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Longevity and Stagnation
What Bob Dylan, The Grateful Dead, and Warren Buffett Have in Common.
This past Christmas I went to see the new Bob Dylan movie, A Complete Unknown, with my family. The movie was enjoyable which isn’t an easy feat to achieve in the saturated musical biopic genre these days.
There are a couple things I credit this to:
1) Timothee Chalamet is a fantastic actor who is hitting his stride as a bonafide Hollywood titan.
2) Bob Dylan is unlike any of his musical contemporaries - his story is unique.

Bob Dylan (portrayed by Timothee Chalamet) walking the streets of Greenwich Village.
The movie covers a short span of Dylan’s career from 1961 - 1965. Over this period Dylan ascends to the pinnacle of fame, riding the crest of surging popularity in folk music and anti-war songs in America. But unlike most musical biopics, Dylan’s downfall in the narrative is not caused by alcohol, drugs, or an inability to handle fame (although those themes are present and certainly things Dylan struggled with). The downfall is instead caused by Dylan’s desire to “go electric”. To the dismay and disgust of his fans, Dylan replaces his trusty acoustic guitar with electric guitars and a backing band, shunning the musical style fans grew to love.
After the movie my Uncle and I talked about what made Dylan so popular and objectively great. On paper this Midwesterner had no business becoming the messiah of lyricism that fans appointed him as:
His voice was nasally, completely lacking the smoothness and tonal range we traditionally associate with vocal beauty.
His lyrics are ambiguous and difficult to decipher.
He lacks charisma and his personality is totally off putting.
In spite of these repelling characteristics, I think what makes Dylan so great is his refusal to stay stagnant. He was impossible to pin down, refused to be defined by any one political movement, instrument, or musical genre. When consensus zigged, he zagged, and this lack of conformity and total disregard for what others expected of him is what makes him such a fascinating and enduring figure.

Musical giant - John Coltrane.
“The risk is not changing. I have to feel that I’m after something. If I make money, fine. But I’d rather be striving. It’s the striving, man, it’s that I want.” - John Coltrane
Now that decades have passed and Dylan’s work can be evaluated in a complete context, many regard the electric instrument infused Highway 61 Revisited to be the peak of Dylan’s artistry with songs like Like a Rolling Stone and Tombstone Blues. If Dylan succumbed to audience capture and only produced music with which his audience was accustomed he never would have reached the heights of his musical career that history will remember him for.
Although he was called “Judas” by the fans who originally dubbed him the flag bearer of folk music, Dylan’s deliberate shift in musical style allowed him to garner appeal from a completely new fanbase. And while there were (and still are) some fans who will never forgive his decision, the move ultimately gave a new jolt of energy to his career.
Contrast this with one of the other artists covered in the film, Joan Baez, who stayed in the acoustic/folk niche her entire life and the difference is staggering. While Dylan developed a diverse portfolio of music that appeals to a vast swath of fans and fueled his career through different eras, Baez’s music remained “true” to her original contingent of fans and in doing so stagnated her commercial, creative, and musical success.

The Grateful Dead in one of its original forms.
One of the most enduring bands and cultural phenomena of the last 100 years is the Grateful Dead, a band that is infamous for angering factions of their audience by their decisions to change aspects of their personnel, sound, and style. Yet despite the regular uproar they cause among Deadheads, the band has endured in some form or fashion since 1965. In a strange twist of irony, the Dead’s refusal to stay still and appease the fans is exactly what’s allowed their legendary run.
If you listen to the Dead’s original record, the self-titled Grateful Dead, you get a taste of the acid soaked parties where The Grateful Dead originated. The songs are psychedelic, unorthodox, and unpolished. Songs like Cold Rain and Snow almost sound like a Sega video game soundtrack. Then a few years later the Dead released American Beauty and Workingman’s Dead, albums that are full of acoustic ballads and blues steeped in the folk and Americana genres that were popular at the time. Then in a further departure from the “Dead Sound” the band released Shakedown Street a funk fueled album evoking the 1970’s disco era it was birthed in. Like Dylan, the Grateful Dead refused to stay pinned down and their constant evolution allowed the band members to remain creatively interested while also welcoming new fans with diverse musical tastes into the fold.
Not only has the music changed, but the band’s personnel has remained in constant flux. Most infamously, the current iteration of the Grateful Dead, Dead & Company, consists of two original band members (Bob Weir and Mickey Hart), jam band contemporaries (Oteil Burbridge, Jay Lane, and Jeff Chimenti), and pop icon John Mayer.
The Dead has always associated with the counter-culture which is why the induction of Mayer into their ranks drew cries of Judas as original deadheads felt the band was going too mainstream and commercial. Yet Mayer is a world-class musician who has pushed the band back to its blues roots and generated appeal among younger, previously unreachable, generations.
The Grateful Dead is experiencing a renaissance six decades after their founding because they refuse to succumb to the whims of their audience and constantly seek new frontiers of their music.

Warren Buffett and Charlie Munger - the stewards of Berkshire Hathaway.
Charlie Munger once said of Berkshire Hathaway’s historical investment record - “The skill that got Berkshire through one decade would not have sufficed to get it through the next decade. Without Warren Buffett being a continuous learning machine, the investment record would have been impossible”.
Buffett began his career as a deep-value investor, only investing in things that traded below their “intrinsic value”. Then, after prodding from Munger, he wised up to the fact that great businesses trading at fair prices are often better investments than fair businesses trading at great prices as these businesses benefit from compounding, network effects, and strong brands that poor businesses don’t possess. Then, after spending the entirety of his career professing an inability to understand, and therefore invest in, tech businesses, Buffett went all in on Apple which now constitutes the majority of the Berkshire portfolio.
All of these evolutions in the investment philosophy of Buffett were necessary as the investment landscape changed. Ironically, almost every change in Buffett’s investment practices drew skepticism from his investors yet without any one of those changes Berkshire Hathaway would not be the $990B behemoth that it is today.

Bob Dylan and the Grateful Dead in 1987.
So what do Bob Dylan, The Grateful Dead, and Warren Buffett have in common? They were all learning machines that refused to remain still. They recognized that what caused their initial success would not necessarily ensure their future success. They followed their natural interests despite short term protest from their fans and investors. And that is what made these apparently ordinary looking men into enduring icons of American culture in music and business.
“I’m shopping around for something to do that no one will like.” - Jerry Garcia.