Optimistic AF
My knee jerk reaction to the essay heard around the entrepreneurial world, "Founder Mode" by Paul Graham of Y Combinator renown, was that a lot of founders likely aren't good with people and have trust issues. I've known a lot of founders who match this description, and I was doing a bit of instant pattern matching.
I've sat on this for a while now, ruminatin' a bit, especially now that I'm a founder of sorts.
And what I'm going to talk about instead is optimism.
Every founder I've worked with has been fundamentally an optimist, including myself.
You can't do this - create a new thing from scratch - without believing in your bones that things will work out.
No matter how low the bank accounts get, how dry the pipeline is, how many "no"s you accumulate, how many times a customer sends an email on renewal day wanting to chat, things will still work out.
So, you can look at an upcoming bill and think "I'll get that paid."
You can hire a VP and believe they'll work out.
You can see the upside in situations and people and outcomes ... every cloud has a silver lining that shines through.
That optimism can be paired with criticality, even anger, dashes of asshole, what have you in some cases, but at the core of every founder is a nougaty bit of raw insane optimism.
But a lot of seasoned operators - the folks they hire for the roles Graham talks about - have likely seen some shit. They've seen that optimism fail, likely spectacularly. And they're not as bought in as the founder.
So, they will fight - optimism vs learned cynicism and an earned bit of defeatism and caution.
For an inexperienced founder, that's going to be difficult to mesh and manage ... especially if you also fit the archetype I mentioned at the top.
Finally, the essay itself comes from a self-serving point of view. If you're Graham, you want potential founders attracted by that vision - of the iconoclast founder damning the torpedos and doing things their own way. He's cherry-picked some survivors who match his own vision of a successful, VC-funded founder because he's a VC looking for just those people.
It's not the only way that works. Like most software, it's a miracle that anything ever works, and every situation is bespoke.
I suspect there's no pattern here at all ... just people making stuff up as they go along.
Just like the rest of us.
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Speaking of optimism ...
Twice last week somebody out of the blue called me - or something I said - "inspiring" ... which feels super weird and makes me weirdly emotional.
In both cases, I was admitting that I've accepted that I'm an optimist in my ripe old age - an age where you'd think I'd know better.
When I was younger, I thought of myself as misanthropic, cynical, and learned. I was kind of surly sometimes, and had a practiced disdain of most things.
Looking back now more than halfway through my 40s, I recognize that I was projecting myself from my optimism.
Because being optimistic is vulnerable. You end up putting your hope flapping in the wind, waiting for folks to trample it, or spit at it or rip it from your hands.
If you hold it close to yourself and bury it beneath sarcasm and cynicism and doubt, you can protect yourself from the hope.
After all, it's the hope that kills you, they say.
Fuck that.
It's the hope that sustains you. It's the hope that feeds you. It's the hope and optimism that drives you and builds you.
So, fuck it. I'm going to be optimistic as hell. Will everything work out? No, but I'll figure it out and deal with it and hope anew.
One of the "inspirational" bits I shared was that this very moment - right now as you're reading this - is the culmination of all the moments that came before. All the things you've done, all the lessons you've learned, all the mistakes, all the heartbreak, all the growth, all the loss, all the wins ... all of it, everything.
All of it built to this exact moment. Maybe it's where you always wanted to be, maybe it isn't, but this moment is the reality of where you are.
And where do you want to go from here?
How do you build from here - an inch, a centimeter, a foot, a mile - anything at all.
What do you want to do with this moment - this greatest moment of your life so far?
Be optimistic. Go fucking get it.
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One final note. I shared the above thought once and got a "That seems depressing" ... because while I view each preceding moment as a building, a climbing, a growing, the listener viewed each moment as an erosion of sorts, a weathering, a weakening.
That might have been the moment it truly locked into my brain that I'm an optimist - likely an irredeemable one (but I have hope!).
I saved it by ending with this:
Tomorrow will be an amazing day, no matter how shitty today might be.
And that is true every day of your life.
"Go be awesome because you are, in fact, awesome" is something I say to my son every day before he gets out of the car at school drop off - and I'm saying that to you today, too.
Here's to an amazing tomorrow!