The art of living: Inside the home of tech entrepreneur Trevor Traina

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 favour 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 socialising, is it business? For Traina, it’s the sweet spot of a career spent nurturing relationships with talented people.

“It was interesting to see how many people at dinner were also at the Academy Awards,” he says as he settles into a vibrant-blue Etro-upholstered chair. “It really hit home that San Francisco has become the centre of the idea economy.” And for the past few years, Traina has been holding that centre—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 neighbourhoods, the home, which Traina shares with wife Alexis and their two children, was decorated by his neighbour 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.

The mix is no coincidence. “Over the years I’ve reached out to the people I care about and recruited them to colonise 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.

Birdland: Two peacocks (a gift from Traina’s stepmother, Danielle Steel) proudly watch over the dining room, which features custom-made banquettes and a photograph by Joel Meyerowitz

“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—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. The scion of one of San Francisco’s grandest families, Traina was born into a family that arrived 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 includes great-great-grandfather Herbert Henry Dow, who founded Dow Chemical; Trevor’s one-time 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. The only member of the 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 this big thing was happening across the Bay [in Silicon Valley] and that I was going to leave business school with a startup 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 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: SchemaLogic (a document-management service), StepUp Commerce (which connected retailers with online shoppers) and DriverSide.com (a site on which car owners could manage their vehicle maintenance).

Image: Gabriela Hasbun
Venice anyone? The entrance gallery evokes a Venetian palazzo, albeit one with Portuguese chairs, a 19th century Chinese shrine and a painting by Turner Prize-winning artist Keith Tyson

It wasn’t all work. Traina firmly believes in Richard Branson’s “funtrepreneurial” approach to 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 involved an overnight stay in Pyongyang as a guest of the late Kim Jong Il, who 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 Fabergé jewellery 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 collec- tion, so I turned to photographs.” To decorate his office while at Seagram’s, Traina had chosen from the company’s 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 smiles.

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.

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 non-profits. “Philan-thropy has always been very important to my family, and I firmly believe in giving back.”

His passion for philanthropy, business and adventure converged in 2012 while 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 realised 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 neighbours Mark Pincus and Jeremy Stoppelman, Yahoo CEO Marissa Mayer, Salesforce CEO Marc Benioff and Russian billionaire Yuri Milner, Traina launched IfOnly (ifonly.com) late last year. It 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 line-up 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 dinner party, it can be arranged.

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 10 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 says. Right now some 150 charities are benefiting from IfOnly.

Working out of a penthouse watched over by a giant stuffed bison head in San Francisco’s North Beach neighbourhood, 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 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 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.