Why I'm Writing Again

I’ve been in enterprise software sales for almost ten years. That means I’ve spent most of my adult life in rooms where the whole job is forming a fast, defensible opinion about a company you met forty minutes ago.

You get good at it. You also get lazy about it, because nobody writes any of it down. The take dies in the room.

So this is the correction. Same opinions, permanent record, and now I can be wrong where people can see it.

What I actually do all day

I’m an Account Executive at Cloudflare. On paper that means I sell infrastructure. In practice it means I sit across from a few hundred businesses a year — retailers, banks, health systems, gaming companies, a surprising number of car dealership groups — and try to figure out what’s actually going on inside them.

Not what the press release says. What’s going on.

Who has budget and who’s pretending. Which “digital transformation” is a real re-platforming and which is a rebranded cost cut. Which CIO has political capital and which one is getting managed out in eighteen months. You learn to read a company the way a scout reads a roster: not by the record, but by who’s actually producing when the game is close.

That’s a genuinely great seat. And the thing I keep noticing from it is how much public commentary about business is written by people who have never had to get a purchase order signed.

The thesis, such as it is

Most takes are downstream of incentives.

That’s the whole framework. When a company does something that looks stupid, it’s usually not stupid — it’s rational for the person who decided it, given what they’re measured on. When an economist and a small business owner disagree about inflation, they’re often both right and describing different things. When a coach punts on fourth-and-two, the math says go for it and the incentives say don’t get fired.

Figure out who’s getting paid for what and most confusing behavior resolves itself.

I’m not going to be right about all of this. But I’d rather commit to a position and revise it in public than hedge everything into the kind of prose where nobody can tell what you actually believe.

What you’ll get here

Five things, roughly:

• Business — go-to-market, sales, how companies actually buy things, why most enterprise software is sold and not bought
• Economy — markets, rates, Florida real estate, and the widening gap between the data and the vibes
• Politics — mostly the incentive structures, less the team sport
• Sports — Dolphins suffering, college realignment, and the increasingly obvious fact that every league is a media company now
• Tech — what’s real, what’s a demo, and what’s a slide in a board deck

No newsletter cadence I’m going to promise and then miss. I’ll write when I have something worth the time it takes you to read it.

One rule

If I make a claim, I’ll try to tell you what would change my mind about it.

That’s the part missing from most writing on the internet. Everyone’s certain, nobody’s falsifiable. I’ve been in enough deals that went sideways to know how expensive that particular habit is.

Fair warning though: I’m from South Florida, I follow the Dolphins, and I’ve been long a few things I probably shouldn’t have been. Calibration is a work in progress.

Let’s go.