incident
• 01:55 Iran ceasefire reaction and NYC nuclear anxiety
• 07:45 The Brooklyn of New Delhi and global culture
• 12:20 Listener question: retirement planning as an American abroad
• 13:58 How income tax treaties protect expat 401k holders
• 18:24 Moving money internationally and currency hedging
• 21:17 Why financial planning abroad is uniquely complex
• 24:28 Babylist approaches $1B in sales and eyes 2027 IPO

🔔 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

Q1 started strong and then the final stretch changed everything.

In Episode 183 of The Liquidity Event, AJ and John break down what actually happened in the markets this quarter, from oil's sharp rise and renewed inflation concerns to why both stocks and bonds felt pressure. They walk through how global conflict impacts commodities, rate cut expectations, and what investors should really be paying attention to as we move into Q2.

The conversation also covers the growing world of advanced tax strategies for high net worth investors, including direct indexing, 351 exchanges, and exchange funds. These tools are becoming more accessible, but they are not one size fits all. AJ and John explain how they work, who they are actually for, and why complexity does not always mean better outcomes.

They also unpack a headline making the rounds about a major league baseball player suing his parents over alleged financial mismanagement, and what it reveals about family dynamics and sudden wealth. Finally, they explore the new Bitcoin backed mortgage structure entering the market and whether it is financial innovation or leverage risk in disguise.

2:05 – Q1 Market Recap and the Oil Spike
4:10 – Inflation Concerns and Shifting Rate Cut Expectations
6:30 – How Gas Prices Hit Everyday Investors
9:00 – MLB Player Sues Parents Over Millions
12:15 – NIL Deals and Young Athletes Managing Wealth
16:05 – The One Trillion Dollar Industry of Tax Reduction
18:40 – Direct Indexing and When It Makes Sense
21:30 – 351 Exchanges and Exchange Funds Explained
25:10 – Tax Aware Long Short Strategies and the Risks
29:45 – Bitcoin Backed Mortgages and Leverage Concerns

🔔 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