12. I Like Weird Problems

I like weird problems.

Not necessarily big problems.

Honestly, sometimes the really good ones look almost stupid from the outside.

Why are there 400 screenshots of books in someone’s camera roll?

Why did we spend hours training somebody in a classroom only to have them forget half of it the second they started the actual job?

How the hell do you photograph 20,000 people without creating absolute chaos?

Why does a customer have to do seven things just to give you money?

Those are my kind of problems.

The messy ones.

The ones where everyone involved knows something isn't working, but nobody can quite point at the thing.

Or worse:

Everybody has gotten so used to the thing that they stopped noticing it is ridiculous.

That is usually where I come in.

The screenshots were not really the problem.

My twin sends me books.

A lot of books.

Screenshots from TikTok. Instagram. Facebook. Some random person holding a book in a Reel with three words visible on the cover.

And like every normal person, we would save them.

And then never see them again.

Hundreds of recommendations sitting in camera rolls doing absolutely nothing.

Which sounds like a very tiny problem.

Because it is.

But tiny problems are interesting when they happen over and over and over again.

The problem wasn't:

How do I organize some screenshots?

It was:

Why are we capturing information in one place when the thing we actually want to do with it happens somewhere completely different?

That question eventually became ReadDrop.

Take the screenshot.

Figure out what book is in it.

Put the actual book somewhere useful.

The interesting part to me isn't that I built an app.

It is that a stupid pile of screenshots was evidence of a broken little process.

And once I saw it, I couldn't unsee it.

I learned pretty early that training isn't the same thing as learning.

I've built training programs.

I've stood in front of people and taught them how to do the thing.

I've made the instructions.

I've explained the process.

I've watched everyone nod.

Great.

Everybody understands.

Then they go do the actual job and suddenly:

What the fuck happened?

Because there is a gigantic difference between understanding something while someone explains it to you and being able to do it Tuesday at 2:17 p.m. while a customer is staring at you, something went wrong, and you're trying to remember step six.

So eventually I stopped treating training like an event.

Teach a little.

Go do it.

Come back.

What happened?

What was confusing?

Okay, let's fix that.

Now go do it again.

Turns out people learn a hell of a lot better when the learning is attached to the actual work.

Which sounds incredibly obvious once you say it out loud.

A lot of good operations work does.

Then there was photography.

At one point I owned a photography company doing school and event photography at a fairly ridiculous scale.

Hundreds of organizations.

A giant contractor team.

Multiple photography sites running at the same time.

Thousands and thousands of kids moving through.

And here's the thing about photographing that many people:

The photography is almost not the problem.

The problem is everything around the photography.

Where does the kid stand?

Where does their stuff go?

Who's next?

Who has already been photographed?

Who is missing?

What happens when it rains?

What happens when a camera dies?

What happens when 400 people arrive differently than everyone swore they would?

You can have the best photographer on Earth standing there.

Doesn't matter.

If the system around them sucks, you're fucked.

So we got obsessed with flow.

Every unnecessary movement mattered.

Every unclear instruction mattered.

Every place someone had to stop and ask a question mattered.

At one point we got the process down to roughly 25 seconds per child.

Not because everybody suddenly became superhuman.

Because we removed the shit that was slowing them down.

That distinction matters.

A lot of businesses look at a struggling process and think:

How do I get my people to work harder?

I'm usually looking at it thinking:

Why the hell does the process require them to work this hard in the first place?

Sometimes you need to walk in through the front door.

One of my favorite things is looking at a business like I don't know anything about it.

Not the owner view.

Not the employee view.

The customer view.

Because businesses get used to themselves.

They know where the button is.

They know what that weird sentence means.

They know you have to call after filling out the form.

They know the price isn't actually the price because there's another thing later.

They know Susan handles that.

The customer does not know Susan.

The customer is sitting on their phone thinking:

What the fuck am I supposed to do next?

That's why I like secret-shopping businesses.

Website.

Booking.

Phone call.

Sales process.

Physical location.

Checkout.

Follow-up.

The whole damn path.

Because you can have individually reasonable decisions that add up to one absolutely bonkers customer experience.

And sometimes you don't need a giant technology project to fix it.

Sometimes you need to change three sentences.

Move a button.

Stop asking for information you don't use.

Put the sign where people are actually standing.

Let somebody pay you without making it a side quest.

Those might be my favorite fixes.

Tiny change.

Immediate relief.

The problem underneath the problem.

That's really what I'm looking for.

Someone might tell me:

“We need a new app.”

Maybe.

Or maybe you need one spreadsheet and for three people to stop keeping their own secret version of the truth.

“We need more staff.”

Maybe.

Or maybe your current staff spends 30% of the day doing completely unnecessary bullshit.

“We need more customers.”

Maybe.

Or maybe customers are trying to buy from you right now and your process keeps body-checking them on the way to checkout.

“We need better training.”

Maybe.

Or maybe the job itself is designed in a way that is almost impossible to remember.

I am not particularly attached to the impressive answer.

Actually, the more complicated the answer gets, the more suspicious I become.

I would much rather discover you need a $12 tool and a different process than spend six months building you some giant beautiful system you never needed.

So yes, I like weird problems.

The screenshots.

The 25-second photo line.

The employee who keeps making the same mistake.

The customer who disappears halfway through booking.

The clipboard that somehow became mission-critical in 2026.

The owner doing four hours of work every Sunday because nobody ever stopped to ask why.

Give me that stuff.

I don't need to walk in already knowing the answer.

Honestly, I'd be a little worried about anyone who always does.

I don't need to know the answer when I walk in.

I need to know how to find it.