They Were Writing a Sitcom. They Accidentally Created Woodstock.
In 1969, two young guys, John Roberts and Joel Rosenman, were sitting in a New York City apartment trying to write a sitcom about a pair of amateur venture capitalists.
Not a bad premise, honestly. Two idealistic guys with more ambition than experience, stumbling their way through the world of business deals and big ideas. It had the makings of something funny.
The problem was, they needed material. So, they did something wonderfully entrepreneurial, they decided to go get some.
They took out an ad in the New York Times. It read, “Young Men with Unlimited Capital looking for legitimate companies and ideas to invest in”.
They expected a few calls. What they got was an avalanche.
So many good ideas came flooding in that Roberts and Rosenman made a decision that probably surprised even themselves; forget the sitcom, let's actually become venture capitalists!
The Ad That Changed Music History
Among the responses to that ad were two music promoters, Artie Kornfeld and Michael Lang. Hippies, by all accounts. Well-connected, passionate hippies with a vision; they wanted to build a recording studio in Woodstock, New York.
Roberts and Rosenman sat down with them. They liked the guys. They liked the energy. They did not, however, like the studio idea. The numbers didn't add up. The concept was fuzzy. It wasn't the right investment.
But here's where the story gets interesting.
Rather than walking away, Roberts and Rosenman looked at what Kornfeld and Lang actually brought to the table, their music industry relationships, their credibility with artists, their instinct for what the culture wanted; and they asked a different question.
What if, instead of a recording studio, we did a concert?
None of them had any idea what they were setting in motion.
What This Has to Do With Your Business
I tell this story because it's one of the most compressed illustrations of entrepreneurial principles I've ever come across. And every single twist in it maps directly to something I write about in The Amplified Entrepreneur.
Let's break it down.
1. You Can't Plan for the Right Opportunity, But You Can Make Yourself Impossible to Miss
Roberts and Rosenman weren't preparing to produce a music festival. They weren't even preparing to be venture capitalists. They were preparing to write a TV show.
But they did something that turned out to matter enormously, they put themselves in the path of opportunity by placing that ad. They didn't know what was coming. They just knew that if they stayed curious, stayed open, and stayed active, something interesting would find them.
This is what I call the Preparation Paradox, the irony that you can never know exactly what you're preparing for, which makes preparation more important, not less. The Contours couldn't have predicted that Berry Gordy would hand them a song meant for the Temptations. But they were in the studio, ready to work. That's why they got the call.
Roberts and Rosenman weren't in the music business. But they were in the business of being ready. And ready is what mattered.
The question worth sitting with; what's your equivalent of that NYT ad? How are you making yourself visible to the opportunities you can't yet see?
2. The Real Opportunity Is Often Hidden Inside the Bad Idea
Here's the moment that always stops me: Roberts and Rosenman said no to the studio. But they said yes to the people.
They recognized that Kornfeld and Lang's specific assets, their relationships, their credibility, their feel for the moment, were worth something, even if their particular idea wasn't. And rather than walking away from the meeting, they asked what else those assets could build.
This is one of the most underrated entrepreneurial skills there is. Berry Gordy had the same instinct when he saw past the Contours' two failed singles. Brian Epstein had it when he kept believing in the Beatles after Decca told him guitar groups were on the way out. The ability to look through a bad pitch and see the real potential underneath it is a genuinely learnable skill.
It requires you to separate the idea from the person. It requires you to ask "what could this become?" rather than just "is this good?" And it requires the flexibility to suggest a completely different direction while keeping the right people in the room.
In your business: how often do you walk away from a meeting because the specific proposal didn't work, when the right partnership was sitting right there in a different form?
3. Constraints Don't End the Concert. Sometimes They Make It.
Here's where the Woodstock story moves from inspiring to genuinely instructive.
Because of pushback by local citizens of other towns, two prospective venues canceled at the last moment. Cost overruns mushroomed. And then came the decision that defined the whole event; the organizers ran out of money to finish both the stage and the ticket fencing. They could build one or the other.
They built the stage. They tore down the fences. Woodstock became a free concert.
They expected somewhere between 50,000 and 100,000 people. Roughly 400,000 showed up. The food ran out. The portable toilets were overwhelmed. The medical facilities weren't remotely adequate. Then it rained. Then it rained more – a lot more.
And yet, by every cultural measure, it worked. Not despite the chaos, but in a strange way because of it. The unplanned openness created something that a tightly managed ticketed event never could have.
I've written in The Amplified Entrepreneur about how The Beatles made some of their most innovative music precisely because four-track recording forced them to think differently. The Rolling Stones turned a French mansion into a recording studio during tax exile and made Exile on Main St., one of their greatest albums. Constraints aren't obstacles to creativity. They're often the engine of it.
When I launched Netwurx Technology Group in 2004, we couldn't compete with the big corporate cell phone stores on resources. So, we competed on B2B relationships and high levels of service instead. What we couldn't afford to match, we turned into a reason to be chosen.
Roberts and Rosenman didn't plan to create a free festival. The circumstances created it for them. What they did was make the right call in the moment, protect the product, let the revenue model figure itself out later.
It's a hard lesson to internalize, but an important one. Sometimes the constraint is pointing you toward the better version of what you were building.
4. Being There Matters More Than Being Ready
One more thing worth noting about how Woodstock happened.
The Temptations got their opportunity taken away, in a manner of speaking, when the Contours showed up ready and willing. In the Woodstock story, it's almost the same dynamic in reverse, Roberts and Rosenman were only in the room with Kornfeld and Lang because they'd put themselves there, actively, through that NYT ad.
Opportunity is remarkably indifferent to whether you feel ready. It shows up when it shows up. The entrepreneurs who catch it aren't always the most prepared or the most experienced, they're the ones who were present when it arrived.
This is why consistency of effort matters so much, even during the slow stretches. The visible part of any success story, the festival, the hit record, the breakthrough product launch, is almost always the result of years of showing up when nothing was happening. As Thomas Edison put it: "Opportunity is missed by most people because it is dressed in overalls and looks like work."
The Sitcom Would Have Been Forgotten
Roberts and Rosenman never made their TV show. I think it's safe to say they're at peace with that.
What they made instead, by staying curious, by staying flexible, by saying yes to the people even when they said no to the idea, and by making the right call when the fences had to come down, became one of the defining cultural events of the 20th century.
Your opportunity probably won't involve 400,000 people and three days of rain. But the principles that led to Woodstock? Those are available to every entrepreneur willing to pay attention.
• Put yourself in the path of opportunity, even when you can't see what's coming.
• Look through the bad idea for the real potential underneath.
• When constraints force a choice, protect the product.
• Show up. Stay in the game. Be there when the moment arrives.
The sitcom was the setup. The festival was the opportunity. What's your NYT ad?
Alan McKee is the founder of The Amplified Entrepreneur and the author of The Amplified Entrepreneur: Building a Business That Rocks, an Amazon #1 Hot New Release in Business Education. He helps professionals over 50 transition from corporate careers to entrepreneurship, using the stories of classic rock legends to make the principles stick. Learn more at AmpMyBiz.com.
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