Just about two weeks ago, I released my first paid iPhone app, Checkmate. The experience has been priceless, plus I made a few bucks as well. I thought I’d share the stuff I learned, both technical and otherwise.

Technical:

Core Location. Being the first iPhone app I’ve done that uses Core Location, I learned a lot about the process of starting up the location manager, filtering location updates and getting them to work in the background. The background stuff is pretty new, just released in iOS 4.

Design takes thought. One of the most difficult things in designing an app is balancing between user expectations (“it should work like magic”) and real-world constraints (battery, accuracy tradeoffs). I’ve taken the approach of leaving the details under the hood (another app that does something similar gives users full control) for simplicity. This is a deliberate design decision. I’ve found that many users are happy with the app, and some are unhappy. I assume there is a minority that is unhappy, but that they seem to be more vocal (more on that later).

Core Data. I also learned about Core Data, since I use that for storing venue data persistently. There’s a bit of a learning curve with Core Data, but I have a pretty good idea of how it works. I guess it helps that I’ve designed a bunch of database schema in the past.

Get to good enough. I definitely feel like I have accomplished something by releasing the app. I have wrestled in the past between releasing something when it’s “good enough” but not getting stuck in perfectionist limbo. In the case of Checkmate, I got to a point where I was happy enough with its performance (it works) and did not want to delay any further, lest I lose steam and give up on ever releasing it. Now that I’ve gotten a feedback loop going, it’ll be easier to improve and update the app anyway. As far as interface design goes, the app is a bit clunky for my taste. Having admitted that, I think I could go back and make some things more obvious (like the login screen) and polish up the user experience.

Business-ey

Ask for reviews. Ask satisfied customers for reviews. Because if you don’t, only the unhappy users will post them. And you’ll end up getting a pretty bad average rating. Even if your app makes crap into gold, there will be users who don’t see the value in it, or think that $2 is too much to pay. Encourage users to post reviews in-app and you’ll see a well-rounded view of what people think about your app.

It’s okay to have a competitor. While developing my app, I found that another similar app had launched and gotten some press from Techcrunch. This was a bit depressing as I wanted to have that exposure. I ended up using it as a motivator since the blog post and app validated my own idea. There’s always room for competition, especially if you can outdo them.

Popular takes all on the App Store. There have been blog posts on the subject of iTunes ranking and how valuable it is to make a top 100 list. Apps seem to be ranked in search based on their sales volume, which means that popular apps will become more popular. Having been featured on Mashable at launch, my app got to #2 for a “foursquare” search. This helped a lot for residual sales. I’m assuming that most apps are sold directly from app store searches. There are other ways to discover apps.

Have fun! It was really exhilarating to see my app get into the app store and into the hands of users. I set up a twitter account to communicate with users, monitored twitter searches for my app and answered emails sent through a contact form on my website. It was really fun having people react to work that I did. It’s probably one of the strongest motivators for me to keep doing what I’m doing.

I have learned a great deal from my first commercial app launch. I’m really glad that I had an idea and stuck with it to completion. I’m still learning a great deal from Checkmate. I know that this experience will make the launch of my next product/app (whatever it might be) more smooth, both for me and users!

My second iPhone app, Checkmate, just got approved in the Apple App Store last night. It’s an auto-check-in app that runs in the background. You select your favorite venues, and Checkmate will check you into them when you get close enough, even when the phone is still in your pocket! I wrote this app because I got annoyed at forgetting to check into places on foursquare while there.

If you’d like to get Checkmate, you can buy it here for the low price of $2. For more info, check out the official website I made for it. And follow Checkmateapp on Twitter for news on the app.

I recently read an essay by Paul Graham on what happened to Yahoo. In it, he describes how Yahoo acted like a media company when it was really technology company, and how funky management made it into what it is today. One quote struck me as relevant today:

By 1998, Yahoo was the beneficiary of a de facto Ponzi scheme. Investors were excited about the Internet. One reason they were excited was Yahoo’s revenue growth. So they invested in new Internet startups. The startups then used the money to buy ads on Yahoo to get traffic. Which caused yet more revenue growth for Yahoo, and further convinced investors the Internet was worth investing in. When I realized this one day, sitting in my cubicle, I jumped up like Archimedes in his bathtub, except instead of “Eureka!” I was shouting “Sell!”

