Asshole assholes: They suck at work and everything else. These are the mean, jealous, insecure jerks who you’d avoid at a party, but who inevitably sit immediately next to you at the office. They cannot deliver, are deeply unproductive, so they do everything possible to deflect attention away from themselves. They will lie, craft gossip, and manipulate others to get people off their scent. The only good thing about these assholes is that they’re generally out the door pretty quickly—they can only deflect for so long before people start noticing that they bring zero value. And nobody likes working with them.

Mission-driven “assholes”: The people who are crazy passionate—and a little crazy. They speak most frankly, trampling the politics of the modern office, and steamroll right over the delicate social order of “how things are done around here.” Much like true assholes, they are neither easygoing nor easy to work with. Unlike true assholes, they care. They give a damn. They listen. They work incredibly hard and push their team to be better—often against their will. They are unrelenting when they know they’re right, but are open to changing their minds and will praise other people’s efforts if they’re genuinely great. A good way to know if you’re working with a mission-driven “asshole” is to listen to the mythos around them—there are always a few choice stories floating around about some crazy thing they’ve done, and the people who’ve worked with them closely are always telling everyone that they’re not that bad, really. Most tellingly, the team ultimately trusts them, respects what they do, and looks back at the experience of working with them fondly, because they pushed the team to do the best work of their lives.

It’s the assholes who are focused on people—on controlling people—who make work miserable. Real assholes always make it personal. Their motivation is their ego, not the work. As long as they’re winning, they don’t give a shit about what’s happening to the product or what the customer has to deal with. These are the assholes who make it progressively more difficult to create something you’re proud of.

She rolled her eyes and completely ignored his order. But she had to deal with this guy to get her project shipped. So she did the only thing you can do when faced with a controlling asshole:
Kill ’em with kindness.
Ignore them.
Try to get around them.

Political assholes thrive in large organizations where they can pull the kind of Machiavellian BS that makes you sound crazy and paranoid when you’re describing it. They find people who aren’t exceptional at their jobs and protect them in exchange for their allegiance. They get dirt on their peers—who’s having an affair with his admin? Can we get HR to cover it up?—then those people are indebted for life.

That’s when your team needs to have a counternarrative. The bullshit-asymmetry theory, Brandolini’s law, will be at play here: “The amount of energy needed to refute bullshit is an order of magnitude higher than to produce it.”

I’ve seen way too many people come out of the corporate world, decide to start a company, and be completely unprepared for what it takes. If they’ve never been on a small team starting from scratch, they’re often a fish out of water. They spend too much money too fast. Hire too many people. Don’t put in the time, don’t have the startup mentality, can’t make hard decisions, are buried by consensus thinking. They end up making mediocre products or nothing at all.

Steve Jobs was clear about the lesson he’d learned and made sure we all learned it, too: any company that tries to do both B2B and B2C will fail.

My dad was on commission but he would often sacrifice a sale in order to build a personal connection. The best salespeople are the ones who maintain relationships even if it means not making money that day.

To be clear, I fully support massages. I love massages. I get them all the time. Everyone should get massages. But at no point should your company culture be formed around the idea that massages are your due. At no point should you promise employees that they’ll get massages forever. At no point should perks define your business or drag it down.
Perks are frosting. High-fructose corn syrup. And nobody will begrudge you a little sugar—everyone likes sweets from time to time. But stuffing your face full of them from morning to night isn’t exactly a recipe for happiness. Just as dessert shouldn’t come before dinner, perks shouldn’t come before the mission you’re there to achieve. The mission should fill and fuel your company. The perks should be a sprinkle of sugar on top.