Trevor Traina at his San Francisco home, which was decorated by Thomas Britt and Ann Getty and showcases his photography collection. Photograph by Ian Allen.

SAN FRANCISCO - Trevor Traina is a 21st-century merchant prince. His stock-in-trade: dreams and once-in-a-lifetime experiences. Evanescent as his products may be, they leave lasting impressions and make substantial contributions to charity.

That’s the point of Traina’s newest venture, IfOnly, a site through which individuals can connect with some of the world’s foremost talents.

“We all have too many cashmere sweaters and handbags,” he says, explaining his initial inspiration for the site.

“I realised that all my friends were increasingly interested in experiences rather than just physical things.

“But while there are wonderful places to go to buy beautiful things, there was no emporium for experiences. So I thought, why not create the first top online emporium where you can you can go to get incredible experiences, at every price point?

“If you like food, you can go shopping at the Farmers Market with Alice Waters, or April Bloomfield of the Spotted Pig can teach you how to butcher, for example. If you like basketball, would you like to shoot hoops with Kobe Bryant?”

Shop at the farmer’s market with chef Alice Waters, leader of the locavore food movement.

Traina has a proven track record building companies from scratch. A Princeton graduate, he sold his first company,, to Microsoft when he was 30 for $100 million, and has gone on to sell three more Internet start-ups.

“So I was looking for something to do,” says Traina on a recent afternoon in the palm-filled conservatory of his 1905 Georgian-style house, where he lives with his wife, food-and-wine heiress Alexis Swanson Traina, and their two children. Their block, the epicentre of San Francisco’s Gold Coast, is also home to, amongst others, Gordon and Ann Getty (who decorated Traina’s house), Larry Ellison and Mark Pincus.

Recently, Traina was dubbed the “undisputed social king of San Francisco” in Vanity Fair. “Apparently, I’m quite the Svengali,” he says, poking fun at his image. “I would not quite describe myself as the nexus of everything here.”

But it would be hard to dispute the notion that Traina has been the bridge between the young tech moguls who have migrated to San Francisco and the city’s Old Guard elite. He is, after all, a card-carrying member of both groups. And bridging the divide between the two has been key to his success.

He was born with access to any door in San Francisco thanks to his father, the late shipping executive and connoisseur John Traina, and his mother, the former Diane Buchanan, who is known as Dede and is a great-great granddaughter of Chemical magnate Herbert Henry Dow. After the couple amicably divorced, John Traina married novelist Danielle Steel and Dede was wed to prominent businessman Al Wilsey. For many years, Mrs Wilsey has been the acknowledged social and philanthropic powerhouse of San Francisco.

Pair truffles with wine at Brezza Winery in Barolo, Italy.

“I grew up part of Old San Francisco,” Trevor says. “But my passion has always been technology and progress. I do like to connect people. My philosophy is, more is more.

IfOnly is really about connecting people, and trying to make them happy. These new tech people are incredibly intelligent and dynamic. They are helping themselves along, but because I’ve been involved in philanthropy probably longer than most of them I have been trying to shepherd them into causes where they can contribute their talents. Non-profits are always looking for talented people, and I am more than happy to be that connector.”

Key to Traina’s concept for IfOnly is its charitable component: “The luminaries who are providing the experiences have the option to keep some of the money they receive, but a portion must go to a charity of their choice; many of them have been donating all their proceeds to their charity.”

Hence the stellar roster of talents who have agreed to offer services to IfOnly. While a portion of the site is open to the public, many of its treasures are available only to members. All Sotheby’s Preferred clients now have exclusive access to this invitation-only community.

The range of experiences and goods available to members is vast. “We sell things from $30 to $300,000, and the site is divided into categories such as sports, lifestyle and music,” Traina says.

 “We can literally make anything happen. We just sent a group truffle hunting near Lake Como, we arranged a dinner with a top NBA star for one customer, we just sent ten CEOs to a dinner at Screaming Eagle Winery, which is impossible to do. Screaming Eagle did it because it benefited the Land Trust of Napa County. So everybody was a winner, and no one went hungry.

Share a wine tasting with writer and wine expert David Lynch.

“Sometimes customers just call me and say, ‘Dazzle me. I want an experience no one has ever had.’ So we come up with a bespoke event for them. Our team will arrange all the logistics.”

How has Traina managed to pull it off? “If it were easy, other people would have done it,” he admits. “This is a marriage of all of my passions, hobbies, contacts and talents. I assembled a tech team, with five patents pending, to fulfill all this on the site. To get the ball rolling, I contacted most of the luminaries myself. Recently I have hired a number of what I call ‘talent wranglers,’ who are well known in their fields. They are extending my reach.”

IfOnly plans to expand into additional fields including fashion and art.

“If you want to attend a fashion show with a top editor, we can arrange it, for example. We’ll find eminent curators and experts with whom you can go on a gallery visit.”

Traina himself has collected in several areas. “I started with 19th-century Western American art, but my tastes shifted to photography. I felt I had a much better opportunity to make a statement there; I could go further and do more.”

That he’s done. Beginning with a 1969 Diane Arbus portrait of a pair of twins, which he saw on the cover of a Sotheby’s catalogue, Traina has amassed some 300 choice works, including pieces by Robert Frank, Jeff Wall, Andreas Gursky, Cindy Sherman and Thomas Struth. In 2012, highlights of the collection formed a major exhibition, “Real to Real: Photographs from the Traina Collection,” at the de Young Museum, where Traina is a trustee.

As the holidays roll around, Traina is preparing for heightened traffic on IfOnly, even though every day there seems to be Christmas.

“We think of everything we offer on IfOnly as a gift, even if it’s to yourself. Everything is an opportunity to connect, inspire and delight.”

To that end, Traina recently clicked on and bought a present for himself and his wife. “We had plans to take a group of customers to the iHeartRadio festival in Las Vegas (iHeartRadio CEO Bob Pittman is an IfOnly investor), so I bought a backstage meet-and-greet with Justin Timberlake after the show. He couldn’t have been nicer, and all the money benefited the Ryan Seacrest Foundation.

“So I tell people about IfOnly; I’m not just the founder, I’m also a customer.”


James Reginato is writer-at-large of Vanity Fair.

Tags:San Francisco, Interviews