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Apr 06, 2014
COVER STORY The Art Of Living: Inside Trevor Traina's Pacific Heights Home - Forbes

I’ve spent my entire life as a connector of people,” Trevor Traina says in his cozy San Francisco den. It’s the end of a long day that some would find exhilarating, others exhausting and Traina simply typical. The 45-year-old tech entrepreneur had woken up in Los Angeles that morning, having spent the previous evening at the Oscars. That afternoon, he canceled his Virgin America flight home in favor of hitching a ride on a friend’s private jet. Then he was out until the wee hours having dinner with a Disney executive and some tech-mogul friends at Spruce, a cozy, Michelin-starred Presidio Heights restaurant in which he is a co-investor. Is this socializing, is it business? For Traina, it’s the sweet spot of a career spent nurturing relationships with talented people.

Traina And Portraits

“It was interesting to see how many people at dinner were also at the Academy Awards,” he says as he settles in to a vibrant-blue Etro-upholstered chair. “It really hit home that San Francisco has become the center of the idea economy.” And for the past few years, Traina has been holding that center–linking the Bay Area’s tech titans with the city’s Old Guard. His 1905 Georgian town house defines that nexus. Situated in Pacific Heights, one of the city’s most rarefied neighborhoods, the home, which Traina shares with his wife, Alexis, and their two children, was decorated by his neighbor Ann Getty. Just down the block are Oracle’s Larry Ellison, Yelp CEO Jeremy Stoppelman, Zynga’s Mark Pincus and Apple’s design genius, Jony Ive.

Mirror Effects

The mix is no coincidence. “Over the years I’ve reached out to the people I care about and recruited them to colonize the coolest and best part of the city,” says Traina, who matches friends and nearby real estate with the enthusiasm of a high-commission broker. “Who wouldn’t want to be surrounded by the brightest and best minds that they know?”

 

Expansive views of the Golden Gate Bridge and Alcatraz compete with Traina’s remarkable 300-piece photography collection–including works by Walker Evans, Robert Frank, Cindy Sherman and Andreas Gursky. “Because of my two kids, my wife has exiled the more risqué images to far walls,” he says, staring out from behind one of his Frederick Remington statues.


Trevor Traina

 

“It’s a handsome, dignified house,” he says modestly. “We wanted its look to give a nod to history and tradition, but also a sense of youth and wit.” A life-size black-and-white Hiroshi Sugimoto photo of Queen Elizabeth rules over the Cool Britannia red hand-blocked velvet-lined living room. Downstairs in the green-and-white conservatory filled with lush trees, a Richard Serra circle painting and a giant skylight. The airy dining room overlooking the garden is balanced by two custom-made banquettes, Venetian grotto furniture and a proud pair of peacocks. (The grotto furniture has sentimental meaning for the Trainas–it was used as part of his surprise marriage proposal in Bergdorf Goodman’s handbag rotunda.)

 

Below the house is something almost as dramatic: a 3,000-square-foot basement blasted out of solid granite to display the photography collection away from sunlight.

 

This was not the first time a Traina had dynamited the hills hereabouts. The scion of one of San Francisco’s grandest families, Trevor Traina was born into a family that arrived here during the Gold Rush. His late father, John, was a San Francisco shipping magnate, art collector and legendary bon vivant. His mother, philanthropist Dede Wilsey, is the powerhouse behind the 2005 reopening of the de Young Museum, the Herzog & de Meuron-designed fine arts temple. The family tree also includes great-great-grandfather Herbert Henry Dow, who founded Dow Chemical; Trevor’s onetime stepmother, bestselling novelist Danielle Steel; and his former stepbrother, Sean Wilsey, author of the bestselling memoir Oh the Glory of It All, which redefined sibling rivalry, the perils of wealth and why children should never have unsupervised access to their stepmother’s lingerie drawer. Just about the only member of Traina’s clan who seemed to have escaped the blessings of providence was President James Buchanan, who had the misfortune of being followed in the White House by Abraham Lincoln.

 

Instead of counting his inheritance or riding the express lane to Wall Street like so many of his peers, Traina transformed his silver spoon into a full platinum table setting through a series of Internet startups. After graduating from Princeton and Oxford, he became a brand manager for Seagram’s wine coolers in New York. “It used to be embarrassing to go to bars and demand Sunset Passions,” he remembers, as he sips a glass of cabernet from his in-laws’ Swanson Vineyards in the Napa Valley–his wife, a wry Southern beauty, is from the frozen-foods family. Traina has his own Napa vineyard, “but if you want to be friends with your wife,” he explains, “you drink her wine.”

 

After Seagram’s, Traina returned to the Bay Area to attend Berkeley’s Haas School of Business. “I knew that this big thing was happening across the Bay [in Silicon Valley] and that I was going to leave business school with a startup Internet company,” he recalls. “I started hanging out in the computer lab and never once visited career services.”

 

His first Big Idea came in the mid-’90s, when he tried to buy a cordless telephone. “The salesman was this expert in a red blazer and name tag, and couldn’t tell me the individual features of the different phones. There were no databases of products where you could compare television sets or phones and that sort of thing. I thought that if we could give people that information online, we could control what to buy and we could influence where to buy.”

