The $1600 Lesson

Tough lesson today: I no longer have an iPhone.

I was at the batting cage filming my kid. Normally I set up a tripod outside the cage. Today I didn't — I set the phone down inside instead. One swing later, direct hit. Done.

My Thought Process

My first reaction: what are the chances of that? Maybe 1 in 50,000.

Wrong. After thinking it through, the real odds were closer to 1 in 900 — maybe even 1 in 300, given where I'd placed the phone.

My kid took about 300 swings that day. This wasn't bad luck. It was a near guarantee.

Why This Matters

I hear a version of this constantly in lending: “That never happens.”

But it does. We just don't measure it. What we call rare is usually one of three things: untracked, repeated, or a sign we're breaking our own process.

At scale, those aren't outliers. They're system problems.

The Lesson

If you don't measure it, you'll misjudge it. My “1 in 50K” assumption felt safe. It wasn't — it was a guaranteed loss waiting to happen.

The Challenge

Where are your iPhones in the cage? Ask yourself:

• What are you calling rare?

• What actually happens all the time?

• What needs to be measured so you can fix it?

— Jesse