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Why I Signed Up To Kite Surf With Some Famous Entrepreneurs



I’m dripping with sweat after underestimating the pleasant walk from Google’s office in Silicon Valley to my next meeting. I’m thinking to myself “Why did I bring this stupid DSLR camera which is making my backpack so heavy?”

Anyway, I arrive at my destination. For the first time on my San Fran trip, I’m actually early for a meeting. Every other meeting I have been late to because Google Maps really does make everything look so close together….lol.

I meet my well-known contact at his office, and by the end of the meeting, I’m in. In what you ask? The club, network, business – whatever you want to call it. I know this because I am asked to go and get kite surfing lessons.

I used to skate half pipes, so I figure that I’ve still got this extreme sports ability in me. It’s not the sport itself that fascinated me; it’s the people that participate in it and the opportunities it presents. All the current people I want to meet all seem to do it (and do it well).

There’s plenty that can go wrong and after saying yes I’ve realised that it’s definitely harder than I thought. So what. Sometimes, we have to take a risk. The best decisions we make are based on a gut feeling, not scientific evidence.

The corporate word has failed to teach me that everything isn’t based on facts. The corporate world has also failed to make me agree that every problem has a solution just like in university.

The four things that held me back and may be holding you back from an amazing opportunity like this are:

1. I was scared of being an elephant bumper

Elephant bumping is where you go out of your way to spend time with people who are very famous when you’re not (at least that’s what it means to me). The inference here is that because you are not on the same level as them, you shouldn’t be spending time with these influential people.

I’ve realised this is wrong and in fact, famous entrepreneurs are just like everyone else. We somehow think that they are superhuman, but they’re not. They eat normal food, enjoy meaningful conversations and have fun just like the rest of us (who knew).

When you forget that these people are highly successful, you are able to talk to them on the same level. The moment you get star struck you’re screwed. The bottom line is this: forget about whether people are famous or not when you meet them.

2. I thought I would have nothing valuable to tell them

No one has all the knowledge in the world. Even if someone is successful, there is always something that you know that they don’t – take advantage of this. For ages, I held back from reaching out to famous entrepreneurs and even dreaming that I could go kite surfing with them.

I somehow felt inferior and like I didn’t have anything valuable to give. When you have nothing to give it’s challenging to spend time with high profile people. I’m the kind of guy that never likes one-way exchanges of value.

What I’ve just said about have nothing valuable is a myth. In my humble opinion, I know blogging, social media, tech, personal development, and entrepreneurship at a super-human level.

Back to the office in Silicon Valley, as it turns out, I had a fair few trade secrets about tech and business. Some of the things I knew were sort after. The moral of the story is that you have to find your unique skill that the other person doesn’t have when meeting famous entrepreneurs.

3. I didn’t back myself

A lot of what I have described in this post comes down to a lack of belief. When you don’t believe in yourself, no one else will. How can you expect someone else to back you when you don’t? Well, you can’t.

The moment I believed that I was just like them, my luck started to change. I created my own luck like I always do. The thing is that I did back myself to a point. I mean I spent $5000 flying to the US with no meeting booked. That’s backing yourself, isn’t it?

Well, it is to a point. The trick is you’ve got to go all the way and not be half pregnant (sorry if this is politically incorrect it’s the best I could come up with).

“The shift happens when you place all the poker chips of life on the table, and you’re prepared to lose it all”

That’s when success comes knocking at the door, and opportunities like kite surfing reveal themselves.

4. I was nervous about my failures in business

Until I had gone to Silicon Valley, I didn’t realise how important my past failures were. Before my trip, I thought failures in business were to be frowned upon. When I got there, I realised that failures were celebrated like some god from the Roman Empire who had just won in battle.

The smell of the fresh blood of failure is what keeps Silicon Valley breathing at night. It’s the pulse of the landscape, and it’s not to be feared. Somehow I thought that if I revealed my failures, it would make me not worthy of an opportunity like kite surfing with these tycoons.

As it turned out, as usual, I was dead wrong. Failure is to be rejoiced because it shows that I take action instead of sitting on the sidelines and commentating like most people.

***Final Thought***

Be proud of who you are and don’t let limiting beliefs stop you from incredible opportunities. Often, your success lies on the other side of these BS fears. Forget about the labels and just be you. As long as you’re being authentic, you’ll attract the people you want to be surrounded by.

While I still have no idea how to kite surf I have faith that I’ll figure it out. Failing that, I’m a good swimmer, so maybe I can just go scuba diving instead….haha. If you see me on a beach near you trying to kite surf and falling over, don’t laugh and know that I’m doing my best.

What’s holding you back? Let me know on my website or my Facebook.

Tim is best known as a long-time contributor on Addicted2Success. Tim's content has been shared millions of times and he has written multiple viral posts all around personal development and entrepreneurship.You can connect with Tim through his website



  1. Ran Mendis

    Dec 31, 2016 at 6:00 pm

    Very inspiring and brilliantly written. I’ll be always remembered that the uniqueness I have being genuine me, myself is very important. It’s very true Tim we may have a very unique skill that a successful man wanting to develop so no need us to be inferior or nervous. ” Respect all Fear none” seen written on a T-shirt of a stranger which has become my favourite these days. Again love and respect and wish you all the good health in 2017. Take care mate. Regards

    Ran Mendis

    • Tim Denning

      Jan 5, 2017 at 12:42 am

      Ran I also love that quote as well. Thanks for the kind words and best of luck in 2017 to you too 🙂

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