> The first (and only) time I tried to make a plan with my co-founder, and there was an obvious constraint, he couldn't work with the constraint.
The tandem word here is "discipline". Once the constraint is created, then discipline is required to stay within that constraint.
Case in point: deadlines. Deadlines are fine. Deadlines without discipline with respect to scope creep is just setting a team up for failure and low quality work.
It wasn't even a "team." It was just two of us. We simply didn't get far enough, in part because I insisted that we bootstrap until we had a product.