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Messaging Timeline

The history of messaging, and where it’s going

Messaging Timeline
There are in my view four main phases in the history of online and mobile messaging.

The first phase included e-mail and to some extent real-time messaging (in the form of chat rooms), but was strictly within walled gardens. You could only communicate with others using the same proprietary service provider (America Online, Compuserve, Delphi, etc.).

The second phase was the beginning of interconnected systems and the Internet. E-mail no longer stayed on a single server, but could go between companies. Real-time messaging, switched from chats that people had to join, to curated lists of friends, the buddy list, which dictated who you could chat with and allowed people to know when you were available for chat. To chat with someone you needed to know their username (or be able to find it in a directory). In some implementations, such as MSN Messenger, the other user had to approve you being able to see if they were online, but in others like AIM, you could see who was online as long as you knew their username (assuming they had not blocked you).

The third phase was the emergence of text messaging on cell phones. This includes SMS, which spread initially in Europe before becoming popular in the US. Initially text messages were limited to other people on the same carrier, not that different than e-mails on the early online services. As SMS started working across networks it spread very quickly, becoming used more than voice calling for certain populations, certainly among teenagers at the time. One could argue that phases two and three were largely concurrent. ICQ launched in 1996, roughly the same time as SMS made it onto cell phones.

In the fourth phase, which we’re now in, e-mail and real-time messaging have to some extent merged. Facebook Messenger perhaps is the best example of this, where there is no real differentiation of real-time message and e-mail. If you don’t see the message now, you’ll see it later. In addition, messaging applications are removing the need to curate your contact list, and making all your contacts who use their software available for you to message. Whatsapp does this really well, and Facebook Messenger now also does this in some fashion. There is no need to know any kind of special username for these systems, knowing some other associated contact detail such as the person’s phone number or e-mail address is enough. On one hand, this presumes somewhat more familiarity with the person, on the other hand you can’t have a messaging account that uses a made up username that is only used for that purpose. A little noticed aspect is that these new messaging systems are moving back into a walled garden approach.

A bit of history, to give perspective on the current state of messaging. Caveat: Don’t think of this as a comprehensive history, it’s filtered through my memory and perspective.

Proprietary Online Services

1983 CompuServe Ad (from Apple ][ history)
A long time ago, maybe 30 years ago, a child logged into an amazing service called Compuserve. Sure, it cost something like $20/hour to use and  he was thus limited in how long he could enter that world, but he was immediately amazed that he could communicate almost instantly with users across the globe. Other services came and went – GEnie, Delphi, America Online, Prodigy, and the whole BBS world.

While there was e-mail and real-time messaging on these services, they were for the most part self-contained – if you were on Compuserve you couldn’t message someone on Delphi. In the BBS world, some interaction between sites emerged in the form of FidoNet (and the lesser known WWIVnet). While these services and bulletin boards served millions of users at their peak, they were quickly replaced by Internet service providers who had no need to create the content and manage forums like the legacy services. The new generation of Internet providers had another distinct advantage over the legacy companies – they were all connected through standard protocols. E-mail from any Internet provider could reach anyone on any other Internet provider.

Most of those services are now obscure footnotes in the history of tech, at least in their original forms (AOL obviously exists, but primarily as a content company. Compuserve is now a value brand of AOL (ironic considering how expensive Compuserve was originally), and Delphi exists as an online forum), but out of them sprang incredible innovation. GEnie had massively multiplayer games before most of the people playing them today were born. Compuserve invented the GIF format which was an important format in the early days of the web, then mostly disappeared for years due to patent licensing issues, before being revived recently to post annoying animations on social networks. Out of AOL (and Mirabilis, the Israeli company acquired by AOL that created ICQ) came what today we call Instant Messaging (buddy list based real-time communications).

Just a note on GIFs and the early days of online services. People who never used the early online services, or never used an early dial up modem (Compare 1200bps modem used in the early 1980s to a cable modem today running with a 12Mbps connection – that’s 12,000,000bps, or 10,000x the speed), don’t quite understand what it was like. Imagine waiting for each line of text to show up in sequence on the screen. GIFs would similarly render line by line, and you’d have to wait minutes just to see the simplest of images. I wish I could find an appropriate video to show what it was like, but needless to say it was a wholly different experience from what we have today.

