Damn, this was a long time ago.
I was learning how to do more "dynamic" sites, doing freelance work, and teaching "web development" part-time. While working late at the school one night, a conversation went from finding truly local eats to "why don't we built this out." I do remember it ended at about 4 am.
the First idea locked and loaded. I designed it and started to build it. The URL was purchased, and we started to build it out, I believe (details are vague), but I do remember something about funding from a local law office; they also gave us office space.
What did we get wrong? So many things, but if my memory serves me correctly, I remained the designer and developer while the other three members made sales. Months of building this out and zero sales. ZERO. The lead sales guy was a firefighter, and I knew nothing about approaching that side of the business. It was a fun whiteboard process, but ultimately we didn't have a real plan, know our customer's needs, nor did we do any real research.
Projected lasted about 10-12 months