About

Hi, I'm Brian

I'm 55. I've spent most of my career in sales and management. I am not a tech person, and that turns out to be the entire point.

The short version

About a year ago I decided to actually figure out what AI does, instead of nodding at every post that mentioned it.

This newsletter is me reporting back, once a week, on what I've tried, what worked, and what I broke. It's for people like me — mid-career, smart, curious, and quietly worried that everyone else is somehow ahead.

You're not behind. The people writing the loudest posts about AI are mostly bluffing too. I just decided to bluff in public.

Brian Cleveland

Why I'm doing this

Two reasons.

One: I learn faster when I have to write it down for someone else. Writing this forces me to actually use the tools instead of just reading about them.

Two: There's a giant audience of mid-career professionals being talked past by the AI conversation. The 25-year-old AI influencers are great at what they do, but they're not speaking my language, and they're definitely not speaking yours. Someone our age should take a swing at it.

A little more about me

I'm a Key Account Manager in the payments technology sector — which sounds like the kind of job where I should already know what AI does. I do not. That's most of why this exists.

I have an iPhone, I get confused by my smart TV, and the closest I've come to writing code was COBOL I and II in college, where I typed thousands of lines copied straight from the textbook and never — not once — got a single program to run. I somehow passed both classes. To this day I assume the professor took pity.

That's the whole point. If AI only works for engineers, it's a very expensive party trick. I think it works for people like us too, once you find the right way in. I'm trying to find that way in, in public, so you can follow along.

The teaching part

Thirty years of my career has involved training and teaching people something they didn't think they could do. That's the part of this I'm actually qualified for. The AI part I'm learning right alongside you — but standing in front of a room and making a hard thing feel doable, I know how to do that. It's why the live class exists.

The other thing I built

Somewhere in the middle of all this I got so annoyed by my own family calendar that I built a product to fix it. It's called FamilyPilot, it's live in all fifty states, and real families pay for it. I still can't write a line of code. Issue #9 is the story of how that happened.

The “Brian Tries” thing

A friend asked why I didn't call it something more obviously useful, like “AI for Sales Professionals.” Two reasons. One: it would be boring. Two: if AI gets boring in three years, I'll try something else. Brian Tries Retirement. Brian Tries Pickleball. The format is the franchise. The topic is just whatever's making me feel old this decade.

Say hello

I read every reply. Email me at hello@briantriesai.com, or just hit reply on any issue — it comes straight to me.

It's free. It's weekly. It's short.

That's me. Your turn.

One issue a week, free, about 800 words. Start with the next one on Sunday.