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The Wind In Your Sails: Entrepreneurship As Reflected In Kiteboarding

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I had the pleasure of being introduced to the kiteboarding community by Bill Tai and Susi Mai this past weekend. They run an incredible organization, MaiTai Global, which brings entrepreneurs and kiteboarding professionals from all over the world together for four days of kiteboarding, panel discussions and brainstorming.

In recent years, kiteboarding has garnered a loyal following amongst entrepreneurs. It’s not hard to see why entrepreneurs have taken to this amazing sport: the parallels between launching a kite and launching a company are striking and make for an interesting comparison. Kiteboarding requires patience, the right kite, and finding the sweet spot once you’ve launched. These are key lessons for any successful startup, the most important being developing an unspoken relationship with the “wind.” To read the market correctly, go deep and ride the wave. You can’t learn to kiteboard overnight, just as most “overnight successes” took many years of calculated planning and analysis of product and market.

Be Patient 

When you first want to start a company, you expect everything to move in hyper drive. Slow down. Just because you think you have a good idea does not mean that it is. Do your market research, speak with potential customers and investors. As echoed in previous posts, find your product-market fit and validation. Good companies take a long time to build. Move slowly; teach yourself the basics before diving in headfirst. In kiteboarding it is important to start with a trainer kite to get down to basic techniques before jumping into the water. Learning how to manage the kite while on land will go a long way once you’re in the water (or snow). If you try to go too fast, too quickly, you’ll find yourself frustrated by a lack of progress.

Dress Accordingly. Select The Right Kite.

A kiteboarder’s day is very much dictated by the strength of the wind. This is a variable beyond your control. While you can’t control the wind, you can dress accordingly and chose the right kite. Your choice of kite wingspan should be dictated by the strength of the wind.

As an entrepreneur, it’s important to become comfortable working in an environment outside of your control. While running your company, every day is drastically different. As long as you show up ready to confront your challenges head on, you’ll be on the right track. You will face many challenges for the first time, don’t be afraid of failure, pick yourself back up and learn on the fly.

Pick the right kites: hire people that are experts in the parts of the business that you need to go deep in. One of the best pieces of advice I’ve been given on being a CEO is this: “only do what only you can only do.” Hire a great team to do everything else and focus on your specialty. Don’t be afraid to give up parts of the business that you’ve owned up until now. Hiring will be one of your most important skill sets. A great company is made up of great individuals doing great things together.

Wait for the Sweet Spot: Harness the Wind

Once the kite is launched, kite boarders focus on “harnessing the wind”.  They look for the sweet spot, that magical point where one feels an equal balance of pull and push between the kite and the wind, and they ride. The same goes in business: as you roll your product out and begin receiving true customer feedback, never hesitate to readjust your business in search for the right points where both product and business begin to shine. Once you’ve gotten some early success, it’s key to keep up your momentum. Expand your sales team, expose your API, move onto another platform – whatever it takes. Harness the wind for as long as you can. There are rarely “overnight successes”; rather, work towards the day that everyone finally acknowledges your existence.

This takes careful and calculated steps forward and one day, the wind will lift you up. After that, it’s up to you to harness that wind and keep rolling. Strive for that day and dig deep when it finally comes.