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JS: Wanted to talk to you about hiring. At what point do you determine it’s right to start bringing somebody in?
HAT: I always say that the CEO is the last person who should do any hiring at all. Because CEOs are a) really busy, b) always focused on selling, not great listeners. And then, if that wasn’t bad enough, CEOs by and large believe that if it’s a great person, they can find a job for them. And that is a not a good strategy for a startup.
The issue with [hiring] more experienced people is they have a different approach to everything. Everything isn’t a fire drill [to them], which isn’t necessarily startup culture. You’re bringing them in because they’re middle management and they’re a little more mature. But that culture clash with the young people who have been doing everything and running around is something that’s really complicated to manage.
JS: So let’s say it is a senior position. You can tell in interviews that this is somebody who’s very intelligent, but keeping them challenged is going to be difficult. How do you go about that?
HAT: If you’re worried about how to keep somebody busy, they’re probably the wrong person. You’ve got to find somebody, whether they’re senior or not, who’s excited about the opportunities. It’s almost impossible to think that anybody would be bored or wouldn’t be challenged if they were the right person. Smarts is really important. Attitude, way more important. Energy, probably even more important than that.
JS: My company is dealing with major parking companies. We’re the small fish in the sea right now. We’re not in a position of leverage over them. What gives you tipoffs that, OK, now we have some real bargaining power?
HAT: When we were building one of our businesses that serves insurance companies, which are monsters, there [was] what I called FOMO — fear of missing out. If you convinced them that the other big players were doing it, and they were going to be left behind, then lo and behold, they got on the program.
JS: What sets great entrepreneurs apart from your average business owners?
HAT: It’s like we say about movies: If you’re in the movie business to make movies, you’re going to be really happy. If you’re in it to make money, you’re in the wrong business. I think that’s absolutely true of great entrepreneurs. The money is nice. But they’re in it because they want to change things. They want to do important work.
JS: If you sit back and see somebody that’s in my shoes, what would be the best piece of advice about growing and continuing to be an entrepreneur?
HAT: First of all, I almost never sit back. No. 2, I would say, learn to sleep really fast. Then, I would say, understand that we’re not umbilically connected to any business — it’s not your family, it’s not your life, it doesn’t define you. The minute you take venture capital money, you have to understand that one of the [potential] outcomes is that the company could go on without you, [it] could be sold whether you like it or not. So you have to have this attitude that if this is the way I want to spend my life, it also may be in a different business. The question is always the same, and that is, is this something I want to be doing? Is it important work? Is it something I can get excited about?
