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Travel planning software: The most common bad startup idea (2012) (garrytan.com)
299 points by netvarun on Oct 7, 2014 | hide | past | favorite | 180 comments

I was the founder of TouristEye, a travel guide app that makes trip planning really easy. We got into 500Startups, we reached 500k registered travelers and then we sold the company to Lonely Planet, the leader of the sector.

I see myself on this post. Several years ago we decided to build an amazing trip planning, that allowed you to plan your trip day-by-day. You can see some screenshots on the Chrome extension (https://chrome.google.com/webstore/detail/touristeye-planner...) (not working now). We got over 100k users using it on their trips (not daily users obviously). It was gorgeous, people really loved it, Google really loved it, but the usage was pretty low. Just 5% of our users used it.

So because we were a startup we decided to kill it and we focused on capturing user wishes, and recommending those things for their trips (kind of Google Now for trips and offline). That's what gave us more usage, more income and finally it was one of the reasons of our exit.

So, yes. Trip planning sucks as a business. But all our team remembers it proudly. It was just fucking amazing :)

Ah man, I've been working on http://sploria.com/ for a while, leading up to launching an MVP soon and hadn't heard of TourstEye. Had a look at the app and the 'experiences' part is almost exactly what we've been building, damn :(

Congrats on your success with the product though, it's really beautiful!

The problem with travel planning isn't frequency of use: as other people have pointed out, Zillow and Cars.com are used infrequently but make money.

The problem is generating a consumer willingness to pay. Kayak has a commission on every sale, so their business model is baked in. But a travel planning site will need to get customers to pay extra, in some way, and they're reluctant to do so.

Travel planning is something that people have never paid for directly -- travel agents used to extract their fees invisibly -- so a travel planning company will either need to sell the travel themselves and collect commission like existing travel sites, or create a new market.

Zillow being used infrequently is an assumption. Real estate investors (and those that would like to be) use Zillow almost constantly because it offers some seriously helpful data that is vital to helping with good investment decisions -- and with real estate, you can never have enough data. I'm on Zillow multiple times per day. I also travel enough that I am Platinum in United, yet I have never used a travel planning site, nor do I actively look for one when getting ready for another trip. I use Trip Advisor for my preliminary hotel hunt, for restaurants. For attracticions, Trip Advisor works but so does a normal Google search. Travel Planning isn't 'painful' to me; at least not enough to use travel planning software. I just don't get the value or the problem it purports to solve. I do however, generally love TripIt Pro because there's nothing worse than looking for a confirmation number among multiple days worth of emails while standing at some counter or another. TripIt solves the very real problem of disorganized travel information. Before I used TripIt, I would have to hand-enter the ibro into my phone's Calender. But a travel-planning site? It would have to be really compelling to get me to invest the time to join yet another service. For 'challenging' destinations like India, it could be very valuable, but only if the quality of the information was better than I can find on my own through Google. There'd need to be more than just a bunch of third party APIs, there's need to be some original content. Trip Planning software is a hard sell because I don't find a week long trip to St Tropez or Austin that hard to plan.

Concur on that assumption. Real estate sites in general have a huge amount of passive traffic that can generate advertising revenue. Women in particular have a huge affinity to just browsing listings for fun and aspirational purposes. Whilst Zillow isn't ad driven, know a fair number of sites that rely on that. Source. Work in the space.

Zillow makes most of its money from ads for real estate agents.

Any good real estate investor is accessing MLS listings directly, not browsing Zillow. I don't know anyone who takes Zillow's rent estimation or neighborhood trends numbers seriously, nor who scouts deals on their site.

It's a combination of frequency-of-use and pain-of-problem. You use Zillow infrequently, but when you do use Zillow, you're like, "Holy shit guys, this is my house! It costs hundreds of thousands of dollars and I have to live in it for years!" You're more incented to seek out really good tools.

The problem with infrequently used sites comes when the pain point is fairly small. Even if that pain is reduced a LOT by the site, down to almost nothing, if the absolute magnitude of the pain of the problem is low enough, it's just not worth it for people to hunt down their vague memories of a site and try it out and see if it's any good and learn its process. They'd rather accept the pain.

Zillow is an awful tool (data quality is infamously bad), but it is fun infotainment that gets eyeballs to hand over to agents, and those agents get a huge commission due to the oligopoly of real estate agent industry, so they can pay large referral/ad fees to zillow.

Sounds absolutely perfect for affiliate-sales and ad-supported to me.

There are tons of travel affiliate programs, but none of them pay squat because the root problem is that "leads" are common, but paying customers are rare. It's a bit of an overgeneralization, but it isn't totally absurd to view the entire travel industry as a massive lead-gen operation for hotels and (to a lesser extent) airlines.

About the only thing you can do in travel is find some way to make something essential (housing, transportation) cheaper than it already is. If you can't do that, you're a middleman, and the game of the middleman is competitive and well-defined.

I'm in the market for a house now, and I use Zillow/Redfin every single day at the moment. I'm right there in the "I love this thing" state. I haven't purchased a home before, so it wasn't until now that I got to this point.

You're totally right that monetization is the next concern though.

In UK they even refer to this as "Property Porn" - people actually spend surprising amount of time looking at homes, since it's their biggest purchase, and largest asset. This is one of the reasons Zillow's USP was "estimates" - yet another reason to come back weekly and check how your home changed in value.

I guess the same could be true of travel planning, as well? Even though frequency of purchase is low (although not as low as a house), I can imagine the right kind of escapist travel planning site bringing back people every week to plan dream trips or vacations, however expensive or impractical.

How often do people really plan trips? For the typical working adult, probably once or twice a year if you're lucky.

This is exactly why this doesn't work. There are tons of things that people do that need fixing, but they do them so rarely that the costs of adopting the new way of doing it are significant when compared to the cost of just doing it the old way.

Said another way, very few people are going to take an hour to learn a new process which would otherwise only take two hours a year to do.

edit: This also is a way that a start-up could go super wrong and not know it until they try to scale. Identified pain point, good solution, engaged users with a real problem use it once and then it drops off completely. Talk about frustrating!

About 1.5 years ago, we were going through possible itches we could scratch with a bunch of friends and how to turn them into a fun startup. The very first thing that came to mind was a travel planning app.

After going through different rounds of evaluating the idea, we came up with the same conclusion that a service/app with 2-3 uses in a year is not a viable app to make money off of.

We followed the first anti-pattern of startup ideas and immediately started thinking about making it a platform (when in doubt abstract away). When we realized that we were pushing too hard to make a fun project a financially viable startup idea, we gave up and eventually moved onto different ideas.

It's a pity that such a commonplace problem is such an unattractive business model at least with the current approaches that come to mind..

Business travel might be an exception. Especially for companies who have to manage travel for their employees, and business travelers who want utility features that increase their productivity. Some ideas:

- Incentivize employees who share rides from/to hotel/airport traveling on same dates/destinations

- Show dates for destination that maximizes networking opportunities (in between conferences)

- Show locations with wifi in-between meetings

- Locations with ambiance ideal for business discussions

- Expense capture to identify opportunities for deals (employees love Starbucks during business trips, sign up for corporate deals)

For those solving these sorts of problems, you might wanna to check this out - https://developer.concur.com/devcon/PerfectTripFundAwards

This was my first thought, every big corporate I have worked for had at least one person or sometimes a whole department managing employee travel.

Please can someone answer the following question, in all seriousness:

What problem is the travel planning software startup solving?

Never have I planned a holiday and thought "I need an app for this." Maybe a better flight booking system, or a better guidebook, but never a website or app. In fact, I find planning holidays enjoyable and fairly straightforward.

I know of no-one who has difficulty planning their holiday, beyond the flight problem. And to make this work, you're going to need a lot of people with the same problem, whatever that problem is.


I have this problem every year. Last year I went on a 6 week vacation. I wanted to go to an African safari, but where? What should I see? What route is best? Turns out safaris are super-expensive and I can only afford 2 weeks. What should I do for the rest of the time? My flight had a stop-over in Turkey, so I might as well spend a few weeks there. Should I also go to Greece, Croatia, or southern Italy? It was October so I only want to go where the weather is still warm. I wanted to stay in interesting B&Bs, go hiking in Crete, see gorillas in Uganda, etc.

