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Travel planning software: The most common bad startup idea (2012) (garrytan.com)
236 points by domrdy on Sept 10, 2021 | hide | past | favorite | 164 comments



I had founded Flights With Friends for group travel planning shortly before this post. I read it when it came out but knew the point about travel being rare wasn't the cause of these product failures.

The trouble with trip planning software is that making one that is 10X better than just planning it manually is very, very difficult. People love thinking about their trip and online tools don't make that more fun for them.

If someone made a tool that was better than planning your trip in your head it doesn't matter that you aren't taking a trip all the time. Because most people are always planning their next trip in their mind.

I thought I had something that made it better, but I was wrong. A couple of years later I pivoted to Suiteness to focus on just the part that worked best – selling suites and connecting rooms that hotels don't make available online.


Said more succinctly: It's hard to make a successful product that reduces the time people spend doing something they love to do.

Some ways I could imagine addressing this and the problem the article talks about:

* Aim to make travel planning not easier (i.e. less time-consuming) but more fun. Treat the app more like a game or media app where users spend more time planning their trip by using the app in enjoyable ways. Put a ton of discovery and browsing ideas for things to do in it. Pinterest for vacations and activities. Basically Instagram, but with a "book this" button next to that pretty sunset photo.

* Focus only on the parts of travel that aren't fun. Haggling over fares, logistics, reaching consensus with travel partners, etc.

* Support use cases beyond just travel planning. If it's also a commute planner, or "what do this weekend in town" planner, it may get used frequently enough to stay in a user's mind.


Even more succinctly: establishing consensus should be fun in and of itself. People dont know what they dont know. They dont want to plan. They do want to daydream.

Make voting addictive and make the tally results easy to interpret, and aggregated. Not only what restaurants got picked, but a sum of them by type. Popeyes may have gotten 3 votes, but "Mexican Cantinas" may have gotten 4, albeit 4 different restaurants.

Things like "what cities I want to visit with my friends" may or may not change between years.


I was thinking "travel", "plan" ... these two words do not go together.

"Travel", "explore". "Travel", "serendipity"....


Then you would probably want to fold it into something like Lonely Planet or a Rick Steves property.

Or of course a feature in AirBnB.


I love the Lonely Planet guides, but I don't like the budgeting that comes with them. I'd quite like an app into which you could say "I have a budget of $THIS_MUCH, plus or minus $THAT_MUCH for the day. I am in $LOCATION and I would like to experience $THESE_SORTS_OF_FUN_THINGS. Please generate, perhaps pseudo-randomly, an itinerary of fun for the next $NUMBER of hours with all that in mind".


One of my favorite things to do is explore a foreign city with a recent Lonely Plant book to guide me. I think there’s something fantastic about that experience that can’t be replicated by an app or website.

When I’m traveling one cool tech thing I’d like is an AI assistant that could actually place calls in any language to book hotels, tickets, or just check operating hours for places I find in the guidebook.


I dunno. I am surprised that there isn't something like "walk score" for a "visit score" - especially one where the score is based on what you want to do on your visit.

I get that when you're traveling to a new city, you usually have an idea for what neighborhood you want to stay in. A lot of cities - there's only 1-3 neighborhoods that are walkable and good for tourists.

Still, I'm surprised there's not an easy way to see what things there are nearby with some sort of ranking order based on what things you want to do.


As someone who travels full time, Google's introduction of yellow blobs on the maps in the past year or two has been an absolute game changer for me. I used to look up the name of a known walking street and then try to make sure I'd mastered all that was worth seeing by doing the perimeter including ended up spending hours on alleys that lead to nothingness (car coridors or residential areas of 0 interest at the edge of the area worth exploring)

Now, I just make sure I've walked the yellow blobs and I can be sure I've seen it all. It's a joy.

Way less FOMO at the end of my trips as well.


what are these yellow blobs?


https://blog.google/products/maps/discover-action-around-you...

> As you explore the new map, you’ll notice areas shaded in orange representing “areas of interest”—places where there’s a lot of activities and things to do. To find an “area of interest” just open Google Maps and look around you. When you’ve found an orange-shaded area, zoom in to see more details about each venue and tap one for more info. Whether you’re looking for a hotel in a hot spot or just trying to determine which way to go after exiting the subway in a new place, “areas of interest” will help you find what you’re looking for with just a couple swipes and a zoom.

We determine “areas of interest” with an algorithmic process that allows us to highlight the areas with the highest concentration of restaurants, bars and shops. In high-density areas like NYC, we use a human touch to make sure we’re showing the most active areas.


Does Google track everyone's phone location with Android to be able to give traffic info? Well I guess similarly they track the foot traffic and can indicate where in cities there is extremely concentrated foot traffic ... I.e. perfect areas to walk and explore.


It didn't do much in terms of ranking or customizing things based on your interest but Niantic's Field Trip app was somewhat like that. I think if it hadn't been killed off it might have evolved into something like that.


Since you mention this, could you provide thoughts on our project if you have a moment?

SAFEROUTE: WALK ROUTING VIA BEST LIT PATHS: https://github.com/kineticadb/saferun/blob/master/start-here...

We're in the process of app-ifying this, though as a fun project and not a business. The idea would be to identify walking routes optimized by a variety of factors:

- best lit (for safety)

- most beautiful

- best mobile phone coverage

Would this be useful?


This would be really useful as an app! I moved to Washington DC back when illuminated pedestrian paths were in weirdly short supply. People were getting mugged on the National Mall in the dark.


Maybe a hotel "ig shop" would be a more popular choice.

In my region people abuse ig for all kind of use cases.


I disagree. Most people love to imagine vacations, but then they realize they have to pay for it. It's only a minority that is "always planning their next trip in their mind", at least where I live. We all have a vague idea of where we wanna go next, but going from vague idea to realization is not very fun for most people. Realization is fun, or at least should be. Tourism is actually dead, and most people feel that deep in.


I don’t find being a “tourist” is fun. It’s superficial experiences that aren’t the actual culture of a place and often are designed to take money from you as quickly as possible (Tourist Traps).

It’s also long lines, crowds, influencers taking selfies and vlogs, and, one of the worst things I’ve found: experiences designed to make it feel like you’re a “baller” having a special night out. These will be 3 star quality experiences that are charged at 5 star prices. How much you paid is almost supposed to be a bragging right.

But the problem is, getting “off the beaten path” only works for so many people before the beaten path changes. Same with “the best kept secret” or “local hangouts”. These can only take so many people before they are no longer a secret or the scales tip to no longer be for locals. And blogs about unique experiences at a place work, but then fall apart if too many people do them.

Don’t get me wrong - tourism has its place, and I appreciate doing the classic “tourist” stuff at certain locations. But my best meal in Paris? A restaurant counter off the beaten path. The worst? A top 20 Yelp restaurant where they routed us to the tourist dining room filled with other Americans looking for a quintessential Parisian experience.

But finding a few locals to make solid recommendations would be quite useful before going to a new city. Google maps is good for that, but we still miss certain things.

Lastly, it’s extremely beneficial to know what to avoid and what to seek out in a given location. Like some people may not know that there are certain months to get crabs in Maryland. Or that crawfish season is in the spring. Or that, like an idiot, you shouldn’t order a lager off the menu at a restaurant in London without knowing that you’re about to be handed a £5 can of Brooklyn Lager from their imports (we could not find a local pub, and I could not find local beer…).


