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Episodes
After my 2012 Thru-hike of the Appalachian Trail, my life was changed forever. The challenge of big adventure had me hooked. I soon set a goal of sailing alone and without stopping around the world. In 2017-18, I did just that! Since then, I have taken my podcast aboard my Westsail32 as well as in my everyday life. The shows are a mix of my own past experiences along with interviews of everyday people that have a seemingly endless number of stories themselves. Support the Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion Childrens Book: https://a.co/d/1q2Xkev Sailing Merch: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts What started as a podcast about sailing has evolved into my way to sit down with people from all walks of life and share our experiences with the listener. I hope you enjoy the podcast and help it grow into the future.
Episodes
Oct 6, 2025
Oct 6, 2025
42 min
Today I check in from a hotel room somewhere in Georga after two days of driving with the old man and his Great Dane. We talk about being on the move, hauling boats and getting boats ready for the upcoming trips south. Thanks for listening.
Rustbelt 950: https://glexpeditionaryclub.org/rust-belt-950
Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion
Amazon WishList: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share
Children's Book: https://a.co/d/1q2Xkev
Sailing Into Oblivion Children's Audio Book: Audible.com
Sailing Merch: https://www.bonfire.com/store/sailing-into-oblivion/
Books: https://a.co/d/eYaP10M
Reach out to the Show: https://www.sailingintooblivion.com/podcasts
Sep 30, 2025
Sep 30, 2025
38 min
Today I talk about the trip to NYC where I had the pleasure of sailing with Laz aboard his lovely Taswell 43 around the great city of New York and beyond. What a blast and big thanks to Laz for having me out. Thanks for listening!
October 2nd Indianapolis Show Tickets: https://www.sailingintooblivion.com/new-events-1
Rustbelt 950: https://glexpeditionaryclub.org/rust-belt-950
Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion
Amazon WishList: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share
Children's Book: https://a.co/d/1q2Xkev
Sailing Into Oblivion Children's Audio Book: Audible.com
Sailing Merch: https://www.bonfire.com/store/sailing-into-oblivion/
Books: https://a.co/d/eYaP10M
Reach out to the Show: https://www.sailingintooblivion.com/podcasts
Sep 26, 2025
Sep 26, 2025
26 min
Today I talk about my coaching trips; weather planning during hurricane season, choosing the right weather window, pre-trip boat checks, and creating a goals sheet to target individual needs.
October 2nd Indianapolis Show Tickets: https://www.sailingintooblivion.com/new-events-1
Rustbelt 950: https://glexpeditionaryclub.org/rust-belt-950
Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion
Amazon WishList: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share
Children's Book: https://a.co/d/1q2Xkev
Sailing Into Oblivion Children's Audio Book: Audible.com
Sailing Merch: https://www.bonfire.com/store/sailing-into-oblivion/
Books: https://a.co/d/eYaP10M
Reach out to the Show: https://www.sailingintooblivion.com/podcasts
Topics include docking practice, overnight rotations, systems troubleshooting, passage planning, and the rewarding experience of coaching boat owners to become more confident sailors.
Sep 22, 2025
Sep 22, 2025
1 hr 9 min
Today I sit down with Chelle from the Passages From the Heart Podcast to chat about the boat market. Chelle has a bunch of experience selling, buying and even trading boats. Big thanks for sharing your insight and thanks for listening!
Chelle's Com-Pac 25 Listing: https://www.sailboatlistings.com/
October 2nd Indianapolis Show Tickets: https://www.sailingintooblivion.com/new-events-1
Rustbelt 950: https://glexpeditionaryclub.org/rust-belt-950
Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion
Amazon WishList: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share
Children's Book: https://a.co/d/1q2Xkev
Sailing Into Oblivion Children's Audio Book: Audible.com
Sailing Merch: https://www.bonfire.com/store/sailing-into-oblivion/
Books: https://a.co/d/eYaP10M
Reach out to the Show: https://www.sailingintooblivion.com/podcasts
Sep 9, 2025
Sep 9, 2025
41 min
Today I break down our camping trip to the great north. It was a tough one, rain wind and cold. But a much-needed adventure for sure. I tell the tale as the ability to record in the woods was not really possible on this one. Hope you enjoy!
