With you recently leading a round of investment for reddit, it seems you are quite optimistic about its success but as of late 2013 (and maybe now too), Reddit remains in red even after nearly a decade of its inception[1]. Reddit CEO once said, that ads are the reasons Digg failed[2], so I believe the site would be wary of using ads to the fullest. How do you think Reddit would become profitable and would be able to…
I am an extremely patient investor. I just invested in a company that I believe will take 20-30 years to work. If reddit gets to a billion users, which I believe it will, the company will have many, many interesting monetizations opportunities. It's on its way to become one of the great monopolies of the web.
How do you conceptualize investments on that sort of timescale?
20 years ago was 1995, and 30 years ago was 1985. So much has changed between then and now. I understand that broader market trends can sometimes be predicted, but when you invest, you're betting not only on a market trend but on a specific instantiation of that trend.
How do you conceptualize an investment in a specific team and company on that sort of a timescale, when there's already so much uncertainty around what markets will even exist in 2045?