Become a Member

Get access to more than 30 brands, premium video, exclusive content, events, mapping, and more.

Already have an account? Sign In

Become a Member

Get access to more than 30 brands, premium video, exclusive content, events, mapping, and more.

Already have an account? Sign In



The Climbing Q&A: Jimmy Webb

Jimmy Webb would be the last person to tell you that he’s sent more V16s than almost any other American. Credit that humility—and the work ethic that earned him those ticks—to his Tennessee roots.

Lock Icon

Become a member to unlock this story and receive other great perks.

Already have an Outside Account? Sign in

Outside+ Logo

Intro Offer
$3.99 / month*

  • A $500 value with everything in the Print + Digital Plan plus 25+ benefits including:
  • Member-only content on all 17 publications in the Outside network like Rock and Ice, Outside, Backpacker, Trail Runner and more
  • Annual gear guides for climbing, camping, skiing, cycling, and more
  • Gaia GPS Premium with hundreds of maps and global trail recommendations, a $39.99 value
  • Outside Learn, our new online education hub loaded with more than 2,000 videos across 450 lessons including 6 Weeks to Stronger Fingers and Strength Training for Injury Prevention
  • Premium access to Outside TV and 1,000+ hours of exclusive shows
  • Annual subscription to Outside magazine
Join Outside+

Digital + Print
Intro Offer
$2.99 / month*

  • Annual subscription to Climbing magazine, and a coffee-table edition of Ascent.
  • Access to all member-exclusive content on
  • Ad-free access to
Join Climbing

*Outside memberships are billed annually. Print subscriptions available to U.S. residents only. You may cancel your membership at anytime, but no refunds will be issued for payments already made. Upon cancellation, you will have access to your membership through the end of your paid year. More Details

Jimmy Webb controlling the swing on Lucid Dreaming (V15), Grandpa Peabody Boulder, Bishop, CA. He made its fifth ascent in January 2020.Kevin Takashi Smith

Jimmy Webb started pushing his boundaries by pushing those of his parents. The Maryville, Tennessee, native—now 32 and a professional boulderer based out of Sacramento, California—grew up running around creeks and broadleaf hollers in the Appalachian foothills. “I always had my mom or dad freaking the hell out because I was way up in some tree and they didn’t know where I was,” he says.

Sometimes it was a tree. Sometimes it was the limestone bluffs along the river near Webb Hill, his grandparents’ 10-acre farm south of Knoxville. Sometimes it was stuttering, 80-foot cliff jumps into water-filled abandoned quarries—apropos, given that Webb has won the Psicobloc deep-water soloing competition in Utah four times.

Webb has spent the past decade slowly carving a name through highball bouldering, difficult redpoints, prolific hard flashes, and technical skill. In the past three years, he’s sent the Squamish classic Dreamcatcher (5.14d); the highballs The Healing (V14, 26 feet) and Livin’ Large (V15, 30 feet) in South Africa’s Rocklands; and the V16s Creature from the Black Lagoon in Rocky Mountain National Park and Sleepwalker (FA) in Red Rock’s Black Velvet Canyon. In the past year alone, he’s nabbed first ascents of Ephyra (V16) in Chironico, Switzerland, and Virgo (V15) in Lake Tahoe, and repeated the Paul Robinson highball Lucid Dreaming (V15, 50 feet) in Bishop. In the past six months? Two more V16s, put down within a month of each other in Chironico (Giuliano Cameroni’s Poison the Well and Shawn Raboutou’s Off the Wagon Sit).

“Jimmy’s always been a natural at everything he’s done,” explains Jimmy’s dad, who works as a cable lineman in Townsend, Tennessee. (He’s James Webb II; our Jimmy is James Webb III.) Before climbing, it was baseball, basketball, soccer, skateboarding. By age 16, Webb had a six-foot frame inherited from his dad, as well as mental and physical strength he credits to his grandfather, a lifelong farmer.

