Hooray! Road Trip is available in the App Store now for iPhone, iPod Touch, and iPad.
I don't know that I've ever really written down the story behind Road Trip so now is as good a time as any. Set the wayback machine to August 2008! Apple had just updated what was still known as iPhone OS into version 2.0 with the App Store allowing third party development. I had picked up an iPhone in March but had found at the time that iPhone development was limited. Apple considered it a beta and getting the keys that let you put an application on the hardware was at their discretion and I wasn't invited to the party. So around July or so I had acquired the necessary certificates and was trying to figure out what my "Hello World" learner app would be.
By this point the Big Honkin' Road Trip (BHRT) was well established. A group of friends from my Kesmai days would gather somewhere and we'd travel around hanging out and visiting various local HOOTERS. Usually we tried to find a state where there on the order of three – six restaurants and visit them all, thus completing the HOOTERS of (state) tour. Our process for handling this was a little complex. Sometimes there would be a car rental, sometimes we'd have somebody's vehicle(s). There would be hotel rooms, there would be gas costs, there would be bar/food tabs. As different people paid for different items we'd constantly be passing back and forth cash as we tried to pay for things evenly. Mind you, sometimes we'd have six people on the trip with one or two others showing up for one stop or another. Plus there was drinking. We'd have somebody staying sober to drive, but that wasn't always the person tracking the cash. There were always these crummy morning reconciliation sessions where we'd dig up receipts and try to reconstruct who owed whom what. The previous BHRT I had used an OmniOutliner document to track every receipt and all of the outstanding debts. It worked but it was still a pain.
For some reason while Karin and I were at PAX in August it hit me: I could put an app on my iPhone to do all of this. At this point I had one week to write the app. This was the first version of Road Trip. I worked on it at PAX a bit, and wrote the vast bulk of it on my flight from California to Dulles to start BHRT2K8. It wasn't quite ready that night and I have some humorous memories of frantically debugging the math in Tony's car on Saturday morning because we needed the app to work before I started drinking. We all agreed that after I had been drinking I wasn't allowed to tweak our key financial instrument – this was really a refinement of an old MAMBA Kings rule where we could code after drinking at Fridays After Five (a little civic party that would happen in the summer that was a couple of blocks from our offices) but we never committed code until a sober review. (Indeed, you can see my key observation about that debugging session in a post on this blog.)
The UI for that version of Road Trip was hideous. It had this tabbed interface with no graphics, the first version couldn't handle splitting things non-evenly, there was some terribly confusing debt/payment nomenclature that was overly complex, and it was ugly as sin. But it worked. You could tell it "Oh Tony paid for a hotel room that Tim and Tony are splitting" and it would tell you how much each person owed each other. The core idea was offsetting debts: if I owed Tony $90 for a hotel room and I picked up a lunch tab so Tony owed me $45 then I'd still owe Tony $45. Now if there's a third person in that mix the numbers got more complicated but the app didn't care. It would tell you who owed the most money and they picked up the next tab. That would likely change the "Deadbeat" and we'd rinse and repeat. On the last stop of the trip we'd settle up and that would be the only time cash would have to change hands. We usually didn't have anyone owe more than $50 or so.
We used that version of Road Trip for several BHRT's and it slowly got more features, but was still ugly as hell and complicated. I was busy doing other paying work so Road Trip never got a through work over and I was never convinced there was much market for the application. Our trip to PAX East last year wasn't technically a BHRT but we did use Road Trip for settling debts.
OK, so last year my paying work stopped and I didn't have a great lead for something new. I decided to do iOS work and at that point why not dust off Road Trip and ship it? Maybe it won't be a big hit, but it's mostly done right?
Well, no. iPad had happened between 2.0 and 4.x and it really ought to be a Universal app. And the UI was just awful. And it really should have a map view, and maybe something about photos? Really the only thing that salvageable was the core math crunching. So the ugly Road Trip became Road Trip Classic and I started a new project, using iOS 5.0 (then in beta) and embarked on learning storyboards, the new iPad UI elements, and generally modernizing it.
And here we are way too many months later! I like the new UI and it even has some pretty textures evoking the key conceits of the app: money and roads. Maybe somebody will find this app useful, and at the very least we'll have an easy–to–use version for the next BHRT …
If you (or somebody you know) would find the app useful please check it out!