This essay connects four key ideas from Herb Simon's "Sciences of the Artificial" to recent research on entrepreneurial expertise: (1) Natural laws constrain but do not dictate our designs; (2) We should seize every opportunity to avoid the use of prediction in design; (3) Locality and contingency govern the sciences of the artificial; and, (4) Near-decomposability is an essential feature of enduring designs. The essay is based on a series of conversations and emails with Herb about the empirical findings of my doctoral dissertation that involved a protocol analysis study of expert founder-entrepreneurs