Even next to the most eccentric entrepreneurs, Marco Benvenuti is an outlier. He’s the guy in the red poncho in a sea of suits, darting nimbly between disparate topics of basketball, musical theater, and writing code. He’s the bull in the china shop—only this bull is driving an Alfa Romeo.

But don’t let his showmanship fool you. “To do what I’ve done, you have to be obsessively committed to not failing,” Benvenuti says, reflecting on his consulting firm turned tech company, Duetto, which he launched in 2010. “People make the mistake of thinking that I don’t take things seriously.”