Infinite Entrepreneurship – A Philosophy for Work and Life

A game you keep on playing becomes a gift that keeps on giving.

Entrepreneurship is ostensibly about value creation, strategy, decision making under uncertainty and a host of other narrow, business-esque factors. Sure enough, but it can also be viewed through a more holistic, philosophical lens, if one considers entrepreneurship as a broader, all-encompassing lifestyle choice for certain people with certain proclivities.

I happen to have a philosophy on the notion of entrepreneurship as a lifestyle choice which can be summed up in six short words: “stay alive, and keep making bets”. Ernest Hemingway would be proud. Before I explain the link between staying alive (no, that’s not a Bee Gees reference!) and entrepreneurship, let me first introduce you to an old theologian called James. 

Introducing Finite and Infinite Games

A somewhat obscure religious scholar named James Carse wrote an excellent book called “Finite and Infinite Games” in the mid 1980s.

Finite and Infinite Games: A Vision of Life as Play and Possibility by  James P. Carse

In this book, he argues convincingly that everything we do in life can be seen as game – the career game, the love game, the status game, the football game, the learning game and so on.

He then lays out a brilliant framework for distinguishing between two distinct types of games, which are fundamentally different in terms of rules, ideal outcomes, types of players and duration of play.

finite game is any game with clear, predefined rules, a set start and end time, known players and a mutually agreed-upon outcome. The point of a finite game is to win the game within its defined parameters, leaving the other players as losers. Think soccer, tennis, rowing, chess or ludo as examples. 

Infinite games on the other hand, are more complex. In these games, the rules are vague, subject to change and open to different interpretations from one player to another. There is no defined end point, there are no winners and losers, and even defining who the players are can be difficult. Furthermore, and most importantly, the goal of a player in an infinite game is not to win the game, but to keep on playing. 

Some examples of infinite games are life, evolution, your marriage, your health, and your journey of self exploration and personal development. Think about it – there are no “winners” in your marriage. The game of your own health has no end point, the goal is to keep the game of good health going for as long as possible. Your life cannot be “won” according to a universal set of rules, leaving everyone else as losers, because all players in the game of life are free to choose their own rules and success criteria to play by.

“Finite players play within boundaries; infinite players play with boundaries.”
– James Carse

So, you may ask, what has this got to do with entrepreneurship? To answer that question, let us consider two distint types of players of the entrepreneurship game.

Finite and Infinite Entrepreneurs

Some entrepreneurs are only in the entrepreneurship game for their current case, startup or business opportunity. If or when their current company either fails, IPOs or gets acquired, they intend to quit the entrepreneurship game and do something else (golf, typically). These entrepreneurs play a finite game which started with their idea, and will end when it reaches either failure or some predefined notion of success. That will be the end of it.

Other entrepreneurs are playing an infinite entrepreneurship game. These are often called “serial entrepreneurs”. When their current company either fails or succeeds, they will move on to the next one, then the next one after that, and so on. They are in the game forever.

They are committed to the path, the principles and the lifestyle of entrepreneurship, but they are “case agnostic” – they can take their entrepreneurial drive and tendencies elsewhere and apply it to other cases, other startups, other problems to solve. These people are infinite entrepreneurs. 

For infinite entrepreneurs, there is no defined “end game” if you look at a long enough time horizon. Sure, their current company might have an end game, such as an exit, an IPO or to hit some kind of KPI target, but this merely represents a finite game within the infinite game of entrepreneurship for life. 

“Finite games can be played within an infinite game, but an infinite game cannot be played within a finite game.

Infinite players regard their wins and losses in whatever finite games they play as but moments in continuing play.”

–James Carse

Stay Alive and Keep Making Bets

Lets us now return to my six-word entrepreneurship philosophy mentioned at the beginning of this post.

Since infinite entrepreneurs are playing a game where the goal is not to win, but rather to keep playing the game, it makes sense to “stay alive, and keep making bets”.

The practical, day-to-day meaning of this short statement is clear: when making choices, prioritise first and foremost to stay alive, and secondly to make bets on ideas, startups, products, services or people with a positive expected value.

When I say “stay alive”, I mean “preserve your ability to keep playing the entrepreneurship game tomorrow”.

Enough with the metaphors, though – what I mean in practice, is “never bet everything”. Never make decisions that can wipe you out of the game, because if that happens, you cannot continue to play. 

For some people, this may mean “never bet the company”, because if your company goes bust, so does your immediate platform for making bets and playing the game of entrepreneurship. This is also the most practical way to interpret what staying alive means. As an entrepreneur myself, this is how I personally think when making decisions in our company on a day to day basis.

However, it is not quite accurate, because truly infinite entrepreneurs are not only case agnostic, but also company agnostic. If, for example, my colleagues and I decide to go all in and “bet the company” on a decision which turns into a sour outcome and Braver goes under, I as an infinite entrepreneur will soon enough find a new idea, try again, rebuild, so long as my entrepreneurial drive is intact.

Therefore, the correct rule of thumb may not be “never bet the company”, but “never bet your own entrepreneurial drive” – never burn out so you lose the spark that keeps you coming back to the game over and over again.

This leads us to the final point of this post, which is the inherently positive expected value of “making bets” in entrepreneurship. Let us compare a gambler’s betting prospects to an entrepreneur’s to illustrate this. 

Casinos vs Startups: Where to Bet Your Time and Money

Contrary to popular belief, casinos do not want you to lose all your money to them, at least not on your first visit. If you enter the Bellagio and immediately get hit with a massive, my-wife-will-kill-me-type loss, you’ll probably leave with your tail between your legs and promise yourself to never ever come back. If you instead enter the casino, win a little, lose a bit more, but continuously feel like you have a good time, you may come back again and again and keep making bets.

Since the house always wins in the long run, the most profitable strategy for the casino is to get people to come back over and over again, bet moderately on every visit, and let the visitors bleed out slowly, metaphorically speaking. Unless you are exceptionally talented at various betting games, it is a losing strategy to keep making bets in the casino, because the expected value over a long period of time is negative. 

Entrepreneurship on the other hand, works in exactly the opposite way. If you believe in your own ability to create and capture value, and in your own capacity to get better at value creation over time, then continuously making bets in entrepreneurship has a positive (and ever increasing) expected value. If you make those bets on ideas, products or services that can scale, this is even more true. As they say in venture capital (and in NFTs… 👀), you only need to be right once – one big hit can cover all your previous losses and make you rich to boot.

Invite Serendipity to Strike

The underlying belief behind “stay alive, and keep making bets” is that good things happen to people who put themselves out there, who pursue meaningful and valuable opportunities despite the inherent risk of failure in any and all new pursuits.

Such “good things” may not happen immediately, but with continued, strategically sound and ethically right efforts over time, I am fundamentally optimistic about good things ultimately happening. In short, I believe serendipity will show up one day if you just keep on inviting it in. 

This belief colours how I navigate my own life. It is a surprisingly useful aid in everyday decision making, both in my personal life and at work.

I want to keep my health intact, not only for the sake of having good health in and of itself, but because being healthy allows me to do things I find meaningful and to live a fulfilling life. In other words, I play the infinite game of health so I get to keep playing it for as long as possible. 

Similarly, we want to keep our current company alive, but not for the sake of its existence in and of itself – we want it alive so we can use it as a platform for experimentation and for the pursuit of interesting opportunities that can have a positive impact on the world and on ourselves. In other words, we are playing the infinite game of entrepreneurship. I can strongly recommend you to try the same if you’re entrepreneurially inclined.

Have a great week,


Also published on Medium.