You know, even if you go “off the beaten path,” you’re still just a tourist. Just one who is “off the beaten path.” It’s like the conversations about experiencing the “authentic” culture of a place. If you want true authentic, move to wherever for a couple years and just live it. I enjoy traveling and I almost never do touristy stuff, but I have no illusions about not being a tourist and trying to get some sort of authentic experience that only scrapes the top of a deep culture.


Most technology products that we have these days are more about form filling and response returning than empowering the user to succeed.

Want to go to Germany.. ok you're going to have to go and research the current climiate for if you'll be accepted into the country (Covid restictions), visa requirements (depending on your situation), go to google flights fill out a few forms, decide where your flight is going to go, filter out the bad flights (I.e. Spirit like options like Lufthansa), configure the search to include costs of bags, oh wait the flight doesn't exist anymore for that cost, or doesn't exist anymore. Now you have to do research on connecting through the UK.. does this require a PCR test prior?

Google Flight's view of this: Well we provided a few forms and options for the users to select we're done with the mvp.


The other thing is that travel planning is flexible and uncertain. Computers are inherently specific.

Creating a program that doesn't interfere with this "maybe we'll do this, and if we do this then the trip will be X days, but if we do that then it will be Y days" isn't easy.


Yes, doubly so if you have your own vehicle. You might end up visiting other countries on a whim.


>If someone made a tool that was better than planning your trip in your head it doesn't matter that you aren't taking a trip all the time. Because most people are always planning their next trip in their mind.

My wife uses Travelocity's "book a random room" feature. You are told "random 4 star hotel in X area for $x" that is typically $10-20 less than if you use Travelocity to book that same hotel directly. She loves it because she gets really excited about saving a couple of bucks. I get anxious because I don't know what I'm getting.


They have two versions of that:

One where you can figure out exactly what you are getting if you want. It shows you enough detail about the "mystery hotel" (Example: Free Parking, Gym, At least 3 star, Rating of 8+ out of 10, at least 800 ratings) that quickly referring to the search results from the area makes it clear which is which. Love it and been using for years.

One where it's "One of these 3 specific hotels". I hate this one for the same reason as you because you're rolling the dice, the hotels can be very different and in different neighborhoods.


You should try rolling the dice with VRBO. Nothing makes a trip real like showing up half way across the world to find you have rented a flop house. Seriously, VRBO is a scam factory since there is no customer support or dispute system. Premier hosts can post anything, get paid, and never have to worry about getting docked for the scam unless someone rounds up some lawyers.


> most people are always planning their next trip in their mind.

You may not be thinking of a representative sample of people.


i once produced the annual catalog for a traditional travel package company, filled with pictures and enticingly-crafted copy (at merely-high to outrageous prices). the whole thing was designed to move potential customers from rational to emotional decision-making and apply simple price discrimination mechanics to maximize revenue. low tech but effective.

it seems like most travel planning software fails due to the too-common misapplication of technology to solve marketing problems.


So what I hear you saying is that instead of software that plans a trip people might want fun software to organize the trip they had already planned? Maybe with automating some boring tasks.


> Because most people are always planning their next trip in their mind.

Source? That doesn't fit my experience


The few times my plans get complicated I just use my OS included notes app

If I’m with someone that wants to make spreadsheets and calendars, I’m letting them do that on their own and either like them enough to go along for the ride, or go my own way completely


Oh boy -- I'm the cofounder of Wanderlog (https://wanderlog.com), a YC W19 startup exactly focused on planning travel. And I've really read all these articles

This originally was big on Hacker News in 2014: https://news.ycombinator.com/item?id=8419658

This is really just the latest in a long list of articles about why travel planning startups aren't worth pursuing:

- https://www.phocuswire.com/Why-you-should-never-consider-a-t...

- https://paansm.medium.com/the-top-5-reasons-your-travel-star...

But we're still at it and have grown a ton over the past year!

- On frequency: I think we're underestimating folks' ability to remember here! If the product actually is good, people will remember it.

- On being a real pain point: It's true that people have many "good enough" solutions to travel planning, but travel planning tools have failed because the past products really just haven’t been better by enough than using Google Sheets -- they assume that people don't like planning, or that they plan a certain way, and try to save time and automate it. In fact, people _love_ planning and sharing their trips! The tool just needs to work around the traveler, rather than dictate

Still, it's instructive that none of the links in the 2014 post's comments work. Will we prove them wrong? We can check back in 3 years when this article comes back to the front page again xD


You don't have to be just better than google sheets; you have to be a lot better than google sheets while also not introducing significantly more friction. Ideally none.

I think the space is hard because it involves tying together a number of different functionalities many of which are rarely done well, some which have never been done well.

Good luck! (meant sincerely).


Kudos to you for pursuing something that a lot of people are saying won't work. That takes some character! Especially in a difficult time for travel.

Your app looks great. As a full time traveler / nomad for 10 years, I don't have much of a need for itinerary planning apps on their own. But I would love to have social itineraries, where I can follow my friends' itineraries and share mine with them especially for serendipitously meeting up at random points around the world when our itineraries intersect. Yes, I've got an abnormally large number of globe trotting friends, but there are entire nomadic communities out there who are eager for this feature.

Are social features something you've considered developing further?


Hi! I downloaded your app, and convinced a friend who travels quite a bit to download it, on the basis of this post. It’s pretty great!

We have one piece of feedback: the trip page is very spread out, so there is no good way to see a quick overview of my entire trip, i.e. in city A from days x-y, then city B, etc. Unfortunately, a single day takes up the whole screen. If there was some way to have a more collapsed trip view in the app, that would be awesome.

Keep up the good work, I’m rooting for you.


Neato, this looks great.

Small(ish) request, can you add weather info in there? Always super important to know to reshuffle activities properly.


This is on our roadmap! A bunch of folks have asked for it, and there are good APIs


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

One thing I think all founders/Product people should consider is that there are off label(so to speak) uses for everything.

Many many people use travel planning software as escapism from drudgery. This is an opportunity not just to sell them travel, but also anything that immediately salves their boredom. Maybe a weekend getaway, a movie night tonight, or a hot date with a hot <gender> this week?

In this case the off label usage likely is much more frequent than the real thing because as Garry says people do not take much vacation; but how often do they dream of vacations?-- all the time.

Similar could be said about realtor.com People arent there just to buy houses, but to dream of what their current house could be (that they cannot afford). So maybe they're viewing lots of houses with pools? Sell them an above ground pool and a luxurious lounge chair...


I completely agree with this, and I think the frequency with which people use Zillow is proof that there's a whole lot of advertising to sell around products that are aspirational, detail-heavy and very common for people to think about (vacations, buying a house/car, etc).

"Zillow for Traveling" is much closer to something that makes sense, but probably has a very small overlap with the actual work required to make a tactical planning application, which is extremely boring and probably bad to start out building.

I'm not really sure where to go with this, other than I would really love something that would let me zoom in on individual destinations and see what's popular / what "trips people do" that's a bit more guided than TripAdvisor / Yelp / Foursquare and a bit more of a journey than looking at ratings for individual things.


The more you lean into the "facilitate daydreaming" angle, the more you're just Instagram, though, right?


Maybe it's me failing to train the algorithm well, but my IG explore feed is pure trash. It's all kinds of junk fitness stuff that is just recycled content (accounts that steal and post from other accounts) .

Not sure how to un train it to find actually valuable content now


Working on something like this actually, with a few differences of course but that’s the gist. Email me if interested in giving feedback.


> > How often do people really plan trips? ... probably once or twice a year if you're lucky.

