Are you a leader or a psycho?

Where is the boundary between visionary and scary?

I got a request from Neil to do a newsletter on leadership, so here I am, ready to do some Thought Leading. (By the way, requests on topics are always welcome either by Twitter DM or email so the newsletter is not just you suffering through what I think are my choiciest joke tweets.)

One of the topics I’ve been thinking about around tech leadership lately is: how do you know whether you’re a really good leader, or just a psycho? There seems to be a really thin line between success and being a sociopath, and they didn’t exactly teach us where that line was in my MBA program (maybe it’s because I didn’t go to an Ivy.)

Here are some examples: Steve Jobs - brilliant thinker, terrible human being. There are plenty examples of this, including the time he went to Whole Foods with Jony Ive and went all out on a woman making a smoothie,

Once we went to Whole Foods market to get a smoothie ... And this older woman was making it and he really got on her about how she was doing it." Jobs later felt bad realizing she's an older woman doing a job that she's not happy at.

The recent book Small Fry, by Jobs’s daughter Lisa, which I have not yet read because I don’t want to fall into a depression, also details how terrible of a father Jobs was.

But, Creativity, Inc. , a behind-the-scenes look at what makes Pixar successful, Ed Catmull, the co-founder of Pixar Animation, talks about his encounters with Steve Jobs this way:

For many people, changing course is also a sign of weakness, tantamount to admitting that you don’t know what you are doing. This strikes me as particularly bizarre—personally, I think the person who can’t change his or her mind is dangerous. Steve Jobs was known for changing his mind instantly in the light of new facts, and I don’t know anyone who thought he was weak.

To be sure, Catmull devotes many pages to how hard Steve was to work with, how much stress and uncertainty he caused for the flailing Pixar company, and how they didn’t get along, but in the end, both Pixar and Apple became, ultimately, enormous, successful companies.

So - was Steve an asshole, or a genius? Both. But, because Apple has been successful, more of the latter. If he was just some random middle manager in Oklahoma, his obituary would probably just read that everyone hated him as soon as he came into the office on Monday mornings. Success and money tend to have a way of obscuring some of the hideousness of human nature.

In the recent bestseller Bad Blood (which is just as juicy and as much of a trainwreck as everyone says and you should absolutely read it), Theranos CEO Elizabeth Holmes tries to pick up where Steve Jobs left off - wearing black turtlenecks, deepening her voice (it really is insanely bizarre the first time you hear it), and driving at a sexy product vision, the only difference being that she is iterating on hardware that people depend on for healthcare diagnoses, not making prototype phones and computers.

Through a series of insanely increasingly bizarre events, she was finally exposed, and settled out of court. Theranos dissolved in 2018. But, before that, the company only ever got positive press, from New Yorker profiles, Henry Kissinger, partnerships with Walgreens, and much, much more, including endorsement from David Petraeus. While all of this was going on in the foreground, the machine to conduct the actual blood tests was nowhere near built, people were quitting the company, and the atmosphere was severe.

Reading Bad Blood, it’s easy to shout from the couch, “Was Holmes stupid or delusional? Why did she feel the need to lie or cover up what was going on? Why didn’t she just tell the truth or change the company’s course of action” And the answer to that is, she had external validation. As long as people kept taking meetings with her, the world kept spinning.

And I think that’s the crux of the matter in leadership: As long as you’re getting external validation, and no one in your inner circle is saying no to you, why should you stop your trajectory? Why should Steve Jobs have stopped being an asshole? According to history, he shouldn’t have. Elizabeth Holmes, if she had kept on going, might have struck on an actual innovation, too. And then what would history think of her? Not as an insane deep-talker who conned an entire industry, but a trailblazing woman who persevered.

Another, final case in point I want to talk about is Phil Knight, the ex-CEO of Nike, and the author of Shoe Dog, the Bad Blood of a couple years ago. If you don’t read any of these other books, please read Shoe Dog.

It’s an amazing book, because Phil turned out to be a very good writer, but mostly because it was impossible for me to believe that he willingly bragged about what an asshole he was in an autobiography of his life. I hope I’m not spoiling anything by revealing that he massively screwed over his co-founders on stock options, tricked the company he was working with in Japan on importing their shoes into the US, and paid the woman who came up with the Nike logo $15. It’s been a while since I finished the book, but this is what I just remember off the top of my head.

If you don’t believe his take, please continue to follow-up by reading the equally excellent University of Nike, which covers some of the same ground as Shoe Dog, but focuses on his relationship with the University of Oregon, how Nike, under his direction, pushed for sports at universities to be sponsored by companies in lieu of the lack of public funding, and much, much more. (Spoiler alert: He holds the father of daughter with a rare illness hostage over money to fund that illnesses research foundation. Yup.)

But for Holmes, Jobs, and Knight, to question any of these decisions would mean insanity: they were doing things right. Why should they change?

If the stock price is going up, why should anyone change? If they’re successful doing the things they’re doing, even if those things are crazy, immoral, or bad, what’s the incentive to do differently, forsaking everything in the name of immortality? Where was the reckoning for Travis Kalanick (who has a new startup now), or, even more recently, Zuck, who is, and will be the leader of Facebook for the far, far forseeable future.

That’s a moral exercise left to the reader, and I don’t have any answers, but it’s something I think about all the time - how do you know you’re going to where you need to go, and not stepping on people along the way?

Art: Autoportrait en homme surpris et terrorisé (1791), Joseph Ducreux


  1. Slava has an alarmingly accurate thread about the different stages of drunkenness in Russian:

  2. This book about how to advocate for yourself in the Augean nightmare labyrinth that is the American healthcare system looks really good

  3. Good thread from Jacqueline about tradeoffs of R in production settings

  4. Alex keeps dropping hits in One-Shot Learning, including an interesting new paper on data validation

  5. Insane story about how a local Philly bar got its name, Khyber Pass

  6. Richard writes in Cybercultural, “The best deep dives - whether in podcast or blog format - add to the experience of watching a tv show or movie in 2019. It becomes more than just a tv show to binge on Netflix and then forget about; it’s now something to think through and perhaps talk about with other people.”

About the Author

I’m a data scientist in Philadelphia. Most of my free time is spent kid-wrangling, reading, and writing bad tweets. I also have longer opinions on things. Find out more here or follow me on Twitter.

If you like this newsletter, forward it to friends!