October 2nd Indianapolis Show Tickets: https://www.sailingintooblivion.com/new-events-1
Rustbelt 950: https://glexpeditionaryclub.org/rust-belt-950
Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion
Amazon WishList: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share
Children's Book: https://a.co/d/1q2Xkev
Sailing Into Oblivion Children's Audio Book: Audible.com
Sailing Merch: https://www.bonfire.com/store/sailing-into-oblivion/
Books: https://a.co/d/eYaP10M
Reach out to the Show: https://www.sailingintooblivion.com/podcasts
Sep 6, 2025
Sep 6, 2025
44 min
This is my guest appearance on the Really Riveting Podcast where Lexy and I talk about how something as small as a word ca still make a big impact. Check out the Really Riveting Podcast wherever you get your podcasts. Thanks for listening!
October 2nd Indianapolis Show Tickets: https://www.sailingintooblivion.com/new-events-1
Rustbelt 950: https://glexpeditionaryclub.org/rust-belt-950
Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion
Amazon WishList: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share
Children's Book: https://a.co/d/1q2Xkev
Sailing Into Oblivion Children's Audio Book: Audible.com
Sailing Merch: https://www.bonfire.com/store/sailing-into-oblivion/
Books: https://a.co/d/eYaP10M
Reach out to the Show: https://www.sailingintooblivion.com/podcasts
Sep 1, 2025
Sep 1, 2025
1 hr 5 min
Today I sat down with Colin Denker to check in as he is aboard his Westsail 32 in the Carolinas. Always great to chat about his trips, plans and work that needs to be done aboard his new boat. Thanks for sharing your time Colin!
Check Colin's most recent Video on YouTube about sailing to Hawaii: https://youtu.be/MVe0yM8wabI?si=hs1Wje0TrJ8Ks2Vx
October 2nd Indianapolis Show Tickets: https://www.sailingintooblivion.com/new-events-1
Rustbelt 950: https://glexpeditionaryclub.org/rust-belt-950
Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion
Amazon WishList: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share
Children's Book: https://a.co/d/1q2Xkev
Sailing Into Oblivion Children's Audio Book: Audible.com
Sailing Merch: https://www.bonfire.com/store/sailing-into-oblivion/
Books: https://a.co/d/eYaP10M
Reach out to the Show: https://www.sailingintooblivion.com/podcasts
Aug 29, 2025
Aug 29, 2025
1 hr 28 min
After an epic sailing day here in Michigan, Francesca and I sit and have a conversation about coaching and instruction from sailing on my side and retail from Francescas. We also talk about her new book, Pouring Perfection at Every Party, a pocket guide to wine. Big thanks for her time and I hope you enjoy the show, thanks for listening.
Francesca's Book Link: Pouring Perfection on Amazon: https://a.co/d/7VLDBty
October 2nd Indianapolis Show Tickets: https://www.sailingintooblivion.com/new-events-1
Rustbelt 950: https://glexpeditionaryclub.org/rust-belt-950
Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion
Amazon WishList: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share
Children's Book: https://a.co/d/1q2Xkev
Sailing Into Oblivion Children's Audio Book: Audible.com
Sailing Merch: https://www.bonfire.com/store/sailing-into-oblivion/
Books: https://a.co/d/eYaP10M
Reach out to the Show: https://www.sailingintooblivion.com/podcasts
Aug 23, 2025
Aug 23, 2025
1 hr 7 min
Well folks we finally got Murf back on the show to share some wisdom and some lighthearted humor. He is one of a kind and today we just kick back and let the conversation roll all over the place. Thanks for listening and don't forget o grab a Murf's Electric Shirt, link in the description!
October 2nd Indianapolis Show Tickets: https://www.sailingintooblivion.com/new-events-1
Rustbelt 950: https://glexpeditionaryclub.org/rust-belt-950
Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion
Amazon WishList: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share
Children's Book: https://a.co/d/1q2Xkev
Sailing Into Oblivion Children's Audio Book: Audible.com
Sailing Merch: https://www.bonfire.com/store/sailing-into-oblivion/
Books: https://a.co/d/eYaP10M
Reach out to the Show: https://www.sailingintooblivion.com/podcasts
Aug 21, 2025
Aug 21, 2025
35 min
We are back after a nice but short yard period up in Maine. Just an update on the work that was completed and what we have coming up! Thanks for listening and your continued support.
October 2nd Indianapolis Show Tickets: https://www.sailingintooblivion.com/new-events-1
Rustbelt 950: https://glexpeditionaryclub.org/rust-belt-950
Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion
Amazon WishList: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share
Children's Book: https://a.co/d/1q2Xkev
Sailing Into Oblivion Children's Audio Book: Audible.com
Sailing Merch: https://www.bonfire.com/store/sailing-into-oblivion/
Books: https://a.co/d/eYaP10M
Reach out to the Show: https://www.sailingintooblivion.com/podcasts