Have Rob O’Loughlin and his family always played golf?

Still not yet.

He is still going strong. O’Loughlin is a rebel in the best sense of the word. He is an innovator in the golf business (after 20 years in the formalwear market). In short, his golf record says the following:

A second shift began with spikeless golf shoes, which were made possible by softspikes, which were non-metal spikes that changed golf and greenskeeping for good.

Laser Link Golf was one of the first companies to use lasers to measure distances, which was a cool new technology that players loved but the sport’s old, stuffy governing bodies didn’t.

Big Cup, a big idea to make golf more fun for most people by making the hole 6 inches across instead of 4.25 inches across. O’Loughlin, who has lived in Madison for a long time, is trying this idea again.

AdFlag is a way for golf clubs to make more money by putting ads on the flagstick flags. More money is good for everyone.

There are many more, but for now let’s just say that O’Loughlin has always worked to improve golf for players. Sports Illustrated had questions, and O’Loughlin, who is in his late 60s now, had a lot to say…

The Sports Illustrated: Softspikes, which changed from metal spikes to plastic ones, were a big change in our lives. You were there when the tide turned. How did it go?

It’s Rob O’Loughlin: You won’t believe it’s been 30 years. When we first showed the product at the PGA Merchandise Show, everyone told us we had no chance. About 6 feet long, this is the card table we set up. My business partner stood there with these plastic spikes in his hand. After every club pro, someone said, “You’re kidding!” You know, “You’re not serious!” We said, “Yes, we are.” We believed we were on our way.

SI: None of us golfers liked putting over the metal spikes’ raised root marks on the green. Soft spikes were a huge step forward, especially for golf superintendents.

RO: We’re not upset about it, but no one will ever fully credit us. When the metal spikes were taken out, a lot of things changed. Things like bar chairs, marble floors, and carpet in the clubhouse. Golfers saved a lot of money by using soft spikes. At PGA West, you had to go down some concrete stairs from the hotel to get to the golf course. Everyone took a step in the same place. Every year, the metal spikes wore down a whole set of concrete stairs. Thank you for the great deal. It made me think of other golf-related things that would be useful. Some of them haven’t done as well as Softspikes.

SI: Golfers now use rangefinders and GPS devices all the time, but that wasn’t the case at the beginning of this century. Why do you think the people who made the rules were so opposed?

RO: I told my LaserLink business partner that I thought the rule about electronic measuring tools could be changed in a year or two. It took ten years.

SI: It looked so clear, though. Now, rangefinders can be used in the PGA Championship.

RO: Some things in golf are against what the powerful people in golf want. They really don’t know why; they’re just that way. There was never a doubt in the minds of Peter Dawson, David Rickman, or any of the USGA guys that rangefinders were wrong. They would always say, “Oh no, we can’t do that!” “We’ve never done that before!” Rangefinders were the same as spray heads that used yardages, but they worked faster. It’s clear that those guys didn’t think about it. They couldn’t give a good reason why measure tools were helpful. But they kept us away for ten years.

SI: Didn’t it happen at the same time when they stopped anchored putting?

RO: It happened when golf was in bad shape, maybe even going out of style, and that rule may have turned some amateur players away from the game.

I met Peter and David in 2006 in Scotland. They were very close to changing the rule so that measure tools could not be used in competition. I feel like a fish out of water as I sit with them in the R&A lounge. We are just talking. I told you it wasn’t a big deal, and people like it, just like they like scramble contests. He then asked Dawson, “Have you ever played in a scramble?” He asked, “No, have you?” The actor replied, “No, I haven’t. But my daughter is a pretty good player, and she just played in one and said it was a lot of fun.” Two of the most powerful golfers in the world have never played in a scramble.

SI: From what I remember, there wasn’t a big push to ban fixed putters. Then, someone from the USGA told me that the R&A was mostly behind the push. Later, a long-time PGA Tour rules official told me about the time he played golf at a famous British course and was putting his bag into his trunk while a long putter stuck out. “Does every bad idea come from America?” Peter Dawson asked him with pride when he saw him.

RO: I wish they would look at the ban on long putter anchoring again and let some old guys back into the game.

SI: The push for a ban didn’t begin until soon after Ernie Els beat Adam Scott with a belly putter to win the British Open in Dawson’s garden. It was clear that Dawson was upset.

