How This Millennial Lawyer Built a Successful Hamptons Media Company as a Side Hustle

At first glance, Rex Chatterjee isn’t the person you picture when you think “Hamptons.” Dressed in his signature grey v-neck t-shirt, with faded baggy blue jeans hiding the tops of a pair once-white Converse, Chatterjee looks a far cry from the “Brooks Brothers & Boat Shoes” theme we generally associate with Long Island’s East End. A glance at his wrist, featuring a limited edition Rolex Daytona, however, betrays the fact that his dressed-down appearance is but a façade. A ruse, designed to disguise the fact that he does, in fact, fit in to the luxury-based, highly curated “out east” scene.

But what drove this lawyer, with degrees from Cornell and Columbia Law School, to start up journalism venture Dune Road Lifestyle as a side line to his legal career? In his own words, Chatterjee says, “I’ve always been a creative person, but coming from an Asian immigrant family and being first-generation American, there was a lot of pressure on me to have one of ‘those’ careers, you know, doctor, lawyer, or engineer. So, I went the law route because writing had always come fairly naturally to me, and throughout the course of my education, I always had little side projects going on. This one is just sort of the culmination of all that.”

His past creative exploits began soon after his departure to college. In his first semester, Chatterjee became a radio DJ and on-air personality at 93.5 WVBR FM in Ithaca, New York. Of the experience, he notes, “I was drawn to radio because of my love for music, really. And I’d had experience working with studio boards, albeit virtually, from messing around on software like Reason while in high school. So, passing my air-check was relatively easy and within weeks of joining the station, I was playing music live on air. The format was classic rock, which I eventually grew to love, but the main thing for me was that, for the first time, I was doing something both creative and real: going out to a real audience, getting request calls from real people, the whole bit.”

Radio soon gave way to an interest in live music, however, and less than a year later, the one-time Ithaca radio jock became a nightlife promoter and millennium-era club kid in New York City. “I had a group of friends, some up with me at Cornell, others down in the city at NYU, and we’d promote via our social networks at various clubs downtown. I remember one of my first nights on the scene, we were at Plumm, which had just opened. Samantha Ronson was DJing, and that’s where the connection was made for me, from producing beats in high school, to being on-air in college, to the next step for me, which was learning to become a DJ. It’s just something I knew was a fit, but it’d be a while before I was able to really circle back to it.”

And that’s because Chatterjee still had college grades to deal with. With his sights set on the top echelon of US law schools, he knew he had only a limited number of semesters left to earn high marks—not to mention prepare for and take the LSAT entrance exam—before submitting his applications. With admission rates for his top choices ranging in the single-digits, the legal-aspirant knew he had his work cut out for him. “I basically became a shut-in, put my head down, and went to work. I posted 4.0s in my final two semesters, did pretty okay on the LSAT, and in the end, it all worked out.” Graduating a semester early from Cornell, Chatterjee received his acceptance letter to Columbia University’s School of Law, and was now finally, for a brief moment in time, free to pursue his creative endeavors.

“I spent what would’ve been my final semester of college living up in Ithaca. I worked two jobs, as an LSAT tutor and as the door guy at a local bar, and pretty quickly was able to save up enough to buy a DJ controller and a decent set of headphones. From that point on, it was difficult to tear me away from the decks, and I was constantly thinking about mixes, working on transitions, and just generally gaining experience with DJing, doing a few sets here and there at friends’ parties. It was all pretty small time, but it was a start, and all I needed.”

That start would soon pave the way for bigger and brighter endeavors, as with the start of his law school career came Chatterjee’s first foray into the world of New York City DJing. “Being that I’d spent so much time in the NYC nightlife scene, I became known in school now, down back in the city, as someone who was full of good ideas for what to do on a Saturday night,” he recalls. “I loved being a resource to people, but I felt like I owed them more than just whatever happened to be top of mind at the moment they called or texted. So, I booted up Notepad and started coding.” Soon after, Chatterjee would launch “The Rex List,” a now-defunct blog cataloguing his in-depth knowledge of bars and clubs downtown. Going beyond what one might find on other websites, Chatterjee shared his personal insights and connections with what he knew would be a close circle of readers and followers. For example, “A lot of websites might have mentioned ‘R Bar’ as a great spot to check out in SoHo. Not many, though, would have told you that the door guys on-shift on Friday and Saturday nights were called Petey and Gene, and if you told them you knew me, you could cut the line. Just remember to tip them well on your way out.”

