Lowercase Capital partner Chris Sacca says that when he looks at his portfolio — which includes Uber, Kickstarter, and Medium — he doesn’t “have any founders or CEOs who I would consider to be normal people in any way. They’re all weird.”
In an episode of the popular podcast Startup, which is hosted by Gimlet Media cofounder Alex Blumberg, Sacca explains the type of person he likes to invest in.
Sacca, who has invested in Gimlet, tells Blumberg that he backed him because he’s “weird” enough. Specifically, he was obsessive enough about a single idea that he left a comfortable job and put everything on the line to pursue it.
Why is it good to be weird?
Sacca uses an example he’s previously written about concerning Uber CEO Travis Kalanick, who he’s known and been invested in for several years, to illustrate the type of person he looks for:
A few years ago, Uber was barely started, Travis was at my house up in the mountains over the holidays hanging out with me and my family, and he’s pal-ing around with my dad. And my dad says, “Hey, let’s play a game of Wii Tennis (Nintendo Wii).” My dad had a Wii at home and considered himself a pretty good tennis player. He’s like mildly athletic and has played in a few local tennis tournaments. So Travis is like, “Alright.”
Travis is barely awake yet. And they sit there and they start playing this Wii Tennis game and my dad is getting abused. He’s losing handily to Travis… And Travis is like, in full “Princess Bride” style, he says… “I’m playing with my opposite hand.” And so he switches the controller to his other hand.
They start the match again, and my dad doesn’t score a single point. He is absolutely swinging away and he gets no points in, and half of Travis’ serves are just aces. My dad is completely dejected. So this grin comes over Travis’ face, and… he starts thumbing over on the controller to the settings page on the Wii and to where they have the global high score. And he says, “I’m actually tied for second in the global rankings in Wii Tennis.” He was the second best player in the world in Wii Tennis.
I don’t know when the day was when Travis decided he wanted to be one of the best Wii Tennis players in the world while founding what’s gone on to become the biggest transportation company in history. But it was in that moment that I saw his true obsession with obtaining a goal. Once he sets something out as a goal for himself, he will absolutely accomplish it — at probably any cost.
He also mentions Kalanick’s habit of going to the cheapest hotels or even hostels he can find when he’s on the road, despite being a billionaire. It’s a habit he’s kept since his cash-strapped startup days. “He’s a man on a mission,” Sacca says, citing this quirk as another example of Kalanick’s singular focus on Uber.
It’s that unusual love of competition that some can find so abrasive that has allowed Kalanick to grow Uber into a company valued at $US40 billion and growing, according to Sacca. After all, isn’t it “weird” to feel the need to master a video game and then embarrass your host by playing it as if your life depended on victory?
“There’s something very different” about all of Sacca’s favourite entrepreneurs that results in unique worldviews. “All of them have seen a problem that needed solving that most people probably didn’t notice or took for granted,” he says. “And all of them had the confidence to take the harder path, to eschew all the easy stuff they could have had otherwise, and take the hard way to fixing it.”
You can listen to the full Startup podcast episode below, via Gimlet:
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