There Has to Be an Easier Way to Get Four People on a Pickleball Court

I play a lot of pickleball.

And one of the hardest parts has nothing to do with pickleball.

It’s getting four people on the same court at the same time.

A typical game starts with a text:

Anyone want to play tomorrow at 10?

Then the replies start.

“I can do 9.”

“Can’t tomorrow. Thursday?”

“I’m in.”

“Who else is playing?”

Before long, you’ve sent ten texts to organize a 90-minute game.

It got me thinking: why am I doing this?

This seems like exactly the kind of small, annoying job AI should handle.

Imagine texting a number:

Find me three players tomorrow around 10.

It knows your regular group. It sends the invitations. The first three who say yes are in.

Someone cancels? It finds a replacement.

Then everyone gets a confirmation and reminder.

No app to download. No new platform to learn. Just a text message.

The Bigger Opportunity

I’m not sure I’ll ever build this.

But I find myself increasingly interested in businesses like it.

AI gets most of the attention for the big things it might change—jobs, industries, medicine, education.

I wonder if some of the more interesting opportunities are much smaller.

Look for something people do over and over again that is mildly frustrating, inefficient or unnecessarily complicated.

Then remove the friction.

Scheduling a pickleball game isn't a billion-dollar problem.

But there are millions of little problems just like it.

And those may be some of the best places to start looking for what AI can actually do for us.

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I help entrepreneurial people think through what’s next in their work, business or ideas. If something here sparks an idea or conversation, I’d love to hear from you.