Dennis makes some seriously cool maps. The below were done for a book parents would read to their toddlers. Here's one of Chicago:

And one of Washington, DC:

For these stylized maps, Dennis mentioned that he is of an old school camp of cartographers that start with nothing. A blank sheet of paper. Then he adds to his design until the most minimal and necessary elements are there.
He mentioned an alternative and fairly popular approach is to take a large or "larger" data set of map features and stuff , and then proceed to subtract things from it until you feel only the necessary things remain.
We saw some of those maps that start with a lot and try to go to a little versus his maps that start with nothing. His approach of addition is better.
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