One good thing that was mostly lost with the demise of these earlier online services was a sense of community. The forums run on these services engendered very loyal communities that generated wide ranging discussions on almost any topic. Perhaps thats why one of those services, Delphi, emerged as a web-based community site, with over 25 million discussions comprising over 300 million posts. People realized the true value of the service was the community. That’s another reason that early online communities like the The Well had (and perhaps still have) immense influence.

The Internet

My first e-mail account outside of one of these services and directly connected to the Internet was around 1990-91. I was working at Kurzweil Applied Intelligence and they had the domain (this being before the web was a marketing tool). I don’t remember my specific e-mail address. As it was 1990-91, there was no web to speak of really (Mosaic would not be released until 1993), and Gopher was just about the come into existence. The e-mail account was primarily for intra-company communications, although it was also used to communicate with other companies and institutions. Around this time I remember someone sending the first advertisement I had seen via e-mail. I wouldn’t call it spam because I think it was sent by someone at the company, but it led me to Eastgate Systems, a publisher of Hypertext fiction (and software), where I made by first e-commerce purchase (consider that this was before there was a commercial web).

Within a couple of years, every adult below a certain age had e-mail. Instant messaging was just starting to emerge. All university students received e-mail addresses (although as I recall my assigned e-mail address was actually based on my year of graduation AND the physical mailbox number I had in the school post office – luckily I also had one I could choose through the computer science department). Other people started getting e-mail addresses when their legacy online services connected to the Internet, and as they signed up for the new independent Internet service providers (who used standards based dial-up software, and generally provided no content). The first commercial ISP in the US (and they claim to be first in the whole world) was a service called, appropriately, The World, which was run by a company called Software Tool & Die in my hometown of Brookline, MA. That serviced launched in 1989.

In university I also remember a campus-wide messaging program that ran over AppleTalk. I don’t remember what it was called, but I remember each quad had its own network, and students used to chat up other students they didn’t know just because they were online (if you remember the name, please share it in the comments). Unlike the instant messaging applications that came later, this campus system had no buddy list, it just showed you who was connected at the time, separated by quad. That was about 20 years ago.

Late 1990s ICQ Client

Jump ahead a few years, and instant messaging was huge. There was ICQ, AIM, MSN Messenger (discontinued and replaced with messaging within Skype), Yahoo, etc. The breakthrough of ICQ, launched in 1996, was that it was not tied to a paid service. The writing was on the wall – a year later AOL separated their instant messaging service from their paid online service and launched AIM. The following year AOL bought ICQ. Yahoo Messenger, MSN Messenger and others followed as well. AOL did a study in 2004 that showed that 70% of teenagers used instant messaging (like their own AIM) to communicate.

The separation from paid services hit e-mail at the same time, with the launch of Hotmail the same year as ICQ. Some would say that it was Hotmail being web-based that was significant, or that it was free, but really, as mentioned, it was the fact that it separated you from your paid carrier that was most significant. It created the possibility of having a permanent e-mail address for life. No wonder Microsoft snapped up Hotmail in 1997, and that Yahoo launched their own web-based e-mail product the same year. Web-based e-mail was about customer lock-in more than anything else. Integration between e-mail and instant messaging at this stage was basically non-existent. At most, you might have received notification of e-mails in your instant messaging application.

Google was just getting started at this time, and their initial product was obviously their search engine. They wouldn’t launch their e-mail product (Gmail) until 2004, and their first instant messaging product (Google Talk) until 2005. Google would launch their instant messaging product with two key features: One, that it was based on a standard protocol (XMPP) outside of their control (although not their influence). Two, that it could be used within their web-based e-mail product, Gmail, without needing a separate client. AOL had offered AIM Express, a web client, since 2004, however it just launched a window with a traditional AIM UI.