In tandem with his brand new website, Chatterjee began working with his promoter connections to set up private parties for his law school friends and their networks, who wanted the feel of dancing to a DJ’s beats in a club, but without the $1000 / bottle price tag that almost always came along with it. Doing everything from arranging venues to dropping beats, the budding entrepreneur quickly made a name for himself around the city, as word of his secretive nightlife events spread through the city’s mid-20s demographic like wildfire.

Work, however, always has a way of ruining fun, and the same came true for Chatterjee and his cohort as they graduated from law school in 2011. Off went the skinny jeans, on went the suit, and to work he went. And after holding roles in consulting, banking, and law practice, Chatterjee finally found himself having the time to reengage on a creative endeavor. “It was after I’d left a position as corporate counsel and before I’d started my private practice that I thought to work on something creative, just to get back in touch with that sense of inspiration.” The product of this exploration was Dune Road Lifestyle, a media company launched as a Hamptons Guide website back in 2018. “Originally, when the site was just the Guide, it looked and felt a lot like ‘The Rex List,’” he notes. “I’d had a lot of the same experience out in the Hamptons as I did in the city, going out all over and making connections with the owners of various businesses. I’d done a real combing of the scene, and was able to quickly pick out the handful of spots that I could recommend to someone unconditionally. Those places formed the core of the first ‘Dune Road Lifestyle Hamptons Guide.’”

Starting with only a few restaurants and bars, the “Guide,” as it has come to be known among its fans, now includes over one hundred businesses from Westhampton to Montauk. The Guide’s scope of coverage has expanded as well, now also showcasing coffee shops, hotels, gyms, spas and boutiques.

Soon after going live with the Guide, the site launched a blog called “What’s Hot Out East,” featuring Hamptons events, pop-ups, restaurant openings, parties, and more.

More recently, Dune Road Lifestyle has launched “The Out East Vibes Podcast,” a weekly show dedicated to showcasing the voices of celebrities, VIPs, influencers, and notable east end locals discussing topics from global politics to their most comical Hamptons moments.

When asked how he does it, and how he even has the time to with his professional obligations to his law practice, Chatterjee Legal, and his role with consulting firm Titan Grey, he cracks a wry grin and responds, “Well, you could say, I’ve been doing this my whole life.” He tempts not adding more, before continuing, “The Hamptons Guide? It’s the same workflow as The Rex List. I’ve been at this for a decade, we’ve just switched the scenery.” At the core of the guide is its one guiding threshold. If Chatterjee can’t personally, and unconditionally, recommend a place, it isn’t appearing on the Guide. No exceptions. “We’re not trying to be one of those broad-based sites over here; we’re not trying to boil the ocean,” he quips. “We take our time, we do our homework, and we keep it brief. It’s not a ton of writing work; it just requires an extreme attention to detail.”

With respect to the podcast, his position is a little more relaxed. “This one was newer territory for me,” he notes, offering that “it wasn’t one-to-one with anything I’d done before.” His radio experience, however, did factor in. “I’m comfortable in the studio, and I have real broadcast experience, so that definitely made it easier to get started.” When it comes to conducting the interviews, though, it’s a definite shift from his day-to-day. “No one’s getting cross-examined here, so that whole mode of thinking needed to just go out the window,” he says. “The podcast is about celebrating the good times, focusing on the positive, and it’s a great refresher from some of my work in the law and in corporate risk.” With the use of pre-formatted editing tools and an easy-to-manage platform, Chatterjee can get an episode of The Out East Vibes Podcast recorded, cut and published in a matter of hours.

And, never one to let a formative experience fall by the wayside, Chatterjee has even found a way to keep DJing while managing all of his new endeavors. Working under the brand name “Out East Beats,” Chatterjee curates playlists, posts mixes and DJs select events and private parties on behalf of Dune Road Lifestyle. Of it, he says, “music is a big part of life in the Hamptons, and we couldn’t just ignore it.”

Now staffed with a team of other professionals, Dune Road Lifestyle is poised to make its mark this Summer 2020. If you’re trying to make the most of your summer in the Hamptons, theirs is one site you can’t afford to miss.

For more exclusive content, you can find Dune Road Lifestyle on Instagram at @duneroadlifestyle.