I ended up going through a human travel agent who planned a wonderful trip at a steep discount to the luxury safari pre-planned trips because she understood what we wanted to pay for (experiences) and what we didn't care about (fancy hotels).

Thanks for the interesting example.

Couple of questions:

Not many people go on six week vacations, right? If you were planning a two week holiday, would you still be faced with so many decisions and complexity? If not, the market you represent would be limited to longer holidays, which may be a very small market.

Second, could an app provide you with a better service than your travel agent? i.e. is this a "problem", or is a "solved problem" because a satisfactory solution exists already?

I usually take 2 to 3 week vacations, but I try to do interesting things. Ride horses around mongolia. Hike volcanos in Indonesia. Bike and eat across France. Planning is a huge pain because we have to learn everything before we can make the right choices. A travel agent already knows the domain. I do think there could be tools to help agents arrange trips more quickly given our unique constraints. Sadly, there is no app for that. Regardless, the market is likely a small niche.

I always have this problem. I typically book flights, hostels and travel in between seperately. I typically only stay in a place for 2 days so I need a new hostel and mode of transport for each place + a list of places to visit when I get there (with opening times/prices etc.). I usually put all of this into google doc, though simple things like pushing everything back a day are hard.

To me, the most in need of this are gap year travellers i.e. people travelling for a month or more around the world.


Are you satisfied with your current solution, or is there an outstanding problem to be solved?

I agree about gap year travellers. How big is that market? Also, is the problem not already solved by STA Travel and similar companies?

2.5m from the UK alone according to this: http://www.lattitude.org.uk/2012/04/the-number-of-gap-year-s... (sounds too high), this says 200k from UK http://www.gapadvice.org/index.php/considering-a-gap-year/fa... My guess is the worldwide figure is in the millions.

I want a rough plan with bus/train times, hostels shortlisted and other notes about how to make it all work together, then I'll probably change the plan if I stay in a place longer or shorter than expected. I'd like to have record of how much I've spend and will spend too. A lot of people in Europe are interailing, which mean they mostly just book trains and hostels - which seems like a simple use case compared to elsewhere.

Existing solutions in general are basically:

  - plan everything before hand e.g. get a bunch of receipts from STA travel before you go.
  - book a tour (e.g. g adventures), then everything is organised for you

I generally like to plan based on input from a variety of sources (guide books, magazine articles, travel sites, friends who recently took the same trip, etc.) Gathering all that information is great but I've sometimes wished for an efficient way to access and sort those recommendations when I need them most - while I'm out walking around - rather then in my hotel room.

Yeah, I don't get it either. I'm reading the comments here trying to even understand what a "travel planning site" would look like. I SORT of get it, but everyone seems to have totally different ideas of what this product would be.

I don't care, really. I just got back from 5 countries in Europe in 4 weeks. I just... went. I mean, we booked a couple places to stay ahead of time, and I planned my car rentals and bought tickets, but none of that was remotely difficult.

I never once thought "gee, I wish I could... uh.. go to a site.. and ..click things".

I have to agree. Just spent 6 weeks in China. Just booked the flight there and back in advance. No hotels, not much research, not flights or trains within the country. Very liberating. The only difficult part was deciding on a general route, which took some research.

If only we had some combination of software and people with expertise in destinations. Maybe we'd call it a travel agent or something like that.

That was snarky. But it points to the historical problem here. Most travel agents didn't/don't have a lot of expertise outside of fairly narrow domains. And they mostly depended on commissions from pretty routine stuff to subsidize labor-intensive planning for oddball itineraries--which I'm guessing can't be easily codified in software.

In fact, I'm sure there are plenty of competent travel planners but they cost money--i.e. are luxury goods--and most people don't want to pay the money.

Do people still use travel agents? The only time I used one (trip was a gift) we had a bad experience. I think pretty much all the younger generation/tech savy people plan their own trips online manually.

A good travel agent makes things so much smoother. Large chains get economies of scale so you don't pay much more than online/manually, but having all the bits and bobs sorted (courtesy calls if anything changes, transfers, etc.)

Some do. (My dad does for one.) For certain types of trips a lot of things aren't online and, even if you do a lot of your own research, it can be easier to have someone else do all the email and even faxing associated with making the actual reservations.

I also sometimes use one myself in specialized circumstances such as when I'm doing a pre-arranged adventure trip of some sort and the company is familiar with logistics and other activities to add-on.

The opportunity in travel these days is targeting people new to travel. Forget North America. Target young Chinese travellers who are just now beginning to learn there's a way to travel without staying in hotels and doing bus tours from highlight to highlight. Or wealthy Russians. You have to go really niche if you want to make money.

25 years ago when companies like G Adventures, Intrepid etc. started, nobody knew about small group travel, mingling with locals etc. Now that's all the rage for westerners. Bring that idea to markets that are new travel and you've got some opportunity.

My thoughts exactly. As other economies rise so will their thirst for travel.

We started http://www.voyando.com in March this year. It's basically a crowd sourced travel advice platform (a travel planning site in a sense). You're paying others to hash out your plans with your specifics (hours of travel, accommodation, proximity of restaurants, etc etc).

We are guaranteeing 3 good proposals for your trip and the best will receive the specified reward (anything from 5-100 dollars).

The struggle we are facing is that we are unable to get a decent amount of traffic because of the really big competitors with deep pockets to acquire this traffic. We're not in the same 'idea space' but we are still in the travel segment. This makes it incredibly hard to compete.

Despite good press, really good customer satisfaction and a business model, the site is struggling. We are now looking to partner up with one of the big brands to 'catch' drop offs from their main site with a service that can retain the customer. Maybe I'm being to optimistic that any big brand will take this chance, but I'm confident that our platform does it job and that it can be a tool to get your drop off rate down ("Didn't find what you were looking for? Let our experts help!)

If anyone can hook me up with the right people to pursue this, I would be very grateful :-).

This is a great observation! I'm two months into this "digital nomad" experiment, and the biggest pain has been lack of central organization for my schedule, todos, costs, sights-to-see, etc.

My interpretation is that the domain is simply too big, and the field of "personas" so varied that finding a critical mass of core users around common use cases is nigh impossible. Even within those identifying as "digital nomads", you have adventure tourists, travel-blog content marketers, $100/hr front-end consultants, cultural commentators, resilience quacks, and so on.

Look at a site like TripAdvisor, which does a great job of aggregating the most basic reviews of restaurants, hotels, etc., and even it contends with enormous problems like data rot, internalization, etc.

I suspect that, if the "long-term travel" community continues to grow, there will emerge specific niches that could reach that critical mass needed for an MVP of a serious travel planning app. For now, trying to parse through google results for "apps for digital nomads" is something like a nightmarish goose chase through an illegible jungle of travel blog shills.

What's a "resilience quack"?

Seriously. Inquiring minds want to know.

Sounds clever, but it really doesn't stand up to scrutiny. There are countless profitable businesses that aren't things you use daily (Amazon, E-Bay, AirBnB, etc etc.) Conversely, how many sites do you really visit daily? I visit, like, four. (Gmail, reddit, facebook, hacker news)

Travel planning software is difficult because there's so much competition and a lot of political forces trying to keep the newcomers out.

Eh, Amazon gets used a few times a month by a whole lot of people. Ebay definitely has addicts. AirBnB fits your theory better, but I think they managed to get noticed by being truly disruptive.

When you first hear about a travel planning site, it probably doesn't just happen to coincide with a time you're planning to travel, so best-case scenario is you bookmark it, which just goes into a giant list of bookmarks that you'll never look at again.

And when you need to plan a trip, you'll just go to expedia or hotwire or some other site that's gotten burned in your brain through advertising. Or you'll just google flights. Because that's the simplest thing to do and it comes up with pretty decent prices.

Airbnb from the beginning was an experience set apart. We stayed in Venice on my honeymoon and we had perfect local recommendations by a schoolteacher who lives there. We stayed at her house, and had breakfast with her every morning. It wasn't merely disruptive in the abstract sense. It is a better experience than being in cold tourist hotels.

>I think they managed to get noticed by being truly disruptive.

