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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

01:38:58

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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01:15:22

EP#343 Colin Denker Returns Post Hawaii Passage

Sailing Into Oblivion Podcast ·

2025/06/02

Very excited to have Colin back on the show, fresh off the ocean, and ready to chat about life on the big blue. Always a pleasure to chat with a fellow solo sailor.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 and Venmo: https://www.paypal.com/paypalme/JeromeRand

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01:09:33

EP#342 Introducing the Rustbelt 950 with Jeff

Sailing Into Oblivion Podcast ·

2025/05/31

Today we talk about the creation of what will be an epic freshwater adventure, the Rustbelt 950. I sit down with Jeff; the creator of the event and we talk about the inspirations as well as the fine details that have been laid out so far. The goal is for the first race to start in the summer of 2026, for more information check out the website here: https://glexpeditionaryclub.org/rust-belt-950Instagram: @rustbelt950 Support this Podcast on Patreon:

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01:28:54

EP#341 Guest Appearance on the M42 Adventures Podcast

Sailing Into Oblivion Podcast ·

2025/05/29

Today we have my conversation on the M42 Adventures Podcast. Rick and I chat about the how and why of living an adventurous life. Check out M42 here: https://m42adventures.com/ 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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26:45

EP#340 Back from Work with Friends

Sailing Into Oblivion Podcast ·

2025/05/27

I know it's been a little while but life gets busy and I have been running at full speed for the last few weeks. Just a quick update on things and some thoughts on solitude vs being with friends. 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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40:46

EP#339 Midnight Ramblings and a Call for a Camping Trip

Sailing Into Oblivion Podcast ·

2025/05/15

A solo show here after a long day of prep and work to get the summer underway. If you listen regularly, you know I love the woods and the annual camping trip. Well, if it's been a while since you got out there, then make a plan, if you have never been? This could be the summer to make it happen. Enjoy the show!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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27:26

EP#338 Checking In with @sailingwithPhoenix AKA Oliver

Sailing Into Oblivion Podcast ·

2025/05/13

We had a quick check in last night and I wanted to share the convo with Oliver while he and his cat Phoenix are mid-way from Oregon to Hawaii. Thanks for listening and sharing. 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: https://www.paypal.com/paypalme/JeromeRand

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52:09

EP#337 Spring is in the Air! Boat Prep

Sailing Into Oblivion Podcast ·

2025/05/13

Sometimes it's easy to think of all the task's as overwhelming, all the boat prep, spring cleaning and what-have-you; well we should enjoy the moment before the event as well. Take it in as the summer is upon us. Thanks for listening! Check out Nord Coast on Instagram: @nordcoastco or the Website: https://nordcoastco.com/ Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand

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01:23:00

EP#336 Francesca Clapcich, Olymipian, Americas Cup,...

Sailing Into Oblivion Podcast ·

2025/05/11

Today I sit with Francesca, a sailor that races at the highest level of the sport. We talk about the highs and lows, hard work and the road ahead toward the solo round the world Vendee Globe Race in 2028. Check out here website here: https://www.francescaclapcich.com/2028vendeeglobe 11th Hour Racing: https://11thhourracing.org/ Colin Denker's Tracing Page in the Pacific: https://forecast.predictwind.com/tracking/display/SV-Andromeda/ Support this Podcast on Patreon:

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39:51

EP#335 Back at JeromesTown and Answering a few EMails

Sailing Into Oblivion Podcast ·

2025/05/05

Quick update show and getting into a few questions from some listeners. If you ever want to get my take on anything feel free to visit the Sailling Into Oblivion Website to reach out to the show. Thanks for listening.Support this 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 Amazon

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01:50:29

EP#334 Rutherford Files Continue!

Sailing Into Oblivion Podcast ·

2025/05/01

We have the return of Matt Rutherford on the show today. Always great to sit down with a fellow solo sailor/Ocean Research Project founder. We talk about it all. Thanks for sharing some time and be sure to check out his website here: https://www.oceanresearchproject.org/Support this 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 Amazon

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01:23:55

EP#333 Part 2 Speed Run Recordings

Sailing Into Oblivion Podcast ·

2025/04/28

Here is the second half of the voyage from Fort Pierce to Cape Fear, I hope you enjoy the recordings and thanks for listening and sharing the podcas!Support this 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 Amazon WishList:https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into

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59:45

EP#332 Part Speed Run Offshore Recording

Sailing Into Oblivion Podcast ·

2025/04/26

Today we have the recordings from the last passage from Florida to North Carolina. I was riding the Gulf Stream and had the chance to set a new 24 hour record for miles as well as just enjoy a quick solo trip on the old Mighty Sparrow. Thanks for listening!Support this 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 Amazon

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