SMS and the Rise of Cell Phones

While it’s hard to imagine it today, you only have to go back to the mid-1990s when cell phones were only capable of voice communications. Short Messaging Service (SMS), the first standard for sending text messages from cell phone to cell phone, wasn’t available until 1993, and then only in a limited fashion. Most phones that supported SMS in the early days could receive, but not send messages. It was not until 1999 that text messages would be able to be sent between different networks, causing their usage to skyrocket. Eventually, as unlimited texting plans began to be offered by carriers, the usage of SMS would grow even more.

The availability of SMS grew with the availability and affordability of cell phones. For teenagers, who were beginning to get cell phone and were used to instant messaging on the computer, SMS allowed similar instant communications, but on the go. Text messaging grew among teenagers for several reasons. First, they were used to messaging using text. Second, texting in the early days was a bit of a pain without a full keyboard, so they had the patience to do it. Third, such short messages relied on shorthand which they were much more willing to rely upon. Clearly the features of SMS did not compare to that of instant messaging client on the computer, nor was it free at the beginning, so both were used concurrently for a long time until mobile Internet became a standard feature on cell phones, and messaging converged.

The Convergence

Recently, the trends have changed quite a bit. The rise of Facebook, and its messaging platform, seems to have hurt existing instant messaging platforms. There have always been clients (like Trillian and Adium) that could support multiple protocols (having AIM, ICQ, Yahoo, MSN and Google all running in the same window), but the reality is that once everyone you chat with is on one network, there’s no need to jump through those hoops anymore. Multi-network clients have never been able to fully take advantage of all the features of all networks, so if 90% of your contacts are on one network, chances are you’re just going to use their client. I used to have friends on AIM (mostly in the US), friends on MSN (mostly in Europe), a few friends on ICQ (mostly from Israel), and a few friends on Google. I didn’t really care since they all ran through Adium on my computer. Something happened, however, which slowly started changing how I connected to people.

First, AIM collapsed. There are a few reasons for this, and they’re probably a bit different in the details for different people. For me, my AIM screen name came from my original 1980s-era AOL account, which both of my parents had had accounts on, but who only my mother was still using. When my mother’s AOL account got overwhelmed by spam, she finally gave up on it and cancelled the account. Without the account it was linked to, my screen name which I had been using for decades (even before it was usable on AIM) went away. I already had a second AIM screen name, which I actually had set up to use Apple’s iChat video chat with a few friends, but eventually that screen name also failed, which had something to do with needing a security question added (I guess AOL was looking to improve their security). Since I used a third-party client, it took me forever to figure out what was wrong. The truth is, I didn’t really care, as I hardly used it. If I had not had alternatives to AIM, I probably would have worked harder to get it working again, but I did have alternatives, and thus did not. I’m sure others have had similar experiences in shedding their AIM account usage. With no base of users like it had when AOL was a major service provider, AIM usage dwindled to next to nothing. The messaging services that were connected to content and e-mail sites that people used every day did better, and thus MSN (until it was subsumed by Skype), Yahoo and Google took some of this market share. AOL sold off its ICQ division to a Russian company, where it maintains some marketshare in the Russian and East European market.

Second, the previously mentioned Facebook messaging. It took time for Facebook to get their messaging product up to spec, but for those with large Facebook networks, Facebook quickly overtook the size of most people’s buddy lists on other networks. People were on Facebook anyways, and the friends list started popping up conveniently on the right side of the page. In addition, Facebook did something brilliant, they merged instant messaging with longer e-mail-like messages, and kept an ongoing record of all communications between friends. Send a message and your friend just disconnected? No problem, they’ll see it when they’re back online. As Facebook went mobile, and people started checking Facebook messages on their phones, it finally became a very effective messaging solution, replacing the need to e-mail or IM your friends.

Third, the emergence of mobile-first messaging apps. It’s no secret that Facebook struggled quite a bit with their early mobile apps. They were slow and clunky. Their messaging offering also did not coalesce at first. Originally they handled messaging in their main Facebook app, and later separated into a separate app. One of the reasons they needed to separate it out, was to compete with the apps that started in mobile, when Facebook was still working on the web. The biggest mobile-first messaging app today is WhatsApp, which recently announced it has 430 million active users, and handles 50 billion messages a day. That itself is more than the number of SMS messages sent every day worldwide, at least according to the numbers I’ve been able to find. The real trick of the mobile-first messaging apps was quite simple – they confirmed the phone number as belonging to the user (by sending a code via SMS to their phone), then checked the user’s address book on their phone to see who else was in their system. No need to curate a buddy list, look for users in a directory, etc. Just confirm your own phone, and everyone whose contact information you already had was automatically reachable.