 

At the time it was a breakthrough idea. So with $300,000 in funding from friends and family (and receiving a credit from Haas for writing up the business plan), Traina hired a small team of programmers, moved them into the upstairs nursery of his father’s house and launched CompareNet. “During the days, we’d work on little painted-rabbit tables and pack everything away when the kids had to go to bed,” Traina says. “Eventually my father said, “You have a dozen employees now–it’s time to get an office.’ ”

 

Three years later, Traina sold CompareNet to Microsoft for a reported $100 million. “I was 30,” he says. “And I told my parents that they were now free to live as long as they wished.” Over the course of the next decade, he and his partners founded and sold three more tech companies: Schema Logic (a document-management service), StepUp Commerce (which connected retailers with online shoppers) and DriverSide
(a site on which car owners could manage their vehicle maintenance).

 

It wasn’t all work. Traina firmly believes in taking Richard Branson’s “funtrepreneurial” approach to his businesses. In 2008, to generate publicity for DriverSide, he drove an Audi R8 in the Gumball 3000 rally from San Francisco to Beijing (with the help of a cargo plane). The odyssey even involved an overnight stay in Pyongyang as a guest of the late Kim Jong Il, who, among other things, was a car aficionado.

 

Traina’s business instincts also apply to the arts. “Collecting is a disease that runs in the family,” he says. “My father collected Faberge jewelry and vintage cars. I started by collecting American art in my twenties. I thought that at the time I would never have the kind of wallet to have a great collection, so I turned to photographs.” To decorate his office while at Seagram’s, Traina had chosen from the company’s extensive collection a Nicholas Nixon photograph, “View West from Park  Avenue and 55th Street, New York City.” Years later, he saw the image for sale at an auction and purchased it. “My name was still scribbled in pencil on the back,” he says with a smile.

Traina made headlines for his collecting in 2004, when he bought an original print of the iconic Diane Arbus photo “Identical Twins” for $600,000. “That was a pretty serious acquisition, but it would probably go for a lot more than that now,” he notes.

Stairs

Two years ago, his collection was exhibited at the de Young Museum, where he is a board member. He sits on the board of six other nonprofits as well. “Philanthropy has always been very important to my family, and I firmly believe in giving back,” he says.

 

His passion for philanthropy, business and adventure converged in 2012 while he was looking for a Christmas present for his younger brother, film producer Todd Traina, a tennis fanatic. At a charity auction, he bought an hour of tennis with John McEnroe. “I suddenly realized that that’s what people ultimately want when they’ve filled their closets with baubles: experiences. Something special that you can build anticipation for. That’s the ultimate luxury.”

 

Raising $3 million from angel investors, including his neighbors Mark Pincus and Jeremy Stoppelman, plus Yahoo CEO Marissa Mayer, Salesforce CEO Marc Benioff and Russian billionaire Yuri Milner, Traina launched IfOnly (ifonly.com) late last year. The company offers one-of-a-kind items and experiences, from a $35 guitar pick signed by Chris Cornell (formerly of Soundgarden) to a $45,000 private training session with Hall of Fame wide receiver Jerry Rice–”luminaries,” as Traina calls IfOnly’s talent. Those who can’t find their dream experience in Traina’s impressive lineup can fill out a “wish list.” So if you want to, say, play a round of golf in Big Sur with Greg Norman or have Alice Waters oversee the catering for your private dinner party, it can be arranged. Half of IfOnly’s business is now bespoke.

 

There’s also a philanthropic component to the business. IfOnly takes 20 cents of each dollar spent, while the luminary and charity split the rest, with a required minimum of ten percent of the gross going to the charity. “Most of the luminaries are doing this for charity, so most, if not all, of their part is usually donated,” Traina explains. Right now some 150 charities–including Meals on Wheels and Stand Up to Cancer–are benefiting from IfOnly.

 

Working out of a bright penthouse watched over by a giant stuffed bison head in San Francisco’s North Beach neighborhood, Traina has gathered a team of 35 engineers, account managers, marketers, copywriters and, most important, “talent wranglers” like himself. “We have specialists for our categories to reach out to luminaries,” he explains. “Our tennis person used to do all the tennis sponsorship for Reebok. Our food guy is a well-known food critic.” Music, entertainment, wineries and golf are among IfOnly’s other categories.

 

Wishes are delivered via cleverly devised themed packaging–a quarterback experience with Joe Montana ($43,000) will arrive in a box with a note resting on a piece of turf. If you purchase an Italian wine apprenticeship with master sommelier David Lynch ($3,200), the box will be lined with corks. A signed pair of golf pants worn by Gary Player in the 1960 British Open ($10,000) will come wrapped with white golf tees.

 

“The possibilities are endless,” says Traina, who has already sold 2,000 experiences. “San Francisco right now is like the Florence of the Medicis. There’s this incredible mix of business and art and creativity that’s producing a new Renaissance.” And what better place for a Renaissance man to play than amidst the dizzying variety of activities offered by IfOnly? Of course, if you want someone to design and furnish your own Pitti Palace, Traina can undoubtedly find the luminaries to do that, too.

   
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