I’ve been accused of perpetuating the Silicon Valley ageist stereotypical thinking of only hiring fresh-faced, just-out-of-diapers young talent. But the reality couldn’t be further from the way I operate. In fact, while I believe that for most positions you should hire people of all backgrounds and ages who are effective (i.e., talented, hard working, and responsible), there are certain circumstances where hiring someone experienced is essential for a startup.
In the very beginning of your company’s existence, what everyone is doing is likely to change at any moment. One day you might be testing a direct sales channel, another day you might be buying tons of AdWords. One day your engineering team is building a virtual world, the next day you are a photo sharing site . By Steve Blank’s definition , you are a startup if you are a temporary organization currently in search of a scalable and repeatable business model, implying that everything and anything you are currently doing is experimentation and discovery surrounding that search.
During this fragile period, having team members with a well-rounded set of general skills is extremely important; you should be hiring people who can quickly try and test new things. For programmers, that might mean full-stack engineers who can quickly prototype new features. For non-technical people, that might mean extremely hard working, quantitative people who can quickly learn the basics of different marketing channels. It is important that these people are able to do multiple different things, because any one project might not pan out (and most likely will not).
So when do you want to hire really experienced people? When you’ve discovered an area that you know is and will continue to be an important part of your business. At Justin.tv , my cofounder Kyle and I racked our first servers, and Kyle was our de facto network engineer. Within months, we were pushing gigabits per second of video data, and the number of emergency 6 a.m. trips we were making to our data center was a perpetual testament to the hard fact that we needed a real network engineer.
We ended up finding Jon, who we recruited out of YouTube. Jon knew about negotiating bandwidth contracts. He had contacts who could give us great deals. He knew where we should build our network points of presence. Put simply, Jon had a lot of experience. Since hiring Jon, our network problems have been addressed while continuing to grow, and we now serve petabytes of video a month--something we could not have done without an experienced veteran at the helm.
We’ve done this a bunch of times. Scott, our VP of ad operations, came in and cleaned up the advertising program we were badly mangling once it was clear that would be our primary revenue generator. Jonathan, our CRO, was the founder of IGN, the first big video gaming network; he joined the team when it was clear that gaming video and Twitch  were the future of Justin.tv and we would need to establish relationships in the gaming industry.
My general rule of thumb at Exec  has been that as a founder, you should do the first version of everything yourself. Build the first product, test the first sales channels. By doing things yourself, you can quickly discover if they will pay dividends (or if it is time to move on to the next experiment). Once you discover something worth doing, then hire a professional to come in and clean up the mess you’ve made.