Land Paddling Pioneer: A Conversation with Timmy P
In this intimate conversation, we sit down with one of the original innovators in land paddling to discuss his journey, achievements, and the growing community around this unique board sport.
The Skateboarding Roots
Timmy P's journey into land paddling began with his early love for skateboarding. Growing up as one of seven siblings, he was motivated by his athletic older brothers and sisters.
"I played all the sports that most kids played in the 60's & 70's; baseball, football and basketball. I was just kind of good at everything I tried," Timmy recalls.
His skateboarding journey began in 1974 at age 14 after watching a freestyle skate competition on TV. Amazed by what he saw, he purchased a plastic Coyote 2 skateboard from a local dime store and began practicing the tricks he'd seen on a small concrete area at his house.
"It was something I could do for hours, trying to perfect the freestyle moves. It was an individual sport that I seemed to have talent for."
Over the decades, Timmy expanded into various action sports including water skiing, wakeboarding, surfing, snow skiing, snowboarding, and mountain biking. But skateboarding remained his constant passion, approaching now 51 years on the board.
The Transition to Land Paddling
The evolution toward land paddling came naturally as Timmy aged.
"As an aging skateboarder, I began to get injured trying to skate the vert ramps and bowls like a young guy. In my mind I could do it, but my body was starting to suffer."
Having built skateboards for years—mainly reproductions of 80s boards that older skaters wanted, along with cruiser boards—Timmy began skating purely for exercise, which eventually led to paddling as a more complete workout.
Achievements and Milestones
Though humble about his accomplishments, Timmy has achieved impressive results in the land paddling community:
- 3rd place podium finish in 2016 behind Deejay and Chip Walter
- Team podium finishes in 2017 & 2018 Ultra Skate with Ed Francavilla
- 1st place in Push/Paddle at 2019 Ultra Skate
- 3rd place in Push/Paddle during the rainy 2020 Ultra Skate
- 2nd place behind Jeremiah Pascua in Push/Paddle at 2022 Ultra Skate
- Recipient of the Live Like Anne Palmer Award
- MVP Skater out of 16 countries in the 2023 Skate IDSA Virtual Series
- Course record for 60+ Paddle category at Ultra Skate 2025
Beyond competitions, Timmy values the relationships formed through the sport. "The most rewarding thing that paddling has brought to me is the relationships made with people from all over the world. They have been a joy and blessing in my life!"
He particularly treasures memories of skating adventures with fallen long-distance skating greats: Anne Palmer, Jeff Crowe, and Raymond Tan.
Community Contributions
Timmy has used his board-building skills to contribute to numerous charitable causes:
"I have enjoyed contributing to and building boards for raffles to benefit these charities: St. Jude Children's Research Hospital, Shriners Hospitals for Children, SHRED (Skaters Helping Realize Extraordinary Dreams), the Dana Farber Cancer Institution, and the Live Like Brent Foundation. I also had the privilege of building a paddle skateboard for a child with Spina Bifida."
While describing himself as a "lone wolf" in his local area, he enjoys opportunities to share his passion: "While skating on a trail, I often get asked what I am doing. I enjoy talking to people and sharing my passion with them."
He hopes to inspire skaters of all ages: "If Timmy P can do it, they can as well! Maybe they'll see my age and realize that they too can step on a board and paddle off into the sunset."
Here's a trail review if the Swamp Rabbit Trail, one of Timmy's favorite spots to ride. Rain or shine, it's still super fun.
Equipment Innovation
Timmy's approach to equipment has been practical and focused on performance. His early paddles were made on a homemade wood lathe with a rubber mallet tip. After experimenting with other materials like lacrosse balls, he eventually found commercial options that worked, though he maintains specific preferences.
"I love the adjustable paddles for casual skaters, but I still prefer the one-piece paddle for myself. I think most people who are perhaps higher skilled at paddling most likely prefer the one-piece."
His board designs have earned praise from other respected skaters. "I had Jeff Vyain (Pantheon) tell me after riding my skinny tail board that it was the fastest pumping board he had ever been on!"
