Uber And Entrepreneurial Psychology

I’m working tonight on something where I had to catch up on a video clip. I watched Arrington’s interview of Uber’s CEO which kicked off last week’s TechCrunch conference. I didn’t attend that day so missed the talk and posts around it.  The entire discussion is excellent and shows many facets of Kalanick that are interesting (to me). But, I wanted to focus on the first five minutes of the talk. You can watch it here [video link].

If you’re a startup CEO or early-stage investor, I’d recommend watching these first five minutes, which expose a nuanced entrepreneurial psychology. In the case of Kalanick, I’d summarize it as follows — he has a certain public image that some don’t like (I don’t know the guy at all), but I do recall an interview he gave over three years ago where he talked about some of his previous companies and those associated struggles. Listening to Arrington, my memory was triggered, so I listened to this long interview [video link] while making dinner tonight. And, it was fascinating to hear Kalanick talk about himself and Uber way back in early 2011. Here’s what I took away from both discussions:

Uber is Kalanick’s 4th Company. He started an SAT prep company, then Scour, then Red Swoosh, and then Uber. He was a serial entrepreneur before starting Uber. I’d bet many folks in tech didn’t know that. I knew about Red Swoosh, but not the others. Interestingly, all but the SAT company were based on P2P relationships and technologies. One has to wonder how deep his intuition around P2P networks was before he started Uber.

An Edgy Chip On The Shoulder: Many folks have chips on their shoulders. Whatever the psychology, folks have to manage it in order to carry on. Kalanick’s chips come from having a failed startup which was sued, and then another where he didn’t pay himself for four years and was living in his parent’s house. (By the way, I’m taking this from the interview in 2011 and this past week.) I imagine it’s hard not to be so aggressive and competitive after having such experiences, and people respond differently to such pressures.

The Uber Killer Is Stress. Speaking of pressure, when Arrington asked Kalanick what could kill Uber, the CEO mentioned “Stress.” The company just hired David Plouffe who orchestrated one of the greatest political campaign in politics, and now has work cut out for him as he grooms a company and CEO to engage in global battles with car industries, city governments, organized labor, upstart companies, and even nations (laws in Germany, fierce competition in China). When I looked at the interview from 2011, I noticed Kalanick’s hair was jet black; today, he has some prominent grey streaks, just like a weathered politician in the klieg lights.

Benchmark’s Series A Call Is The Stuff Of Legends. In 2011, Kalanick retells how, after pitching the entire Benchmark partnership (his only meeting with them), the team asked him to wait and had one of their colleagues sit with him so he couldn’t leave. They deliberated and decided on the spot, and then invited Kalanick back in to do the deal. At the time, Uber was in only two (2) cities! Moreover, in this 2011 interview, Kalanick discusses other things Uber can do — a slew of “on-demand” services (his words) like food, jets, and whatever else people order. Even in this interview, Kalanick is thinking about Uber on a scale similar to Google.

The Traveling Salesman Problem In Computer Science. Kalanick refers to this toward the end of the 2011 interview, essentially explaining a routing optimization problem that has 15 or more nodes getting so complex, even computers couldn’t crack the code. In those types of discussions, you realize Kalanick is not kidding around when talking about math (1580 SAT) and his knowledge of how computers work (CS degree). He is a businessman and salesman on the outside, but within, something else lurks. You can start to see how this “Traveling Salesman” problem may apply itself as Uber experiments with services like UberRush, Corner Store, UberPool, and the extension of its API across the greatest technology market (mobile platforms) we have ever seen.

Most of all this is known already and has been covered fairly well. But, the dots connected for me in a different way this evening. Kalanick and Uber are already quite a powerful force, but when one digs deeper into the elegant simplicity of Uber’s model and the motivational drive of its CEO, you begin to wonder — just how big can this get? What can stop it? What other CEO is psychologically tuned this way and adept in so many interdisciplinary dimensions?

Haystack is written by Semil Shah, and is published under a Creative Commons BY-NC-SA license. Copyright © 2018 Semil Shah.

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