Trevor Traina and the Art of Starting Over

In 2008, Trevor Traina drove an Audi R8 through China to promote a website about owning a car. DriverSide offered help with maintenance, repairs and the financial indignities of keeping a vehicle. A rally across China was an extravagant way to introduce a virtual garage. It was also a fairly good introduction to its co-founder: practical questions, conspicuous curiosity, a taste for the occasion.

Cars occupied a place in his life beyond the spreadsheet. His collection included a 1971 Ford pickup and a 1957 Alfa Romeo Giulietta Spider. His wardrobe admitted pocket scarves and cufflinks, and a blue blazer given to him by his father. The combination puts some welcome wrinkles into the familiar picture of a San Francisco technology founder. Traina could be interested in the cost of a repair and the pleasure of the machine requiring it.

The road eventually led to an ambassador’s residence in Vienna and back to a business building digital wallets. Along the way, he kept finding things people wanted to do, then working on the obstacles between wanting and doing.

A garage on the internet

DriverSide began in 2007 with three founders: Traina, Jad Dunning and Adam Jackson. The consumer website opened in June 2008. Traina was its founding chairman and early CEO; by the company’s July funding announcement, Dunning was identified as CEO and Traina as chairman. It was a shared undertaking, with a proposition that gave the team plenty to do.

Buying a car already had an online audience. Owning one meant years of less glamorous questions. What should this service cost? Which mechanic can help? Is that recall relevant? How much money should be set aside for upkeep? DriverSide gathered information around the particular vehicle a person owned, rather than leaving the owner to assemble an answer from scattered pages.

Its tools included maintenance guidance, mechanic questions and information about service and parts costs. A virtual garage made the relationship personal. Software acquired a use beyond the moment a buyer compared two shiny objects. There was work to do after the keys changed hands.

The company was sold to Advance Auto Parts in 2011. For Traina, it joined a growing list of ventures that reached a larger organization. For a driver facing an unfamiliar bill, the original idea was agreeably modest: arrive at the counter with a little more knowledge.

A business-school idea meets Microsoft

Traina had approached that problem of knowledge before. In 1996, while studying at Berkeley’s Haas School of Business, he co-founded CompareNet. Online shopping was growing, but finding a product did not necessarily mean understanding it. CompareNet organized the information that helped a customer decide what to buy and where to buy it.

When Microsoft announced the acquisition on March 4, 1999, the service had more than 1.5 million unique monthly users. Its database covered over 40,000 products in nearly 100 categories. The company employed 40 people. Those numbers describe a business doing the rather unromantic work that makes a new medium useful: collecting details, making them comparable, helping someone choose.

Before the internet companies, there had been Seagram. After Princeton and graduate study at Oxford, Traina worked in beverage marketing in New York. He has described brand management there as an education in running a business, encompassing packaging, pricing and promotion. The product changed when he moved into technology. The need to understand a customer travelled well.

His subsequent companies also took different forms. He founded enterprise-software company SchemaLogic and chaired StepUp Commerce, which Intuit acquired in 2006. A career can look remarkably consistent when reduced to a list of exits. Up close, these were different customers, products and reasons for opening a browser.

When the purchase was an afternoon

With IfOnly, Traina turned toward something harder to put in a shopping bag. The marketplace sold experiences involving people from food, sport, music and other fields, with a portion of the proceeds supporting charitable causes. It publicly launched in 2013. An introduction, a lesson or a particular afternoon could become the thing someone bought.

The offerings did not all require an extravagant budget. Early coverage described a signed guitar pick from Third Eye Blind’s Stephan Jenkins priced at $35. The business used fixed prices, rather than relying entirely on the suspense of an auction. It also had to consider the people on both sides of an encounter. Access is a more delicate product when the inventory has a diary and opinions.

“People are hungry for experiences.”

