I think there's an interesting contrast here between US and European attitudes about startups. Here in the US and California is particular it's regarded as a mark of wisdom and maturity to say 'fail early, fail often, because failure is a fact and you may as well exploit it'. It's OK to say your first x ventures went bust as long you can articulate what you learned and still exhibit Thomas Edison-like persistence. Over in Europe, on the other hand, mentioning that you have been involved in a string of failures is like saying you recently contracted leprosy or something. Even if people admire your persistence, they'll want to know what happened to your previous employees and investors, and you may be classed as visionary but irresponsible.
I'm Irish BTW - I like living in CA because there's a more freewheeling, 'take a chance, change your life' attitude...and yet I am often scared off projects by the risk/reward calculus. I wonder if other immigrants have a similar experience.
Although broad trends might be visible across a whole population, it's also who you hang out with. I'm not American (Australian) but definitely there are wildly varying attitudes to risk and failure within the same community. Depends on the person. I assume it's the same in the US - some people would be impressed with your fortitude if you told them you'd started 5 failed companies. Others would be horrified.
Surround yourself with the first type! Might be harder to find than in the US, but there's got to be plenty around. Here might be a very good place to start.
I'm Irish BTW - I like living in CA because there's a more freewheeling, 'take a chance, change your life' attitude...and yet I am often scared off projects by the risk/reward calculus. I wonder if other immigrants have a similar experience.