There are a range of personalities to be found in the top ranks of the corporate world, according to Sacca, ranging from Uber CEO Travis Kalanick’s outspoken nature to former Twitter boss Evan Williams being known for trying to avoid the spotlight.
Having worked closely with both founders, as well as bosses from firms such as Instagram, Sacca suggested in June 2015, during an episode of author Tim Ferriss’ podcast, that they also shared similar traits.
“These guys are all incredible listeners,” he said. “And I don’t just mean in casual conversation. I mean these guys go out of their way to interview other people. Take Williams, for example. You’ll notice he always has a notebook with him. If you ask to see the last few pages of the notebook, he’ll show you notes from his meetings with other people – billionaires and leaders whose jobs might not overlap with his at all, but from whom he’s learning.”
Sacca also claimed Kalanick would think it a competitive disadvantage for others to know what’s going on in his head, so he’ll listen instead.
With that in mind, he suggested the entrepreneurs he worked with, and made it big-time like Kalanick and Williams, were constantly learning, modeling, researching and gathering data.
Further adding to his advice on what it takes to be an entrepreneur, Sacca recently claimed at a Collision Conference that being normal wasn’t always in a founder’s dictionary.
When asked what it was he looked for in an entrepreneur, he claimed to search for a degree of dysfunction, suggesting that while being normal made for a good employee, it wasn’t always the case for an entrepreneur.
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“This is a very special, different journey that’s not available to everybody,” Sacca said. “You have to be a little obsessive. You probably have some personal issues that make you different. You may have trouble relating to other human beings. You don’t accept failure very well. Maybe you’re a little manic-depressive. If none of those things sound familiar, you should think about doing something else.
“Also, having done this for a lot of years now and having a lot of data points, I can just tell. I can smell it on them, whether they’re going to go the distance or not.”
This all comes down to confidence, he explained. “Our best founders, whether it’s Kalanick, Williams, or [Kevin] Systrom [of Instagram], they just believe in the inevitability of their success.” When things don’t go as planned, he said, “they don’t wallow, they just know it’s going to work out.”
When Uber was but three cars in San Francisco, Sacca said, his vision for Uber was already large. “In the earliest days, when Kalanick was pulling eight-hour days in our hot tub up in Truckee, we were talking about international expansion. We were talking about moving food and packages around.”
Likewise, Systrom was projecting 50m users for Instagram before it even had any. “He said it so calmly, it was magnetic. It was alluring,” Sacca said. “I said, ‘I can’t not be involved in this guy’s company.'”
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