Having just integrated iAd into one of my iPhone apps I’ve noticed that pretty much all of the ads are for other apps. Most of these apps are “free,” and I assume that they could potentially be using iAd for revenue as well. This is a result of low fill rates for iAd and Apple wanting to offer developers a way to advertise their apps. It makes sense, but one has to wonder exactly where all the money is eventually going (Apple gets a 40% cut of iAd revenue), and who has the incentive to keep that system running.

A while ago I wrote my predictions for iAd. I didn’t foresee Apple opening iAds up to developers who wanted to advertise their apps. That’ll help the fill rate, but I can’t see it helping CPMs when developers have something like a $0.25 CPC and it was reported that the larger media campaigns like Dove were closer to $2 CPC. Seems like another race to the bottom, just like paid app prices.

After reading this article on the upcoming iAd release, I have a few thoughts on the future of Apple’s mobile advertising platform.

iAds on Apple devices will be rich media experiences, they’ll stay in the app, and they’ll make developers tons of money. That’s what Apple assumes, at least. The major takeaways from this article are that only a limited number of advertisers are signing on at first, and at a really high premium. What’s more, iAds are costly to “develop” which will limit the number of advertisers at first.

Advertising relies on a steady supply of supply (advertising inventory) and demand (ad impressions). The advertisers supply the… well, supply, and the developers handle the demand by providing users who will see the ads. Because there’s not much supply yet, and because I have a feeling many developers will integrate iAds into their apps or already have, I predict a few things happening:

Users will go through a high degree of ad fatigue. With only a few different ads available, users will probably get bored of the same ads over and over. Sure, they’re rich and interactive, but if I see that same Toy Story 3 ad a billion times, it won’t be effective anymore. This will probably contribute to iAd blindness.

Initial advertisers will pay a premium for being first. Because of the limited inventory and abundant number of impressions, advertisers will probably end up using up a lot of their inventory. Apple might have a way of throttling ad impressions so they remain constant throughout a time period (or at least they should). If so, iAd display will be pretty erratic. Sometimes they’ll show and sometimes they won’t. Of course, if that happens, publishers will be upset that their placements aren’t selling.

Publishers (developers) will make some money, but not as much as they thought (at first). Or at least, not until the ad inventory goes up. Because Apple will probably throttle the advertisements going to them, or users will be weary of the same ads showing up, publishers will suffer at first. In the long run, publishers will probably end up making more when the supply and demand issues fix themselves.

Advertisements will probably start off being innovative, then fall in quality. I have a feeling they will mirror the app store apps. There will be many high quality ads at first, but once Apple requires a steady amount of rich ads, others will develop iAds for advertisers. The ad inventory quality will suffer because of the cost and time associated with creating high quality ads.

On a high level, I see a few early issues in the iAd platform, mostly the demand for ads outweighing the amount of initial advertisements. Over time, this will correct itself, but at the cost of the quality of ads delivered. Think of how the App Store degenerated into crappy mirror apps, etc. Apple would like to keep the quality of their ads high, but I can’t see this happening based on the number of ads they need to deliver.

This will happen because Apple is offering the iAd platform to all publishers (developers). If they had hand-picked a few to beta test, I have a feeling the supply and demand would match up. Apple knows they’re behind in the game though, so that’s probably why they’re releasing it to all developers. In the long run, I think the iAd platform will be a hit for advertisers and developers. Hopefully the level of ad quality doesn’t suffer so much that it affects the end user too much.

About two weeks ago, my GF got a refurbished iPod Touch from the Apple online store. The refurb was pretty cool, but it seemed to have a really low battery life. I made an appointment with the Apple Store App for the Genius Bar and the guy who helped us was really cool.

