🏟 the price of the arena

The most apt metaphor for entrepreneurship that I’ve ever come across has been Theodore Roosevelt’s The Man in the Arena.

Overlooking the convenient sexism in the title and the historical implication that striving is the ordained domain of men, it’s a beautiful passage that speaks to the truest experience of being a founder, a creator, a builder. Because really, when it comes down to it, there are only two seats in the house. That of spectator and that of gladiator.

There’s nothing in the middle.

I have incredible respect for the ecosystem of players that make start-ups into something more - the VCs, the angels, the mentors, the lawyers. But none of those roles put everything at stake for a higher purpose like the people who choose to be the first ten in a start-up … more dream that reality, more grit than gratitude, more pain than profit.

The arena is where there is no bullshit. There is only the founders that are toiling away, doing the work (this doesn’t, btw, include the “founders” that play at the title, doing press conferences in the tunnels or sitting in the box with their investors watching the team toil away down below).

The arena is where we founders look each other in the eye for the microseconds we look up to honour the other’s mission and dedication and then we get back to the work of fighting our own fights, building our own futures. I will always have the backs of my fellow founders as they have always had mine. There is a sisterhood and a brotherhood that is unknowable from the outside.

So, then, what is the price of the arena? Of the privilege to spend our days fighting for something more? Is it our financial security? Our mental health? Our personal relationships? Our physical health?

It is often these. But these I can contend with. These are the choices we each make as we step foot into the arena and that we need to manage as well as we manage our P&Ls, our teams, our culture.

What then of the spectators? What price should they be able to inflict for the purpose of sport?

Because let’s be clear: over the past couple years it’s started to feel like this is all one big sport where casual bystanders seemingly feeling left out and left behind feel the only way to stay in touch and involved is to start tearing it down. To relish in the downfalls. To find glee in the gritty mess of it all. (To be fair, there are imposter founders who make a mockery of the work and I’d call the demise of their “companies”, karma - though nothing to be remarked on or lauded either way).

Founders are fallible. We are human. Most of us have big hearts and big dreams and big egos and alot of pride. But we don’t ask for glory - we seek our users’ favour. We toil in service for those magic moments when we make something people want and need.

And we’ll get things wrong. We’ll get so much of it wrong. Hopefully they’re small things and we have the support and space to learn and do better. Sometimes they’re big things.

The ultimate irony? If you’re not making mistakes, you’re not moving fast enough. Trying bigger and bolder things. You’re quite literally not doing your job unless you’re pushing the lines of what is possible.

But to do that it needs to be okay to make mistakes. To fail. To try and try again.

To be supported in the trying, not just in the succeeding.

But today? The price the spectators ask of the founders in the arena seems to be suggest a different calculus. One intent on a pound of flesh for every misstep, every shortcoming.

Though sadly, but perhaps not surprisingly, only for some of us.

The spectators seem thirsty only for the blood of those that have already fought endless battles just to get to the arena - women, under-funded and under-represented founders. Those already making do with less.

A friend moving fast and going through so much, made a mistake. One that she acknowledged and owned.

A fellow founder made the incredibly hard but responsible decision for her company to hand the reins over for someone better suited for the next phase of the company.

I could keep rattling them off but that keeps giving oxygen to what is already too rampant.

Why the glee? The mean barbs aimed to hurt not lift up in incredible hard moments?

This is not okay.

The final privilege is the luxury of fucking up with impunity. To have endless safety net to be able to fail upwards.

Take down irresponsible behaviour. Reckless behaviour. Frankly, the behaviour that we all allow to continue unchecked by rich, white men with ample safety nets who get to control narratives even in the reckless carnage of their own making. Hold them accountable.

But stop killing the trying. For putting a unpayable price on the trying. On the very responsible and very necessity process of fucking up, owning up to it, learning from it, and trying again.

This is what trying looks like.

It takes incredible courage to step into that arena, sans armour, sans protectors. It takes even more to be knocked down and to stand back up. And it takes everything to go back into it. To remain one “whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming.”

If we as a society want to benefit from the gains of this striving, this sacrifice, then we have to stop this ridiculous spectacle of tittering at every setback. Of treating these lives’ work like reality TV - for your viewing and mocking pleasure. Especially for those that already have been over-scrutinized to get so little.

If you think you can do it better, suit up and step in.

Otherwise, find your way to celebrate the trying. To cheer the wins and rally the losses.

And if you can’t do any of that, stay away from the arena altogether. There is real work to be done and it’s hard enough.

If we are going to endure and thrive in these incredibly challenging times then let us not be a country of “sneering cynics”.

"Let the man of learning, the man of lettered leisure, beware of that queer and cheap temptation to pose to himself and to others as a cynic, as the man who has outgrown emotions and beliefs, the man to whom good and evil are as one. The poorest way to face life is to face it with a sneer. There are many men who feel a kind of twisted pride in cynicism; there are many who confine themselves to criticism of the way others do what they themselves dare not even attempt.”

Let there be a price for doing hard things. There must always be one, and it is paid willingly, gladly, by those of us who choose to spend their one “wild and precious life” in service and in building.

But let’s not fool ourselves into thinking that because we bought a ticket to spectate that we have the right to add to that price.

Suit up. Step in. Or step aside.