I think it's pretty clear that Dennis Crowley has been thinking about this problem space for more than a decade, and foursquare is the third (fourth?) iteration on his original vision.
I presume it means that, having seen things from the inside out, his team knows winning and losing things to spend time on.
Nearly every startup ends up with a list a mile long of potential features, ideas, refinements, communities, partners and revenue sources. Being able to pick out the right few to work on (and what to say no to) is maybe the most important skill a startup CEO can have.
A founder who has been around the same space for a long time can use past experience and intuition where a newly-minted CEO knows very little and is actually best off when they recognize that.