We explained that she just bought the refurb and it was pooping out after like 3-4 hours of use. The guy showed us some battery saving techniques (like lowering the screen brightness and turning off location services, etc). At this point I was like, “come on guy, I already know that!” Then he just gave us some paperwork to sign and a new iPod! YESSS.

The awesomeness here is that he didn’t question us like we were total idiots and assumed we were right. He didn’t make us do any stupid diagnostic tests to prove we were telling him the truth. This is what set the experience apart from others, like when I call the cable company and they make me turn my modem off and on, etc. Thanks, Apple! The only thing I would’ve changed is that I scheduled the appointment for like 7:30 and they didn’t get to me until around 8.

The new iPod is working a lot better, so I’m glad we went in to do the switch. In other news, I am thinking of getting an iPad, because (gasp) I was wrong. In the future I should probably forego the knee-jerk assumptions for new products before I actually try them out. I can probably just say I did it for the lulz again and go on to become the next John C Dvorak. The iPad is actually quite neat. Understanding the iPad HIG goes a long way toward appreciating it. I also wrote an iPad version of my other app, so I’d like to actually try it on a real device at some point.

Neat. I walked in and looked around at the unibody Macbooks (the white ones that are now more curvy) and checked the battery life on them. They apparently get something like 5 hours (when I unplugged them and the computer actually calculated) versus my MacBook Pro that gets like 2 if I’m lucky.

Then I walked around and noticed something:

Apple printed the backs of the cardboard cutouts! They’re in the same poses in the back as they are on the front! If the backs had been blank, I probably wouldn’t have even noticed. But Apple pays so much attention to detail that they decided that peoples asses must be printed.

It is likely due to this level of detail that Apple is succeeding where other companies fail hard. I don’t care what anyone says about Apple, they care more about the user/customer experience than probably anyone else out there.

Edit: Cool, looks like my blog got posted to from some hack blog called “PCWorld.” I will note that while it is easy to make dumb predictions about the future, it is even easier to go back and look at the incorrect ones. If everyone made accurate predictions about the iPhone, it would’ve existed before Apple invented it. Please keep the comments section nice, or I might pull an Engadget. My mom reads this, you know!

Once upon a time, I made a post about how the iPhone was going to fail. I did it mostly for lulz and also to try and get on the front page of Digg. Seriously, that post was diggbait! That was back when people still went to Digg and people still tried to get on the main page of Digg. The interesting thing is that post got a lot more commentary than other technology posts I made before and since then.

Today, I feel the urge to write a post about how the iPad thing will fail. This time, I actually mean it.

In essence, the iPad is just a giant iPhone with no camera, no microphone and no phone. What it gains in screen size it loses in a lot of core functionality. It doesn’t even really bother me so much that they took out important features. It’s what they left in.

The iPad works on the iPhone OS. This could be a good idea, except that they really didn’t consider that making a device four times bigger might introduce some design considerations. The iPad is quite literally a giant iPhone. Most iPhone games, etc (at least, those not requiring a mic or camera) are supposed to work on it. But when you think about it, what games using the accelerometer will actually work out of the box when you’re dealing with something 1.5 pounds heavy and clunkier than a handheld device? Shaking a tablet is different from shaking a small phone.

I’m not sure if the designers were just lazy or if they didn’t care at all about the new scale. The mail app looks like it was hacked into the iPad. It should look like it was designed for the thing, but for some reason we still have the really thin column and a bunch of whitespace. WTF?

I suppose that Apple needed to release the thing and do it with an unpolished product. Some apps look well designed, like the iBooks one (clever naming convention there, Apple), but most look like they were just stretched to fit the larger resolution. A lot of companies could get away with this, but I think people expect more from Apple. If Apple wants to control the entire end user experience, they should take that responsibility with a burden.

