One of the amazing experiences that comes with investing in entrepreneurs is seeing the entrepreneurs evolve over time. Early on, the entrepreneur is blissfully ignorant about what lies ahead and grinds it out to (hopefully!) to an early milestone of a million recurring, willing the startup forward. Then, slowly, it becomes clear that the entrepreneur needs to go from doer to manager (see Maker’s Schedule, Manager’s Schedule).
As a manager, the entrepreneur struggles. People require trust, and systems, and patience. The entrepreneur wants results, now. Slowly, after many mistakes, this whole people thing starts to come together. Culture starts to become important. More lessons, more learning.
Then, the next challenge: becoming a manager of managers. More people, more processes. More debating whether to work in the business or on the business. Onward and upward.
The entrepreneur evolution is fascinating. No two journeys are the same, but all are interesting.
What else? What are some more thoughts on the entrepreneur evolution over time?
David Cummings on Startups 
Also, interesting to see entrepreneurs struggle through the transition from startup to an enterprise (via growth or acquisition) and the lessons they take with them for the next time.
I hardly call myself an entrepreneur, as I’m just months into independent small biz consulting, but one thing I’ve seen in my own evolution thus far is the ability my brain has to grab onto and efficiently extrapolate simple, “aha moments” (e.g. we could create a simple training for customer group X…”) into more bold and comprehensive plans in which money can be compounded on top of that idea (e.g. “once we obtain critical mass, our new customers could be A, B, and C…”). I’ve enjoyed this evolution. Good post!