I can't speak for Ed, but "fail" and "can't" are still very much words in my vocabulary, and I worry almost daily that we can't build the product we'd want to use and will fail in the market. Maybe that's a problem for me. It does seem to be a negative when talking to people about my startup; they pick up cracks in the facade of perfect confidence fairly often.
But I don't want to be blindsided by potential problems; I want to catch them as quickly as possible so they can be fixed. My role in the startup has always been the engineer, and as an engineer, it's my job to be pessimistic. (I used to have a business-type cofounder who was much more gung-ho, but he left for B-school, and now I've gotta do both. Concentrating on the product first...)
One of my favorite quotes, though, is:
"Courage is not the absence of fear. Courage is being afraid and doing what you have to do anyway."
I'd much rather imagine everything that can go wrong now than be blindsided by it later.
I have always had a lot of respect for you and your contributions here.
At first, I was a little surprised to hear you say, 'but "fail" and "can't" are still very much words in my vocabulary'. I never imagined you as someone who "worried".
But then once I thought about it, it's no surprise at all. There is no one philosophy or "thought set" that makes one a successful hacker or business person. This may be the biggest takeaway for the OP - yes you can; there are very few absolute disqualifiers.
This discussion reminds me of my first 2 mentors, both very successful and great leaders. Neither would accept "no" and both got upset when I used the words "can't" or "but". I know it sounds silly now, but I have maintained that philosophy ever since.
Sometimes forcing yourself to "find the possibilities" brings something out from deep down inside that you never knew was there.
One of the few people I have respect for in my career had a phase for this regarding the progress of projects, and I think it applies to start-ups in the sense that sometimes people are blinkered about what they are doing and that is this:
"Disappoint early"
In other words, as soon as you are aware of a problem - Raise it. And then discuss it and work it out.
But I don't want to be blindsided by potential problems; I want to catch them as quickly as possible so they can be fixed. My role in the startup has always been the engineer, and as an engineer, it's my job to be pessimistic. (I used to have a business-type cofounder who was much more gung-ho, but he left for B-school, and now I've gotta do both. Concentrating on the product first...)
One of my favorite quotes, though, is:
"Courage is not the absence of fear. Courage is being afraid and doing what you have to do anyway."
I'd much rather imagine everything that can go wrong now than be blindsided by it later.