One Entrepreneur On the Start: Jesse Davis

This is part of a series called "The Entrepreneurs On The Start."  This interview is with Jesse Davis.

What was your first business venture?

My first business venture was a water delivery service for students on the UW-Madison campus. It was called college coolers. We sold primarily the 5-gallon bottles of water and the instant hot/cold coolers. We did $100,000 in business during my junior and senior years.

What made you want to go into business for yourself?

I had several jobs growing up working for other people and was always frustrated by the rigidity of the work environment. Good ideas were constantly being shot down and deemed unfeasible simply because the upper management was resistant to change. I decided a more open, collaborative work environment was for me, and starting the company was a way to ensure such an environment.

Would you go into business, if you had it to do over again?  Why or why not?

Yes, 100%. Regardless of economic success or failure, starting a company is a self-expanding opportunity. The networking component of starting a company is in itself worth it; I've met more great contacts in the past 2 years from doing business than I could've ever imagined. Even if my current company Entrustet is ultimately a failure, I will have met enough people along the way to make it well worth it.

What were some of your biggest lessons learned about starting a business?

The hardest thing I've had to learn has been a tolerance for ambiguity. You can do as much strategic planning and make as many financial projections as you want, but the fact is that very little is known about the future in any given startup. You cannot be sure when/where your next paycheck will come from and how big it'll be. You cannot be sure who's gonna like and who's gonna hate your product. You cannot know what will go wrong and when. You have to learn to surrender yourself to whatever happens.

Manage expectations. It's really easy to get caught up in your company's potential but it's critically important to not get ahead of yourself. Confidence is a good thing, but it's not to be overdone. Don't get excited too easily and don't be afraid of slow starts.

Any final thoughts on starting a business?

Surround yourself with good people. From co-founders, to advisors, to service providers, the quality of your company has a lot to do with all the people involved BESIDES YOURSELF. Surrounding yourself with smart, eager people is the best way to position yourself for success.

Jesse Davis is the co-founder of Entrustet.com, which integrates online assets such as email, banking and investment accounts, photos and videos, and online memberships into legally endorsed estate plans.