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Making People Laugh: The Life and Work of Brendan Leonard

A profile of trail runner, author, illustrator, and creator of the Semi-Rad brand, Brendan Leonard.

By on January 4, 2024 | Comments

If you’re an outdoorsy person who spends time online, chances are good that you’ve laughed at something created by writer, illustrator, filmmaker, and creator of the Semi-Rad brand, Brendan Leonard. You’ve even had the chance to here on iRunFar, where Leonard comically illustrated a series on trail first aid several years ago.

An illustration by Brendan Leonard of Semi-Rad for iRunFar’s trail first aid series.

Semi-Rad began as a blog circa 2011, when Leonard began publishing humorous illustrations poking fun at being an average outdoorsy go-getter. The digestible, comical nature of the line charts caught digital audiences like wildfire. They’re now regularly republished on “Outside,” alongside Leonard’s stories, amongst other publications.

“I drew a bunch of jokes within a flow chart of pooping in the woods. That very quickly became the biggest thing I’d done. It went totally viral, for me,” recalled Leonard.

He continued, “It’s funny how many people won’t finish an 800-word written piece, but if you draw it, they can digest it in 15 seconds,” said Leonard, who drew more pieces, published several per week via social media, and added the illustrations to collectibles like coffee mugs. His creative career gained momentum.

Riding the long game of his creative vision, Leonard started producing Semi-Rad when he had trouble reaching national publications. “I had all these story ideas that were never going to get published. I’d been pitching magazines and editors since 2004. ‘Mountain Gazette’ would occasionally run my stuff, but I thought, this’ll never work at ‘Backpacker’ or ‘Outside.’ I don’t have enough experience writing. They don’t think it’s funny. It was late 2010. I was like, ‘These people don’t want this stuff.’”

Brendan Leonard - GearJunkie podcast

Brendan Leonard appearing on the GearJunkie podcast in 2019. Photo: GearJunkie

Something clearly changed. “I remember the first time I was writing for an editor of a big magazine and they said, ‘Just write it like you write it for your blog.’ Then in 2017, after I’d done the blog for years, “Outside” said, ‘We like what you’re doing.’ It was a compliment, but also interesting seeing how media was changing,” said Leonard.

It was a time when individual creatives could utilize a variety of platforms to reach broad audiences that, perhaps, even legacy publications might not capture.

Leonard likely won’t be the first to speak of his success, but when he does, it would only be with the self-deprecating humor for which he is known. But the evolution of both his trail running and creative endeavors reflect that success is possible through committing to the process even if validation doesn’t arrive right away.

Now 45 years old, Leonard grew up in a handful of small towns surrounding New Hampton, population 3,000, in the northeast slice of Iowa. In the state’s furthest, flattest corner, the shared boundaries with Wisconsin and Minnesota are known as the Driftless Area, where the glaciers of the Ice Age 10,000 years ago never reached, unlike much of the rest of the U.S. Upper Midwest. This unique geology and preserved plants like the northern wild monkshood, and organisms like the Iowa Pleistocene snail, are sung about by conservationists.

While being a kid there, Leonard admittedly didn’t know much about that history. He did have a job picking rocks out of the farm soil, which was some 20 miles from the boundary of the Driftless Area and loaded with glacial till. Any rocks bigger than a fist had to be removed from cornfields, so they couldn’t break the combine harvester machine.

“The tallest thing on the horizon was a grain silo,” said Leonard, who’s brother is exactly 18 months older than him, lives in Wisconsin, and isn’t a runner. “He likes to fish. Good dude.”

Leonard played basketball until his junior year in high school, when he switched to football. He also ran track those four years, including being team captain as a senior. He ran the 4 x 100-meter and 4 x 200-meter relays, 200-meter dash, and he dabbled in the 400-meter distance.

“I was slow getting out of the blocks, got speed 10 to 15 meters into it, and then I was fast from 15 to 200 meters. In the relay, kids would count eight to 10 steps, and I’d count 22. I was like a cartoon character running in quicksand for the first two seconds,” said Leonard, who grew up in a goofy family, which he didn’t realize was unique until he was out of college.

Brendan Leonard - high school track newspaper cutting

A cutting from a local newspaper showing Brendan Leonard running track in high school. All photos courtesy of Brendan Leonard, unless otherwise noted.

Reading the book “Humor Seriously” when we did this interview, Leonard is now more aware of his family dynamic.

“My dad is funny. My mom grew up with six brothers and sisters, and they try to one-up each other with jokes. It didn’t occur to me people didn’t try to make each other laugh as a family — that it wasn’t common. After college, I’d go to friends’ or girlfriends’ houses and think the parents didn’t like me, because they weren’t laughing. They weren’t joking with me, which was strange for me, I guess. That was the easiest thing for me to do — default to humor and put levity into situations,” said Leonard. With serious topics, throwing in some humor can improve the outcome of the message being received, he’s found.

