On being an asshole

Here’s something you didn’t know about me: I’m vaguely claustrophobic. It doesn’t mean much in practice, but when I was at the last TechStars demo day at Webster Hall, I watched the presenters from the same place I watched the Beastie Boys in 1985, the Mountain Goats in 2008 and every concert in between–the back left, right near the door, the stairs, and close enough to the outside to make it tolerable.

It’s a little different in the back. Fred Wilson and Brad Feld are right up there in the front row representing, while us riff-raff are standing by the bar wishing it was open. I like the back row. My best friends from college are the ones I met sitting in the back row. When David Soloff came to talk to my class at Columbia, he paused a few minutes into his profanity-laced tirade about entrepreneurship to poll the class: who was uncomfortable with his swearing? Several hands in the front row went up. Who thought it added to the discussion? Several hands in the back row went up.

Some of the people in the back row are the studied cool. But some others are the actually unenthusiastic. The back of demo day was no different. On one side were people like Andy Weissman, Chris Wiggins and Taylor Davidson, all trading notes on which founders we found particularly awesome, who already had funds committed, the amazing amount of progress some teams had made during that session of Techstars, and, in general, gratefully soaking in the condensed learning of months of hard work by talented and smart people.

On the other side of me were a group of people loudly telling each other how ridiculous the ideas were, how the companies were going to crash and burn, how stupid and sheeplike the investors were for giving them money, etc. You know what they were saying, because our ecosystem is flooded with this type of talk. We see it every week in the tech press when some formerly high-flying company starts to falter. We see it every day in the comments on Hacker News. We hear it when we have coffee or drinks.

And it’s not just envious wannabes saying these things. I’ve heard venture capitalists, big company executives, startup employees, lawyers, angel investors, students, and professors bash entrepreneurs. Every sort of person except other entrepreneurs.

Chris Dixon said there are two types of people in the world: people who have tried to build a company and people who have not. This ruffled the feathers of people I know in the innovation community who have never been an entrepreneur because it implies that those who haven’t been entrepreneurs should just shut up and sit down. That’s not exactly right, but it is true that people who have been through the process of trying to start a company do not, as a rule, engage in destructive and pointless criticism of other entrepreneurs. Not that non-entrepreneurs all do, just that entrepreneurs don’t.

There’s a difference between criticism and critique. One is destructive, the other constructive. Entrepreneurs who have been through the grinder, who have been “dismissed by arrogant investors who show up a half hour late… having pundits in the press and blogs who’ve never built anything criticize you and armchair quarterback your every mistake” (as Chris puts it) don’t then turn around and do that same thing to other entrepreneurs. Because they know from experience that it’s pointless and results in pointless pain.

The people who call entrepreneurs stupid, who bludgeon them with their mistakes and try to humiliate them in public rationalize it by saying “we’re being direct, open and tough–just like the real world.” They are egregiously wrong. That’s not the form that either education or motivation takes in “the real world.” Unless by real world you mean our schools or government where the highest goal is creating the conformity needed to staff middle management at our large industrial age corporations. Entrepreneurial zeal does not survive that.

I once asked a Swedish founder what the difference between starting a company in Sweden and in the US was. He said that in Sweden there is a saying: “the tallest poppies have their heads cut off.” Those who are outstanding will be cut down so they no longer stand out. He believes this attitude prevents many Swedes from deciding to strike out on their own. I wish this were particular to Sweden (no offense)–or to any one place that wasn’t here. But it isn’t. It’s not even a Swedish saying, it’s a universal one. It’s first recorded use is in some of the first recorded history, Herodotus. The context then was to enforce a more homogeneous community in order to better control it. This is still its use now. This attitude is the absolute antithesis of what we are trying to do in the entrepreneurial community. We are not cutting the heads of the tall poppies, we are letting a thousand flowers bloom, praying that one of them will be taller than all the rest so we can then plant its seeds and someday all the poppies will be tall.

If you’ve been through the pain of starting a company, you know that criticism is entirely useless. If you haven’t, and you find yourself in the back of demo day wanting to cut down the people brave enough to have made it up onto the stage, you need to think hard about it. Think about the difference between criticism and critique. Think about the difference between extrinsic and intrinsic motivation and how entrepreneurship is predicated on the latter–the carrot, not the stick. Think most of all about whether what you are doing and saying is helping founders succeed, even if their success is not something you will be part of. Because if you don’t believe that their success helps us all, no matter whether we are involved in it or not, then you are in the wrong room.

At least you’re near the exit.


  1. Jerry – this is exactly right. The act of creating something from scratch is chaotic, energetic, passionate, frightening, angst-ridden, euphoric, and incredibly incredibly incredibly hard. The assholes have no idea. No idea of the sacrifice that comes with starting anything from scratch. No idea how painful their comments can be. No idea how hard it is to push through the down times. I once had a CEO brought in to “lead” a startup I had created laugh and say sarcastically, “I have no idea why someone would start a company – it’s so much easier to show up and run it later.” And yes, he was an asshole.

  2. Thanks for this honest post. As a corollary, I find that I’m most disappointed when a fellow founder engages in criticism rather than critique. This rarely happens, but when it does, it really does sting.

  3. I’ve always thought dealing with assholes is some sort of right of passage for testing the mettle of an entrepreneur. Actually, it’s a right tof passage for life too. Most people you meet with power are jerks. It’s the rare exception to find someone in a position of power that handles themselves with class and dignity.

    But I’m going to challenge the notion that “criticism in entirely useless.”

    Many successful people have used criticism as a motivational tool to succeed. History is littered with stories of the guys who were told they were “too small to play in the majors” and used that as motivation. There’s nothing wrong with having a chip on your shoulder. Entrepreneurs by nature MUST prove people wrong and if I was a VC, I would be looking to invest in just those people.

  4. Jonathan–

    You’re right, but it’s a bit like your dad beating you so you can learn how to take a beating, isn’t it? It might motivate you to be a big man, but I still disagree with it.

  5. Great post. If success in an idea/venture was obvious, someone else would have already done it. As a former intrapreneur, the ‘assholes’ you mention remind me of ‘corporate antibodies’. Yea, they can be assholes, but sometimes they are well meaning folks perpetuating corporate innovation incompetence, which fortunately leaves many opportunities wide open for true entrepreneurs to capitalize on.

  6. @Jim

    Yes. I don’t think they are bad people, just misguided. In some environments you can succeed by applying extrinsic motivation because you will always be there to continue the extrinsic motivation. The armed forces, corporations, any hierarchical organization, really.

    But founders need to have the intrinsic motivation to get things done. Otherwise they’re just employees.

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