We left Florida in a wrapped Sprinter van with a fairly simple idea: drive across the country and talk to people who play pickleball.
Not necessarily pros or influencers. Players.
We wanted to see where they play, why they play, what they wear, and what they think about our shoes when we're standing right there to hear the answer. I was also figuring out how to document all of it. We had a DJI Osmo Pocket, the little camera all the vloggers recommend, and DJI mics. Compact. Supposedly easy. I was still learning which buttons did what. IYKYK.
There are easier ways to conduct market research. Most of them have air conditioning.
Naples: What the Court Tells You
Our first real stop was Naples, at the US Open Pickleball Center, where the courts were already hot enough to remind us that August in Florida may not have been the most sensible place to begin a cross-country road trip.
We met John Dearstine, a coach and court monitor who had built a new life around pickleball in Florida. Then we met Alan, a serious, high-mileage player who had been putting a lot of hours into his Court2s.
He liked the shoes, but felt the outsole was wearing faster than he wanted. We hear this from time to time, particularly from aggressive players who play a lot. It's not something we hear with the same frequency from our core customer, but it's feedback we take seriously.
It also goes directly to one of the choices we made when we built Court2.
We use natural rubber in the outsole because of the grip and court feel it provides. The tradeoff is that a softer natural rubber can wear faster than a harder, less grippy material, particularly for an aggressive player logging a lot of hours on hot outdoor courts in a Florida summer.
There is no free lunch in footwear design. The question isn't simply how to make an outsole last as long as possible. It's how to balance durability with traction, weight, flexibility and feel.
Alan's shoes gave us a chance to look at that balance in the real world. We compared his wear, talked about how and how often he plays, and invited him to wear-test some of our future designs.
That's exactly the kind of conversation we came on the road to have.
St. Pete: The Cadillac Cruiser
A few hours north, we arrived at St. Pete Athletic. One of the owners, Graham D'Amico, had never worn our shoes. We gave him a pair, and his first reaction was immediate:
“These are the Cadillac cruisers of shoes.”
Then we started touring the club. About eight minutes later, without us asking, Graham started talking about the shoes again.
“These are comfy. These are my kinda shoes.”
Then he got more specific. He could feel the support through his arch and something unfamiliar underneath his toes. We told him it was the toe bar.
“A toe bar, yes. I've never felt that before, but I like it a lot. I honestly feel it.”
Men's Pickleball Court Shoes, PB5 Court2 | White-Black
$129.00
Dominate your pickleball matches with the style forward, PB5 Court2, a new era of high-performance technology engineered for a responsive ride. Built with Dynamic Stability Assist™, these Light-weight shoes are packed with features to deliver the traction and control needed… view
That interested me more than a generic compliment about comfort. The footbed was designed with a deep heel seat, arch support, metatarsal dome, and toe bar. Graham hadn't been briefed on any of it. He didn't know what he was supposed to notice.
He just noticed it. Then we played.
Graham was my partner and a very good one. After a good shot, he'd call out, “Partner!” If a ball looked out of reach, he'd tell me, “Got you,” and go get it.
There is something oddly bonding about a person you met an hour ago suddenly calling you partner.
And I will give this club it's own blog post with more details and pictures. The club is beautiful. I wish I lived close enough to join. 
The Villages: The Game Isn't Really the Point
The next morning, we drove into The Villages. By 8 a.m., it was already hot. We met Jana and her friends at the courts and spent the morning learning how pickleball fits into life at The Villages. Victoria Radnothy from pickleball.com joined us to learn more about the pickleball scene we'd all heard about.
The more interesting conversations weren't really about the game. People kept describing pickleball as part of how they had built a new life. One man had gone through some life changes, discovered The Villages, and moved there. Pickleball became his social foundation. One of the women described life there as something close to college without the homework. There was always a club to join, someone to meet, somewhere to go.
And, since everyone asks, we asked about the rumors. We were assured they are not true. Eventually, the Florida heat won, and five of us piled into a golf cart for a tour.
The golf carts turned out to be more than transportation. The Villages has its own network of golf-cart roads, tunnels, and bridges connecting neighborhoods, recreation centers, restaurants, and town squares. You could see how the infrastructure itself encouraged people to get out of their houses and into the community. You weren't just driving somewhere. You were likely to see people you knew along the way.
We had started this trip talking a lot about pickleball as a sport. I was already starting to think that might be too narrow.
Pensacola: In the Wild
In Pensacola, we had our first real “in the wild” moment. Men walked into Portside Pickle already wearing PB5star Recovery Slides. We hadn't invited them. We hadn't outfitted them for a shoot. They had bought them and were wearing them.
For a small brand, seeing your product unexpectedly on a stranger still feels a little improbable.
Wilbur, one of the owners, particularly liked our Après Pickleball positioning for the slides. The thing you put on when the match is over.
Then our visit turned into an actual activation. Kelli, who oversees operations at Portside, jumped in to help. People gathered around the table and started trying on shoes. More people came over. We were pulling sizes from the van, and customers were buying.
I had brought along a graphic I'd made explaining the movement differences between tennis and pickleball and why footwear designed around the game matters. Wilbur loved it, so I sent it to him to use.
Pickleball footwear is still a young category. A lot of people simply wear whatever athletic shoe is already in the closet. Part of building the category isn't telling people our shoe is better. It's explaining why a different sport requires a different shoe.
Before we left Pensacola, I also perfectly parallel parked our giant Sprinter downtown. Alex was genuinely impressed.
I may have been more pleased by this than some of our actual business accomplishments.
Buc-ee's, Water, and the Road to New Orleans
There had been a minor road-trip disagreement developing by this point.
I drink water. Plain water.
I had been digging through our cooler looking for some and discovered flavored sparkling drinks, flavored waters, and various other things that were technically mostly water but were not, in my opinion, water.
“Where's the water?”
Alex pointed to the flavored cans.
No. Water.
It turned out Alex doesn't really believe in plain water. She hates it. This seemed like useful information to have learned before setting off across the country together in August. So when we made my first-ever stop at Buc-ee's on the way to New Orleans, I was genuinely happy to discover cold bottled water for $1.58.
Alex had described Buc-ee's to me as the Disney World of gas stations. The first thing I noticed wasn't the size. It was the smell. Standing near the gas pumps, I didn't smell gasoline. I smelled funnel cake, or something fried and sweet.
Inside felt a little like an elevated Walmart with a food court dropped into the middle. Barbecue, a wall of beef jerky, enormous beverage sections, Halloween decorations, clothes, desserts and piles of country-themed things I couldn't imagine needing.
My cynical side saw a lot of future landfill. But they had $1.58 water, so Buc-ee's and I were on good terms. They also sold pickleball paddles.
No pickleball shoes. An obvious oversight.
Somewhere between Pensacola and New Orleans, we also pulled over at the Alabama and Louisiana state lines to film ourselves running past the welcome signs. This had become a recurring bit for a video we were making as we crossed the country.
Alabama made it easy. Nice sign, rest stop, grass, nobody had to risk getting flattened by a semi.
I would come to appreciate this more as the trip continued.
We got back into the van and headed west. This was always supposed to be a listening tour. Talk to players. Watch them play. Put shoes on your feet and see what happens. My daughter goes to Cal Poly, whose motto is “Learn by Doing.” I had more or less borrowed it for the trip.
List of Pickleball Clubs visited on this leg of the journey
- USOP National Pickleball Center in Naples
- St Pete Athletic in St. Petersburg
- The Villages
- Portside Pickle
