In this episode of The Liquidity Event, AJ and Shane return from the Future Proof Wealth Management Festival with stories of Weezer, Bush, and the perils of leaving conferences too early. They dig into a New York Times article about using ChatGPT to tackle credit card debt, from spreadsheets to selling watermelons, and debate whether AI is democratizing financial advice or just creating quirky side hustles. The duo also unpack the harsh realities of sudden windfalls, from Powerball winners to stock concentration, and field a listener question about holding too much employer equity in retirement. Along the way, AJ champions late-night networking, Shane shouts out his accountability coach, and both remind us: diversify, diversify, diversify.

Timestamps (00:34) Intro – Ally Jane Ayers and Shane Mason kick off Episode 158. (01:18) Ally’s “radio host” voice and Shane’s zen brain. (02:12) Shoutout to Sherry Mason Real Estate in Cape Coral, FL. (03:22) Segues gone wrong and the Future Proof conference in Huntington Beach. (05:17) Conference quirks – Weezer, Third Eye Blind, Blues Traveler, and Bush. (07:02) Why AJ always leaves early and Shane always stays late. (09:13) Conference strategy – accountability coaches, goals, and nighttime networking. (12:04) “Your soulmate is at the afters” and why happy hours matter. (12:34) NYT article – using ChatGPT for financial advice and debt payoff. (14:37) Success stories – spreadsheets, budgeting, plasma donations, and almost selling feet pics. (16:06) Access and immediacy – why AI fills a gap financial advisors can’t. (17:38) Reflections on Brooklyn FI’s early late-night client meetings. (18:46) Lottery winners and hard lessons ahead of the $1.8B Powerball. (20:50) Quick Picks vs. lucky numbers – let the computer decide. (22:40) AJ’s advice for sudden money windfalls – spend 1% and get a care team. (23:59) Shane’s fantasy purchases: boat or flashy watch. (24:41) Building your financial “care team” for long-term stability. (25:35) Listener question – is 50% in one stock too much? (27:23) The risks of concentration and why diversification matters. (28:34) AJ’s plan: sell 25% now, the rest over three years, or gift it. (30:20) Imagining being the kids of parents who “don’t care” about millions. (30:41) Closing – diversify, send us your financial questions, or just post them on Reddit.

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