In Episode 176 of The Liquidity Event, Shane is joined by Brooklyn Fi Senior Financial Planner Kody Sherlund to unpack a mix of personal finance headlines and real-world planning questions.

They kick things off with an IRS agent who moonlights as an NFL referee and what that says about modern "two-job" America. Then they break down what happens when a 529 plan is overfunded, whether insider stock purchases are actually a bullish signal, and why diversification still matters even when markets feel unpredictable.

The episode also covers Anthropic's reported $300B valuation and employee tender offer, including what to consider before selling private company shares. Finally, they tackle a Reddit question: can a couple earning $750K–$850K afford a $1.8M home in the NYC suburbs?

Key Time Stamps:

00:00 – Welcome + Episode Overview 00:34 – Shane & Kody intro 06:19 – IRS agent who's also an NFL referee 09:45 – What happens when you overfund a 529 plan 15:16 – Rethinking standard investment advice? 20:12 – Can you "beat" the market long term? 21:25 – Do insider stock purchases actually signal upside? 26:40 – Anthropic's $300B valuation & employee tender offer 27:47 – What to consider before selling private shares 32:22 – Can you afford a $1.8M home on $750K income?

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