Jerry Garcia Life Lesson #8

Jerry Garcia Life Lesson #8

To make it big in the music business you need to know the right people, get several lucky breaks, listen to your producer and your label and generally speaking you need to be willing to be shaped by others. This was true when Jerry Garcia and members of Grateful Dead were growing up in the 1950s and ’60s, and to a large extent it remains true today.

Unless you find another way.

Jerry Garcia Life Lesson #8: Do It Yourself

Jerry Garcia and friends were masterful at finding a way. I believe, finding a way was in the air in the San Francisco circa 1967. Take the Diggers. They found a way to feed all the hungry kids in Golden Gate Park who showed up for the Summer of Love with no place to stay, little money or food and basically no clue. Sure, the Diggers redistributed other’s wealth to get the job done, but I don’t want to judge their Robin Hoodishness. I just want to acknowledge their “can do” spirit.

Grateful Dead was an ingenious outfit and they were not afraid to go it alone, or do it themselves. Thanks to benefactor Owsley Stanley (a.k.a. Bear), his money from the sale of LSD and his uncanny ability to make complex things, the Dead had a homemade but totally state-of-the-art sound system. The band later created its own record label, produced its own feature film and created its own mail order distribution system for concert tickets.


The band’s DIY ethos was in part a rejection of mainstream music business culture, but that’s not all it was. It was also about the balls out pursuit of innovative solutions. It meant creating something elegant and better than what existed before. I met Owsley in 1987, and we had a long talk in the car as I drove him from Alpine Valley to the Hilton in Lake Geneva. He didn’t say this, but I am pretty sure he felt the technology that the band relied on had to be good enough to compliment with the LSD people were taking. Put another way, bad sound could easily ruin a perfectly good trip and Owsley wasn’t about to let that happen.

Jerry was also an avid painter and illustrator throughout his life. He did attend art school in San Francisco for a short time, but like he did with most things he figured it out. And then some, as Jerry’s larger canvases were selling for $40,000 while he was alive. Today, his work (including prints) continues to fetch top dollar.

I should note here that Jerry was a super smart guy. He was witty, sharp, a great conversationalist and brilliant in a lot of ways. Jerry had the other essential qualities to go with it: curiosity, passion, charm and a great ear. He’s also a native San Franciscan, and this makes a difference because there’s a pioneering gene common to many residents of the city by the Bay. It’s not known as the “Athens of America” for no reason. In San Francisco so many things are possible, and this wide open approach to things — “if we can dream it we can do it” — was Jerry’s way.

It’s pretty clear to me that this lesson, about self-reliance, innovative thinking and not taking no for an answer, has impacted me in a large way. I didn’t study to become a copywriter. I just became one, by attending the school of hard knocks and by learning on the job. Same with hypertext markup language. I wanted to make websites, so I took an online tutorial in html and started building. That was in 1999 on slow days at the agency. Since that time, I’ve built many client sites, but also established myself as a leading ad industry critic (and champion) thanks to another DIY moment in 2004, when a former colleague and I started In 2009 I founded Bonehook, a guide service and bait shop for brands to serve the needs of companies making a difference in their customers’ lives. Clearly, I listened to Jerry on this one!

By the way, doing it yourself doesn’t mean flying solo. When you combine the DIY ethos with superior teamwork, magic happens.

Previously: Jerry Garcia Life Lesson #7: Explore

Jerry Garcia Life Lesson #4

It is fashionable today to “fail harder” and to “fail faster.” These concepts from the worlds of communications and technology are meant to take the sting out of failure — the purpose being to encourage the kind of risk taking that accelerates growth and positive change.

Jerry Garcia Life Lesson #4: Take Risks

Playing it safe wasn’t Jerry’s way. He was an explorer, and by definition explorers take calculated risks. Sadly, when explorers lose their way, they can also lose their ability to calculate. Such was Jerry’s burden when it came to hard drugs, heroin in particular.

But it is not heroin, it’s LSD that is so closely tied to Grateful Dead and its musical risk-taking. The band and its songs were a jumping off place for the musicians and for the fans. LSD too is a jumping off place, and when you mix the two — Grateful Dead and LSD — you’re in for an epic journey. The band’s hyper-extended song, “Dark Star,” is certainly an epic journey. Performed live in concert “Dark Star” often clocked in at 30 minutes or more. What kind of band plays a song for more than 30 minutes? A band that wants to explore the kind of big ideas that need nearly infinite space to develop.

A band that plays a song this intricate and this long has immense trust in its own ability to pull it off, and in the audience’s willingness to stay interested and involved. LSD fueled the ideas that led to the creation of songs like “Dark Star” and “Birdsong” and LSD made listening to these acid-dipped songs all the more interesting. There’s no removing the LSD from the story or the historical record, nor should there be. Taking LSD was a risk that paid off in many positive ways for the band, for its generation and for new generations of people attracted to the music and to an authentic journey into the mind and self.

