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 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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