Business Lessons from Bob Dylan

Posted September 17th, 2012 by bbsadmin & filed under General Business.

By Jon Friedman

You don’t automatically think of the iconic songwriter and poet Bob Dylan as an entrepreneur. But he sure is one — and a rather shrewd one to boot. He started from scratch and built up the Bob Dylan brand, now in its 50th year, to spectacular heights.

Dylan dropped out of the University of Minnesota during his sophomore year, determined to make it as a folk singer. He left the Twin Cities and arrived in Greenwich Village, New York City in January 1961, with no connections and very little money.

Dylan made his mark quickly. Within a year, he had played the harmonica at a recording session with Harry Belafonte, then one of the biggest stars in the music world, received a rave review in the New York Times and garnered a recording contract with a major label — Columbia.

This year marked the 50th anniversary of his writing “Blowin’ in the Wind,” his enduring civil-rights anthem. Tuesday Sony (which acquired Columbia some time ago) released “Tempest.” Thirty-five!

Talk about productivity.

Here, five entrepreneurial lessons gleaned from Dylan’s successes and failures:

Always have a passion for what you’re doing

When you are turned on by what you’re creating, you will recognize that the work is what matters. This will help you to get through the dark days, those times when you feel uninspired and dejected. Dylan plays about 100 concerts a year around the world. He no longer needs the money or even the fame or the acclaim to solidify his place in popular-culture annals. But clearly, this is a man who passionately believes in what he is doing.

See the big picture at all times and avoid the trap of the quick buck

Devise a game plan for yourself – even if you need to tinker with it along the way. Dylan writes in his excellent 2004 memoir “Chronicles, Volume One” about a meeting he had with an old friend named Bobby Vee in New York City in late 1961. Vee was then riding high, a prince of pop music, and Dylan was a scruffy folk singer on the way up. Seeing what his friend had become, confirmed for Dylan that he was on the right track: Dylan stayed true to his vision as a folk singer and it paid off brilliantly. As Dylan once sang, “Don’t go mistaking paradise for that home across the road.”

Don’t be afraid to rock the boat

The product known as “Bob Dylan/Folk Singer” was flourishing in 1965. He was selling out halls in America and England and young people held him up as the “Spokesman of a Generation.” But Dylan was restless; eager to grow and change. He decided to begin recording and performing with the rock and roll band accompanying him. Initially, his folk-purist fans were aghast and they solidly booed Dylan’s new incarnation when he toured around the world in 1965 and 1966. But he persevered and stayed true to his vision. Eventually, the fans came around. Bottom line: Dylan was not afraid to rock the boat and shake things up.

Seek inspiration from others

When Dylan was starting out, he sought inspiration and wisdom from the likes of singer-songwriter, Woody Guthrie. By the 1980s, he was in a creatively fallow period and once again needed to find people who could inspire him. He teamed up with Tom Petty and the Heartbreakers, the Grateful Dead and the Traveling Wilburys. The result? His 1989 album “Oh Mercy,” hailed as his best works of the decade.

Know when to go back to basics

Sooner or later, even the most dedicated and energetic entrepreneur hits a wall. It’s inevitable. The question is: How can someone turn that kind of a defeat into a victory? The answer: by getting back to basics and remembering what set you on your way in the first place. Dylan’s 1990 album “Under the Red Sky” was a critical and commercial disappointment. After its release, Dylan repaired to his home studio in Malibu and recorded a pair of albums of acoustic songs, the kind he had performed as a teenager. That got him back on track and the next album of original songs, “Time Out of Mind,” ultimately won the 1998 Grammy for Album of the Year.