"On the other hand, if you still got to pay the bills, and have a family,"

You're right. And all of this is nonsense anyway. The people who encourage all this risky behavior aren't going to be there to clean up the mess when you fail and can't pay your bills. And passed up your chance to go to Harvard to do YC.

It pays for them to encourage you to take big risks and encourage big ideas. And they will pick from those risks and if 2 in 10 are a home run then they win big. They are spreading the risk over many ideas (you're only doing one idea) and they are risking other peoples money in general. (Sure they have reputation and other worries but not the same as your loss.)

My guess is, and this is only a guess, that when they evaluate an idea they don't take into account at all what will happen to the founder of the big ambitious idea when it fails. It probably doesn't even enter into the decision to fund the idea or not.

It's like encouraging a friend to go to Hollywood and follow their dream to become a star. If they succeed you have a friend who's a Hollywood star. If not no loss on your part.

I got my current job largely by the fact that I had a failed startup on my resume.

What type of failed startup was it? Was it a VC backed startup that failed? If so then there is definitely a halo effect in that (in the startup world). But that will only work with the 1% of the world that cares and understands the startup world. Unfortunately the traditional world (where many failed startups founders might end up) doesn't view it the same way.

It also depends on how long you spent doing the startup and the opportunity cost of doing so. It's one thing if it takes a 6 month chunk out of your life and another thing if it takes a 5 year period. And prevented you from doing something else.

Each circumstance is different of course.

I spent about two years on it, but a lot of that was weening off my traditional job. The tech worked perfectly eventually, however me being a business person and learning to market was not so successful. Most definitely not VC backed. More MC backed.

Exactly, would Gabriel have been able to start DDG without the money from selling NamesDatabase (or other private money)? I think a lot of these guys who have "made it" forget how difficult resources can be for the rest of us, especially when talking about webscale projects.

I was certainly in a great situation. However, we weren't living off any more than my wife's salary (including any DDG investments), so I would say the answer was yes.

Would someone who had a mortgage, and kids to pay tuition for had that luxury though?

We have kids and a mortgage.

I respect that, but I think having that financial cushion also affects you emotionally. You have the freedom and luxury to take your time and be more patient, and not take any rash short-term risks because money isn't an immediate issue.

That's true, and also brings in the question why rich people don't (typically) start ambitious startups with all their money. Elon Musk is an opposite example however; all his projects being something really big and ambitious on blue ocean markets. There would be so much to explore beyond making the next twitter, but it seems that people aren't just crazy enough.