Fare Thee Well, Bobby

The first time I heard the Grateful Dead was in the smoking area of my high school. (Yes, high schools had smoking areas in the 1970s.) Someone had brought in a boom box and was playing Wharf Rat, the chorus emerging like an uplifting prayer: “I’ll get up and fly away.”

Around the corner, written on the light brick wall in black, permanent ink was a line that the grafitti artist foresaw as iconic: “What a long strange trip it’s been.” The Dead permeated my high school like tie-dye through the fibers of a white, cotton t-shirt.

Such was high school in the 1970s. While I’m not in the photo below, it’s the only one could easily find online, just to give you a taste. While I don’t know what happened to most of the folks in this picture, one later became principal of the high school. Another was killed in 9/11. But this was us.

Many of us became deadheads. Second only to their home state of California (847), the Dead played more shows in New York (289) than any other. Often these were in small municipal or college venues like the Glens Falls Civic Center, the Onondaga War Memorial, the Broome County Arena, or Barton Hall at Cornell, later famous for hosting what was generally deemed their single best concert.

I was first drawn to Phil because the tone of his voice was unique and I loved the high harmonies that he often sang. Then I was drawn to Jerry because of his souful voice, wistful ballads, stunning guitar leads, and well, who couldn’t be drawn to Jerry?

I didn’t know what a rhythm guitarist was. But that was Bob Weir, often simply Bobby, cofounding member but nevertheless kid brother of the band. He was only 17 when he joined, compared to Garcia at 21, and Lesh at the ripe old age of 25.

But I liked Weir’s high energy songs like Truckin’ and Sugar Magnolia, which often served as a gateway into the Dead’s music. And Sugar Magnolia contains one of my favorite Dead lyrics (“she’s a summer love in the spring, fall, and winter”) although it was penned by Robert Hunter.

A dispute with Hunter over the previous line — “she can jump like a Willys in four-wheel drive,” written by and classic Weir — permanently ended their songwriting partnership, driving Weir to collaborate with John Barlow going forward. Weir and Barlow would write some masterpieces together such as Weather Report Suite, a song so challenging to play that the band eventually stopped playing it.

But that was the Dead. A band that wrote songs that were too hard to play. The band that routinely played the most difficult thing that John Mayer ever learned. The band who built a public address system that was too expensive to transport. The band that wrote songs in 11/8 and 7/4 time signatures (The Eleven, Estimated Prophet). The band that encouraged bootlegged recordings with a dedicated “tapers” section. The band that provided medical and retirement benefits for its road crew. The band that pioneered a new category (“jam bands”), blazing a path in the 90s for Phish and today Goose.

These were people who pushed the envelope. And Bob was a big part of that. Perhaps the biggest thing Bob did in recent years was recruit talent to keep the band going. John Mayer, Oteil Burbridge, Jeff Chimenti, and eventually Jay Lane. Without Bobby attracting this talent, the whole scene might have died with Garcia in 1995.

In other posts, I’ve written about business lessons from the Dead and there are plenty. Innovation, disruption, open source, community, alternative business models, category creation, customer centricity. I won’t rehash them here. If I had to net it all out, I’d say read Brian Halligan’s book. He knows the Dead, he knows marketing, and — as a cofounder of HubSpot — he knows tech.

Those of us in community knew that, as great as it was, it couldn’t last forever. The Sphere shows were epic.

So were what turned out to be the final shows in Golden Gate Park. Particularly moving were the nightly guest appearances: Graheme Lesh (Phil’s son), Trey Anastasio, and Sturgil Simpson who knocked Morning Dew literally out of the park.

After Garcia’s death, Weir was once asked how often he thought about him. “Quite often,” Weir responded. “You know, he lives and breathes in me.”

And so it will be, Bobby, between you and us. Thanks for everything. Thanks for the long strange trip. Fare thee well.