I think part of the problem with VCs giving money to older guys to start a business, as opposed to writing software, is that if they were any good at building business that you'd kind of expect them to be rich already. When that is the case such as Joel Spolsky (49 ish) raising money for Stack Exchange there are no problems. Basically any VC would write him a cheque. But I can see the problem with a 49 yr old guy saying give us money for our startup, we'll make you billons in spite of having made zilch the last 30 years that VCs might be skeptical.