Happy Birthday to Us! TMO Turns 20 Today

TMO Circa 2000

The strangest thing happened today: The Mac Observer turned 20 years old today. One more year, and we can drink! On December 28th, 1998, Dave Hamilton and I relaunched “Webintosh” as The Mac Observer, and it’s been an interesting two decades since.

He and I talked about our beginnings on Friday’s Daily Observations with Kelly Guimont, so I won’t rehash that story here. Instead, I’ll talk about some of the things that changed during that time.

The Mac Observer circa 2000
The Mac Observer circa 2000

Firstly, Dave and I both moved away from Austin, TX, where we met and started this business. Dave went back East, and I went so far West, I made it all the way to the Far East. Japan, to be specific, where I ran TMO for three months. I then moved to Silicon Valley and watched rent prices go from stratospheric to OMG WTF HAPPENED TO ME?!?!

In the intervening years, Apple went from beleaguered to crazy to fabulously successful, while somehow managing to stay doomed the whole time. At the same time, the market TMO competes in went from “The Mac Web”—because the main stream press (there was no real “tech press” yet) ignored Apple—to every major news publication and organization having one ore more reporters dedicated to Apple.

When we started, there were no podcasts. There wasn’t an iPod yet. When the iPod came out, I whined about it having only 5GB of storage, and everyone and their brother said the name was stupid and it would fail.


The iPhone and iPad were both released, and despite all manner of prognostications to the contrary, both are also the cash machines the rest of the industry struggles to copy. We covered Apple moving to OS X, moving to Intel, and releasing Phone OS (later iOS). We covered the release of Apple Watch, The Cube, Xserve, iPhone 5c, Hi-Fi, iWork, iDVD, Logic, Keynote, iPod Socks, that weird, ugly iPhone case with a hump on the back…and a bunch of other things. Some quickly faded away, and some were huge hits, but covering all of them was fun.

We also covered the passing of Steve Jobs and the ascension of Tim Cook. We were there when the first Apple Stores opened, and our own Kyle D’Addario was hired away by Apple to be one of the first Mac Geniuses. iTunes Store, check. App Store, check. Mac App Store, check. iBooks, check. Ping, check…what, too soon?

Dave Hamilton and John F. Braun launched The Mac Geek Gab, and Dave had the big idea to take some of the things from our morning meeting and turn it into TMO’s Daily Observations. Ricky Spero has this weird idea of doing a “Weekly Roundup” audio show, too.

Today, we have a multi-continental crew that features (in no particular order) me, Dave, John Martellaro, Andrew Orr, Charlotte Henry, Kelly Guimont, Melissa Holt, Bob “Dr. Mac” LeVitus, Adam Christianson, and sometimes John Kheit, Dave Chartier, Chuck La Tournous, and the amazing Jim Tanous.

Other shoutouts (again, in no order): the previously-mentioned Kyle D’Addario, Jeff Gamet, Mike Washleski, Jeff Butts, Brad Cook, Nancy Carroll Gravley (hi, Mom!), Vern Seward, Rodney O. Lain (we miss you so very much), Brad Gibson, Wes George, Darla Sasaki, Raena Armitage, Dan Miller, and many more who have contributed to TMO over the years. There is simply no way to give everyone the kind of mention they are due, and we love you all.

And we also love our readers and listeners, many of whom have been with us the whole 20 years! I’d love to hear about your earliest memories of TMO in the comments, and here’s to the next 20 years.

21 thoughts on “Happy Birthday to Us! TMO Turns 20 Today

  • Bryan:

    First, Happy Birthday TMO!

    Since you asked about our earliest memories of TMO, I’ll relate mine.

    I had just moved overseas to conduct research and brought my Mac laptop (a PowerBook 5300) – oh, and my family, but I digress – in the summer of 1997 and was working in a Mac-hostile environment. I had to be my own tech support (this not being my first tour overseas I was used to it, but this was the first time I was carrying a Mac). I also brought a Palm Pilot (remember those?) which I would sync to my Mac. If memory serves, one of its features was to download news items by topic. I keyed in Apple-related news, as I was always on the lookout for tech tips and trouble shooting info.