In addition to WhatsApp, some other companies include Viber (a voice-focused company which claims 340 million users, which also supports text messaging and audio and video chat), and a series of Asian companies such as WeChat (China), KakaoTalk (South Korea) and LINE (Japan). The Asian companies take a very different approach, creating a full platform for commerce, gaming, and more around their messaging apps. Not all of this functionality is available to users in Western countries, but in their native languages and products, the applications are much more than messaging apps. WeChat, KakaoTalk and LINE are all pushing out from their home base countries and picking up user bases across the globe.

All of these changes have created a situation today where companies that have only existed for a few years have built up more active users than existing messaging services ever had in their heyday. Facebook has more than 800 million users who access their site via mobile (although not necessarily for messaging, it’s a good assumption that many of them do). There are many fast-growing messaging apps that have hundreds of millions of users, and are still growing incredibly fast.

In addition to these ‘standard’ messaging apps, there are a few other categories of messaging services that are worth taking a look at:

Cell Phone Manufacturer Messaging

Another category of mobile-first messaging apps are the cell phone manufacturer apps. This was started with Blackberry Messenger (BBM) in 2006, which allowed Blackberry users to send instant messages between themselves. This service ran over the Blackberry’s Internet connection, and circumvented the carrier’s SMS services. Used as a differentiator, BBM was incredibly popular among Blackberry users, and perhaps could have been leveraged into a major player in the messaging space beyond Blackberry, but was kept Blackberry-only until long after the Blackberry had lost most of its users. Consider for a moment that BBM launched 3 years before any of the other mobile-first messaging platforms like Whatsapp. Imagine if they had launched it on other platforms back then, or at least around the same time as Whatsapp. Undoubtedly they were afraid that BBM on other platforms might make it easier for their customers to leave and get other phones, but in the end, they did that anyways.

Apple followed only in 2011, with its iMessage messaging platform. When your iPhone detects that the person you are messaging has an iPhone also, the message is sent over the Internet as an iMessage. If the other person does not have an iPhone, then it sends it as a standard SMS. Apple followed the launch on the iPhone with a client on the Mac as well, allowing users to see their iMessages on their computer as they work (and to respond).

Group Messaging

While many messaging apps offer a way to create group chats, a new generation of group chat applications, focused on business and some niche markets has started to appear as well. These apps are in general not geared toward the teenage user, but rather people who work, to take advantage of the power of mobile messaging, but with a focus on productivity, not stickers and games.

One recent app, which just launched a few months ago is Zula. Founded in Israel by VoIP pioneers Jeff Pulver and Jacob Ner-David, Zula offers a similar experience to the standard messaging apps, although with a few business-oriented features that make a big difference. For example, when adding someone to a chat you can look at your cell phone’s phone book like in other apps, but you can also connect to Facebook, Google, and LinkedIn and see all your contacts on those services as well. You can also share documents. For an application that comes from people with a background in VoIP (Pulver founded Vonage and Ner-David founded Delta Three) it is perhaps not surprising that one of its innovative features is the ability to press a button and bring everyone in your chat into a conference call. Certainly text chat is very convenient, but when you need to resolve an issue quickly, being able to talk to everyone involved, whether they’re in the next room or across the globe, is a very useful feature.

Another somewhat similar group messaging app was called Anchor, from a company called Tomfoolery. Tomfoolery had been founded by former Yahoo employees, and was bought by Yahoo just last week. The product and company have been shut down by Yahoo (who gave users a week to get their media off the site) who will presumably come up with some similar offering in the future. However, considering it was shut down so fast, it might not be a product they’re looking to launch, and what comes out in the future might be very different.

