Back in mid-1993, I was working as a Financial Analyst for Apple in Cupertino; I'd been there for a few years, and had recently taken on a new role with a group called Software Dispatch. Software Dispatch was a new business, launched in those halcyon pre-Internet days, to distribute software on CD-ROM. And not just Apple software, but software from many different developers—there were over 80 signed up for the inaugural CD-ROM. (The official press release is an interesting read.)
On the CD-ROM, users would find encrypted versions of each app, along with a demo version they could use to try before they bought (see, Apple, you can sell software with trial versions!). If the user liked what they saw, they'd call a 1-800 number, pay with a credit card, and be given a decryption key to unlock their software.
But what made the business really unique for Apple in 1993 was that Software Dispatch was planned for Windows machines, too. I still remember how odd it was to see Windows machines on developers' desks when I walked through our area—there just weren't many visible Windows machines on the Apple campus at that time. While Apple had little trouble signing up Mac software vendors for the CD-ROM venture, it was different on the Windows side. And that's what led to the strangest business meeting of my career…
What could be done in a phone call to a Mac developer ("Put my app on a CD that Apple is going to mail to thousands of buyers?! Sign me up!") would often require a face-to-face meeting on the Windows side ("Wait, you're from Apple?")
And that's how I found myself scheduled to fly to the east coast with a few members of our team to meet with IBM. We really wanted IBM's software on the CD-ROM, though today, I can't even fathom what apps that might have represented—IBM hadn't yet bought Lotus, for instance.
We spent a lot of time planning this meeting, as we knew we'd only get one shot at it. The strategy discussion even got down to the attire level: The boss let us know that because we were going to IBM, it was time to don the suits and ties to match their formal culture. (Having worked at IBM prior to Apple, I could certainly attest to this—you didn't even head for an informal meeting without making sure you had your suit coat.)
This was actually an important issue to address, because Apple's dress code (at least at that time) was simple: pretty much anything goes. I'm sure not much has changed in the years since I left Apple, but when I was there, if you showed up in a suit, people asked "So who are you interviewing with?" I still remember seeing a guy in shorts and a t-shirt playing frisbee with his dog…in the building! Clearly our typical Apple day-to-day outfits weren't going to fly for this meeting.
Finally the big day arrived; after making the trip to Somers, New York, we awoke and put on the fancy duds, then drove over to IBM's headquarters campus. I don't remember much of the pre-meeting time, other than sitting in an impressively large and imposing lobby for a while. When we were finally ushered into the room, that's when we entered the Twilight Zone.
There were three or four of us from Apple, all looking sharp (and probably uncomfortable) in our suits and ties…while the IBM PC guys were standing there in their khakis and polo shirts! We all stood there for a minute or so, each side looking at the other in bemusement and confusion. Finally, someone from Apple (I don't recall who) said something like "Wait, how'd you get our clothes, and what are we doing in yours?!" That got some laughs and everyone started talking.
I don't remember anything of the meeting at all, beyond one of the IBM people explaining "we're based in Boca Raton, Florida, and this is how we always dress for work. Our dress code is much less restrictive than the one up here in Corporate."
I'm reasonably certain Software Dispatch did ship at least one Windows software CD, but I don't remember if IBM's software was on that disc or not. I left Apple about six months later—I'm not sure if Software Dispatch "left" before or after I did, but it didn't live very long. But I have it to thank for the strangest business meeting of my career.