Leonard acknowledged that his knack for humor may have been detrimental in grade school.

“I could be a scientist now if I hadn’t been goofing off in class. It seemed like a cool thing to be,” he said. Nonetheless, Leonard graduated from the University of Northern Iowa with a marketing degree, and started reporting for the newspaper his senior year, which he was excited about.

The following year, in 2002, he pursued a master’s in journalism at the University of Montana. After two years, he graduated, published one article — a story in “Idaho Magazine” about climbing the tallest peak in Idaho, for $40, his entire freelance income for the year  — and moved to Colorado’s Front Range.

There, the then 26-year-old dabbled in trail running but generally “was not into it.” He was psyched on rock climbing and mountaineering for nearly a decade, until 2015.

But then a good friend signed up for a 50-kilometer race in the Denver, Colorado, suburbs. Leonard took him out to dinner after he’d finished a 22-mile training run.

“He talked about how badly it went. He’d run out of water and had to ask people for help. I thought that sounded awesome. I signed up for the 50k, for fun. I thought I could run half of the 50k and walk the second half,” he said, crossing the September finish line of the Bear Chase Trail Race 50k only 24 days later, at age 36.

Brendan Leonard - training in hills

Brendan Leonard training in the hills. Running is now a big part of his life.

“I’d run a marathon once and hated it. But I’d spent a lot of long days in the mountains doing 14-hour days hiking in with a backpack, climbing, descending, and hiking out. I knew a 50k would take less time than that, and that I could keep moving. I knew I could do that and not die. I came from a different angle than people who run roads and have a time in mind. I wanted to survive it and see what it was like,” recalled Leonard, who was also looking to replace his climbing with a similar activity that’s full of beautiful mountain scenery, pushing yourself mentally and physically, and pain and suffering — yet far less risk.

Next, he dove into a 50 miler, the Ice Age Trail 50 Mile, in May 2016. “I thought everyone at the start line would look like Ironman triathletes, but everyone was normal looking and very weird in the same way — we all thought that this would be fun or challenging or worth it in some way. Ultrarunners are my type of weirdo,” he said.

Ultimately, Leonard sees countless parallels between being a runner and being a creative.

“Running is such a great metaphor for creative work. If you work for yourself or you’re a runner, you have to be self-motivated. No one is making you get out the door to run when it’s freezing or raining or hot. You decided you wanted to run a race, and now you have to train for it,” he said. “I enjoy flexing that muscle over and over again and staying motivated enough to keep the work coming.”

Brendan Leonard - Wind River High Route

Leonard navigating the Wind River High Route.

Between 2013 and 2016, Leonard published his first three books. He’s now authored more than a dozen, including “Make It: 50 Myths and Truths About Creating,” which hit shelves in April 2023.

He kept up with trail running and ultrarunning, and dare we say developed this interest even more. Despite hating his first marathon, Leonard ran 26.2 miles 52 times in a single year. He traversed Colorado’s Sangre de Cristo Range and Wyoming’s Wind River Range by foot. He also finished the 2017 Run Rabbit Run 100 Mile, 2019 Hellbender 100 Mile, and 2019 Bighorn Trail Run 100 Mile.

In case you’re wondering how he got through those lengthiest races, one of his favorite authored books is, I Hate Running and You Can Too: How to Get Started, Keep Going, and Make Sense of an Irrational Passion.” He said, “It’s a short book about how to get into running, or how to keep running if you don’t like it, with 80 illustrations. It’s been translated into three or four languages, which is a big deal for me. That’s been one of the most fun ones.”

Also in Denver, Leonard met his now wife, Hilary Oliver, a writer and editor, while she was working at Watercourse Foods, a vegetarian restaurant, in 2012.

“She was really into mountain biking and I was into climbing. Neither of us do that anymore but we both still run. Out of the two of us, she enjoys running. I’m more of a, ‘I have to do it, like brushing my teeth,’ runner. For getting outside, I need things that’ll get me out the door, but I’m slowest to get out.” he said.

He was living in his 2005 Chevy Astro van at the time, which he lived in for 2.5 years. After six months of dating, Oliver moved into the van with him.

“I remember looking down on where our van was parked in Zion National Park, next to a sprinter van, and was like, ‘That’s huge. I bet they can stand up when they put their pants on.’ It was great for what it was. It was $6,500, and that was my entire life savings,” said Leonard.

Brendan Leonard - in van

Brendan Leonard relaxing in his van.

Altogether, Leonard lived in the Denver area, including a fixer-upper in the City Park neighborhood with Oliver, for 15 years until relocating to Missoula, Montana, where the couple could “buy a house more than 800 square feet” in 2020. That’s where they had Jay, now one year old.