My predictions:

• Apple will get better at designing apps for the iPad. The best ones will come from them.
• Most developer apps will look like crap on the iPad. A few will “get it.” Those ones will be successful.
• Most developers will probably find developing (quality) apps too difficult on the damn thing, give up.
• People will realize that they don’t want a computing device that only allows Apple-approved software on it. They’ll stick with the Macbook, which can do much more than an iPad and runs any third-party software, including Flash and Firefox.

There’s been a lot of talk lately about proprietary platforms. Apple has been rejecting apps left and right due to various reasons. For example, they rejected the Google Voice app using their generic “duplicates iPhone features” reasoning. Isn’t that kind of reasoning grounds for an antitrust case? They also rejected a dictionary app for potentially bad words! Someone think of the children!

While I think Apple deserves some credit for popularizing the whole app store notion, they also kind of suck for holding such an iron grip on it. It’s nice to find apps in the store without having a third party directory or searching for apps all over the mobile web. But it sucks when honest developers get screwed because of totalitarian control.

I wonder if there can’t be a nice, happy medium. Maybe an app store combined with a way to legally (without jailbreaking) install apps via a third party. For now, the iPhone’s App Store is great for customers, but I have a feeling that abused developers will eventually learn their lesson and go elsewhere.

So there was this Microsoft ad that came out during an NCAA game. It featured a cute girl, Lauren, trying to decide which computer to buy. The voice of the ad (some omniscient being?) told her if she could find the kind she wanted under $1000 he’d buy it for her. The computer she wanted at the Apple Store was too expensive. She chose a Windows PC instead for $700.

A lot of people have claimed the ad is a huge success. It hits Apple in its weak point: price. That may be true, but there’s also this thing called “value.” Apple computers have always been about quality. Software quality, build quality, design. While it’s true that the upfront costs of a Mac are higher than a PC, you get what you pay for. There are tradeoffs associated with buying an HP versus a Macbook. The specs are not the computer.

I would argue that the amortized price of a Mac is probably about the same as a PC (or better). They’re built to last (even if Apple forces you to buy a new one every year or face inferiority). I’ve gone through too many Dell, HP and Toshiba laptops whose hinges explode. You can’t use a laptop after the hinge explodes. I haven’t had a Macbook explode yet (though the plastic did start coming off; it won’t happen on my aluminum Macbook Pro). Dell is trying to get into the premium PC market, which is great. But that sorta negates the price argument. In this economy it’s smart to play the price card, and people pay more attention to upfront costs than maintenance costs.

Also, it’s not the best idea to try and sell your product by having a “real” person shop for PCs when the person turns out to be a professional (SAG) actress. It makes it seem more staged; this definitely is not a Pepsi Challenge. But hey, whatever. I think MS got their point across. Plus I forgive Lauren because she’s way cute! I just hope her back can handle lugging around a 17″ computer.

Personally, I would advertise netbooks since they’re super cheap and Apple doesn’t have an equivalent, yet.

Over the past few years, I’ve found myself in a number of situations where I’ve been rejected. I read an article via BoingBoing on why some people see failure as crippling, while others see it as a motivator. Pretty interesting stuff. I have the book on hold at the library. I guess I fall into the latter category as I haven’t really let my numerous failures drag me down.

When I was fresh out of college (for the first time), I got an amazing opportunity to interview at Google. If you were a CS major in 2006, Google was pretty much the holy grail. In my mind, it definitely was (well, maybe second to Facebook, but they never got back to me). Like many of my adventures, I wrote about this in a blog post.

Long story short, I was rejected. I think at that point I was a bit cocky and thought Google was a sure thing. You should never have a sense of entitlement; that leads down a pretty depressing path. Getting rejected was a good wake-up call that I needed to improve myself if I wanted to end up with my dream job. At the time I thought I had missed an amazing opportunity. This may have been true; I’ll never know what my life would be like if I had started working at Google. Looking back, though, I think the rejection was really a blessing.

Maybe the reason I’ve been able to rebound from rejections in the past was that they’ve always been balanced with acceptances. At the same time, I was looking at grad schools. Rejection after rejection (after rejection after rejection) came in. But luckily there was a acceptance as well. And it was the school I wanted to go to the most, with full funding!

