At $5 Million, Balloon Ride Over Everest Benefits Charity

By Andrew Romano

IfOnly CEO Trevor Traina wants to peddle one-of-a-kind experiences the way Jeff Bezos... Read More

On the top floor of an anonymous office building somewhere in San Francisco, there is a wardrobe as transporting as anything C.S. Lewis dreamed up -- and Trevor Traina has the key.
“These are Usher’s shoes,” Traina says as he reaches inside for a pair of Air Jordans. “This is Bruno Mars’s guitar. Those are Kobe Bryant’s game-worn sneakers. There’s Rob Thomas’s guitar, too.” He shakes his head and smiles. “Pretty funny, isn’t it?”
Funny is one way of putting it. Innovative is another -- and lucrative might be next, Bloomberg Pursuits will report in its Autumn 2014 issue. Welcome to the headquarters of IfOnly, a startup that Traina, its 46-year-old founder and
chief executive officer, touts as “the world’s first store for amazing experiences.”
Plenty of websites offer products -- and Traina does, too, as his closetful of starry souvenirs attests. However, the bulk of IfOnly’s business comes from something less tangible and ultimately more valuable, or so Traina’s investors hope: a platform that lets you do pretty much anything you’ve ever dreamed of.
So far, the site offers two kinds of experiences. The first is off the rack: Luminaries (Andre Agassi, say, or Lady Gaga) offer unique encounters (a private tennis lesson, a dressing-room meet and greet) at a set price, and then donate the proceeds to a charity of their choosing (minus IfOnly’s 20 percent cut).

Custom Offerings

The rest of IfOnly’s offerings are custom: A client conjures up an idea -- often vague, usually improbable and rarely cheap -- and Traina and his team of talent wranglers make it happen. Recently, Traina says, an unspecified company wanted to host a private concert by “a very famous current performer.” Done. The price tag? $2.4 million.
Even IfOnly’s less-astronomical experiences tend to be rather rarefied. Palm Beach restaurateur Piper Quinn knew he wanted to invite 20 family members and friends to the Napa Valley for his 40th birthday, but he let IfOnly fill in the blanks. The result, he says, was “a weekend I didn’t even think was possible”: a first tasting of Promontory, a new wine by Napa legend Bill Harlan; a dinner at the private Napa Valley Reserve; and a tour of The French Laundry’s culinary garden, followed by an outdoor pig roast at Thomas Keller’s Bouchon. “I wanted something that most people couldn’t do,” Quinn says. “But I didn’t know who to ask or how to get it done. IfOnly did.”

Storied Family

It’s a role that Traina, a scion of one of San Francisco’s oldest families, says he was born to play.
“I’ve always been a connector,” he explains.
Traina’s great-great-grandfather Herbert Henry Dow founded Dow Chemical Co. (DOW) His late father, John Traina, was a storied shipping magnate, vintner, Faberge collector and all-around bon vivant. His mother, philanthropist Dede Wilsey, is descended from President James Buchanan. His stepmother is novelist Danielle Steel.
In spite of a cushy upbringing, Traina has proved himself to be one of the Bay Area’s craftier tech pioneers. By 30, he had sold his first company to Microsoft Corp. (MSFT) for $100 million. During the next decade, he built and sold three more startups. Yet Traina insists with the near-religious fervor of a serial entrepreneur that IfOnly is more promising than all of them put together.

‘EBay-Sized Business’

“This is definitely my biggest idea,” he says, noting that IfOnly’s list of investors reads like a social register of Silicon Valley: Salesforce.com Inc. CEO Marc Benioff, Yahoo! Inc. CEO Marissa Mayer, Russian billionaire Yuri Milner. “I think the market is potentially so huge that this could be an EBay-sized business.”
Traina was inspired to start the company after buying his brother an hour of tennis with John McEnroe at a charity auction.
“I realized these sorts of experiences were fun and pleasing to people,” he recalls. “But if you weren’t at the right black-tie dinner at the right time, you missed out.” Then he started crunching the numbers. “My estimation was that entertainment and big professional sports stars cashing in on their famous names with side stuff is already worth about $30 billion,” he says. “And that doesn’t even include squash players and Nascar drivers and authors.”

Twofold Plan

So Traina’s plan is twofold. First, move into new fields: squash, Nascar, publishing and so forth. That expansion is already under way. More fascinating is what comes after. During the next 18 months, Traina expects to open up IfOnly to outside vendors, along the lines of Amazon Marketplace.
“We have very broad ambitions,” he explains. “We envision IfOnly as an open platform across hundreds of categories. Say someone is a top battlefield historian. He can use our technology to set up a whole shop. He can create custom itineraries, offer phone consultations or signed copies of his book and even walk a battlefield with you. That’s ultimately our vision.”
In the meantime, Traina has his own experiences to peddle, including, at the top of the market, a balloon expedition over Mount Everest for a mere $4.8 million.
“You have a 70 percent chance of surviving,” Traina says with a smile. “Which I think are pretty good odds.”
(Andrew Romano is a contributing writer for Bloomberg Pursuits. Opinions expressed are his own.)