Best And Worst Decisions - Dick Costolo

A few years ago, for Startupping, I asked several entrepreneurs about their best and worst decisions. With the shuttering of that site, their answers vanished from the web. I’ll be reposting them here. This was originally posted on February 20, 2007:_

Dick Costolo is currently COO at Twitter. He was formerly the CEO and cofounder of Feedburner, the leading provider of media distribution and audience engagement services for blogs and RSS feeds, which was acquired by Google. Previously, he cofounded and was CEO of Spyonit.com. Spyonit was sold to 724 Solutions in September 2000.

The best decisions I’ve made have all been hiring decisions. When you really are feeling the pain of not having a certain kind of person in the company, it’s easy to hire the first interviewee that walks through the door, but it’s critically important when a company is getting started to make sure you’ve found somebody that everyone on the team thinks is the right person for the role. People always tell you to hire A players, but the person also has to be a great cultural fit with the team you’re assembling and with the kind of company you want to be.

I’ve made loads of mistakes so I’ll try to think of one with a good lesson for startups - one of the biggest mistakes I made in a previous company was accepting a high dollar contract once for something that wasn’t core to the vision of the business we were running at the time. While the revenue initially feels great, there’s nothing worse than pursuing a piece of business that isn’t core to the startup’s vision. Lesson learned - once you decide what it is you are going to do, don’t pursue efforts that distract from the vision. One of the hardest lessons an entrepreneur has to learn is what revenue to turn down. You can certainly decide to change the vision and zig when the market zags, but in a startup, everybody has to be working toward a very focused vision, and chasing down side projects can be a real distraction (and probably ends up costing a lot more in terms of long-term resources than you’d expect).

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