With a family tree that includes President James Buchanan, the founder of Dow Chemical, the philanthropist behind San Francisco’s celebrated de Young Museum, and the creator of the Swanson TV dinner, you might assume that Trevor Traina would have chosen to loll around on his silver spoon. And yet, the 40-something-year-old, whose family first put down stakes here during the Gold Rush, has become a driven serial entrepreneur instead.
His first company, Compare.net, sold to Microsoft in 1999 for a cool $100 million when Traina was only 30 years old. He then went on to build and sell three more companies in the tech sector in the following decade. Now, he’s melding his entrepreneurial spirit with his status as one of San Francisco’s most prominent socialites and philanthropists to bring you IfOnly, an online marketplace of uniquely curated dream experiences. What does that mean? Think of a one-on-one meet and greet with soccer’s Cristiano Ronaldo, then watch him play a match from his private suite. How about traveling in the VIP car of the Napa Valley Wine Train as Chef Donald Young leads you on an epicurean journey while you journey past the scenic vineyards? It’s an experience that can be yours on IfOnly.
The list of luminaries who are packaged with the experiences runs long and heavy on A-listers. Several come from Traina’s vast network of connections, but others may have signed on because of a spin within the business model: 20 percent of each purchase goes to the luminaries, half of which they’re required to donate to a charity of their choice. It’s smart business sense with a philanthropic side benefit. To Traina, business and philanthropy go hand in hand.
On Why He Loves His Hometown
If you care about ideas, San Francisco is the Florence of our time. From iPhone to Tesla, from Uber to Facebook, the things that are changing the whole world are coming from a small geographic area at a very amazing time in history.
On Why He Works When He Doesn’t Have To
I work for the pleasure of creating. Specific to IfOnly, I’ve always found it easy to bring people together. IfOnly was the extension of that, offering connections and inspiration to a much larger audience.
On the Definition of the “Experience Economy”
The recent economic downturn forced people to reassess what is important to them. They looked in their drawers and cupboards and realized they had ample physical things but that spending money on experiences is a richer, more satisfying way to live. I see a day not too far away when people are primarily focusing their dollars on living experientially versus owning a million things. And I imagine IfOnly at the center of that economy. No one has created such an emporium for experiences. That’s the opportunity I saw.
On Being a Darling of the Tech Industry with No Tech Background
I think it’s my secret weapon that I have a consumer background. Many tech entrepreneurs can get lost in the weeds in the attributes of products. I focus on the benefits of what we offer and the consumer value proposition.
On the Connection between IfOnly, Napa, and Wine
Napa combines so many aspects of rich experiential living: wine, physical beauty, mild climate, and world-class cuisine. Some of my fondest memories are from growing up in the valley in summers and weekends. I learned about wine, drinking it with Robert Mondavi. I remember when Oakville Grocery was just a general store, and some of the original chefs of the valley were making Napa into a food destination, like Thomas [Keller] starting The French Laundry. I grow grapes myself, and my wife and I have a home that’s one of the original winemaker estates from the 1850s in the center of Oakville.
On How the Napa Valley Wine Train Fits for IfOnly
With the leisurely pace of the train, it’s one of the best ways to see the beauty of that unique destination. And the wine train is an experience in and of itself; the challenge was creating something above and beyond that fit IfOnly. I’m proud of what our team came up with.
A grand building of exposed brick, Douglas Fir beams, and seaside character, The Argonaut is a boutique hotel in San Francisco’s Fisherman’s Wharf. Housed in the historic Haslett Warehouse, which was built in 1907, this family-friendly hotel features faux leather wall treatments, canvas-wrapped tuxedo-style sofas, and nautically themed wall decor. Mere steps from one of San Francisco’s best-loved sites, this hotel has delightful extra touches, like a yoga mat in every room, that are sure to make your stay remarkable.
Nestled along the River Trail and the Oxbow Park Preserve of Napa Valley Wine Country, the River Terrace Inn is a relaxing sanctuary for oenophiles. From the complimentary afternoon wine hour to the courtesy cruiser bicycles guests can use to take a jaunt down to local shopping and dining areas, the inn is ready to guide you as you explore the renowned Napa Wine Country. For those looking for the full Napa wine experience, book a seat on the Napa Valley Wine Train and see Wine Country in style.