The Wish Master: How Trevor Traina Makes Dreams Come True

Photography by Michael Keeney    Clothing by Brooks Brothers

When Trevor Traina arrives in his impeccable office by Levi’s Plaza in San Francisco, he blurts out the first thing on his mind: “Kim’s ring is gorgeous!” He is, of course, talking about the 15-carat Lorraine Schwartz stunner that reality star Kim Kardashian received just days before from Kanye West after he proposed at San Francisco’s AT&T Park.
Traina was part of the exclusive crew that actually witnessed the affair, and also among the first to lay eyes on the aforementioned ring. As one of Kanye’s confidants, it’s only natural that he’d have intimate knowledge about the epic proposal. “Kanye told me that he had gone through three designers and had the ring finished just that day,” he shares.
One might wonder how Traina, part of the “old guard” of San Francisco society, would have any connection to the controversial rapper. This is quite easily explained, as Traina is the CEO and founder of IfOnly, an e-commerce site that sells curated experiences with star personalities from the worlds of food, sports and music who then donate a portion of the profits to the charities of their choice. A few extraordinary experiences IfOnly has offered in recent years include a dinner party with Chef Michael Chiarello, a group swimming clinic with Olympic swimmer Summer Sanders and a private quarterback camp with NFL superstar Joe Montana.
Now, the 46-year-old Internet entrepreneur is working with West to put together “a really incredible, once in a lifetime experience.”
Traina is here to discuss his business, and West is part of that. In less than an hour the two will meet for lunch to collaborate on a VIP experience for IfOnly that he can’t yet discuss. Though he won’t divulge any details on the upcoming experience, Traina is more than happy to reveal his personal thoughts on West. “He’s really cool and he’s an ideas person. He’s very special and gifted,” he says, before remarking, “Often these types of people have creativity that is bursting out of them, almost uncomfortably so.”

Photography by Drew Altizer    Clothing by Brooks Brothers

The technology entrepreneur is a perfect match for West’s unbridled energy. On any given day, Traina floats among socialites, Silicon Valley entrepreneurs and pop-celebrity culture. He serves on a number of boards including the Fine Arts Museum of San Francisco and he sits on the city’s Technology Advisory Council. His business dealings in technology paired with his diverse cultural interests allow him to mix seamlessly into every circle.
As the product of a privileged upbringing, Traina was naturally primed for high society life. His parents are the late philanthropist and art collector John Traina (who later re-married novelist Danielle Steel) and Fine Arts Museums board President Dede Wilsey. His late grandfather is diplomat Wiley Buchanan who served as President Eisenhower’s chief of protocol and his grandmother, Ruth Buchanan, was an heiress to the Dow Chemical fortune.

“I am equal parts tech entrepreneur and lover of the well-lived life.”

Sitting in front of Traina, one could imagine that he is a virtual replica of his father: a beloved, well connected man-about-town who is revered by many; he is a popular figure at high-society galas and the most exclusive of San Francisco gatherings. Despite his status as a “society king”, he has admittedly spent his whole life “trying to get off the society pages and into the business pages.”
He has certainly worked hard to make that happen. Traina studied political science at Princeton and received graduate degrees from the University of Oxford and UC Berkeley’s Haas School of Business. Before creating IfOnly, he founded four tech-driven businesses that spoke to the needs of various consumers. Those companies have since been purchased by the likes of Microsoft and Intuit, among others. Compare Net, the first company he founded at the age of 28, was sold to Microsoft for $100 million.
As he puts it: “I am equal parts tech entrepreneur and lover of the well-lived life.” The idea of IfOnly was sparked when Traina was seeking to purchase a lesson with John McEnroe for his brother Todd, a tennis aficionado. Traina then recognized the opportunity to offer these rare experiences to consumers. He launched IfOnly earlier this year with funding from tech heavy-hitters Marc Benioff, Mark Pincus and Jeremy Stoppelman, among others.
“Some people even have the access [to similar experiences] but they maybe lack the time or the imagination to really come up with these things. Other people haven’t had access before, and I feel like they should have access. A rich experience doesn’t have to be expensive. It just has to be something that someone has to enable for you,” he says.

Photography by Michael Keeney    Clothing by Brooks Brothers

Even Traina can’t resist making personal purchases from the site. He recently bought a racket signed by Mark Philippoussis for his brother Todd. In that sense, IfOnly offers what Traina refers to as “I know a guy” type of experiences. Traina is that guy who knows the guy, and if “the things on the site aren’t tempting enough for me, then I wouldn’t want to offer them to my customer.”
In his eyes, the most compelling aspect of his latest company is the opportunity to do good by doing well. IfOnly is set up to donate up to an average of 70% of all money to a charity or cause, while only 10% is required; the rest goes to the luminary and a small percentage goes to IfOnly as a “platform fee”. According to Traina, it’s easy to get A-list benefactors like Madonna, Kobe Bryant, Shakira and Greg Norman to donate their time and talent if philanthropy is involved. “When you allow the luminary an avenue for promoting their cause or foundation, suddenly they become much more willing to entertain these experiences,” he notes.
Traina’s flair for giving back is surely a product of his upbringing. His father was a renowned philanthropist and his mother has turned fundraising into an art form, raising over $450 million for various causes over the course of 30 years. Traina has clearly taken a page from his mother’s book. “I grew up with a heavy influence on experiences and giving back,” he explains. “My parents were art collectors and philanthropists; I learned at their side.”
Outside of the business of giving back, Traina focuses his energy on pursing his passions. “Yes, I have connections, but I love real estate, wine and art, he says.” An avid art collector, Traina makes his way around the world from Sotheby’s auctions to Art Basel in Miami in the pursuit of fine art. When asked about his most prized possession, he points to an early photograph from William Eggleston called the Red Ceiling. “It’s important to me; [Eggleston] had a show in 1976 at the MOMA in New York which opened the door for color photography,” he explains.

“I’ve spent my whole life trying to get off the society pages and into the business pages.”

Traina also has a fondness for the classics. He talks nostalgically of a vintage Rolex given to him by his father and stepmother Steel when he was just out of grade school; he also has special place in his heart for his Audi R8, and believe it or not, he’s a huge fan of Levi’s jeans.
Because of who he is, what he does and how he was brought up, it’s only natural that Traina would have friends in high places. He and wife Alexis count Vogue editor Anna Wintour as one of their nearest and dearest, and even stayed at her place in New York last summer. Traina describes Wintour’s personality as light and playful – a much different image than the icy persona she is known for.
“She’s delightful,” he enthuses. “She has a man’s business brain, so that makes her interesting to talk to. She’s curious about trends, about business and she’s a person who has many responsibilities. She was a very gracious hostess to us and very easy to be with.” He adds with a laugh, “The only complication is you have to think harder about what you’re going to wear.”
But forget the past: at present, Traina is one hundred percent focused on IfOnly. He says proudly, “If we do our jobs well, then we’ll do so much good for so many people in need. And I think that will be part of my legacy.”