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The plane crash that cost me 130,000 USD

Leo shares his failure in Cozumel, a $130k plane crash that turned into a priceless lesson

By:
Fuckup Nights
November 22, 2024
Leo's Failure at Cozumel: A $130k Lesson

This story was first seen in our Speakers Stories newsletter, where each month we share one of the best failure stories from our global community. Get these stories in your inbox before anyone else, subscribe to our newsletter here.

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, 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.

Defining failure

FuN: What's your personal definition of failure?

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

FuNWhat was it 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.

After embarking on a fishing tourism project, I started renting airplanes to fly from the island of Cozumel to the archaeological site of Chichen Itza.

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.

My ego was so inflated that even the license plate had my name on it, just to annoy 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.

The Real F*up 💩

Leo: My new partner told me that his godfather had an aviation company near the capital and could rent us a commercial permit to fly. He also offered to select pilots, insurance, etc. I trusted him 100%.

‍Aftertwo months, we started our first flight with a client from Cancun to Cozumel. I did not know the pilot.

‍Whenwe tried to land, the whole plane began to shake. Suddenly over the runway there was a loud bang. 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.

The pilot did not even have 20 hours of flight time in that type of aircraft, when by law it must be 150, otherwise the insurance cannot cover the expenses.

I remember sitting in the tail end of the plane, sweating like never before in my life, without a penny in my account.

FuNWas there previously any network flag or warning signal?

Leo: We made a contract with my partner's company to rent the permit for 245 USD, then it went up to 616 and before flying to 1,110 USD. 

‍Mypartner convinced me by saying they were trustworthy and the best in the country. I should have sat down with them, had a coffee and asked what's going on? Also, the company never gave me the details of the pilot they hired for the flights. I did not know him and trusted him completely. 

FuNHow did you realize the error?

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, my partner's employees helped me with the accident paperwork and told me 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.

That's when I realized that the whole dream of being an "aviation millionaire" had been shattered.

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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.

Sharing 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 was lucky because 99% of clients would have sued, demanded money or left bad reviews. But I think the adrenaline rush was very positive.

The competition did not hold back and burst out laughing. "The rebel" had been taught his lesson. People close to me showed no mercy, with their "I told you so" attitude. Of course, they couldn't resist saying it out loud, as I tried to pick up the pieces of my broken ego. Those failures not only changed me, they also changed the way others saw me.

FuNHow was the problem solved?

Leo: The same day of the accident, some employees of my partner's company arrived by private plane with two lawyers and instructions on what to say and what 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 partner put in more resources and we bought parts of the plane with the cash flow we had. I did not receive a salary for months in order to pay for the damage.

It took us four months to repair the plane. In that time I found another larger aviation company that had two compliant aircraft that we were able to lease. I selected the right pilots with more experience myself.

FuNWould you do anything differently?

Leo: The truth is that I wouldn't change anything. I am completely at peace with who I am now, after being "wrong" so many times. Those downfalls are what got me this far, and without them I wouldn't be able to help others the way I do now. Of course, I am conscious of applying those lessons to each new adventure. 

This had to happen to take aviation seriously and do things right. You can do a business and see if it succeeds, but if it doesn't, nothing happens with your work. With aviation, on the other hand, the truth is that I took risks I shouldn't have. If you are in a business with lives of people or animals, you can't do this kind of thing.

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

Leo: I still "fail" today because, at the end of the day, I'm still that kid with endless energy and drive to grow. The interesting thing is that, from those mistakes, I can now give extremely valuable advice to CEOs and companies. Not based on college books, but on the lessons that life itself gave me.

In conclusion...

  • A wise man in his 80s said to me, "That's a bargain, boy. 130,000 is a million-dollar lesson."
  • You have to trust, but you have to double check.
  • Do things "by the book" if it is a business with lives involved.
  • If you are a beginner, look for the "pro" people to learn from.
  • If you are a "pro" person, never forget that you were a beginner and support others.
  • Clarity is power. There is nothing more powerful than knowing exactly what you want and where you are going.

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Connect with Leo!

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

Edited by

Ricardo Guerrero

The plane crash that cost me 130,000 USD
Leo Waltman
Business Consultant | 𝙎𝙩𝙖𝙣𝙙𝙤𝙪𝙩, 𝙨𝙚𝙡𝙛 𝙢𝙖𝙙𝙚 𝙚𝙣𝙩𝙧𝙚𝙥𝙧𝙚𝙣𝙚𝙪𝙧 𝙖𝙣𝙙 𝙞𝙣𝙫𝙚𝙨𝙩𝙤𝙧; 𝙫𝙞𝙨𝙤𝙣𝙖𝙞𝙧𝙚 𝙬𝙞𝙩𝙝 𝙖 𝙝𝙞𝙜𝙝𝙡𝙮 𝙞𝙣𝙨𝙥𝙞𝙧𝙞𝙣𝙜 𝙗𝙪𝙨𝙞𝙣𝙚𝙨𝙨 𝙨𝙩𝙤𝙧𝙮. 𝙎𝙋𝙀𝘼𝙆𝙀𝙍 𝘼𝙉𝘿 𝙈𝙀𝙉𝙉𝙏𝙊𝙍.
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, 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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