Optimists downplay problems and are annoying to work with, especially if in charge. I rather work with pessimists any day. (As long as we are not talking about like, grumpy vs happy, but more in a technical sense).
There's a mentality I've adopted that I find helpful that I call "hopeful pessimism". It's the descriptive form of "Hope for the best; prepare for the worst". You expect the worst outcome, but hope you're wrong.
I think most of the devs I've enjoyed working with have similar perspectives, and often include a dark sense of humor with it. As when the hope runs out, all you're left with is something dark, and being able to laugh at the absurdity of it, to make light of it and minimize it that way, is a helpful coping mechanism, as well as one that can help bind a team together. And also helps avoid falling into despair along the way as the hits come; you can stay hopeful and focused on the desired outcome.
Maybe it depends on where in the company they are, but it seems to me that most successful founders are pretty optimistic. I know I wouldn’t want to work for a pessimist, but I agree that I wouldn’t want to be led by a completely unrealistic optimist. There needs to be some awareness of reality, but at the same time the vision and ‘reality distortion’ can help drive big successes and rally teams imho
(Over)optimistim in founders is adapted to the current environment where the competition is over who can raise the biggest mountain of cash. I predict other qualities will become more desirable as the 20 years bull market starts to fade.
I’d say Bezos, Larry & Sergey, Jobs, even Zuck seemed pretty highly optimistic in their early days and leadership styles, and that has nothing to do with the current funding climate.
