Tag Archives: apple

Relying on Search

Most people don’t walk into a store and perform a search for colas.[1] They walk in looking for a Coke. They find the Coke and buy it.

If people are searching the App Store for Teleprompter apps, I’ve failed at marketing my app effectively. What I want is for people to go to the App Store looking for Teleprompt+. Or better yet, I want them on my web site, hitting the direct link to the App Store Page.

That’s how I know my marketing is working.

If the majority of your sales come from people generally searching for your type of app, you’re handing your fate over to App Store search, over which you have almost no control. Not somewhere I’d want to be, ideally.

  1. Or a Pepsi. Insert your favorite brand here.  ↩

Regarding the Latest App Store Rejections

We’ve been through cycles of App Store Rejections before. We’ve seen all sorts of strange decisions that we couldn’t comprehend. Sometimes they get overturned, sometimes they don’t. That’s life when you do business with Apple.

This time it’s different, though. This time, there’s clearly a conflict within Apple going on. I simply can’t believe that Craig Federighi’s team built all those wonderful new APIs into iOS 8 and didn’t intend for us to do anything interesting with them.

In Steve Jobs’ Apple, conflict in the senior staff was welcomed, even deemed necessary. In Tim Cook’s Apple, conflict is dealt with a little differently.

I expect one of two things to happen in the coming months. Either the crazy rejections settle down or stop, or a high profile executive goes on gardening leave.

The Wrist Business

I’ve been thinking quite a bit lately about the business side of Apple Watch development. After recording this week’s Release Notes episode, I wanted to further clarify my thinking on why I don’t think Apple Watch Kit Apps are a good place for me to be spending my time.

Let me state up front that I’m not telling anyone else how to run a business. You do whatever you think is best for you. I just hope clarifying my thoughts will help contribute to the overall conversation. Food for thought.

We know we won’t be able to sell watch apps at the time of the Apple Watch launch. So the value to our bottom line for making a watch app has to come indirectly. I’ve seen a few arguments now that this indirect revenue might be significant, and I want to address them one by one.

Some things I’m taking into consideration when looking at the following arguments:

  • First, that it will take me or a small team a minimum of a few months, if not a quarter, working on a watch extension to get it right.[1]
  • Second, any time spent on a watch component is time that could be spent on other improvements to existing apps, other new apps for iPad/iPhone, marketing efforts, etc. In other words, things that could be making me more money.
  • Third, I’m talking about right now. Does it make sense to build a Watch app today, given what we know and what we have at our disposal? All of this could change in a few months, years, etc. What I want to know is what I should be doing right now to benefit my bottom line.

You’ll gain customers you wouldn’t have otherwise had

I think the best case scenario for this argument is an app where the watch and phone are complementing each other very strongly. Apps where having the phone component alone didn’t solve the problem nearly as well as when you add the watch. I’m certain these ideas are out there, but I’d argue there are fewer of them than people realize.

Take Fin, for instance. An obvious watch component to Fin would be to allow the user to start and stop the timer with the watch. But is that enough to convince someone who hasn’t already bought it? Is that so compelling compared to just tapping the phone or iPad screen to start and stop? Wouldn’t that time be better spent making a remote function that would allow the user to start and stop the timer with another iPhone or iPad? After all, there are far more iPads and iPhones out there than there will be Apple Watches, and that won’t change for a few years at least. [2]

One of the first things Charles Perry told me when we both watched the keynote together was that Apple hadn’t presented anything that was better than what he already had on his phone. I had to reluctantly agree. Again, I do think there will be some apps for which adding the watch component will increase value significantly. I suspect the vast majority of Apple Watch apps, however, will be a small convenience improvement, at best. That’s great, and it doesn’t make me want Apple Watch any less as a customer. But does it drive new sales of my apps? I’m not sure.

You’ll make your current customers happy

Although your current customers have already paid you, and thus won’t give you any more revenue, the goodwill you will get from giving away this new watch functionality for free will net you money later through referrals to friends, etc. Or something to that effect.

David Smith presented this argument well on his Developing Perspective Podcast. I don’t completely disagree, but I also don’t see how focusing on a watch extension is a better investment than focusing on another improvement to one of my existing apps.

No doubt, getting watch functionality for free is nice for those who have already bought your app and who will be buying an Apple Watch as well. Do you know how many people that is? Is there any concrete way of measuring how many of your existing users will buy Apple Watches?[3]

If you have an email list of your current customers, you could poll them to see how many would be interested in watch functionality. Old fashioned. A bit messy. But doable.