During the time between my graduation (and Google rejection) and the start of grad school, I had some fun making random web apps like MapsKrieg. This actually led to an opportunity for me to work with a startup called LiveByCampus. It was a pretty neat experience. Who knows, it might also lead to another opportunity some day.

In grad school, I had a lot of fun trying to get internships at companies I thought were really cool. And since I was developing all these new skills, I’d get hired for sure, right? Okay, I actually tried to be a bit more humble this time around. For a while, I was very successful in replicating my previous results of being rejected by Facebook, Microsoft, Apple, Zazzle and a number of other companies that didn’t even bother replying to me to tell me I was rejected. I guess I was sorta in a slump again.

Then I was selected (along with my teammates Adam and Gaurav) by RPM Ventures to start a company over last Summer. I realize I haven’t really written much about Troubadour Mobile (our website is very outdated) on my blog. Perhaps I should. To make a long story short, however, Troubadour Mobile turned out to be the best possible internship I could’ve had.

Sidenote: There’s this psychological idea that people will look back at events and see that what ended up happening was the best thing that could’ve happened. I read about this in Stumbling on Happiness. In some cases, people who lost limbs ended up saying it was the best thing to ever happen to them. I don’t think I’m showing this behavior here, but I acknowledge that I could be. End sidenote.

At Troubdour Mobile I had an awesome experience in entrepreneurship. We started an actual company. We got stock certificates! We paid taxes this year! We printed t-shirts! We didn’t, however, get business cards. I guess we were too busy writing an awesome prototype application for the iPhone! I learned a great deal at Troubadour and had a blast.

While I was very happy with the company, I wasn’t sure if I could take the plunge and attempt to live off of a scantily funded student startup after graduation. So I once again began looking for other opportunities. And I still found myself with some rejection (isn’t there some kind of three-strike rule for getting rejected by Facebook?). But I had much better luck this time. I think that the Troubadour Mobile experience had a lot to do with it, but I’m not entirely sure. I successfully interviewed at Orbitz in Chicago (great company and city, btw) and then at Microsoft in Seattle (also a great company (and city), despite what I’ve written previously in this blog, hahaha!).

And so I find myself here in the present. I’m finishing up grad school and will be graduating in May. I’ll be starting as a Program Manager at Microsoft in September. Hopefully I’ll have some time off over the Summer to chill (I’m also going to SXSW with Troubadour Mobile in a few weeks!).

It was through a series of failures and successes, rejections and realizations that I made it here. I think I learned something like a microcosm of this during my stint in entrepreneurship: you don’t just come up with a grand idea and implement it, making millions of dollars. An idea is prototyped and polished before it becomes successful. You come up with a million bad ideas, improving every time. In the same way, I learned from all of my rejections and improved myself along the way until I was able to land what I think will be a sweet job. Yet I’m sure that this isn’t the end of my failing and learning process.

So what’s the big take away? I think it’s that you can never be sure what counts as a true failure and what counts as true success. You can only try your best and keep adjusting along the way to try and get to where you want to be. Had I not been rejected by Google, I would have never gotten the chance to go to school at Michigan, meet many of the great friends I have now and end up with an awesome position at Microsoft. I can’t say the alternate universe version of me at Google wouldn’t have turned out better, but I can say that I am very happy with the way things turned out in this universe.

I also think a large part of success has to do with skill, luck and perseverance. While I believe I’m skilled, I also know I’ve been very lucky. While dumb luck helps a lot, I’ve also tried very hard to make my own luck. To me, this means creating opportunities, working harder to reach out to people and being proactive. You could wait for an opportunity to fall into your lap, but it’s always a good idea to try and speed up the process with a nudge.

tl;dr?

If you find yourself overwhelmed by what you perceive as failures and rejections, stay positive. Keep trying. Failures always come with a bit of information about how we can improve for the next time. And if you keep improving, it’s only a matter of time before you find success.