Member Profile: Trevor Traina
Technology Entrepreneur, Art Collector, Philanthropist

Trevor Traina, based in San Francisco and the Napa Valley, is an entrepreneur and private investor.  He has founded and co-founded five successful technology companies.  Four of them were sold to acquirers like Microsoft and Intuit. He is currently Founder and CEO of Traina Interactive, a venture funded company operating, a website that connects the world’s top talents to consumers to benefit charities

Trevor began his career in marketing as the youngest Brand Manager ever at Seagram's in New York. He now serves on the boards of Verdiem Corp. (funded by Kleiner Perkins) and Rewarder Inc. Involved in philanthropic pursuits in San Francisco and beyond, he also serves or has served on six charitable boards including the Haas School of Business at the University of California Berkeley, the Fine Arts Museums of San Francisco, the Princeton University Art Museum and the Gladstone Institute for medical research.


It is telling that even ten years ago, as his first bold business ventures were coming to fruition, he was already on eight non-profit boards and involved in education, the arts, and research.


Trevor holds a bachelor's degree from Princeton, a graduate degree in political science from Oxford and a master's in business administration from Berkeley's Haas School of Business.  He lives in San Francisco with his wife, Alexis, the creative/marketing director of Swanson Vineyards, and their two children, Johnny and Delphina.  And it’s notable that Trevor’s mother is the brilliant Dede Wilsey, a breath-takingly effective fundraiser and philanthropist in San Francisco.  Dede has had a residence in the heart of the Napa Valley since 1970. Trevor’s father, the late John Traina, was a winegrower and vintner in the Napa Valley for many years.  Trevor is a longtime collector of photography and contemporary art.  He is also a winemaker and owns a vineyard in the Napa Valley.

TNVR Trevor, it’s a great pleasure to talk to you about your projects, your passions, and your next great concept. This has been a very lively and inspiring and successful year to date for you. You and your Junior Committee recently raised hundreds of thousands of dollars for the Fine Arts Museums of San Francisco with the mid-Winter gala. You continue to launch and guide and fund innovative tech companies. You’re launching an innovative and talked-about new company, If Only (  What is it?

TDT  Thanks, Diane.  IfOnly is about making the impossible possible.  We live in an age of experiences.  Ten years ago people cared about things – from new homes to silver frames.  Now we care about the photo that goes in the frame, the rare and special experiences we have, learning from experts, and the memory that is created.  I saw an opportunity to offer consumers rare and private experiences that benefit great causes.  Who wouldn’t want to cook with a noted chef like Alice Waters or hit balls with Andre Agassi? 


TNVR Thanks to your diligence and work and research over the last twenty years, you are now successful and knowledgeable in many fields of endeavor.  You and your associates are in a unique position to create and launch, a site that offers experiences for individuals, with donations going to their selected charities.


In the Napa Valley you are offering one-on-one access to top chefs like Christopher Kostow in The Restaurant at Meadowood, and an insider visit to Darioush winery. You will arrange tours of BOND or Colgin or dinner with a Michelin-rated chef. There’s also the delicious experience of making chocolates after-hours at the great Woodhouse chocolate company in St. Helena. Golf with Greg Norman, tennis with Andre Agassi, and wine curation with leading sommeliers are among highlights. What was your inspiration?


TDT  My wife and I actively seek a life of experiences.  When I knew I wanted to propose to her, I didn’t just drop to one knee with a ring.  I flew to New York and convinced Linda Fargo, the fashion director, to transform a petite and glittering salon at Bergdorf’s  into an after-hours magical grotto with a bower of flowers and culinary treats just for us.  That memory is more valuable than any bauble I could have procured.   Alexis arrived to a scene that had been created just to enrapture her.


We have had Thomas Keller cook for us at our homes in the Napa Valley and in the city.  As a couple, we dream up superb experiences and meetings and places, sometimes for the enjoyment of our friends. I already live that life with privileged access but really wanted to offer it to others as well.  Many of our customers and members and participants on the site are sophisticated and capable of inventing great memories of their own but are busy and otherwise focused.  So, does the work for them so they never have to say “IfOnly I had tried this or done that.”


TNVR Your ‘higher purpose’ concept for IfOnly is that part of the fee for each ‘expert’ experience will be donated to the charity/cause of choice. What is this concept and how does it work?


TDT I am very passionate about giving back, helping others, making a difference. In the case of, luxury is helping others.  A portion of every transaction on IfOnly goes to charity.  We are averaging over 65 cents on the dollar and have generated hundreds of thousands of dollars for super worthy programs like child hunger, education and land preservation.