You may find that although Apple ends up selling millions of watches next year, none of those buyers have bought or ever plan to buy your app.

Meanwhile, what about all the users of your app who don’t want Apple Watch and won’t buy one? Couldn’t you ultimately make more of your customers happy by adding a function to the existing iPhone or iPad app? After all, you know for sure how many people that would benefit.

The notion that a significant portion of your current user base will care whether or not you make a watch component is a massive assumption, backed up by no clear evidence. I like to trust my gut, but I trust it more when I have data that concurs.

You can charge more for an app that has watch functionality

If this were true, you could also charge more every time you add a major new feature to your app. But almost no one does that, and I suspect almost no one will for the watch, either.

I’d argue many of us could charge more for our apps in general. And I do charge more. Because I target customers who are willing to pay more. If you’re chasing a customer base that thinks 99 cents is expensive, however, you’re not going to have any luck raising your prices when you add watch functions. [4]

Apple has set up the WatchKit SDK specifically to restrict developers to free or at best freemium models. They are training customers to expect all software on the watch to be free. If you want to fight them, it’s going to be a long uphill battle.

I make my money on services, not the app itself, so getting on as many screens as possible is a benefit

No argument with this one. If you charge customers a subscription of some kind for cloud services, and the UI makes sense on a watch, maybe you should already be working on a watch app. I don’t make any of my money that way, but I’m thinking about heading in that direction very strongly.

Still, if your service is young, and your iPhone and iPad apps aren’t quite as good as they could be, the watch functionality might be something to put into the “nice to have” category instead. Depends greatly on where your current apps are, and how useful that cloud service is on the wrist.

Being there on day one will give you a great shot at getting featured by Apple

I think indie devs should stop chasing this dream altogether. For one, the majority of features these days are going to large companies who have direct PR connections to the iTunes staff. Or to indies who have a track record of getting featured, and thus the iTunes people are watching everything they do. If you’re a nobody to Apple, you’re most likely to remain so, no matter how successful you are financially.

You can catch Apple’s attention by doing something awesome. It does happen. But just building a watch app isn’t awesome enough. There will be thousands of watch apps on day one. And relying on the minute possibility that Apple will feature you is approaching your marketing from a position of powerlessness. You are letting Apple control your fate where you should be taking that fate into your own hands.

Also, getting featured isn’t what it used to be. It’s a sales bump, but you’re not going to retire on it.

Great innovations come out of experimentation, and you never know what the little thing you play with today might become

Absolutely. There is always a time and place for new ideas, for tinkering. But then there are the products that pay your bills. As long as you balance your time between those two things appropriately, you’ll be fine. If you drop everything in pursuit of the thing you want to play with instead of the thing that will help you succeed in business, you’re, as my co-host suggested this week on the podcast, a hobbyist, not an entrepreneur. That’s fine. The world needs hobbyists. And everyone needs a hobby. Just don’t expect to live on your hobby.

If the argument is that spending a few hours every Saturday tinkering with an Apple Watch app while spending the rest of the week working on other aspects of your business is a fine strategy, I agree. You may be better off researching marketing, or learning Swift in that time, but if it’s between tinkering with the watch or watching a crappy reality TV show, by all means do the watch.

Being first to market will give you a leg up over your competition

I refer you to this video from Dave Wiskus on the benefits of being first in technology. I also would suggest looking at the Twitter streams of many indie devs who struggled to get Today widgets into their apps on day one of the iOS 8 release, only to suffer from difficult debugging tools, changing APIs, Apple’s fickleness with approvals, rejections, rejections after previous approvals, and let’s not forget, the bug in Apple’s code signing that rendered Today widgets inoperable on day one. If you like living on that razor edge, be my guest. Just be aware you’re entering a world of pain, Smokey.

Even if you gain an advantage over competitors because you have a watch component and they don’t, how long does that last? How long before your competitors all make watch components, too, thus eliminating your advantage? Maybe you get some new loyal users out of it, but it’s short-lived, at best. Sounds like a small upside to me.

If you don’t do it all of your competitors will, and you’ll lose sales

This may be true. And it may be a good reason to work on the watch. But don’t kid yourself into thinking adding a watch component is going to make you more money in that case. “Do it or else” is avoiding something bad happening, not making something good happen. You won’t be getting more sales, you’ll just be losing fewer sales. You’ll be dumping months of work into maintaining your status quo, not building your future growth.

