Getting away with it

Fine, fOuNdEr MoDe.

At some point shortly after I started working in tech, I once asked a coworker if it was possible for us to build some part of a website in a particular way. He told me of course it is; it just depends on how much time we want to spend on it. It was a computer, he said; we can make whatever we want. 

What a silly thing to say, I thought.

But over the years, as I started to learn how to write a little bit of code,¹ I realized his answer wasn't pithy, but profound. As long as you stay within a few broad boundaries, you really can make whatever you want. There is no feature that is impossible to build; there is no dream design that can only be imagined; there is no div that can't eventually be centered. There are common patterns, and there are simple paths of little resistance, but there are almost no rules. We are far more constrained by our own sense of comfort—both in what feels familiar and in how much we’re willing to risk to try something new—than an actual leash. Computers don’t tie us down; we do. 

Such is life. We drop our own anchors. We get settled into our ways; we follow the paths that others suggest to us; we explore our neighborhoods, but not the foreign countryside that we can’t immediately see. When we leave a job to “pursue other interests,” those interests are usually small variants of what came before: Not SaaS, but B2B! Not a large tech company, but a small one! Not a designer, but a PM! Either explicitly or through the blinders we put on ourselves, we develop fences for ourselves—our shoulds and shouldn’ts, our cans and won’ts; the identities that are us, and the ones that we can’t pull off. 

Professionally, these prescriptions can be especially potent. Not only does it feel like we can get punished for breaking them, but it also feels like we get rewarded for following them. There is always a promotion two review cycles away. Play by the rules, and someone will invite you onto the next rung up the corporate ladder. Deviate too much—by doing something unconventional, or by trying to vault yourself to another ladder in some distant field—and you risk falling. 

Silicon Valley fancies itself as thinking differently. It’s for the crazy ones, the misfits, the rebels. It’s for “thinking from first principles.” It’s for people who want to play their own game, and who, both metaphorically and literally, see a computer and think, we can make whatever we want. 

But, for better or worse, Silicon Valley is not so much a place with no expectations and norms; it just has its own version of them. There is a corporate ladder here too, and a playbook for how to climb it. Look for rocket ships.² Start a company. Run it by axiomatic motto: Move fast and break things; make stuff people want; iterate; disrupt; have strong opinions that are weakly held. Our rules are insurgent, but they are rules, and they are also hard to break.³ 

This week, Paul Graham gave us another one (if you’ve used the internet for the last week, you’ve already read all this):

…the conventional wisdom about how to run larger companies is mistaken. As Airbnb grew, well-meaning people advised [Airbnb CEO Brian Chesky] that he had to run the company in a certain way for it to scale. Their advice could be optimistically summarized as "hire good people and give them room to do their jobs." He followed this advice and the results were disastrous. So he had to figure out a better way on his own, which he did partly by studying how Steve Jobs ran Apple. So far it seems to be working. Airbnb's free cash flow margin is now among the best in Silicon Valley. …

In effect there are two different ways to run a company: founder mode and manager mode. Till now most people even in Silicon Valley have implicitly assumed that scaling a startup meant switching to manager mode. But we can infer the existence of another mode from the dismay of founders who've tried it, and the success of their attempts to escape from it. …

Look at what founders have achieved already, and yet they've achieved this against a headwind of bad advice. Imagine what they'll do once we can tell them how to run their companies like Steve Jobs instead of John Sculley.

There are two ways to read this: One pithy, and one (reluctantly) profound. The first—and the way that it seems to be getting digested by much of the internet—is that founder mode is itself a new set of rules. Rather than having a few direct reports, have a bunch. Rather than delegating, stay involved. Someday, someone will write a viral “Manager Mode/Founder Mode” blog post that lists out the poles of each: Manager mode is a bureaucratic tar pit created by pinheaded pencil pushers with email jobs. Founder mode is using a machete to cut through red tape. Manager mode is scheduling a blameless retro. Founder mode is solving a problem. Manager mode is Office Space. Founder mode is Logan Roy fanfic. 

