Mike Smith is a former Walmart.com COO and Stitch Fix executive who uses a "Pity City" concept—giving himself short, defined periods to feel disappointed after setbacks before quickly moving toward the next opportunity—and openly shares how being passed over for Walmart US CEO became one of the best things that happened to him. He requires culture and values discussions before Footwork writes checks, drawing from Berkeley Haas organizational frameworks he used to scale Stitch Fix from a handful of employees to thousands, and positions himself as able to "sit in the COO seat" with founders on operational topics rather than providing purely financial guidance. Mike Smith is a former Walmart.com COO and Stitch Fix executive who uses a "Pity City" concept—giving himself short, defined periods to feel disappointed after setbacks before quickly moving toward the next opportunity—and openly shares how being passed over for Walmart US CEO became one of the best things that happened to him. He requires culture and values discussions before Footwork writes checks, drawing from Berkeley Haas organizational frameworks he used to scale Stitch Fix from a handful of employees to thousands, and positions himself as able to "sit in the COO seat" with founders on operational topics rather than providing purely financial guidance.