Webb’s parents split when he was a toddler. He lived the first 17 years of his life with his mother, an accountant, in Maryville, before moving in with his dad in Townsend. As an only child, Webb whittled away the hours running around his grandparents’ farm. The woods were a jungle gym, a training ground, a refuge. They sparked what he calls an early drive to explore the unknown—and a burgeoning fearlessness.

Recalls Webb II, “One time, we were in New Orleans, going down the Mississippi on a paddleboat, and we turn around and Jimmy’s jumped over the railing and is hanging out over the paddle. We had to go out and grab him. Jimmy was about 11 then.”

Webb was first introduced to climbing at age 16. A girl he dated was on the Maryville High School climbing team, and she brought him along to practice in nearby Knoxville. The movement, the problem-solving—everything clicked. Webb quit his other sports—despite the promise of college soccer scholarships, and stern protests from his father—and started attending climbing practice regularly. When his coach announced a standing invitation to the Obed on Sundays, Webb showed up every week at the designated rendezvous, a gas station halfway out of town. Often, he was the only team member who did.

Through the team, Webb also met Jeremy Walton, who soon became his primary climbing partner. In high school, Walton got Webb a job at a local mom-and-pop dry cleaner in Maryville. There, Webb rang up customers, handed off pressed collared shirts, and watched the clock until 4 p.m. when he and Walton would hit the road for the Obed, over an hour away. They’d get in around sundown and boulder through the night. In those first few years, Webb didn’t train; he didn’t need to. Within a year of first stepping foot in that Knoxville gym, he’d sent a V8.

Webb on the iconic (and rarely repeated) Squamish climb Dreamcatcher (5.14d), which he sent in September 2018.Kevin Takashi Smith

After a brief stint at Pellissippi State Community College in Knoxville, Webb dropped out to pursue climbing full-time. His dad told him he’d never make it, but he didn’t care. He threw himself into bouldering. For 12 years, he lived at the heart of the Chattanooga climbing scene.

The community had its rules. In the Appalachian woods, the rock was hard to find, and locals held the keys. To gain access, you were expected to wait for an invite. The prevailing etiquette also included asking permission before drawing attention to an area, whether via posting a photo on social media or by announcing a new V13, a grade rare in the region. Webb connected with the strict ethic.

“Jimmy was naturally humble, and that goes a long ways [toward getting accepted in the community],” says Luis Rodriguez, who founded the Tennessee Bouldering Authority (TBA). He managed the gym while Webb worked there as a setter and coach. Rodriguez soon became a mentor for young Webb, whom he remembers as a conscientious student of climbing history, mature beyond his years, a selfless coach for the youth team, and a climber unfettered by image—Webb often dressed in ragged, duct-taped jeans.

“I first met Jimmy in Little Rock City,” says Rodriguez. “I remember seeing him crush this problem King James (V10)—which was not named after him, by the way—and thinking, ‘This kid’s on a bigger level, a world-class level.’”

Webb started racking up FAs, but never let it go to his head: In Chattanooga—where pro climbers are rare, and most climbers have full-time jobs—you can’t build an ego because you can’t get away from the mirror long enough; someone’s always holding it up for you, reminding you of your roots, reminding you of your humble beginnings. “In the South, they talk so much shit,” jokes Webb. “They don’t let you stay on your high horse for too long.”

Webb garnered further notice during a three-month stint in Hueco Tanks in 2008. There, he dispatched Li (V13), his first of the grade, and Crown of Aragorn (V13). “That trip was a major breakthrough,” Webb says. “It was the first time I realized I was capable of climbing harder.” A few years later, Webb visited South Africa’s Rocklands where he ticked Golden Shadow (V14), and turned heads with flashes of The Vice (V13), Sky (V13/14), and a handful of other V13s. Then, in 2013, he won his first Psicobloc. “He showed the world you can be a humble kid from a tiny, little town and still take it to the upper echelons,” Rodriguez says. “He helped put Chattanooga on the map.”

