Jen Young on Outdoorsy and the Entrepreneur’s Journey

Overland Journal Podcast host Scott Brady interviews Outdoorsy co-founder, Jennifer Young, about how her burnout from advertising led her to launch the peer-to-peer vehicle rental marketplace (an "Airbnb of overlanding") in 2014, growing to 200+ employees. Outdoorsy has expanded into the Outdoorsy Destination Network (campgrounds) and the Roamly insurance business. The platform highlights overlanding's growth (10%+ of listings), with common rentals including Tacomas, Jeep Gladiators, trailers, and EarthRoamers, typically priced around $160/night. They discuss the "try-before-you-buy" value and host motivations. Young also shares entrepreneurship advice like “start before you’re ready.” Jeff Cavins And Jen YoungSee omnystudio.com/listener for privacy information.