TNVR You are now in the same league as many of the top investment and start-up figures in Silicon Valley. Before your two decades in the business world, what were your education and its focus?  What was the groundwork for your fast rise is the fast-moving tech sphere?


TDT It is a bit ironic that I work in tech, as I have never been an early adaptor of technology.  I remember after selling my first company to Microsoft, I was trying to make a spreadsheet work and failing miserably.  I was at the Microsoft Headquarters in Redmond, Washington. I remember saying, “Wasn’t this software invented here?  Isn’t there someone I can call who can explain it to me, for God’s sake?”   They provided the expert.


That said, it was a childhood dream to have my own company.  I attended Princeton and then Oxford and Berkeley for graduate degrees.  It was while I was at the Haas School of Business that I discovered the Internet and realized I had better figure it all out since that was where the opportunity was.  Five companies later I am still here starting companies and most of my friends who have come up through the ranks are now running other companies that are changing our lives.


TNVR Your first executive position was at Seagram’s and you dreamed of a high-floor corner office in the iconic Mies van der Rohe skyscraper in the heart of New York on Park Avenue. What were the key learning experiences and concepts you took away from that heady start?


TDT  I was indeed at Seagram.  I really owe it to my Dad, John Traina, who made a couple calls and before I knew it I was interviewing with Edgar Bronfman, Jr. in his amazing corner office.  He had just bought Tropicana juice and asked me if I wanted to move to Bradenton, Florida.  I had really hoped for a job but had to shake my head no.  A couple weeks later I got the call and was offered a one-year position as a Marketing Assistant in New York.  Prove myself and I would be promoted I was told.  A year later I was a Brand Manager and was learning every aspect of how to shepherd a brand- from promotion to pricing to how to entertain a distributor.  It was a true leg up for me when I entered the tech world to have such background, exposure and skills.  I had a secretary, and an alcohol expense account and all the trimmings.  It was very ‘Mad Men’ save for the fact that I was officed in a much more non-descript building on Third Avenue with most of the company. While I went there for meetings and other matters, I never had an office with the senior execs in the Seagram Building.


TNVR You returned to San Francisco just as the tech world, with all its promise and possibilities, was soaring.


TDT  I knew I wanted to do my own thing and all the opportunity was in the Bay Area.  My grandmother admonished me for leaving Seagram.  I can still hear her saying – “You will never make more money than you are now…”


Today, of course she is happy to refer to me as her tech grandson!  It was the early days and none of us knew what we were doing.  I was lucky that my childhood friend, Jad Dunning, who was practicing law, left his career to help me do a startup, a site that offered in-depth and very practical product comparisons, and off we were.  Three years later the company was bought by Microsoft.


TNVR Timing is everything, especially in the tech world. You’ve been fortunate to have fifteen years of solid, insider experience. What were the impetus and inspiration and goals when founding your first company, CompareNet? Did you do expensive research or did you decide to jump in?


TDT Honestly, it was scary how little I knew.  But what I did know was how to learn.  CompareNet allowed people to research products before buying in an era when researching was harder than it is today.  I am a big believer in finding pain points and fixing them.  The idea came to me when I was at an electronics store looking to figure out what kind of cordless phone to buy.  As I kneeled trying to decipher shelf codes while talking to a salesperson who probably knew less than I did I realized there had to be a better way.


TNVR  How did CompareNet play out and how did you build it before Microsoft acquired it?


TDT  We scraped together some money from friends and family members and spent two years building the company on a shoestring budget.  We finally took investment money from local VC and fellow Reserve Member Bob Ackerman as well as from GE Capital and Intel.  It took a while to figure out what we should do and the market did not evolve the way we thought, so we adapted and started linking the decision-making tools to partner websites where people could buy.  We became “what to buy and where to buy it” for electronics, computer equipment, even sports supplies.  Microsoft liked that vision.


TNVR Your planning for the sale of your company was perfection, to the second. It seemed that moments after Microsoft’s acquisition was announced, the market took a nosedive.


TDT It was clear to me that valuations at that time were way too high.  We got a great offer from Microsoft and it was a godsend.  As one of my board members put it, “Pigs get fat and hogs get slaughtered.”  I was more than happy to take money off of the table and avoid being a hog.  Many of my friends did not heed that lesson.  Watching the bubble burst was painful and taught me that no market is immune from the laws of physics.  Ironically, Microsoft had been growing like crazy, very much the Google of its day, and I expected it to be that way forever.  As part of the deal I agreed to stay on for two years and was surprised to see how bureaucratic it had become.  Just as with startups, there is a cycle with large companies as their arteries harden and I see it happening a lot today in tech.


