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On the Wind Sailing

'On the Wind,’ is THE podcast about offshore sailing, where professional sailor & journalist Andy Schell interviews sailors from around the world to discover what inspires them in an effort to inspire you! Andy has interviewed everyone from legends like Sir Robin Knox-Johnston, to tech gurus like Nigel Calder, boat builders like Magnus Rassy (of Hallberg Rassy), inspirational family sailors like Totem, YouTube stars SV Delos & Andy's personal favorite, Arctic sailor and octogenarian Bob Shepton. Thanks for listening & hold fast!

Jan 5, 2016

#134. Happy New Year! Welcome to the first episode of 59º North in 2016! 

Episode 134 is Jesse & Samantha Osborn. You won’t have heard of them, but they’re some of the most interesting and accomplished cruising sailors I’ve ever come across. Matt Rutherford introduced me to them last fall and they ended up sleeping aboard Isbjorn during the week of the Annapolis Boat Show, bunk-mates with the legendary Don Street, who also took up residency aboard. Jesse & Samantha sail a one-off, steel-hulled gaffer called Empiricus and recently completed the Northwest Passage, and only just, narrowing avoiding getting frozen in for a long winter. Empiricus remains hauled out in Iceland, where they’ll be continuing their adventures in the Arctic next summer. Amazingly, the couple had little prior sailing experience before their adventure in the Arctic.

In the offseason, Jesse & Samantha live a sort of home-steading lifestyle in Alaska. Samantha is a veteran bush pilot, flying into and out of remote regions in Arctic Canada on float planes and ice planes, providing supplies to wilderness communities. Jesse is a former police officer and has since given that up in pursuit of his dream to live simply on the water and off. They started and run Seven Seas Sailing Logistics, a self-declared ‘sailing concierge, with the goal of helping others achieve their bluewater dreams.

Samantha & Jesse are also young, and I always get extra excited speaking to sailors in the up and coming generation, and these guys are super inspiring. A favorite quote I discovered on their boat’s website, states “IF YOU DON’T WANT SOMETHING, YOU MAY SETTLE FOR ANYTHING. BUT ANYTHING, COULD BE NOTHING AT ALL.” It pretty well sums up their dreams and ambitions. Check out the podcast page on for some bonus content that goes alongside this episode, including links to Jesse & Samantha’s adventures.

This episode was recorded during a break I had at Cruiser’s University in Annapolis last October, and about a third of the way in, Pam Wall pops into the conversation as a surprise special guest! Pam had asked to listen in on the conversation as we recorded. I think she meant to remain off-mic, but Jesse & Samantha’s stories were so compelling that she couldn’t resist asking them some questions of her own. It was truly inspiring watching Pam, a legend of her generation of cruisers, interact with us up-and-coming younger sailors and seeing her eyes light up at Jesse & Samantha’s stories. It was a real honor having Pam sort of co-host this episode.


Thanks to everyone who answered the call to donate after the bonus ‘Money’ episode, in particular longtime listener Pedro for his generous gift. If you'd like to help support the show and Isbjorn Sailing, visit to buy some small-batch gourmet Oh Dark Thirty coffee, an Isbjorn Sailing t-shirt or simply donate to the podcast. Of course a nice email is always welcome, as are reviews on iTunes. Thanks to all of you for the continued support. Both Mia and I wish you all a happy and healthy 2016!