Bob Dylan can teach entrepreneurial secrets

His patterns toward musical success are similar to those of Apple founder Steve Jobs.

For the Minnesota Star Tribune
June 5, 2021 at 1:00PM
In this Jan. 12, 2012, file photo, Bob Dylan performs in Los Angeles. (Chris Pizzello, AP/The Minnesota Star Tribune)

Bob Dylan and his music have been famous nearly 60 years, since he came down from Hibbing, spent a season at the University of Minnesota and quickly became a legend in New York's Greenwich Village.

Dylan, whose 80th birthday was celebrated in events nationwide, can be thought of as a serial entrepreneur, the musical equivalent of Apple founder Steve Jobs — each famous in his 20s for unleashing a wave of creativity that spilled across the world, harshly criticized in midcareer for self-indulgent decisions and ultimately reconfirming his relevance.

What are some of the common traits Jobs and Dylan have shared in their careers?

If you are going to be a difficult person, be ridiculously talented. Both men became notorious for tales of rude or arrogant behavior. Fortunately, their talents dwarf their eccentricities, and neither has walked on the wrong side of the law.

Borrow, then innovate. Dylan and Jobs both immersed themselves in the best ideas available, then took them further. Dylan soaked in a wide variety of traditional folk music, R&B and poetry, while Jobs' team designed the Macintosh based on the pioneering work of scientists at Xerox's Palo Alto, Calif., research labs, which Xerox hesitated to bring to a wider market.

Marketing matters. Both men possess the ability to create a halo effect around their work. Jobs is generally considered the greatest marketer in the history of computing, for first creating a consumer PC market, then the "Cult of Macintosh," then the iPhone. But Dylan is in a league of his own when it comes to creating a mystique about himself and his music. An entire generation sought to find wisdom in his cryptic lyrics. (He insisted, pokerfaced, that they had no special meaning at all.) In his recent autobiography, he continues to spin his legend while querulously questioning why his fans gave special attention to his thoughts and activities.

Surround yourself with great people. Jobs surrounded himself with world-class technologists and managers at Apple, Next and Pixar. Dylan pursued the company of great musicians throughout his career. His 1960s backup group, the Band, achieved greatness independently in the 1970s. Later, Dylan toured with the Grateful Dead.

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