entrepreneurs skydiving

What can skydiving teach us about business? To jump? To be reckless? To have the “YOLO” mindset? I had never really thought about the parallels skydiving and entrepreneurship had in common until I spoke with Wilbert Wynnberg.

Wilbert Wynnberg is a serial entrepreneur (Founder & CEO of FTBT Academy & AuthorRise Media), awarding-winning author & founder of Think Act Prosper (TAP) Growth Conference, but he’s also a skydiving enthusiast. When talking with him, he speaks passionately both about scaling a range of businesses, and about his skydiving journey. 

Prior to him becoming a licensed skydiver (with more than 50 solo jumps under his belt), he had a fear of heights. I knew about his fear and so was curious to learn more about why he decided to skydive. More importantly, I wanted to know more about how he was able to conquer his fear, as I share the same fear of heights. 

I caught up with Wilbert over a cup of coffee to learn more. How does someone who would easily tremble with fear if he was on a high floor in a shopping mall manage to jump out of a plane? I could only imagine how far he has had to come, to not only overcome that fear of heights but, as he phrases it, “eventually come to love heights.”

His skydiving journey has taught him many lessons that spilled over into his businesses, and I believe that other entrepreneurs can learn from them too. 

Have a plan

I didn’t buy a ticket and fly straight to California to register for the first jump I could find. In fact, I spent quite a bit of time thinking and writing about the process of jumping before I even booked a day in the flight tunnel simulator. I wrote in a notebook about how I would tackle my fear, about what exactly I was afraid of, and how overcoming it might feel like. I wrote out my concerns and everything else that came to me. Seeing my fear on paper helped make it less scary, and having a plan made me feel more confident that I could overcome it. Only once I was confident about the plan, did I go ahead with it. Every time I felt a bit lost, I would refer to that notebook to remind myself of the plan. If anything on the paper was not working, I would tweak the plan until I found a way to overcome the obstacle, but I did not abandon the goal”, said Wilbert. 

No plan will work 100% perfectly. But if you at least have a plan, then you have a structure and can still move towards an end goal. As always – hope for the best but be prepared for the worst. That way things won’t take you by surprise and you can act accordingly instead of simply reacting.

Surround yourself with the right people

I still remember when I first decided on my plan to overcome my fear of heights, I started asking around for help. Around 90% of the people I spoke to told me not to do it. They said things like, “it’s too dangerous” and “are you sure you are ready for it?” It was already hard for me to even think about it, but I had gone to the wrong group of people for advice, and as a result I was even more scared.

I decided to talk with two friends who had done tandem skydiving before. They explained to me how beautiful the scenery was from above, how it felt, and how they would love to do it again. Then I was introduced to an experienced skydiver, Joel Aguirre, who eventually became my instructor and friend. He taught me everything I know; what to do under normal skydiving conditions and also what to do during emergencies. It was only after speaking with people who had already gone through the experience that I became really confident”.

Most of the time, we fear the unknown. But surrounding yourself with the right people, true practitioners and those who’ve experienced things first hand, they will provide you with the right kind of knowledge and skills to tackle any problem. The same is true for business. If you have a leadership crisis or money management issues, do you think it’s better to ask a fellow entrepreneur who has faced similar problems, or ask an employee of a business in a completely unrelated sector to you? Be sure to learn only from those who have proven themselves.

Continuous learning

Each jump is different from the last. There are always checks to be done and situations to learn from. And anytime you feel that you are not doing something right, you need to immediately check with your peers. In skydiving, your laziness of not asking can cost you your life. If you treat your business as seriously as you would your life, being sure to continuously learn, improve and upgrade, what do you think your success rate would be?”

Wilbert, like many other successful entrepreneurs, understands that there are two modes of operating. The first is standing still, also known as complacency. The second is growth, continuous learning and expanding what is possible. If you reach your goal, set a new one. If you are stuck in a rut, try different things. If you are building a business, every failure is a success because you can grow from the experience. Life should be about continuous learning.

Don’t overthink

Sometimes you just have to jump first and think later. Yes, you need to have a plan, but don’t let over-analysis become your paralysis. In skydiving, everything you have planned for can only be executed once you jump out of the plane. And everything you have planned for your business…… you have to jump first.” Wise words from a man with a fear of heights; jump first and think later.

Regardless of what you are trying to achieve, the key is to start moving. Get some momentum going by taking action. If Apple were to wait for the perfect product, they would have never been able to release the first iphone. So many years later, they are still ‘upgrading’ and making the product better, and the result is that they keep becoming more profitable. But upgrading is really just another way of saying ‘thank you for using our imperfect phones while we try to develop a perfect one’.

Have faith

If you would have asked me just before my first tunnel flight practice how many jumps I would go on to do, my answer would have been one. I didn’t know that I would fall crazily in love with my fear, and end up completing more than 50 jumps. I would have probably been too focused on trying to complete the tandem skydive, and wasn’t planning too much after that. But I remember having faith in myself that I could complete one jump, and pushed forward to completing that goal”, said Wilbert.

Most of the world’s biggest companies today didn’t know when they started how big they could become. Do you think Apple knew? Google? Microsoft? Maybe they knew they were going to be successful, but they probably didn’t expect their current levels of mega success. They were so focused on making their products a reality that they didn’t need to dream too much into the future. But the individuals who started the companies had faith they were following the right path. 

The key is to have faith in yourself and on the path you are walking in life. In skydiving, you need to have trust in your own knowledge, equipment, and abilities. The same can be said about running a company. Now, where do I sign up to jump?

About Wilbert Wynnberg

Wilbert is a Serial Entrepreneur, Awarding-Winning Author & Founder of Think Act Prosper (TAP) Growth Conference. You can connect him on Instagram and LinkedIn. He completed his ‘A’ license with Lodi Parachute Center.