HipTraveler.com is a trip-planning startup based in Los Angeles.
Its distinctive hallmarks are its user interface, which emphasizes visuals, and its aggressive use of partner data feeds (APIs), which streamline research and booking.
Unlike most other travel sites, it aims to capitalize on the image-based and social-sharing look popularizied by Web apps such as Pinterest, Instagram, and Evernote.
HipTraveler has made a Vine to illustrate its premise. It includes Bella, a 10-week-old Labrador.
Q&A with CEO Baumgartner:
What's the size of your company?
We have an 11-person team: five who are technical, two who are executives, and four who handle marketing and business development.
Funding?
I've bootstrapped the company. We are now at a point where we are validating the concept and gaining traction. So we’ve just now started looking for the right early stage investors.
Tell us how you founded the company.
Travel planning, even with the significant investment that’s gone into the sector, is still a frustrating experience for most consumers. I felt that the current sites were lacking four major things:
- Visual design - After all, travel is a visual experience foremost.
- Crowdsourced resources - I was tired of visiting 38 sites to do research and book a single trip.
- A truly simple and functional itinerary building application – Most sites are too complicated.
- Social connections to friends, travel experts, and offline travel agent booking resources. Some are social, but none let users connect with actual experts.
It was a Herculean task to tackle all of these pain points. As you know, the travel vertical is one of the most crowded.
But starting a business in itself is brave undertaking. So I figured why not go for the moonshot and tackle the real pain points.
I think we’ve come up with a rather elegant solution. Our early adopters seem to agree. But a wider audience will eventually validate whether or not we are on to something that has mass-market appeal.
In a nutshell, we feel that itineraries are the most valuable form of recommendation and that the best way to aggregate them is to do three things:
- Making it dead simple to build trips with our Itinerary Builder application. Our Drag & Drop interface, with more than 50 million places of interest as well as a book-marklet tool for collecting on the web if you don’t find what you’re looking for on the site.
- Give travel rewards and eventually compensation to our super users, aka HipTravel Ambassadors, for creating itineraries We have a first-of-its-kind program that lets a user build an itinerary and then be rewarded every time someone else books it.
- Partner with offline travel agencies – We’ve partnered with one of the largest in California.
Our crowd-sourced itineraries are printable, shareable, and -- in a point that differentiates us significantly from the other start-ups -- fully bookable, either self-serve (via Expedia, Travelocity, Priceline, etc.) or through one of our partner travel agents.
Estimation of market size?
$257 billion, broken down as $180 billion online leisure travel commerce + $52 billion traditional offline travel agency + $27 billion activity and adventure.
Competition?
It’s a crowded space and frankly hard to keep up with all the new entrants, but my shortlist is the following: MyGola, Trover, and to some extent Pinterest Place Pins.
Revenue model and strategy for profitability?
HipTraveler has multiple revenue streams:
- Hotel Booking – API integration with Expedia
- Flight Booking – API integration with ClickTripz
- Activity & excursion booking – API integration with Xola
- Full service travel planning and booking – Via a partnership with TravelStore
- Advertising – Based on preference search, we position targeted Travel Supplier ads alongside travel results.
- (Forthcoming) – Our HipTraveler mobile app is in development and will be released this summer. The app will feature offline itineraries, hotel booking, and location based search functionality for points of interest, restaurants, etc. The mobile app will also have premium features only available to paying subscribers.
Our strategy for profitability has been to stay lean while we prove the model with a small market and to focus on conversion to sales metrics.
What problem does the business solve?
Consumers have en masse voiced their frustrations with the current travel options and their challenges have been well documented.
Today consumers visit 38 websites before booking (according to Expedia research) and they spend 3 times as long travel planning as they actually do traveling.
DIY consumers are forced to repurpose apps like Evernote or Pinterest to discover, collect, and assemble their discoveries.
HipTraveler makes travel planning an inspirational experience by eliminating the need for consumers to crawl the web for days or weeks searching for the best travel content.
Also, by making it easy to create itineraries, we’ve built a sizable database of pre-planned trips that consumers can simply search through to find the right trip, quickly.
How did the initial idea evolve and were there changes/any pivots along the way in the early stages?
The initial idea has not really evolved much, but the presentation of the site as well as the underlying technology has improved significantly with the helpful advice of our users and advisors.
Why should people or companies use the business?
HipTraveler truly it easier to research trips. We all know how challenging it can be to research, plan, collaborate, and find pricing for trips.
As travellers ourselves, we built the features that we always wanted to see on other sites. Then we tested with about 200 users and they agreed that we were on to something.
Now, we’re excited to release our Beta product, so that we can continue collecting user feedback to further refine the product.
What is the strategy for raising awareness and the customer/user acquisition?
It’s really a four-pronged approach:
- Local market awareness at the three Universities that we recruited from; USC, UCSD, and SDSU. Our initial goal was to make sure every student knew about HipTraveler. We’ve come very close to achieving that goal as adoption of the product at those Universities is off the charts.