Other group messaging applications go after specific niches, like education. A number of applications have sprung up to allow teachers to communicate with students, with parents, or with both. In general these applications take on more of a broadcast method, whether a teacher sends out information, but doesn’t always allow responses. In 2011, Remind101 was launched to provide a communications platform for teachers, students and parents. Just this week, Remind101 raised a $15M Series B round led by Kleiner Perkins Caulfield & Byers. Last year, Scholastic, the massive educational publisher, launched Class Messenger with similar functionality. These applications allow teachers to pre-load an entire class, and communicate with all students, or all parents, or individuals as well. As a parent of a first grader, I certainly would love to be able to find out easily what my child’s assigned homework was each day, and be able to communicate with teachers directly (although these application do not necessarily allow parents to respond).

One interesting application which is not strictly a messaging app, which is actually in use in my child’s school, is Ringya. Ringya lets you pre-load a contact list, just like a teacher can add all the parents to a contact list at once, but it’s not specific to school. In my case, I have an entire school directory in Ringya, which gives me contact information for every parent in the school. If they’ve installed Ringya on their phone, I can contact them through the app. If not, I can still initiate a text message or phone call using the phone number in the directory. Teachers can contact all the parents in the class, or all the parents in the school at once.

Mobile-First Messaging, in a bit more detail

Before I finish up, I just want to take a further look at the segment of the messaging market that is seeing the most growth right now, the mobile-first apps. As mentioned, the biggest apps right now are WhatsApp, Facebook Messenger, Viber, WeChat, LINE, and KakaoTalk. Let’s start by taking a look at what platforms these apps currently support:

Mobile Messaging Platform Support

Yes, I’ve left out some platforms these apps support. Most notably Nokia S40, Symbian, and Samsung’s Bada. There’s only so much room, and I’ve added the platforms I felt were the most important. It’s important now that these platforms are supported for lower-end phones, but it’s my belief that in the future Android will swallow up the low-end market, and since Nokia is now part of Microsoft (or will be soon) I don’t expect much of a fight to keep S40 competitive.

A few things. WhatsApp is the only one that is mobile-only. They have remained very focused on what they do, and they’ve clearly done it well. They also support lots of low-end platforms not shown.

Facebook Messenger is kind of in its own category. It has very different goals than the others, although we might see these goals converge in the future. It is the only app that is a feature of a bigger site, and that makes it a bit different than the other companies. In theory it’s not even mobile-first like the others, but considering it has over 800 million mobile users, I’m including it.

Most of these apps are heading to the desktop. Viber already supports all major desktop platforms, probably due to its focus on audio and video chat, which is very convenient when one is at their desk. LINE, KakaoTalk and Facebook are all adding desktop applications.

Now let’s take a look at the features supported by these apps:

Mobile Messaging Features

What stands out to me about the above chart is that all the apps are converging on the same feature set. Facebook is as mentioned above a bit in its own category since some of the community features that other apps are trying to build in, are part of the larger Facebook site and not supported in their messenger app. WhatsApp has the least features of the other apps, keeping with its strategy of keeping things very simple (some would argue too simple). I suspect other than Facebook and Whatsapp, we’ll be seeing all the others fill in any missing features on the above chart in the near future.

One thing I haven’t really discussed at all is how these apps make money. WhatsApp at one point charged for their app, and now give it away for free, but charge an annual $0.99/year subscription for new users past the first year. Some charge for Sticker packs and themes. Viber offers calls to regular telephones. For a great summary, the following is a chart created by Mark Watts-Jones created for his Mobile, Messaging and Marketing blog:

Messaging Monetization
10 ways that free messaging apps monetize (Mobile, Messaging and Marketing)

For full details on what these ten monetization strategies include, see the full article 10 ways that free messaging apps monetize. Worth noting is that WhatApp is unique in charging money for the actual app, and it is the only revenue the company has pursued until now. Only one, Nimbuzz, uses advertising. Every app except for WhatsApp sells stickers. WeChat, LINE and KakaoTalk, the three Asian apps I include in my own chart, are the three on this chart which pursue the most different monetization strategies. These include things that none of the other apps are doing, such as sponsored stickers, official accounts and other content like themes. In some ways, these can be traced to cultural acceptance of these types of monetization in China, Japan and Korea.

