Why Trippy is a Giant Failure and How Crowdsourcing Can Improve Travel

Trippy's logo, a crowdsourced projectPicture this. You’re preparing to go to London, someplace you’ve never been. You bought a guidebook, but those get dated fast, so beyond the typical tourist attractions listed, you aren’t sure what information is accurate and current. So you go online, log into a website, post your trip itinerary, and said website connects to your Facebook and Twitter accounts. Now your friends can leave suggestions about what to see and do and where to eat. Armed with this list, you’re now prepared to see London.

Or maybe you land in London, open up an app, and follow the same process.

Either way, you have crowdsourced information from the people you trust the most: your friends. Your friends might not be travel experts, but they know what you like so when you ask, “What’s a good place to eat in London?” chances are they have a good suggestion for you.

That’s exactly what Trippy does. Or, should I say, is supposed to do.

When Trippy came out months ago, I could barely contain my excitement. This app did exactly what I described above. Revolutionary! I thought to myself. This is going to change how people get travel information. A new service that allows you to bring together your social networks, easily get advice from friends, and share your trip was exactly a service people would use. It was brilliant.

I get pitched dozens of apps each week, but I thought this…this is something I would use all the time! It definitely filled a void in the market. The introduction video was amazing:

So I eagerly signed up—and found I couldn’t do half of what was promised. No big deal. Trippy was still in beta, and I’d let it work out the bugs before I made my final judgment. Let them add the features and straighten things out. I know apps and such are never perfect on day one.

But months went by, and I heard nothing more. There were no blog posts about Trippy, no annoying PR emails in my inbox about the service, no big marketing campaigns, and no articles on major magazines or websites. Heck, Tim Ferriss is part of the board, and even he had no blog post about it! Trippy just seemed to fade away.

Then a few weeks ago, Trippy had a huge relaunch. They announced their official advisory board, which consists of a whole lot of big-name writers, tech people, celebrities, and social media folks. It’s a powerhouse board, but the real news in their announcement was they said they were going to create a Pinterest-style site. When I read that, I was gobsmacked.

I took a break from writing my book, downloaded the latest version of the app to my phone and said, “Well, maybe I missed the big updates.”

Logging into trippy.com, my home screen looked like this:

The Trippy home-screen that looks like Pinterest

I was confused. Why am I looking at Pinterest? I thought. Where are my friend’s trips? Where are mine? OHHH! I finally see them—hidden in the top right corner in a drop-down menu so as to not take away focus from the boards.

Next, I opened up my app to find…nothing. Sure, there were a few changes, but I still can’t:

1. Connect to Twitter via the app to tweet. (You can do it on the website, though.)
2. Tag people in photos.
3. Find my friends via Twitter, Facebook, or Foursquare and add them to my friends list.
4. Check into places on Foursquare.
5. Have a default newsfeed for my friends’ trips.
6. Book hotels directly like the video says I can.
7. Create a profile and add friends of friends (i.e., like Facebook).

While on the website, I can tweet and share my trips on Facebook, but it’s not automatic. I have to do it manually. I think there should be an automatic setting that lets my friends see my trip similar to how Pinterest is integrated into Facebook’s newsfeed. Moreover, I have to manually ask friends for help on Facebook. But I can only do that on the website as there’s no integration on the app. And, they can’t give me advice unless they’re signed into Trippy. Most people aren’t going to join a new service out of the blue. People should be able to leave comments on trips made via the website. (On the app, I can see a case for just having it made available to signed-in users.) The app and site just seem to still be in some perpetual beta.

Now, I like Pinterest. I don’t use it, but I get why it’s popular. It’s a good service to share pretty photos, fashion, recipes, and home décor. It collates pretty things into one place and everyone loves pretty things. Win-win. And with its amazing Facebook integration, it’s here to stay for a while.

But Trippy isn’t Pinterest. It shouldn’t be Pinterest. I loved Trippy because it was a social planning website. That was something I needed. It should be what that amazing video says it was going to be. Outside of about 25 dedicated travel writers, I don’t know anyone who uses Trippy, which is a real shame. If it had stuck to its original mission, fixed those bugs, better integrated itself into Facebook, and let me finally tweet, search for friends, and share photos, I bet a ton of people would have signed up for it.

After all, studies have shown recently that around 30% of people use social media to get trip recommendations. Trippy was supposed to make that process easier.

After playing around with Trippy, hoping I was just doing something wrong, and realizing I wasn’t, I deleted the app from my iPhone with a heavy heart. I mean, I was so excited about Trippy when it came out that I was sad to see it fail. But Trippy seems to want to move away from the crowdsourcing aspect and become simply a Pinterest for travel, not a trip-planning site for friends.

Crowdsourcing is the way of the future

In my mind, Trippy failed because it strayed from its original (and awesome) mission and because it was poorly marketed. (I bet most of you have never even heard of Trippy.) Trippy tells me only 27 of my 1200 Facebook friends are connected to it. Most of my friends are a travel and tech-savvy bunch, so I expected a lot more to be on. In fact, I bet a large portion of my friends would sign up if they knew about it, as they tend to be hardcore travelers.

