Portable putts: Entrepreneur turns childhood memory into new business

Benji Cashdollar is the mastermind behind the portable Holes to Go

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Looking back at when you were a kid, what was your favorite memory? For many who grew up in Florida, it may have been going to Disney. Or perhaps it was watching the game with your grandpa or playing catch with your dad.

For recent Winter Garden transplant Benji Cashdollar, the memory that sticks out is playing miniature golf whenever he visited his grandparents in Florida.

“I love mini golf; as a kid, it’s something that we would do all the time when we went on vacation,” he said. “My grandparents had a place down here, and so I had been to Florida many times during winter break from school. Being from the Midwest … where it’s really cold … and (when) we got a break down here with 70- or 80-degree weather … we’d just always go mini golfing. It was weird, because we’d never go back home for whatever reason, and so it just became a wonderful childhood memory and something that stuck with me. I’ve always just had a passion for mini-golf.”

Unlike most of us, though, Cashdollar has been able to take this childhood memory and use it to build a business that provides a unique service to his community, with the side benefit of bringing plenty of smiles to kids just like Cashdollar had all those years ago. 

“As I got older and I found this unique opportunity, I think that kid came out of me again and got excited about it,” Cashdollar said. “But before I could get too excited, I had to put my adult hat on and think, ‘OK, can I do this?’”


He also needed to talk to his wife about the idea. 

“I was excited for him to have an opportunity to find something that he had a passion for,” Cashdollar’s wife, Carly Maddock, said. “You have the unique opportunity, when you relocate, to find a new career, to find something that excites you, something that makes you feel excited about when you wake up in the morning.”

So they opened a mini-golf course, with a twist. 

“When we first moved down here, I was always interested in mini golf and was looking into purchasing a permanent course,” Cashdollar said. “That ended up being something that did not work out, but the mini-golf idea had always been in the back of my mind. Then one day, I came across this idea of a portable mini golf course, and I was very intrigued.”

And the market research? That was completed through the couple’s 9-year-old daughter, Madison. 

“Having a 9-year-old in the house, we’ve been to plenty of birthday parties in this community, and every year, people are always looking for something different,” Maddock said. “What can they do that’s new and can keep kids entertained?”


Holes to Go is pretty simple. You call Holes to Go up and say something along the lines of: “Yo Benji, hook me up nine holes for my kid’s bar mitzvah on the 15th from noon to 3 p.m.”

And well, according to Cashdollar, that’s about it — with the caveat of some paperwork.

“We try to make it as smooth and hassle-free as possible. … We’ve got all the putters, scorecards and pencils — if you want to keep score and be competitive. We have nine holes with multiple obstacles, including a couple of fun ones that make it a little more Florida, like a shark and an alligator,” Cashdollar said. “We drop it all off, set it up, let them go. And then we’ll come back at the end, and we will pack it all back up and head out, so our customers don’t have to lift a finger.”

For Cashdollar, nothing beats seeing people of all ages enjoying the course and making memories.

“I love being at events, seeing people get super excited when they make a hole-in-one, having fun with their friends, their families,” Cashdollar said. “To see that type of joy is really cool. It’s exciting. It’s why we’re doing this. We just love to see it.”

To learn more about Holes to Go, check out their website: HolestoGoOrlando.com



Sam Albuquerque

A native of João Pessoa, Brazil, Sam Albuquerque moved in 1997 to Central Florida as a kid. After earning a communications degree in 2016 from the University of Central Florida, he started his career covering sports as a producer for a local radio station, ESPN 580 Orlando. He went on to earn a master’s degree in editorial journalism from Northwestern University, before moving to South Carolina to cover local sports for the USA Today Network’s Spartanburg Herald-Journal. When he’s not working, you can find him spending time with his lovely wife, Sarah, newborn son, Noah, and dog named Skulí.

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