How This 28-Year-Old Earned the Title ‘New York’s Best Dressed Broker’

Born and raised in the Bronx (a kindergarten student of J.Lo’s mom), Kevin Benejam honed his eclectic skills while splitting time between the homes of his mother and father—in the Bronx and Westchester, respectively. “It gave me a lot of the street smarts that I use now in business, which gives me an advantage,” he says over the phone. He’s in a busy shop in between meetings in New York City, where he is continually hustling to build his businesses—a digital marketing agency called Entitled Ventures, a YouTube series called On Trend and a burgeoning Instagram account. We’re tapping Benejam in partnership with Kenneth Cole’s "What Moves You" campaign, an initiative that highlights movers and shakers in style, business, culture and sports.

As a kid, Benejam—also known as KB—idolized baseball legend Derek Jeter and basketball star Michael Jordan, two sports kings with supreme business acumen and strategic personal branding. “I didn’t see a lot of black or Hispanic entrepreneurs rising up, so these were very inspiring people for me. If they could do it, then I could totally do it too.” Attending Catholic school, Benejam was the stylish rebel, citing frequent detentions for breaking the dress code in the most unique ways. “I always had a spin on fashion, no matter what.”

Today, he is well on his way to making an imprint on the men’s fashion scene. After a quick scroll through his website, you quickly realize that Benejam is a man of many trades. After graduating from college, he morphed from successfully selling real estate to styling his property buyers and updating their wardrobes—he was even touted as New York’s best-dressed broker. From there, he took his personal style to social media, capturing his fits for an organic following that has grown to more than 46,000 people. It was at this point that Benejam realized he could turn his hobby into a real business.

About a year and a half ago, Benejam launched his own web series called On Trend, a long-form series that lives on YouTube and highlights other city-dwelling men. In the first episode, Benejam channels his inner Ryan Seacrest (another childhood hero) to acutely interview Gerard Adams, founder of the digital publication Elite Daily, on how he built his business.

Benejam is also a social media consultant for fashion brands through a company called Entitled Ventures, which he founded gradually over the years. “We help across the board with content, digital marketing, social media, Instagram, Facebook and events.” He uses his styling skills to amp up photo shoots for his clients as well as his personal brand.

To balance the innumerable tasks that cross his plate, Benejam has a few tactics for supreme time management, as “time is the most valuable resource we have,” he says. He relies on comfortable footwear, like Kenneth Cole's Futurepod Cap Toe Dress Oxford with Techni-Cole in black, to propel him through the day. With so many tasks to juggle, there's no time for unwanted blisters. The Rebound System IP cushions like a sneaker but packs a sophisticated punch with its oxford upper. 

He has hour limits on all social platforms instituted on his phone, only answers emails at specific hours of the day (namely 9 a.m. and 5 p.m.) and ignores text messages unless they’re pertinent. And, surprisingly, he schedules blocks of time for fun activities. “When someone is really ambitious and they want to go for it, they can try to work 20 hours a day, but you get really tired like that,” he explains. Ultimately, every day in Benejam’s life is different. As a full-time content creator, he’s scheduling photo shoots, coordinating with brands, going to the gym, utilizing his office at a local WeWork space, journaling and reading business books or autobiographies.

I have hour limits on all social platforms instituted on my phone, only answer emails at specific hours of the day (namely 9 a.m. and 5 p.m.) and ignore text messages unless they’re pertinent.

- Kevin Benejam, Style Maverick

We asked Benejam—in the face of all this—how he manages to stay motivated to persist. “I don’t have kids, but eventually I do want them and I want to create a long-lasting legacy for myself and for them,” he says sincerely. “Hopefully, I can inspire people to do what they really want to do in life. I know a lot of people are stuck right now, and I want to inspire them to get to the next level. That’s what really motivates me.”