The Grateful Dead drops in at Apple

1986

The Grateful Dead was one of the most popular rock and roll bands in history. They played for more than 25 million people during their 30 year career. Pretty impressive! In 1986, my boss at Apple was an amazing character named Guy Kawasaki (now a best-selling author, popular podcaster, and avid surfer). Guy met Betsy Cohen, physicist for the Grateful Dead - go back and read that again if you need to - and he thought it would be cool if the Grateful Dead came to Apple to give a little private concert for us. He was right, it would be cool!

Guy knew the Grateful Dead was a huge band. Like the great manager he was and is, Guy delegated the task. Looking around his Apple Software Product Management team for an experienced concert promoter, and seeing none, Guy chose a 26-year-old nerd to arrange the concert: me.

In exchange for this concert, we figured we would send them a few Macintosh computers instead of money. (Macs we had plenty, money not so much.) So I talked to our connection Dr. Cohen and asked if they would play a small show just for Apple employees. She laughed and said they “don’t do bar mitzvahs.” In other words, they didn’t perform little private shows. OK, I said, how about if we send them some Macs to write songs with, and they come to Apple and give a presentation about that? Not a musical performance, more of a TED Talk (if TED Talks had existed then). She took that to the band and they said yes!

At that time, Apple was sending free computers to schools, a program called Kids Can’t Wait. So we figured we would send computers to the Grateful Dead and we called it (quietly, to ourselves) Rock Stars Can’t Wait.

We were set! We sent a Mac to the band, and we had the Grateful Dead coming to this little 400-seat auditorium at Apple. Now it started to dawn on us how popular they were. Now were worried about crowd control. We had no ticket system. Almost no security. We were terrified that we would have a mob scene of Apple Deadheads, and maybe outsiders too. So we really didn’t publicize the talk very much. On the day of the talk, it looked like maybe we had kept it too quiet. I sensed no buzz at all. So I ran around the building talking to people and putting up fliers. When the band showed up, the little auditorium was only about half full. At least there was no mob scene!

Deadheads and puppies

I got to be the host that day and introduced Bob Weir and John Perry Barlow from the band. They told us they had been creating a song with the Mac, which was not an easy thing to do back then. Music software was very primitive. There was no Logic, or Garageband, and no Internet to help out. Barlow told us they were working on the song a lot, and then the night before, the Mac crashed and they lost all their work! Of course we all felt terrible. Our beloved Mac killed a Grateful Dead song! The room went into mourning.

Then, amazingly, Barlow changed his tune. He said “OK, I have to tell you I actually made up that story. We never used a Mac to write a song. I didn’t even know you sent us one until yesterday.” There was shock, booing, and hissing. I asked Barlow, why did you tell us that fake story, and then admit the truth? He said “I suddenly realized this room is full of Deadheads. It’s bad karma to lie to Deadheads. Lying to Deadheads about this would be like drowning puppies.”

Later, Barlow said he never knew it before, but he was a computer nerd. I arranged to send him a Mac of his own to play with. He had many interests besides writing songs, like privacy and free expression. We became friends, the rock lyricist turned nerd and the nerd turned concert promoter. He invited me to Dead shows and I took him to Macworld Expo.

Barlow co-founded a group called the Electronic Frontier Foundation, which became the most important digital privacy and online free expression group in the world. He started writing a lot about these topics and became an expert and a visionary. The Internet got bigger and sort of took over the world, and so the EFF got more important too. And Barlow, bless him, once wrote that because I sent him a Mac, the EFF wouldn’t have existed without me. Which I don’t think is really true, but I put it on my resume anyway. Along with Concert Promoter.

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If you want to know more about John Perry Barlow, his life with the Grateful Dead and the EFF, and of course his visit to Apple, read his autobiography Mother American Night: My Life in Crazy Times.

I told a different version of this story on the award-winning television show John Wants Answers, hosted by my great friend John A. Vink.

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