    I don’t remember the year, so cannot say I began reading your content when you first launched, but at some point, I believe in early 1999, I became aware that I was getting consistently good news articles from this site called ‘The Mac Observer’, and began paying attention to every article from the site. The style and the range were different from the other Mac-related sites. At some point it dawned on me to stop waiting for the Palm Pilot’s news feed and just go to the website, which I did. I recall an article from one Bryan Chaffin early on that poured cold water on the idea that SJ’s return was necessarily good for Apple. My thought at the time was, ‘This guy’s an arse. This site’s going to fail’. Now I realise that I was wrong; the site didn’t fail. 😊 It was a particularly hilarious article, at some point, from the late Rodney O. Lain that cemented my being a regular reader, and I’ve never looked back. It would be years before I would post my first comment, but I regularly checked into the site. Curiously, that was not my behaviour with other Apple-related sites.

    Once the iPod launched, and podcasts became a thing, I regularly scoured the internet for Apple-related Podcasts. It was an article from TMO’s Vern Seward that alerted me to the launch of the MacGeek Gab. This podcast hit the sweet spot. It provided the ‘in the weeds’ tech support coverage that I really needed whilst in the field, and continues to provide that to this day. The Apple Weekly Report cum Apple Context Machine provided the in-depth topical dive that my analytical soul craved, without the rancour that some other sites succumbed to when opinions differed. It was the skit about the kid who got a Zune in his Christmas stocking, however, that made me a diehard fan (I think that my driver thought that I was either choking or deranged in the back seat, so I finally had to just laugh out loud as I listened on my iPod).

    I’ll close by pointing out the two features of this site that have won my support as a regular reader/listener/supporter.

    First is the range, not just of topics, but of subject matter; everything from tech tips, reviews, analysis, Op-Eds, timely public service announcements, not just on Apple products and services, as essential as they are, but related topics in the tech world that affect the Apple community. To my reading, these articles have been well researched and well written, balanced, thoughtful and thought provoking without being tribally hostile, untruthful or unfair to competing platforms. What comes across is a dedication to facts and truth, including when that truth is not kind to Apple, which is not infrequent (e.g. iTunes, Mac refresh cycles).

    Second is the platform for commentary, discussion and engagement of the readers/listeners. This is true for both the printed and podcast material. What has set TMO apart from most other sites (many of which have died off), in my view, is the commitment to encouraging free and open discussion in the comments sections without allowing these to degenerate into an orgy of personal attack, gratuitous vulgarity, incivility and opinionated bile. Apart from the latter, the only pushback I’ve observed from TMO is when a commenter is simply wrong on the facts. This is refreshing.

    The Apple world, and the tech world writ large, has and continues to evolve, substantially; and thus far, TMO have managed to evolve with it.

    Here’s to another 20 years, and beyond.

  • Wow! Has it really been that long? I (vaguely) remember Webintosh and the change to the Macobserver. I also remember the Macobserver IRC channel being a lot of fun. The Macobserver has always retained the top position in my bookmarks for information on Apple. Congratulations to Bryan, Dave and all of the TMO crew, on 20+ years of great work.

    BTW, Bryan, at Macworld in 2007 or 2009, I met your mom and we had a great conversation. She’s a very sweet lady. What the heck happened with you? 😜

  • Congratulations. Not many web enterprises last this long.
    I don’t know but I think I’m one of the longest lasting members still around, I joined in the earliest ’00s. The site has evolved over time. People have come and gone. (Does any one else remember Rodney O. Lain? The period when the Motley Fools did a column?). One thing I’ve kept coming back for was the thoughtful commentary, and the quality journalism. Where other sites have been overrun by snark and trolls, TMO hasn’t. Where other sites are fawning and effusive of Apple even when they screw up, TMO isn’t. You call a spade a spade. When Apple does something stupid, or just plain wrong, you call them out on it. I respect that.
    Congratulations on 20 years.

  • I haven’t been here the whole 20, but 18 or more. I used to read your articles from….. macsurfer.com. Is it still around (runs and checks–yes it is!). When Google came out with their Reader service, I kind of stopped using MacSurfer, but you guys made it to my RSS feed and have stayed there since. I don’t comment as much as I used to (this is pretty universal in my life. I’m far less active online than I used to be), but I still read your stuff every day.

    TMO is still just about the best, most insightful source of Mac and Apple news that is out there. I know that when the hyperbole goes off the charts, TMO will have the rational perspective–that isn’t always pro-Apple.

    Thanks so much for what you have given over the past 20 years! Congratulations, and looking forward to 20 more years and more! 😉

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