Backpacker Radio #236 | Kyle Hates Hiking on His Rise to YouTube Fame, Solving Trail Mysteries, and Getting EXPOSED

In today’s episode of Backpacker Radio presented by The Trek, we are joined by the very highly requested Kyle O’Grady, known in the world of YouTube as Kyle Hates Hiking. Kyle is an experienced backpacker, having hiked the Long Trail, Appalachian Trail, Northville Placid Trail, Pacific Crest Trail, and Ouachita Trail, amongst many others. In addition to learning about his many trail tales, we dive deep into his passion for video creation especially on the subjects of true crime and trail mysteries. From humble beginnings as a Writer for to having more than 300,000 subscribers on YouTube, this is an entertaining detailing of Kyle’s rise in the world of backpacking media.

We wrap the show with some details about the impending sale of Backpacker Radio’s famous hair wall, what we would do with an elephant, and the triple crown of social media hiking stereotypes.

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Interview with Kyle O’Grady

Time stamps & Questions

00:05:14 – Reminders: Support our editor, Pauly, and his coffee roastery, subscribe to the Trek’s newsletter, and apply to be a Trek blogger!

00:08:50 – Introducing Kyle

00:11:10 – Discussion about Kyle writing for Appalachian Trials

00:14:20 – Do people know you more from podcasting or Youtube?

00:15:15 – Give us a rundown on your Youtube

00:18:00 – What’s the process of writing and recording a trail mystery?

00:22:35 – How did you decide to pursue trail mystery stories?

00:26:00 – Give us the overview of the Scott Lilly story

00:27:51 – Give us the overview of the Bismarck story

00:32:00 – Discussion about the perception of the trail as dangerous

00:35:35 – Fuck Marry Kill: True crime, gear breakdowns, general thru-hiking advice

00:37:57 – Discussion about clickbait

00:40:02 – How do you decide how to portray your videos?

00:41:30 – Are you a gear nerd?

00:44:11 – Where do you get your footage?

00:45:45 – What sort of marketing education do you have?

00:49:48 – How do you maintain motivation despite negative comments?

00:52:37 – How did you transition to full time?

00:56:40 – Do you get anxious when a video doesn’t do as well as you expected?

00:59:08 – How much of a video’s success is due to the content versus the algorithm?

01:03:40 – Tell us about your podcast titles

01:06:45 – Discussion about asking AI questions about thru-hiking

01:08:50 – What’s the origin of the name Kyle Hates Hiking?

01:15:40 – What’s the latest thru-hiking social media gossip?

01:19:52 – Are you doing a lot of hiking in Hawaii?

01:23:57 – What’s your hot take about tramilies?

01:26:04 – Why should someone hike the Northville Placid Trail?

01:30:00 – Discussion about the Lone Star Trail

01:33:38 – Tell us about your podcast

01:36:07 – What are the primary differences between making a good video versus a good podcast?

01:41:26 – Story about Zach and Kyle’s near miss interaction

01:50:55 – Story about a bad fan interaction

01:55:25 – What’s the hiker scene like in Burlington?

01:58:00 – Is there an underrated Long Trail mystery?

02:06:20 – Discussion about Kyle writing for the Trek

02:08:30 – What’s next for you?


Trek Propaganda: The Best Thru-Hiking Tents of 2024 by the Editors

QOTD: You’ve been given an elephant. You can’t give it away or sell it. What would you do with the elephant?

Triple Crown of social media hiking stereotypes

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