“Bring a gift for a stranger.”
Not the kind of request you’d expect when registering for a bike race, but according to event organizers Andy Chasteen and Lauren Pickman, Rule of Three [RO3] isn’t really about the race.
Chasteen, who humbly refers to himself as “Head Idiot In Charge,” is responsible for the genesis of RO3, a one-of-a-kind event that combines road, gravel, and singletrack bike routes throughout Northwest Arkansas. The man with a mullet, who hands out high-fives like Halloween candy, considers RO3 a platform for spreading kindness and fostering community.
“A bike event is a very trivial thing in the grand scheme of the world we live in, but I think a lot of people are looking for meaning and belonging,” he said. “These bigger, serious gravel events are important for the growth of the sport, but we're completely different. I don't care who finishes first, I care if everyone finishes.”
From the very beginning, Chasteen and Pickman wanted to make it clear that RO3 is about having fun, and what better way to do so than to put the boss in a costume?
“Lauren and I, and all of our volunteers, dress in wacky outfits,” Chasteen explained. “The second someone pulls up thinking they're about to be serious and race, they see the people who are putting on the event looking like buffoons. What that does is it lowers the temperature so nobody’s as nervous. We have to lead that charge as promoters so everyone feels the same way.”
Chasteen isn’t new to throwing funky, yet no less challenging, outdoor sporting events. Before RO3, he founded 24 Hours of Horseshoe Hell [24HHH], a five-day rock climbing festival held annually at Horseshoe Canyon Ranch in Jasper, Arkansas. With vibes akin to Burning Man, 24HHH is (allegedly) the longest-running rock climbing event in the world. Balancing Chasteen’s right-brained strengths, Pickman is RO3’s boss lady with a left-brain flex. She hails from the East Coast and is recognized as one of the founding members of Women of OZ.
“I organized monthly group rides of 150 women, so Women of OZ set me up for creating these events, which led me to the opportunity with RO3,” Pickman shared. “Andy and I put our strengths together and launched Rule of Three. His expertise is marketing and branding, and I focus on the fun details and operations.”
“She's the opposite of me,” Chasteen added in jest. “She's responsible, and detailed, and organized, and I'm none of those things.”
RO3 sold out in its first year, and word quickly spread. Now, the event welcomes people from almost every state and, most years, five to seven different countries are represented. This diversity of attendance leans into Chasteen’s founding mission to foster community, going back to their request for participants to bring a gift for a stranger.
“It can be whatever you want it to be,” Pickman explained. “You just go up to someone and give a little gift. By doing that, you're creating an authentic moment of connection; it has affected a lot of people.”
While RO3 emphasizes fun over performance, this ethos isn’t all that sets the event apart. For those who aren’t familiar with the format, participants are challenged to complete their chosen 50, 100, or 200+ mile route, solo or in a team of three, but they can only use one bike. There’s no swapping setups between tarmac and singletrack; no maintenance crew to fix your flat; no support team to replace muddy lenses or wet socks. RO3 is an obstacle as dynamic as it is challenging…but fun, don’t forget fun.
As Chasteen’s RO3 poem reads, “You get a healthy dose of tarmac, gravel, and singletrack. But come prepared, this course bites on the way back.”
Even with a good-time tone set, the majority of RO3 participants have signed up to do something very difficult. “These courses are not your typical gravel rides,” Pickman said. “Incorporating a decent amount of singletrack really adds another level of challenge to the day. It’s an extremely fun day but equally as challenging. We always say, ‘Winners get to brag, everyone else gets the swag.’”
Speaking of swag, another differentiator for RO3 is its partnership structure - there isn’t one, kind of.
“We don't ask anyone for sponsor cash,” Pickman added. “If you want to be a part of our event, we're not going to charge you, but you have to bring something of value. And because of this, sponsors tend to contribute really great items to the swag bag or get really creative with checkpoints and quirky prizes, and raffles. Every year, it gets better and better.”
Instead of a presenting sponsor, the duo chose to emblazon the finishing line with the names of every person who has signed up for the event. “The sponsors of our event are the people who are paying the entry fee,” Chasteen said. “Most race events have their sponsors on the finish line, but we have the names of our riders, which I think is cool.”
Riders and spectators alike can expect something new from RO3 every year, including sponsors and routes, though routes aren’t released until just before the race. With a little insight from Chasteen, however, we learned that RO3 2025 will activate partner cities like Pea Ridge and Sulfur Springs, and possibly incorporate elements of last year's race, only in reverse.
Throughout this charming non-race race, participants will push themselves mentally and physically. They’ll wrestle a few flats and definitely smell interesting, but once they’ve crossed the finish line into the welcoming after-party crowd, the pride of achievement and memories made make the juice worth the squeeze.
"I don't care who finishes first, I care if everyone finishes.”
"This isn't serious. We're here for fun."