5 Key Lessons Entrepreneurs Can Learn From Woodstock
August 15th marked the anniversary of the beginning of the most legendary music festival of all time—the Woodstock Music & Arts Fair, which took place in 1969. A second Woodstock festival was held in 1994 to commemorate the 25th anniversary of the original and a third festival, the subject of a 3-part Netflix documentary series entitled “Trainwreck: Woodstock ‘99”, was held in July 1999.
I had the pleasure of getting to know Woodstock’s creator, Michael Lang, who tragically passed away earlier this year. Michael was a visionary and an eternal optimist, everything you would expect the creator of Woodstock to be. His presence was always calming, and you could feel his genuine love of people and life.
As a musician and fan, I confess that I am somewhat obsessed with the 1969 Woodstock music festival. For me, and for many others like me, it represents a perfect moment in time—a moment of unbridled free expression, when the ideals of a generation became reality, and love conquered all. From an outsider’s perspective at the time, however, it was a complete disaster doomed from the very start.
First, there was the location. The site of the original Woodstock—the now famous Yasgur’s Farm—was far from Michael’s original pick. In fact, it was his third, and a last-minute Hail Mary with only weeks to go before the festival was supposed to go on. Michael originally wanted the festival to take place at what he told me was the “ideal” location—Winston Farm in Saugerties, New York. However, after a promising start to negotiations, the owners ultimately decided to not lease the property to Michael and his partners. By the time the decision was reached, plans were already underway for the festival (now less than 5 months away) and several bands were already booked. Michael ultimately got to see his original vision at Winston Farm come to life in 1994, as the historic 800-acre farm served as the location for Woodstock ’94. For better or worse, Winston Farm was sold in 2020 to a group of investors who are proposing to transform the site into a $600-mllion mixed-use destination venue that would include a 10,000-seat amphitheater, adventure park, multi-unit housing, technology park, campgrounds, and hiking trails.
With Winston Farm no longer a possibility and options running out, Michael settled on a 300-acre industrial park in the town of Wallkill, New York. Despite being approved, relations with the town deteriorated and a new ordinance was passed forcing the Woodstock team to apply for another permit. With only month to go to the festival, the town zoning board rejected Michael’s permit application on July 15, 1969. It was this setback that led to a desperate search for another property and the serendipitous discovery of Yasgur’s Farm. The rest, as they say, is history.
After finding the location, the challenges continued to mount. There was not enough time to complete construction of the new site, the concert would eventually become free to all (an inevitable financial disaster), supplies would run short and, of course, there was the weather. All of this is documented in Michael’s book, “The Road to Woodstock,” which I picked up after meeting Michael for the first time. I expected a peak backstage and to learn about Michael’s encounters with the many now legendary performers like Jimi Hendrix, Janis Joplin, the Grateful Dead, Ritchie Havens, Santana, Crosby, Stills and Nash, the Who, etc. To my surprise, the book was more an incite into the mind of a visionary entrepreneur, the launch of his startup and the creation of an iconic brand. I encourage every business owner to read it.
Woodstock has remained culturally relevant for over 50 years. I have seen the movies and documentaries, read the books and spent time getting to know the wonderful human behind it all. Here are five key lessons I have learned about business and being an entrepreneur from Woodstock and its founder, Michael Lang.
1. Where There is a Will, There is a Way.
Nothing was going to stop the Woodstock Music and Art Fair from happening in 1969. Nothing. Despite everything that could have gone wrong going wrong, Michael pressed forward and made it happen. As he recalls in Road to Woodstock, when it was his turn to speak to the Wallkill zoning board about a permit only a month before the festival’s announced dates, Michael said: “We’ve already put more than five hundred thousand into this project…We cannot get that money back. We are moving forward with this festival…We are totally committed to the event, to the plans, and to the site.” Nothing was going to stop Michael at this point. Nothing. In life, as in business, your will power is a choice. Michael had made up his mind and his will was invincible. This is the mentality you have to have as an entrepreneur. If you want to succeed, you must exercise control over the one thing you actually control—yourself. If you allow yourself to be defeated, then you will be. Nobody can make you quit except, of course, you.
2. Ready, Shoot, Aim.
I am sure he did not coin the phrase, but Michael Lang was the first person I ever heard say, “ready, shoot, aim.” He was talking about the mentality of a startup and being an entrepreneur. Aiming is about precision. It is calculated and time consuming. Like many entrepreneurs, Michael relied heavily on intuition and instinct. When you have a vision, rarely is there the information needed to calculate precise execution of that vision. If you are waiting for precision, then you will never get started.