If you made it this far and actually read everything above, I’m impressed. Make sure to add your comments below on what you remember from the early days of Internet and mobile messaging, what your favorite messaging apps have been over time, and what you think about messaging today.


UX Note: Apple needs to get in sync

Apple IIe (Wikimedia Commons)
Apple IIe (Wikimedia Commons)

The first computer I used was an Apple II in a computer lab in my elementary school. My first computer was an Apple IIe. I am forever thankful to my father who convinced me that replacing it with a Mac SE was the smarter move than getting the Apple IIgs. Except for a few companies that had me working on Windows machines, and some development on Linux boxes, I’ve been using Macs ever since. I’ve been on the iPhone since the first one in 2007. I love Apple and most of their products (the Mac Portable should never have come out, and the Pippin…let’s not go there).

I love that their products ‘just work’ and are consistent in design (due to their ‘Human Interface Guidelines‘). That’s why it pains me when they don’t work. Some things should work better, and just don’t (and don’t get fixed). In particular, I’ve found that Apple has a problem keeping things in sync with their iTunes/iCloud services.

Let me just preface this with saying technically there are no iTunes accounts and iCloud accounts, there are really just Apple IDs that are associated with iTunes or iCloud. I understand this, but we use these IDs in general for two reasons, for iTunes and iCloud. For that reason I call them iTunes accounts and iCloud accounts.

Here are a few examples of these problems:

De-Authorizing Computers

You probably know you can link up to five computers to a single iTunes account. In a small family these can get used up fairly quickly. Especially with tech-heavy families, where one or more parents might work in high-tech and have 2-3 computers they’re using themselves. More importantly, you need to de-authorize computers you no longer are using. If you still have the computer you no longer want to use, you can de-authorize the computer from within iTunes on that computer. What happens if you don’t have that computer? Like if the computer died and you replaced it? Certainly there must be a way to de-authorize a computer you no longer have, right? Well no, not directly. The only way to de-authorize a computer you no longer have is to de-authorize ALL your computers at once. There’s also a catch. You can only de-authorize all your computers once a year.

Doesn’t it make sense that you’d be able to see all your computer that are authorized on your iTunes account and could de-authorize specific ones whenever you want? Apparently not, according to Apple.

Using iTunes and iCloud on the Same Account

If you are a single person and pay for your own service, then this probably never occurred to you. Most people when they set up iCloud set it up with their existing iTunes account. Makes sense. That is, it makes sense as long as you have complete trust in everyone with whom you’re sharing. For example, let’s say you want to share your iTunes account with your children. Great. Save some money. However, it also means your children can now log in on, read your e-mails, check your calendar, read your notes, check out your Pages, Numbers and Keynote documents, locate your devices on a map, etc.

The solution is simple – don’t use your iTunes account as an iCloud account. However, if you’ve already done so, is there a way to shift your identity from one iCloud account to another? Certainly no simple way.

Multiple iTunes Accounts

iTunes was revolutionary in allowing users to share bought music among multiple computers and devices. When the App Store was launched, this spread to apps as well. Finally, a family could buy an app once, and use it on all their devices. Some developers hated this idea, but most embraced it (even if reluctantly). For those with a single account, this works pretty well. As someone who lives straddled between two countries, I can attest that when you have two accounts, not so much. I am required to have two accounts, because some apps are only available in one store or the other. For example, many transportation apps are different or only available in one country or another, and thus are not available in both.

In general, there is no problem with running apps from multiple accounts on the same phone. What happens is that you need to log into the correct store and purchase the app you need. It downloads and is linked to the device. Your single device is just taking up slots in two different iTunes accounts, not a real problem. Where things start to go wrong is when you are updating apps, particularly on the desktop. When downloading apps on your desktop in iTunes, it gets tripped up by the fact that there are apps from multiple accounts. It stops and makes you log in to the different account. Why? Why not allow one to be connected to more than one account? Just like you can have multiple e-mail accounts in Mail, you should be able to have multiple iTunes accounts in iTunes. Sure, one needs to be Primary, so it knows which store to show you, but when downloading apps you should not be made to switch back and forth. It’s inane and definitely cannot be described as ‘just works’.

