In this episode of The Liquidity Event, Shane (aka Delta Juan Enjoyer) joins Ally to unpack Taylor Swift and Travis Kelsey’s engagement and why it’s a perfect case study in prenups. They explore the promise (and hype) of an AI-powered stethoscope, debate private equity’s push into 401(k)s, and tackle a listener question about selling real estate with a $600K tax bill. Along the way, AJ shares a personal story about her parents’ divorce, Shane muses on Blank Street Coffee, and the duo circle back (again and again) to the question of what truly makes for financial happiness.

(00:34) Intro – Ally Jane Ayers and Shane Mason kick off Episode 157.

(01:09) Austin’s Juan in a Million & Private Equity “-ification” joke.

(01:38) Episode topics preview – Taylor & Travis engagement, AI stethoscope, ETFs vs. stocks

(03:22) Taylor Swift & Travis Kelsey engagement discussion

(06:23) What prenups actually cover & why they matter

(13:03) New AI-powered stethoscope & medical tech

(17:03) Is it really AI, or just data comparison?

(20:22) Private equity is trying to disrupt 401(k)s

(23:40) Why this threatens retirement savings & financial security

(27:16) Example: Blank Street Coffee & private equity “ruining” businesses

(28:58) Listener question – real estate sale with $600K tax bill

(31:05) Advice: simplicity vs. 1031 exchange

(33:39) Risks of relying only on real estate in retirement

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