Luck Isn’t Random—It’s Designed | Judd B. Kessler
The Art of Charm
How a Strong Plan B Lets You Go for Gold
Judd describes building outside options so you can take bigger risks pursuing top choices.
Why do some people always seem “lucky” while others miss out? In this episode, AJ and Johnny sit down with Wharton economics professor Judd Kessler, author of Lucky by Design, to reveal the hidden rules that govern life’s most important markets—from dating to job hunting to Taylor Swift tickets. These “choose me” markets don’t run on money alone; they run on signals, timing, and strategy.
You’ll learn why signaling interest often beats being perfect, how “settling for silver” can land you gold, and why gaming the system sometimes backfires. Judd breaks down strategies for college admissions, career opportunities, dating apps, and even Costco parking lots. Whether you’re chasing a dream job, trying to stand out in dating, or just fighting bots for concert tickets, this conversation shows you how to design your own luck.
What to Listen For
[00:01:04] What it means to be “lucky by design” and why hidden markets matter
[00:02:11] Taylor Swift tickets, hot restaurants, and how hidden rules decide who wins
[00:05:15] “Choose me” markets—jobs, schools, and dating—where the other side decides
[00:07:29] The two signals that matter most: competence and real interest
[00:10:22] Johnny’s story of breaking into bands through excitement and persistence
[00:13:24] Why idiosyncratic (weird) signals often work better than safe ones
[00:19:39] Costly signals—when to use them, and when they’re wasted
[00:21:41] The strategy of “settling for silver” to actually win
[00:27:05] When gaming the system works—and when it backfires
[00:29:53] Designing your inbox and attention like a market
[00:35:20] How a strong plan B lets you go for gold
[00:37:38] Costco parking lots as the perfect example of hidden strategy
[00:47:17] Hidden markets at home: sharing chores and mental load with equity
[00:55:05] Why ticket resale markets frustrate Judd—and how he wants to fix them
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