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.

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Happy Birthday, TMO.

Chuck LaTournous

<3 I’m proud to have been a small part of TMO history.

John Vestal

If you want to take a trip down memory lane, check out: http://web.archive.org/web/19990125100957/http://www.macobserver.com:80/

I have been a reader since that page was active. Congratulations for 20 years.



And yet at the time we thought it was great.

W. Abdullah Brooks, MD

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.… Read more »


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.… Read more »



John Kheit

Happy happy anniversary to you and Dave! A really big milestone and accomplishment, and something you fellas have every right to be super proud of!

Lee Dronick

Happy Birthday!


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… Read more »