Boston’s biggest consumer tech success story, TripAdvisor, was founded back in 2000 by Stephen Kaufer, Langley Steinert and Nicholas Shanny. The trio has had quite the journey, both individually and as a team.
Kaufer has remained glued to the travel giant since inception, Steinert left in 2006 to start another Boston consumer tech powerhouse, CarGurus, and Shanny has been a part of both… and more.
Shanny, now SVP Engineering and Operations for TripAdvisor, originally met Kaufer in the late 90’s while the two were at Centerline Software, where Shanny spent two years as an engineer. Prior to Centerline, Shanny, a native of Madison, Wisconsin, founded a software company that helped automate manufacturing plants.
“I learned a lot of lessons with that company, including going into business with friends – make sure legal agreements are in place versus a handshake.” Shanny reminisced about his parting from the company.
After leaving Centerline he went to work for Microsoft in Seattle, focusing on applied research and building internal tools and products. Then, in the fall of 1999 his friend and former colleague, Kaufer, called him with an idea about a travel site.
“The entrepreneurial bug had been scratching me for a while and I liked what Steve had to say. I was in and it wasn’t a hard sell for me.”
While the founding team, which also included Thomas Palka, was originally spread out around the country working on the initial concept, they eventually landed in Boston to formally launch the company. Their first office was above a pizza joint, Kostas, in Needham, MA, the town the company has recently returned to with a new, massive, state-of-the-art headquarters.
The story of TripAdvisor is well documented. The company was acquired in 2004 by IAC then spun out from Expedia as a separate company in a 2011 IPO. The company has continued to be a pillar of the Massachusetts tech sector.
Shanny’s story, however is a much lesser known tale. As the engineering talent of the founding team, Shanny has always viewed TripAdvisor as his “baby;” understandably so. However, Shanny spent some time away from the company he helped put on the map.
In 2007 his former co-founder, Steinert, recruited him to help get his new venture, CarGurus, off the ground just a year after Steinert launched the online auto shopping business. After two years with CarGurus and the company in a good position to take off, Shanny was ready for some time off.
“I left with every intention of taking time off to travel and race cars,” Shanny told me inside TripAdvisor’s new complex.
Yes, Shanny is a long-time racer of souped-up Porsches; travelling the country racing cars both competitively and recreationally. What started as an instructor role now has him driving all over – racing at the likes of Waltkins Glen and New Hampshire Motor Speedway. His most notable competition is the endurance race, 24 Hours of LeMons, a low-cost endurance racing series.
“It’s an amazing experience - Full of adrenaline, but also an incredible escape. Coming from a business environment that is so fast-paced and competitive to being behind the wheel hyper-focused on nothing but driving for two hours is exhilarating. It’s a rush.”
Shanny's passion for racing is obvious and refreshing. It’s his release from his truest passion, TripAdvisor.
His plan for a racing-filled hiatus from the business world, however, was halted by another travel venture. Once again came a proposition from Kaufer, who asked Shanny to take a hard look at SmarterTravel, a recently acquired company for TripAdvisor.
“I was hooked pretty quickly. It was a very interesting challenge and another opportunity to build, grow and mentor a new team of engineers, which I love.”
Almost three and half years after heading up engineering for SmarterTravel, Shanny came full circle and returned to TripAdvisor for the very reason he got on board SmarterTravel – a new challenge and opportunity to grow a team. Plus, of course, this was his baby.
Back on board TripAdvisor, the company and brand he helped launch and grow, Shanny was brought in to fix the vacation rental division, which involves focus across many geographical locations.
Shanny talked further about the specifics of the challenge that enticed his return:
“TripAdvisor needs to continue evolving its technology. We need to make sure we’re growing from technology perspective as well as a people/talent standpoint to support the demands of the marketplace. We have the opportunity to help transition the industry and I was given the challenge of building a team to tackle that.”
As with most tech companies, TripAdvisor, and Shanny himself, are always seeking top talent to evolve their technology and continue innovating. Shanny talked about the data challenges and different spaces the company is looking at as intriguing opportunities for engineers out there. However, there was one opportunity he talked at length about that also stood out to me – the chance to be involved with a consumer tech brand with their level of scale and reach on the east coast. Something that is unique to TripAdvisor.
Shanny expanded on this by saying the company puts a lot of responsibility on their employees, but most importantly, still operates with the attitude they set way back in Kostas’ in 2000 - “get to market fast.”
“We had an agile, fail fast mentality long before it was the norm, or even talked about at all. We’ve continued this thought process through to our present day. And for a company of our size, with so many areas for developers to be involved with, that’s pretty exciting.”
(Cover photo credit: Shutterstock)