Risky Business: Inside the Offices of 8 Top NYC Entrepreneurs

Marni Golden
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Risky Business: Inside the Offices of 8 Top NYC Entrepreneurs
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Judging by the press around small businesses and entrepreneurship, it may seem at times like we’re living in a world where creating your own business has become more common than standing in line at a job fair.
The notion of making a business out of a simple, innovative idea is something that many young people flirt with at some stage in their career, but having the diligence, patience and, well, cajones to make an idea actually come to life and prosper is far less common. Why do so few take the leap? Well, the proposition involves a great deal of risk—so much so that it can be argued that only those with a passion for a good gamble should venture into the territory. Of course, those that really make a mark have the opportunity to become rock stars—think Mark Zuckerberg and Jeff Bezos—and who wouldn’t want that?
So what, exactly, does it take to “make it” in the competitive, over-crowded, luxury and lifestyle entrepreneurial space in particular? We decided to go straight to the sources and visit eight of our favorite entrepreneurs in New York City—from the gentlemen behind Highlands Restaurant Group to the co-founders of Edition01, an e-commerce site that collaborates with designers on limited edition collections.
Here, they give us an all-access pass into their offices and share insights into the make-it or break-it world of creating one’s own business. These brave souls share how it feels to put it all on the line and become your own boss—and why they’ll never look back.
Photography by Nick Onken
Hair & Makeup by Alice An
Post Production by Rolando Robinson

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What, exactly, does it take to “make it” in the competitive, over-crowded, luxury and lifestyle entrepreneurial space? We decided to go straight to the sources and visit eight of our favorite entrepreneurs in New York City.

Photo: Nick Onken/

Brian McGrory and Donal Brophy of Highlands Restaurant Group, shot at WHITEHALL Bar + Kitchen in the charming West Village.

Photo: Nick Onken/

Coming from humble beginnings as a dish washer at a local Italian restaurant outside Dublin, Brophy explains, "Brian and I decided that New York needed a cool downtown Scottish pub that represented the contemporary side of the Scottish experience." He continues, "I was a cater-waiter too, but I'd always end up joining the party and dancing with the old ladies—not a huge surprise [that] I got fired."

Photo: Nick Onken/

The fun-loving duo stress the importance of instilling a laid-back work environment and bringing out their staff's personalities. Investing in chic uniforms for their servers was as essential as getting to know them. "We keep the lines of communication open at all times to best understand them. The odd night out doesn't hurt either," Brophy adds.

Photo: Nick Onken/

Ruth Zukerman, co-founder of Flywheel Sports, an innovative indoor cycling chain, pictured at her Flatiron studio.

Photo: Nick Onken/

Many cycling newbies are intimidated to take their first stab at a Flywheel class, but Zukerman makes sure to put her spinners at ease. "It's important to me to set a tone of comfort and approachability," she states. "The best piece of advice I've ever received is to know your customer and treat them like gold."

Photo: Nick Onken/

"I opened my first boutique indoor cycling studio in 2006, and when I saw that 80 percent of my previous following gave up their high-end gym memberships to ride with me in much more modest surroundings, I knew I was onto something," notes Zukerman. "Four years later, I took the experience to new levels and opened Flywheel."

Photo: Nick Onken/

Alison Brod, owner of Alison Brod PR, a beauty, fashion, celebrity, entertainment, and lifestyle public relations and marketing agency.

Photo: Nick Onken/

There's no denying that Brod is a girl's girl. After all, her office space is littered with pink, Pucci, and pretty girls, with no shortage of candy readily available. She admits, "I believe in pink. I believe in lipstick."

Photo: Nick Onken/

Despite the frilly exterior, this PR power player is a force to be reckoned with, representing an impressive slew of mega-retailers, fashion labels, cosmetic brands and celebrity influencers including Godiva and L'Oreal. The key to her success? "The client is always right," Brod firmly states. "Having a consulting business of my own, I find it's the most difficult tenet to uphold."

Photo: Nick Onken/

Cary Estes Leitzes, founder of Leitzes & Co, an agency that unites art, fashion, and commerce. To her right, a collection of wood chip chairs by Chris Rucker of Rucker Corp.