A company is not "truly disruptive" before it's disrupting something. I'll bet there are thousands of apps and services out there that have ideas that could potentially become disruptive if they gained traction. Many, maybe most of these will never go anywhere.

I bet you're right. Luck plays a huge, huge factor. And knowing the right people.

Everyone seems to have a different understanding of what a "travel planner" is / should do. I was thinking of rome2rio when I read this headline (which is very nice and doing great apparently), but from the comments here I gather many people want to solve the "social" (i.e. what to see etc.) aspect rather than the pure technical one (how to get there, how to save money) of it.

Considering how much money goes into travel (and related mergers/acquisitions - these are real acquisitions and not inflated valuations from 7-8 figure investments), it's definitely not a bad idea though.

I discovered http://www.rome2rio.com a few months back and it's a fantastic site. This is what I was expecting too, it will give me all travel options from point A to B, Google Maps but international/cross border. Maybe something changed on that Yahoo Travel planner, the original article was posted over 2 years ago.

Kind of surprised that the OP hadn't mentioned Hopper, the travel startup that was founded in 2007, promised to bring "big data" to travel discovery, and still hasn't much to show for $22M in venture funding: http://techcrunch.com/2014/01/20/why-travel-startup-hopper-f...

But I agree with the OP. Travel planning is a rare luxury, even for the rich. And I don't know what it's like to be rich, but when I find time to travel, I put a loose itinerary together and then improvise most of the way, with occasional lookups on TripAdvisor. There's not really a travel service that can meet the needs of wanderlust.

AirBnB is a solid exception to the "must be daily users - 20% retention" statistic. No way is their average user base a daily user.

Plenty of other exceptions: a large % of eBay users probably don't use the site every other day.

Selling on eBay or renting a property are highly intentional decisions: trip planning is something that will happen. The trip itself is intentional, but the exact itinerary will vary, and the lack thereof won't prevent the trip from occurring.

I don't agree that 20% retention statistic is a good way to view it at all. There are tons of exceptions to that rule - Amazon, Kayak, Turbotax, or even TripAdvisor. I often view that as entering one's normal "workflow" through whatever it is they are trying to do - it's a rarity, and there is a good chance that a fringe app wouldn't make it.

There are two unique userbases for AirBnB - renters and renters. Renters may not have a 20% daily retention but I would bet that rentees are much closer to 20%.

On top of that, AirBnB is a marketplace. I would imagine that marketplaces are affected more by supply and demand ownership than daily retention.

I was going to propose the exact opposite: renters who want to keep their ratings high go back frequently to answer inquiries while each individual rentee only goes on the site occasionally when traveling.

I chose not to use "owner" because not all people listing on AirBnB own their property, but I think we were thinking the same thing. People listing properties almost definitely have higher retention than travelers.

Don't forget that there's a distribution around the mean. You'll probably find plenty of outliers. It'd be interesting to see the graph MixPanel's guy is basing his estimate off of.

Let's call it a rule of thumb. There are always exceptions in startups.

It's a bit different when it comes to business travel. I'd use and pay for travel planning for business where my schedule can take me to out of the way places and the schedule can change frequently. There is a tier of business traveler in small businesses or who are self employed and need an economical itinerary with specific attributes for flights and hotels, but who don't want to stay in crappy places. I've spent far more time on HipMunk and on the phone with hotels.com and re-booking flights than I should have to. Maybe start a manual service, learn how this stuff works and then automate it.

Or you could start using a good travel agent, as they would do these things for you.

Is this a good time investment for you? You have a choice on what you spend your time on. You could install your own plumbing, write your own t's and c's etc. or you could pay someone to do it.

Having thought about this idea in the past, I can say that one of the difficulty lies in the fact that the market "seems" really large, when in fact, you can only address a limited portion of it. People have different tastes and goals in what they want to accomplish in a "trip", and because the market seems so vast and large, the idea tends to gravitate towards the middle ground. You might satisfy a wide array of people, but none of them will really "love" your product. So rather than daily usage, I think the problem is of segmentation first (and competition, etc following...).

I think the issue is revenue and not user forgetting about the website. People remember sites years later. The problem is the business model. People are not willing to pay for the services of a travel planner which is expensive to build, which means your revenues are affiliate or ad based. This is not enough to support the dev costs.

I've just read many comments that show getting traffic is not an issue. Yes it might be more competitive but lots have gotten traffic. The common issue I see is that none of them have been able to generate enough revenues to support themselves, even with good traffic.

Bingo. A travel planner is pretty much a solved problem. It's called a savvy, experienced travel agent who gives personalized service. The problem, as you say, is that most people aren't willing to pay for that type of service. And it's unclear to what degree software can solve the time-consuming stuff--such as places that aren't online or at least require emailing back and forth or phone calls (as is still the case even in the US with a lot of B&Bs for example). Which is the problem people are looking to solve, given that air reservations and the like are easily handled by existing sites (except when they aren't:-)).

No daily usage, not enough trips and also it is impossible to build a multi-billion corporation out of an SEO play. Too bad TripAdvisor won't work. /S

I think a lot of travel sites focus on saving money for travellers. What if money is not that important.

My friend came up with this idea. I think it will help many people. The idea is that one put in how much they want to spend and how much time they have. The site will show various travel or activity options that are possible. One can further limit by parameters such as road trip only, out of state destinations, in town activities, etc. Almost like travel agents.

I have been looking for something similar but haven't found it. My friend is a great traveller and he and his wife have run out of places to visit. They just want to explore new places.

On other hand, my wife & I are not so great travellers, we never know where to go. We end up picking top destinations from TripAdvisor, then we find those a bit too expensive or require too much travel time, etc. Sometimes we just want to get out of town and not worry about where we are going.

For now, I have solved this problem for us by creating a spreadsheet, with a list of places we had picked and estimate cost, best travel time, and ideal # of days to spend there. But of course, this is for places we researched and could not afford at the time.

This article rings very true, but on the other hand I've thoguht the same thing about a dozen other things that seemed dead until someone came along and did what seemed impossible.

When Myspace was neglected and Livejournal stagnant, a lot of small actors tried to fill the void but there was absolutely no money to be made and I predited them all dead within two years. I was almost completely right.

Figure I'd add my own two cents to building software for this: School project with a few buddies, decided to make an itinerary planner. Problem was that it was messy and difficult to plan a trip with 3+ people. Emailing back and forth gave you long chains, calls and group chats were difficult to schedule together and settle on something. Ultimately a Google spreadsheet or shared doc was the best option despite limitations. Enter the itinerary planner: Post possible destinations, majority vote by a certain time to include or exclude in plan. It was to act as a central place to plan pre-trip, view during trip, and post after trip(web app or native app).

Eventually, the realization was the same problem as most people have mentioned, retention. So then comes the weekend planner. Miniature trips or adventures for weekends or long weekends are much more common, spontaneous and way easier to make decisions. Google Now already offers suggestions of events and places to be during the weekend based off Geo and whatnot, just have to take it a step further.

I had a travel planning startup for 5 years and I agree 100% with Tan's about that you have to re-acquire the user every 9 months and the main reason is that the user is unable to remember your "name". But imho the main problem on travel industry if you are doing a travel planner is not exactly that the user doesn't remember you... this happens at other industries: job finders, real state, consumer electronics...

The big problem in travel is competence. It makes user (re) acquisition REALLY expensive and probably, as a startup, you can't afford it (an this mixed with no actual retention is painful). And why is it so expensive: because you cant compete with advertising, SEM or even SEO with big players out there with a LTV that multiplies yours by 10x. And actually, do a better job than you when we are talking about user satisfaction.

Airlines, big online travel agencies are really good at this and pay for a) Long tail SEM, b) content for being top SEO. Remember, Online Travel Agencies are technology companies with big resources. They are extremely good at SEO, at loyalty, at landing page optimization, at design, at customer service... their life is on it.

Think about this scenario:

User searches at google for "traveling to Vienna" (or even "travel planning vienna"). You know two things about that user: 1) He wants to plan his trip to Vienna (75% true) 2) He is going to buy cheap tickets to Vienna (95% true).

Big OTAs or Airlines know this, and what they do? They fake they are travel planners doing better (expensive) SEO than you as they know that user is going to buy the ticket at their site (that's 2$ per visit revenue)... because they do that extremely good. If they fail noone cares: User wont remember and at least they had brand awareness for their plane tickets.