Ultimately, you may have to do that to remain relevant. That’s fine, as long as you see it as defense, not offense. Everyone has to play defense sometimes. But defense rarely puts points on the board.

In conclusion

I’m as excited about Apple Watch as any reasonable person can be. I look forward to owning one and to using all the great software likely to be made for it. I just don’t think the watch is going to become a significant portion of my revenue anytime soon, based on what I know today. So I’m choosing to focus the bulk of my attention elsewhere.

Again, I’m not telling you not to make watch apps yourself. You may have better reasons than I do to pursue this.

I’m also not saying I won’t be making my own watch apps—eventually.

Of all of these arguments, making money on services rather than selling apps is the most compelling to me. I think that’s the area where I’m most likely to focus my thoughts in the near future. I have little experience in that world, but I think researching that would do me better than building a watch app for any of my existing products. After all, a subscription-based service has potential to benefit my entire business, far beyond the wrist.

  1. Maybe I’m overestimating that, but from experience, I know developers tend to underestimate far more often than overestimate how long it takes to ship anything. If you’re pretty quick historically, go ahead and shorten that by a few weeks. If you’re David Smith, cut it down to 48 hours. But don’t lie to yourself about how big an investment of time it will be.  ↩

  2. And let’s not forget: getting people to not look at their watches to see the time while performing is one of the central reasons Fin exists in the first place.  ↩

  3. It would be great if someone came up with a way to do this in code. If I could drop something into my iPhone/iPad apps that detected the presence of a connected watch, then I could at least get a sense of how many of my customers would benefit. Not today, of course, because there are zero Apple Watch owners today. But at least for future reference. Is this even technically possible? Someone get on that. Seriously. Make it your OpenSource good deed of the week, if it’s doable.  ↩

  4. It’s tempting to think that people who buy an expensive luxury watch from Apple won’t be cheapskates about buying software. But you know better than that, don’t you?  ↩

Why I’ll be in Indianapolis Next October

We indie developers can be a pessimistic bunch.

Almost every week, there’s a new doom and gloom story brewing. One recent example: Monument Valley Forgotten Shores. Sold as a $1.99 USD in-app purchase (half the price of the original title), the new levels are insanely well crafted and allowed me and many others to rediscover much of what we loved about the game.

But a few hours into the release, Monument Valley was getting some 1-star reviews from disgruntled customers. How dare they charge another $2 for brand new content? You know the usual argument, if you want to call it that.

My reaction? I headed over to the App Store, gave the new version a 5-star rating (and a rare written review as well) to combat the complainers, and then I took to Twitter to voice my opinion, as usual.

In other words, let’s wait it out. Let’s see if these negative reviews are really anything to be concerned about. If they don’t effect the sales of the game, who cares?

But people were already convinced. Developers can’t win. Adding the in-app purchase was a mistake. Negative reviews will kill any app’s sales. Apple has made it impossible to make money on the App Store. No one values software anymore. And on and on.

Fast forward to a week later, and we get Daniel Gray, one of Monument Valley’s creators on an episode of Myke Hurley’s Inquisitive Podcast, explaining that the new levels are a hit. The negative reviews turned out to be a small minority of customers, and the game is selling better than ever.

In light of this revelation, how many of us indies are looking at this as a success story? How many are able to look past our initial anger and realize that this has proven that asking customers to pay for value isn’t impossible?

It’s so hard not to give in to that temptation to believe the worst whenever something goes slightly wrong for any of our fellow indies.

This is why I wanted to create a conference with Charles Perry next year. I want to be a positive influence in the indie dev community. I know I don’t have all the answers, but if I put the smartest people I can find into a room for three days and invite a hundred or so others to join us, I’m pretty sure we can all walk away with a much more uplifting outlook on what it is to try and make a living selling software. Because the success stories are there. Some of us are defying what the naysayers are preaching. And it’s not through magic.

The folks at ustwo didn’t get lucky. Their success is not a fluke. They built a loyal following with tons of hard work that went way beyond the product itself. Yes, the App Store presents a unique set of obstacles that we all wish weren’t there. But we can learn to navigate through them. If we can start learning the right lessons from these kinds of events, we can focus on building better businesses for ourselves.

Join our Release Notes Mailing List to get more information about the conference as it is announced. And join us in Indianapolis next October. It’s going to be enlightening.

