Sailing Into Oblivion Podcast

Sailing Into Oblivion Podcast

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

October 25, 2025 37 mins
Mark as Played

Just a quick show about my time in the yard, keeping my head screwed on, and the upcoming voyage.  Thanks for listening!

Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ

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 Pay...

Mark as Played
October 21, 2025 23 mins

Today we have a quick show from the Murf-files. Murf tells the story of the race day gone wrong and how he ended up in the back seat of a cruiser.  

Check out the Tic-Tok video here: https://www.tiktok.com/t/ZP8A7jwT8/

Support Murf Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion

Mark as Played

Just a quick update on the boat, the plan, and the projects.  Thanks for listening!

Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ

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...

Mark as Played
October 19, 2025 81 mins

Today I sit down with Deborah Hammett, her new book, Young Salt at 60, is the story of how it's never too late to get out and follow your dreams.  Deborah set sail for a Caribbean adventure late in life and that is what we get into during this wonderful conversation. 

Instagram: @youngsalt60

Website: https://www.youngsalt60.com/

Deborah's Book Link: https://a.co/d/g5fAlzA

Total Boat 5% discount code: https://www.totalboat.com/?sca_...

Mark as Played

Today we have the first of many shows with Oliver aka @sailingwithpheonix to talk about the next adventure, a solo non-stop circumnavigation.  I am going to be helping out with the preparations and training.  Thanks for listening.

Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ

Rustbelt 950: https://glexpeditionaryclub.org/rust-belt-950

Support this Podcast on Patreon: https://www.patreon.com/sail...

Mark as Played

Today Brandon joins the show again with more adventures aboard his O-Day Mariner. Check out his newest video on YouTube here: https://youtu.be/5qlyIhTDogI?si=yxsHH7wnzRNOPxgm

Lots of great content on his channel and Insta: @restrothunderroad

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....

Mark as Played
October 6, 2025 42 mins

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....

Mark as Played
September 30, 2025 38 mins

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.co...

Mark as Played
September 26, 2025 26 mins

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 m...

Mark as Played
September 22, 2025 69 mins

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/r...

Mark as Played

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...

Mark as Played

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....

Mark as Played
September 1, 2025 65 mins

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...

Mark as Played

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 Indiana...

Mark as Played

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-bel...

Mark as Played

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 a...

Mark as Played

Well this should be the last of the ocean recordings for a while so today I bring you aboard for the last leg of this voyage that started way back in April down in Florida. It has been a long trip but Sparrow is finally high and dry and getting some much-needed TLC.  Thanks for listening.

October 2nd Indianapolis Show Tickets: https://www.sailingintooblivion.com/new-events-1

Rustbelt 950: https://glexpeditionaryclub.org/rust-belt-9...

Mark as Played

We are in the home stretch but the sea has one more little speed bump in store for the Mighty Sparrow. 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 Donation...

Mark as Played

Here we go with part two of this three-part series sailing from North Carolina to Cape Cod.  Enjoy the show and 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...

Mark as Played

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