The second wolf

Let me know how I can help myself.

Inside every venture capitalist there are two wolves.

The first loves to learn. They have the best job in the world, they tell themselves, because they get to work with so many smart and driven people. They never meant to become a VC, but now that they are, they can’t imagine doing anything else. They want you to let them know how they can be helpful, and they genuinely mean it. They miss their days in the trenches: They want to roll up their sleeves and review product mocks, brainstorm about the new marketing strategy, and work through customer objections in the sales team’s deal review. They admire startups’ grit, founders’ creativity, and are grateful for the work of the talented teams that work so hard to make them money.

The second wolf believes they could do it better themselves. They think the first wolf is VC Manager Mode: Gentle outsourcing, and hoping that startups figure out on their own what the second wolf knew all along. They think the friendly builder is a useful brand, but their real heroes are the ruthless killers: Larry Ellison; Frank Slootman; Gordon Gekko; Jordan Belfort. They want to be remembered as hard truth tellers; they want to write the next “RIP Good Times” memo; they want to be feared as much as loved. They want to be Jeremy Irons in Margin Call, and they hope their speech gets leaked. They think the CEO is screwing things up, and that the solutions are obvious—a sharper pencil, a tighter belt, a deeper cut—but the CEO doesn’t have the backbone to do what needs to be done. Back in their day, the kids these days wouldn’t have made it.

For the second wolf, it’s about money—but it’s mostly about optics. Because the second wolf is insecure. Their GSB classmate just made the Midas List, but everyone knows that’s just pay-to-play PR, right? They’re on a board with a partner from Sequoia, and they’re not that impressed. They’re jealous that they weren’t invited to the All-In Summit; they’re secretly happy that Bill Gurley and Brad Gerstner’s podcast hasn’t really taken off. They tell themselves that they’d have a bigger following if they wanted to, but they care about building. They prefer to keep a low profile; to be heads down; to do the work, helping founders, adding value. They’re thinking about launching a newsletter. 

The second wolf will shiv you for a dollar. They will shiv you to show off for their friends. They will shiv you to remind you that they can. They will shiv you because their other investments are struggling, because their senior partners are whispering about their performance, and because they think your shivved scalp will impress their bosses. The first wolf will say this is the worst part of the job, and they are doing what they have to do for their limited partners. The second wolf will shiv you for the thrill of the shiv. 

Inside every venture capitalist, there are both wolves. Nobody is singular, nor does a company or CEO need one type of advice. Sometimes, there are opportunities, and you need a collaborator to help chase them. And sometimes there are problems, and you need the second wolf to solve them. You need tough love; stern feedback; a stick to fear, rather than a carrot to hope for.

But I will say this: Nobody is as good of an actor as they think they are. You can smell when someone is cosplaying a character from a blog post, or when they’re preening for someone else in the room, or when they’re panicking about their own job because they don’t know what else to do. You can tell when the confidence is fake, or the bloodlust is real. You can tell when someone is desperate to prove that they’re useful and not just rich.