How the App Store Ended a Golden Era of Software

As an app reviewer in the early 2000s, I had a front-row seat to free apps’ evolution from delightful to predatory

Credit: picture alliance/Getty Images

In the few weeks since I updated my iPhone to iOS 13, I’ve been getting pop-up notifications when an app has been tracking me. It’s a new location transparency feature from Apple, and it’s a good reminder of how many of those location-tracking apps you don’t use anymore, maybe never used, and can’t even remember why you downloaded in the first place.

I’ve been getting a lot of those alerts because I have an obscene number of apps on my phone. I have dozens of folders full of apps. You know those dots at the bottom of your iPhone screen that show you how many pages you have to swipe through? I have 16 of those dots. I am officially an app hoarder who’s embarrassed to show people my iPhone. This is me, raising my hand in the AA meeting, but I’m not anonymous and the other “A” stands for apps.

I started reviewing apps nearly two decades ago, long before Apple’s App Store or the iPhone even existed. Back then, we called them applications, or software, or sometimes just downloads. It’s hard not to drown in nostalgia over those good old internet days, when a free app almost never meant that you were the product. The industry was dominated by a few big players and a lot of software cost well over $100. But there were also independent developers making all kinds of amazing games and utilities. If an application was free, it usually meant that someone had spent their spare time making something cool, just for the hell of it. You downloaded these apps directly from their creators’ websites. And maybe if you liked what they made and you found it useful, you could click that donate button or put some money in the “tip jar” on the same website and then everyone would be happy.

I wasn’t quite sure if my memory of this golden age of shareware was accurate, so I reached out to my friend James Thomson, indie iOS and Mac developer, former Apple employee, and creator of the beloved calculator app PCalc. Thomson has been developing software since before most of us had even heard of the web. He used the comp.sys.mac.apps group on Usenet and the InfoMac FTP archive as a way of getting the word out about his apps. Thomson’s first version of PCalc came out in 1992, and he distributed it as postcardware. “If you liked it and used it, I asked people to send me a postcard,” Thomson told me.

A few years later, Thomson developed DragThing, which Apple geeks will remember as the best app launcher on the Mac for at least a decade, but which only officially died this year. (RIP DragThing.) For those of you who were not born before Mac OS X, that dock that lets you easily launch applications didn’t always exist, and Thomson created DragThing pre-dock to let you open anything with a single click. Thomson says, “The first version of DragThing was ‘coolware’ — if you liked it and used it, I asked people to send me something cool. I got a lot of weird and interesting things from around the world.” Thomson’s experience with getting paid for shareware didn’t even start until 1996. That’s when he got an email from a large advertising company that wanted to use DragThing, which he was still distributing as “coolware.” The only problem was that the advertising company’s accounting department didn’t understand “cool.” They asked if they could send Thomson money instead, and he accepted.

Of course, in those halcyon days before Apple’s App Store, it was also much easier to download a fake app that could take down your computer with a nasty virus, which is one reason why reviewing apps really meant something at that time. Anyone reviewing software back then was some kind of spyware-killing superhero making the world safe for free software.

But that was a long time ago.

When I look back at all the apps I told people they should download over the years, I’m struck by how many are no longer updated or simply don’t exist anymore.

Apple released the first iPhone in June 2007, a little over a year before they opened the iPhone App Store in July 2008. In that sad and lonely year, people spent a lot of time swiping, pinching, and zooming through their camera photos and maybe making a phone call or two, but there wasn’t much else you could do with the device. It would be a full year before iPhone owners could even cut and paste. But then the App Store changed everything. Apple would like you to believe that it changed everything for good, but I’m not so sure that’s true.

In 2015, I started reviewing iPhone apps on several different podcasts that I hosted for my day job. That was when the app hoarding began. Don’t get me wrong. It was fun to try new apps with abandon, especially when I expensed the cost to my employer. Back then, most paid apps cost only 99 cents, but I came up in the age of free software, so it took me a while to get used to paying for anything. And sometimes trying new apps on your own dime (or 10 dimes) felt like death from a thousand 99-cent cuts. Here’s where my memory of this time differs from Thomson’s. Before the App Store, he charged $29.99 for DragThing and $19.99 for PCalc and almost no one balked at the price. “Now people complain about anything that isn’t free and the $9.99 for PCalc is somehow seen as premium pricing,” he says.

It wasn’t that I didn’t understand that developers deserve to be paid for their work, it’s just that my experience of indie software was that you could try before you buy, with the shareware or donationware model. But neither the iPhone nor the Mac App Store has ever had a seamless way to offer demo software. There are limited free versions that allow you to upgrade if you like it or get rid of the ads if you want to pay, but it’s not quite the same as the way trial software used to work.

