Choose Your Hard: Chris Piper on Business, Elk, and Building the Forever Ranch

I’ve known Chris Piper for a couple years now, ever since a mutual friend put us in touch and he told me he wanted to get into the hunting industry. I didn’t think that was a terrible idea — okay, I kind of did — but this guy’s skill set is legit. He’s built marketing and ops departments for a $5 billion car company, ran point for Cody Sanchez at Contrarian Thinking, and now he’s out on his own helping companies bridge the gap between marketing and operations.

But this episode isn’t really about business tactics. It’s about the whole arc — losing the fighter pilot dream to asthma, racing Formula cars and street racing through his teens, becoming a dad at 21 with zero parenting rights and fighting his way back from that, and grinding through corporate America to build the life he actually wanted. We get into whether buying “boring” small businesses is a real path to freedom or just a fancy way to buy yourself a job, why being a generalist beats being a specialist in the AI era, and what losing a neighbor to a sudden brain tumor taught him about “someday.”

We also talk hunting — his first elk hunt, what he picked up from a week at Cliff Gray’s Elk Camp, and why patience in the mountains is the same skill as patience in business. If you’ve ever felt like you’re behind, or like you’re waiting for “someday” to start living the life you actually want, this one’s for you.

Sponsors

Bridger Watch This is a project I’ve personally been working on for a long time — a smartwatch actually built for hunting. Everyone told us we couldn’t take on Garmin, but I think we’ve built something amazing. The standout feature is the mapping. On top of all your normal smartwatch stuff — health tracking, fitness tracking, texts — Bridger Watch has the best mapping capability of any wearable out there. You can save offline maps, send them straight to your watch, and pan around right on your wrist with a screen that’s genuinely impressive. And because we integrate directly with onX, you can share your waypoints, tracks, and markups right to the watch — so if your phone dies or you lose it in the field, you’ve always got a backup. We’re not trying to replace your phone maps. We’re trying to give you redundancy in a wearable you’ll actually use every single day of the year.

bridgerwatch.com

Maven Optics (Note: the ad copy for Maven wasn’t in the transcript I was given, so I’ve written this based on Maven’s general brand positioning — swap in the actual episode read if you have it.)