CE(Uh)O

No Doubts

Fred Wilson states that (a wise VC he knew stated):

A CEO does only three things. Sets the overall vision and strategy of the company and communicates it to all stakeholders. Recruits, hires, and retains the very best talent for the company. Makes sure there is always enough cash in the bank.

Fred goes on to say:

I’ve learned that great CEOs can and often will do a lot more than these three things. And that is OK. [...] But I have also learned that if you cannot do these three things well, you will not be a great CEO.

I wish Fred had posted that on the web a year before he did, and I wish I was wise enough to understand what it meant at that time.

When we took Vanilla through the TechStars program in Boulder in 2009, we really went there for the mentorship & networking. The program most definitely delivered on that account, and we came through a gruelling 3 months with our minds in heavy “listen to your mentors” mode. After leaving the program, we were able to raise a round of financing, and Vanilla’s Board of Directors was born.

We have an awesome board of directors at Vanilla with, we believe, some incredibly smart people who bring unequaled insight to the table. This fact, combined with the fact that we had just come out of a program where we had been heavily (and happily) mentored led to one powerful problem: I was not a good CEO.

The part of Fred’s quote above that got me was that a CEO “Sets the overall vision and strategy of the company and communicates it to all stakeholders.”. I failed at this job. Miserably. Instead of coming into board meetings with strong opinions about what we are doing and where we should take the company, I was deep on the other side of the fence: asking (practically begging) for advice, always willing to accept criticism on decisions to the point where I never sounded confident in any of them. I treated our board of directors like mentors instead of equals.

The hard lesson that I’ve learned over the last year is that when you put yourself in a diminutive position, people will treat you accordingly. In other words, if you act like you might be wrong, people will assume you are wrong. And if you act that way all the time, they will think that you just don’t have any idea what you are talking about.

It’s a hard fact to remember, but for all their experience, investors put their faith (and money) into your company (ie. you) because you are the experts in your field. You should always have the strongest opinions about the direction of your company from day-to-day tasks to overall vision & strategy.

I’ve spoken with many CEO’s about the struggles of being one, and there are many pitfalls that my friends and colleagues have experienced – this one being no exception. I hope that someone (perhaps the latest companies leaving the warm embrace of TechStars) reads this and takes it to heart.