Tax Day Confessions, The Upper Middle Class Trap, and the SpaceX IPO — Episode 185

Apr 16, 2026

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