Matt Oesterle built his first company, Callisto Media, from zero to $85 million in revenue by using data to disrupt the book publishing industry. Then he sold it to Penguin Random House and asked himself: what's the next industry that hasn't been forced to evolve? The answer was camping — an industry whose biggest brands were founded in the 1960s and haven't changed much since.

In this conversation, Matt walks through the framework he uses to pick businesses, how he designed the Ramble campground experience from scratch, and what it takes to build a hospitality brand that maintains a 4.98-star review score while scaling to 100+ locations. He also gets into the role of data versus instinct in entrepreneurship, why type two fun is a hiring requirement for his team, and why you don't have to be a sociopath to build something great.

If you've ever looked at an industry and thought "someone should fix this" — this is the episode for you.

Show Notes:

Popfly for Brands: https://popf.ly/secondnaturebrands

Popfly for Athletes: https://popf.ly/secondnaturecreators

Matt Oesterle: https://www.linkedin.com/in/oesterle/

Ramble Campgrounds: https://ramble.camp/

Next Ventures: https://www.nextventures.com/

Mel Strong on Second Nature: https://www.youtube.com/watch?v=KlcjUzrM3Jg

Callisto Media: https://www.sourcebooks.com/callisto

HipCamp: https://www.hipcamp.com/

Net Promoter Score (Term): https://www.qualtrics.com/articles/customer-experience/net-promoter-score/

Solo Stove: https://www.solostove.com/

Zendesk: https://www.zendesk.com/

The Everything Store (Book): https://amzn.to/4vpM8kx

BPC - Brand, Product, Content:

RAB: https://rab.equipment/

The Algorithm (Book): https://amzn.to/4aOzKTJ

MFM Pod - The Algorithm Author: https://www.youtube.com/watch?v=GG4TwQEYdBY

New Yorker Profile - Sam Altman: https://www.newyorker.com/magazine/2026/04/13/sam-altman-may-control-our-future-can-he-be-trusted

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