On another front, some of the risks we took to see Jerry perform may have seemed extreme to friends, coworkers and relatives at the time. In the summer of 1990, I mail ordered for the complete Europe Tour which was scheduled for October. I had never gone “all in” before. That is, I had never attended every show of an entire tour before, and here was my chance to do it and do it right. I asked for a month-long leave of absence from my job as Operations Coordinator at Conservatree Paper Co., a recycled paper merchant in downtown San Francisco. My boss said sure, but his boss said no way.

Big boss man’s name was Alan, and I recall vividly how Alan asked me what this trip to Europe was all about. I said I’m 25 and I’ve never been to Europe and now’s my chance. He asked why now? I said I’m going to see Grateful Dead in four European countries, is why now. He exclaimed, “People don’t do this!” I said I’m a person and I’m doing it. I added the only question was whether he wanted me back in four weeks. He did not.

Was it the right thing to do, quitting my job to see Jerry? That’s a rhetorical question. Of course it was the right thing to do. I knew there was a time-limit on the scene. That was made very clear to all in 1986 when Jerry slipped into a heroin-induced coma and nearly died. Trouble ahead, Jerry in red. But I digress. I knew, like we all knew, that there would be only one more chance to see Grateful Dead in small venues in Europe and that chance was going to take place during the month of October 1990. I also knew that a new job and new work would be waiting back home, so I didn’t mind taking the risk, not at all.

Europe tour 1990 was special in a lot of ways. For one, we all traveled by train so the experience was a collective one. In the U.S. after a show, you tended to go by car (or bus) to a nearby hotel or to a friend’s house. Lots and lots of little parties after and before the shows. In Europe, 3000 American Deadheads moved pretty much as one, by train, from city to city. This kind of travel made it easy to meet new people and make new friends. It was an epic adventure full of calculated risks, and I am better for having had it.

Previously: Jerry Garcia Life Lesson #3: Defy Convention

Jerry Garcia Life Lesson #3

Jerry Garcia Life Lesson #3

You have to learn the rules before you can begin to artfully deconstruct them. Of course, all serious artists and thinkers do learn the rules first, it’s the artful deconstruction that eludes so many.

Jerry Garcia Life Lesson #3: Defy Convention

Jerry Garcia grew up in the 1950s–a time of mass conformity in America, San Francisco included. So, where did he acquire the gigantic nut sack it took to dream his own dreams, think his own thoughts and live his own life? I can’t say for sure, but this kind of inner confidence is typically the result of strong parenting.

Jerry also grew up in the Mission District, and while he was a very affable and generous soul, he was also a relatively tough guy from a tough part of town. And tough guys from tough parts of town don’t exactly flock to art school, but Jerry did. He defied convention and the odds, time and again.


I remember driving from Salt Lake City to Tahoe and seeing Jerry Garcia Band perform at Squaw Valley in 1991. Jerry announced from the stage on the first day that he and David Grisman, who were slated to headline the next day would instead play earlier in the day. Jerry felt that The Neville Brothers ought to headline the Sunday festivities, so he defied convention and Bill Graham Presents by rearranging the schedule on the fly, much to everyone in the audience’s liking.

The Neville Brothers are a high energy dance band from New Orleans and they belonged in the headliner’s slot. Jerry’s humility and respect for his fellow musicians put the Neville’s in the spotlight that day on the mountain. His willingness to let his conscience guide him and his readiness to speak up to right a wrong, showcased his personal integrity in an unforgettable way for me that day, and again it speaks to his inner confidence. A lesser man would have never volunteered his headlining spot on the ticket — that’s simply not how show business works.

And frankly how show business works was never much of concern for Jerry and Grateful Dead. They formed their own record label, designed their own sound systems, sold their own concert tickets via mail order, made their own feature film, and so on. Grateful Dead also played concerts at the Pyramids in Egypt during a full eclipse of the moon. They did it themselves, and it was all a great big adventure. Not everything went as planned all the time, but that’s a price you pay for taking risks, for going your own way, for defying convention.

Oddly enough, defying convention has proven one of the more difficult lessons from Jerry’s life, and one many of his fans fail to understand or practice. Deadheads are followers, not just of a band but of one another. It’s a tribal culture, as are all sub-cultures, but there’s a BIG issue with tribalism as practiced by white neophytes with no grounding in the realities of living in a tribe. The problem is group think and group do. When everyone wears the same clothes, likes the same drugs, listens to the same music, lives in the same cities, drives the same cars and adopts the same look, I am sorry to say it’s a convention of non-conformists, which kind of defeats the point.

Previously: Jerry Garcia Life Lesson #2: Improvise