But a crowdsourcing, social-planning travel site is only as good as those using it. And frankly, not a lot of my friends are using it, and they can only comment on my trips if they join. But why join a network that has no one you know on it?

Even though Trippy is a failure, I think there’s a huge future in crowdsourcing for travel. There are a number of other sites out there (Gtrot is a good one, but that site needs to make itself more social and have a mobile app), but I think Trippy had the best idea and goals. It just lost its way. There’s nothing wrong with making a travel site photo heavy—travel is very visual. But instead of making Pinterest, they could have made the photos in the trip-planning area bigger. Look at how tiny it is:

Tiny Trippy screen that is hard to read

Wouldn’t time and money have been better spent making that look better?

In the age of the Internet, people get ideas the way they used to before big advertising: from friends. Why listen to an ad on TV or in a magazine when you can log onto Facebook and ask your buddy who suddenly moved to London if something is good or not? Or email a blogger and say, “Matt, I know you go to Thailand a lot, what are your recommendations?” Or ask Aunt Ida what the name was of that good sushi restaurant in Japan she ate at.

I never use guidebooks when I travel now. I ask people online for food and hostel recommendations. My friends know my tastes.

Social media makes it easier to reach out to friends and get recommendations for everything related to your trip. There are so many social networks out there that having one place that connects them would be very useful.

A program that does that will fill an incredible void. Being able to open an app, create a trip, automatically share it, allow people to comment, book reservations right there, and overall, do exactly what that video above promises will be the next big thing. But when you create too many steps and too much clutter, you give people less incentive to do more than just post a status update on Facebook asking where they should stay in Paris.

A website/app that lets you easily crowdsource travel information can succeed and become popular with the public.

So long as it just sticks to the goal of connecting friends and travel.

  1. I’d never heard of Trippy, but original Trippy sounds like it had tons of ideas… well, seeing as it’s gone in a new direction, that could be a wee project for you? 😛

  2. (WARNING: rant below)

    I’ve followed Trippy for several months (mostly because our site offers something vaguely similar) and they definitely dropped the ball on a few things:

    >>> Poor usage of images (your screenshot says it all)
    >>> Lack of real content
    >>> A failed attempt to “piggyback” on existing social network sites.

    But their biggest mistake is failing to include unique, valuable content for their users.

    I agree Crowdsourcing can be a great method for travel… but at some point web owners must realize that publishing their own CONTENT is a good thing.

    It’s content that keeps you coming back for more…

    It’s content that builds trust with your users…

    And it’s content that gets ranked in search engines, shared on social networks and ultimately drives sales, links and revenue to your business.

    Why haven’t people figured this out?

    I mean, damn, that’s why guidebooks got popular in the first place… they created valuable, unique content for their users.

    Now it’s suddenly cool to “program” a travel experience. Don’t get me wrong: technology has its place in the travel market (book tickets, compare flights and/or hotels, etc.) but at the end of the day…

    … WRITERS rule the travel market. Always have, always will.

  3. Michael Glass

    Firstly let me say that I love the new site design (it’s been a while since I have landed on your site so I apologize if you have had it up for a while).

    As for Trippy I was in shock also when I read the Tnooz article about it’s Pinterest style layout. The original idea did seem ok but the issue I have is that my social connections may not have been to the places that I want to go. Not to mention the fact that I have to post a question and wait for replies.

    #Blow your own horn moment#
    We have been working really tirelessly at creating a travel community site that is rich in content but allows the user to discover and get answers without the need of this question and answer scenario.

    That’s all I will say for now cause I’m not a big fan of comments that try to divert all the attention to their own projects. I guess you will just have to wait and see what we have to offer and decide for yourselves.

    A final word on Trippy – they really dropped the ball in my eyes when they didn’t respond to any of the critcism posted in the Tnooz article that I mentioned earlier. At least Gary Ardnt (an advisor to Trippy) stepped up to the plate for them.

  4. Agreed that Trippy’s pivot is a bust. There are, however, some alternatives in the category. Gogobot is the most popular, although it’s certainly more manual to supply content there. Tripbirds just launched and seems to be focused on social as Trippy v1 was. Still no clear winner here, but there’s certainly a big opportunity to be the next version of TripAdvisor or VirtualTourist.

  5. Another one to watch is Wipolo, who is very well integrated with Facebook + has automatic trip import like TripIt (just forward your booking emails to synch trips). And has mobile.

    I think the Trippy story is a simple monetization problem. Great idea, good funding, do the first step (MVP), then what… not enough traction, no revenues, investors get nervous, and all of a sudden here comes “photo curation” as the new popular way of doing things. Pivoting is a hard decision but it’s undertandable.

  6. Interesting piece. And thanks to those in the comments so far that cited the original Tnooz article about the Pinterest pivot.

    I would only say that to suggest something is a “giant failure” implies closure of the business, rather than trying something else.

    Trippy is like many, many startups which evolve from one idea to another, until they either get traction or shut up shop.

    To give Trippy its dues, it is simply following a well-trodden path in startupland.

