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"I can tell you the EXACT moment when I destroyed my company": Lessons Learned from Leon Winkler's Failure

In an exclusive story for Fuckup Nights, Leon Winkler shares the reasons why his first company collapsed at the height of his career.

By:
Ricardo Guerrero
September 24, 2024
The rise and fall of Urban Entertainment

Leon Winkler Senior Director of International Events at Ubisoft tells his story of failure. We bring you an insightful (and hard) lesson told at one of our private Fuckup Nights events for companies. A lesson about success, fame and, most importantly, humility in young entrepreneurs told by our speakers themselves.

Leon leads a team responsible for some of the biggest events in the video game industry, such as Ubisoft Forward. He also launched the Black Game Pros initiative, dedicated to promoting representation and diversity within the industry.

Defining failure

FuN: What's your personal definition of failure?

Leon: To me, failure is not failing a goal or making mistakes; it's about not trying and not growing. True failure is giving up, not learning from experiences and not challenging yourself to improve. It is staying stuck, avoiding risks and letting fear of the unknown control your actions. Failure is a mindset that can be overcome with resilience, adaptability and the determination to keep moving forward, regardless of setbacks.

The Real F*up 💩

Leon: Between my late teens and early twenties, my brother and I embarked on a journey that began by producing hip-hop parties all over Holland. Our passion for the culture and our desire to bring it to a wider audience led us to propose a TV show based on our experiences to The Box, then part of MTV Networks.

Despite our lack of experience as TV show producers, the executives saw something in our proposal and decided to give us a chance. This opportunity resulted in three seasons of our show, which quickly gained fame within the hip-hop and R&B culture in the Netherlands.

However, I was young, and fame went to my head. We started attending business meetings with an entourage, often acting like a bunch of idiots. This was far from professional and definitely not a recipe for success.

Our main sponsors, who were initially enthusiastic about our program, became disillusioned with our unprofessional behavior and decided to cut ties with us. Despite being one of the most watched television programs at the time, our channel decided not to renew our contract. They "borrowed" our format and tried to produce the program themselves, but their attempt was unsuccessful.

FuN: What were the key decisions that led to the failure?

Leon: I can tell you the EXACT moment I destroyed my company. We were about to sign a deal with a major concert promoter, and our first collaboration involved covering a huge multi-artist hip-hop concert at the Amsterdam Arena.

However, in my youthful arrogance and lack of professionalism, I did not fully understand the magnitude of the situation. Instead of hiring our regular, reliable cameraman, I decided to bring an old friend who wanted to attend the concert. What I didn't consider was that our agreement with the promoter was not yet officially signed, and there were strict rules for this event. One crucial rule was: NO RECORDING THE STAGE OR THE PERFORMANCES.

I left my friend on his camera roll. Everything seemed to be going well until, out of the corner of my eye, I saw him standing in front of the stage, surrounded by security. He had done the one thing we had been explicitly told not to do: he pointed the camera at the stage.

I ran to him, hoping to calm the situation, but it quickly escalated. The security team took us backstage to meet with the event's core team and concert promoters. They had been watching us the whole time, and my friend's mistake put us on their radar for all the wrong reasons.

They literally carried us out of the venue, escorting us through the crowd in a scene that was as humbling as it was sobering. That moment was a hard lesson in humility and the importance of professionalism.

On short-term objectives

Leon: HA! When my brother and I started Urban Entertainment, our initial goals and expectations were a mix of youthful ambition and a certain naiveté. We dreamed of buying white Lexus cars and amassing significant wealth, fueled by the success of our TV show.

Our vision was grandiose, driven by a passion for hip-hop culture and a desire to make a mark in the entertainment industry. However, in reality, we had almost no business experience.

We saw our television program as a springboard, a platform that would catapult us into greater opportunities.

Our lack of experience meant we were learning everything as we went along, often making decisions based on intuition rather than informed strategy. It was almost comical how little we knew about running a business and producing a television show. However, this inexperience didn't stop us. Our passion and determination drove us forward, propelling us into a world we barely understood but were eager to conquer.

FuNCan you identify any warning signs that they may have missed?

Leon: We believed too much in our own fame and failed to recognize the importance of maintaining professional conduct and relationships. Our behavior in business meetings should have been a clear indication that we were not handling things properly.

Furthermore, we ignored the need to build strong and respectful relationships with our sponsors and partners. We took their support for granted, assuming that our success would sustain us.

FuN: How did this failure help your personal and professional growth?

LeonThe fall of Urban Entertainment was a humbling and transformative experience for me. It forced me to face my own limitations and recognize the importance of maturity and professionalism in achieving long-term success. This self-understanding has been invaluable in my personal growth, helping me develop better judgment and decision-making skills.

Professionally, this failure was a turning point that transformed my career path. It gave me a deep understanding of the complexities of the entertainment industry and the importance of strategic planning and execution.

This experience has been fundamental to my success at Ubisoft, where I have been able to leverage this knowledge to drive global event strategies and build strong, lasting relationships. The personal adversities I faced during that time also made me more empathetic and understanding as a leader, improving my ability to effectively support and motivate my team.

Sharing Failure

FuNWith whom did you share the experience, what was going on around you?

Leon: I shared the experience mainly with my close family and a few trusted friends. My brother, who was my business partner, was with me every step of the way. We faced the consequences together, which brought us closer together but also tested our relationship.

Explaining the situation to our sponsors, partners and team was exhausting. It was difficult to admit that we had failed, especially since much of it was due to our own unprofessional behavior and poor decisions.

The most difficult conversation was with the concert promoter after the incident at the Amsterdam Arena. Trying to explain and apologize while we knew we had blown a significant opportunity was incredibly humbling. There were also conversations with family and friends, admitting that we were not as invincible as we thought and facing their disappointment and concern. Each discussion felt like another layer of the reality of our sinking failure.

In conclusion...

  • Professionalism is paramount: Be reliable. Always deliver what is expected of you, maintaining a high standard of conduct in all business interactions. This builds trust and respect, which are essential for long-term success.
  • Remain humble and open your mind to feedback: Overconfidence can blind you to potential risks and areas for improvement. Ask yourself, how would you feel if your actions were on the front page of tomorrow's newspaper?
  • ‍Buildgenuine relationships: Be empathetic. Truly understand what your partners and sponsors want to achieve and why. Avoid being utilitarian and transactional. These relationships are the foundation of a successful business.
  • Think big and execute small: Passion and drive are important to set direction, but they must be accompanied by diligent execution and attention to detail. Learn to enjoy the daily grind, your craft.‍
  • Adapt and change course: Failure is not the end. Use it as an opportunity to learn, grow and find new paths forward.‍
  • Know yourself: Personal and professional challenges, including difficult times with your mental health, can teach invaluable lessons in resilience and empathy.‍
  • Consistency and authenticity: Consistent actions and decisions, based on authenticity, build credibility and trust. Being true to yourself and your values fosters genuine connections and long-term success.

Connect with Leon!


Remember that our channels are open for your doubts, complaints, feedback or collaborations with: rich@fuckupnights.com

Edited by

"I can tell you the EXACT moment when I destroyed my company": Lessons Learned from Leon Winkler's Failure
Ricardo Guerrero
Media Editor & Newsletter Coordinator
Content & typos creator. He probably posted this blog by himself, and thinks it's awkward to write his own bio. Fuckuppin's mom.
funfunfunfun

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