Watching Webb climb is almost grotesque. He’s pure power. He’s fast and dynamic. He’s precise. His muscles have muscles. Call it genes or a gift from the gods—despite all those double-digit numbers, you’ll rarely find Webb in a gym. “Jimmy is a burly climber,” says Daniel Woods, noting Webb’s supernatural proclivity for compression blocs. “He’s also a genius with movement and body awareness.” Woods and Webb have been friends since they first met in Hueco Tanks about a decade ago. “Just his presence gets me stoked to try hard,” Woods says. “I would say we have a friendly competitive chemistry between us.” Plus, they’re both skaters.

Most recently, Webb made the FA of one of America’s five V16s, the desperate Sleepwalker, a 45-degree-overhanging, dinner-plated bloc in Red Rock’s Black Velvet Canyon. Webb climbed the problem—originally attempted by Nalle Hukkataival—in December 2018 after 11 days of effort. (It has had three repeats: by Woods in January 2019, Hukkataival in February 2019, and Drew Ruana in January 2020.)

Webb was in Vegas with Woods and their mutual friends Keenan Takahashi and Kevin Takashi Smith. During the day, they worked the boulder. At night, they shared an Airbnb, cooked dinner, watched skateboarding videos, talked shit, and drank wine. Usually, this is a recipe for productive sessions, a laid-back atmosphere, and sends all around. But Sleepwalker was different. “You could almost say I was attached to the grade, but there wasn’t one,” Webb says. “I was attached to the idea of succeeding at what would be the hardest thing I’ve ever done.”

The problem begins by standing into and matching on a powerful undercling, followed by a right-hand reach into an eroded wrinkle. You then bump your right hand up to a full-palm sloper rail, paste your feet, and inch your right tips into a narrow slot. From there, you have to punch up and left to a miniscule pinch. The move is massive and the hold terrible. Your feet cut, and you have to hang on just long enough to swing your left foot into an overhead toehook to slap the finishing jug.

Chilling with his dog, Oreo, at the Buttermilks, Bishop, CA.Kevin Takashi Smith

After nine days on the boulder, and with only a few days left in the trip, Webb’s mindset took a turn. He didn’t want the send anymore; he needed it. “I kept thinking, ‘I should have done this by now,’” he says. Frustrated and overwhelmed, Webb saw his progress kick into reverse. He started falling lower and lower: “I had hit rock bottom.”

That night, Webb was pensive. What am I even doing here? he wondered.

But later, cooking dinner and trading jabs with friends, he was suddenly struck by how similar it felt to all those years in his early 20s—driving to the Obed at dusk, drinking beer on summer nights, hanging with friends in the woods. Webb resolved to forget about the tick and instead focus on doing the moves, and doing them well. His new goal wasn’t to top out, but to learn one new thing about the route each session.

Two days later, he sent on his second try of the day. At the jug, a roar ripped from his throat. It was a roar of triumph. Of relief. Of gratitude.


Why Bouldering?

Jimmy Webb: I’m a very aesthetically inspired climber. Big cliffs with a bunch of routes and chalk and bolts and people—that turns me off. I get psyched on boulders because it’s easier to find these big, beautiful, singular lines with nothing next to them. The other draw is the simplicity. When I was young, I could just go out with friends whenever we wanted. Later, when I moved to Chattanooga, the people I met became the big inspiration for me. That crowd was just so fired up
on bouldering.

How do you find new zones?

I spend an absurd amount of time on Google Earth. I look for potential new boulders, then try to find photos from hikers who have passed by them. Then I map out a route. Once I’m there, I like to take my time, walk through the field of blocs, and thoroughly search through them. I look for lines where I turn a corner and just freak out with excitement. Those are the ones I work first.

How do you determine what’s on the cutting edge of possible, versus actually unclimbable?

It’s a fine line. The first thing I do is rappel and look for holds and make sure the thing actually goes. Then I bring the brushes and start cleaning and sorting out a method. It has to be a really badass, inspiring line to keep your interest, and you have to have a certain amount of faith to continue literally bashing your head against a wall for days on end. There are definitely projects I’ve tried and never touched again.

What’s your proudest send?

Maybe Livin’ Large [a 30-foot Hukkataival V15 established in 2009] in Rocklands, South Africa. That was one of the most challenging boulders I’ve done, both physically and mentally. The conditions were hard to get, so you had to wake up early. It’s physical and technical, and then around 30 feet, you’re climbing a V9 or V10 technical arête. You just don’t know when you’re going to eat shit. It took me 12 days to control my fear and ultimately succeed.