RO: My wife laughed when she read a quote about me in a golf magazine while we were setting up the measuring tools. People asked Peter Dawson if he knew who Rob O’Loughlin was. Peter replied, “Oh, yes, I have a hard time avoiding him.”

SI: What is the latest on your long-running Big Cup idea?

RO: This is where I want to die. This is what I call Mission Impossible. There is a lot of proof. A normal golf hole has a playing area of about 8 million square inches. That’s about 144 million square inches of game area when you multiply it by 18 holes. There are 255 square inches of cups in 18 four-and-a-quarter-inch cups. That’s totally crazy. It doesn’t make sense; that’s just how golf has always been done.

SI: How big do you think your Big Cup should be?

RO: 6 inches. It didn’t work out when I tried to sell above-ground plastic Big Cup pieces. I’m now using in-ground metal cups again. The hole starts to fall apart if you make it bigger than 6 inches. Remember when Mark King from TaylorMade did a deal where they tried out a 15-inch hole? That was crazy. That didn’t work out. I believe he played it too safe. It’s not a big deal to move it from 4 inches to 6 inches.

SI: How hard is it to get people to agree with this change?

RO: You as a good player might not want to play in the Big Cup. Everyone plays a little faster, though, if every four-footer was like a two-footer. Tee It Forward is the best way to compare it to the Big Cup. I think it’s one of the best things to happen in golf in the last 30 years. I’m a single-digit player who is clinging on like crazy to stay at a 9 or 10 handicap. We played on the blue tees for 30 years. We all switched to shorter t-shirts now and won’t go back. It’s not a par-4 if you can’t hit it with two woods.

SI: I’ve seen how ego and skill can get in the way of golf. A lot of 15-handicappers won’t play from the tips, where they don’t have a chance. They still do it, though. How do I get up this hill?

RO: Once golfers move, I don’t think they’ll go back to the 4-inch cup. You’ll play faster, get better points, and have more fun. If you had the Big Cup, you would never need to move the flag. It doesn’t matter that the ball bounces off the flagstick that has a six-inch hole in it.

SI: How mad are you that you still miss an 8-foot putt to the Big Cup? That must be even worse.

RO: Bad putters will still be bad, and good putters will still be good. The three-putt will no longer be possible, which is one of golf’s worst mistakes. You have 9 feet to make a birdie, but you miss that when you hit it past 4 feet. That is the worst thing that can happen in golf. There had to be long putters and belly putters because our greens move so quickly. In 30 years, even at country clubs, they went from an average of 7 on a Stimpmeter to 12 or 13. That is a huge change. No matter how good you are, no one likes a three-and-a-half-foot steep putt on a wet green.

SI: Someone chose that the hole should be four-and-a-quarter inches in the first place.

RO: It’s not a love story, but when people first cut holes in the ground in Scotland, they used a plumber’s drain pipe. It was four and a half inches wide. In the late 1890s, they did use a 6-inch cup for eight or ten years, which is interesting. Gene Sarazen, also known as “The Squire,” pushed for that bigger hole later. Ben Hogan was the same way. He wasn’t good at putting and always thought it was an unfair part of the game.

SI: The Big Cup should be fun for most golfers. You might want to make National Big Cup Day a holiday and get the word out about it.

RO: They’re already going on a rogue streak on thousands of Big Cup days at different venues. If I broke the rules in another job, it didn’t bother me. The hole size is the only golf number that hasn’t changed over the years. Now, guys drive it at least 50 yards farther. The green speeds are a lot faster. Is a club sandwich still 95¢ like it was when you first joined the club? No. One important thing has not changed at all.

SI: What will it take to make the Big Cup a big deal?

RO: If you’re a golf club, just say, “This is how we do things here.” If it works for the course down the street, other courses will always do the same thing. Some courses will cut a green into two holes so that you can play to the one you want. For fun games, if some courses went to the Big Cup, they’d all go there in a New York minute.

SI: Have you ever heard a player say, “I didn’t like that course,” after a round? “I played too quickly and shot too low”?

RO: Yes, it has never happened. Without a doubt, play is faster. Plus it’s more fun. Everyone wants to make more putts.

SI: Almost everyone, Rob. Peter Dawson is likely to call you soon.