While I was writing this I came across an even stranger occurrence. I had a mix of apps from both stores in my update queue, but if I clicked on apps from store A, it told me I was logged into store B, and needed to switch to store A. If I clicked on apps from store B, it told me I was logged into store A, and needed to switch to store B. Basically damned if you do, damned if you don’t. What was going on? I have no idea. I rebooted and everything updated quickly without having to switch stores at all. This kind of impossible problem is not something I’ve run across too much with Apple products, and it is therefore that much more disappointing.

Multiple iCloud Accounts

While multiple iTunes accounts might seem a minor issue that only afflicts people who spend significant time in more than one country, the issue of multiple iCloud accounts is a much more widespread problem. While a couple or family might share an iTunes account to share apps and music, they can’t share an iCloud account. Which iCloud account you’re connected to determines the identity of your phone in reference to iMessage, FaceTime, your calendar, your e-mail, etc. If a couple shared their iCloud account, they wouldn’t be able to message each other.

A pretty common problem, so you’d think there would be an elegant solution to managing your identities on your iOS devices and Mac OS X computers. No so much. That a single account can be both an iTunes account and an iCloud account is possibly the root of the problem. It would be nice if there was a way to associate multiple iCloud accounts as sub-accounts to your iTunes accounts, allowing them access to your apps, music, books, etc. but not accessing your personal data.

The iBooks Conundrum

iBooks and iCloud

I have my computer and iDevice set up with my iTunes/iCloud account. My wife has her computer and iDevice set up with my iTunes account and her iCloud account. This is how it’s supposed to work. We share apps, and that works great. I wanted to share iBooks as well, and here’s what happened.

I added some books manually to my iBooks on my Mac. These were books in epub format. I created several Collections to divide the books. In theory the books should then sync my my iPhone, and my wife’s Mac and iPhone. Right? No. Here’s what happens. The Collections, which are essentially folders, sync everywhere. What was in them, not at all. So I find empty Collections spread all over the place. If I delete the empty Collection on my wife’s computer, it deletes it on mine (and all my books get thrown into the general ‘Books’ section).

You might be thinking that I need to set ‘All Books’ in the Books section of iTunes on my Mac. You’d be right, partially. I went into iTunes and realized that only a few books were set to sync (from a previous attempt to use iBooks no doubt) and I set it this time to ‘All Books’. I synced and lo and behold all my books were on my iDevice. Great. Well, sort of. The first thing I noticed was that while I had ordered the books in their Collections a specific way manually on my Mac, they were not ordered that way on the iDevice. You can re-order them again on the iDevice, but why if you took the trouble to order them on your Mac should you have to do it again on your iDevice?

So they’re on my iDevice. What about my wife’s? No, of course not, because iTunes manages the connection to your specific devices. My wife has her own iTunes and iDevices. So why do the Collections sync over? Of course Apple let’s you sync books that you bought through the iTunes between devices. If I had bought the books via iTunes they’d show up happily everywhere. Since I didn’t but them via iTunes, they’re not ‘in the cloud’ and thus do not sync. Why can’t books you add yourself be synced to the cloud? You can pay for extra iCloud storage, but Apple’s own iBooks won’t store those books in your iCloud storage space?

Keep in mind, this is how Apple advertises iCloud on their site:


I guess the emphasis is on ‘Your’ and not on ‘everywhere’. Perhaps there should be a footnote to the above that reads:

“As long as your music, movies, apps and books were purchased through the iTunes Store. Any content added directly to your device using the supported features in iTunes or iBooks will not be synced through iCloud, but must be manually moved to each device”

Not as sexy as ‘just works’.

Consolidation of iMessage and FaceTime

Not so long ago, you could chat using text and video with your friends using Apple’s AIM-compatible iChat client. iChat went even further and allowed screen-sharing in a very simple way. When Apple started deploying it’s own messaging and video solutions to the iPhone, it left iChat behind and created iMessage system (using the Messages app) and FaceTime for video (and later audio) conversations.

