My wife often notes that I wear a lot of T-shirts. She’s right. 100% cotton T-shirts are comfortable, stylish, and they allow me to express myself; whether it’s my devotion to a certain Italian racing team or making such bold statements as “I’m gonna come at you like a Spider Monkey,” “Will Work For Bandwidth,” and “The Internet Was Broken So I Decided To Come Outside Today.” But she also likes to remind me that I should probably get rid of some of my older shirts from time to time.

We disagree on that.

What she calls “older,” I call “vintage.” I’ve even gone so far as to tell her that some of these shirts are collector’s items… and now I have proof! Although, I did have to get rid of an old T-shirt to prove the point. So I guess that means we’re still at deuce on this one. Let me give you a little background:

Way back in the golden era of the Internet (that would be 1996 for you young’ins), I was an eager 25 year-old Product Manager in Microsoft’s newly-formed Internet Platforms and Tools Division. Microsoft had hired me right out of grad school, before the ink was even dry on my MBA. Man, I loved working at Microsoft in 1996. MSFT’s stock price was high, with a strong positive correlation to marketing budgets and morale. The IPTD product management team was made up of a bunch of hot-shots who had managed the mega-successful Windows 95 product launch a year earlier. Most of them who stayed at Microsoft are Group Managers and Vice Presidents now. I remember feeling like one of the Power Rangers, living in the freshman dorms, with nothing but Honors students… except that most of them drove Porsches.

As our team was brainstorming ideas to promote the launch of the latest version of Internet Explorer 3, I proposed the idea of giving away T-shirts to the first 10,000 people who downloaded the product on our launch date of August 13, 1996. We’d call it “Midnight Madness” and give away glow in the dark T-shirts with the IE logo that said “I Downloaded.” My crazy idea was approved, and I was told to run with it. I figured 10,000 shirts would last us through most of the day. I mean, this was the age of dial-up access, not that many people were online, and Netscape Navigator, our main competition, had a massive head start on market share. 10,000 shirts would be PLENTY, right?

Wrong.

All 10,000 shirts were claimed before 6:00AM on launch day. We did our best to get all 10,000 shirts to the winners, and Midnight Madness went on to be the most successful one-day product launch in the history of the company (I still have the “well done” email from Bill Gates). I left Microsoft later that year to pursue my own entrepreneurial interests, but I’ve remained friends with many of my former IPTD teammates.

Fast forward 14 years.

I received an email from one of my former IE teammates, asking if there was any chance I still had one of the Midnight Madness shirts. The current IE marketing team had launched a new blog, and the very first blog comment was from someone who jokingly complained that he’d never received his shirt after the download, and that maybe it was time for him to give up hope. The IE marketing team had tried to track down a shirt internally, with no luck. They had essentially given up on trying to find one, but Harry Goodwin, who still works at Microsoft and has remained a close friend, cc’d me on the email conversation and said “Hey Jenkins, any chance you still have one of these?” I immediately ran upstairs to my closet, opened the fourth drawer down, dug down three levels, and pulled out a well-preserved Midnight Madness T-shirt, which I had saved as a trophy of my favorite Microsoft memory. When I replied to the email thread with a photo of me holding the shirt with the caption of “Oh.. you mean this T-shirt?” the thread crowd went wild. The following blog post from Microsoft explains what happend next:

(click here for the rest of the story)