Oliver still edits everything Leonard creates. “She edits 100% of everything I do. I will show her my stupid drawings, and she’ll say, ‘Yeah.’ She used to laugh. Now she just tells me if it’s funny or not,” he said.

The couple always talks about creative things — movies, films, books — and passes books back and forth from bedside table to table. “There are so many books I would not have read had I not been with her. I try to read 50% books by authors that identify as female. It’s difficult. I gravitate toward male writers, and to consciously choose female writers is a big deal. Since she [Oliver] naturally reads more women writers, I benefit from that, and she has great taste in literature,” said Leonard.

They’ve also shared many miles through crewing, pacing, and running events side by side. In November 2023, the duo ran the Rim-to-Rim-to-Rim in the Grand Canyon, a 48-mile route with 11,700 feet of ascent, as a first adventure after the birth of their baby. Leonard wrote about the experience in his weekly newsletter, “The Grand Canyon Twice, in 11 Photos,” penning:

“Hilary was amazingly still crushing with five miles to go. Suddenly, I bonked, and hurriedly ate some food. Then Hilary hit a wall, her body instantly realizing it had been going for 14 straight hours. All the warning lights came on: cramps, nausea, fatigue. She dry-heaved to the side of the trail, our headlamps the only visible lights. This was our first all-day, child-free date since Jay was born. It felt very on brand. As we passed the 1.5-mile rest house, I saw the emergency phone, and remembered, oh yeah, you could call for a rescue here. We were clocking 38-minute miles, but we weren’t going to die. We just kind of felt like we were going to die.”

With a baby, life balance looks more like a triage of daycare, viruses, and occasional smooth days.

Being a parent “is probably the hardest thing I’ve ever done. It’s relentless. You can always quit a 100-mile race. Even if you do finish it, it’s over. This is relentless, that’s the best word I’ve heard. But it’s micro doses of joy everyday. You can’t really complain. Plus, we did it to ourselves. It was our idea! I just focused on taking care of Hilary so she could take care of Jay, because I can’t breastfeed,” he said.

Brendan Leonard - 2021 New York City Marathon

Brendan Leonard running the 2021 New York City Marathon.

Despite shaking up the routine with a third member of the family, Leonard still gets outside to run and still creates funny content. In August 2023, he published the film, “The Seven Summits of My Neighborhood,” about biking and running to the highest summits within a 20-mile radius of his home, an alternative to the much pricier expeditions to summit the highest mountains in the world.

Over the years, Leonard gravitated toward film creation after attending film festivals and watching friends transition from podcasting into filmmaking, like Fitz Cahall, founder of the “Dirtbag Diaries,” followed by “Duct Tape Then Beer.” “It was cool to watch an audience take in what you made, as opposed to writing, where you occasionally get an email from someone who is not your mom,” said Leonard.

In September 2023, Leonard hosted a trail running and creative workshop, in partnership with Freeflow Institute and Alpine Running Guides, which was a new spin on a writing workshop he’s typically hosted, via a whitewater trip, since 2019. With a first-ever trail running focus, the spots have never sold out so fast.

“People are getting book contracts for writing captions or for TikTok videos that reach people. I enjoy that. I’m not very good at drawing, and a lot of people would say, ‘I’m not good at writing, and definitely not a good cinematographer’ — but can you do it well enough to get your point across? We’re in a media environment that’s forgiving for those things. You don’t watch TikTok for Oscar-winning cinematography,” he explained.

Leonard agreed, being a creator full time reflects a level of success. When I asked what his favorite part of being a creator is, Leonard said, “I think just the freedom to do creative work every day. To move things forward and make things. Being able to come back and do it every day is amazing. I think about people who do well with a brand or book promotion. I wonder what it’s like to have one really good book that you’re cranking out speaking engagements on — they’re probably making a ton of money, but talking about the same thing over and over again, that would also suck. I get to choose what I do on a daily basis, because of my lack of success, so it’s a gift, too, to not be successful.”

“Being able to sit down every day in my office and draw or write or create, that’s the real gift. If it allows me to make a living, awesome. That’s the level of success I’m happy with.”

Call for Comments

  • Are you familiar with Brendan Leonard and Semi-Rad’s creative work?
  • What are some of your favorite works by him?
Morgan Tilton

Morgan Tilton is the WeRunFar columnist of iRunFar and a Staff Writer for GearJunkie and AllGear Digital. Morgan has covered outdoor industry news, adventure travel, and human endurance for nearly a decade. Aside from iRunFar, Morgan has written for more than 70 publications, including recent contributions to Outside, Forbes, Trail Runner, Runner’s World, Bicycling, and NewsBreak. She’s a recipient of more than a dozen accolades for her travel writing from the North American Travel Journalists Association. Based in Crested Butte, Colorado, Morgan enjoys mountain running and exploring the high alpine in the summer when she’s not splitboarding or mountain biking.