In this episode, AJ and Shane break down why every VC-backed IPO in the past 12 months has been a “down round” and what that means for your equity. Then they tackle a juicy Reddit question from a 32-year-old tech worker vesting $400,000 per month (!) who's considering walking away from $5 million in future equity.

Key Timestamps:

(0:00) Introductions and summer traipsing vs. gallivanting exploration

(4:40) IPO “down rounds” explained

(8:45) The economics behind down rounds: cheap COVID money meets high interest rates

(12:30) Circle and Chime IPO examples - companies going public at lower valuations

(15:45) Why tender offers might be your best bet in this market

(17:45) Reddit question: "Is $10 million enough to retire on?"

(21:00) The $400K per month dilemma - stay for more money or quit while ahead?

(26:30) Team Quit vs. Team Stay - Opposing views on leaving $5 million on the table

(29:30) What being really rich buys you (spoiler: private jets)

The Debate: AJ argues for quitting: Take the money, buy the house, live the good life before kids arrive. Shane argues for staying: You're making $3,000 per hour. Don't walk away from generational wealth.

Who's right? Let us know in the comments.

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