“I think this country should be operating the way it used to be a long time ago which was if you take a risk, then you’re going to be punished if it doesn’t work out,” said Kiliaen Van Rensselaer over drinks Saturday night at the Hotel Plaza Athenee hotel on East 64th Street.
Mr. Van Rensselaer knows something about how the country operated a long time ago: his great-, great-, many-times-over-great-grandfather of the same name was co-founder of the Dutch West India Company and presided over Rensselaerswyck, a swath of roughly 1,200 square miles of present-day upstate New York. The first Lord of the Manor, as he was called, expired in 1643, but the accomplishments of his descendents—count one general in the Revolutionary War, numerous congressmen, a couple lieutenant governors—assured the Van Rensselaer name longevity.
Now 38, the current Kiliaen Van Rensselaer grew up in Westport, Conn., and moved to Manhattan after college.
“As a family, we’ve always been very private,” he said. He was wearing a white collared shirt, navy sweater, jeans and loafers. His ancestry was reflected in his face—high cheekbones, square chin, a nose you could hang a top hat on—as well as his confident manner. He’d brought along his girlfriend, Monique Menniken, a former professional tennis player from Germany, who now makes her living as a model.
“I’ve read a lot about my first great-grandfather who had my name,” said Mr. Van Rensselaer, who as an American history major at Trinity College had the unique experience of being able to study the evolution of his family tree. “He was born in 1580 in Amsterdam and became part of the Dutch West India Company, and they became involved in putting a lot of capital at risk, because they sent a lot of ships and colonial prospects and animals and plants and things over to try to create a set of plantations and successful colonies. I’m a big free-market capitalist, so I understand the kind of risk associated with just sending a ship off where any number of things can happen to it. And if it made it across, obviously it was very difficult to survive. So the fact that it turned into something, and it was one of the only really successful colonies that was privately established, is kind of cool to think about.”
Risk and reward. It’s the American way. Until it wasn’t: Mr. Van Rensselaer is against the government bailout of the financial industry.
“Maybe it starts with the original heritage of Kiliaen Van Rensselaer the first, who took a huge risk to establish the colony,” he said. “I grew up in a family in Connecticut which had gourmet food retail stores called Hay Day.” His mother, Sallie Drackett, went to culinary school and handled the produce and baked goods while his father, Alexander, took care of the business side. What started as a mom-and-pop store grew into a popular string of markets, bakeries and wine shops, which were eventually bought up by Sutton Place Gourmet and re-branded as Balducci’s.
“And so I grew up bagging groceries and stocking tomatoes, in a small-business environment where you really appreciated the entrepreneurial spirit,” he said. Even after he’d embarked on his own career, his parents made him work in the store on the day before Thanksgiving, “as a symbolic gesture so that everybody knew that everyone was pitching in, even a Van.”
He attended Fairfield Country Day School and still remembers the school motto: Laboribus Iudicamur, meaning “we are judged by our deeds.” After that it was off to boarding school at St. George’s, in Newport, R.I., where many generations of Van Rensselaers had spent their summers sailing and socializing at the New York Yacht Club and the Spouting Rock Beach Association.
Indeed, Mr. Van Rensselaer was introduced to the club life at a young age. When he was 17, his father got him going at the super-exclusive Society of the Cincinnati; George Washington and Alexander Hamilton were early members.
“In order to be in that society, you have to be a direct descendent of somebody who was an officer in the Revolutionary War,” he said. “And it’s different from Sons of the Revolution and some of these other societies because your ancestor has to be an officer.”
Back then, dressing up in white tie and tails and donning ribbons and medals was a chore. Over the years, it’s grown on him: “I sort of appreciate that it’s a lost cause to have that appreciation.”
He understands that such traditions don’t always sit well with the uninvited. “On the one hand, gosh, you know, what great appreciation for these people, many of whom gave their lives for our freedom,” he said. On the other hand, to embrace that tradition in this day and age, “you come off as someone who thinks they’re better than everybody else, who is trying to be partitioned off from the rest of New York.”
It’s a dilemma that Mr. Van Rensselaer has learned to accept since moving to New York and joining the various clubs his forefathers patronized or had in some cases helped found. There is the Racquet & Tennis Club, where he plays squash, and the Yacht Club, which brings back fond memories of his father’s sloop placing third in the annual regatta when he was a boy. These days, his father keeps more modest, recreational boats at their home outside Newport. Mr. Van Rensselaer gets less use out of the Holland Society and the Brook Club, where he maintains a membership more as a nod to his ancestors, whose portraits hang on their walls. He understands that not everyone who’s born into the legacy of old New York shares his interest in the club life, but he finds it silly that so many get caught up feeling uncomfortable about their wealth.
