Michael Arrington talked about entrepreneurs the second time around today. I think he should segment that audience further into dot com era and other era projects.
Generally speaking, experience counts for something. So you’d expect entrepreneurs who’ve been through the ups and downs of a tech startup to have an advantage over the newcomers. Or at least have an equal chance at success. But in fact the opposite may be true. A number of venture capitalists I’ve spoken with have said that too many “old guard” entrepreneurs are not being bold enough in their business decisions, and it’s hurting their startups.
Here in Chicago this is even more pronounced. There are a number of people who talk about amounts of funding they raised in 1999. They live off that first mover advantage. Why aren’t people judging each deal independently of the personalities involved?