> Many many people use travel planning software as escapism

Heh yeah I caught that too. My wife plans many, many trips per year - but we certainly don't go on all of them, hah. The planning is a hobby in itself.


Fun fact. When Garry posted this, I immediately sent him the pitch doc for my company's travel planning app, which I was convinced had cracked the code and overcome the issue he'd written about. Surprise surprise, we hadn't. And 9 years on, neither has anyone else, perhaps apart from players that were already big in travel then like Tripadvisor, and Google, which has the scale to succeed at anything if it makes them money, which travel does given how deeply they can insert themselves into the transaction path.


This might get buried, but I'll put this idea out there.

Background:

I'm someone who has traveled fairly regularly (> 30 countries), with some trips comprised of solo backpacking across Europe or South-East Asia. I also think I'm really good at planning, which is largely about constraint optimizing and solving some version of TSP (traveling salesman).

The idea:

You're in a city. You tell the app all the places you want to check out. The app returns an itinerary, calculating TSP starting from your lodging, taking into account expected travel time, the times the places are open, lunch / dinner, etc.

I would personally find this really useful because it would replace hours that I spend optimizing my travels.


I also travel a lot, but by motorcycle.

Personally, I put everything interesting on a map, and make a custom route that goes through it. In cities, I make itineraries on the fly, based on my mood. I don't need to see everything - not in 2-3 days.

What I'd really need is a map that combines route planning (Google My Maps), marker collection (Google Maps), exploration (Google Trips or Wikivoyage), area weather (Ventusky), and average weather for the time of the year. Other niceties would include border control requirements and COVID restrictions.

I think that this illustrates how wildly different everyone's travel planning is.


That and identifying how you connect between the places. There is a major cost difference based on where you're flying to and where you're flying out of.


Several years ago a prominent SV individual (now investor) wrote why investors do not fund dating apps. Since then, several apps like Bumble and Hinge have had very successful M&A. So I don't think these blog posts are particularly valuable except to stop someone who isn't creative enough to break away from the typical path successfully.

I created a failed travel app which was pitched as "Tinder for Travel" (also an unsuccessful pitch as some people thought it was Tinder while you are traveling, but wouldn't that just be Tinder?).

The idea was not a travel app, per se. It was for weekend staycations, since I had the problem of coming up with an itinerary for the day if I wanted to go out and about. Where to go in the morning? Where to have lunch? What afternoon activity could I do? Dinner? These were typical annoyances I had every weekend so I figured an app would help.

The app was too broad, imo. If it were to be successful, it probably needed to start as a feature. One idea the app's co-creator Zach came up with was spots for the perfect instagram post. Personally I was thinking to narrow the scope entirely to, say, a weekend in Healdsburg (this would suffer from the problem Garry discusses, though!).

I believe there is something to the staycation idea, as it is exactly what you'd want on a vacation as well. It's too nebulous even after having thought about it for such a long time, but I'm glad I built it or I'd still think the vision was a perfect match for reality.

(Regarding the dreaming comments made by a couple of people: it may be true, but I've been told by family for whom I've planned trips manually that I do "a great job" -- they have no interest, and neither do I, about planning the trip but being taken along for the ride. So there's probably truth to both. People could certainly fantasize about their trip while using a tool to help plan it, even if it were years in the future.)


Again, I gotta nominate "Tinder, but for pickup basketball" as the most common bad startup (or at least app) idea. I get excited college students hitting me up with this nearly every semester, like clockwork.


That's not a bad idea, it's a good idea.

Maybe a bad 'business idea', in that it probably won't make a ton of money, but as a solution, expanded into other casual sports, it might make sense.

Pick Up BB has a lot of participants, who are not at the court at the same time.

An app where you tap a button and say 'Who's Up For Hoops' and it connects you with others, is a great idea.

You could work with cities to schedule the courts.

If there is a legit need, there's opportunity.

The challenge with such things is generating enough penetration that it becomes 'a thing' - so many great ideas I see would work really well if they did create a critical mass, and, of course, it'd be hard to make money.

I can see, in the future, these things working out.

A partnership with a famous baller, and perhaps with a sports drink or Nike or something, where they integrate it with Nike's 3 on 3 competition, you register for points, show your best moves etc.. It could theoretically work.

I wish we had better mechanisms for escalating these more niche apps into common public consciousness.


Add a self-rating system:

- Actually, I'm here for the beer

- Sometimes when I shoot, I score

- I have some moves

- I used to be good

- I am good

- Serious

and offer to either match people by level or build two teams that are evenly matched. After the game, ask people if they thought it was fun and if they thought the self-ratings were fair.

Later you get to add teams, quasi-teams, and leagues, if there's enough interest. But always start by asking if they want to do a pick-up game.


Yeah, I suppose I mean "bad" in terms of "getting the thing off the ground."


Just use normal Tinder, and ask every match to a date playing basketball! The problem solves itself.


As wisely said, “the ‘Facebook for X’ is Facebook”.


True, except for LinkedIn because you can't post your drunken ragers and be professional all at once.


You’d be surprised what has become popular on LinkedIn.


The contrapositive of "every website is a dating website if you try hard enough"


One made it to Shark Tank (no deal): https://sharktanktales.com/hoopmaps-shark-tank-update/


A relative is a librarian. She was recently asked for help using a dating site to find the patron a date to bowling league night. Some team of founders might be up for it...


I thought the inundation of "Tinder, but for X" was just something I was experiencing. Thank you for mentioning it.


I'm not sure I'd say it's most common but I'd nominate event ticketing as a common bad startup idea.


www.spontacts.com seems to have been around a while. I also wanted to develop something similar, for tennis (and badminton + squash)


The author doesn't seem to go into why travel-planning software is not successful, except for that it isn't discoverable since people only use it once in a while. I think the same can be said for a lot of services, like handymen (Angie's List)

One other reason is I think that travel planning is hard. Getting multiple people to agree on a destination, hotel, fares etc is all hard work. So most people only plan things with people whom they're familiar with, like close friends and family. If there's already a communication channel open like texting or Whatsapp etc it makes no sense to introduce more friction by having travel discussion go through a different channel. I remember an app for couple communication, Between. It had a similar problem. Why add another communication channel?


Surely there's a way to do it better than just over text? It's a 4-dimensional (time and space) experience isn't it: "After lunch on day 2 of the vacation, what attraction do you want to visit?", or, "When do we have time to squeeze a visit in that café that all the Instagrammers post about? [Yeah, like it or not this is the reality]".

A Miro[1]-like collaborative map would be interesting, every participant of the trip can vote what they want to see, the app can calculate the best itenerary (route and time), maybe even split up the group if some members are really not interested in some things (e.g. a visit to the local football team's museum, or the 5-star steak restaurant where there are vegan members).

[1] https://www.youtube.com/watch?v=pULLAEmhSho


It's more than a 4-dimensional space - it's a probability distribution over 4-dimensional space, one that you want to explore ahead of time, and you never really know for sure where you're on it until your trip is over. I'm yet to see a planning tool that handles this.

What I mean by the "probability distribution" part is, your trip plan isn't really a specific plan - it's a set of possible plans. You may have concerns like, "what if we arrive late on the first day?", or "what if the main attraction for the 2nd day is closed", or "we're not sure at this point where we'll eat", or "oh crap, it's raining today, what do we do?", etc. You have to navigate these questions in your head. I'd love to have a tool that makes this easier.


Ideally, such software should be tooling, not an all-encompassing platform.