Worse, the more operating systems (and especially iOS) became these kinds of Alcatraz-like locked-down systems, the more you needed separate apps to do many basic things — things like messing with the Windows Registry, defragging, or entering commands in the command line.

Despite all that, I still loved reviewing apps, especially those created by independent developers. It didn’t matter that Apple Maps was lackluster at first, because there were independent alternatives. Why would you use the built-in weather app when there was DarkSky, a much more accurate (and cool-looking) tool that was created by two smart dudes who funded their project on Kickstarter? There was always the potential to be the first to discover the next Twitter, the next Foursquare, the next Monument Valley.

As a user of apps, I rarely saw what the transition from downloads to app stores was like for developers. “It was painful to give up the direct relationship with customers, or at least with the customers who preferred to buy our products only via the App Store and who never communicate with us directly,” says Jean MacDonald, former partner at Smile Software (maker of TextExpander) and co-founder of App Camp for Girls.

If you ask developers whether the App Store has been good for their business, they’re rarely as exuberant as the promotional videos at Apple’s annual developers conference. Still, there’s a lot to be grateful for. Thomson points out that he now has access to a global marketplace where he doesn’t have to deal with any of the local laws and taxation. Apple handles all the server infrastructure for selling and downloading and he no longer needs to check serial numbers or thwart pirates. “I just put my software up, and — hopefully — get paid every month,” he says.

But that ease of use also means the barrier to entry is lower, and maybe it’s a little bit too easy to create an app. Of all the gems I was lucky to find and review and recommend during my career as an app reviewer, there was also a lot of garbage. And I’m not just talking about the garbage I had to weed through to find the gems. I’m also talking about the apps I reviewed and recommended. Many of those turned out to be garbage, too.

When I look back at all the apps I told people they should download over the years, I’m struck by how many are no longer updated or simply don’t exist anymore. And of those that still do exist, many of them perhaps should not. I (almost) always checked the privacy policy of every app I reviewed, and I tried my best to determine if the company was selling our info or tracking us when it didn’t need to. But there was no way for me to know if the developers were going to sell their app to a less privacy-minded company or just change their privacy policy later in order to monetize the app themselves. Suddenly those 99-cent charges seemed like a bargain compared to handing over all of our personal and location data so it could be auctioned off to the highest bidder.

And even if I did decide that the privacy trade-offs of using a certain app were worth it to me, I now see that I accepted many of those trade-offs from a place of privilege. Privacy means something drastically different for people of color or people living in some other countries or women who’ve been in abusive relationships or other marginalized groups whose situations I can’t begin to understand.

Just as I began to reconsider the whimsy with which I downloaded and recommended apps to anyone who would listen, the tech backlash happened.

For me, the reckoning began with Manoush Zomorodi suggesting that apps were keeping us from being bored and preventing us from being brilliant. Then Tristan Harris, former app designer himself, forced me to consider not only that I wasn’t spending my time well, but that some of these apps might actually be inhumane. Snapchat had racist filters. was giving teens eating disorders. YouTube Kids was full of ads or porn or something worse. Then came Uber’s no-good-very-bad year and then Facebook’s and then somewhere along the way these apps on our phones became decidedly uncoolware.

In retrospect, it’s easy for me to see that when I recommended the Uber app to everyone I knew back in 2015, I wasn’t considering the lives of cab drivers, or at the very least I thought Uber was a better option for them. I’d never heard of the medallion system or how Uber ran roughshod over it. I don’t recommend apps to people very often anymore. Part of this is easy because it’s no longer my job to review them. But it’s still my job (and maybe everyone’s) to think about what we download and recommend to others.

In an extended interview on Krista Tippett’s podcast On Being, blogger Anil Dash asks of us, “At the time when somebody says, ‘You’ve got to try this new app,’ ‘You’ve got to use this new tool,’ think through: What are the implications of, one, me using this, but two, what if everybody does?’”

It’s exhausting to imagine giving this much thought to every app we download, and I hope that developers are doing at least some of this thinking for us. MacDonald, a Mac software veteran, now works for, a service (and an app) designed as an alternative to the toxicity on Twitter. “Each time there’s a new outrageous example of a social media company’s malfeasance or incompetence, we get a wave of new folks who want to try something else.”

But must all designers consider the long-term or unknown effects of the software they create? Thomson says yes. “All apps can potentially have a negative impact. I make a calculator, which seems like a harmless tool of pure mathematics. And yet, I know people working in the U.S. nuclear weapons program have bought copies. I’ve heard of people using PCalc to calculate things in life-or-death medical situations. Those things certainly don’t help me sleep at night.”

Head of Platform Stories, Technology @Medium. 👩🏽‍💻

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