The Senior Director of International Events at Ubisoft reflects on his experience, the lessons learned, and how they shaped his career.
In the world of entertainment, success can often be fleeting. Leon Winkler, a seasoned professional with over 20 years of experience, knows this all too well. His journey began in his late teens, producing hip-hop parties in the Netherlands, eventually leading to the creation of a TV show, "Urban LifeStyle." However, the success of Urban Entertainment was short-lived, culminating in a painful collapse. In this interview, Leon reflects on his experiences, the lessons learned, and how they shaped his career.
FuN: What is your personal definition of failure?
Leon: That’s a good question! For me, failure isn't about missing a target 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's about staying stuck, avoiding risks, and letting fear of the unknown control your actions. Failure is a mindset that can be conquered with resilience, adaptability, and the determination to keep pushing forward, regardless of setbacks.
FuN: Can you share a brief overview of the project/initiative you worked on that ultimately failed?
Leon: One notable example is the inevitable demise of my TV production company, Urban Entertainment. In my late teens and early twenties, my brother and I embarked on a journey that began with producing hip-hop parties throughout the Netherlands. Our passion for the culture and our desire to bring it to a broader audience led us to pitch a TV show based on our experiences to The Box, which was 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 shot. This chance resulted in three seasons of our show, which quickly gained fame within the hip-hop and R&B culture in the Netherlands.
FuN: What were the company/you/your team’s initial goals and expectations for this project/initiative?
Leon: Lol! When my brother and I started Urban Entertainment, our initial goals and expectations were a blend of youthful ambition and naïveté. 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—perhaps a combined total of 0.1%. Our journey began purely out of enthusiasm and a deep connection to the culture we were representing.
FuN: Can you describe the market conditions and industry trends the company was operating in during this project’s/initiative’s failure?
Leon: The early 2000s was a unique time for media and entertainment, a period that existed just before the explosion of social media, YouTube, and affordable editing software. Back then, the tools and platforms we take for granted today were either prohibitively expensive or simply didn't exist. Editing software was not only costly but required high-end computers, which could set you back around $10,000—a significant barrier to entry for young, aspiring producers like my brother and me.
During these pre-digital, pre-social media days, the landscape for Urban music was rapidly evolving. There was a noticeable surge in the popularity of Urban music genres, yet there were very few platforms dedicated to promoting and showcasing this emerging trend. As someone deeply embedded in the culture, I was DJ-ing and producing parties across the Netherlands, witnessing firsthand the growing demand for Urban music. Despite its rising popularity, mainstream media was slow to provide a platform for this genre, creating a significant gap in the market.
The market conditions were challenging. Traditional media was still dominant, and breaking into TV without significant financial backing or industry connections was incredibly tough. Moreover, the lack of affordable technology meant that our production costs were high, and we had to rely on external funding and sponsorships to keep the show running. Our inexperience in handling these aspects became a critical factor in the eventual downfall of Urban LifeStyle.
In conclusion, the early 2000s presented a unique set of challenges and opportunities. While the market conditions were ripe for innovative Urban content, the lack of accessible technology and our own missteps ultimately led to the project's failure. However, this experience laid the groundwork for my future endeavors, providing crucial insights into the interplay between passion, professionalism, and market dynamics.
FuN: Did the company's financial performance contribute to this eventual failure? If so, how?
Leon: Yes, the company's financial performance significantly contributed to the eventual failure of Urban Entertainment. The incident at the Amsterdam Arena was a major turning point. After we were “blackballed” by the concert promoter and word spread about our unprofessional behavior, it became increasingly difficult to secure sponsorships and partnerships.
Our reputation took a severe hit, and as a result, our revenue streams dried up. Sponsors who were once enthusiastic about our show withdrew their support, leaving us without the necessary funds to continue production. The financial strain became insurmountable. Without sponsorships and new deals, we couldn't cover our operational costs or invest in necessary resources.
