You probably shouldn’t work for me

You’re a person. And I’m going to do my damn best to treat you with agape. But that doesn’t mean we should work together.

Here’s a cheat sheet if you’re considering working with me.

I’m not saying any of this is right, it’s just me.

• You’re not on purpose.

  I like honesty. Commercial ventures exist to generate profit (generate ≠ maximize). Full stop. We’re not changing the world. We’re not bettering humanity. Everything else is marketing. Which is not to say we shouldn’t market that we are in it for the mission / customer / world changing / AGI / Mars / etc - but we mustn’t forget the truth…

  The caveat - working on things that could also be marketed as changing the world is probably more fun. Insurance is profitable sure, but it’s dull. We’re here to generate profit, ideally doing fun stuff. The line that can’t be crossed is doing fun stuff while breaking profit.

This is foundational for me. I fire fast for misalignment.

• You’re not into outcomes. You can’t or won’t be measured. You don’t deliver.

  I believe all people at a commercial venture can (and should) have accountability and measurable value. The measuring can be effortless. Stephen Curry type personas (making everyone else better) are measurable. The most valuable team members are the ones that deliver outcomes. Not delivering is terminable.

  I want to work with people that are right (proven with outcomes), regardless of how messy their approach, regardless of how many rules get broken being right. My least happy work moments were when policy or appearance were setting the approach.

  I default distribute resources to those that deliver, with some frugality, as abundance encourages bad decision making.

• You need a low pace. You expect lots of direction. You want premature perfection.

  Pace is a lever. It’s not magic - changing it has consequences. I like a high pace. I’m quick - I don’t need much to get to the point.

  I expect you to make progress when I’m not with you. I expect to help you make decisions, and to help unblock you. Otherwise you inherently proceed.

  In my career I’m at the beginning of things - I don’t often get to work with craftsmen or perfection. Mostly I juggle speed and good-enough.
  (I’m quite frankly conflicted on this one… I have deep respect for craftsmen. I love the romance of improving at something daily for a lifetime. I value - and personally purchase - the outputs.)

• You don’t like direct feedback.

  I’m default direct. I prefer honesty. I’m comfortable with conflict - occasionally I’ll introduce some if we’re stuck. I prefer high-trust collaboration and consensus - but it doesn’t scale. If I’m being diplomatic or gentle it’s probably because I can’t afford not to be.

• You don’t like risk. You are uncomfortable with ambiguity / uncertainty.

  Risk is a lever. It’s not magic - taking more has consequences. I’m comfortable with high risk. We might fail. Some of our bets will be wrong. Some of our bets need to be right.

  I’m a starter. I want to work on uncertain things. I tend to be early to whatever it is I’m working on. Early isn’t always profitable, but it’s absolutely uncertain. Layer on startup-isms like cash runway, GTM, etc.

  I explore and experiment constantly. I like the surface area of it. The riskiest bets I’ve felt as I’ve made them are often when I’ve explored that thing the least. I’m not saying move slower, or don’t make the big bets. But I’ll try hard to run an experiment today if I think I’m going to need to make a bet in, say, 6 months.