I use Google My Maps a lot for trip planning. When I'm done, I can share the map with other people, or export it to my phone. This is good.

A tool like that that would also facilitate discovery and collaboration - a sort of Google Docs for maps - would be a lot more useful.


"Language learning apps are step 5 in the ten step process of achieving programmer hubris nirvana.

1) I'm in college and I'm going to build an app to easily buy and sell books

2) Off campus housing is hard, I'm going to build an app to find roommates

3) Splitting bills with roommates is hard, I'm going to build an app for cost splitting

4) All my previous apps sucked because they weren't social, I'm going to build a social network app

5) I'm bored partying with my new friends, I'm going to level up and build an app to learn a new language

6) I'm lonely, I'm going to build a dating app to find a mate

7) I found a mate and the whole engagement/wedding industry is a fraud, I'm going to make an app to make it easier to navigate

8) My children are awesome, I'm going to build apps to manage their time/friends/eating/sleeping/learning

9) Technology is a waste of time, I'm going to spend my time on other hobbies and my family

10) I've been working 20 years in a boring industry and I see an opportunity to write boring software that solves boring problems that businesses will actually pay for. Jackpot.

Edit: As others pointed out, should have included: ToDo app, Blog App, and a travel app. Travel should probably be 5 with language at 6."

From here https://news.ycombinator.com/item?id=15508239


Ouch. I literally did this. Built a site to buy/sell textbooks. Moved abroad, learned the language. Built a business to teach travelers the local lingo. 10 years later, it was acquired (at a loss). Currently on (9).


I generally agree with Garry's take on this.

However, I have used tripit.com before and it's quite a nice tool. You simply email them all receipts, booking confirmations etc and it automatically gets added to your trip itinerary. However, it doesn't seem like a super successful business.

The trip planning tool I need aggregates all my accommodation searches (Airbnb, VRBO etc) into a single place and includes all relevant details (rooms, bathrooms, location, features, price per night) and then allows multiple parties to comment. Currently we copy all listings over to a Google Sheet and share it with others. It's super cumbersome and I'd pay for a tool like this.


TripIt's been a great product for a long time, but not the kind of app he's talking about.

The article is referring more to pre-trip planning for leisure travel, which is a very popular product to build but never successful. I've seen new ones pop up each year since I started working in travel 10+ years ago, and none has ever achieved scale.

FWIW TripIt was acquired by Concur in 2011 for about $100M, so it was seen as valuable, at least to Concur, as they were able to make it part of their offering to corporate clients, which generate huge revenues for them.


Yeah. After I read everything more carefully, TripIt which I use is more in the vein of keeping track of business trips than pre-planning. Which I mostly don’t need software for especially for personal trips.


I’ve used tripit for personal travel but it was a very long 2 week multi leg trip with 10+ flights so really needed the collation.


TripIt is owned by or at least integrated with Comcur which is owned by SAP. It’s extremely useful especially for business travel. When you have 3 or 4 trips in various stages of planning it’s useful to see what you’ve booked and what you haven’t.


Planing trip is soul-crushing for me. All my friends said they super excited when planing, i got completely the opposite impression. All these schedule disaster starting from flight departure and landing time, bad timing produce lots of wasted time, landing to a city at wrong time adds an extra night (lost unnecessary money). Bus schedule is also disaster, "is there any bus" anxiety. Unexpected events suppose to happen and lost more money. Yep, the "supposed to be the fun most part" so called "get lost" is not fun at all. Fun parts are only like 40-60%.


I’ve done the planning for our last few vacations (2x Scotland, Iceland, Maine, and Charleston SC) and quite enjoyed the research. The key for me is to NOT plan too much. Flights and accommodation, of course, but once in a location, I just list 5-6 things to do in a day and only expected to do 2-3.

A trip that needs highly coordinated planning (tour of Peru including the Inca Trail) got outsourced to a specialist.


Bad B2C idea because Most people travel occasionally and at that point they could just do it on email/whatsapp groups.

Fair enough.

But, then i also see how someone starting as B2C will easily be able to pivot towards B2B, and sell to thousands of travel agencies selling tours to people. These companies are planning travel (for customers) everyday, multiple times. A SW like this will really help them with with saving time, resources and communicate better with customers.

So not such a bad idea after all.


There are plenty of software companies in this space - much of the time the software company also owns the agencies... eg. TravelEdge. It's obviously an industry, meaning one could disrupt it etc, but it's not some untapped market.


Which leads us back to trip planning. How often do people really plan trips? For the typical working adult, probably once or twice a year if you're lucky. In fact, Americans are notorious for shirking vacation, clocking the lowest rates of vacation on the planet. Twice a year just doesn't cut it.

This is something I've thought about before. European friends I've met put a lot more thought into destination "discovery" than Americans do. From my own observation, Americans just want to go to places they've been to before(for example that yearly trip to Cancun or Miami) or to a place that theyve been invited to for a specific purpose ("my friend's wedding in Vegas"). In those cases most of the planning is already decided for you, and you only think of where you'll stay and what you'll do when you get there. Only a very small set of would-be nomads or people on backpacking trips seem to be interested in frequently planning new place discovery.

Before Covid though I did start to see more aspirational trip planning come up in casual conversations based on places they'd seen on social media. For example in the years before covid Bali was really well known among Europeans, but wasnt on many Americans' radar until they started seeing instagrammars photographing beautiful locations. Most talks were of the "would be nice" variety. These are my own anecdotes from talking to people of course, the only evidence I can think of is that there were no direct flights from mainland America to Indonesia like there were for Thailand, Australia, and Singapore. I wonder if there's a way for a social media savvy would-be trip planning startup to target people who follow and interact with travel "influencers" with messaging like "here's how you can make it to X, on $50/daily spend, within a time constraint of 2-3 weeks" I personally was inspired by a guest blog post on Tim Ferriss site many years ago.

https://tim.blog/2013/08/05/cheap-travel-in-paris-new-york-h...

Note: Im thinking in 2019 or 202X post-pandemic terms. Covid is a whole new level of trip planning complexity and ethics that merits its own discussion. You definitely cant go to Bali as a tourist at all right now.


This is a good observation. I don't know if there's a name for this psychological effect, but I observe it in many areas of life. The basic rule is:

The fewer future choices you think you will have, the more risk-averse you will be when making the current one.

You're more willing to roll the die and lose if you know you'll get more rolls in the future. Americans generally take fewer vacations than Europeans, so the opportunity cost of a single trip is higher. Because of that, it's natural to choose safer known vacations. Trying out someplace new and running the risk of it going poorly is harder to swallow when that may be your own significant trip in a year or two.

A European is more likely to gamble on a new destination because if it doesn't work out, well, they've got a couple more trips coming soon to even it all out.

(Also, there is the practical matter that Europeans have access to a much wider variety of vacations for less money because everything is smaller and closer. Americans do in fact vacation in a wide variety of places, but those are usually different states in the US, which is mostly invisible to Europeans. Most people in the US have visited a number of other states.)


I don't think this is a US vs Europe thing. There are a LOT of Europeans who go to the same exact beach in southern Europe every single year. Take any RyanAir flight from the UK to Spain, and you will see that the average passenger is not exactly the educated elite who have put a lot of thought into their trip.


This is a great quote!

I only have a finite number of slots in my brain. If I don't remember it, I won't use it.