Adding to our challenges, The Box decided not to prolong our contract after the incident. This decision was another significant blow, as it cut off a critical platform for our content and eliminated a major source of income. The lack of financial stability ultimately led to the company's bankruptcy. We had relied heavily on external funding to produce our show, and once that was gone, we had no cushion to fall back on. The combination of damaged relationships within the industry, the loss of our contract with The Box, and the sudden financial void proved to be too much for us to overcome. In the end, it was our inability to maintain financial performance and secure ongoing support that sealed the fate of Urban Entertainment.
FuN: Could you identify any warning signs or red flags overlooked or disregarded by the company's/team’s management/leadership?
Leon: I was the company manager and part of the leadership, so the responsibility falls squarely on my shoulders. The biggest red flag was our complete lack of professionalism and experience in running an entertainment business at the level we were operating. We were young and naive, believing that our popularity as one of the most-watched shows on the channel guaranteed our success and contract renewal.
This overconfidence was a major red flag. We believed too much in our own hype and failed to recognize the importance of maintaining professional conduct and relationships. Our behavior at business meetings, where we showed up with an entourage and acting like a bunch of idiots, should have been a clear indicator that we were not handling things appropriately.
Additionally, we ignored the necessity of building solid, respectful relationships with our sponsors and partners. We took their support for granted, assuming our success would carry us through. The reality, however, was starkly different. Our lack of professionalism and disregard for the business side of the entertainment industry ultimately led to our downfall. We failed to heed these warning signs, and it cost us dearly.
FuN: How did the company's/team’s management/leadership and organizational culture influence the initiative/project failure?
Leon: The end of our company was directly influenced by our management and organizational culture. When our contract was not prolonged, it was almost overnight that all the people we thought had our back and best interests at heart vanished. Every single person disappeared, leaving us isolated and unsupported.
This sudden exodus highlighted the fragility of the relationships we had built. Our management approach, characterized by a lack of professionalism and over reliance on our popularity, created a culture where people were more interested in our success than in genuinely supporting us. When things started to fall apart, there was no loyalty or commitment from those around us.
This experience was one of the most sad and sobering moments of my career. It taught me the harsh reality that a strong, professional organizational culture and solid, genuine relationships are crucial for long-term success. Our failure to foster this within our team and network was a significant factor in our downfall.
FuN: What were the key strategic decisions made by the company, you, and your team that may have led to the downfall of the project/initiative?
Leon: I can tell you the EXACT moment I caused the death of my company—it's a story that still makes me cringe and laugh at the same time. We were on the brink of signing a deal with a huge concert promoter, and our first collaboration involved covering a massive multi-artist hip-hop concert at the Amsterdam Arena. This was a golden opportunity that could have catapulted Urban LifeStyle to new heights.
However, in my youthful arrogance and lack of professionalism, I didn't fully grasp the gravity of the situation. Instead of hiring our regular, reliable camera guy, I decided to bring along an old friend who wanted to attend the concert. I mean, how difficult could it be to hold a camera and get some good shots, right? That was my first major mistake—underestimating the importance of experienced, professional crew members for such a high-stakes event.
What I neglected to consider was that our deal with the promoter wasn't officially signed yet, and there were strict rules in place for this event. One critical rule was: DO NOT SHOOT THE STAGE OR ANY PERFORMANCES. This seemed simple enough, but my lack of foresight set us up for disaster.
When we arrived at the venue, I was immediately recognized and got swept up in the excitement, posing for pictures and enjoying my fleeting celebrity status. Meanwhile, I left my friend to his own devices with the camera. Everything seemed to be going well until, from the corner of my eye, I saw him standing in front of the stage, surrounded by security. He had done the one thing we were explicitly told not to do—pointed the camera at the stage.
I rushed over, hoping to defuse the situation, but it quickly escalated. The security team led us backstage to meet the core event team of the concert promoter. They had been watching us the entire time, and my friend's mistake had put us on their radar for all the wrong reasons. They demanded the tape, which we handed over, still not fully grasping the seriousness of the breach. Feeling quite nonchalant, I thought we could smooth things over.
Instead, we got the "Fresh Prince of Bel-Air" Jazzy Jeff treatment. We were literally picked up and thrown out of the venue, escorted through the crowd in a scene that was both humiliating and sobering. That moment was a brutal lesson in humility and the importance of professionalism.