Trevor Traina, 2013

In April 2018, IfOnly announced new funding led by Mastercard and appointed John Boris to replace Traina as CEO. Mastercard later acquired the business. The handover matters: Traina’s diplomatic chapter involved leaving an operating role behind, with somebody else responsible for the next set of decisions.

The address his grandfather knew

For a change of occupation, the Austrian ambassadorship had an unusually familiar setting. Traina’s grandfather, Wiley Buchanan, had held the same post. Austria was the first foreign country Traina visited as a child. He stayed at the ambassador’s residence and watched his grandfather work.

When he appeared before the Senate Foreign Relations Committee in March 2018, the family connection supplied a gentle joke. His grandmother had just turned 100. Confirmation would make her both the wife and the grandmother of an ambassador to Austria. Few families can produce that particular seating-plan complication.

President Donald Trump appointed Traina, who presented his credentials on May 24, 2018. His service continued until 2021. In his nomination testimony, he connected the job to experience managing people and setting priorities, while discussing opportunities for technology and cultural exchange between the two countries.

His entrepreneurial interests remained visible in Austria. He later described organizing programs that brought technology leaders into contact with local founders. The relationships continued after the posting, through mentoring and investments. Diplomacy added another set of connections to a career already built through repeated collaborations.

The photographs did some of the talking

Traina took more than fifty works from his photography collection to Austria. They appeared in his diplomatic surroundings and in exhibitions. Representing a country involves finding ways to convey more than one person’s account of it. Photographs gave him other eyes, other streets, other domestic arrangements.

He has described looking at individual prints for hours, teasing out details and wondering about the people or places inside them. His question was often personal and quite specific: what might be happening behind a window, or how an image altered his feelings. The collection gave him something to keep investigating after the purchase.

“I like photography that makes me see the world in new ways.”

Trevor Traina, 2024

Christie’s presented photographs from the collection in 2024. They ranged across post-war documentary work, the development of color photography and contemporary explorations of identity. Artists included Diane Arbus, William Eggleston, Cindy Sherman and Tina Barney. The range makes a useful antidote to the idea that collecting is simply finding a category and buying more of it.

Eggleston’s Red Ceiling held particular significance for Traina, both for its visual force and its place in the acceptance of color photography as art. Here was a familiar room made difficult to overlook. Collecting and building a company are different activities, but both can begin with noticing something that other people have walked past.

Back to the problem of getting in

After Vienna, Traina returned to entrepreneurship with Kresus. Its consumer wallet addressed the difficulty of using digital assets. The company now describes a wider business, with infrastructure for institutions alongside tools for individuals. Its current leadership page lists him as founder and CEO.

In May 2026, Kresus announced a collaboration with Canton Network to help organizations move blockchain applications into production. In July, it announced an inheritance-planning service for wallet users. The subjects are less picturesque than a rally car, but they bring his work back to practical questions of ownership, continuity and access.

He also joined Tools for Humanity as chief business officer in January 2024, working on the company’s international expansion. Its World project addresses the question of distinguishing people from bots online. During a July 2024 interview in Austria, he discussed both the logistical task of expanding the project and the privacy concerns surrounding it. A product can require an explanation before it requires a sales pitch.

There is an amiable thread running through these changes. Entrepreneur Ben Casnocha, writing about Traina in 2006, remembered someone kind, funny and goofy, without the social armor he sometimes encountered in Silicon Valley. That recollection gives the formal titles a little air.

At Haas, he also described a discipline for making decisions: gather people’s views before announcing his own, write down what they say, then communicate the choice. A founder can spend years developing conviction and still need to learn when to keep quiet. The method gave his colleagues room to supply information before the boss supplied the answer. It is a small piece of management advice, less entertaining than a story about an acquisition, but easier to put to work on Monday morning.

Returning to Haas in 2025, Traina spoke about reinvention and the need to keep learning. Asked what he would do with an extra week, he chose family and close friends. For someone whose working life offers so many potential next chapters, it was a rather definite answer. Even the most interesting diary needs a few afternoons that nobody has to acquire.