- Social Media - We started our Social Media efforts about 2 years before building the product and have achieved quite a following. Through our social feeds, we offer travel advice, tips, and of course, beautiful destination imagery. Our social feeds reach about 1.5m consumers every day, so this is a great platform to announce our Beta release and to collect user feedback.
- SEO – We started getting serious about SEO development a couple months ago and the results have been outstanding. Site traffic has grown by about 100% per week since implementing the code changes. There’s a lot to learn with SEO, so this will be continual process, but we get better and better as we continue our education.
- Advertising / Marketing / PR – Being a self-funded, bootstrapped start-up certainly limits our ability allocate significant capital to ad buys, but we’ve found that highly targeted spending on a limited scale buys us enough penetration in key verticals to develop our metrics around customer acquisition costs and ARPU.
As mentioned earlier in this interview, our main focus is on increasing the conversion rate on our site to something north of the industry average. If we can do this, then it’s a formula for success that can be scaled with additional investment capital.
Where do you see the company in three years time and what specific challenges do you anticipate having to overcome?
I see a beautiful product that has been refined by all of the amazing feedback that we will have collected over that time period.
I see a vibrant community of travellers interacting with each other and staff of HipTravelers committed (and loving the process) of releasing updates to the software that enhances our users experience.
As far as challenges go, finding and retaining technologists who are not only technical, but also passionate about travel will always be a challenge, as well as finding and retaining key operations and marketing personnel.
Preserving the company culture as we grow will also be a challenge.
What is wrong with the travel, tourism and hospitality industry that requires another startup to help it out?
It’s not so much what’s wrong with the industry – it’s just that consumer behaviours have changed so much in recent years. Much of this change has been lead by technology enhancements to sites outside of the travel vertical.
Case in point: Pinterest and Instagram; both of these companies recognized that imagery is the most efficient communication medium and their well known successes have validated this visual approach.
Can you think of a better industry than travel to approach in this visual manner? The timing is right for a start-up like HipTraveler, one that speaks the “new” visual language of the consumer.
What other technology company would you consider yourselves most closely aligned to in terms of culture and style... and why?
Pinterest and Etsy. Both built an aesthetically pleasing tool that allows for people to express themselves. In essence, that is what we are trying to accomplish.
HipTraveler is a tool that enables our users to collect travel inspirations and to turn them into dream trips.
Tnooz view:

The dream is marvelously intoxicating: build a virtual travel agent who does all the trip-planning work for you.
We’re not talking about what Expedia and its peers have done, namely, tackle the part that was the easiest to shift online: bookings.
No, no: the goal is to go beyond the lowest hanging fruit of facilitating transactions.
The true Holy Grail is to simulate what offline agents continue to do: inspire, suggest, and make sure that the itinerary fits together properly. ("Have you allowed for a long enough of a layover at Charles de Gaulle to catch your second flight?" "Have you considered booking tickets to a Thai boxing match on Tuesday?")
And, really, why shouldn't a Web app do all of the researching on your behalf? Who’s to say that trip-planning sites can’t work?
Turn these questions around, though, and try to see it through a user’s eyes. Trip-planning sites may be a solution in search of a problem.
After all, not every person who travels is interested in actually planning their trip in any detail. Most guidebooks go unopened. Planners are a minority.
Put this another way: How many people consider trip-planning to be enough of a pain point that they're willing to master yet another website?
Perhaps HipTraveler can target diehard travel hobbyists. Go niche, instead of mass.
Yet psychology might work against it.
Among the subset of tourists who are true travelers -- the ones who love to plan for months -- doing the research is a hallmark of their identities, something they derive nearly as much satisfaction from as the actual journey.
These diehard hobbyists have created their own systems for trip-planning. Like any "to do" or "filing system", these trip-planning systems are makeshift, yet they're personal and effective.
These ardent travel hobbyists may not really have a pain point when it comes to research. They may not need another Web app to collect their magazine articles, filter their options, or share itineraries.
If few people find trip-planning sites to be a large pain point, then sites like HipTraveler face a hurdle. Can they build a user base that's large enough to build a business on?
These are all unsettled questions.
On the one hand, HipTraveler may be the noblest, most elegant attempt yet at tackling the trip-planning challenge. Especially of note is its tool that lets a user build an itinerary and then be rewarded every time someone else books it.
Its social and visual elements may be of the moment and give the site an edge once the mobile app debuts.
The crowd-sourced itineraries are fully bookable in flexible ways, so the monetization is "baked in" to the product.
On the other hand, the odds are against sites like HipTraveler.
Yet the odds were stacked against TripAdvisor, too.
Maybe the Chinese proverb applies here: "The person who says it cannot be done shouldn't interrupt the person who is doing it." Good luck to HipTraveler.