Anyway, i think the problem is much simpler and applies at every industry: if you don't have a great retention (and this can be something not under your control, e.g. because what you are selling is needed twice a year) you have to be really good at user acquisition. And being good at user acquisition at a not-niche sector is extremely hard, no matter how good your product is. Probably you will have to focus first on what's your hack on getting users instead of at having a good product. Sad but true.

I've been reviewing Alexa's top travel sites for years hoping something changes... and its pretty discouraging: only 1 of top 25 sites not a ticket-seller: Tripadvisor (2nd). 4 in top 50, and all of them are super seo sites.

Google has been punishing not content sites for years, even being the best solutions. We've seen a lot of amazing ajax tools for almost every problem we could figure out... but if they were not seo compatible, everyone forgets them. I hope this changes in the future, e.g. mobile apps have another search scenario.

I think if you could own the pre-trip organisation, and the post-trip sharing that would help cement it in the users mind. Most people dump the photos onto Facebook, but I imagine if there was a way to organise the data nicely or build a basic travelog from the trip data some people would be interested.

Interesting about the only non-ticket seller being Tripadvisor, I didn't realise it was that skewed toward trips sales.

Some of the problems in the article are what my startup has been dealing with for a while. We are basically trying to deal with the competence issue by letting people create travel logs of their adventures (both during and post trip)and use that to make customized travel suggestions for the future. Users can basically share trips like the one below and we link up with most networks to import content from past trips. https://esplor.io/trips/k8g96my2j4vnm.

My friends in Mumbai, India are beta testing a beautiful travel journal Web app at http://serai.me/ (after a year of hard work) to share those beautiful trip photos with friends and they can contribute/comment so each can share his/her photos of the trip to a unified journal !

The pre-trip organisation bit is something We are working on as part of a long term goal of our new startup, Planning To (www.planning.to)

Being able to use the context of peoples existing plans and calendar/schedules to provide automated concierge type suggestions of what would suit them best in terms of travel (e.g flights, hotels etc)

Focused on B2B travel rather than vacations though for reasons others have put very well in here :)

To begin with though, we want to solve the problems inherent in calendaring/scheduling in the first place, and then build a technology platform from there that people can use to add context and automation to all sorts of use cases, travel being one of them.

Anyone interested in what we are doing would really appreciate feedback, good or bad :)

I know of one startup, Compathy(in Japan) that are working the other way around -that is, they're building a product that's first for post-trip sharing and then adding pre-trip planning elements/partnerships to it:


I think this is a good strategy since even a small population of traveling power-users who are keen on sharing their experiences can generate a lot of content and value for your site.

> pre-trip organisation

Here, that's a reason for having very low trust for travel planers. They want to bring you sideways. You're the product.

I've arrived at this conclusion in my mind regarding trip sharing or trip rating services - though for slightly different reasons.

Once someone creates a self-hosted, WordPress-like, trip sharing software, I'd be all over it. Like my blog, I'd like to know that my time spent writing and uploading photos is going to last longer than the typical lifespan of a startup.

Not wordpress, but currently building a digital travel journal in which you can share trips like this https://esplor.io/trips/k8g96my2j4vnm (press see timeline for the diary view)

Based on what you said, you seem like the user we would target. Any feedback would be brilliant!

I wonder if a travel-planning-app-as-a-service would work? Or maybe more as an affiliate system. I.e., you build a travel planning app and try to convince the OTAs (and the airlines, but I don't see how) to sign on as affiliates. Your travel planning software might have to be embedded in their site, I don't know. It might not be workable but it does dodge the user acquisition/retention problem.

I've used a service which is a bit like TaskRabbit for Travel to plan a trip to Hawaii - you can see it here https://www.triptips.com/#!/place/maui-hawaii

It's more about the "how" than the "what". If you have a general idea about what you want to do the trip planners give you unbiased advice on how to do it and save you maybe 3 or 4 weekends of trip planning

That's interesting, but it's not what I was talking about and doesn't solve the OP's problem of having to reacquire users every nine months.

Frequency of need is a non-issue in the travel space or any other. As has been pointed out, there are many other spaces where lack of frequent visits has not been a barrier to success. Nor is name recall/retention an issue - if you create a great first impression i.e. delight your customer the first time and give them something they really like, they are unlikely to ever forget you.

IMO, the key issues to cracking this space (and these are beyond building a great product that people will find useful which is crazy hard anyway!):

1. Getting new users from free channels/biz dev 2. Getting new users from free channels/biz dev 3. Getting new users from free channels/biz dev

Most startups look at user acquisition as a secondary consideration to the product. In the travel space, it has to be atleast an equal priority, if not an even higher one. You HAVE TO figure out how to hack user acquisition from free (or very cost effective) channels or you will fail. The sooner you start thinking about that the better.

4. Making money. If you can acquire millions of users, this becomes significantly easier.

5. Breadth/size of the space. This is a huge space with tons of variables and different personas. You have to figure out a way to make this work to your advantage. For example, most travel startups, being based in the US, seem to think that users only exist in the US. There are millions of users, especially in fast growing developing countries, who are pretty much being ignored. Another example - if you can figure out how to service the whole space well (and I know thats a BIG if), then at any given time you are going to be catering to some kind of user (increasing your likelihood of reaching millions) unlike a niche service that requires to scale based on a very specific user persona

If you can keep acquiring new users cost effectively and delighting them with your product, you will succeed in the travel space. Most startups cant do this and thats why they fail. they dont fail because of the frequency of need or name recall.

As someone who is working on this idea currently, this post has really got me down.

Atleast the fact that this was written and its currently at the top of Hacker news says that this pain exists. The author of the post is saying that no solution has been found yet. You should consider this a blessing in disguise and not get disheartened. There are perhaps atleast two things to take away from this.

1. The problem exists ( and is a genuine problem that quite a few people care about! ). 2. A good solution has not been found yet. ( also kind of good for you! ).

Apart from this, it also gives you a lot of information about the industry. Especially the discussions that are happening here. So, why dont you consider this a loooot of great feedback and go back to the drawing boards and go disrupt this industry ?

A couple of guys I know did a small travel planning website. It's plastered with ads. I think they have almost not touched the site after they launched it, and it's doing ~6-8K€ monthly with ads (traffic coming from SEO).

Don't get discouraged by a guy explaining why it can't work according to its theory.

This post is pretty light on justification.

20% retention is neither good nor bad. There are a lot of businesses that survive on one or two events a year. If you are in the business of selling metrics software (like his friend at MixPanel), you probably want people to come every day.

The "I don't have room in my brain" argument is just silly. I can open my refrigerator and see hundreds of different brands. There are millions of websites, of all kinds! Should we stop building websites because there are a lot of them and it's harder to differentiate?

It's pretty hard to swallow this kind of advice from a guy who founded a blogging platform in 2008, 5 years after blogger.

Anyway, as our man PG likes to say, just go make something useful. The rest will take care of itself.

Just make sure you're validating your idea as you go instead of just building it, and you'll find out for yourself if its worth continuing.

As depressing as it sounds, there's little point in continuing product development without solid validation. Its a problem I ran into at my previous startup - a good product, but just not needed by enough people.

Do you have a business model wherein people will pay you money? I can only see this working for B2B. If you can't answer why it will be different for you, rethink your business.

Are you working on the idea, or working on validating the idea?

Don't get dejected. A person can probably write a similar post about every great company that will get started in the next 10 years. Prove cynics like that wrong.

Same here. I've been doing user research on the subject, and while there are some clear problems to solve they might not just be worth solving.

I've got a fairly unique take on local trip planning @ 80%. If you want to chat, shoot me an email!

Time to prove him wrong! :)

I would very much like to be wrong on this one.

Why not target travel agencies instead? Agencies can create/manage itineraries, hotel reservation & bookings, destination maps, etc? This will get you paying customers and daily users.

I have two primary concerns when booking a travel, one that I don't end up at a boring place and two that I can manage it in the most economical way. Google search helps me figure that out pretty well. Google Maps are great when I'm actuall at that location. TripAdvisor has nice information. Airticket listing sites are a necessity. AirBnb works well for places to stay. Lot of hostel booking sites in Europe work well. But I haven't found one single tool that can handle all that exhaustively.