Why do I feel like computer industry people turn a blind eye toward this? It may be that successful tech people have practically infinite slots in their brains, so they aren't sympathetic to us regular people that do not. An example is the common question "Why didn't you use [X framework] to do this?" as if the possibility of answering "because I didn't know [X framework] existed" would be absurd.


In no small part, because the "slots" don't seem relevant in many cases. I couldn't tell you my dentist's name right now, but it's there, saved in my phone in case I need care tomorrow. Travel planning sites would be forgotten on my computer as a bookmark. Etc.


You are supposed to be a full-stack developer (also a DevSecOpsManagerJanitorEverything), so that means all frameworks for all possible parts of the application.


Omg. What a crazy article.

20% daily retention? Daily usage?

If I have an app on my phone that I open once a quarter and it delivers me a ton of value => I will happily pay for it monthly.

The travel planning does not provide such value at least to me. I’m already spending a ton of money on hotels, planes and transport as well as I do my research before the trip. Somewhere along this journey and from this money I spend on hotels and stuff there should be this service to help you plan your trip.

Update: i remember maps.me had this in their model - they wanted to sell you guides on the platform that you can then go through with GPS. Nice idea, but it had to be subscription so that user could explore these options as he prefers, not after buying the guide…


I cannot imagine airbnb having a 20% daily retention, yet they seem to be doing fine.


I agree that travel planning is a common (and often bad) startup idea, but I disagree with the reasoning.

Part of the enjoyment of many trips, for me, is the planning. I get to learn about the city, see which places/activities I am most interested in, and gain some small level of insight into the location, the history, the culture, etc. I enjoy talking with friends about what we want to do while we're there, or asking what they liked last time they visited, so I don't feel a huge pain point here. There are certain aspects of travel I don't like planning, such as transportation, but that seems to be where travel startups have been most successful (booking flights, etc.)

Similarly, travel apps don't know what I like. A museum about a certain artist that I'm interested in? Great! A concert for a musical genre I don't have strong opinions on? Meh. And while the software could take my interests into consideration, inputting my preferences to useful levels of detail adds friction to the process.

Finally, I prefer my trips to be flexible. I rarely plan what restaurant I'm eating at; I'll walk around and see what looks good when I'm there. And if I see something near where I'm staying that seems interesting, I can do that instead of whatever I had planned for that afternoon. Travel planning generally strikes me as more limiting than freeing.

Perhaps there is something great that just hasn't been created yet, or maybe my travel needs are sufficiently unique that I'm just not the target market, but I'm not holding my breath.


Been there, done that unfortunately - long time ago. Pivoted to selling experiences Sold by adventure SME. Was impossible to scale as each needed support to get their adventure itineraries online.

Painful.

Travel planning seems to be common wrong idea and the other is dating websites.


What's wrong with dating websites? The only thing I can think of is how saturated this space is


Ok, but why the @#% doesn't Facebook make it easy to know which of my old friends are living in cities I visit? I swear that would be the one obviously useful thing about Facebook.


The craziest thing is they used to make this easy with the social graph search or whatever they called it. Now if it's possible it's really hidden.


There is a nearby friends map, but it only works for people who have consented for Facebook to track their location 24/7.

I've played around with building an app that uses the Facebook API (and other social networks) to get people's current "Lives in" city, and location updates from recent posts, and aggregate them all in a map. I found it a bit hard to get this information from the APIs, and never had the time to figure out how to get it to work.


I dislike FB sooooooo much. It sucks all the air out of the room for online social engagements.


I would have thought it's to-do/kanban or note-taking apps (but with some One Weird Reason they're different and about to take the world by storm). Which interestingly enough is not at all like the reasoning here - they're pretty sticky, or at least until you move on to try the next one - there's just so many of them you're going to need much bigger scope to even start to think about making any money at it. (e.g. Notion has legs, but it's both to-do/kanban and note-taking, and also database/CRM sort of thing. All the others I can think of are minor pieces of a much bigger pie - Atlassian, Microsoft Office or whatever Wunderlist fell into, Github, Gitlab, ...)


The travel app I want is "on the way". It shows you cool things to do when in transit from point a to point b that's only an X minute detour. Or decent food/coffee. Or...

It's frustratingly hard to search google maps/etc with a query like this.


Hmm, I think this is easy to do on Google maps. Put in your origin and destination, then add a destination, and search for what you want, the map will show you results along your route with the number of minutes detour.


This requires me to know where along the path to search. But that's specifically what I don't know


I’ve had the same idea. It’s a good one.


One past discussion:

Travel planning software: The most common bad startup idea (2012) - https://news.ycombinator.com/item?id=8419658 - Oct 2014 (180 comments)


It needs a 2012 tag. I was excited to see what Yahoo trip planner does, only to find out it was discontinued long ago.


I worked for Yahoo Travel from 2004-2011 including on Trip Planner for several years, AMA? If they were talking about the mobile app thing though, I don't really know about that, that was done by another group with our data and then AFAIK left to wither on the vine; Yahoo's mobile strategy wasn't ever clear and never worked out for the lower importance properties like Travel. Travel itself got turned into a 'magazine' property with just articles then fully killed after I left.

To add a little blurb about what Trip Planner was, you could make a Trip (yahoo login require), and you could share with your friends (I believe we had read-only or read/write permissions) and make it public or keep it private. A trip had two main parts: the plan and an (optional) journal.

The plan would let you add items such as a hotel or point of interest or restaurant from our catalog, your flight details perhaps, or just a city, and you could also add your own items if you wanted to stop somewhere not in our catalog. You could also add notes to the items, and schedule them. You could see them all on a map and do multipoint driving directions (which was cool when we did it!). You could add things from the trip plan page, or while browsing our site Y! Travel was like 1/3rd a booking frontend for Travelocity and later someone else, 1/3rd a travel guide like TripAdvisor, and 1/3rd other stuff like Trip Planner; the travel guide section add links to add stuff to your trip plan or view other people's trip plans that had that stuff in it.

The journal was more or less a blog thing; text and pictures etc. Some people would work on these while on their trip, but probably more would fill it out when they got home as a way to kind of remember and share their experience.

Public trips had a comments section (optionally) and there was a 'like' button, the owner could add tags, but others could also add tags. All the web 2.0 junk.

Courtesy of the Internet Archive, here's someone's trip that was highlighted at some point: their trip plan https://web.archive.org/web/20111027022849/http://travel.yah... and their trip journal https://web.archive.org/web/20111103064256/http://travel.yah...


Apologies. I will add the correct tag next time.


This was my first startup idea. I started digging into it in 2010 with the idea of making it more sticky by "step 1: plan your travel around the attractions you want to see. Step 2: We'll show you the best hotels close to where you really want to stay. Step 3. Book! Step 4. Take your pictures and upload to our app, and we'll make a website for you that your friends will want to track, and you'll come back to with warm memories." Basically, social network cross blog cross build a community. The idea was to tie into local experiences. (Back then, the travel affiliate programs were a bit better.) Unfortunately, it was bigger than what I could do as a solo developer back then, and I wasn't in a place to court investment, and realistically speaking, it wasn't worth investing in once I started doing the cost / revenue business model.

I think in the next few years, this might get toward what a solo developer could reasonably support for a dedicated community, moving into the lifestyle business arena. I think the real value is getting the community of frequent travelers and optimizing for their experiences. There's a giant travel influencer segment now and cross-promotion is where it would be.


