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Joe Rogan Experience #1955 - Cliff Gray

Cliff Gray is a former financial trader turned wilderness outfitter, hunting guide and YouTuber. https://pursuitwithcliff.com/

Cliff GrayguestJoe Roganhost
Jun 26, 20242h 38mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Ex–Wall Street Trader Becomes Wilderness Outfitter, Debates Wolves And Hunting

  1. Joe Rogan and hunting guide/outfitter Cliff Gray trace Cliff’s journey from a finance career to running a horse-and-mule wilderness hunting operation in Colorado. They dig into the realities of deep backcountry elk, sheep, goat, and lion hunting, including logistics, horses, Amish guides, and the physical and mental demands on hunters. A large portion of the conversation tackles predator management—especially wolf reintroduction in Colorado, mountain lions, and bears—and how ballot-box wildlife policy clashes with on‑the‑ground reality. They close by discussing hunting’s steep learning curve, the value of wild game meat, and why difficult outdoor pursuits can transform people’s lives.

IDEAS WORTH REMEMBERING

5 ideas

You can radically change careers if you accept uncertainty and lean on support.

Cliff left a stable, well-paid finance job to buy a failing outfitting business, relying on his upbringing, his wife’s backing, and his parents’ encouragement; he emphasizes that you can’t re-do life, so commit to the path you’re on instead of wishing for a different past.

True backcountry hunting is logistically intense and physically grueling.

Guided elk and sheep hunts in Colorado’s roadless wilderness require packing in wall tents, feed, and gear with horses and mules, caring for 10–15 animals in remote camps, and sometimes hiking or riding many miles just to reach heavily pressured elk or goats.

Skill-based, hands‑on education can be as valuable as formal schooling.

Cliff describes 18‑year‑old Amish workers who can saddle mules, build doors, and manage livestock from years of real work, illustrating how practical competencies and work ethic can rival or exceed conventional credential-focused education in many contexts.

Ballot‑driven wildlife policy often ignores ecological and economic realities.

Colorado’s wolf reintroduction passed via urban voters who won’t live with wolves’ consequences, while rural residents and outfitters will absorb livestock loss, dog predation, and ungulate declines; Cliff notes that each wolf effectively “eats” tens of thousands of dollars in potential elk-tag revenue annually.

Predators are fascinating but create real conflicts when unmanaged.

They describe wolves’ pack tactics and surplus killing, mountain lions’ specialized diets learned from their mothers, and bears’ variable behavior (from rolling in fox scat to attacking tents), arguing that love for predators must be tempered with a plan for population control and human–wildlife coexistence.

WORDS WORTH SAVING

5 quotes

If you're happy, you chose the right thing. But no one—there's no right thing. There's just life. Life and decisions.

Joe Rogan

I was looking at financial models one day, and three weeks later I was packing elk out of the wilderness on mules.

Cliff Gray

Everybody that voted for wolves doesn’t have to deal with the downside. The people who did vote no are the ones who are going to live with them.

Cliff Gray

Wolves are amazing, but they’re dominant, intelligent, calculating predators. They eradicated them from the West for a reason.

Joe Rogan

Hunting can change somebody’s life. A hobby can turn into something that makes you train harder, eat better, and completely reset how you see the world.

Joe Rogan

Cliff Gray’s background: rural upbringing, finance career, and shift into outfittingLogistics and lifestyle of wilderness guiding with horses, mules, and wall-tent campsAmish workers, work ethic, and alternative education vs. mainstream schoolingPredator behavior and management: wolves, mountain lions, and bearsColorado wolf reintroduction politics and ecological/economic implicationsHunting ethics, public misconceptions, and the role of hunters in conservationBarriers to entry in hunting and archery, and how hunting reshapes lifestyle and fitness

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