Way too many travel planning softwares try aggregating resources from across the internet, just posting it in varied forms. But they don't really give me the confidence that it's the cheapest and the best place I can be at. Moreover, when you look carefully at them, they skimp the details -- the prices and timings are usually way off. To top, if they try to put a fees on top of the original price, it adds to the cost without actually providing any ease. So I still have to resort to going to the original source of the content or just doing my own research. Also, many of the travel planning softwares overlook the fact that motivating people to go for a new trip is a huge challenge. It's also interesting to note that the blogpost was written over 2 years ago and is still true.

"cheapest and the best place I can be at" -- that phrase is entirely too subjective to be able to actually easily solve. I know for myself, say on the Big Island of Hawaii (a place I know pretty well), "best place" can incorporate temporal concerns, desire for beaches or mountains/hiking, maybe a place with a kitchen vs. sustaining one's self on market goods and restaurants. Those three variables could describe at least four different places on the island in my own mind. How does that get mapped to a general site?

Exactly! Every person has his own concerns about planning a trip and the problem is too subjective. That's why I said, I have to resort to my own research to figure out the place, instead of depending on a travel planning app. Travelogues and ratings posted on blogs and TripAdvisor give me a better idea of what to do, compared to a list of things generated by an App.

A question I'd love to have answered - I want a flight that is within min/max miles and costs less than a certain point intersected with a certain class of lodging within a certain price range. Available "amenities" of the location a gravy filter.

I wanted a site that gave me the confidence I was looking at all the places to stay in a destination, including the actual prices from every site. Nobody was combining airbnb with hotels and Hotwire and all the other sites I checked. I ended up building it myself: http://AllTheRooms.com.

Creating travel planning software may well be a bad idea, but I find the reason he gives is really weak. It boils down to:

People in America don't plan travel often enough.

If that was the reason, then almost any travel startup is non-worthy. This is definitely a problem, but it's more to do with the difficulty of ranking a travel planning site in Google which is where people who don't travel often usually begin their planning. This is why SEO is so critical to any travel website.

It also conveniently ignores the rest of the world as a market. People outside the US do in fact travel far more often and more elaborately and ignoring them in the equation just boggles my mind.

Disclosure: I'm also one of these people who acted on this bad idea of creating a travel planner: http://www.travellerspoint.com/planner/

My experience from this is that people do have very different expectations of how a travel planning tool should work. So the earlier comment that it faces the same challenges as to-do apps, etc.. rings very true to me.

The biggest problem I have had with travel planning startups is that many of them focus too much and too quickly on monetisation - often leading to a poor user experience.

When I'm travel planning, I like to somewhat explore the destination (like reading a guide book) and think about what to do, where to stay etc -- rather than being immediately shown a list of hotels & airfares.

Have a look at http://owegoo.com I talked to the founder yesterday. Basically they are a search engine for destinations. Good if you know what to do but not where to go.

Yeah, we launched http://owegoo.com just a few months ago, trying to solve a few of these problems. Please hit me with feedback - here or at sofia@owegoo.com!

I'm aware of one such startup (https://roadtrippers.com/) that has $4 mil in funding[0]. Ideas don't work until they do, I think this nut can be cracked.


The big problem I see is that planning does in a lot of ways remove the essence of travelling (see The Art Of Travel by Alain De Botton). The best trips I've been on have been largely unplanned and taken on a day to day basis which flies in the face of a single up front plan which is built once and referred to throughout the trip.

What I do see a market for are the tools which sit in the middle and enhance your ability to plan once your in a location. Tools like:

- flight management - hotel booking management - local knowledge resources - tools for connecting with locals - language tools

A lot of these are already available in various forms through dedicated applications. I use kayak, hostel bookers, app in the air, wiki travel plus local subway and language apps. Whether there could be an advantage to it all being in one place I'm not sure but the tools on their own seem to do pretty well once you've put together your toolset.

People don't buy cars or get married very often either, but there are plenty of tools to help with those processes.

I've been working on a travel activities startup in stealth mode, but had to put it on hold because of other work.

Reading this article made me think back to some of the challenges I had initially with customer development. People were always interested in the idea, but everyone seemed to want to use it differently. It was a real challenge to come up with something that would be useful and satisfying for most customers.

Along the way, some people tried to talk me out of it, saying that the app should be more like location exploration, because people don't travel alot. My response was that while everyone doesn't travel often, there is always someone who is planning a trip. I don't think the frequency of travel is the issue--it's the logistics of it.

Enough of waxing nostalgic, I think I'll get my packages and libraries up-to-date and get back moving on my idea.

I can see why travel planning startups fail but I don't think its for the reason implied that people don't want the service. I travel a lot and I always plan (to an extent) on line but I go to the best sites for the aspect required eg. for flights Skyscanner or Kayak, for accom booking.com or laterooms or hostelworld or airbnb. For what to see Tripadvisor. If I want combined hotel and flight, Expedia. For local bus times etc. Google Maps. They are mostly great services from billion dollar companies that have put in a lot of R&D. Why should I go to a new combined travel site trying to combine stuff in a half arsed way? To appeal to users it has to better than the existing solutions already available.

I have a travel startup that is meant to solve the planning problem in a different way, but I agree with Gary. We painfully learned that -

a) We created an elegant solution to free. That is always a bad idea

b) User acquisition is extremely hard without spending tons of money

c) Even though the users love the product, the fact that they would only use it couple of times a year means that you need to have lots of users, which circles back to the previous point

It sucks because the travel space really needs quality apps and I would like to believe that there is a way around all the issues for startups. But the fact remains that it is a bad idea for most people.

In the smartphone world you don't need to remember to use the service. Service can use well targeted contextual notifications to remind you when it is relevant. Obscurity is much less of an issue for intelligent services (even if they are rarely used).

I believe that there is probably an opportunity to build these services that have never worked in the desktop world but can work in the mobile world.

Travel planning has other problems (e.g. all the money is in bookings and not itinerary creation). Hotel bookings are super profitable - and hence expedia can spend > $1B per annum on adwords to re-acquire customers.

These are all real and serious challenges. LTV of an average user is a tricky one because it can involve 19 "users" worth $0 an 1 worth $500, but the price of an adwords click or whatnot will be set based on the $25 average value. But, you might have something for the other 19 "users" that doesn't bring the average value up to that scale. It's a legitimate difficulty.

The acquisition/reacquisition and learning to use some specific software paradigm is a legit difficulty. Something that works for a hotel concierge using it daily may not work for an occasional traveler.

Real problems.

OTOH, I think that ultimately "travel planning" or something to that effect is not impossible, just difficult. Review sites like Yelp are great for finding something that is popular but not terrible on average, but I have gotten far more mileage out of guide books where the author seemed to have tastes that I enjoyed. Usually I don't have one, but.. There is still a ways to go.

It would be facetious to seriously suggest some solution because obviously these things need to be banged out in the real world, but I can imagine all sorts of things that might work. How about you enter the location of your accommodation, tick a few boxes for your budget and travel modes (walking, taxis) and it spits out a decent guidebook chapter. Local walking maps, restaurants, bars, local gigs for this evening. Some explanations about local tipping norms, buying train tickets and maybe a one page phrasebook. Give me an app where I can push a button to do this from a Cafe's wifi and I'll at least give it a try. If I can print it out, I might.

Maybe a person could be in charge of a city or part of one. Maybe not. I dunno. The idea that good ideas and execution can't penetrate this industry doesn't sound convincing to me. I have no doubt that its hard but I also wouldn't be surprised to see startups take off that really nail informational based stuff for travelers.

One upside that the commercial realities of this industry can offers is a multitude of opportunities to make money from having a userbase . IE, if you have 1,000 active users in a city on any given day, that's enough to make something.

In fact, I think it's something that's accessible for people to have a go at. Even authoring a local guidebook for your city (provided it is not New York or somesuch, in this case, pick an area). Keep sections up to date with weekly info and release it as an evoke, app or whatever.

Information is still what the traveller needs, IMO.

I had to laugh when I saw this headline.

I'm planning a road trip. And I have been actively searching for a "road trip planner" site.

