Microsoft and Apple hit the road

1997

In the mid-1990s, after years of neglect, Microsoft got serious about making proper software for the Mac. They set up an office in Silicon Valley and gathered a team in Redmond to work on Mac Internet and Office software. They recruited a bunch of Mac veterans, eventually including me. When we shipped Office 98, the marketing folks set up a roadshow to demo the new software at Apple offices around the country. Yes, there were Microsoft demos at Apple offices! The companies were in a rare buddy period and were working closely together. There was even co-branded stuff with both Apple and Microsoft logos.

Two amazing artifacts: above is a CD sleeve with Apple, Mac OS, and Microsoft logos coexisting on the same surface. And a dumb sticker added after printing the sleeves because somebody forgot to get it printed on the back where it belonged. Below is a polo shirt with Microsoft and Mac OS logos. This was our uniform for the Microsoft booth at Macworld Expo in 1997.

The marketing folks felt I was good at giving demos. Demos are just another kind of stage performance, which I love. So they asked me to go on the 5-city tour and give the Office 98 demo to customers. This demo was an in-depth hour-long tour of Office 98 on a Mac, part of a half-day program that also included an Apple person talking about what was new with the Mac hardware and system software. The plan was for morning and afternoon demos each day, 10 demos in 5 cities in 5 days. A whirlwind trip to do software demos sounded like fun to me, because I am such a nerd.

The tour schedule for the week:

• Monday: Dallas

• Tuesday: Atlanta

• Wednesday: Washington

• Thursday: New York

• Friday: Boston

Microsoft sent four of us on the tour, along with the Apple person. We would get to the local Apple office by 8 am, start the first demo at 9, finish by 1 pm, take an hour for lunch, do another show from 2 to 6 pm with a new audience, then pack up and race to the airport to fly to the next city. Sounds crazy, no?

Invitation cards were mailed to customers. Note the schedule; I didn’t go to the first four cities.

The pace was intense. I was having a blast showing off the software. There wasn't any time to go out for lunch, so we had to rely on whatever was brought in to the Apple offices, which varied widely. Dinner was worse: we never had time for it, because we had to rush to the airport. If we were lucky, there were still places to get something to eat at the airport in the evening. Otherwise it was vending machines and leftovers.

On Tuesday, we stayed at the Doubletree Hotel in Atlanta. We got there around midnight and had some of the famous Doubletree chocolate chip cookies for dinner. That was tasty. But not very filling or nutritious.

Delicious artificially intelligent chocolate chip cookies.

By Wednesday in Washington I figured out that we were never getting a decent dinner. Plus, the Apple office that day provided tasty sub sandwiches at lunch. Clever guy that I am, I stuffed an extra sandwich in my bag for dinner. I was set. When we got to the airport, late as usual, I looked in my bag to find the delicious sandwich had leaked Italian dressing on everything. It’s a good thing we didn’t travel with laptops in those days. That bag smelled like a deli for years afterward (actually not such a bad thing).

Sandwich, inadequately wrapped, made with meat, cheese, veggies, and AI.

On Wednesday night we flew to New York, my first time there. Microsoft's travel department had booked us at the legendary Waldorf-Astoria. The Waldorf-Astoria! I figured I'd never be back there again on my own dime (true so far). Although we checked in very late, room service was still available. To celebrate my first trip to New York, I ordered a New York steak with New York cheesecake for dessert. I probably thought that was really clever. Since I personally wasn't paying (sorry, Microsoft overlords), I also took a $29 jar of peanuts in a Waldorf-Astoria logo jar. I still have the jar but not the peanuts. I also took a logo pen and a shoehorn. They were “free.”

This one is a real photo by the author

Another real photo. This is a shoehorn (not the kind with teeth.)

After finishing our NYC demo sessions, traffic and weather conspired to get us to JFK airport very late. No shops or food counters were open in our far-flung terminal. There was a Panera Bread cart, but it was just closing for the night. We hadn't eaten all day and begged the Panera folks to sell us some bread, but they declined. We watched hungrily as they put all the leftover bread into a large plastic bag. "Can we buy that bread?" I asked. No. It was going to the homeless shelter.

The Panera person finished bagging the bread, put the bag on the cart, and left. The four of us debated what to do. It was late. We were hungry. All the shops were closed. We made our fateful decision. Once we were sure the Panera person was out of sight, we opened the bag and carefully selected a few rolls and pastries. We closed the bag up again and left a $20 bill tucked under it. As we ate the meager dinner, I imagined the headline - “Microsoft Employees Steal Bread from the Homeless” - and thought it would be a bizarre way to get fired.

Flip side of the invitation card from the Office 98 roadshow. I asked my fellow road trippers to sign it as a memento, like a yearbook. They humored me.

On Thursday night, the last leg of the trip before coming home, after the Panera “dinner”, we arrived in Boston very late and got to the hotel at about 1 am. When I checked in, the desk clerk produced a box that had been shipped to me at the hotel. This was the first night of Passover, and my amazing wife had packed and sent a box of Passover food goodies for me to enjoy.

That was the best meal of the trip.