Mark Zuckerberg once coded a program to help him beat a schoolchild at Scrabble, according to a lengthy New Yorker profile of the Facebook chief executive.
Zuckerberg wrote the code after the daughter of friend beat him in their first game aboard a private jet.
The flight landed before the game could finish, but Zuckerberg's program was winning by a small margin.
Mark Zuckerberg's ambition has been well-documented, but a simple game of Scrabble has revealed to what lengths the tech billionaire will go to win.
The New Yorker's Evan Osnos has written a lengthy profile on the Facebook chief executive on Monday which details the story of Zuckerberg facing off with a highschooler.
According to Osnos' telling, Zuckerberg was aboard a private jet a few years ago and was passing the time playing Scrabble with the daughter of a friend.
After the high-schooler won the first game, Zuckerberg wrote a program which would process his letters and show him all available words, and the pair had a rematch.
"During the game in which I was playing the program, everyone around us was taking sides: Team Human and Team Machine," the unnamed girl told Osnos.
It isn't clear who won the second round. The game was cut short when the plane landed although Zuckerberg and his program had a narrow lead.
The anecdote is illustrative of Zuckerberg's competitive side. According to Osnos' profile, the Facebook CEO loves board games such as the puzzle game Ricochet Robots and military strategy game Risk.
This competitive streak comes to bear in his business dealings. Osnos spoke to several Silicon Valley executives who had at one time been fierce competitors of Facebook.
Former Twitter CEO Dick Costolo described Zuckerberg as a "ruthless execution machine, and if he has decided to come after you, you’re going to take a beating."
Twitter and Facebook are direct competitors in social networking and advertising and, according to the book "Hatching Twitter", Zuckerberg once scathingly described the rival firm as "a clown car that fell into a goldmine."
Reid Hoffman, founder of LinkedIn, told Osnos that Zuckerberg deliberately kept his distance because he too was building a social network. "For many years, it was, like, 'Your LinkedIn thing is going to be crushed, so even though we’re friendly, I don’t want to get too close to you personally, because I’m going to crush you.'"
He added that he and Zuckerberg are now good friends.