Whatever Yahoo had at the link he mentioned apparently is gone; it just goes to the Yahoo Travel page.

And everything else I found was complete garbage. "Wrap a Google Maps Directions page with something to put pins in the map near the route for certain categories of attractions" is as far as any of them went.

I don't know what Yahoo's "Trip Planner" was about, but given the overall lack of ANYTHING like a decent road trip planner available, I'd have to guess that it also sucked. Otherwise some of the competing sites would have stolen at least SOME of the obvious features.

What was missing, you ask?

1. Some way to tally up a list of interesting sites. Showing me sites along a route is only about 20% of the way to being interesting; before these sites I could Google cities on the way to find destinations to visit. Actually providing more value than Google already provides is critical.

2. A way to print out area maps and contact details for each of the interesting sites.

3. A way to sort the sites and travel details by day (I'm planning a multi-day road trip).

This is for the MVP, and shouldn't take a competent developer more than a week working with Google APIs or equivalent. A good developer should be able to crank this out in a day or two. I'm tempted just so I can use the functionality to plan my trip!

I have to assume that the dozen or more sites that I looked at were made by people thinking "I'll make a road trip planner!", but who had never taken a road trip. Or who were copy-and-paste developers who could figure out just enough of the APIs to get a basic Google Directions view going, but more complexity was beyond them.

Bonus features (post MVP):

* List the cities at both ends of the road trip and the KINDS of places you might like to visit, and suggest various route options along with the unique stops you could make on the way.

* After you list the places you want to go and how many hours you want to spend at each, plan the driving stops and an optimized order of visiting the destinations. "Day 3: Get up, go to X restaurant near your hotel, drive 2 hours to Y museum, lunch at Z restaurant, then spend 3 hours at the museum across the street..."

* Include AirBNB locations on the map in addition to hotels, but ONLY show both near the end of a day's drive (corollary: give it a range of how many hours you want to be driving per day).

* Let me put in preference categories of food, and after planning a route, look for restaurants near where we'll be at breakfast, lunch, and dinner. Double-plus bonus: Only recommend restaurants that are open at the time I'll be there. (Yes, Google does have a first approximation of this information, though it's often spotty.)

* Let me (easily!) blacklist specific businesses or chains. I hate calling up a map with that shows 15 restaurants in an area, and where I would only ever go to 2 of them, and having to click on all the dots until I find the right ones. Google Maps needs this feature!

* Let me filter attractions that get terrible reviews, so they don't clutter up my map -- and pull in reviews from Google AND TripAdvisor (assuming they let you?) and other sites. In some small towns, you might have one review on Google and one more on TripAdvisor -- if there are a ton on both it doesn't matter, but if there are only a few, even one more can be relevant.

Is this a good business plan? Heck if I know. I only know that I really want a site that does all of this right now (or at least points 1-3). And I sure-as-heck would remember a site like that and find it again when I took my next road trip. Bookmarks are magic ways to supplement your memory. No idea how many people still do road trips, though. Maybe more would if they had the right tools, and knew what awesome places can be found in the middle of nowhere, then it would be more popular?

> This is for the MVP, and shouldn't take a competent developer more than a week working with Google APIs or equivalent. A good developer should be able to crank this out in a day or two. I'm tempted just so I can use the functionality to plan my trip!

I assume you're not a developer?

Yeah he wants a geographical recommendation system with tons of data that likely don't even exist online like restaurant menus, and have that quickly hacked in a week.

I'm not looking for anything that isn't online already. I would be happy with JUST the results available in Google Maps, in fact.

I'm not asking for restaurant menus; the restaurants ARE categorized in Google Maps already.

I know exactly what data is available, and how I'd code it. I just don't have the time.

I'm surprised recognizing an animal in a photo is his example. Apparently computers are already almost as accurate as people. https://karpathy.github.io/2014/09/02/what-i-learned-from-co...

Yeah, and it only took like 50 years. Easy. Next problem?

And location data in the photo only required relativity and space travel.

Good point. I'd be curious about the person-hours worked on both the problems in the comic.

My first reaction was "you'd have to explain some things are easy cause there's libraries/tech that does that". I guess the real explanation is " countless hours and dollars spent by others who came before us make this easy...".

Hey, shorter than it took evolution.

No, I'm an awesome developer. But I mostly do games, video streaming, and app development, so I don't know the relevant Web APIs.

Would probably take me 3-4 solid days to get to MVP, maybe even the full first week, given that I'd be slowed down by the learning curve. But I'm also very busy (see: "I'm an awesome developer").

Action speaks louder than words

And your action is to downvote the truth because I haven't spent 40-60 hours proving that I am an awesome developer? Sorry, I don't feel the need to prove anything to you or anyone I'm not currently interviewing with. My resume speaks for itself.

It's also about five hours of work to just do it the boring way by hand. An 8-12 year amortization of a project that people have argued eloquently is a total waste of time as a start-up? Why wouldn't I work on something I cared more about, instead?

Hey Tim,

So what did you end up doing for your roadtrip? Did you find a tool or did you just do it on your own? I'd be curious to see what you ended up using.


I agree - everything in the travel space is crap. Whether it's because it's hard to monetize, or because there's no archetypal traveler making it hard to cater to any particular audience ... I don't know. It's a tough nut to crack.

It's not going to help you plan but if you'd like to blog about your road trip when you're on the road, take a look at my attempt to build a "micro blogging" website. Each day, you're only allowed to write 250 characters and attach a single photo:


It's free to use, feedback welcome. I wrote the site for my little road trip because I was so unhappy with everything else out there. The idea being that a character and photo limit forced you to be concise (much appreciated by friends and family), making it easier to maintain and look back on. Here's our trip (we were lucky enough to get some air time on the BBC world news):


Hey mate,

just signed up, i'll give it a shot for my upcoming trip, few points from the sign up process:

- Dates seem to be American Format (this is fine but at least indicate it in the placeholder text) - I have no idea what a marker is, perhaps explain it or even let people know it can be blank!

My first reaction was "that's not enough!", but on further consideration...

I'm going to sign up and give it a try. Thanks!

But is the problem that the world doesn't have a good road-trip-planning app, or that the world doesn't take enough road trips to warrant such an app? That's more of Garry's point, at least as I interpreted it. Lots of people have travel-planning needs at the moment they're planning travel. Unfortunately, most people don't travel all that often.

How often do you take road trips like this one? More than once a year? Monthly? Weekly? If you can convince me that there is a large addressable market full of people who take weekly or monthly road trips, I'll grant you that someone needs to spend some cycles making a better road trip app.

Now, this isn't to say that it's not a real problem. Clearly it is. Case in point: you're taking a road trip, and the apps you've looked through suck. You'd love something better. As would others. Fair. So perhaps the ideal solution here is for someone to make a better road trip planning app on the side, as a hobby. It's probably not a big enough market to warrant a startup. The use case is too specific and too infrequent to build a viable, fast-growing business model around.

No disagreement here. I ended with a question as to whether there's a market; I don't know that there is.

AAA apparently has a road trip planner that's only available to members. That's one business model. :)

TripAdvisor could offer something to help promote their site. As I said above, a strong developer could crank out something better than most existing alternatives with a small time commitment.

A hobby app might be the right speed. Some suggestions I got above might end up being "good enough", though.

You could just get a guidebook, lonely planet or whatever. They usually have maps, tips on places to visit, restaurants, ... and best of all work without internet connection.

I could, but considering the length of my road trip, I'd probably need nearly a dozen, if they're done by state (more if some cover only a portion of a state): My trip will cover: Colorado->Kansas->Missouri->Arkansas->Alabama->Georgia->Florida->Mississippi->Louisiana->Texas->New Mexico->Colorado

I don't want a library of guide books to be taking up space in the trunk.

Amazon.com has an electronic book reader that will knock your socks off.

Guidebooks remain surprisingly useful for a lot of circumstances. They're far from perfect and tend to be out of date for food/lodging but they're still a well-organized and inexpensive resource that at least provides a solid starting point.

I also wanted a map with both Airbnb and hotels, so I made one myself. It's now an aggregator that includes all the hotel sites and a bunch of airbnb's competitors too. The site is http://AllTheRooms.com.

