ServiceNow CEO Bill McDermott attributes his high emotional intelligence (EQ) to running a deli as a teenager, where he dealt with 500 diverse customers daily. This experience provided a critical foundation for understanding customer needs, a skill he views as essential for any business leader.

As tech's influence grows, the disruptive "asshole" persona is no longer celebrated. To build trust with investors, employees, and customers, founders must demonstrate respect for the communities they operate in, adopting a "give more than I get" mindset.

Craig Newmark reframes his "subtractive" career moves—like stepping down as CEO—as a strategy for effectiveness. By acknowledging his limitations and sharing power and money, he builds "networks of networks" that accomplish far more than he could alone.

Successful founders often exhibit a paradoxical blend of traits. They need the arrogance to believe they can disrupt incumbents. Simultaneously, they require the humility to do unglamorous, hands-on work—like personally delivering 1,000 packages—to deeply understand the problem they are solving.

Many successful sales professionals initially disliked selling, viewing it as simply taking money. Their perspective—and success—only changed when they understood that true selling is about serving people and helping them solve problems.

Hemant Taneja rejects the trope that founders must be ruthless to succeed. He actively fosters a culture where kindness and ambition coexist, believing the glorification of the "asshole symptom" is a false and unnecessary ingredient for building great companies.

After his public company went to zero, Matt O'Hayer became a charter boat captain, fixing toilets and serving guests. He described this ego-crushing experience as a "gift." The forced humility taught him servant leadership, a crucial mindset that underpinned the stakeholder-focused culture of his billion-dollar brand, Vital Farms.

John Zimmer doesn't regret the difficult times of building Lyft. He views those struggles as formative experiences that made him a more empathetic entrepreneur, parent, and husband. Hardship should be embraced as a critical part of personal and professional growth, not just an obstacle to overcome.

How a founder interacts with waiters and other service staff provides a candid glimpse into their personality and empathy. This simple observation can be a powerful 'poker tell' for an investor assessing their character.