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Trippy is banking on the premise that its new question and answer platform for travel will be a cut above the rest in terms of quality, and that it will distinguish itself in the way it maps attractions and concisely summarises their basics for travel planning. That begs the question: Will it be enough?

J.R. Johnson has been embedded in the trip-planning startup sector since 1999.

There may be bodies of failed startups scattered everywhere, but unlike many of his peers, he has something to show for it.

Johnson served as CEO of, a travel-planning site, for nearly nine years before selling it to TripAdvisor for a whopping $85 million in June 2008 without raising venture funding along the way.

To put that $85 million exit for VirtualTourist into context, consider that NC2 Media acquired Lonely Planet from the BBC in 2013 for $69 million, and a year earlier Google acquired Frommer’s for $23 million in cash and stock.

VirtualTourist’s acquisition yielded a relatively huge payday, but it had its very trying moments along the way, including when it had to reboot and fire most of its staff as the Internet bubble got punctured around 2000.

But Johnson either loves bumps and bruises and/or has a passion for trip-planning startups because in late 2011, about three years after leaving VirutalTourist in TripAdvisor’s hands, he founded another travel-planning startup, Trippy.

It’s a rough-and-tumble world out there in travel startup land as by early 2014 Trippy had executed its second pivot, after much “soul-searching,” CEO Johnson says, into a question and answer platform customized for travel.


Trippy this week announced that last year it picked up a Series A round of $3.5 million led by eVentures. That funding came in around the time last year that Trippy was temporarily shuttering the site to rethink the whole venture.

When I commented to Johnson that the investors must have a lot of confidence in him, he shot back that the funding was a testament to a “huge market opportunity” as travel planning is “dominated by one player,” namely TripAdvisor, the company that acquired VirtualTourist, and more significantly, hosts 150 million user reviews.

“People are looking for a new option,” Johnson says.

The chances of Trippy and its Q&A platform becoming a credible alternative to TripAdvisor are a longshot, of course. Some will even scoff at the notion.

Trippy’s Journey

Trippy’s evolution and prospects reflect some of the travel industry trends, such as social travel and Pinterest-like visual search, that have come to the fore in the last few years, and the daunting challenges facing travel startups everywhere.

Trippy’s first incarnation in 2011 was as a mobile and social travel app where users would solicit advice from friends about upcoming trips, but Johnson says growth wasn’t fast enough because users wanted more than advice from their friends, and they definitely didn’t want advice from certain friends who might have different tastes.

“It was overly structured, and not a natural process,” Johnson says.

Trippy then executed its first pivot and in May 2012 “went up the funnel,” Johnson says, offering Pinterest-influenced images to inspire travel early in the travel-planning process. When travelers worked their way ahead and were ready to plan a trip, then Trippy would access their social networks for an assist and advice.

“It was too hard to lead them down to our original, utility-based product, which is where our heart was, and still is,” Johnson says.

Second Pivot Into Q&A Platform

That led to Trippy’s second, and latest pivot into a question and answer platform for travel.

Travelers post questions like What is your favorite brunch place in SF? or Anyone have any quick day/off the beaten path trips in Europe? and then other travelers chime in.

Q&A platforms aren’t new to travel. For example, Johnson’s former company, VirtualTourist, offers such a platform, features Ask a Nomad, and there are plenty of general-interest Q&A sites such as Quora and Yahoo Answers that delve into vacations and destinations with a much larger audience.

But with even well-funded startups such as Room77 in the hotel metasearch sphere finding it so hard to compete against well-entrenched players who were much earlier to the game, how is Trippy going to get noticed in the shadow of TripAdvisor or LonelyPlanet?

Curating Quality and Problem-Solving

Trippy, as Johnson tells it, is betting on curation, quality and problem-solving.

Trippy curates travelers’ questions under the theory that “good questions get great answers,” Johnson says. Its moderators will reject questions that are overly broad, and they sometimes work with questioners on refining their queries in the hopes of eliciting better answers.

“If TripAdvisor is a Walmart of travel content, then we’re your farmers’ market,” Johnson says.

Likewise with users’ answers, Trippy will showcase some, but has another category, Other Answers, for users’ responses that may be less than insightful, and these appear toward the bottom of a page, Johnson says.

Is the Differentiation Enough?

Among its differentiators, each place or attraction that is mentioned in an answer is immediately mapped, which solves the problem of travelers trying to get their bearings in a new destination, Johnson says, and then basic information about these attractions appears underneath the map.

Place pages for each attraction display larger maps, and more detail about the basics — address, directions, phone number and website URL.

“The quality of content is how you win in this space,” Johnson says.

In a perfect world, that might be true, but competition and business realties often aren’t that egalitarian.

Even so, conceding a caveat that Trippy’s Q&A platform is only a few months old and needs development time, the quality of the content is, well, all over the map.

While you can be entertained and educated when reading How do you deal with the lack of sunshine in Seattle?, many of the questions and answers on the site are unremarkable.

Getting Travelers to Answer Questions

Trippy has to pin its hopes on building scale, and getting people to ask and answer questions. You can’t build a roster of quality answers if there is a scarcity raw material to vet and curate.

Johnson argues that users will step up and answer questions because people like talking about travel, and “it feels good if you can offer help to somebody if you are not getting something in return.”

“This is human nature stuff,” with people helping other people, Johnson says.

And, then even if Trippy is able to build a substantial following, the monetisation issue will come to the fore.

Johnson says when Trippy is ready for that stage, it will likely use third-party technology to launch a hotel metasearch product for users who are ready to book a stay.

Trippy will have plenty of company if it gets to that point. There already are tons of metasearch sites out there hungering to differentiate themselves, with trip-planning site Gogobot being the latest to attempt to build its own.

The trip-planning sphere isn’t for the faint of heart.


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Tags: ceo interviews, trip planning, tripadvisor, trippy

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