Photo: Nick Onken/

Formerly the Photo Director at Harper's Bazaar, Leitzes started her own creative marketing company, LEITZES&CO, which pairs contemporary artists and designers with iconic brands. Recent stand-out successes include Rob Pruitt's collection for Jimmy Choo (pictured above) and Assume Vivid Astro Focus' creation of Lady Gaga's Workshop for Barney's New York.

Leitzes knew she was onto something when she attended MOCA's annual gala honoring Takashi Murakami in 2007, in collaboration with Kanye West and Louis Vuitton. "I was fascinated by this blurring of boundaries between creative disciplines," adds Leitzes. "That was my tipping point."

Photo: Nick Onken/

Ben Lerer, co-founder and CEO of Thrillist Media Group, JackThreads and Thrilllist, a leading newsletter and e-commerce site for men.

Photo: Nick Onken/

Thrillist, a leading men’s lifestyle brand with over three million subscribers across 20 editions, further expanded into e-commerce by acquiring members-only shopping club JackThreads.com in 2010. Lerer, who adheres to (and embodies) a work-hard-play-hard philosophy, has his priorities firmly set. "We invest a great deal into our bar. We never splurge on fancy offices for senior employees," say Lerer. "Generally, everyone has the same desk, same amount of space."

Photo: Nick Onken/

Even as a teen, Lerer had the entrepreneurial bug. "I sold amazing fake-IDs. They were scannable. It was a huge success," he proudly admits. He knew he wanted to have a job that he didn't dread waking up for. In regards to starting Thrillist, Lerer wryly states, "I think it was a combination of wanting a job that didn't give you that Sunday night pit-in-your-stomach slash I-don't-want-to-go-to-work feeling. That, and the fact that we actually had a really god idea."

Photo: Nick Onken/

Estefania Lacayo and Jessica Wilpon Kamel, co-founders of Edition01, an e-commerce site that features exclusive collaborations with the world's top luxury designers.

Photo: Nick Onken/

Lacayo and Kamel set out to create a unique online destination where customers could view and purchase limited-edition luxury products that were carefully curated and sold exclusively on the site. The duo hand pick every item that will be sold on the site, making sure each item aligns with the brand. Kamel explains, "The best advice I received was from Susan Feldman, the founder of One Kings Lane. She told me that good products sell, so make sure you love every product on your site." She adds: "It's something I think about everyday."

Photo: Nick Onken/

Eric Villency, Principal of Villency Design Group, a design firm that works on projects across a broad spectrum of disciplines.

Photo: Nick Onken/

The Villency Design Group conceives and executes fully-integrated projects across fashion, industrial design, product development, fabrication, fulfillment, and brand advisory. Pictured above are recent collaborations with Organic Avenue, Target, and The Ritz Carlton.

Growing up around his family's furniture business, Villency was hardwired for design and entrepreneurship. "I would run around the upholstery shop wildy waiving a nail gun in the air," Villency says with a smile. "It was impossible not to fall instantly in love with design and manufacturing."

Photo: Nick Onken/

Jennifer Fleiss, President and co-founder of Rent the Runway, an online designer dress rental destination.

Photo: Nick Onken/

Fleiss knew she wanted to be an entrepreneur early on—starting a lemonade stand in grade school—and met her RTR co-founder, Jennifer Hyman, at Harvard Business School. Fleiss explains, "We started the business with the mission to democratize luxury and give women everywhere access to designer dresses and accessories for all of the special occasions in their lives, especially when the economic downturn had given way to a recessionista culture that welcomed such an idea."

Photo: Nick Onken/

"Jenn and I had a rule from the very beginning never to write a business plan. My two mentors stressed to me the importance of testing out an idea on the ground rather than hypothesizing about how a concept will play out when executed," recalls Fleiss.

"Staying scrappy is one of our most valued principles so it’s vital to us that Rent the Runway maintains its startup mentality. Jenn and I both sit amidst our entire staff—we don’t believe in walls."

Photo: Nick Onken/

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