IfOnly, a marketplace for experiences, has new funding — and a new CEO

IfOnly, a San Francisco-based online marketplace that offers more than 3,000 unique experiences to its adventuresome users, has raised $20 million in Series D funding led by MasterCard, which was joined by other strategic investors, including Hyatt Hotels and Sotheby’s.

It has another new announcement, too: The company has brought aboard a new CEO, John Boris, who spent the previous six years as the chief marketing officer at the personalized photos and products company Shutterfly.

The latter wasn’t necessarily something the company saw coming. Until recently, IfOnly was led by serial entrepreneur and founder Trevor Traina. But in January, Traina — a financial supporter of President Donald Trump — was nominated for an ambassadorship to Austria, and last Thursday, he was sworn in at his Pacific Heights home in San Francisco.

With Traina off to Vienna, Boris will steer the company’s growth, and its newest strategic partners should help.

Both MasterCard and Hyatt, for example, offer the kinds of experiences featured at IfOnly to help make their offerings a bit stickier for customers.

Meanwhile, Sotheby’s, known of its auctions business, has similarly been getting into the business of experiences. In December, anyone willing to pay enough could enjoy an after-hours tour of the Peggy Guggenheim Collection in Venice, Italy, before being treated to an authentic Venetian dinner. Another experience recently auctioned off by Sotheby’s: the ability to host a private lunch or dinner for 10 at the iconic Philip Johnson Glass House in Connecticut.

Both of these opportunities were expected to fetch in the tens of thousands of dollars — which is in the range of plenty of experiences featured on IfOnly. Among the costlier options available right now on its platform is a private concert with the band Third Eye Blind — which requires that interested parties “request a quote” — and a one-of-a-kind crystal pet pendant by L.A. designer Irene Neuwirth, who, for $21,000, will also carve out enough time to say hello.

IfOnly is also going after a much broader audience — one that may be looking for fresh experiences that won’t cost an arm and a leg. It seems to be making some progress on that front, too.

The company has now attracted two million registered users, and Boris says that roughly 25 percent of them engage regularly with the platform. Two years ago, when we spoke with Traina about the company’s Series B round, IfOnly experiences were only available in San Francisco, L.A. and New York. Now, the platform features experiences in eight cities. It also seems to feature a greater breadth of experiences, and many more affordable options. (Among them: glass blowing in L.A.’s Hermosa Beach, Calif., for $99 per person.)

The company has plenty of competition, of course. Its most daunting rival may well be Airbnb, which is deriving a growing percentage of its revenue from travel services and bookable excursions with locals.

Asked about this, Boris stresses that every experience on IfOnly is “vetted,” suggesting that Airbnb might not be controlling quality as tightly. He also says he welcomes the attention that Airbnb is paying to experiences. “It legitimizes that there’s a multibillion-dollar market here,” he says.

IfOnly has now raised more than $40 million altogether. Other investors in its newest round of funding include the venture firms New Enterprise Associates, Founder’s Fund, Khosla Ventures and TriplePoint Capital.

Pictured above: a photo on IfOnly of a Half Dome adventure hike in Yosemite. Price: $290 per person.