If you’ve spent any time on the streets or subways of New York City in the past decade, you’ve probably encountered the ads for Manhattan Mini Storage. The company is famous for its no-holds-barred billboards and subway posters, which sometimes poke fun at New Yorkers’ over-crowded lives, and other times skewer those who don’t hold unapologotically liberal political views. As chief branding officer of Edison Properties, the parent company of Manhattan Mini Storage, Archie Gottesman is the brains and wit behind those ads. She’s third-generation in the real-estate business and was eager to find a way to make the job of selling storage space more fun.

Gottesman later found herself provoking and entertaining readers with a different marketing effort. Despairing over the take-it-or-leave-it attitude many of her Jewish friends and...

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