I really enjoyed your collection of stresses for start-up entrepreneurs — felt like a glimpse into my recent past, and daily thought cycle!

Three things that I’ve spent a lot of cycles on:

1) Are we setting up our culture for success over the long-term? Are we working long-enough hours, but not at too much of a sprint mode, which is likely unsustainable over the long-term? Have we nurtured and maintained a collaborative environment where people know they have input in all areas, but also have ownership over their areas? Do we have a Product Development process in place that provides adequate visibility for everyone about schedules, features, and goals?

2) How to balance the tradeoffs between “money now” vs. “money later”, and the varying trade-offs over terms?

3) Several folks on your list have stated this, but it’s always the monster in the room — constantly stressing over our untested assumptions and maintaining transparency for investors/friends/employees, who trusted us with their financial and emotional investments.

Onward!

Dave