Brendan Leonard is back for his third appearance on the podcast—this time recorded in person at his house in Missoula. Brendan’s the creative mind behind Semi-Rad, and over the years, he’s become a good friend and one of my most trusted advisors when it comes to creativity and building a life around the things you care about. He’s a writer, illustrator, filmmaker, ultrarunner, teacher, and all-around creative machine—someone who’s carved out a career by doing things his own way, with a healthy dose of humor and generosity.
This episode is pretty much two friends sitting at a kitchen table having a laid-back chat about our long list of shared interests. We talk about everything from teaching writing and designing online courses, to the pros and cons of Substack, to how to market your work without feeling like a sellout. We dig into the practical side of creativity—how to make things, share them, and make a living—without losing the joy and weirdness that made you want to create in the first place.
We also get into self-publishing vs. traditional publishing, why Brendan makes funny books like 15-Second Recipes, and why he believes that generosity, self-deprecation, and consistency matter more than flash or perfection. There’s a lot here for anyone trying to make meaningful things in the margins of a busy life… or build a creative life from the ground up.
If you’re new to Brendan’s work, be sure to check out his website, newsletter, and his earlier podcast episodes. I’d also specifically encourage you to check out his most recent book Ultra-Something, his recent film The Seven Summits of My Neighborhood, and the podcast he co-hosts, which is called The Trailhead.
Brendan is one of the most thoughtful, practical, and humble voices out there when it comes to creative work, and I’m always better off after talking to him. Hope you enjoy.
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All photos courtesy of Brendan Leonard
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RESOURCES:
Topics Discussed:
- 2:11 – Brendan blowing out the speakers
- 3:47 – How Brendan got into teaching and early days at Freeflow
- 8:06 – Brendan’s teachers
- 11:09 – The Feynman technique
- 14:10 – Substack versus a website
- 17:54 – The necessity of marketing yourself
- 20:53 – Keeping the voice
- 25:00 – Moving Brendan’s writing course online
- 27:23 – Keeping it low-key
- 29:40 – Abundance vs. scarcity mentality
- 33:56 – Publisher vs. self-publishing
- 38:39 – Nickels and dimes of self-publishing
- 42:31 – Talking Seven Summits of My Neighborhood
- 50:23 – Digging into the niches
- 51:55 – Curing the male loneliness epidemic
- 55:44 – Helping people with humor
- 58:43 – Treating others with respect
- 1:00:07 – Book recs
Information Referenced:
- Brendan Leonard
- Freeflow Institute
- University of Montana J-School
- Dirtbag Diaries podcast
- The Feynman technique
- Ryan Holiday’s Perennial Seller
- What To Do When It’s Your Turn
- 15 Second Recipes by Brendan
- The New American Road Trip Mixtape by Brendan
- Sixty Meters to Anywhere by Brendan
- Ultra-Something by Brendan
- The Seven Summits of My Neighborhood, a classic.
- Local: A Search for Nearby Nature and Wilderness
- Book recs: The Dad Rock That Made Me A Woman, Penguin Classics box set of really short stories (or at least one of them.)
Enjoy this episode? Then you might like these too:
- Nick Offerman – Empathy, Nuance, & Good Hard Work
- Mike DeHoff – Exploring the Colorado River’s Reemerging Rapids
- Dr. Alan Townsend – Generosity & Curiosity in the Face of Tragedy
- Joe Schobert – From NFL Pro Bowler to Western Conservation Advocate
- Scott Hulet: Reading + Writing + Surfing + Fishing + Traveling
- George Hodgin Returns – On Risk-Taking, Leadership, and the Future of Cannabis
- Elliot Ross: Where Landscape, Justice, and Storytelling Meet
Visit the podcast page for a full, searchable list of episodes