3. Authenticity is Everything.
I was introduced to Michael Lang by a mutual acquaintance. Randomly, I mentioned an idea I had for a not-for-profit that was inspired by the spirit of Woodstock and she said, “I know Michael Lang and will introduce you.” As I walked towards our lunch destination in the Theater District of New York, I remember thinking that meeting Michael would either be everything I expected or a complete disappointment. Like with almost any public figure, you never know who the real person is until you meet them in person. Michael turned out to be the real deal, completely genuine and sincere. He was authentic. I would like to think he saw the same in me, and that was the basis for our immediate connection and trust.
Leadership requires authenticity. Nobody will follow you into battle if they think you do not genuinely believe in your cause or fight. Woodstock ’69 was made possible by the countless number of people working tirelessly to make it happen against all odds. Their commitment was fueled by their belief in their fearless, and unwaveringly calm, leader—Michael Lang. I have no doubt that Michael’s authenticity was the foundation for those workers’ trust and belief in him.
The same is true of the lasting success of Woodstock ’69. The original festival was built on the ideals of peace and love, which were authentically embedded in the brand and festival. Flash forward to 1999, in which a brand built on peace and love was being used for the sole purpose of making a profit. It was disingenuous from the start and fans knew it. The result was a disaster.
4. Free is Not Fair; Fair is Fair.
My original idea for a not-for-profit involved putting on a large music festival similar to Woodstock that would be free to the public. When I told Michael I wanted to put on a free concert, he quickly remarked, “Free is not fair. Fair is Fair.” Michael believed strongly in fair exchange. Over time, I understood this to be a life truth more than simply an economic truth. The universe requires balance—what you receive in life is equal to what you give in life. Physics teaches us that “for every action there is an equal and opposite reaction” (Newton’s third law of motion). Paul McCartney sang, “And in the end, the love you take is equal to the love you make.” Why shouldn’t the same be true in the marketplace?
People want to be treated fairly. One of the major problems with Woodstock ’99 was that the audience ultimately felt ripped off. Everything was expensive, from ticket prices to bottled water. Yet, the facilities were anything but luxurious or state of the art. Because of budget cuts made to increase profits, waste management and sanitation was poorly managed, leading to unlivable conditions. Attendees felt like they gave more than they were getting, and this frustration ultimately boiled over into the chaos that ensued.
5. You Cannot Manufacture a Movement.
The original Woodstock was built upon a radical movement referred to as the counterculture. While many think of the fashion associated with the 60’s, the movement was actually much deeper. This was a generation born into a different world, a world in which the United States had forever changed history by dropping the atomic bomb. By 1969, the United States was entrenched in the Vietnam War, a war which many thought was senseless. The country had just endured the violent civil rights movement, as well as the assassinations of John F. Kennedy, Robert F. Kennedy and Martin Luther King, Jr. These events gave rise to a new consciousness that wanted to be governed by the ideals of peace and love. Woodstock became the opportunity to show that those ideals in fact could work, and they did.
When I spoke to Michael about wanting to recreate the “spirit” of Woodstock, he explained that it was something you could not just manufacture. The spirit of Woodstock already existed in the collective consciousness of the counterculture movement—Woodstock simply gave it a home, a destination and proving grounds.
You cannot manufacture spirit, you can only gather it together and give it a place to flourish.
In Trainwreck, Michael explains how they tried to find a cause to cling to for Woodstock ‘99. At the time, gun violence was becoming a major issue in America and the mass shooting at Columbine High School had occurred only a few months earlier. The country was hurting, for sure, and the organizers felt that perhaps this would be the central issue around which the audience could rally. Unfortunately, the opposite was true. The collective consciousness that arrived for Woodstock ’99 was angst fueled, driven by such hard core and heavy metal acts as Korn, Limp Bizkit and Rage Against the Machine. The response of this crowd to the increased violence in America was not peace, but more violence. When Michael had the beautiful idea of a mass candlelight vigil to end the festival, those candles were used to torch what remained of the festival grounds. The truth is that money was the motivating factor behind Woodstock '99, not any social cause. When the organizers tried to manufacture a cause, they failed miserably. You cannot manufacture spirit, you can only gather it together and give it a place to flourish.