As Apple sought to bring the Mac in line with what is was doing with iOS, it dropped iChat altogether, and replaced it with a Mac version of Messages. It appears that Messages does have some of the legacy support of iChat, including support for video chat with AIM members, and screen-sharing, although I’ve had trouble getting my AIM account working in Messages. I can log in using the web to my account, but not via Messages. No idea why.

It also brought FaceTime to the Mac, but like on iOS, as a separate app that shared only its identity points (your phone number, e-mail address, etc.). If you’re video chatting with a friend through FaceTime, you can’t automatically send them a text message (such as a link to a web site) without opening another application altogether.

This is frankly just silly. Why have two apps that link to the same identities, but not work together? Why have two apps that do video chat? It’s a bit absurd. I understand that Apple’s initial goal was to built these features as system-level features. FaceTime was actually working like that on the iPhone initially, but eventually they went back on that and added an actual FaceTime app. Apple needs to work to bring all of the text/audio/video chat technology under one spot, and let it all work together. If I’m on FaceTime, why can’t I initiate a screen share? or send a link? Why can I initiate a FaceTime audio call from my iPhone but not my computer? These inconsistencies need to be resolved.

So what are your thoughts on iTunes, iCloud, and using them with multiple people, accounts, devices, etc.? What works for you and what doesn’t?


The first public introduction of the Macintosh was in Boston

1984 Mac Introduction at BCS

In 1984, Apple famously announced the Macintosh on January 22 in the iconic Ridley Scott directed ‘1984‘ commercial during the Superbowl. Not well known is that the ad was actually shown a few months earlier to a group of computer dealers behind closed doors. The ad announced the imminent launch of the Mac on January 24th, 1984.The Mac was indeed introduced on the 24th, at the Apple Annual Shareholder’s Meeting, and was to become available publicly hours later.

Video of the shareholder’s meeting was found on a Betamax tape in 2004, and released online in 2005. For a bit of history behind what happens in that video, see Andy Hertzfeld’s great description on his site called The Times They Are A-Changin’.

The initial introduction was to Apple’s shareholders who went to Cupertino, CA, and was not open to the public. The first public introduction of the Macintosh was actually six days later, across the country in Boston, MA. It took place at a meeting of the Boston Computer Society (BCS). BCS was run by a 20-year old college student, Jonathan Rotenberg, who had founded the society in 1977 at the age of 13. At its peak, it was the largest computer user organization in the world.

I myself spent a summer volunteering for the BCS in the late 1980s – biking 12 miles round trip each day to and from their office in downtown Boston. I remember Jonathan Rotenberg, and seeing lots of people come through the office there, including most memorably Richard Stallman. I’m not sure why Richard Stallman sticks out in my mind, but he’s an interesting person and I remember next seeing him in 1998 at the first LinuxWorld Conference in San Jose, CA (where he spoke on a panel about the ‘future’ of Linux with Eric Raymond, Guido Van Rollum, Linus Torvalds and Larry Wall).

In any case, it is not thus surprising that when Steve Jobs wanted to introduce the Macintosh at a meeting open to the public, he did so at a meeting run by the Boston Computer Society. It was the pre-eminent computer user organization, and if you watch the presentation from the shareholder’s meeting, you’ll notice this one is similar in script, but very different in presentation. In the shareholder’s meeting, Jobs is presenting to, well, shareholders. There is a technical presentation, but also discussion of cash flow and other mundane information. This presentation is to the users. The enthusiasts. The people who were going to buy the Mac. You can see that Jobs is more in his element here, preaching to the choir, and that this is perhaps the first of what Jobs would much later become famous for – his slick keynote presentations.

Of particular interest is the Q&A session in the second half where users asked all kinds of questions of Jobs and the whole Macintosh team. I liked this answer at one point: “We hope to put a Macintosh in a book, with flat-panel technology” – well Jobs did in fact do that, although quite a few years later.

Here’s the video:

For some background on this video, and how it was restored and put together, see the article on TIME magazine’s web site.