It is more of a general concept of the ladder rather than the specifics of how things should rank. And it is about perceptions not true success. Personally if you tell me you have a startup that has $2m in funding from Sequoia I would think you are doing pretty well on the entrepreneurial ladder. That may just be me.
I corrected the wording. I meant that you have moved on from the 1st but it was not a big success.