November 19, 2025

From Cubicle to Mountains: Creating a Lifestyle Business That Funds Your Passion

1 hour 2 minutes

EP 673: Adam Callinan From Cubicle to Mountains

What’s up everyone! This week I sat down with Adam Callinan, entrepreneur and founder of Bottle Keeper (which sold over $60 million worth of product), and now the creator of Pentane, a tech platform for e-commerce brands. Adam and I dive deep into what it really takes to build a business that gives you the freedom to live the life you want, whether that’s hunting 100 days a year or just having more time with your kids.

We get into the nitty-gritty of entrepreneurship: the hospital-worthy panic attacks on launch day, the strategic patience required to make it through those critical first inflection points, and why most people completely screw up their pricing strategy. Adam breaks down how he and his cousin turned a hacksawed water bottle prototype into a multi-million dollar company with ZERO employees for years, and how you can actually test product ideas today without spending a fortune.

But this isn’t just a business podcast, we also talk about the parallels between building companies and hunting in the backcountry, the importance of doing hard things, and why getting comfortable being uncomfortable might be the most valuable skill you can develop. If you’re trying to build something that funds your passion for the outdoors, this episode is packed with real, actionable wisdom.

OnX Hunt – The ultimate hunting app just keeps getting better. Their new weather feature is a game-changer—tap anywhere on the map and get hyperlocal weather data that actually takes topography into account. No more guessing based on the nearest town. See wind variations across different parts of your hunting area and plan accordingly. Become an Elite member and get all the premium features. Head to onxmaps.com and use code TRO to save 20%.

Maven Optics – Direct-to-consumer optics out of Wyoming that punch way above their price point. From binos to rangefinders to rifle scopes, Maven delivers exceptional quality without the big box store markup. When people finally try them, the response is always the same: “Oh man, these are actually really good.” Check them out at mavenbuilt.com and use code TRO for a special gift at checkout.

Timestamps

00:00 – Intro

03:15 – Moving to Montana and the COVID exodus

08:20 – Getting into entrepreneurship and the path away from medicine

14:45 – The birth of Bottle Keeper and testing product ideas

22:30 – Crowdfunding, the Gizmodo article, and the name change

26:10 – Landing in the emergency room on launch day

30:45 – Building durability and getting comfortable being uncomfortable

35:20 – Perspective, hard things, and learning from people like Cal Arnold

41:00 – The importance of mentorship (and anti-mentorship)

46:30 – When to trust your gut vs. seeking outside advice

51:15 – Product development and pricing strategy mistakes

57:40 – The Facebook video inflection point and scaling to $30M

1:02:20 – Building a lifestyle business vs. unicorn hunting

1:05:50 – Strategic patience in hunting and business

1:08:00 – Closing thoughts

Three Key Takeaways

Test Before You Invest – Don’t quit your day job and go all-in on an unproven idea. Use tools like crowdfunding, 3D printing, and AI mockups to validate that strangers (not just family) will actually pay real money for your product at a profitable price point before spending significant time or capital.

Price Testing Changes Everything – Most entrepreneurs underprice their products based on what feels “fair” rather than what customers will actually pay. Adam tested Bottle Keeper from $20 to $40 over two years—that extra $20 margin was pure profit and enabled the company to scale even as advertising costs increased.

Durability Beats Talent – Businesses fail because people quit, not because the business itself fails. Building mental and emotional durability through perspective, doing hard things, and learning to be less reactive is more valuable than having the perfect idea or strategy. Those who can weather the storms long enough to reach their first major inflection point are the ones who succeed.

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