What Digital Business Can Learn From the Grateful Dead

Brian Pagano
APIs and Digital Transformation
6 min readJun 30, 2017

Written by John Rethans and Brian Pagano

Arrows of neon and flashing marquees out on Main Street.

Chicago, New York, Detroit and it’s all on the same street.

Your typical city involved in a typical daydream

Hang it up and see what tomorrow brings.

-The Grateful Dead “Truckin”

Houses in the San Francisco Peninsula are designed to cool off as the evening breeze comes onshore — which means that many of us living in Silicon Valley endure summer temperatures with no air conditioning.

Waiting for said breeze in the stifling heat over the past few evenings, we’ve devoured Long Strange Trip, the documentary about the Grateful Dead. While watching, we were struck by the idea that this band of merry pranksters learned many lessons which are also crucial to pioneering digital products in Silicon Valley.

Many of the themes that run through the Dead’s long-lived success and impressive creative output apply to the challenges the customers we work with every day as digital strategists. Yeah, we know you don’t believe us. Yet.

Obsessively focus on creating the best possible user experience- then optimize.

When you see footage of one of their concerts, you’ll notice the enormous wall of speakers stacked vertically behind the band — the fabled “Wall of Sound.” You might think the roadies got over-excited and just kept piling up the gear, but the construction of this monster was very calculated to create a pleasurable listening experience for the entire audience, even those seated far from the band.. But how far back could you be and still get great sound?

The Wall of Sound created perfect sound up to a mile away from the stage! At thirty-two feet tall, Phil Lesh’s bass stack emitted a perfect sine wave.

Notice that first the group got their music down. The practiced and played and performed and practiced — all to please their listeners. Then they got their amplification down to ensure every concertgoer could hear a blissful sound.

For a time, the chaotic process of building up the giant speaker wall, tearing it down, and transporting it drove the band into the ground, but by the late eighties, their road crew had become a well-organized machine — able to set up for great amplification efficiently, without sacrificing the experience.

How does this apply to Silicon Valley and digital business? Don’t optimize until you have the experience down.

Telling people no sucks. Giving things away for free makes you popular.

Most bands clamp down on anyone trying to record or distribute recordings of their shows. The thinking is that the band will lose the potential revenue from those recordings, which thus they must be stopped. This seems logical.

A lot of companies feel the same way — especially about their API program. These companies think of their APIs as access points to their valuable data and proprietary digital assets, so they keep their APIs under lock and key, locked down under strict governance processes with approval processes and decision-makers at every level of the bureaucracy.

On the other hand, Tim O’Reilly famously said, “For a typical author, obscurity is a far greater threat than piracy.” And this also seems logical, though less intuitive. There is no way to make money from your art if nobody knows your art exists.

Indeed, when people large numbers of people began recording bands’ music, it was actually a boon for The Dead. This taper movement drove the band’s popularity though its second and third decades. According to their publicist, taping grew their audience 3–4x with minimal label support.

This may remind you of a lot of the success stories emerging from companies doing digital transformation. These companies think of APIs as products that developers use to agilely create new digital experiences that extend their brands. They embrace agile, light-touch governance approaches, maintaining security, visibility and control while removing anything that blocks developers from creatively assembling APIs into new digital services.

The most sophisticated of these companies make their APIs available to others, enabling their services to achieve scale and reach far beyond what any company could achieve alone. Think about the many ride-sharing apps that use the Google Maps API, and how those ride-sharing apps often have APIs of their own, letting developers build ride-sharing functions, such as requesting a car, into still more apps. Digital business is about these sorts of ecosystems and network effects, and they all start with using APIs to turn existing systems and data into strategic assets.

The Dead’s agility resulted from a very simple premise — they didn’t want to police their audience. Jerry said, “Once I’m done with the music, the audience can have it,” indicating that once he had performed the song, his main part was complete. The fact that this asset could now be packaged, mashed up, distributed, promoted, consumed, and enjoyed by a multitude of eager third parties simply continued the life of this piece of art.

This is what an API does. It takes some asset that the company created and allows other eager parties (internal and external) to package, repackage, mash-up, distribute, promote, consume, and enjoy it.

The modern corporation is focused on optimization of an existing system, so the natural reflex is to saddle digital efforts with the same level of control — which often kills the initiative before it can even begin. Let the assets flower into APIs. Let the APIs blossom into a garden of consumption.

The Situation is the boss.

Jerry Garcia was a reluctant leader, wanting things to unfold rather than controlling outcomes. Any leader knows that the battle plan never survives contact with the enemy. So, in this respect, Garcia was right not to fall into analysis paralysis. No plan — no set of requirements — will ever be good enough.

On the other hand, this philosophy resulted in a certain level of chaos surrounding the band at all times — forcing leadership to emerge as needed. As the head of the road crew put it, “The situation was the BOSS.” Sometimes Jerry was the boss. Sometimes the road crew was the boss. Sometimes it was a truck’s broken carburetor.

For many business people, this approach may seem at best naive and at worst incompetent — but equally naive is the idea that a strict hierarchy can protect or prevent you from being buffeted by the winds of digital change.

Decisions are almost always best when made close to the context. The people nearest the problem have the most information and the most expertise. Usually this results in a good answer. Occasionally, this results in being blinded by too narrow a scope, being too close to a subset of the greater issue.

The Grateful Dead chose fully context-based management. Most companies choose hierarchical control structure, extensive requirements, and long-term plans. Guess where the optimal answer lies? Yup, in the middle. Sort of. But closer to the context-driven style.

Music is a conversation between parts.

One of the most striking comments in the documentary came from Jerry Garcia himself. He said that he wanted their music to sound like the individual instruments were having a conversation with one another. Some people complain that The Dead’s music sounds a little loose, almost sloppy.

But, once you understand what they are trying to achieve, your business can ascend to another level. Even in digitally sophisticated enterprises, some people complain that the relationship between business and IT, between ops and dev, between any parts of the organization, seems a little sloppy — but a little sloppiness can create a lot of agility.

Big organizations are trying to play a symphony. They envision a big, sweeping sonic wave that is the manifestation of unified vision, delivered by all the parts in perfect tune with perfect timing. This almost never happens in reality. Organizations should view themselves more like The Grateful Dead, with the different parts bringing their special sound and all having a conversation with one another. This is much more realistic than the symphonic approach.

To Be Dead or Not to Be Dead?

So the question is: can a psychedelic band provide good patterns for a modern corporation? In the case of The Grateful Dead, it certainly seems so. And look at this way, you can tell your boss that listening to a beautiful album like “American Beauty” — or better yet, Winterland June 1977 — is really research for innovation.

What a long strange trip it will be.

Haight Asbury image: Image By Tobias Kleinlercher / Wikipedia (Own work) [CC BY-SA 3.0 (http://creativecommons.org/licenses/by-sa/3.0)https://creativecommons.org/licenses/by/3.0/], via Wikimedia Commons

Ticket: Image By kansasphoto (Grateful Dead ticket for June 19, 1988) [CC BY 2.0 (http://creativecommons.org/licenses/by/2.0)], via Wikimedia Commons

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Brian Pagano
APIs and Digital Transformation

All about reading, language, mythology, music, and running. Don't mind video games either.