5 Lessons for Entrepreneurs From the Collapse of Woodstock 50

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We look at a recent Rolling Stone expose about the collapse of Woodstock 50 and share five lessons for entrepreneurs to never forget.

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On The BIGG Success Show, we discuss the pitfalls which sank Woodstock 50 and share five lessons for entrepreneurs. Here’s a summary of that discussion…

This show was inspired by an excellent article in Rolling Stone by Kory Grow about the fall of Woodstock 50.

Rolling Stone did extensive research for this piece: reporting for three months, reviewing about a hundred legal filings, interviewing dozens of associated people – e.g. artists, agents, managers, government officials, etc.

We hasten to add that there is definitely more than one side to this story. We’re not taking sides. The courts can do that. We’re just taking it as stated in the article.

We’re also not here to criticize. So we won’t talk about people by name. Instead, you’ll see us mention “the promoter(s)” and “the funder.”

We certainly make more than our fair share of mistakes too. That’s the expensive way to learn lessons. Our objective in this show is to extract lessons for entrepreneurs. It’s less costly to learn from others.


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Here are five lessons for entrepreneurs to takeaway from the collapse of Woodstock 50:

Lesson 1) Money isn’t everything

The author points out that Woodstock 50 was resource-rich: its iconic brand name, a moneyed global media company as a partner, and artists (and their agents) eager to join the show.

The funder had a budget of nearly $50 million for the event. The problem is – sometimes you can have too much money. Too much money may lead to less urgency. Too much money may lead to decisions not getting fully vetted. Too much money can lead to complacency and over-confidence.

2) Be optimistic, but deal with reality

At one point the promoter was talking with the funder about crowd capacity. We paraphrase here, but the conversation went something like this:

Promoter: Crowd capacity is 150,000.

Funder: I thought it was 60,000.

Promoter: Where did you get that idea?

Funder: From you.

Neither one was experienced in holding events like Woodstock 50 in the modern era. They hired an experienced company who eventually said capacity was 61,000. But the promoters pressed forward, planning for a crowd between 100,000 and 150,000.

We entrepreneurs are an optimistic bunch. But occasionally (okay, usually) you have to square up your optimism with the facts on the ground.

3) If it’s all about the money, you won’t make much money

Legendary musician David Crosby – one of the stars from the original Woodstock – is quoted in the article. He said (paraphrased):

“They tried to ‘magic’ it into happening. It wasn’t about people feeling good about each other. It was about a few people making a lot of money. It doesn’t bring out the best in people.”

Money isn’t the motivator for most people. They want to be part of something bigger. They want to feel like what they do makes a difference in the world – or at least a corner of it. You have to create a culture which communicates and demonstrates your vision and mission.

4) Be a doer, not a dreamer

The author quotes photographer Barry Wolman – who was snapping pics at Woodstock fifty years ago, talking about the promoter:

“He’s a dreamer. That’s the problem. He doesn’t know how to activate or realize the dream.”

Now, don’t get us wrong – dreams are an important PART of the process. But dreamin’ has to be combined with doin’. A lot of people dream and dream and dream and dream. It’s a worthless exercise until you do something.

Dreams are emotional. You should get emotional about your vision and mission. Then you need to get to work to fulfill your mission and make your vision a tangible reality.

5) Pick your (money) partners carefully

Funder seemed to constantly be pushing back about spending money. Of course, that’s not unusual. But your equity funder(s) need to think like venture capitalists, not bankers.

True equity funders – who look our for you as well as themselves – may very well tell you that you need MORE money. A banker may very well try to talk you into less. (They have to look out for their depositors.)

BIGG Takeaway

Dreams turn into nightmares without a well-organized plan.

Entrepreneurial Coaching

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Here’s to your BIGG success!

George “The Professor” & Mary-Lynn
signatures: George & Mary-Lynn
Co-Founders, BIGG Success

Direct link to The Bigg Success Show audio file | podcast:
http://traffic.libsyn.com/biggsuccess/00987-082119.mp3

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