I do like your site but for everyone designing these sites: Please add an option for children. I use services like this very often but I'll skip it immediatly if there is no selection for children (you can guess why).

edit: There is even a bigger problem with your site, the prices do not match even close, see "kotimaailma" - the actual price is not even close to the price you display.



edit2: Or is the price per night? Not the whole stay?

I'm not saying his site does this, but some of them misleadingly display prices pre-taxes, which for hotels in the US can be up to 20% less than you end up paying.

We try to show the same price as the site we're linking you off to. The common practice of 99% of the sites out there is to include the taxes in the price for non-USA destinations, but for USA destinations the taxes are added later. Of course it's ridiculous and doesn't make sense, but the logic is that since everyone else does it that way, you have to as well or it looks like your prices are worse than everyone else's.

There's also the question of fees, and we haven't handled that as well as we need to. For example, Airbnb adds fees on during checkout that aren't included in their landing pages. When we include those fees, which we do right now, it looks like our prices are too high. But we keep them there anyway so that there is a fair comparison with other accommodations options.

Price is per night. I guess we need to message that better!

Interesting! I'll give it a try.

After I wrote the above I also found https://www.myscenicdrives.com -- which makes it almost to the MVP level, though it's very clunky to use.

How did you like Roadtrippers?

I believe this is one of those things where everyone has their own idea of what 1 - 3 should be. I think it's ambiguous enough that people will see what they want to see and then realize that the vision doesn't match when actually implemented.

A trend that I've noticed is that many people don't put much effort in trip planning. Their workflow is basically read travel blogs, talk to friends, pick a couple of big points of interest, book a place that seems nearby to some things, and rely on mobile internet/concierge/locals for everything else. And maybe aside from finding the best place to stay, I haven't seen people consider the other steps to be pain points.

I don't think you can solve this with just APIs currently. There's a ton of information currently but extracting the useful bits and creating a complete trip plan just isn't possible today.

Heck I've done the equivalent of screen scraping by visiting tripadvisor and lonely planet thorntree forums and even that was not enough. I tried a new site called triptips.com and found they had good balance of human intervention from locals to simplify the hardest part of travel planning.

Its relatively easy to book a flight or hotel or air bnb. The hard part I've always found is determining which hotel makes sense given what i want to do at the destination. should i rent a car and so on..

Even the ones with a lot of effort put into them suck for the same reason project/task/todo management software sucks. Everyone plans things with a different thought process.

Agreed. I don't take vacations, so I wouldn't know about travel planning, but when I buy plane tickets (which isn't very often) I always use the same service. That used to be Kayak, but I changed it to Google Flights a year ago because their UI/X is way more simple and more intuitive than anything else out there (AFAIK).

So I too don't think the seasonal argument holds up, it's just about quality and marketing.

Check this out http://www.triphobo.com/

Just glanced at it briefly. Looks almost entirely unlike what I need. :(

"26 cities available for the United States" ? I'm not visiting some big famous city by air; I'm going on a road trip. Looking at the list, I'm going to be at two of them, but I'm also going to travel through New Orleans, Kansas City, Springfield, MO, Memphis, TN, and about 100 smaller towns on the way. The point isn't to get to (e.g.) Orlando ASAP, it's to have fun on the way.

Regardless, if I have to list each town individually, the site is almost worthless, because I can instead just Google the destinations myself. It looks like I can accumulate lists of destinations IN a town, but for anyone who's traveling by car, a travel site that only shows the most famous attractions in a small number of big cities is doing no one a favor.

Hi Folks..

Have been a dormant user of Ycombinator for some time. I have been researching on this topic for the last 4-5 years. To be really honest I think TripHobo.com does not fit SomeCallMeTim's use case. I think Roadtrippers.com may fit the bill. Having said that, I am a big fan of TripHobo.com. I have seen the portal evolve for sometime and I see it as the closest solution to fixing travel planning I have my reasons here: 1) The only source which gives you draft itineraries created by other users. This is immensely useful as i can see what other are planning to my destination. I planned a trip to Rome using TripHobo.com and i find it immensely useful.. 2) If you hit Plan my trip button, the TripPlanning functionality is awesome. You can add almost all attractions in a city to your trip plan and you can hit the optimize button, you get an automated route planned. What TripHobo claims is that the route plans generated are not only optimized for distance but also for opening and closing times of attractions. I think this is really cool. No one does it so easily.. not even google! 3) The ease of usage: This is the most easy to use portal for trip planning.

Limitations: I think there is only one limitation as SomeCallMeTim pointed out.. Limited number of cities .. I counted the number of cities manually in August last year, i could find 171 cities to which i could plan trips to. I counted again on 5th october 2014 and i found that there were 243 cities. Today i saw that they have changed their interface to a search bar and hence I am not able to determine how many cities are enabled on Triphobo.com.. If they go on increasing the number of cities to which one can plan his/her trip to say 3000-4000 cities around the world.. i think TripHobo.com will have fixed travel planning for sure. My 2 cents!

I am also tracking folks like roadtrippers, mygola and tripomatic. To me these (along with TripHobo) are the leading 4 travel planning players today. MyGola has been a disappointment..Tripomatic is difficult to use..Roadtrippers and TripHobo are i think getting some serious traction .. Roadtrippers has primary focus on roadtrips whereas TripHobo is a holistic leisure travel solution if they are able to scale their content..

Hi there, I'd love to hear why you think that Tripomatic is difficult to use. If you don't want to write it here, could you get in touch with me at barbora@tripomatic.com? Thanks a lot!

This exists, just not as a web app- your local AAA will gladly map out a road trip for you complete with the locations of gas stations and attractions along the way.

Triple-A does a lousy job of planning out road trips.

My girlfriend insisted for years on how great Triple-A was and wouldn't take any of my suggested routes (I live for road trips, I've driven all over North America). Triple-A routed her from South Dakota to North Carolina via every toll-road and congested interstate there was (Chicago, Toledo, Cleveland, Pittsburgh). I said drive down to St. Louis and enjoy a toll-free drive through the Kentucky and West Virginian countryside. She went with Triple-A's route on the way out and spent who knows how much money on tolls just to sit in Chicago's traffic. Took my route back and got a beautiful ride through Appalachians in the fall.

Loved this post - for any others here who share similar views, thought I'd share a few thoughts from our experience working on this.

I'm co-founder at https://www.wanderant.com. We started off with similar frustrations on planning trips. All the information you could ever want is online - and for free - so we should better off than where we were when you'd just buy a Lonely Planet book. But that's not the case, I think it's actually gotten harder - partly because there's so much info, and so many options.

We're a year+ into it, and have been iterating multiple times on an MVP. It's a big problem to solve, so 'minimal' is a bit high - plus it's a different minimal for every traveler you meet (e.g. comment here on "an option for children" which is absolutely critical for some).

Here are some things we've learned along the way:

* Top 3 things people need / want that haven't been solved:

- Local expertise - esp when traveling abroad - what is the local yelp / gothamist / etc? - Help with logistics - mostly around how to get from A to B - Rome2Rio is a great help in that regard, still takes a lot of work for planning an entire trip though - A way to manage a plan in one place - instead of email /bookmarks / excel

* Some of the challenges we've encountered:

a- Making a product that's easy to use - If you're only solving one step (e.g., online booking), it's easier to create a workflow that makes sense. I love examples like how hipmunk have simplified UX for booking flights. We are building towards a workflow that lets you keep your entire plan in one place - ideas, map, notes, reservations,... and finding a UX to make that easy is a lot of work.

b- Getting to a product that really adds value to planning- We want a tool that simplifies the process of planning. However, we clearly can't start with a product that does everything you need for a trip. Even in the near future, our product will continue to be an incomplete solution. So paradoxically, by being an additive tool in the process, we've successfully worked against making it simpler :) We have to make up for that by really adding a lot of value and saving time fr the user- and getting to that point is also a lot of work

c- Marketing is hard - others have mentioned the challenge of facing giants in the space- I'd like to offer another piece- which is reaching trip planners at the right time. Only a small % of people we reach are in the process of planning a trip. Then if they are, we most likely don't yet offer very rich content for where they're going - because currently our higher-quality content is still nascent. So that makes finding the right users hard. Any help here is appreciated btw - if you know someone who could use this send them along :)

* Why we're continuing - Times like this, when we see someone get passionate about how much they wish this existed or how they can't believe it hasn't been done before. We feel the same :)

- While it's a hard problem to solve, and there's a lot of challenges we already know of and more we don't yet - it is a really interesting problem to think about and try to crack.

