John brings on Wharton economist Judd B. Kessler to unpack why outcomes that look like luck are usually the product of hidden market designs. Kessler explains the three E’s—equity, efficiency, and ease—and why designers must make those tradeoffs explicit. He shows how to win in choose-me markets (jobs, dating, college admissions) by signaling clearly and sometimes prioritizing early commitment (e.g., early decision). In high-scarcity races (restaurant reservations, tickets), he argues for “settling for silver”—acting on a strong second choice first—to beat the crowd.

The conversation gets tactical: how to stand out when AI drafts cover letters, why human connection cuts through noise, how public-school lotteries and clearinghouses really work, and how to make household labor fair using envy-freeness and full-stack task ownership (Conception-Planning-Execution). Listeners leave with a repeatable loop: see the market, learn the rules, choose the strategy—and start designing luck on purpose. 

Catch more of Judd Kessler: https://bepp.wharton.upenn.edu/profile/juddk/

Click here for the full shownotes!

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