Difficult Is Good

Entrepreneurs come in all shapes and sizes. There is no single formula for determining what type of entrepeneur will succeed. But one of my favorite stories about entrepreneurs comes from Don Valentine, the founder of Sequoia, which is one of the best venture capital firms in the business.

When one of the younger partners in the firm started, Don took him aside and drew a four square quadrant. Along one axis, he put "easy to get along with" on one end and "hard to get along with" on the other end. One the other axis, he put "normal" on one end and "brilliant" on the other end.

He then said, "sometimes we make money with brilliant people who are easy to get along with, most often we make money with brilliant people who are hard to get along with, but we rarely make money with normal people who are easy to get along with." 

That has been my experience as well. Getting along with difficult entrepreneurs is one of the secrets to success in the venture capital business. It is also true that finding management teams that can get along with difficult entrepreneurs is critical to succeeding in venture investing. 

The "brilliant entrepreneur" can do a lot for a company. They can come up with the initial idea. They can create the vision and market position. They can get the initial product built. They can set the values and mission. But they cannot do it all by themselves. So they will need a team of people around them to execute the mission, achieve the vision, and do the hard work of building the business. 

Venture capitalists often find themselves in the middle of this stuff. They sit on the boards and sometimes control the boards. They are often asked to choose between the difficult brilliant founder and the easier to get along with "operating management." In a perfect situation, the boards will not be forced to make this choice. There are tools and techniques that can be used to help everyone get along.

I've mentioned before on this blog that coaches are one way to address this issue. I have seen a number of difficult situations where coaches made a huge difference. 

Recruiting is also an important way to deal with this situation. There are some people who have an easier time getting along with difficult people. If you can find them and get them into key positions in startups, you will be better off.

The reality of startup investing is that the greatest entrepreneurs are almost always challenging in some way or another. It is never easy to work with them. But they can and do make great things happen and it is often worth every aggravation to be invited along for the ride, whether you are an investor or a management team member.