This version—founder mode as a vibe—probably isn’t very useful. It is yet another cliche that, though perhaps not necessarily wrong, provides no practical guidance on how to actually navigate managerial challenges. It is a headline, a pull quotes, a bulleted listicle, packaged into bite-sized tweet or podcast soundbite that is designed to be consumed by inexperienced executives in the back of an Uber.⁴ Examples of how to put these ideas into practice, the complicated nuance behind applying them in real-life situations to real-life people, and the exceptions that reveal that they’re not irrefutable laws of startup leadership do not fit into the meme.⁵ Founder mode is not advice; it’s something to yell when you bulldoze into a meeting and make the decision yourself. ⁶

There is a broader way to interpret Graham’s post, however: It is a reminder that there are no rules.⁷ The point is not to copy Steve Jobs, and to run a company the way he ran his; that is, after all, the antithesis of thinking differently. The point is to be inspired by Steve Jobs, and to come up with your own way of doing it. It is to stand on the ledge before an infinite pit of options, and, despite the dizzying vertigo, finding conviction in something. It is to move to the music without worrying about whether other people think your dancing is good or bad. Hosting an annual retreat for 100 people because that’s what they do at Apple isn’t “founder mode;” it’s cargo culting.

This, of course, is hard to do. We love tactical advice and key takeaways. Startups are hard because they are broken machines and we often don’t know what to do to fix them. Instructions would be nice. That could be big retreats, or staying involved in customer support conversations, or personally approving every product update. Or it could be the opposite of all of those things—which, at the rate we’re going, may become as counterintuitive as Jensen Huang having 60 reports seems today. But founder mode is not the answer to that question; it is simply permission to look for a solution. The rest of the problem is up to us.

Anyway, the best summary of all of this​​, and how it seems like it will manifest itself in the real world, is from comedian Anthony Jeselnik:

All these comics now, it's almost like the point is to get in trouble. It's like, "Why are you giving me shit? I'm a comic, I'm allowed to say whatever I want." That's wrong, as far as I'm concerned. People think as a comic, your job is to get in trouble, but they don't want to get yelled out. Like it's ok to make people mad, but they don't want any pushback, and I think that's wrong. 

As a comedian, you want to make people laugh. There's a quote attributed to Andy Warhol that I love: "Art is getting away with it." If you put out a special, and everyone's pissed, you didn't get away with it. You need to make everyone laugh, so that they're like, "Yeah, he talked about some fucked up stuff, but we're all happy." That's art. Otherwise, you're just a troll.

Founder mode—and really, leadership, but that’s harder to brand—is the same thing: It is doing something daring and getting away with it. That is why Steve Jobs is Steve Jobs—not because he thought differently, but because he did something bold and it worked. The second thing is more important than the first.

And that’s a mode that anyone can operate in. There is a curious line in the final footnote of Graham’s post, when he says his advice could get abused by “managers who aren't founders will decide they should try to act like founders.” The implication, it seems, is that founders—because they are the company’s “parent,” and because they know its history—have permission to color outside of the lines, whereas other people do not.⁸ 

Superficially, sure. But, while founders might have more default permissions than other employees, everyone is ultimately governed by one law and one law alone: You can do it, if you can get away with it.

1. Marvel at what I can do. 

2. A good one or a bad one will do.

3. Imagine, for example, a startup that tried to run itself in a more “traditional” way—say, with a strong sense of hierarchy and strict chain of command. It would get much weirder looks than some hundred-year old conglomerate that uses standing desks and Notion.

4. One VC firm literally produced minute-long podcasts of management advice.

5. Notably, Graham says that some “founders who are unable to delegate even things they should will use founder mode as the excuse.” For an essay that mostly tells people to delegate less, that caveat is doing a lot of work. 

6. Founders who only do this occasionally are operating in quarter founder mode. Those who do it nicely are operating in quarter founder with please mode. BetterUp is operating in royale mode.

7. I’m not sure if this is the point he was trying to make or not, but it’s the one I like.

8. Earlier in the post, he says that managers are often “professional fakers” who “drive the company into the ground,” so they’re really damned if they do, damned if they don’t. You can be a founder or you can be a problem, I guess.