Looking Up

The more I read from people I respect who have made a living in this industry, the more I realize that those who have succeeded at our thing are by and large the people who were patient, who didn’t take the easy way out, who built great products but also realized that wasn’t all there is to it, and who, most importantly, bothered to learn a lesson or two about business along the way.

I still have a long way to go.

If you spend 100% of your time just focused on the product, that isn’t going to cut it. A lot of developers have learned to make a kick-ass product over the past few years. That’s a great start, but that’s all it is at this point. A start. Congratulations. You’re now amongst thousands of others who bothered to do the product part well. Now what?

You need to be willing to accept that those people you hated back in your corporate days, the sales people, the marketers, the PR people, actually had an important job that brought value to the company where you worked. Hating them doesn’t take away from the fact that they were providing a service that your new indie shop now sorely lacks. Dropping an app on the Store that’s beautifully designed and superbly implemented is hard, and it takes a massive amount of effort to make that happen.

But it can’t end there.

Your product needs to get in front of customers. You think that’s going to happen because you got a mention on iMore or MacStories? Journalists provide an extremely valuable service, and their mentions can give you a great boost. But that buys you a few days, maybe a week at most. What I always ask myself is: What did you do after that to keep the momentum going? What did you do with that opportunity given to you by the press? What’s the long-term plan?

Most of us put the focus right back on the product. If it just had this feature or that feature. If this were just implemented a bit better. If I just work a little harder at getting the details right. Version 1.2 will be huge.

This makes sense. The product is where you’re comfortable, right? Me, too. I’d rather spend a week agonizing over a font than spend an hour writing an email to a potential ally in a related industry, asking to collaborate on a PR event. The thing is, product stuff is important, but focusing all your energy there is avoiding a larger issue: that you’re doing little to help people discover your existence.

People can’t buy what they can’t see. New features aren’t going to make you less invisible.

And Apple isn’t going to help you there, either.

The App Store is what it is. The competition is fierce. No special placement you happen to get temporarily is going to trump word of mouth generated outside the Store.

Either people come to the App Store already having heard of you and searching for your app specifically, or you’ve already lost. Discovery on the Store itself has for a long time been a fool’s errand. The VC-funded companies own the top shelf space now and will for the foreseeable future. Because they have people dedicated full time to this stuff.

The battle will always be won by the better marketer, the better business mind. The one who plays the long game. Not necessarily the better product. That’s a hard truth to swallow, but it’s been true since the dawn of commerce. Nothing about any of this is new or surprising.

By all means, keep making an awesome product. The product will need to be at least awesome to get you going. But then give it the marketing and sales strategy it deserves. I’ve failed on this front many times over, but I’m nowhere near ready to throw in the towel. There’s still so much to learn. I’ve been at it for years, and I’m doing better now than I was last year. And I plan to be doing better next year.

It’s always a hard time to be an indie. Because indie life is hard. If it weren’t, there’d be even more of us fools trying to make a go at this thing. (There’s a reason why steady jobs get to own you for forty hours or more every week.) Some times are harder than others, opportunities come and go, but the game is always the game.

And I plan to keep playing as long as possible.

Fin 2.0

About six months ago, I started using Fin to time my Chemex coffee brewing in the morning. Not exactly what I had in mind when I made the app, but it actually worked well for that initial 30-seconds of letting the beans “open up” with just a little water before pouring in the rest over the remainder of the 4 minutes.[1]

But here’s the thing: I wanted the first warning to go off at exactly 3 minutes, 30 seconds, so that my screen would change color when I was supposed to start pouring. After all, I’m doing this before my first cup of coffee in the morning; I could use all the help I can get.

With Fin 1, there was no way to do this. The warnings were hard-coded to 10, 5, and 2 minutes.

Right away, I knew I wanted customizable presets and warnings to be the flagship feature of version 2. And so it came to be. 12 presets that include not only the main timer, but the times of each of the 3 warnings as well. Two taps, and you can switch your whole setup to your most-used timers.[2]

I also wanted this version to be a little more helpful for Toastmasters members. The presets will be a big help, of course, for timing speeches of different lengths. But I also added an optional second color scheme for the three warnings. The classic Fin colors are yellow, then orange, then red. The new scheme fits the classic Toastmasters use of green, then yellow, then red.

