Inside Tailgating caught up with CupCheck CEO and retired MLB pitcher Kevin Jepsen to learn more about his new yard game, its origin, the struggles of getting the product to market and the countless memories it has created for the CupCheck family and anyone else lucky enough to play.
Watch our full interview with Jepsen in the video below and read along to learn about CupCheck and what makes it one of Inside Tailgating’s favorite games of 2021.
Video interview with former MLB player and CupCheck CEO Kevin Jepsen:
For avid tailgaters and yard game enthusiasts, the rush of a narrow victory in the race to 21 points in a cornhole match is tough to beat on a day when the sun is warm and the beer is cold. But those same players understand the games we play are about far more than wins and losses. They’re about camaraderie, friendship and creating memories to share for tailgates to come.
For Kevin Jepsen, a retired pitcher who spent a decade in the majors, that itch for competition and community is scratched by CupCheck, the game he perfected with his closest friends and teammates.
CupCheck is a beautiful blend of simplicity, portability, action and strategy. Four plastic poles hold one cup each and teams of two try to split the poles with a plastic disc or, at worst, knock a cup of its perch and onto the ground to score points. The duo not tossing the disc plays defense and tries to keeps its cups from hitting the ground.
‘It just became something we did‘
As with any product, CupCheck wasn’t always nicely packaged and branded. Jepsen was introduced to an early version of the game in 2016 on an off-day between games. He and Tampa Bay Rays teammates Matt Andriese and Curt Casali took a trip to Los Angeles beach, and his agent brought along four PVC pipes, stuck them in the sand, put cups on each pole and broke out a disc. It wasn’t exactly love at first sight.
“There was no name for it. It was just something that had been floating around,” Jepsen told Inside Tailgating. “At first we said we don’t want to play this thing. Let’s just throw the football around. But he finally talked us in to playing it and it was awesome.
“We were making up rules as we went because it wasn’t a game we’d ever played. Nobody knew what it was. It just became something we did.”
‘We should see if we can make this thing’
That next summer, Jepsen and his friends decided to take this mystery game out of the sand and on a road trip to Phoenix for a NASCAR event. After a bit of novice handyman rigging with 2x4s and cinderblocks, the next iteration of what would become CupCheck earned some serious attention at the track.
Jepsen said race fans flocked to the game in the infield and, after some initial questions, fell in love with a game that had no real name and no real rules. It was just fun.
“We knew we loved to play this thing, but it definitely catches peoples eye,” Jepsen said. “So I don’t know if it was because we were a couple days into camping out at NASCAR or what, but we got this idea of, hey, we should see if we can make this thing.”
So there it was. Less than a year after scoffing at this game on the beach, Jepsen, Andriese and Casali were suddenly professional baseball players and amateur entrepenuaers. They quickly found out the latter was just as hard the former.
Jepsen said it took years of meetings with lawyers, designers and manufactures just to get CupCheck of the ground and in to production.
“All of us involved, we’d need made anything,” Jepsen said. “We were able to just meet different people along the line from our inner circle knowing a buddy of a buddy type deal.”
Thanks to the hard work of Jepsen, his buddies and his buddies’ buddies, CupCheck launched in the spring of 2019. The CupCheck crew, which now included big-name guys like Evan Longoria and Yasiel Puig, expected orders to pour in followed closely by cash and national fanfare. But Jepsen noted: “That didn’t happen. It doesn’t work that way.”
Jepsen and the team, however, stuck with the project because slow sales wasn’t the first problem they dealt with since that day drunken weekend at Phoenix Raceway when they decided to take their little game to the masses.
“We could have pulled the plug multiple times, but we had faith in our product and knew we had something that people love to play,” Jepsen said. “That pushed us through.”
‘People just got stir crazy and needed something new’
CupCheck made its rounds at musical festivals and NASCAR races throughout 2019 with Jepsen selling the game on-site. That all stopped when COVID-19 shut down gatherings nationwide in March 2020. Drunken NASCAR fans and hyper-competitive college guys were no longer the target demo for CupCheck — bored folks looking for something to do in the backyard during lockdown were suddenly keeping CupCheck afloat.
“It’s hard to tell,” Jepsen said when asked in COVID took a toll on his young company. “I don’t know where we could have been if we could have done the summer events and tailgating. … But our game, you can play it anywhere. It has the base so you don’t need grass or sand to play it on a beach. You can play it on concrete, your back yard, the quad at your apartment.
“People just got stir crazy and needed something new and fun to go outside and do.”
Now videos of people playing CupCheck litter social media with everyone from toddlers to 60-year-old men diving to the ground to catch a cup. The best videos, as you’d guess, feature stumbling guys with a half-empty beer in one hand.
“Our game says 12-and-up in it, but you definitely have some adults playing the game. And after a few adult beverages it can get exciting,” Jepsen said while admitting to the fact his play sometimes levels up alongside his BAC. “You get a little more creative when it comes to catching that cup as the day goes on and you’ve had a few of them. And for those spectators on the sidelines, the entertainment gets a lot better and you draw more of a crowd.”
If a player wants take things up another notch, Jepsen said things get most interesting and intense when there’s a little money on the line.
Jepsen, who played for four different MLB teams and appeared in nearly 500 games, now competes with his co-founders and family members at CupCheck every chance he gets. He said he often travels with the game because its package is small enough to stuff under an airplane seat.
‘This is our own little community’
CupCheck, for Jepsen and so many others, has become more than just a pile of plastic pipes and four cups. It’s a conversation starter, a requested activity and a common thread in so many memories with friends, former teammates and close family members.
“This is our own little community,” Jepsen said. “It’s something that’s cemented in our family’s lives and the other guys, as well. It’s a talking point. When you go somewhere make sure you have CupCheck with you because you’re going to be playing it all day.”
Inside Tailgating’s Take on CupCheck
I love the story of CupCheck for so many reasons, but I’ll start by explaining why I think this may be one of the more perfect yard games on the market:
What makes CupCheck damn-near perfect:
- It’s lightweight and portable – no need
- The unattached pieces (cups, disc) can be easily replaced or substituted if you can’t find the originals
- It requires no real skill and doesn’t necessarily reward strength
- Cups flying off these poles are impossible to predict, basically negating the advantage of experience
- You’re always doing something, playing offense and defense; no standing around
- Games move quickly
Then there’s the story behind the game. It was originally laughed off, then embraced, then adored, then invested in enough where world-class athletes felt it had a place in homes everywhere.
Then these athletes, multi-millionaires with no real need to become entrepreneurs or inventors of a yard, persevered through shattered expectations, manufacturing nightmares and then a pandemic to stick with a product they genuinely believe in.
Now, best of all, the hard work has been rewarded with a great product that’s creating memories for people the same way it did for this group of teammates and friends.
Jepsen and his friends have made their rounds on local TV stations, MLB Network and even on Forbes.com to talk about CupCheck, but those stories focus on the fame factor of pro athletes banding together for a good time. I don’t think that’s the ultimate story for CupCheck.
This wasn’t a group of baseball players that launched something on a whim … this is a group of friends, who happen to play baseball, that found something special and decided to share it with the world. They struggled at times but stick with it and created shared the joy of this game. And that’s what CupCheck is about. That’s what a tailgating lifestyle is about — sharing what you love with a community you love even more.