I'm neither Paul Graham, nor a venture capitalist. I've never invested in a startup. However, I have been involved in the process with potential investors deci

I'm neither Paul Graham, nor a venture capitalist. I've never invested in a startup. However, I have been involved in the process with potential investors deciding whether or not to invest in a company -- on both sides of the table. I can't answer your question, but I might be able to lend some relevant conversation on the topic. Investors, especially those who specialize in early-stage startups, take a lot of risks. We all know that most startups will fail -- and those that don't are not always wildly successful. There are plenty of ramen-profitable startups that will piddle out, and plenty more that never even get to that point. Because of the inherent risk involved with investing in general, it makes sense to take as risk-averse an approach as possible. That's why YC-backed companies are built on such solid, great ideas (the best foundation possible) -- and even many of those, even with Y Combinator's full support, still fail. Whether or not pg has regrets is a question that only Paul himself can answer (and I hope he will), but my opinion is that his approach is the same that I take towards my investment portfolio: maybe a slight tinge of missed opportunity, but the decision whether or not to put money into a company is calculated rationally. Because of this, there's no real regret to be had.