Infinite entrepreneurship

A lot of startup founders I talk to approach entrepreneurship as a finite game. The historian James Carse coined the term in the 1980s:

“There are at least two kinds of games. One could be called finite, the other infinite. A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play.”

The finite game of running a startup usually goes something like this:

1. You start working on a product with the potential to change the world (or at least make you a lot of money).

2. You raise funding from investors on this hope.

3. You work like hell to build and grow the product to the point where it might satisfy the conditions for "winning" — typically, going public with a juicy valuation or getting acquired by another company.

And if you don't win in this way? You lose. (Unless you're Sahil Lavingia, whose investors sold their ownership back to him for $1 after the company failed to reach its revenue targets.)

The game often changes when you remove outside funding from the equation. [1] I hardly ever hear bootstrapped founders discussing aspirational goals for walking away from their businesses. They don't want to walk away. They build projects for fun on the weekends. They read "lifestyle business" books like Company of One, Start Small, Stay Small, and It Doesn't Have to Be Crazy at Work. And they experiment with work policies like never scheduling meetings and avoiding project deadlines — at least in the case of Sahil Lavingia himself (post-funding).

In other words, infinite entrepreneurs focus on ways to enjoy the process — and not just the proceeds — of running a business.

This is a mindset shift that does real work in the real world, because changing what you aim at changes what you see. It's the difference between planning to compete for first place in a long-distance foot race and deciding to become a runner. Or between training to bench press 200 pounds and deciding to become a person who's physically fit. In each case, the second approach will tend to result in much more durable and enjoyable lifestyle changes.

One of the most influential infinite entrepreneurs of our time is Scott Adams, the cartoonist behind the popular comic Dilbert. You'll probably never encounter a founder with more entrepreneurial stamina than Scott. Among the many failed ventures he names in one his books are a velcro rosin bag, a meditation guide, multiple space-themed computer games, an app for measuring people's psychic abilities, a file-transfer product, a website dedicated to crackpot ideas, an online-video sharing app, a grocery-delivery service, a manila folder product with a pouch to hold floppy disks, a service that embeds ads in online calendars, multiple restaurants, a keypad technology for phones, and dozens more. His comic Dilbert, he says, "started out as just one of many get-rich schemes I was willing to try."

How did Scott keep going through all of those failures? And how, for that matter, has he found the continued motivation to make new products, write new books, and reinvent himself many decades after the wild success of Dilbert? You already know the answer if you've been paying attention: by practicing infinite entrepreneurship in the form of a relentless focus on systems instead of goals. [2] But Scott himself expresses this a little more bluntly:

“Goals are for losers. For example, if your goal is to lose ten pounds, you will spend every moment until you reach the goal — if you reach it at all — feeling as if you were short of your goal. In other words, goal-oriented people exist in a state of nearly continuous failure that they hope will be temporary. If you achieve your goal, you celebrate and feel terrific, but only until you realize you just lost the thing that gave you purpose and direction.”

Yeah yeah, all of this sounds really good on paper, but the inconvenient fact is that entrepreneurship is incredibly difficult. Most businesses fail soon after starting, and many don't ever make a dime. But founders have bills to pay — and they don't have an infinity of time in which to pay them. So you might reasonably object to infinite entrepreneurship on the grounds that even if an infinite entrepreneur doesn't play the startup game in order to "win," they can still "lose" by running out of money.

But I actually find this to be the strongest case in favor of the infinite mindset. Because money isn't the essential resource that fuels entrepreneurship. Motivation is.

Yes: entrepreneurship really is one of the most difficult endeavors around. Founders don't get to just be good at the one thing they're already good at — writing or coding or sales or managing personalities, etc. They have to be proficient all around. Especially in the early days of a project. And as with any kind of career capital, developing this proficiency takes time. Often a lot of time. So an infinite mindset prepares you to put in the years of work it might take to reach the sorts of milestones that get recognized as "business success" (like generating sustainable profits).

This point about time doesn't get discussed a lot in Silicon Valley. I think the reason for this is that VCs, who exercise a lot of indirect influence over tech publications and startup culture, aren't generally interested in what it takes to become a good founder. They're interested in founders who are already good.

So founders themselves would do well to pay less attention to "startup culture" and take the long view. Infinite entrepreneurship could mean staying at your day job a while longer — or even indefinitely — before going all in on your business. It could mean reaching out to an established founder and offering unpaid services in exchange for learning how they operate. It could mean learning to ship free projects to a given audience before trying to ship paid products. [3]

But whatever you do, ignore stories about college dropouts building unicorn startups. Ignore those who insist you have to reach this or that milestone by age 30. And never take it for granted that "successful" founders featured in the news are as happy as they let on in their cover stories. I know dozens of these people personally. Hedonic adaptation ensures they're usually no happier after succeeding than they were before. And when they are, it's usually because they've found ways to keep playing.

Footnotes:

[1] There's probably only a loose correlation between how a business is funded and which kind of game its founder plays. Many venture-backed founders land big exits and then become serial entrepreneurs, and many bootstrapped founders chase exits of their own. (After all, we sold Indie Hackers to Stripe.)

Still, I'm happy to stick with this generalization because it seems to accurately represent the value differences between people in high-growth startup circles vs people in bootstrapping circles.

[2] The systems-versus-goals mantra seems ubiquitous among entrepreneurs these days (largely thanks to the massive success of James Clear's Atomic Habits, which was partly inspired by Scott Adams), so it's worth clarifying that Scott Adams himself defined the distinction between a "system" and a "goal" this way:

For our purposes, let’s say a goal is a specific objective that you either achieve or don’t sometime in the future. A system is something you do on a regular basis that increases your odds of happiness in the long run. If you do something every day, it’s a system. If you’re waiting to achieve it someday in the future, it’s a goal.

[3] Nathan Barry's article on the ladders of wealth creation does a good job illustrating what this sort of climb might look like, both in theory and in practice.