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Rob O’Loughlin with some examples of Ad Flag.

MADISON – Rob O’Loughlin is pitching his latest and greatest new idea, Ad Flag, but one story reminds him of another, which reminds him of another. Out they come, rapid fire, occasionally in completed thoughts and sentences, other times morphing into something totally unrelated.

In roughly the time it takes Bryson DeChambeau to line up an 8-foot putt, O’Loughlin talks about once playing golf with Billy Casper, how advertising has changed in the digital age, declining TV ratings on the PGA Tour, befriending billionaire Scott McNealy, slow play and CBD.

Energetic, animated and eminently likeable, O’Loughlin is the best interview this side of Muhammad Ali. A natural-born salesman, he could sell hip waders in the Sahara and parkas in the Amazon.

Beneath the patter, though, is a serious inventor-entrepreneur. O’Loughlin fundamentally changed the game of golf in the mid-1990s with Softspikes before launching Laser Link Golf, a company at the forefront of the distance-measuring device boom and still his primary business.

Both were smashing successes, but he’s also an unreformed risk-taker who has championed ideas and products that never, or barely ever, saw the light of day.

“I’ve had a lot of projects that didn’t make it,” O’Loughlin says with a self-deprecating laugh. “I’ve got four or five I can show you. They’re some real dogs.”

His latest project is Ad Flag, which seems destined to be one of the success stories, though one never can tell. You are reminded that O’Loughlin’s Big Cup should have made it big – pardon the pun – too.

What is Ad Flag?

It’s a simple but ingenious way for businesses to advertise on hole flags and for golf courses to profit from it. The ads are displayed on triangular or rectangular pieces of plastic that are sewn onto hole flags, on the side closest to the flagstick. Because the plastic is rigid, the flags don’t droop, even on windless days.

“What you’ve got here is 100 square inches of advertising space,” O’Loughlin said. “It’s the equivalent of the front page of Golf Digest. Now, if you’re The Oaks (an 18-hole public course in Cottage Grove), you’ve got 24,000 guys who go to the first hole (annually).

“If I said to Callaway or to Culver’s or to Coors, ‘Would you pay me $300 for the year, to be out there on a flag?’ Well, that’s a penny a player.”

Here’s how it would work: O’Loughlin would pay for a course’s flags, which are made by Madison-based National Golf Graphics, whose director, Peter Meyer, is O’Loughlin’s business partner. A course typically replaces its flags annually at a cost of about $700.

“I build the flags and I give them to the course for free,” O’Loughlin said. “And on top of that I give the course $1,000 in ad revenue-sharing. So, I save the superintendent $700, I give them $1,000 cash and I give them a new set on May 1 every year for three years.”

O’Loughlin then sells the advertising for the flags. At $300 per flag, that would potentially be $5,400 per course. He’ll depend on the courses to recommend members who might want to advertise – realtors, insurance salesmen, auto dealers and the like.

“Geico. Starbucks. Who wouldn’t do it? It’s a penny (per impression),” O’Loughlin said. “What’s the No. 1 delivery at daily fee golf courses? The beer truck. We can get that guy, right?”

He’s been around long enough to know he’s not going to get private courses to buy in. Ad Flag is a non-starter at, say, Milwaukee Country Club, where the members would revolt if they saw a Miller Lite ad on their flags. But privately-owned public facilities and municipal courses are another story. Which muni wouldn’t want to save a couple thousand bucks for basically doing nothing?

There already are advertisements on hole signs and benches on many public courses. GPS units on golf carts display ads. Why not flags? What if Titleist or Coca-Cola bought the 18th hole flag on every public course in Wisconsin? The possibilities are endless.

O’Loughlin has approached some of the major golf equipment manufacturers and has gotten nowhere. He pitched the idea to Culver’s co-founder Craig Culver, who “didn’t get it – and he’s a golfer.”

Golf, O’Loughlin knows from experience, is slow to embrace change.

“They say, ‘That’s not the kind of advertising we do,’” he said. “I’ve already been told no by Titleist and Callaway, but they haven’t got their head around it yet. I think they’ll come around. I think I can crash through the objection of, ‘We haven’t done that in the past.’

“Titleist, Callaway, TaylorMade – they will come to understand the value when the other guys do. When Wally Uihlein reaches out and grabs a Callaway flag, he’ll say, ‘Now I get it.’ ”

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