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I dunno... I have a $320 car payment and buy maybe $20 of gas a week, so I spend a lot more on my car than I spend on flights...

Now I guess if I could somehow spend that $4850 on flights that would get me maybe ten coast-to-coast round trips, which would add up to many more miles than I drive.

But how much of that spend is ad influenced?
1. Travel data is available so there's an incentive to work with it vs other problem domains.

2. Bajillions of dollars are spent on flight.

3. Affiliate (I think there's a better term but I'm blanking) sales are an instant revenue model.

4. Most interfaces to the data suck in one or more ways.

It's tailor made for data- or interface-strong team to make a financially successful startup.

1) true 2)also true, but flight commissions are at ~.1% according to my credible sources. And they are vanishing quick. My personal opinion is that it is a failed business model and as travel companies shift away from making money off of transportation commissions we will see more alternative forms of transportation. 3) Only when a company gets to scale are they able to make ANY money off of flights, and even then the number of queries they have to pay for from their data providers, server costs etc., bite deeply into whatever fee they make. and the fee is super small to begin with. 4) agreed completely, I elaborate on that. Disagree with your conclusion. Hipmunk several years out is still not profitable, with a great interface. A lot of flight travel startups are not profitable, so I don't see how you say this is the formula for a "financially successful" startup.
Monetize the car destination pathing.

With the site, the user creates their trip via car; businesses signed up for the service offer discounts for their services along the way; car driver wins, and is encouraged to stop at said businesses along the way; business wins, as they can easily market to potential customers and know exactly when they might be passing by, and can offer discounts to lure customers; site makes money from the subscribed businesses in one manner or another (there would be various ways to go about that).

Does this service exist? I've never seen it if it does.

I'm in the Seattle area. Suppose I need to go to Los Angeles. Let's consider the alternatives:

1. Fly. There are a plethora of flights on numerous airlines. I've got choices of extras (such as wifi in on the plane), whether I want to be treated like cattle or like dogs, how many stops, what kind of plane.

2. Amtrak. This is going to be the Coast Starlight, so really all you have to pick is your departure time, and what kind of seating you want.

3. Car. If it's winter need to check the weather forecast to see if you are going to need chains. Other than that, all you really have to decide is when to leave and whether you want to take I5 or go for the more scenic route down the 101.

4. Bus. Take the train. The train is about 15% slower, but the accommodations are better, and it costs less.

Of these, flying is the only one where I need help to reasonably arrange things. I can book the train in a few minutes on the Amtrak site. For the car all I need to do is toss my junk in the car, put the destination into the TomTom, and go. If I do decide on the bus for some unfathomable reason, it's a few minutes on the Greyhound site to book my trip.

I suspect, though, that most folks never even think of the option to take a mode of transportation other than airplane or driving. I've talked to a lot of people who seem genuinely surprised to hear that there's a train from Chicago to $city.

Figuring out buses can also be difficult. At least in the Midwest, there's very frequently a regional carrier that's a better choice than Greyhound. But they all have these vintage 1998 sites that are confusing to use, though of course before you can deal with that you have to first discover that the company exists in the first place.