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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:

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All Episodes

26:05

EP#371 Off to New York for some Sailing

Sailing Into Oblivion Podcast ·

2025/09/26

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

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69:07

EP#370 Buying and Selling Boats with Chelle

Sailing Into Oblivion Podcast ·

2025/09/22

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:

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41:59

EP#369 Camping Trip Wrap-up, the Brutality on Mother...

Sailing Into Oblivion Podcast ·

2025/09/09

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

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44:23

EP#368 Guest Appearance on the Really Riveting...

Sailing Into Oblivion Podcast ·

2025/09/06

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

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65:58

EP#367 Colin Denker Returns Once Again

Sailing Into Oblivion Podcast ·

2025/09/01

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:

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88:10

EP#366 Coaching and Training with Author Francesca...

Sailing Into Oblivion Podcast ·

2025/08/29

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:

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01:07:41

EP#365 Conversation with Murf, Rockland Maine

Sailing Into Oblivion Podcast ·

2025/08/23

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:

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35:03

EP#364 Yard Period Done, Back to JeromesTown

Sailing Into Oblivion Podcast ·

2025/08/21

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

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01:06:26

EP#363 Cape Cod to Rockland Maine Coastal Recordings

Sailing Into Oblivion Podcast ·

2025/08/16

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-950 Support this Podcast on Patreon:

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01:12:02

EP#362 Offshore Recordings NC to Cape Cod Part Three

Sailing Into Oblivion Podcast ·

2025/08/14

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 Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand

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01:05:00

EP#361 Offshore Recordings Part 2 NC-Cape

Sailing Into Oblivion Podcast ·

2025/08/11

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 Donations Via PayPal and Venmo:

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01:11:03

EP#360 Offshore Recordings Part One, NC-Cape Cod

Sailing Into Oblivion Podcast ·

2025/08/07

Today we are getting into the heat and despair of sailing mid-summer in the Atlantic Ocean. This is going to be a bunch of short recordings as I couldn't sit below and cook for all that long during the worst of the heat. Its a battle sometimes but I can say with confidence that the suffering was worth it in the end. 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

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31:39

EP#359 It Was A Long Night

Sailing Into Oblivion Podcast ·

2025/08/05

Well we have made the safety of port once again, thanks to the never-ending strength of the Mighty Sparrow. Offshore recordings coming soon, 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:

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12:42

EP#358 Long Night Ahead

Sailing Into Oblivion Podcast ·

2025/08/04

Well it took longer than I thought but I’m sailing into Nantucket sound as I record this. Just a quick update for tonight and soon the offshore recordings will be 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

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57:23

EP#357 Getting Sparrow Ready to Sail

Sailing Into Oblivion Podcast ·

2025/07/28

Today we get into the process of bring Sparrow back to life and getting her ready for the high seas. Hoping for a fun and quick trip north the Cape Cod. I'm under the gun with time but am confident that Sparrow will rise to the occasion. 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

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34:24

EP#356 Sparrow, Here I Come! Time to hit the Road

Sailing Into Oblivion Podcast ·

2025/07/23

Today I chat about the upcoming trip to Cape Cod from North Carolina and all the prep and planning that is needed between now and departure in just a few days. These small passages still require a ton of planning to be safe and successful, so its time to get to work. Thanks for listening.October 2nd Indianapolis Show Tickets: https://www.sailingintooblivion.com/new-events-1 Rustbelt 950: https://glexpeditionaryclub.org/rust-belt-950 Brandon's YouTube Channel:

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22:29

Ep#355 Pre-Race With Dobbs

Sailing Into Oblivion Podcast ·

2025/07/18

Getting ready, start is a few hours away! Thanks for listening.

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01:13:52

EP#354 The Texas 200, Lightning, and Adventure with...

Sailing Into Oblivion Podcast ·

2025/07/13

Today, I sit down with Brandon and chat about the Texas 200. Not a race but an adventure for sure. In his 4th round of the event, Brandon and his brother were caught out in some nasty weather with one of the scariest elements of sailing becoming a reality, lightning! Big thanks to Brandon for sharing his story and all the info about the Texas 200. Thanks for listening.Check out the Texas 200 here: https://texas200.com/ Brandon's Video on YouTube:

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01:19:07

EP#353 Rutherford Files from the Top of the World

Sailing Into Oblivion Podcast ·

2025/07/07

Today we catch up with Matt Rutherford while he waits out some bad weather up at the top of the world. Always a pleasure to see how the adventure is going aboard the Marie Tharp. Check out the OceanResearchProject here: https://www.oceanresearchproject.org/ 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

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01:12:55

EP#352 Coaching on Lake Superior with Chelle and Ben

Sailing Into Oblivion Podcast ·

2025/07/02

Happy 4th of July Week! Today we have a post-con with Chelle and Ben after a three-day coaching trip aboard their Com-Pac 25. Check out the Passages from the Heart YouTube Channel here: https://www.youtube.com/@passagesfromtheheartSupport 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

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