Every Entrepreneur Has A Bob Dylan Moment – What’s Yours?

Opening Of The Rock And Roll Hall Of Fame And Museum

A version of this article previously appeared in Forbes.

Young Al Kooper did not miss his Bob Dylan moment. When Al was invited by Producer Tom Wilson to sit in on Dylan’s Highway 61 Revisited, Mr. Wilson made it clear to Al that he was a backup guitarist. He told him to sit quietly in the control booth and be ready to play if Dylan wanted to explore an arrangement that required two guitars.

According to Al, “Me being twenty one years of age and very ambitious… I decided I was going to play on that session.” However, it was quickly evident to Al that his services wouldn’t be needed, as Dylan’s primary guitarist was Mike Bloomfield, a more experienced and proficient musician.

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You Don’t Have To Beg Forgiveness, If You Get It Right

After several hours of waiting patiently, Al saw his chance. In his words, “They moved the organ player over to piano. So I said to Tom Wilson, ‘Why don’t you let me play the organ? I have a great part for this,’ which was total bull$hit. Tom Wilson said, ‘Ah man, you don’t play the organ.’ And just then, someone came in and got him to take a phone call. So he didn’t say, ‘No.’”

When Mr. Wilson left to take his call, Al rushed into the studio and sat down at the organ. The rest of the band assumed he was sent in by Wilson and that he actually knew the song they were about to record, which he did not.

Mr. Kooper picks up the story once Wilson returned to the control room, not realizing that he was at the organ. “Tom Wilson, (said) ‘This is take 7. Hey! What are you doing in there?’ Then you hear me laughing…” Before Wilson could say anything else, the “snare shot heard round the world” sounded and Kooper laid down one of the most iconic organ solos of the 1960’s. Per Kooper, “And that was it. That was the beginning of my career. Right then and there.”

The track was Like A Rolling Stone, which became Bob Dylan’s biggest selling song as was voted by Rolling Stone Magazine in 2011 as the Best Song Of All Time.

The fact that Al did not know the song resulted in one of the most distinctive elements of his performance. His playing is an eighth of a beat behind the rest of the band, because he was watching the chords Bloomfield was about to play. Kooper knew that he was taking a huge chance and that his margin for error was zero, given the aggressive way in which he had interjected himself into the session.

Despite having little experience on the organ, the song’s success caused Kooper to become one of the most sought after keyboardist during the next decade. He played on hundreds of albums, including those by: The Rolling Stones, B. B. King, The Who, The Jimi Hendrix Experience and Cream.

My Dylan Moment

Sadly, I have never sat in on a Dylan session. However, like all entrepreneurs, I’ve had multiple versions of my own Dylan Moments.

For instance, when I joined Computer Motion (NASDAQ: RBOT, merged with Intuitive Surgical), their immediate need was for a CFO. Even though I had passed the CPA exam, I had no desire to be an accountant, just as Al Kooper did not aspire to be an organ player. However, my career objectives aside, Computer Motion needed a CFO to help them raise money, so I took the role without hesitation.

Admittedly, I was not an all-star CFO. However, I was fortunate to recruit a fantastic finance team, which included people I worked with for over a decade, at multiple companies. With strong support, I was good enough to do the job.

My excellent financial team freed me to excel in the areas of my core strength: generating revenue. Although the title was not widely used at the time, I was essentially a CRO, traveling the world selling medical robots while we awaited FDA clearance. I was also instrumental in taking the company public, which provided me with a solid experiential foundation upon which I built the remainder of my startup career.

Luck Well Executed 

"The best wrestler is not he who has learned thoroughly all the tricks and twists of the art, which are seldom met with in actual wrestling, but he who has well and carefully trained himself in one or two of them, and watches keenly for an opportunity of practicing them." --- Seneca, Roman Philosopher

Luck, in part, entails preparation meeting opportunity. However, luck never arises absent the courage to execute flawlessly in the face of potential failure. If you do not seize your Dylan moments, you risk living a life of untested preparation and missed opportunities.

Many people allow their luck to unwittingly pass them by because they are driven by fear of loss, which paralyzes their ability to seize the moment. In contrast, successful entrepreneurs are driven by fear of losing out. They weigh an opportunity’s risks and rewards and when the chance for gain appears to be greater than the potential pain, they go for it.

I shudder to think where my career would have ended up if I had said, “No” to my Dylan Moment. Don’t say “No” to yours.

This article was inspired by a conversation with my friend and mentor.

Follow my startup-oriented Twitter feed here: @johngreathouse. I promise I will never Tweet about that killer burrito I just ate - just startup stuff.

Image Credit: Kevin Mazur/WireImage

John Greathouse is a Partner at Rincon Venture Partners, a venture capital firm investing in early stage, web-based businesses. Previously, John co-founded RevUpNet, a performance-based online marketing agency sold to Coull. During the prior twenty years, he held senior executive positions with several successful startups, spearheading transactions that generated more than $350 million of shareholder value, including an IPO and a multi-hundred-million-dollar acquisition.

John is a CPA and holds an M.B.A. from the Wharton School. He is a member of the University of California at Santa Barbara's Faculty where he teaches several entrepreneurial courses.

Note: All of my advice in this blog is that of a layman. I am not a lawyer and I never played one on TV. You should always assess the veracity of any third-party advice that might have far-reaching implications (be it legal, accounting, personnel, tax or otherwise) with your trusted professional of choice.

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