TNVR Many different internet/tech companies hoping for investment must have approached you. I recall your discussing recently a range of the hot new companies creating a lot of buzz. Some involved fashion, others were more mass market. You’re always researching, studying, probing. Are you a target for solicitations, inevitably?


TDT  I do hear a lot of pitches and sometimes invest.  To be honest it is incredibly hard to know who will do well or not. The hot ones of this moment may not last six months. Founders leave, talent leaves, the market gets crowded, the idea fades, the energy disperses, or the talent pushes through, some good luck maintains the momentum. Chance plays a role.


TNVR Are you drawn mostly to the tech behind the sites, or the product?  Is your interest tech driven, or do you focus on the commerce side of it?



I have to believe in the idea but, at the end of the day, the people are the most important element. 

TDT  I have to believe in the idea but, at the end of the day, the people are the most important element.  I recently was pitched by a young man from England who had a new idea for an application to summarize news stories called Summly.  I invested and then introduced him to Marissa Mayer from Yahoo who is focused on improving the Yahoo mobile experience.  The next thing I knew she was buying the company and now there is a 17-year-old millionaire running around!


TNVR For some nascent and early-stage companies you are totally hands-on, and for others you’re a later-stage investor. How do you decide? Which do you prefer?


TDT  I have invested in a number of companies.  I have been CEO or president of companies I founded or co-founded and I have been chairman.  I much prefer being CEO, despite the extra workload, because it is the only way to control the experience and to have impact.  It is hard to be an investor or board member and do much more than advise or make introductions.  I like the challenge of creating companies and there is less satisfaction for me in purely advising.  I have now founded or co-founded five companies and that is my real joy--starting with an early success with CompareNet, which was sold when I was 31.


TNVR Then in seemingly rapid succession you founded DriverSide. What was the focus?


TDT  Indeed.  My uncle was the CEO of Volkswagen and I grew up loving cars.  I noticed that all the websites were for buying or selling cars.  However, we don’t really buy that often.  What we do is own, operate and maintain our cars.  Nobody was helping with that, hence DriverSide, a website on the side of the driver.


TNVR  Are we in a Golden Age for founding certain kinds of tech companies?


TDT  Without doubt.  There is abundant capital, lots of talent to hire and more platforms than ever, from mobile to social to the Internet, upon which to innovate.  In the World of tech, no idea is too far fetched these days and anyone with a dream and some skills can find work.


TNVR Your private art collection is exciting and exceptional. You live with it at your San Francisco residence, part of which is a series of galleries devoted to photography.  You’ve been collecting significant art since you were a teenager. You’ve amassed a splendid collection of Western Art, now on your office walls.


TDT I grew up in California finding arrowheads in the vineyards and developed a love for Western Art.  My mother kindly offered to buy me a painting as a graduation present from college--an offer she grew to regret as my tastes developed quickly.  We ended up with a picture from Christie’s that broke some sort of record and I was able to add a few more to it.  They are pictures I still love but in the end I realized I simply did not have the budget to build a great collection of Western American art. I love it and live with it, but now I am more diversified.


TNVR You are involved with important new photography. You even built the new light-controlled subterranean galleries into your San Francisco residence for your collection.


TDT I absolutely love photography.  It is modern and youthful and the masterpieces are still available and mostly affordable.  Unfortunately my walls are filling up and I think my wife fears we may soon be featured on that “hoarders” show.  I started collecting mid-century black and white pictures by Robert Frank and Diane Arbus and then became more interested in the pioneers in color photography and how we got to today’s state of affairs when every artist uses photography in some way.  I do have iconic pieces like vintage prints of Arbus's identical twins and Eggleston’s red ceiling but I also like selecting less well-known works that speak to me.


TNVR  You’ve also found rare and large-scale photography--Sugimoto portraits, for example--displayed to great effect in all-white rooms that are starting to feel like an elegant private museum.


TDT That’s nice of you to say.  I wish I had more of a museum endowment or at least could charge admission!  Just joking. I love to show it to friends and collectors and museum collectors. I have a weakness for larger color works and collect artists like Thomas Struth and Jeff Wall.  I am crazy about Andreas Gursky but a couple of mine are ten feet tall, which limits the possibilities a bit.


