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.

• Focuses heavily on the mechanics of early-stage executive hiring, particularly bringing on a chief operating officer. Advises that successful integration requires founders to willingly share leadership duties and seek out individuals with skills that complement their own blind spots. A major example he uses is his own onboarding at Stitch Fix as an early executive, where he learned the importance of testing whether a candidate is capable of handling full board meetings and eventually stepping into a chief executive position.
• Looks for specific personality traits in founders, favoring those who are humble, intimately familiar with their business operations, and capable of acting as magnets for high-level talent. Appreciates leaders who are transparent about their weaknesses. He often references his former colleague Katrina Lake as the standard for this, noting that her clear vision, intelligence, and open vulnerability were the primary reasons he was convinced to join her team.
• Values career resilience and the unique momentum of startup environments compared to slow-moving corporate structures. Strongly prefers operators who enjoy taking risks, getting their hands dirty with daily tasks, and helping teammates grow rather than just delegating. To illustrate this, he transparently shares his own story of being passed over for a major corporate promotion in 2011, detailing how he used that rejection to pivot away from large corporate roles and embrace the intellectual challenge of a hyper-growth company.