Venture Capital Adventure

Since I was in elementary school, I always wanted to travel around the world on a sailboat. This summer I came one step closer when I joined a sailing club and learned how to sail on boats over 30 feet with a crew. Reflecting on some of the experiences I have had working with the expansion stage companies in our portfolio, I actually found that sailing a large sailboat (not that 30ft is so large) is actually a lot like running a business.

In sailing, like in business, there are many different factors you need to consider to make the boat move in the direction that you want. To start, you need to know what direction the wind is blowing. Depending on the wind direction relative to the sail, you have to know how the sail should be trimmed. You also need to plot your course because depending on the wind direction relative to where you are trying to sail to you can’t always go in a straight line.

Also like in business, you cannot just put the boat on cruise control, sit back and relax. In good weather, the wind blows steadily in one general direction, but it is constantly changing by a few degrees in either direction. Your helmsman and crew need to know how to control their sails and steer the boat to compensate for these changes as they come. They need to make sure that the wind is always flowing over the sails evenly. This is how you harness the most power out of the wind and achieve the best performance out of your boat. For this to happen, it is critical that the captain makes sure that his entire crew is all on the same page and knows exactly what to do at any given point in time to ensure a safe and efficient voyage.

There is, however, one additional similarity between running a business and sailing that in sailing is seemingly obvious, yet in business has eluded entrepreneurs for years… That is, before you go anywhere, you have to pick a destination, otherwise you and your crew might not be sailing to the same place.