Another thing that excites me in this new version is the new layout. Thanks to this tip, I finally figured out a better way to handle the custom Courier Pro font alignment issues that were plaguing me for the better part of a year. The new layout is far more smooth and allows for much larger numbers on the main timer. Fin should now be much easier to read from a distance, which comes in handy on big stages.

Finally, I added some delight where I could to the app, to make it respond more to your touches. A little bounce here and there always makes the app feel more fun, and it’s one of my favorite things to do.

I hope you enjoy this 2.0 update to Fin. I’ve been using various progressive versions of it for months now for the podcast, and of course for my coffee brewing and presentation practice. I think it’s more useful than ever.

You can grab your copy here on the App Store as a Universal app for iPad, iPhone, and iPod touch.

Of course, I made a new video too, to show off the new bits. Enjoy.

  1. I never much bothered with timing my brew precisely when I used the Aeropress, but for the Chemex it really seems to make a difference.  ↩

  2. Maybe 12 is overkill, but I can imagine some of my customers needing that many timers.  ↩

x2y Version 3.0

Today, I’m releasing version 3.0 of x2y, my aspect ratio calculator for iOS.

As I’ve said before, I want to continually find ways to improve this app, as it’s something I use regularly myself. When I first started with this next version, I had only intended to add theme support, as a fun way to change up the colors of the interface for those who didn’t necessarily like the default dark appearance. As I worked on the themes, though, I thought of other features that I’ve wanted to add for a long time but just didn’t think I could figure out easily for a minor update. In the end, I decided to tackle a lot more than I orginally planned and make this the major update for 2014.

Thus, the app is now at 3.0. With the original theme support idea in place, plus a few other key features.

There are four different themes from which to choose, and if you experiment a bit throughout the app, you can actually find four more that are hidden by default. I’m usually not a fan of “easter eggs” as I mentioned on episode 42 of Release Notes, but my cohost Charles Perry convinced me that it might be cool to experiment with hiding some themes if they were discoverable enough not to frustrate people. I think anyone who utilizes most of the features of the app regularly will have no trouble finding all four.

Next in 3.0 is iCloud support, which was far easier to implement than I had imagined. Probably because the data being synced in this app is so simple, I was able to get it implemented in a few weeks of my spare time. I know a lot of developers with far more complex apps have had many issues with iCloud, but for simple key value store sync, I found it to be quite manageable. (At least I think. We’ll see if people report major issues.)

Another big feature I added was support for copying your calculated results to the pasteboard. Just tap and hold on the calculated result, and a dialog will pop up, allowing you to choose from a few different formats to copy. One of the formats is CSS width and height, which I’ve been using quite a bit when coding web sites on my iPad in Textastic and Diet Coda. It’s quite handy.

Finally, I reworked the entire Help section of the app, adding the proper mail delegate to my support link, and using table views as opposed to a giant Web view.

All in all, the under-the-hood changes in this version go far beyond what the user sees. But they make me happy, as the app has matured quite a bit from a “first effort by a novice iOS programmer” to something that is much more solidly based on good design patterns. I still have a long way to go as a programmer, but I learned a ton just in the past few months getting this update ready.

I hope the new improvements will be well received. I want to thank my friends who have been coming out to IOSIRL who helped me with some advice on how to implement all of these new features, especially Soroush Khanlou. And, as always, I’ve gotten some great advice from Tim Cochrane at Bombing Brain on certain implementation details.

I hope that if you like the app and you find the new features useful, you’ll consider leaving me a review on the App Store. Positive reviews help me keep improving the app, and they help others to discover the app for themselves.

And of course, no new major version of one of my apps would be complete without a new video, which I’m embedding here. Enjoy.


As more details emerge in this massive scandal over employee non-poaching agreements, I can’t help but think of something I said to my brother a few years ago: If you don’t own a piece of the company you work for, you’re always getting screwed. It doesn’t matter if you’re a senior VP making 30 Million a year. You’re still getting a sucker’s share of the overall take.

What Jobs and Schmidt started here was absolutely atrocious. But it’s not even remotely surprising. Executives serve boards, boards serve shareholders, and shareholders always want maximum profits. That’s the inherent nature of any corporation. And if the goal is to maximize profits, you have to—by definition—minimize cost of goods sold. Which means keeping salaries as low as possible.

