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 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.
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…).
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.
>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.
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.
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.
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
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.
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.
> 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.
> > 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.
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.
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.
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.
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...
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).
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.
Readit News
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.
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.
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.
Or of course a feature in AirBnB.
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.
In my region people abuse ig for all kind of use cases.
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…).
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.
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.
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.
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 may not be thinking of a representative sample of people.
it seems like most travel planning software fails due to the too-common misapplication of technology to solve marketing problems.
Source? That doesn't fit my experience
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
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
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).
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?
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.
Small(ish) request, can you add weather info in there? Always super important to know to reshuffle activities properly.
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...
"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.
> 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.
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.
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.
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.)
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.
- 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.
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?
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
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.
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.