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.”
Overland Journal Podcast Episode #287
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Guest Bio:
Jen Young
As co-founder and chief marketing officer of Outdoorsy since 2015, Jen Young has transformed outdoor travel by building the world’s most trusted marketplace for life on the road. Driven by a mission to connect people with nature, Jen scaled the “Outdoorsy Group” globally to include Wheelbase fleet management software and Roamly insurtech. To foster a community-first experience, Jen lived in an Airstream for a year, conducting thousands of interviews. This “boots on the ground” approach enabled her to correctly predict the “slow travel” and “near-cation” trends, guiding Outdoorsy through a 400% booking surge in 2020. Jen is also expanding the brand into physical hospitality with the Outdoorsy Destination Network, including properties like Outdoorsy Hill Country and Outdoorsy Yosemite.
Overland Vehicle Rental Guide: Campervans, Trucks, and Motorcycles
Host Bios:
Scott Brady
Scott is the executive publisher and co-founder of Expedition Portal and Overland Journal and is often credited with popularizing overlanding in North America. His travels by 4WD and adventure motorcycle span all seven continents and include three circumnavigations of the globe. His polar expeditions include two vehicle crossings of Antarctica and the first long-axis crossing of Greenland. @scott.a.brady
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