TNVR Trevor, you’re involved with many fundraisers in San Francisco and in New York.


TDT  Indeed.  I am a bit overextended but it does keep life interesting.  Currently I am on the board of five non-profits, primarily in education and the arts.


TNVR Your charity and fundraising work has always been wide-ranging, including many years supporting Venetian Heritage. What was your earliest involvement in charity work?


TDT  I grew up in a highly charitable household.  My stepfather, Al Wilsey, was a wonderful man and very philanthropic.  And, my mother is a fundraising dynamo as well as supremely generous.  She headed up the capital campaign that raised over $200 million to build the new de Young Museum. She’s currently raising funds for a new San Francisco medical center. I really learned first from them.  After college, when I was starting out in New York, I was a co-chair of the Museum of the City of New York’s Mid-Winter party which was the primary fundraising party for the young group.  Teddy Roosevelt’s great grandson and I were the youngest members of the committee and were constantly being sent up very tall ladders to hang bunting in the rotunda and other critical pre-party jobs.  I think I licked 1,000 stamps a year and it was hard work but I learned a lot about how charities work--and the importance of self-adhesive stamps.


TNVR With a vast array of potential worthy causes to support, you are focusing on education, the art world, and medical research.  You’re a trustee for the Fine Arts Museums of San Francisco, and founded, with friends, the Mid-Winter Gala, which has raised millions for the museums. What are your on-going efforts to improve education?


TDT  After selling my first company, I vowed to do something significant to help others.  I wanted to improve educational opportunities and had met a group of Dominican Catholic nuns through my mother who had built them a gym for one of their schools.  I investigated their inner city schools throughout California and realized they were really helping many kids who otherwise would have no chance in our public educational system.  The problem as I saw it was that the Catholic church was going through a tough time and could not be relied on to give consistently to the cash-starved schools.  So I gave a gift to start an endowment and helped them raise what became $8 million to support the eight poorest schools.  The program is called Vision of Hope and it is going strong.  Since then I have been on the boards of my business school and my grade school where I currently serve as Chairman, as well as the Art Museum at Princeton.  They are all making a difference and it is fun to be able to help them.


TNVR Tell us about your very business-like approach to charity giving and funding, and using business techniques and planning for funding education programs, for example.


TDT  I always approach problems in practical ways and I hope I help the organizations I support in the same way.  At the Fine Arts Museums, I had the opportunity to start the Junior Committee to run a Mid Winter fundraiser very similar to the one I had left in New York.  It has not only brought in a lot of money but also been quite the Farm Team for new trustees, particularly from the tech world.  Also, being the practical person I am, it bugged me that visits to the de Young and Legion of Honor, our facilities, left me wondering what were the don’t-miss masterpieces.  “Why don’t we give people a little help and offer a card with the top images on them?” I asked the curators.  They obliged and now visitors can benefit.


TNVR Trevor, you grew up spending weekends in the Napa Valley, and you now enjoy a vibrant family life there on weekends and in summer. Alexis is the Creative Director for Swanson Vineyards, and you and your family own vineyards in Oakville and Rutherford. You’re a member of The Reserve.  And you still recall the days, perhaps three decades ago, when the Napa Valley was purely agricultural, with perhaps one good restaurant and few wineries.


TDT  I really grew up here in Oakville and just love it.  When I was a boy, the Oakville Grocery was a general store where you could buy provisions and there were two or three very casual restaurants in Yountville. I knew The French Laundry way before Thomas Keller acquired it.


TNVR  Tell us about some of your favorite restaurants in the Napa Valley—for a family celebration, and for a romantic evening.


TDT Well, I met my wife at Bistro Don Giovanni so that will always be special.  We love Bistro Jeanty, particularly for a hearty winter meal with friends as well as the Rutherford Grill.  For romantic or special nights we love The French Laundry or The Restaurant at Meadowood.  To be honest we sometimes do the Laundry at lunch because it is the same great menu and we have a few more hours after to digest all that great food.


TNVR Favorite Napa Valley wines for special occasions.


TDT  It is a bit of a cliché but we drink a lot of Swanson.  I learned early that when one has a wine and one’s wife has another you serve hers!  For special occasions I have a weakness for Harlan Estate.  We also like Caymus and PlumpJack, our neighbors.  And we serve a lot of Reserve wine. I have to say that or Philip Norfleet would kill me!


TNVR Trevor, on that note, we raise a glass of The Napa Valley Reserve 2006 and wish you continued success, discoveries, and adventures in the tech world.


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