FuN: Did you share the learnings with other teams in your organization? If so, how? What was the reaction of the different people involved?
Leon: I never really used my experience with Urban Entertainment as a case study during meetings. Instead, the learnings from this failure have profoundly influenced my management style, making me into a more compassionate and effective leader. While it’s not a story I bring up frequently in a formal setting, the lessons I've learned are deeply embedded in how I approach leadership and team dynamics.
In various conversations and informal settings, I’ve shared bits of my journey, including my setbacks, to illustrate the importance of professionalism, strategic planning, and humility. I’ve also spoken about my come-up story many times, including in a TEDx talk, where I strive to be an open book, sharing both successes and failures to provide a comprehensive view of my journey.
The reaction from those who hear my story has been overwhelmingly positive. People appreciate the candidness and practical insights drawn from real-life experiences. This openness helps build a culture of continuous learning and improvement within the organization. It demonstrates that failure is not the end but rather a stepping stone to greater achievements. The lessons from my past have equipped me to better support and guide my team, fostering a work environment where professionalism, humility, and resilience are valued.
FuN: How can your story help other managers/leaders/entrepreneurs?
Leon: My key learnings from this experience are:
Applying our Failure Management methodology, we detected that the following errors were determinant in the failure of the project and the antidotes that serve as lessons learned to avoid similar situations that lead to failures and preventable errors in the future.
By implementing these actions, leaders can create a more resilient and professional environment that minimizes the risk of repeating past mistakes.
Fuckup #1. Hiring Inexperienced Crew: Instead of bringing a professional camera operator, Leon chose an inexperienced friend, which led to critical errors during a high-stakes event.
Antidote: Hire Experienced Personnel
Fuckup #2. Underestimating Event Rules: Leon failed to fully grasp the importance of the event's rules, particularly the prohibition against shooting the stage, which resulted in a significant breach.
Antidote: Train team members to be adaptable and resilient in the face of challenges.
Fuckup #3.Lack of Supervision: There was inadequate supervision and communication regarding the critical rules of the event, showcasing immaturity and a lack of business acumen.
Antidote: Document Processes and Learnings
Fuckup #4. Overconfidence and Arrogance: The team exhibited overconfidence, believing their popularity would guarantee success, which blinded them to potential risks.
Antidote: Foster a Culture of Humility
Fuckup #5. Unprofessional Behavior: Their behavior at business meetings alienated sponsors and professional contacts.
Antidote: Prioritize Professionalism
Fuckup #6. Neglecting Relationships: They took their relationships with sponsors and partners for granted, failing to build strong, respectful connections.
Antidote: Build Strong Relationships
Fuckup #7. Ignoring Warning Signs: The team overlooked red flags regarding their lack of professionalism and experience in running an entertainment business.
Antidote: Encourage Open Communication and Learn from Failure
Fuckup #8. Lack of Adaptability: They did not adapt to the changing market conditions and missed the opportunity to transition to new platforms like YouTube, which emerged shortly after their show's cancellation.
Antidote: Encourage Resilience and Adaptability to Market Changes
Fuckup #9. Inadequate Financial Planning: The reliance on external funding without a solid financial strategy led to vulnerability when sponsorships dried up.
Antidote: Maintain Financial Oversight
Fuckup #10. Poor Crisis Management: After the incident at the Amsterdam Arena, they failed to manage the fallout effectively, leading to damaged relationships and loss of support.
Antidote: Implement Strategic Planning
Leon's journey is a testament to the resilience of the human spirit. His experiences serve as a reminder that while success can be intoxicating, it is the lessons learned from failure that truly shape us. As he continues to thrive in the entertainment industry, Leon remains committed to sharing his insights and inspiring others to approach their ventures with a balanced mix of passion, professionalism, and authenticity.
With over 20 years of experience, Leon is now the Senior Director of International Events at Ubisoft, leading a team responsible for some of the biggest events in the video game industry like Ubisoft Forward.
Additionally, he launched the Black Game Pros initiative, dedicated to promoting representation and diversity within the industry
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Editado por
Raquel Rojas
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