This story was first featured in our newsletter Speakers Stories, where every month we share one of the best failure stories from our global community. Be the first to receive these stories in your inbox—  subscribe to our newsletter here.

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Who?

Leo is a European entrepreneur and consultant who embarked on an unexpected journey to lose ego, money and some ingrained habits. With 17 years of business experience at México, Leo is a mix of "European discipline and Mexican creativity". His motto in life is "the shit is the caviar," because he deeply believes that difficult experiences are the ones that truly enrich us.

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Defining failure

FuN: What's your personal definition of failure?

Leo: For me, failure is like caviar: an acquired taste you learn to enjoy over time. Honestly, I love "screwing up" because every failure carries a lesson that no easy success could ever teach.

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FuN: What was everything like before the failure?

Leo: When I first came to México, I felt invincible, with a rather egotistical attitude. I thought I was smarter and better than the average person around me. I felt unstoppable, as if the world was mine to conquer.

Afterstarting a fishing tourism project, I began renting airplanes to fly from the island of Cozumel to the archaeological site of Chichen Itza, and the business grew so fast that I began to see the title of "millionaire" looming on the horizon. Some investors contacted me, among them one from Cozumel who joined the venture and with whom I was finally able to buy my first airplane.

‍Myego was so inflated that even the license plate had my name on it, just to annoy the competition and the authorities who had made it difficult for me to use the airport.Everything looked perfect...until the ego decided to teach me a lesson.

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The Real F*up 💩

Leo: I rented a permit from a large company in Toluca to do commercial flights, which also offered to select the pilots, insurance, etc. I was 100% confident in this process.

‍After two months, we conducted our first flight with a client from Cancún to Cozumel. I didn't know the pilot.

When we tried to land, the whole plane started to shake. The landing was what is called a "hard landing". The first bump was VERY hard, scary and was followed by several hard hits. The plane landed like a rabbit jumps. It hit the runway, went up into the sky, hit the runway, went up into the sky. As my head hit the seat I thought we were going to die, that the tail of the plane had shattered.

‍Whenwe got out of the plane we checked to make sure we were all right. Despite the loud bang that was heard, the tail was not broken, only one propeller was bent, however, the damage was 130,000 USD.

By law, the pilot had to have at least 150 hours of flight time, but in order for the insurance to cover the damage, 500 hours of flight time in that specific type of aircraft were required. He didn't have them. I remember sitting in the tail of the plane, sweating like never before in my life, without a penny in my account.

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FuN:Were there any red flags or warning signs beforehand?

Leo: We contracted with the company to rent the permit for USD 245, then it went up to USD 616 and before flying to USD 1,110. As partners we believed they were reliable and the best in the country.

‍Weshould have listened to our intuition, sat down with them, had a coffee and asked what is going on? Also, they never gave us the details of the pilot they hired for the flights. I didn't know him and trusted him completely.

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FuN: How did you realize the mistake?

Leo: Even though I hit my head and my nose was bleeding, I tried to stay positive. With my limited aviation experience, I thought, "We'll fix this in a day."

That same day, the employees of the commercial permit company helped us with the accident paperwork and told us that the repairs would take at least six weeks. Even though the shock had not sunk in, all I could think about was the damage (and the money) and the lack of income, because the plane would not be able to fly.

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That's when it hit me: my dream of becoming a "millionaire in aviation" had shattered completely.

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‍May day, may day....

‍Experiences like Leo's transform how we perceive failure, success, and our ego.

At Fuckup Nights for Companies, we believe in the power of storytelling to inspire and share valuable lessons through stories of failure.

‍Discover how in this link we can help shift the mindset of leaders and entire teams with customized solutions tailored to your organizational culture or team-building needs.

‍Back to Leo...

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FuN: How did you feel at that moment?

Leo: I cried in front of my client and my business partner. I remember we parked the plane, and I sat on the tail, staring at the disaster. It felt like I was in a movie—completely unreal. I kept thinking about how all that hard work had led to this.

I felt like a failure, imagining what the authorities and the competition must be thinking about me.

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Sharing the Failure

FuN: How did the people involved react?

Leo: The client said, "Wow, what an experience! How often do you survive a plane crash?" He took it surprisingly well—he didn't ask for a refund or anything else. He said, "I'm in Cozumel, that was the plan, and here I am."

I got lucky because 99% of clients would have sued, demanded a refund, or left scathing reviews. But I think the adrenaline made the experience seem positive for him.

As for the competition, they couldn't contain their laughter. "The rebel has learned his lesson," they said. People close to me didn't hold back either, coming at me with "I told you so" attitudes. Of course, they couldn't resist saying it out loud while I was still trying to piece together the remains of my shattered ego. These failures didn't just transform me—they reshaped how others perceived me.

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FuN: How was the issue resolved?

Leo: The same day of the accident, some employees of the permit company arrived by private plane with two lawyers and instructions on what to say or not to say, they had to settle with the airport. They managed to qualify the accident as just an "incident" so that it fell into another category.

My business partner invested additional resources, and we used our cash flow to buy parts for the plane. I didn't take a salary for months to cover the cost of the damage.

It took us four months to repair the plane. During that time, I partnered with a larger aviation company that owned two compliant aircraft we could rent. I personally vetted and selected experienced pilots for future flights.

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FuN: Would you do anything differently?

Leo: Honestly, I wouldn't change a thing. I'm at peace with who I am now, thanks to all the times I've "messed up." Those failures have brought me to where I am today, and without them, I wouldn't be able to help others as effectively as I do now. 

That failure forced me to take aviation seriously and do things correctly. In most businesses, you can experiment and see what works. But in aviation—or any field involving human or animal lives—you simply can't take such risks.

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

Leo: I still "fail" today because, at the end of the day, I'm still that kid with boundless energy and drive to grow. What's changed is that thanks to those mistakes, I can now offer incredibly valuable advice to CEOs and companies—not from textbooks but from the lessons life itself has taught me.

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In conclusion...

• A wise 80-year-old once told me: "That's a bargain, kid. $130,000 for a lesson worth a million."
• Trust, but double-check.
• Do things "by the book" when lives are at stake.
• If you're a beginner, learn from the pros.
• If you're a pro, never forget you were once a beginner—and help others.
• Clarity is power. Nothing is more powerful than knowing exactly what you want and where you're headed.

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Connect with Leo!

Remember, our channels are open for questions, complaints, feedback or collaborations at: rich@fuckupnights.com.

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