The cofounder and CFO of Box once made an awkward appearance on a reality TV show
Before they achieved fame in the tech world, however, Smith made an appearance as an eligible bachelor on Bravo's "Millionaire Matchmaker" reality show.
Box had about 70 employees in Palo Alto at the time (they now have more than 1,500).
The episode, which aired in 2010, casts a 24-year-old Smith as a stereotypical wealthy nerd. Matchmaker Patti Stanger goes so far as to call Smith the nerdiest guy she's ever met in her life.
"I know it's pretty rare to be a self-made millionaire at 24, but I like to think I'm a pretty smart guy," he says in the episode. "I definitely wouldn't consider myself a typical millionaire. I think most people would consider me a geek, myself included."
In an effort to loosen Smith up, Stanger sets him up with a dance coach. Smith shows up to the dance studio in moose pajama pants.
Stanger plans a mixer for Smith and another millionaire on the show to meet a group of women and choose one to go on a date with.
"I didn't have any specific algorithms in mind," for comparing the girls, Smith says.
He eventually chooses a 24-year-old woman named Arielle for his date. At dinner, he tells her that he used to play professional Wiffleball and that he's looking for a lead singer for his band.
"When I say 'band' I don't mean a real band. I mean a band that is actually a video game that I'm afraid to take out of my own living room," he says.
Overall, it seems the date went well. They kiss near the end, and Arielle tells Stanger she'd go out with Smith again.
He even shows Arielle some of the dance moves he learned. 
The date never turned into a lasting relationship, however - Smith married Yael Goshen in 2013.