title: "Don't skip the founder profile" date: "2026-06-21" excerpt: "A jack of all trades, a Head of Retention interview, and a 1am SQL session the night before... why the resume that looks 'all over the place' is often the most interesting one in the stack."

Don't skip the founder profile

A friend of mine recently posted an email he'd sent to a founder. It was about how the founder's resume and abilities were spread all over the place... too many things, too many directions, hard to pin down.

I read it and felt it in my chest. Because that used to be me. Honestly, it still is.

I'm a jack of all trades. Well-rounded, generalist, T shaped, whatever word you want to use. I can do a lot of things, and I can do most of them well. And here's the trap nobody warns you about: when you can do many things well, you forget that most people can't. So you show up assuming everyone is operating the same way you are... and you read the room wrong.

The retention interview

I was once offered a Head of Retention role. During the process they asked a very reasonable question: how would you fight churn for this specific kind of user?

So I did what felt obvious to me. I queried their actual database. I pulled the real top reasons people were leaving. And then... I gently took apart a few of the reasons they'd assumed were valid, because the data didn't agree. They were looking in some of the wrong places.

What I did not bring was a tidy strategy narrative. Or beautiful slides. I hate making slides... blame that on a tour of duty in consulting and every VC who has ever asked me for a deck.

Here's what I understand now. For that role, I should have played it differently. I should have walked in as if I didn't know how to write a single line of SQL... and instead shown how I'd build the frameworks and the questions that get other people to bring me the data. That is the job at that altitude. Lead the thinking, not the query.

But that is exactly the founder problem

The irony? The night before that interview, I was a founder wearing every hat in the building, firefighting a real churn case at midnight... in SQL.

That's the whole tension of the founder profile. One night you're in the database at 1am because the company needs you there. The next morning you're supposed to abstract all of that away and just "be strategic." Both are true. Both are me.

I won't call myself a box of chocolates... but you genuinely don't always know which version you're going to get, and that is the point.

Why you shouldn't skip the founder

When you see a founder profile that looks "all over the place," read it again.

That person has stress-tested every function in a company with their own hands. They've lived the messy version of product, of go-to-market, of data, of support, of the 1am incident. They know what good looks like across the board because they were personally bad at all of it first, then got good.

The breadth isn't noise. It's range. The only real work is helping that person turn range into a story a hiring manager can hold in one hand.

So no... don't skip the founder profile. It's often the most interesting one in the stack.