Like many here I also had an Trip Planner idea, also because I was solving my own pain point, to accurately create a feasible schedule for trips. My MVP (which is actually my travel planner) is a simple Google Spreadsheet that uses Google Maps API to calculate drive times between destinations (I like to do car trips). So i simply use it to put each destination, calculate driving tim and time at destination to fit the most destinations inside a day. It could become a product if it had access to a huge destinations database (like tripadvisor, Gmaps, etc.) with infos like "estimated visiting time", cost, etc... But I came to the same conclusion as Garry, this wouldn't be something that would appeal to many people.

Here is the link for the spreadsheet for the curious (you'll need a Google Maps Api key): https://docs.google.com/spreadsheets/d/16T9kLpbqciKCLNWOoOV1...


I often wish there was better trip/adventure planning software for the things I want to do for the next three years. Many things are cyclical (annual), or seasonal, or when I’m in certain places (I have lists for when I’m in LA, or Berlin). Keeping track of all the opportunities I care about along those 3 criteria is a lot of manual work right now.

I do miss old school Foursquare, only somewhat apropos.


I wonder how a more competent form of Siri/Alexa/Home might change these market economics. If we ever come to rely on digital assistants for much more than the weather and turning on our lights, the problem of remembering goes away.

"Hey Siri, book me a flight to Vancouver for next January when prices are below $400"

"Hey Siri, show me my travel itinerary"


I've been ideating on a travel planner for a while, and one of my original ideas was actually along these lines. I figured I'd have to build out a full travel planner first, but then I found this (https://www.inspirock.com/) which kinda covers the planning part, and probably wouldn't be toooooo difficult to hook into a voice command


No stats on Yahoo travel usage, no stats on how many people love to work on the travel product idea, no stats on how common the travel product idea is, no data on the problem of 'spending enough quality time with friends and family' or how that relates to travel.

Also, some things I do less than travel:

* Amazon prime day sales (once a year)

* Christmas (once a year)

* Dentist (2/3 times a year)

* Get my car serviced

* Get my bike serviced


> Travel planning software: The most common bad startup idea (2012) <------

2012. Can you name a travel planning startup in the last 9 years?


2012. Can I name a <random category> startup in the last 9 years? Probably not.

Hipmunk is the only one to come to mind but it's from pre 2012


Personally, I think part of it is that it hasnt been done well yet. Everyone focuses on one problem instead of looking at the entire experience holistically.

A feature that rarely gets put at the top of the list is true collaboration. Traveling with just a spouse or with a group, multiple participants have different wants, needs, preferences, interests. Maybe one person is in charge of travel logistics, one in charge of food, one in charge of activity discovery.

There's not enough auto scheduling where you say "we want two days of rest, one day of museums, and to eat out 4 time" where it fills in the rest.

Good collaborative travel software needs voting. It needs a way for teams of people to make wishlists and then helps determine which will work out the best. Is it smart enough to notice between 3 people they picked 3 different mexican restaurants, so it should probably figure out which of those 3 is the best, or ask if you want to eat mexican 3 times.

Maybe everyone saying it cant work just cant see how great it could be. If it was Apple level "it just works" a group of friends might click "plan a trip" and swipe through some options for a while, JUST FOR FUN, and an hour later have a complex entire everything booked. It could even include some Splitwise/escrow functions. It could help you use the right credit card for the right purchase. It could help you maximize points across vendors. When I travel as a family, vs when I travel with friend group A vs when I travel with friend group B, the brand of rental car may change depend on the best available deal given our different memberships. Ideally, this software has everyones usernames and passwords and knows how to access loyalty only pages from the vendors. Theres TONS of little complex interactions in travel that could be abstracted away by smart machines. If you think a group spreadsheet is the answer, we dont have the same type of friends. I'm not unleashing an 8 or 12 year old on the master plan vacation spreadsheet, but they can swipe through Orlando options all day long.

A way for it to be "used every day" is for it to aggregate Yelp and Google Reviews, and local events and let you plan more than just out of town travel. "What are we doing before the concert on Saturday, do our babysitters have the schedule?" Another way to make it "used every day" is to just make it damn fun to use. Friend groups sitting around, swiping and daydreaming about dream vacations they might never take. Does nobody sit around and bullshit like "we should go to Florida." "I want to go to Nashville." "How about Gulfport." "As long as it has casinos." Then once an amazing trip is planned, impulse takes over and everybody says fuck it lets just do it. Vegas doesnt need to be the only impulse destination.


Every time we travel with my friends we use the best travel planning software ever: a spreadsheet. It's the only tool that can bring together all the features you need, while giving you the flexibility of having your own organization:

- maybe you want to list everything in one sheet, maybe you want to split the "established" and the "ideas" in different sheets

- thanks to the beauty that is the Web, if something looks interesting, or you need to keep a tab on flight prices, you can just put a link to the resource with some comments. Include the link to the PDF of a 2-day excursion if you want. Add photos. Anything, really.

- if you need to vote, everyone can just put their names in front of the proposals

- with Google Docs you can even edit the same doc simultaneously and there is one single link that always point to the latest version

I do agree with the fundamental insight of TFA: if you're only going to use it once or twice a year, you don't want to take days getting familiar with the tool only to forget about it the moment you come back. And as a developer/PM you can't have every single use case prepared.

Sometimes it's better to just let people self-organize instead of trying to sell them something that's not better for them.


>you can already build such a system yourself quite trivially by getting an FTP account, mounting it locally with curlftpfs, and then using SVN or CVS on the mounted filesystem.

There's no way I'm turning kids loose on a spreadsheet to tally their votes for a Disney vacation.


I didn't include that kind of users, because I'm not travelling with them. Just like you I wouldn't trust them with the main spreadsheet, but surely you can give them their own spreadsheet: they won't be participating in most decisions anyway, so it's not like you'll need to copy paste most of it


Don't want to be offensive but your insight is not really insightful.

Why?

Because it goes in totally wrong direction.

Most people don't want to work on stuff or plan the trip - they want to pick up the phone, tell what they want and have it organized. Organizing or even putting your wishes into some forms is work and that is not what people want ... they want to have VACATIONS and not fill in some application forms.

I work in insurance area - my business people would like to make forms so business owners can fill in what they have and what they need in some magic form and that software does the rest. Removing middle people who pick up the phones and moving work of filling in details to the customer.

I see it is not working because business owner wants to call someone, tell him "I have a bakery, I want insurance" and be done with it. Because he is busy making bread, he does not give a damn about your risk compliance process.

Last point is - people also don't want to pay the real price for what it takes to have custom vacations organized - that most people pay for all inclusive in some resort go to swimming pool, have Swedish table and they are happy with it, because they don't have to think about anything and they have all organized.

"All inclusive" is shitty vacation by my standard and I like custom trips but I go into so custom stuff that you don't have database for that because no one is going into those places because of what I wrote earlier.

There is no business in travel planning because it is people who are into custom stuff they want to do themselves (and don't pay) niche or get "all inclusive" and don't care about anything whales. Maybe there are some people somewhere in between but I don't think you are getting money out of them.


>they want to pick up the phone, tell what they want and have it organized.

Only because nothing better has come along. I know plenty of people who basically refuse to make phone calls. Cant order online, they will go to a different restaurant.

>Organizing or even putting your wishes into some forms

Exactly why it needs to be swipes.

Open the App

Invite Friends

Swipe Destinations

Click on destinations to swipe activities. Restaurants. Pretty pictures.

If its more complex than Tinder or TikTok or Pinterest youre right it wont be FUN to use. The whole point is that the act of planning itself should be pleasurable.

People love endless feeds of pretty pictures.