    Whether the switch and execution of the pivot works out will certainly be interesting to watch.

    At the end of the day, consumers will probably not care at all about its similarity to Pinterest or change in focus from the one you enjoyed in its early stages, if they still get value out of it.

  7. Hey Matt. I owe you an apology. As a big early fan of Trippy, i should have reached out to you personally and done a better job explaining how/why trippy is evolving. That would have given me the chance to address every one of the concerns you raised above, because they ae all on the roadmap… and some will be live soon. We’re a small team working our asses off to build what our users want… and since launch, the single most requested feature on Trippy was the ability to browse and be inspired. We wanted to let people start playing with it asap, but what you see now is only the beginning. We didn’t take anything away from what made trippy great the first time you used it… we just moved it around to allow people to “dream” a little bit before they use Trippy to actually “do” their trip. That’s my attempt to plug what might become our new marketing language… from Dreaming to Doing. Email me if you want to dive into more details. Sorry we lost you aleady… good luck and keep traveling man!

    • I will begin by first cautioning that I’m not savvy on tech news. I think there is some merit on the dreaming, laying the ground rules on what you like before asking for tips. The answer I’d like to hear from anyone giving advice isn’t “You should go here”, its “First tell me what you like and what you’re like, then I would suggest…”

      Of course this can lead to clutter and possibly a lot of vague statements. That will need some managing. i think through Matt’s blog and projects he’s been able to define himself well so he can accept direct advice. The pivot seems logical to me but that’s only the beginning still…

    • NomadicMatt


      Thanks for the comment. I like your “dreaming to doing” logo but I feel there’s less emphasis now on the doing and more on the dreaming. I’d say Trippy would be great if it was more doing. (Another good thing: See via Foursquare integration where everyone of my friends are!). I get start ups evolve and change over time, especially when you have a small team. After all, I’m a team of one so changes don’t always happen at once.

      I’m not swearing Trippy off forever, just in its current iteration, I am not a fan.

      I’d love to talk more and I know we will both be at TBEX! (Looking forward to meeting you!)

      • Features cost $ and time but the site needs to bridge this gap between the ‘dreaming’ and ‘doing’ tools.

        The Board’s serve their purpose but the trip planning tools, particularly the ‘Itinerary & Saved Places’ page, is painfully manual. One feature: allow user’s to choose from his/her ‘want to’ boards when added places to an itinerary would be a big improvement. Maybe something like the facebook friend’s list editor here http://www.zeropaid.com/wp-content/uploads/2011/10/facebook-friend-list-e-300×285.png

        That one change along with maybe more reliable address/phone info in the Board listings and Trippy would be back on my rock-star-apps-can’t-wait-to-bug-all-my-friends-into-joining….list.

  8. NomadicMatt

    Good discussion here. I should say that I think there is nothing wrong with start ups changing. This is is nothing like it was back in 2008. That being said while aspects of my site have evolved, I’ve stuck to my original mission. I’m OK with Trippy changing but it seems that the original mission of “social travel planning” has shifted and too me, that is a real shame because I think the original idea was very solid.

  9. Start ups must change… especially early on.

    With my travel website, we literally spent six months just on layout. Then we had beta testers hammer away at it and make suggestions.

    Did we make changes? You betcha. Will we have to change more as the site matures. Indubitably.

    That’s a big part of startups.

    The key is to listen closely to your audience and give them what THEY want. If some people want one thing but the majority wants another, you’re probably off going with the majority.


    It seems like a lot of travel business owners (not solely bloggers) are on this thread. What challenges in travel sites do you forsee in the next few years?

    I think struggles for many include:

    Going mobile
    Gaining traction in social areas
    Creating quality content with ROI (this could be a killer)
    Finding unique ways to profit besides hotel and airfare commissions (after all, who wants to be a middleman for a middleman?)

    What do y’all think?

    • Yes, I agree with your comments. Site layout and content changes are ongoing efforts when it comes to catching up the current trends.

      There is a challenge when it comes to going mobile and finding ways to create quality travel content for better ROI. But, I would say once we build community that trust site content who gets exactly what they expect from travel sites, I think it will be much more easier for site owner to come up with ideas by directly interacting with site readers.

  10. I have friends who work at both Trippy and TripIt, and they both are fair services that are constantly being updated. I’m most partial to Gogobot (so much so that I starte doing some writing work with them), which includes the ability to post reviews, make trip recommendations, upload photos and create checkins. If you haven’t yet, give it a try and add me as your friend :)


    Good luck in Vegas!


  11. These über tech sawy travel planning crowdsourched websites seem to come and go as the wind blows. Remember gliider.com – a Webby nominee in 2010 and gone today. There are so many of them today (Gogobot, Travelmuse, Igougo, Geckgo, etc.) but to work they need to get beyond that critical mass of content (or/and users), because – as everyone else seem to acknowledge – quality content is still king!

  12. It sounds like they got too involved in making the site visually captivating and completely lost focus on the function it’s supposed to serve. I’m sure you’re right that some company will figure out how to fill this gap in the social networking sphere.


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