(Originally posted on G+, here: https://plus.google.com/u/0/104945599561982033177/posts/Ggi4Ev1XVxL)
Working at Apple was my dream job - I wanted to work there, and specifically for Steve Jobs, since I could remember. Some kids want to be firemen. I wanted to be a programmer at Apple. I pretended to be sick so I could stay home from elementary school to write code. My ][e was my prized possession, and later an early Mac.
By a stroke of hard work and a little luck, I got recruited out of college all the way from east coast to come work for Apple, joining the MacApp team. Even though Steve had long been gone, it was still my dream job. To be very, very specific, I wanted to go work on the Knowledge Navigator. Since that job didn't exist (yet! Siri, way to go!) I took the MacApp job, as it allowed me to work on nearly everything that was coming out, new OS features and hardware, and mold them into something great for developers.
MacApp was a C++ framework that was used by developers to create applications, making the Macintosh Toolbox more accessable. It was a small team, and many of the brightest minds of Apple had worked on the project at some time. It was an incredible honor. I even got stage time at WWDC ('96) co-presenting an entire session on the latest MacApp version. I was far too young to realize how amazing this all was.
As MacApp grew long in the tooth, and the team changed (including the departure of +Greg Friedman to Microsoft, who was an amazing mentor and friend). I looked for a new opportunity, and transferred to the OpenDoc team. It was particularly nice because it was filled with great engineers, and, it was just the other side of the same building. I didn't even have to change where I park, just turn around after getting off the elevator at IL3 (the Apple building looking out on 280), rather than going straight to the frameworks team.
A few months later, the rumors started - we were going to be buying either Be or NeXT, although everyone seemed to think it was Be. I think we couldn't fathom, as a bunch of fanboys, that Steve might be coming home. Either way, an Apple icon was coming back (Jean-Louis Gasse is no Steve Jobs, but he had a "Apple Reputation", and it was particularly interesting, since Scully hand-picked Gasse so it was Jobs/Scully/Gasse Part Duex. People forget that little bit of drama.) Rumors also swirled that we were going to be bought by Sun, so it was hard to make sense of it all.
Without droning on about my personal history, Steve Jobs did come back. And, fairly quickly, killed off OpenDoc. I believe about 5000 people were laid off as projects that didn't fit the vision were shut down, and I was one of the unlucky. During WWDC '97, shutting down so many developer-related projects got a lot of attention, and he took some shots (and gave some out) about killing OpenDoc (see the videos below).
People who know how important being part of Apple was to me ask if I was bitter or angry. Long before Steve passed away, I've always maintained that I was neither of those things. I was sad, and worst of all, I felt like I let down my hero. I realize how cult-like and insane that sounds, but that really his how I felt, and still feel in a weird way. Again, I was far too young to really grasp what it means to get laid off; I didn't have a mortgage or family or anything to worry about, but I bled the Apple colors, and was so disappointed in myself for not delivering something so insanely great that Steve would consider Apple worthy. But, this changed me in a good way.
I'd probably still be an Apple employee if it wasn't for that moment. That's not good or bad, it's just fact. I learned so much in that time period - mostly from "doing it wrong" - about focus, product design, eating your own dogfood, and many more lessons, that it made me who I am, and made me a much better entrepreneur.
It turns out, I wasn't supposed to be at Apple, I was supposed to be an entrepreneur, I was supposed to change healthcare (who knew?!) and how chronic care is delivered. I was supposed to create,build, foster, and sell a great company.
If you look at what we built for health care - insanely focused on the patient experience (even stealing fonts from Apple! Sssh) and on a big vision of changing an impossibly failed system - I got to live my Apple dream, just, elsewhere.
The last few days were sad for me, because it brought back that feeling of never getting closure with those Apple years, that weird, almost parent/child desire to do something that would make my idol proud.
Like so many people I wish I could have said thank you. I've decided the best way to do that is to keep trying to change the world in the ways I think are best, that I'm insanely passionate about, to give back to others in the startup space and help them find that inner insanity, and carry just a little bit of that Apple-ness and Jobs-ness into everything I do.
It won't be about wearing a turtleneck or copying a catch phrase, but about the passion, desire, and willingness to do what I believe in, even when everyone else thinks it might be wrong.
Even though he's literally talking about something that caused great change for me personally, I find the two speeches below perfectly motivating.
(Update 10/8/2011: I just read Sam Altman's blog post on Steve's passing, and he has a sentence that summed up my feelings exactly: "I had disappointed one of the few people I cared about not disappointing" - that may be the trick to Steve's leadership style, to personally set a standard for those who simple want to be the best. Simple, obvious, effective)