The fact that peoples responses are forms and spreadsheets tells me I havent explained myself well.

It doesnt need to be travel only. I use Yelp and Uber at home, and away from home.


I don't know what is about swipes but those are underused I agree. Does Tinder have some kind of patent on swiping decisions?

What you describe here is in my opinion more interesting. Because that would be more like choosing which "all inclusive" most of people want. If typing is cut to minimum and as you mention there are mostly pretty pictures that one has to swipe left or right it might work.


Not only are swipes underused to build consensus, I dont even believe Tinder is the best example. Baby name apps are. A couple download an app, join a meeting room and swipe. Common names appear on a list.

Now imagine that a restaurant picker could determine whether you never want mexican or dont want mexican today.

Swipes are too often thought of as a binary left/right, when really they are more of a radial menu. Swipe left-up could mean not this time. Swipe left-down means never. Swipe straight up to signify something as to come back to. Swiping is easily 4 to 6 to 8 different outputs of vote. The screen should represent a different color for each one until you let go, so you know which option you are releasing on. Things like Maya have had radial menus forever. If you built true swiping radial menus, you can even have a second later of options once the first has been hovered over for a while.


I would not go into radial menu unless it is some kind of specialist app. I would cut it down to left/right up/down - yes tinder is quite binary and does not have "maybe" as an option.

Still you have to build database of choices which will cost quite some money.

Tinder has this upside that their database of choices is building on its own.


Technically tinder is already more than binary, as upswipe is a different form of positive swipe than right swipe. It works there. Theres really no reason that throwing a picture to one of the four corners cant work.


What about products for travel agencies? B2B that is...


I think there is quite cutthroat competition there already financed by people who own travel agencies.

You probably don't have a chance as an outsider.


You've hit the nail on the head, and I find it applies so many more things in life than just travel. It is my general observation that many people, as they progress through their life, reach the stage where they have more disposable income than time. And suddenly, all that tech fascination with self-service becomes extremely annoying.

I have personal examples from "the other side" for the cases you give.

Insurance-wise, I've been procrastinating on getting some of the belongings we have at home insured, because the insurance agent keeps coming back to me with calculations and offers I need to look at. But I have neither time nor patience to deal with it - especially not to study PDFs with tables full of calculations that were explicitly designed to be hard to compare[0]. The only interaction I wanted to have is, "this is where we live, this is the stuff we want insured, tell me how much to pay and where to send the money". They're losing money because they try to give me opportunity to save money[1].

Travel-wise, my wife and I both always looked down on people going on all-inclusives - but we took a chance and went on our first-ever all-inclusive a few years ago. We were immediately sold on the concept. It wasn't even a good all-inclusive - it was the cheapest one we could find, and the resort smelled like goats half the time - but it was the first time we actually rested. The amount of bullshit that goes into vacations is hard to even imagine until you experience being free of it. Even having to make a decision when, where and what to eat on a given day is a hidden source of background anxiety. On an all-inclusive, the only thing you need to worry about is what to do with all the worry-free leisure time you have.

So yeah, I agree with your conclusions. And in particular:

> people who are into custom stuff they want to do themselves (and don't pay) niche or get "all inclusive" and don't care about anything whales

Sometimes, perhaps often, those might be the same people. Personally, my all-inclusive experience convinced me that I should mentally separate the type of travel I want into categories. If I want to explore something niche, I'll continue to plan it myself. If I want to actually rest, I'll reach for the most bullshit-free all-inclusive experience I can get - as close as possible to "wire some money and be told what plane to catch".

(Though calling all-inclusive travelers "whales" is perhaps exaggerated - all-inclusives are ridiculously cheap these days, if you're willing to make compromises on luxury looks and you book far ahead in advance.)

--

[0] - Because, of course, businesses are douchy like that.

[1] - Or, perhaps, to fail at saving money - because, again, businesses are douchy like that.


> Good collaborative travel software needs voting. It needs a way for teams of people to make wishlists and then helps determine which will work out the best.

A few years ago we built this exact thing for an airline that you have definitely heard of. I believe it ended up being shelved due to internal politics/shuffling, but it encompassed everything that you described except non-travel/lodging scheduling.

The problem with these kinds of systems is that you always end up having to declare one person the de facto dictator/organizer (which effectively mimics reality), and the whole experience is perhaps overkill for groups of less than 6 people who would likely just conduct the informal planning over an SMS group chat.


I dont think group tinder for restaurants is that complex, from the UX side.

I dont see why there has to be a leader. Why cant it be a wikipedia style, "anybody can edit anything"? Or the option to have admins and just voting participants? If there must be a leader, why cant the AI be the leader? Or if nothing else, why isnt it just a pretty interface for tallying votes. "Oh, it seems going to a football game is way more popular of an idea than any of us expected."

It should also take into account events happening that overlap the trip. If I am there week A maybe football games are an option, but if we are there week B maybe its a country concert. Is there any good local event planning for groups software? It could be as simple as "What showtime works for everyone, where are we eating, do I need to bring anything." Structured conversation, that learns over time.


>Personally, I think part of it is that it hasnt been done well yet. Everyone focuses on one problem instead of looking at the entire experience holistically.

That's actually the exact opposite of the conclusion I came to. I think the do-it-all travel planner apps have never worked for me because there's some aspect of planning I want to do differently or some case they didn't think of, so I end up feeling like the entire product doesn't work for me.

The apps I've repeatedly used for travel are smaller or more general than just travel - I've used Splitwise a number of times on group trips (or at times even when a trip isn't involved) to equitably split costs. It doesn't do anything else, but it does its thing well. And I've certainly made use of a lot of shared Google Docs to collaborate on itineraries or packing lists, etc. I don't feel like I need a travel-specific chore coordinator app when I can just have a shared spreadsheet that lists which couple is making dinner which night at the ski house. There are a few web-based road trip planners I've used that seem to do a nicer job than just Google Maps for multi-day road trips with many stops, but of course not all trips fall into that category.

So yeah, I think a la carte solutions for different aspects of travel planning work ok for me - find a niche and do that one thing really well.


I built exactly what you describe at Flights With Friends. But the thing I learned is that group trips are not a democracy. Trips without a dictator who makes the decisions don't actually happen.

Building tools for the dictator is hard because getting the other group members who are not the dictator to actually use any tool is too much work. You are always dependent on the least reliable member of the group.

This is the exact reason that travel cost splitting tools don't work and the dictator just ends up paying for everything and getting the group members to pay them back. If they used a bill splitting tool the flights and hotels would sell out before the slowest member of the group put in their credit card.


As the self-declared benevolent dictator for several trips I've planned, I agree with a lot of what you said.

I've led a couple of great group trips to places I'm passionate about by emailing a group of friends and essentially saying "I'm going to go to X, here's what I think is amazing about X, and here are the proposed dates", and essentially getting folks to opt-in or not. Once the trip is locked in, there's certainly some discussion and folks say "I heard there's Y in X, let's do that!" and there's probably time to for that activity. But yeah, you need one master of the itinerary.

I do disagree somewhat about the cost splitting thing though - I've had several good experiences using SplitWise, although the groups have been relatively small - from 3 to 6 people or so. Maybe if you have more people, or weird family dynamics, or technophobes, it doesn't work out.


You are absolutely correct – Splitwise is great. I was thinking about the failed startups that did the splitting before the trip and then pay the vendors directly. Splitwise makes the process of getting reimbursed much better.