What do you do for training?

Webb: I mostly spend my time outside, but when I’m in the gym, I make the most of it. I tend to focus on my weaknesses. Finger strength has always been a struggle for me as a slightly heavier climber. So I typically focus on crimp boulders, campus boarding, and loads of core. A typical sesh is around three hours.

Given your Southerner’s aversion to spray, how have you supported your climbing?

Webb: For the longest time, I just did odd jobs and lived as cheaply as possible. I was a pizza-delivery guy until my old Honda Civic broke down. I was a line chef at Buffalo Wild Wings. I worked as a setter at the Tennessee Bouldering Authority. Anything I could do to make enough to just climb outside a crap-ton.

Eventually, I started to gain a little recognition. For the most part, it’s just grown organically. I like it that way. I don’t want to force it or try to be someone I’m not. Maybe that’s my mentality from home—I’m always thinking, “You ain’t shit; you’re just another boy from the holler.” I mean, I’m just a rock climber. I even live in a van down by the river sometimes.

After you’ve lived so long under the radar, what’s been the biggest adjustment to going pro?

In the beginning, as I traveled more and more, I started to lose touch with friends. Back in Chattanooga, we were all together all the time because nobody ain’t got money to go nowhere, you know? So I was psyched to travel, but I’d look around and realize I wasn’t with my friends anymore. Life on the road is tough because you never really feel like you belong—you’re never integrated into a community.

Webb getting airy on his alpine highball Lost Eagle (V13; FA: 2018) deep in the Wind River Mountains of Wyoming.Kevin Takashi Smith

As an obsessive climber, how do you find balance?

As I get older, I’ve put a lot more effort into staying in touch with friends, spending more time at home, and just trying to relax instead of being so neurotic about climbing. That balance takes time to learn, and I’m still learning every day. [My obsession] affected my last relationship, and rightfully so. You have to find a person who accepts you for you and understands you enough to make that coexisting work. Fortunately, my current girlfriend, Hannah, and I have been awesome with that. She’s in school right now, so we’re both working hard at our own things.

I’m getting better at focusing on the people around me, because at the end of the day, I’m going to remember my friends and family more than I’m going to remember climbing a piece of rock. 

5 Things You Didn’t Know About James Webb III

  1. Drink of choice: Red wine
  2. Childhood pet: Gizmo the Chihuahua (he now has a Siberian husky named Oreo)
  3. Favorite pre-sesh pump-up music: J.I.D.
  4. Other talents: 9-ball pool, 8-ball pool, snooker, skateboarding
  5. Coolest skate trick accomplished: 360 kickflip

Webb’s Top 5 Tips for Highball Bouldering

Jimmy Webb calls mastering the psychological aspects of highball bouldering one of the most fascinating challenges of his climbing career. Here are his top tips for prep and execution: 

  1. Get on a rope. Spend time rehearsing the moves on a rope until you’re 100-percent confident in your ability to succeed. Usually, you have only one unroped try, so if that means a month of toproping, take that time.
  2. Make a fall strategy. Check that the pads are exactly where they need to be. Make sure the spotters know the plan, from moving the pads at the right time, to getting out of the way later—after a certain height, a fall could hurt the spotter just as badly as the climber.
  3. Visualize. You need to have your beta dialed. The night before, I spend a lot of time rehearsing the moves in my head, visualizing myself going from the bottom to the top successfully. (This kind of visualization is proven to improve confidence and reduce anxiety when you’re actually trying to execute.)
  4. Be patient. If you get to the base and don’t feel 100-percent prepared and psyched to climb, don’t. I’ve walked away from many lines because I either didn’t feel ready that day or I decided the risk wasn’t worth the reward.
  5. Pick a point of no return. Pick a point at which it would be unsafe to fall or impossible to downclimb. When you get there, it’s decision time: If you feel ready to try, you have to commit 100 percent. If you arrive with doubts, bail.