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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

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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01:38:58

EP#351 Colin Denker in Person Aboard his new Westsail 32

Sailing Into Oblivion Podcast ·

2025/06/26

Today I sit down with Colin Denker aboard his new Westsail 32! That is right, he is moving from the Pacific to the Atlantic and starting off on new adventures. Always a pleasure to have Colin back on the show. Thanks for listening!Check out his YouTube Channel at: https://www.youtube.com/@colin.denker Instagram: @colin_bos 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

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30:29

EP#350 Last Night Aboard Sparrow, Stay Positive!

Sailing Into Oblivion Podcast ·

2025/06/24

Quick solo show about boats, challenge, and staying upbeat and positive. Thanks for listening!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

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33:58

EP#349 Why I Go Sailing

Sailing Into Oblivion Podcast ·

2025/06/20

Back aboard Sparrow and instead of the normal welcome home podcast, I have something a bit different, a bit deeper if you will. My thoughts on just what drives me to go out to sea over and over again. Thanks for listening. 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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01:18:34

EP#348 Charley and Kayleigh Bahamas to Dominican...

Sailing Into Oblivion Podcast ·

2025/06/16

Today I sit down once again with Charley and Kayleigh, this time from the DR after a cruising season in the Bahamas. Always a pleasure to hear about the continuing adventures of these two sailors. Let hope for a quiet hurricane season as they settle into the island life for the next few months! 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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03:10:11

EP#347 From Indiana to L.A. Emmy Award Winning...

Sailing Into Oblivion Podcast ·

2025/06/11

Today we sit down with Robert Malachowski and talk about his journey from growing up in Indiana, moving to L.A., and finally finding himself and his team accepting an Emmy Award for the great work on The Voice. This is a lesson in hard work and perseverance when facing down challenges as well as following our dreams. Big thanks to Robert for taking his time and share an incredible experience. Robert's IMDb: https://www.imdb.com/name/nm1159644/ Support this Podcast on Patreon:

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51:40

EP#346 Solo Show; To Live a Life of Adventure?

Sailing Into Oblivion Podcast ·

2025/06/08

Today I answer an email from Ben, the question being, do I go after my dreams now or take the normal walk down life's path? Well lets get into! Thanks for listening.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

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01:03:53

EP#345 Landfall Podcast with Oliver @sailingwithphoenix

Sailing Into Oblivion Podcast ·

2025/06/06

Today we have our third sit-down with Oliver after making landfall in Hawaii. We talk about the trip, food, and what the future adventure looks like after going viral while out at sea. Big thanks to Oliver for taking some time to share his story.Check out Oliviers Instagram and YouTube: @sailingwithphoenix 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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01:44:06

EP#344 Circumnavigating with @SailorJames

Sailing Into Oblivion Podcast ·

2025/06/04

Today I sat with Sailor James all the way over in Indonesia! He has been on the oceans making his way around the world and sharing the experience via YouTube, social media and writing. A wonderful time chatting about life on the big ocean and coastal cruising. Check out his Website here: https://www.svtriteia.com/ @sailorJames on Youtube and Instagram @james.the.sailor.man Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast Help fund my next adventure here:

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