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.) Maven builds premium hunting optics — riflescopes, binoculars, and spotting scopes — and sells direct to the hunter instead of marking everything up through a retail middleman. That means you’re getting glass that goes toe-to-toe with the big legacy brands, at a price that actually makes sense, backed by their unconditional lifetime warranty.

mavenbuilt.com Use code TRO at checkout for a discount.

Chapters

• 00:00 – Cold open: onX Hunt’s new Go Track “share your location” feature
• 01:00 – Sponsor: Bridger Watch
• 03:00 – Welcome Chris Piper, how they met and reconnected
• 05:15 – Chris’s original dream: Air Force pilot, shut down by asthma
• 08:30 – The street racing years — the helicopter chase story
• 12:30 – Becoming a dad at 21 and the custody fight that followed
• 17:00 – Choosing responsibility, insurance sales, and the climb into corporate America
• 21:00 – Director of Market Strategy at DriveTime and the biggest lesson from his 20s
• 25:30 – Chasing money vs. mastering a skill — building a “Swiss Army knife” career
• 30:00 – Generalist vs. specialist in the age of AI — why curiosity is the real edge
• 35:30 – Leaving corporate for Tucker Max, moving the family, and near-jail custody stress
• 41:00 – Joining Cody Sanchez at Contrarian Thinking, buying “boring” businesses
• 47:00 – Is buying small businesses real, or are you just buying yourself a job?
• 53:00 – The most successful (and surprising) small businesses to own
• 57:30 – Specialists vs. operators — why the best welder shouldn’t run the company
• 1:00:30 – What Chris wants his 40s, 50s, and 60s to look like — the forever ranch and an elk tag in every western state
• 1:04:00 – Losing a neighbor to a sudden brain tumor and why “someday” isn’t guaranteed
• 1:07:00 – Where the audacity to go get what you want actually comes from
• 1:08:30 – Wrap-up: Cliff Gray’s Elk Camp, patience in hunting vs. business, and where to find Chris

Three Key Takeaways

1. Disappointment comes from unmet expectations, not from reality itself. Chris talks about resetting his expectations daily instead of holding himself (or his team, or his family) to a fixed standard 24/7. Some weeks call for going all-in on the business; other weeks, the win is just showing up as a present dad. Adjusting the bar to the moment isn’t lowering it — it’s being honest about what’s actually needed right now.
2. In the AI era, being a curious generalist beats being a narrow specialist. Chris didn’t get ahead by mastering one skill — he stacked social media, SEO, PPC, PR, and operations, then learned to move fluidly between marketing and ops. The real leverage now isn’t knowing one thing deeply; it’s having enough taste and curiosity to judge what AI (or anyone else) hands you and say, “that works” or “that’s BS.”
3. Buying a small business can absolutely change your life — but it’s still a job, just a different kind of hard. Chris saw thousands of people go through the acquisition process at Contrarian Thinking. Some genuinely built freedom and equity; others just bought themselves a demanding new job with their name on the door. The difference wasn’t the business model — it was whether the buyer had real operating leverage (sales, marketing, or ops chops) going in.