My first job was at Sam’s Fine Men’s Clothing in Livingston, N.J. Family-owned, Sam’s was and still is the go-to neighborhood store for men’s and boy’s clothing. I worked weekends, summers and school breaks as a way to support my nonpaying New York City internships and my desire for financial independence.

As a 17-year-old high school senior, I clearly couldn’t sell expensive men’s suits to titans of industry, so I was relegated to the boy’s department. It was here that I learned to tailor my message to different customers. Thirteen-year-old boys don’t come in to buy clothes alone—it’s usually an entourage (mother, grandmother, often a sibling). I quickly learned that I had to make everyone happy. I had to make sure the kid thought his clothes were cool. Getting his size right on the first try was key. A second round of trying on pants could kill a sale. For the mother, I had to quickly assess whether she wanted classic or something more contemporary and fashion forward (Italian sharkskin—yes, it was the Eighties). Lastly, I had to assure the grandmother—who was usually footing the bill—of the high-quality fabrics and reputable manufacturer.

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