"I worry about being in touch with the next great thing, so I try to make up for it by being an engaged and active user of new technologies - Snapchat's a good example," he said.
It doesn't always work though. Wilson elaborated: "I couldn't imagine why someone would want to use Snapchat. I could imagine use cases, but I didn't have an affinity for the product, which is an important consideration in how I invest. We didn't pursue it, and nowadays it's probably the service my kids use most often."
Between Snapchat and the countless other hip startups aimed at younger people, it's easy to see how he arrived at the conclusion that the tech industry "definitely does discriminate against older people."
Wilson worries about "becoming an old fart." He described a fear of losing touch that causes his fund, Union Square Ventures, to "constantly want to back that super-young entrepreneur. Of course that's not always the best thing to do."
Wilson's investments include a number of notable startups. Most recently, his investment in Tumblr paid off with the company's $1 billion sale to Yahoo.