Woodstock was no less than a flower - power startup

What can we learn from the Woodstock Festival about entrepreneurship, leadership, management, communication, community building, problem solving and creativity in today’s disruptive world?

Nili Goldfein
6 min readDec 15, 2021

By Nili Goldfein and Ronen Gafni

Once upon a time in 1969, Michael Lang and Artie Kornfield — two enthusiastic young entrepreneurs from New York, reached out to Media Sound founders and producers Joel Rosenman and John Roberts, with a business proposal.” Let’s open another Media Sound branch in New York and launch it in a classy cocktail with the best singers in the region”, they offered. “Why stop at a cocktail?” the producers suggested, “let’s go big”. That was the beginning of Woodstock Ventures.

Six months and a roller-coaster production later, they launched Woodstock — the most significant music festival in history. The original business plan to sell 50,000 tickets resulted in a mega-audience of nearly 500,000, and a profound impact not only on music and the 60s generation, but also on western civilization at whole.

Fifty-something years later, it’s fascinating to realize how a small business venture that began as sales strategy for a recording studio transformed into a multigeneration cultural phenomenon. What can we learn from Woodstock about entrepreneurship, leadership, management, communication, community building, problem solving and creativity in today’s disruptive world? Turns out a lot.

Crucial executive decisions

The Woodstock Festival production evolved exactly like a startup: a disruptive product that challenged the conservative traditional market, continued to evolve, and gradually created a new dominant category of its own. But like all startups, there were numerous setbacks on the way that required crucial executive decisions.

Like any startup, the first step was raising capital and forming a team of production experts to carefully plan the festival, starting with finding a location, setting foundations for water, food, sanitation, and medical infrastructures and then execute the go-to-market strategy.

The original plan was to hold the festival in Woodstock, upstate New York, for an audience of 50,000. But then problems began to surface. Woodstock turned out to be too small for the event. Searching for a better solution, they checked out Walkill, another town which was large enough but lacked character and magic. The producers were discouraged by the gap between what they envisioned and what Walkill had to offer but decided to make the necessary compromise.

Five weeks before the festival, Walkill bailed out on their signed contract with Woodstock Ventures. Fearing that 50,000 hippies would destroy their conservative town, they quickly passed a by-law that prohibits gatherings of more than 5,000 people and blew the deal.

Losing their strategic partner resulted in half a million dollars and weeks of work going down the drain. But as tens of thousands of tickets had already been sold, the producers decided it was too late to back down, and they sent helicopters up in the air in search of a new location.

After a week of searching, they came across a property in Bethel owned by a farmer named Max. It was the perfect location: a natural amphitheater with magical vibes. The disappointing disruption of the Walkill episode and the entrepreneurs’ determination to not give up, turned out to be a blessing in disguise.

The Fence or Stage Dilemma

Changing the location was not easy; especially in terms of the logistics procedures needed to notify tens of thousands of ticket buyers back in 1969, decades before the internet and social media. But that was merely the tip of the iceberg.

The larger problem was that the remaining four weeks were simply not enough to build the festival grounds on time and according to plan. Days before launching, thousands of people were already camping on the premises, and nothing was ready.

The producers had to make an executive decision on what to give up: fences or stage? Giving up fences meant that anyone could enter the compound, and the festival would lose its economic potential. Giving up the stage meant disappointing the customers and draining the festivity out of the festival.

Not a simple decision. Differently from today’s startups that build on millions of users and can afford to lose money in its early stages, Woodstock Ventures had no exit horizon or marketing move that could generate future profit. It was either going back on their promise to the customers for a three-day magical experience of music, peace and love, or keeping their promise, compromising their business model, and losing millions of dollars. Bravely, or naïvely, they took a risk, prioritized their customers and gave up the fences.

Looking back, it was the right decision, yet far from popular. To date, there are numerous examples of startups and corporates who choose fences over stages, promote hollow bottom-line based business models, and compromise the quality of their product at their customers’ expense.

Communication and Community Building

Whether because of the producers’ young spirit, the 60’s vibe or the festival’s unique nature, Woodstock is an inspiring model for creative problem solving, especially in serious challenges like the festival’s security operations.

While most music festivals in the 60’s triggered violent incidents between security forces and festival participants, Woodstock found a creative Woodstock-style reversestrategy solution. They founded a security division consisting of several hundreds of commune members, led by a funny guy known as Wavy Gravy. Contrary to Police Force, they went music and good vibes. Realizing that the Please Force members looked like them and talked like them, the crowds responded in compliance, harmony and understanding, above and beyond expectations. That’s how emotional intelligence and creative thinking contributed to a safe and festive event.

Today all organizations realize the importance of building a strong community, where stake holders transform to committed friends who pursue shared goals, where mistakes are seen as milestones for innovation. In that sense, Woodstock was a threeday pop-up, versatile, supportive, and connected community. A school for community building, no less. Their genius strategy was in their simplicity: with hardly any money and with use of a mike, a stage and simple authentic communication, they engaged nearly half a million people who were fully committed to the success of their project. Simple as that.

Then and Now

In today’s sea of strategies, technologies, and extravagant campaigns, we sometimes forget that the most accessible tool is authentic communication. In a world of fake news, lies and manipulations, simple truth shines far and wide. As in 1969, this concept stands true today.

In today’s disruptive world, business leaders should agree to make brave decisions, engage partners and customers, and keep moving forward, even when the return on investment isn’t guaranteed. Woodstock is living proof that by believing in an idea, not compromising quality, and adopting creative thinking and honest communication, anyone can turn a small sales strategy venture into a phenomenon that impacts the world.

Nili Goldfein - EVP Marketing & Business Development at NGG Global Consulting Solutions, specializing in Leadership and Management in a World of Disruption.

Ronen Gafni - Business Philosopher, Game Creator, TEDx speaker, CEO at FreshBiz and Author of ‘The New Entrepreneurz’



Nili Goldfein

Nili Goldfein is EVP Business Development & Marketing for NGG Global Consulting. With over 30 years in the field she is creating and running global business.