“Nobility is defined by your actions; it’s not a birthright, and it doesn’t really matter what you’re born with. You’re judged by your actions and how you see your purpose on the planet,” he said. “There are plenty of people who have been born with a lot of wealth and great names who have done great things. And there are plenty of people that have been born with so much that has been given to them that they have totally screwed it up. And there are some amazing rags-to-riches stories. I think if you’re a person who’s confident in themselves, who’s trying to figure out their place in the world….You know, none of us decide how we wind up here.
“To go off and get all hung up on all that stuff is a distraction from—and whether you have means or not, or have a name or not—you’re still going to have to get off your ass and go figure out what you’re going to go do with your life.”
After college, Mr. Van Rensselaer had an idea of where he was going and managed to get there with the ease of a dandelion floating on a summer breeze. First he did a stint handling marketing for Hay Day, then took a job in the city at a small advertising firm. Next he moved to Cleveland and handled brand management for the Heinz Corporation. He wound up at Cingular Wireless, now AT&T, where he was eventually promoted to executive director of national marketing and commuted to Atlanta. One of the things he handled was youth markets. At an event held at the Iowa caucuses, Mr. Van Rensselaer gave a speech to a group of teenagers. “It is often said,” he told them, “that Thomas Paine’s Common Sense is one of the most important historical texts. Texts. And now you have the power to change the course of the political discourse in the next election with the power of the text.”
In February, Mr. Van Rensselaer left Cingular AT&T to found Van Rensselaer Enterprises; he plans to unroll a number of small digital media sites. He recently launched his first Web venture, icringe.com.
“We came up with this idea that every group of friends has a bunch of statements or terms that they love and hate,” he explained. “So my least favorite in the world is this expression ‘happy camper.’ When I hear someone say ‘happy camper,’ I want to punch them in the face.”
“Mine is ‘good for you,’” said Ms. Minneke. “I’m German, and when someone says, ‘Good for you,’ it’s like”—she did her best cringe face. She said she also dislikes the word “moist.”
“So you log on, and you get served up a term and vote on it. And you give it either a negative five, which is a full cringe, or a plus five, which is a cheers, meaning you really like the expression,” said Mr. Van Rensselaer. There is also a function where you can send someone an anonymous e-mail to let them know they’re using an unpopular expression.
He says the fact that he’s his own man is also demonstrated in the way he makes a dinner reservation these days.
“A lot of times now if I’m making a dinner reservation, or if I do something, it’s really just Van,” he said. “Now with the way databases work, and since the name is really not that common anymore, it’s 13 letters long. So while I appreciate the heritage, and I want to be proud of the origins of family, if I’m making a reservation at a restaurant, it’s really easier to say the last name is Van.”
Ms. Menniken nodded. “Actions speak louder than anything else, and knowing him and—it’s sort of like making dinner reservations and just saying Van.… Not anything relying on the name, just relying on the person you are and what you stand for,” she said. “It’s so much more important than anything else.”
Mr. Van Rensselaer lives in a townhouse he owns on the Upper East Side and still hangs out with many of the friends he made at St. George’s. During the summers, he spends a lot of time at his parents’ house in Newport; his folks now spend most of their time in Jupiter Island, Fla.
He occasionally dons a traditional mess jacket for some of the charity events in Newport and still puts on the monkey suit for the Society of the Cincinnati events every year.
“Sometimes you can feel like a real jackass,” he said. “Like, ‘What am I doing standing around with a bunch of medals around my neck.’”
I asked him if coming from a family that has surely endured its share of booms and crashes was heartening in these dire times.
“I think these things are cyclical, and great families survive if they’re intelligent. And again, if they have a lot of members of the family who are actually out there trying to make something of themselves,” he said. “These things are horrible and they destroy wealth and they destroy opportunity for a lot of people, but hopefully great families who have more than one person who have done some great things can continue to preserve capital and build new wealth—so when something like this happens, you’re not destroyed, you’re set back.”
Then Mr. Van Rensselaer and Ms. Menniken hopped in a chauffeured SUV and headed down Park Avenue.