Like I said, if you don’t own it…

The funny thing is, though, and I may be extremely naive here, I suspect that for Jobs the motivation for this scheme in the beginning had less to do with keeping salaries low and more to do with a serious case of paranoia about being betrayed. I think when Bill Gates screwed him over so badly with Windows, Jobs became permanently scarred and was always looking for ways to prevent others from screwing him again. He wanted loyalty, and this scheme bought it for him. Later, as the practice spread through the industry, I imagine that keeping down wages became a stronger motivation for most other CEOs.

Again, probably naive of me, and still unforgivable regardless.

If you want to be sure something like this isn’t happening to you, the only choice you have is to run your own company. Otherwise, you are part of a system that is designed to pay you less than you’re worth.

My Adventures in Audiobooks

One of the things I always admired about Steve Jobs was his willingness to call out things that just plain sucked.

And so here I am, saying that syncing content with iTunes just plain sucks.

Today’s example:

There’s a good review of the Jony Ive biography over on Asymco. Since I tend to think Horace is a smart guy, I figured his recommendation was reason enough to go get this book for myself. So I followed his link, on my Mac, to the iBookstore.

But just before clicking “buy” I thought to myself, “Well, I have about ten iBooks I haven’t yet read sitting on my iPad. I probably won’t get around to this for a while.” And so I decided to check and see if there were an audiobook version instead. After all, I spend lots of time walking around the city, trying to get some exercise, and it’s been ages since I listened to an audiobook, so why not?

Why not, indeed.

There on the iTunes page for the iBook, I clicked on the “related” tab and saw that there is indeed an unabridged audio version of the same book for sale, on iTunes, no less. Narrated by Simon Vance, even. Perfect. So I bought it.

And at that very moment, I screwed my chances of listening to this book on my iPhone.

You see, unlike most forms of content on iTunes, audiobooks don’t sync over iTunes Match. They also can’t be downloaded more than once. I learned this the hard way, when I turned on my iPhone and fired up the Music app, expecting to see my new audiobook downloading automatically. It wasn’t. I also couldn’t find an audiobooks tab anywhere, even in the “more” section of the Music app. Hmmm. Did they move Audiobooks to another separate app?

I search the App Store. Hundreds of audiobooks apps; none of them from Apple, none that can read files bought on iTunes. I search the Internets. Confirmed. Audiobooks are still in the Music app, though some people are having issues since the iOS 7 update. Not a good sign.

So how to get the book over there?

I know, I’ll put it into a playlist, and that playlist will sync over iTunes Match, right? Nope. Playlists with audiobook files don’t show up in iTunes Match.

Okay, I’ll open up iTunes on my iPhone, search for the audiobook, and just download it again directly on the device, right? Nope. If I want to download it again, I need to purchase it again.

Okay, fine, I’ll bite the bullet and do something I never wanted to to again—I’ll plug my iPhone into my Mac and sync the audiobook using iTunes like a barbarian. First I try to simply drag the book over to the right side of the window to manually sync it. No dice. It gives me a blue highlight, as if to say, “go ahead and drop the file here.” But then nothing happens.

Then I go to the books tab and set it to sync just audiobooks, and I get a warning telling me that since I’m using iTunes in the Cloud on this phone, syncing this one audiobook file manually will force me to erase the entire contents of my music library on the phone first. Am I sure I want to do that?

No, iTunes. I’m not sure I want to erase 50GB of music off my phone to get one audiobook.

Not one to give up so easily, I drop the audiobook file into my Dropbox, hoping I can open the Dropbox app on my iPhone, and use “open in…” to send it over to Music. Nope. (Sidenote: Downcast gallantly attempted to open the file, but couldn’t get past Apple’s DRM. “A” for effort on that one.)

And so here I am, with a 9-hour audiobook on the least-likely device I’ll ever want to use to listen to it: My 27-inch iMac.

Thanks, Eddy Cue. Bang up job you did there.

As an absolute hail Mary play, I decide to plug my iPhone back in one more time and try the manual drag and drop of the file in iTunes. This time, it starts a sync without any warnings, and I get a progress bar at the top. So far so good. My cursor beach balls for about two minutes, but it doesn’t crash. The progress bar switches over to “Finishing Update” and I’m filled with hope. And then it keeps saying “Finishing Update” for another fifteen minutes. Convinced it must still be working on it, I wait. And Wait. If I turn on the iPhone, I can see the Audiobooks tab now in music, and the Jony Ive book appears to be there. But I can’t play it. And iTunes is still “finishing.” So I wait some more.

