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Your AI Caddie for the U.S. Open

By David OralevichJune 12, 2026
Your AI Caddie for the U.S. Open

The U.S. Open tees off at Oakmont this Friday. Sixty-some of the best golfers on the planet, competing on one of the hardest courses in the world. Every shot matters. Every read matters. Every decision under pressure gets remembered.

And not one of them will walk that course alone.

A caddie isn't a bag carrier. That's the part most people get wrong. The caddie is the one who's walked the course at dawn, charted every pin position, tracked the wind shifts, and catalogued exactly which club performed in which conditions during the practice rounds. By the time the golfer steps up to a critical shot, the caddie has already synthesized everything worth knowing. They lean in and say: 180 yards, headwind, take one more club. And then they step back. The golfer swings.

That's the whole job. Not to perform for the golfer. To make sure the golfer performs.

Most business owners are trying to win a major without one.

They're carrying their own bag, reading their own greens, checking yardages between shots, and still expected to hit the ball. Emails pile up during a client meeting. A follow-up that should have gone out Tuesday is now sitting in a draft. A prospect who was hot three weeks ago has gone quiet, and nobody flagged it. The course is playing hard, and they're doing it without anyone who's walked it ahead of them.

This isn't a time management problem. It's a caddie problem.

An AI agent fills the caddie role. Not by making decisions for you. By handling everything that drains your attention before you get to the decisions that actually matter. Your inbox gets triaged before you open it. Your pipeline stays current, and anything sitting dormant for too long gets flagged. Your day starts with a brief: here's what's urgent, here's what's been prepped, here's what needs your call.

Meetings get prep work done before you walk in. Follow-ups get drafted and queued. Research gets pulled without you asking. You're not flying blind anymore. You've got someone who's already walked the course.

Marcus runs an HVAC company in central New Jersey. Twelve employees, good reputation, fifteen years in business. He wasn't struggling in the way people usually mean when they say struggling. He was booked. He was busy. He just couldn't seem to get ahead.

He was the one writing every estimate, answering every inquiry, tracking every open contract in a spreadsheet he updated when he remembered to. His pipeline wasn't being worked. It was being survived.

We set him up with an AI agent in March. By mid-May, he'd closed two commercial contracts that had been sitting cold in his pipeline for 45 days. Not because the deals changed. Because the follow-ups actually happened, with the right context, at the right time. The caddie leaned in. Marcus made the swing.

He told us: "I finally feel like I'm running the business instead of the business running me."

The players teeing off at Oakmont this week are among the most skilled athletes in the world. They've put in the work. They have the ability. And every single one of them has someone walking alongside them, carrying the weight, reading the conditions, and delivering the right information at exactly the right moment.

That's not a luxury. That's how you compete at the highest level.

If you're building something real, you shouldn't be flying blind either. My calendar is open if you want to talk about what a caddie could look like for your business.

David

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