Pickleheads

By Matthew Schwartz

December 3, 2024

Without the Pickleheads court finder app, Lorraine Rupper might still be driving.

A competitive, 5.0 player, Lorraine had a longtime goal of playing at least one pickleball match in all 50 states. It was the top item on her bucket list. The 59-year-old middle school guidance counselor from Orem, UT, had knocked off 14 mostly western states over the past few years. Lorraine set out in June to finish her quest while on summer vacation. She had her work cut out for her because she was driving alone.

“Pickleheads was my go-to app for everywhere I went on my trip,” Lorraine told me.

And in June, Lorraine went places. In 19 days, she played at least one pickleball game (and usually several) in 36 states. She put more than 8000 miles on her 2014 Honda Civic (I chronicled her trip in this blog from October.)

“The Pickleheads app saved me so much time and energy in reaching my goal of playing pickleball in every state,” Lorraine said.

That comment is music to Brandon Mackie’s ears.

Mackie co-founded Pickleheads with two friends in March 2022 and is its COO. Pickleheads is the leading app for finding places to play, with 800,000 monthly users, 322,700 registered users and 19,200 pickleball locations listed.

“The original vision came from my own experience as a player in Los Angeles,” Mackie tells me from his home in Tempe, AZ. “I was amazed at how difficult it was to find accurate court information. I remember scrolling through hundreds of Google Places, images of a park, and wondering if there was actually pickleball there. Like is it worth sitting in 40 minutes of LA traffic to find out the courts are in fact not set up for pickleball?”

The court finder put Pickleheads on the map (pun intended).

“Our court finder was our first ever feature and it’s the one we built the entire company on,” Mackie says. “If you think about it, finding a court is the first step in the player’s journey and given our goal is to own the whole player journey, it was the perfect place to start.”

 Pickleheads contains more content besides the court finder feature. There are virtual clinics, blogs on the latest pickleball news, and recommendations on paddles, balls and nets.

Like many pickleball entrepreneurs, Mackie’s life BP (before pickleball) is interesting. Born 36 years ago on Long Island, NY, his family moved to Northeast Ohio when he was five and Savannah, GA, when he was 14. His parents were big tennis fans and Mackie played number one singles in high school. He went to Georgia Tech where he studied chemical engineering, graduated in 2011 and landed a job in Houston as a chemical engineer.

“I didn’t love it, to be honest,” Mackie says of his first job.

He quit chemical engineering and got into the stock market. He wrote an investment blog and was the financial operations analyst for Soylent, the meal replacement company. Six years ago he founded Keto Farms (now Earthside), which makes keto and low carb snacks. He started up other companies and sold them all before investing in what he knew was the next big thing: pickleball.

“I had just sold my last company, I really liked working with my co-founders and it just felt right to dive in. Of course, we could never have predicted how fast the sport would have grown from there [two years ago].”

Asked if he did well enough financially from his earlier businesses to take a hit with Pickleheads, Mackie says, “I wish I could say that! My past ventures gave me enough cushion to take a risk with Pickleheads but I’m still hungry to build a big business and have a life changing outcome.

“Pickleheads is just now in a place to pay my bills. I took no salary for the first year and a half while we got it off the ground.” Regarding the app’s growth, Mackie says, “It’s been tremendous. We have grown our user base 10 times year-over-year.”

Good timing for Mackie because he and his wife of 14 months have a nine-week-old baby boy.

Pickleheads makes its money from affiliate sales. “When a player buys gear from our content and recommendations, we get a commission from the manufacturers,” Mackie says. “It’s grown to be a very significant revenue stream.”

            Running the Pickleball apps and website leaves Mackie time to play only twice a week. He used to play a lot more. As a former tennis player he picked pickleball up quickly and has a DUPR (Dynamic Universal Player rating) of 4.5.

“Pickleball is just FUN!,” Mackie exclaims in an email. “It’s hard to describe to people outside of the sport but it just has this very fun and social vibe. What I am doing doesn’t even feel like work and I always say I can do it for a very long time.

As in his previous businesses, Mackie has lofty goals for Pickleheads. “We want to be THE app for pickleball,” he says. “The one platform that is a must-have for all players. The more games and players that use Pickleheads, the more valuable the platform becomes for all. We’ve always said our vision is that every pickleball game starts on Pickleheads. That’s what we’re shooting for.”

Thoughts of the week, not all pickleball

• A postgame brawl marred unranked Michigan’s shocking upset of number 2 Ohio State last Saturday. It happened after a Michigan player tried planting the team’s flag on the Ohio State logo at midfield. Punches were thrown, players and staffers were bloodied, and police used pepper spray in an attempt to diffuse the situation. As the excellent Fox Sports play-by-play man Gus Johnson said, it was disrespectful of Michigan to try to plant the flag. You already won the game, show some class. That doesn’t excuse the Ohio State players who threw punches. The Big Ten conference issued $100,000 fines to both schools.

• If you’re a college football fan I hope you saw the Georgia Tech-Georgia game on Black Friday. A classic that went eight overtimes. Georgia scored 14 points in the final four minutes in the 4^thquarter to tie it and about an hour later won, 44-42.

• Regarding the “shhh” sign that football players make when they score a touchdown on the road to quiet the home team’s fans, lately I’ve seen many college home team players do that. Cracks me up. They’re telling their cheering home fans to be quiet. Don’t these guys know where they’re playing?

• Speaking of unaware football players, last Friday I’m watching my alma mater, the Ohio University Bobcats, blow out Ball State. A Ball State player catches a TD pass to cut the Cardinals deficit to 42-20 with 2:40 left in the game and he performs a celebratory dance in the end zone. Not exactly a team-oriented move, rather a “look at me celebrating even though we are getting blown out” move.

• I’ve noticed the same trend you probably have at pickleball rec play: More players than ever are bangers who can’t dink and don’t have a third shot drop. If you have a solid soft game, avoid hitting pop ups and are patient, you’ll beat bangers more often than not.

• Since writing my previous sentence, another 240 pickleball paddles have been released. Of course I’m kidding. Only 200 have dropped.

A reminder that Hudef’s Black Friday sale runs through Friday. You will get 35% off the regular price on The Mage Pro Gen 2, Viva Pro Gen 3 and the Luxury Gen 1 paddles. They will cost only $110.49 using discount code HBF-MS35 at check out. They regularly cost $169.99.