Tripshare is the first travel planning app to let users create bookable itineraries with actual dates, prices and availability for flights, hotels, vacation rentals and tours.  “Tripshare trips are more than wish lists.  They are real, and they are actionable,” said CEO and Co-founder Bob Dana.

Mr. Dana brings a track record of helping start new ventures that change travel paradigms.  He was employee #1 at Virgin America, where he wrote the business plan green-lighted by Sir Richard Branson and served as its first CFO.

Online travel offers many services for inspiration and for booking, but between them is a gap – the need to collect, organize, and share specific information before committing.  For complex trips or to collaborate with others, travel planners create draft itineraries.  Tripshare’s research shows that 55% of U.S. adults have made itineraries, overwhelmingly for leisure travel.  Yet modern tools are lacking; over half of these itineraries are still created with pencil and paper.

Tripshare is ideal for complex trips or for people who plan travel meticulously.  With Tripshare, users take control of trip planning by tapping into huge inventories of partner content via a simple, map-based interface supported by high-resolution photos and a drag-n-drop editor. It’s a professional tool that’s easy enough for anyone to use.


I thought this looked like a neat app, so I reached out to Bob Dana to get some more information.

Q. Tell us about your company.

A. Tripshare was formed in 2011 by me (Bob Dana, CEO/Co-founder) and Ken Goto (CTO/Co-founder). Ken has
since moved on and been replaced by Eric Kapke (VP Engineering and Acting CTO). Ken and Eric both come
from Apple and Microsoft, so we have a very strong technical team. Our designer was also ex-Apple. Today we
are seven in total, four full-time and three part-time.

Our company has a singular mission: to build the world’s best tools to create and share draft travel itineraries.
Our initial product, of course, is an iPad app targeted at consumers who want to plan leisure travel. We believe
about 10-25% of all leisure travel involves the need for a draft itinerary, typically (i) to manage complexity, or (ii) to
build a consensus among groups traveling together. We call this “C2C trip sharing”.

We also believe there is a large demand for our tools for “B2C trip sharing”, where small/medium sized businesses create and share itineraries with their prospective customers. This market includes travel agents, of course, but also a “long tail” of tour operators, B&B owners, vacation rental owners, and other travel suppliers that typically live in a world of responding to customer inquiries with quotes for their services. We believe (and our research bears this out) that B2C trip sharing will be a strong driver of adoption of our product.

Q. When did the Tripshare app first come out?

A. We released Tripshare v1.0 in the App Store with no publicity or advertising in August 2012, after a year of
development. It, and subsequent updates, were featured as “new & noteworthy” by the editorial staff at Apple,
resulting in about 20,000 downloads. However, feedback was clear that we needed to make the app simpler,
more intuitive, and more engaging. So we worked for seven months on v2.0, introduced two weeks ago. Early
response to v2.0 has been strong, both from consumers (4.7 average rating) and from travel industry experts.

Q. Who would you recommend use Tripshare?

A. Tripshare is for people who need to plan complex, multi-destination trips and to sort out their plans before they book. it’s also for people who travel in groups, for example friends traveling together to attend a destination
wedding or a sports event. It’s also for people who just love to plan, who are obsessed with “vacation perfection”, who are often consulted about a specific destination they know well and want a fast, fun way to share their knowledge, and people who see travel (and itineraries) as a form of self-expression. And, of course, the business users I mentioned above.

Q. What future plans do you have for Tripshare or any other app?

A. For the next few months we are focused on platform extension: bringing Tripshare to the iPhone and the web
browser (today browser-users can see an itinerary and comment on it, but they can’t yet search and create a
trip). We also expect to plug key gaps in our content such as rental cars, multi-day cruises/safari’s, and perhaps
rail transportation.

In 2014 we expect to turn out attention to building a community, especially the ability for users to search for relevant itineraries of other Tripshare travelers for ideas and affirmation. Longer term, we will add new features such as driving directions, semantic search capability, integration with personal online calendars and trip support services (e.g. Tripit), post-trip commemoration capability, and many other features.

Many thanks to Bob Dana for his time and if you doing any traveling head over to the App Store to pick up Tripshare.