For Timmy, building boards is therapeutic: "My builds are just builds out of necessity, but I do enjoy making them for the requests that I get as well. Building boards is therapeutic for me! I've been fumbling around in my shop for 25 years building boards."
He's particularly proud that some of his boards made it onto a World Record Team, though he modestly attributes this more to the athletes than his designs: "Those amazing athletes could literally ride anything though, so I don't think it was my boards, but I do think the flex and return of energy aids in fast pumping."
The Evolution of Land Paddling
When asked about terminology and the evolution of the sport, Timmy acknowledges the role companies like Hamboards have played in making the activity known worldwide.
"When I talk with people and they ask me what I'm doing, I usually say Land Paddling or SSUP. Most people understand what Street Stand Up Paddle is unless they don't know what SUP on the water is."
He's quick to credit others for popularizing the sport: "Thanks to guys like you Don for getting out there and running the roads, pushing the product and for having made paddle skateboards a household name around the world."
Timmy sees companies like Don's as crucial to bringing more people into the sport: "If you can get their feet on the board and the paddle in their hand, they can get that good feeling. Thanks again for continuing to improve the industry so more people will show up at events."
What Timmy's friends have to say about him
Like many board sport enthusiasts, my journey began with traditional skateboarding as a kid. While I wasn't the standout among my friends, that early experience planted a seed that would later flourish when I discovered larger surf-style skateboards. The game-changer came when I purchased my first "street sweeper" – that's when my passion truly ignited.
Everything changed after meeting Timmy at Ultra. I'll never forget my first Ultra Skate event, watching in awe as this older guy effortlessly skated circles around me. I immediately thought, "That's who I want to be like." Little did I know it was Timmy himself – and remarkably, he's still skating circles around me today!
What makes Timmy special isn't just his incredible skill, but his meticulous approach to his craft. Each board he designs serves a specific purpose, with thoughtful details that make them uniquely functional. His eye for detail translates into boards that aren't just equipment – they're purpose-built tools for specific skating experiences.
Beyond his craftsmanship, Timmy's relentless energy keeps our entire community motivated. He consistently posts his impressive 20-mile sessions on social media, inspiring everyone in our circle to get out there and log their own miles. His dedication is contagious.
A quote I heard recently perfectly captures what Timmy embodies: "Maximize the dash. Be old and be Epic." That's exactly what he's done for our sport – created something truly epic. Though rumors suggest this might be his final year at Ultra, I'm holding out hope for one more chance to watch him skate circles around me, continuing to inspire the next generation of land paddlers just as he inspired me.
Looking Back and Forward
Despite his significant contributions, Timmy is humble about his role: "Don, I don't feel like I'm a pioneer. Some of the first videos that I watched of Land Paddlers were of 'Skeightsup' Sanjuan and Deejay. I received some encouragement from Dee on one of the forums back in 2012 and it kind of got me pumped! I really look up to those guys."
He's excited about the industry's growth and hopes that his example might inspire others: "I do believe that some people can look at me and say, 'If that old fart can get out and get moving, then so can I!'"
Five Decades of Skateboarding Joy
Reflecting on his skateboarding journey spanning five decades, Timmy values both the individual nature of the sport and the community connections it creates:
"Although I still consider it an individual action sport where you control what goals you want to achieve, the best times are when we can get together with friends to share the sport we love no matter the discipline."
From freestyle competitions in the 70s, to hauling a portable skate park around in the 80s, to taking 70 kids to Kona Skatepark in Florida in the late 80s and 90s, to vert ramp and bowl riding in the 90s and early 2000s, and finally to skating for exercise around 2010, skateboarding has been a constant source of joy.
"No matter what kind of rolling around on a skateboard that I have done, it has supplied me with some of the most memorable and happiest times of my life to just to be able to share what I love with others!"
This interview captures the spirit of Timmy P, whose passion for skateboarding evolved into pioneering efforts in land paddling, building a community, and inspiring others through his athletic achievements and genuine love for the sport.