While the aptly named Upper West Side boutique West NYC has only been open since 2007, its owner, Lester Wasserman, is part of a family that has four generations in the shoe business. His grandparents opened their first store in the Bronx after emigrating from Israel, and later relocated to Manhattan, where the family business remains to this day.

But while the Wasserman family business boasted some high quality shoes, their inventory did not feature a lot (or any) of the fashion forward footwear and athletic shoes that were becoming increasingly popular as Lester grew up. So, when he joined the business, that was the first thing he addressed. “It’s always tough to convince people who have been doing things a certain way that there’s another way to do them,” he says. “But, luckily for me, I have a pretty receptive family. …Either that, or I’m a really good salesperson,” he adds, with a sly wink.

Lester’s knowledge and persuasion helped his family’s shop adapt to include more modern and popular kicks. But this decision didn’t just stem from his business savvy, but also from the fact that Lester himself is a straight-up sneakerhead. With a closet full of kicks, many of which he’s never even worn, Lester--like most seasoned collectors--has watched his tastes change as he’s grown. “Now I only buy stuff I like,” he says. “I’m a pretty serious runner, so my focus is on running shoes these days.” He pauses, then adds—again with a smile—“stuff that nobody here cares about.”

For more on Lester Wasserman’s thoughts on footwear, including the athlete who inspired him to start loving kicks (hint: it’s not MJ, or Bron Bron, or even an NBA player), be sure to check out the latest episode of FILA’s of Rise of the Independents above.