The pursuit of an entrepreneurial venture feels a lot like jumping off a high cliff into deep water.

It's scary at first and there's no going back once you leap, but after you muster up the courage, it is one of life's most exhilarating experiences.

Before you hastily rush into a triple backflip dive, it is best to do some homework and prepare. Is the water deep enough to attempt a safe dive? Has anyone jumped from this point before (and survived)? After I jump, is there a way for me to get back to land safely? Is getting hurt worth the risk?

Entrepreneurship is no different. Success is about more than just quitting your job and leaping head over heels into your venture. You first have to do your homework.

It's hard to define the right time to begin a new endeavor, and the reality is no time is ever going to be perfect. But before you take the plunge, here are three questions to consider.

1) Are you personally attached?

When I started my latest company Porch.com, I was out to solve a personal problem I was having myself--finding a great professional to work on my family's home. I experienced first hand the frustration and pain so many homeowners feel. My personal connection to this problem has been one of the major motivating factors in building the business to where it is today.

Deeply caring about what you are working to solve keeps you working late into the night and through the inevitable rollercoaster ride that is the startup journey. Without a personal connection, it's just too easy to give up when times get tough.

2) Do you have a competitive advantage?

When Russell Wilson, quarterback for my beloved hometown team the Seattle Seahawks, was drafted, he didn't fit the mold of what you would assume would be an all-pro quarterback. But Wilson proved that he had other competitive advantages. What he lacked in height, he made up for in competitiveness, leadership, accuracy, and speed. His unique abilities was part of what sparked the Seahawks recent success.

Business is the same--to win, you as the quarterback of your team, must have a unique skill set that creates a competitive advantage. There will always be competition in a market or space and will almost certainly bring others with the same idea as yours. Thus, to win, you have to be different. Maybe you have a unique set of skills or are especially gifted at bringing together an amazing team, or have the network to be able to make your company take off. Whatever it is, you should align your business strategy to your unique gifts in order to give you the best chance of winning.

3) What do you want and what are you willing to sacrifice to get it?

Sometimes you have to first come to grips with what you are willing to sacrifice. Fully pursuing your business forces you to look closely at your priorities and decide where you want to spend your time and energy. Building a company requires tremendous cost and sacrifice. I believe no CEO can ask their team to give more than they are willing to give themselves and thus if you want to have a high-functioning team, you will need to set the bar.

Be conscious when you take that leap--don't slip and find yourself falling. Be informed, be conscious, and when you are ready--jump.

Published on: Mar 19, 2015