Forever Finishing

Finally, I get impatient and try to cancel the sync. Won’t cancel. I tap the eject button in iTunes, and I get a warning telling me that the sync is still in progress. Do I want to eject anyway? No. Another five minutes.

Okay, this time, I just want to eject it. So I say yes, I do want to eject anyway. Still “finishing” but I get an additional window, no close boxes or cancel buttons, called “Syncing iPhone.” with its own independent progress bar that never shows any progress. I guess this is iTunes’ way of scaring me into not unplugging.

The Second No Progress Bar

Another ten minutes. Remember, this is all for one audiobook. I realize the file is 250MB, but over a USB cable, what should that take? Maybe two, three minutes, tops?

Finally, I get bored and yank the Lightning cable. We’re already way past the point where any sane human being would have given up, aren’t we?

Look, if it’s all or nothing with iTunes in the Cloud, then everything you sell on iTunes has to work over the cloud. Everything. Not most things. Otherwise, if audiobooks are special and can’t be synced over iTunes in the Cloud, give me some other way to sync them without wiping out my whole library. Is that too much to ask?

And if manual sync is supposed to be the way to do that, then make sure manual sync actually works. Because it sure doesn’t seem to work as far as I can tell.

Also, let’s keep in mind that I’m more than a little savvy with this technology stuff. And so are a lot of my Twitter followers. And none of us could figure this out. If this is possible, and I’m missing it somehow, you get an F minus for usability, Eddy. There’s no way a “normal” person would have tried this many different things.

Seems pretty obvious to me, since you still sell audiobooks on the iTunes Store, that there should be an easy way to listen to books bought on your Mac on any of your iOS devices. I’m not talking about some obscure old content I bought ten years ago. I’m talking about a file I bought today, for crying out loud.

Still, third time’s a charm, right? And I want to be thorough for the sake of this post. So I give it another go. I plug in my iPhone and try the manual drag and drop in iTunes for the third time. I’m about to eat dinner, anyway, so how can it hurt? First three times I drag, it gets stuck in “preparing” to update and I have to cancel. So I quit iTunes and relaunch, drag it a fourth time, and just walk away.

Thirty minutes later when I return from dinner, the progress bar is gone. iTunes is sitting idle. I fire up the Music app on my iPhone, and sure enough, the file is sitting there. Tap it, and it starts playing. More than three hours after I purchased the thing, I can now finally listen to the Jony Ive audiobook on my device of choice.

Isn’t this the sort of thing for which we usually make fun of other companies?

My advice: Don’t ever buy an audiobook from iTunes. Or, if you do, buy it on the device where you want to listen to it, because you won’t be able to move it after the fact without wanting to punch someone.

And this is but one small example of how crappy it is trying to sync content to an iPhone from iTunes. This is no isolated incident. I don’t have the heart to tell you the one where I tried to turn off iTunes in the Cloud and go back to manual syncing all my music last year. That’s a whole day I’ll never get back.

Fix this stuff, Apple. Seriously. iTunes is a multi-billion dollar business. You should be embarrassed of how piss poor this experience is.

Apple takes the lofty route for iPad « Observatory

Apple takes the lofty route for iPad « Observatory: “But — while this spot can be seen as uplifting and inspirational, it can also be seen as incredibly pretentious. One must admit, it’s a bit of intellectual overkill for those who just want to do their email, surf and shop — which probably covers most of the tablet-buying public.”

(Via Ken Segall.)

That, in a nutshell, is exactly Apple’s problem with the iPad. People think it’s an email, surf, and shop machine. If it continues to be just that, the iPad is never going to meet Apple’s expectations. Thus, the “loftier” ad approach of the Verses series.

People raved about the Misunderstood iPhone commercial over Christmas, but I actually think these spots are much more important to Apple’s long-term future. Thanks to Apple’s misguided driving of the App Store into Crazy Eddie’s Discount Bonanza, people are losing sight of just how powerful a tablet can be. They clamor for a “bigger” iPhone, because they figure that would do just about everything they do on their iPads well enough to no longer need an iPad. And that’s certainly not good for Apple.

Sure, the message is lofty, and maybe it only appeals to Apple’s current customers. But those customers aren’t getting as much out of their iPads as they deserve. Sometimes you need to start with a lofty message to reaffirm your core values. Sometimes you have to remind people that you’re trying to improve people’s lives.

If Apple wants to continue selling iPads, it needs to carve out a space where the iPad is seen as essential to the things we want to create, not just a luxury toy for watching movies on a plane.