Also benevolent is the right prefix for dictator in this case. This person's reputation is on the line and they are working hard to make sure their friends/family have a great vacation.


There's definitely opportunity here, but at great - perhaps even prohibitive - complexity.

I'm not gonna sleep tonight, am I?


In 2007 I built a text highlighter service for the web. It was really as usable as it could be : you click a button and start highlighting text in the page. At the time social bookmarking was still relevant and my web highlighter was a better social bookmarking. But by examining usage patterns, I quickly realized it's a dead end : keeping things organized is work. Apart from nerds nobody would take the time and have the discipline to keep things organized outside the context of work. Once I realized that I knew del.icio.us which I was using every day is doomed. And I think that travel planning software is doomed for the same reason not because use frequency is low. Leisure is the wrong context for planning software.


My team is working on an AI powered travel planning app, which addresses some of the issues in the article. We like to invite hacker news audience to try it out and give us feedback. Download here https://unatravel.ai/una-travel-planner/


I believe such a travel planning software would have more traction if coupled with the local destination management system, as the locals (curators) would curate the information on events happening in the area, things to see & do etc. Then, you would just browse their website, and simply add things to your itinerary. Has an event been cancelled, or postponed? Bang, you would be alerted immediately and your itinerary would reflect it. You can't schedule a museum visit on off hours etc.

Without curators, which are locally incentivized experts, the traveler would have to work on getting and keeping everything organized. Some actually do like this research part, but most don't.

How do you bridge the gap between curators and travelers? For the 1st group, it's their work time, for the 2nd group it's supposed to be their vacation time. Kinda like a concierge service in some aspects.


The good version of this wouldn't be about making it easier or faster, it would be about making a sandbox for semi-structured social fantasy trip planning. Let people plan trips they may or may not ever take, just for fun. Like people create and customize characters in RPGs and The Sims just for fun


The article refers to leisure travel. There are multiple successful enterprise travel startups, such as TravelPerk:

https://en.m.wikipedia.org/wiki/TravelPerk


Similarly, if the best use case of your software is to help with trip planning, it is not going to end well either:

> At LinuxCon last year, Carl Symon showed me a screen shot of an Activity created by Aaron Seigo to plan his holiday, which included a To Do list, a calendar, links to online travel guides, a weather report for his destination, and other features connected to the trip.

https://www.datamation.com/open-source/the-mystery-of-kde-ac...


I thought it was task tracking software.


I haven't heard of anyone building this, is this what enterprise types are doing? Like a Jira or Monday.com?


Todoist, asana, Evernote, trello, etc etc. For a certain segment of society, services like these are perennially in demand, and there's always a new one promising a new twist that will actually keep you using it and transform your life.

Part of the ubiquitous demand for these services is because they're very useful, and partially it's because of how many people are sold on "productivity porn" and the idea that you can organize yourself out of being overwhelmed and ridden with FOMO anxiety (not on my high horse here: I've definitely been there).


10 years ago it was todo lists.


Still going strong, at least in my circles. Kind of depressing to see bright people inventing another app with a checkbox on its icon


Not too sure about this take. By this logic, the car industry would be bankrupt - people don't buy cars that often. Isn't the real issue that the spend vs. frequency is off? If I spend (on average) $1 a day on an app, that's a pretty good business. If I spend $10,000 every 10 year, that's also a good business. However, if I spend $1 every year, that's likely a bad business. It's not about how often, but how often as a function, with how much as the parameter.


Huh, I doubt cars is a good example. If I see the Ford logo every day as I pick up my car keys, and then it's under my nose as I hold my steering wheel, then when I buy a new car I'll probably consider Fords first (and maybe a terrible experience will make me avoid them).


And a great example of this? Airbnb. Pretty much disproved the entire post.


have used airbnb's planner - it's great. Admittedly, not in the past year - but then I haven't travelled, either.


The point, I believe, is that the car is the central thing you are buying; whereas the "trip planning tool" is an accessory to the actual thing you want (the trip itself).


The best travel planning app, by far, is Gmail.

I've worked in the travel industry and we'd work on tools for travel planning, and we'd get excited that you could put your itinerary together with just a few clicks. You know what's cooler than putting your itinerary in one place with a few clicks? Doing it with zero. Emails flow into Google, they get pushed to your calendar. Zero clicks and it's all in one place. Amazing stuff.


But that's not travel planning. That's just "creating a consolidated itinerary of the things you've used some other tool to do the travel planning in." (Which is sorta useful except that G Cal doesn't really create the events in the most useful format...)


It creates a central plan based on what I’ve booked.


This article made me chuckle. It is spot on. I worked at a trip planning startup around 2006 - 2007. A lot of money was burned, fortunately it wasn’t mine!


I was thinking the same thing recently for looking for a flat with a partner/roommate. A collaborative triage/kanban style system for reviewing/contacting/setting up a viewing would be great, but a typical user would only use it once every 1-3 years, and by the next time they need it, they may have forgotten about it, or it may be old and outdated by then.


Tell that to Pieter Levels, who's made a fortune off travel planning software as a one-man shop.


> Tell that to Pieter Levels, who's made a fortune off travel planning software as a one-man shop.

A "fortune".

He has a lot of little projects, what % of his revenue is his travel site/app? And how much?


I think in some ways this is also a question of specialized vs universal tools. If I plan a vacation with friends I believe I could do it 90% of the way just as well with a plain old shared word document/todo list.


anything new on this since 2012 you think?

Here's a bunch of previous discussion from 7 years ago:

https://news.ycombinator.com/item?id=8419658


I love that this was first posted in 2012 and it is still true today! The other common bad startup idea: parking apps! When I organized and facilitated Startup Weekends, we had one in just about every batch.


Besides the point in the article, I want to point out how good the writing is. The author captured me from the first sentence and I read all the way thru.


Maybe the simple answer here is that people don't want to use the same tools they use at work all year for planning what is supposed to be a escape from work?

Also...one of my favorite parts of travel is the spontaneity it affords me. I loath the idea of turning my free time into just another work day but with one-offs like "going to the museum" instead of "meeting with sales" embedded into some app....bleh!

Also...maybe no one has been creative enough to crack the problem yet, and someday someone will finally come up with a piece of software that is useful in this domain.


That's interesting!

Google's is very good, myself and my friends use it. Perhaps solely due to its tight integration with your Gmail and search.


It works for Google as they make basically all the money in online travel. Like, really, Google makes so much money out of travel, it's worth it for them to invest huge amounts on getting people to plan/book travel on their platform, because it just means more money for them.

The biggest players in online travel, Booking Holdings (Fmr Priceline Group) and Expedia combined spent $11B on Google advertising in 2019, which was about half their reported revenues that year.

The point of the blog post – that travel planning apps can't get user retention – doesn't apply to Google, as most people use Google every day anyway, so they already have the retention, and it's easy for them to funnel people into their travel section when they see a user entering travel searches into the main search box.


There seem to be a number of successful companies in the travel space... are they not actually?


He's not referring to trip planning as in Expedia, Kayak etc, those are trip booking. He's referring to tools that allow you to plan trips with friends (ex. Monday we are going to eat here, Tuesday take a trip here, stay at this hotel, take these flights).


damn I also have this bad idea before lol


youli.io is doing it, steadily gaining traction. Disclaimer: I built their mobile app.


I always thought it was grocery delivery or mail-order pet supplies.

There are honest-to-charlie geniuses out there. I think that the founder of Pixelon needs a giant trophy.


Instagram and Trello seem to be doing ok.




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