- More than all, we love to travel to new places and explore the world. If we can share that experience and make it easier for a few others, we'd be ever so pleased.

As someone who travels a lot, I like your top three things, especially the first. Though taken alone that starts looking a lot like a directory of directories. One problem, as you say, is that there's a lot of information out there but it's uncurated and often based on specific commercial interests.

I just discovered Rome2Rio on this thread and it seems useful for things like whether I can take a train from A to B or whether flying makes more sense.

I use Tripit for much of my organization but it obviously only captures some things and it's format for displaying a whole trip is moderately awful.

Tripit looks to have had a reasonable exit before this article was written:



TripIt isn't a planning site, it's more of an organizational tool.

Correct. Once you're done planning your trip, you can send it to TripIt (or give TripIt OAuth access to your email) and it'll be organized in your account. There is no planning.

No true Scotsman!

Something clicked in me when I read the title & article: this is all true. I made one travel planner few years ago and decided to open source it some time later, when it become apparent that it's really hard to get decent traction with it: https://github.com/cwiz/GoFree

I'm not sure it's a matter of frequency, but rather a matter of value that the service ultimately provides.

Biggest concern with Google's business model initially was that they are "just a search engine" meaning they don't get as many page-views as portals. However Google managed to make more money than portals because ultimately they provided more value to the adviser (less impressions, but more targeted). At the end of the day, Google's service was intrinsically valuable - if they charged an annual fee to access the search engine, lots of people would pay up. The business model extracted that value, albeit in a different fashion.

You can't monetise trip planning with advertising indeed because there aren't enough users to make that model work. But if it's a valuable service - you should be able to charge a small fee for it. "We'll help you plan your trip for $10. Or $20 if you want us to put in some human effort". Given that it takes X hours to plan a trip, and a user's average wage is $Y per hour, some number should make sense. And of course the service would generate leads and other commissions.

Would anyone pay $10 for a service that planned a trip for them? I'm afraid not many people would, which means it's just not as valuable as people believe it is.

Up-market travel agencies plan trips for wealthy clients for free - there's plenty of commissions to go around - so that model works. Trip planning "software" however doesn't seem to provide enough value in its current form, but that doesn't mean it isn't feasible. If someone booked my flights, hotels, restaurants, tours, sight-seeing, theatres etc for a 2-week journey for me, they'd probably have a decent revenue stream from commissions alone (hotels pay 15%). Hell, I know a guy that plans trips for high-net-worth individuals and takes 10% of everything they spend.

I think the problem is that too many startups are afraid of the human element involved - having people make recommendations doesn't scale - they say. However a semi-automated approach, that gave you a real PA / concierge service throughout your trip would actually provide sufficient value imo. I know many wealthy people that would pay significant sums to have the whole thing planned (and booked!) for them in advance. Monopolise the up-market niche of VIP travel planning, before going mass market and you have a shot at a profitable business.

Well, I actually worked on Yahoo! Trip Planner (making it internationalised). There was zero engagement indeed, but everyone knew it was a crap idea then, at least in Europe. No idea how trip planner recruited ANYONE!

Yahoo is good at one thing slapping ads on content and making loads of money from it. Everything else they need to stop doing.

"In fact, Americans are notorious for shirking vacation, clocking the lowest rates of vacation on the plane"

That's because America is one of the very few 1st world countries without mandatory holiday time. 25 days of paid holidays + unlimited sick leave here in the EU are the required minimum by law.

Nope, sorry. That might be part of it, but Americans also are very reluctant to take vacations even when we have plenty of time off to use. In my experience it comes down somewhere between "things will fall apart without me" and "this is what I do".

I'm a (regrettable) example of this. I get 22 days off a year, and maybe take off half of that. I've usually accrued the max vacation we are allowed, so it just goes to waste each pay period. It's ridiculous, but its not caused by anyone but me.

>>I've usually accrued the max vacation we are allowed, so it just goes to waste each pay period

Sorry to be annoying about this, but in EU if you don't use your vacation time you have to be paid for it, at full rate. So it never really goes to waste, even if you willingly decide not to use it.

The other bad idea, local travel experiences, there were hundreds of them, but it's really hard to get critical mass, because you need to have enough experience hosts, experiences and then also visitors. The only ones that made it work were www.getyourguide.com who raised $14M.

I think its the classic chicken-egg problem like any other platform.

Yet the travel startups keep coming. Case in point: Travel blog Skift.

However, one trend I've noticed with travel review site TripAdvisor (which has been around for 15 years) is it's becoming a Yelp alternative. In that sense, it gets more of the regular activity that the OP referenced.

This fits perfectly with my startup food-chain theory.

In the internet startup world, there is an invisible food chain, whatever "higher" models will eventually "eat" "lower" models.

A travel planner, with low frequency, no real pain, doesn't stand very high on the food chain.

I'm curious about your food-chain idea. Can you explain it a little more and give more examples?

I don't travel a ridiculous amount, but TripIt is great and very sticky. Easing the pain of travel makes it worth your while. And knowing when I happen to be in the same city as a traveling friend is invaluable.

I have just used Owegoo.com for hotel and flights. Creative filters, not only A to B. Swedish startup, not perfect but a very interesting start. On www.owegoo.com they also have a lot of city guides.

No one remembers Dopplr? It was a pretty popular social travel planning site before Nokia bought them and froze it to death. It was like, one of the original web 2.0 sites alongside Flickr.

I had the feeling no one used Dopplr for vacations. Me and quite a few people I know input their conference and business trips, so with only a bit more traction it could have served "oh, you're also in $CITY, let's meet" quite well.

This was in Germany and a few years ago, though. With only tech people. Not a bad demographic, but there's probably a reason it got canned.

Dopplr went after the conference/business market, and at least in my crowd it had critical mass. That might be because I know the founders...

But it cracked OP's issue of needing daily use so you remember the service. I would check Dopplr to see which of my friends were coming to London -- that's much more frequent than me travelling, to the tune of travel_frequency * friends / cities. It was useful, and I still miss Dopplr today.

It feels like the author likes to see his family suffer and fundamentally misunderstands reality:

> everyone has the problem of not spending enough quality time with friends and family. Travel is the best and most meaningful way to do that.

Travel is an acceptable means to making it possible to achieve the end goal of spending time with friends and family, especially when separated by great distances. However as a means of directly spending time with one another travel is the most time-consuming and stressful way to do that; especially when you mix the ambiguity of squishy human sentiments with a rigid travel schedule.

And this is probably why nobody really gives a damn to use such things.

This is a lifestyle question and these are hard to generalize. It works well for me personally. 3-4 days someplace doing sightseeing, or maybe some outdoor activity is an accessible way of spending a few days with someone and having time that we wouldn't otherwise have. Many of my friends and family live in a different country. Flights and accommodation are affordable. Time is scarce and if we visit eachother in one of our normal lives, it's harder to find whole days to relax hang out.

A context for spending time together is (to generalize) a pretty good way of maintaining relationships, relaxing and having fun. You might have a friend, parent or child with whom you occasionally go fishing, hunting, bird spotting or whatnot. You might have an old army friend you meet every few years for something else. You might have a cousin you meet for a run once a week. Whatever the specifics, context for spending time together between people works in many cases.

Travel is a good context. It's accessible, easy to arrange and works for a lot of people you might want to catch up with.

I remember the sites to search for airplane tickets like Hipmunk, Kayak or Expedia, they have the recognition so perhaps they can add travel planning.

Cost to find and learn learn new travel planning software > cost to plan trip yourself with the internet

After wedding planning software...

How is the problem "If I don't remember it, I won't use it." solved?

Based on the comments to the article, this is a year old (still valid, just a bit old)

I failed a travel planning start-up in 2007. Way before our time, I guess.

> Americans are notorious for shirking vacation, clocking the lowest rates of vacation on the planet

As if they really have a choice in the matter.

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