reality/inexperience I would put largely on myself, and in the "business role" sense of the word. Looking back we were far more solid than we even realized on the tech side, compared to peers in the industry.
What we lacked was all the rest - sales, marketing, business development, someone ensuring that the market verticals we were in were strong and who knew when to start looking into new lines of business. While I had some of the latter, the marketing and sales side was always difficult for me.
Lessons definitely learned, and I'm very excited for try #2!
And yep, the team matters the most. People forget what that word means, but when you're in a functional team you'll simply know it. I describe it as that feeling of being stuck on some tedious work you're hacking away at feeling burned out on, leaving for the day, then coming in the next morning to find your co-worker who works late pushed that project forward for you while you were sleeping.
Sounds silly right? But that is severely lacking in most corporations today - that idea of team spirit and team members having each other backs like that. You certainly see it in startups, but that seems to almost be it save very small pockets with competent managers in large corporations almost by accident rather than design.
Reading your other posts in this thread you would have fit right in to our ops team back then. Basically our job was to make sure that phone never rang at 2am, and if it did we had fucked up somewhere so we didn't mind it as much as the only person you typically had to blame was staring back at you in the mirror. Everyone was empowered to keep those calls from coming in though. If your company requires heroics to operate, you're doing it wrong.