Testing Tripstr with Trips

Purpose of this blog

Adlai Holler and I are headed on a month-long tour of 8 cities in the USA, starting in NYC and working our way across the country towards Anchorage, Alaska. We’ll be staying in Airbnb’s, exploring cities, hiking national parks, and spending every other waking moment hacking away at the most challenging part of the Tripstr application: The Trip Builder. Our primary goal is to keep our investors and other interested parties informed and excited about our progress, and hopefully give you some insight into the product development process at the same time!


Mobile workspace #1, an Airbnb in Brooklyn.


Blog Foreward

The consumer travel space is hard. From the outside, the trillion dollar (yes, 4 commas) market size is incredibly appealing. As entrepreneurs it’s easy to take the mindset of “surely if we can just capture 1%…” But the problem lies with infrequency. The most successful consumer startups have managed to become a daily part of our routine (think Twitter, Instagram, Facebook), but travel startups only have a few chances a year to win your loyalty AND eventually convert you into $$.

The bet we’re making with Tripstr is that we’ve got the secret sauce to trigger more frequent behavior than “during your next trip”. It’s the thing that excites our investors, and that reinvigorates me every time I pitch it. The timing couldn’t be better as mobile software, advances in device sensors/battery life, and broadened international cell coverage are aligning to our advantage.

The larger vision for Tripstr is a mobile-focused travel inspiration app, where your network is your travel agent, and travel planning becomes a frequent activity, rather than a crammed research session just before leaving. The foundation for such an experience is real user trips, and the Tripstr ‘Trip Builder’ is the piece that makes such an experience possible.

Our smartphones carry all the necessary data, and with the right combination of design and engineering, your smartphone can auto-magically create a beautiful, informative, shareable travel log.

Unfortunately, the one thing that makes Tripstr so special is the one thing that has eluded us since we set off on this journey 2 years ago. But it’s not for a lack of trying…

Traveling on a budget. This small child’s room is home for the first week :)

The main problem: It just so happens that Tripstr’s Minimum Viable Product (MVP) is not very minimal.

Our first attempt, which I’ll call Phase I, launched on the App Store a year ago. We started by building an app that could uncover all the past trips sitting on your phone and turn them into beautiful photo stories with one tap. This was more challenging than we originally anticipated, and important features took a back seat while we gathered some much needed user feedback.

End result: People loved the app initially (5 stars on the App Store), but (a) didn’t get a lot out of viewing other people’s stories, and (b) struggled to use Tripstr while actively traveling, which is the exact time we should have been wowing them

We managed to bring in some revenue through licensing our backend code, and went back to the drawing board for Phase II. We flipped the focus and really nailed the while you are traveling use case, which in turn helped our small beta community feel very much alive. Simultaneously, we added a way to tag the specific places you went (bars, restaurants, etc) so that others would benefit from your experience through bucket listing places you’d visited.

End result: Engagement with the community increased drastically, but people complained about not being able to post their past trips, and tagging places was still too much work.

Enter Tripstr 3.0: Your personal travel-logging assistant.

The reality is that our Trip Builder needs to be simpler AND more robust. Outlined below are our goals for Tripstr 3.0, which we intend to have built before we arrive home in San Francisco:

  1. It should be able to handle any type of trip. Past trip, present trip, future trip, long trip, day trip, etc.
  2. It should get you 90% of the way there, and feel like magic. Just arrived at your first destination? Tripstr notifies you it has already logged your 4 photos. Visited 2 restaurants and a theatre? Tripstr already added them as part of your journal. Ready to share? We’ve already prepared a beautiful website and collage to push out to Facebook and any other network you choose.
  3. It should work 100% offline. On a cruise? Flying home from Thailand? These are the perfect opportunities to finalize your trip story.
Some concepts. Left: Knowing when you’re traveling. Middle: Your ‘Personal Scrapbooking Assistant’. Right: Auto-tagged photos from places you visit.

At this point you may be wondering why the Trip Builder is so important. Why does it matter that we get more than the typical “content creator” types posting in the app? Why don’t we just market the 5 star app we’ve already built? I’ll leave this for the topic of a future post: How the Trip Builder Completes the Viral Loop

Coming Soon…

Traveling while working on the above will force us to re-think our assumptions, uncover new opportunities, expose key problems and generally keep us focused on the end goal. Both Adlai and myself will be sharing our progress on design and engineering, as well as user feedback from people we meet along the way. Stay tuned!

— see the next post in the series HERE

— this post by Austin Cooley, Co-Founder, Tripstr