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Sailing Into Oblivion Podcast - 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.

Society & Culture Sports Places & Travel Wilderness
Update frequency
every 3 days
Average duration
59 minutes
Episodes
373
Years Active
2020 - 2025
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EP#348 Charley and Kayleigh Bahamas to Dominican Republic

EP#348 Charley and Kayleigh Bahamas to Dominican Republic

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. Le…

01:18:34  |   Mon 16 Jun 2025
EP#347 From Indiana to L.A. Emmy Award Winning Editor, Robert Malachowski

EP#347 From Indiana to L.A. Emmy Award Winning Editor, Robert Malachowski

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…

03:10:11  |   Wed 11 Jun 2025
EP#346 Solo Show; To Live a Life of Adventure?

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

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:…

00:51:40  |   Sun 08 Jun 2025
EP#345 Landfall Podcast with Oliver @sailingwithphoenix

EP#345 Landfall Podcast with Oliver @sailingwithphoenix

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…

01:03:53  |   Fri 06 Jun 2025
EP#344 Circumnavigating with @SailorJames

EP#344 Circumnavigating with @SailorJames

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 ti…

01:44:06  |   Wed 04 Jun 2025
EP#343 Colin Denker Returns Post Hawaii Passage

EP#343 Colin Denker Returns Post Hawaii Passage

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:…

01:15:22  |   Mon 02 Jun 2025
EP#342 Introducing the Rustbelt 950 with Jeff

EP#342 Introducing the Rustbelt 950 with Jeff

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 …

01:09:33  |   Sat 31 May 2025
EP#341 Guest Appearance on the M42 Adventures Podcast

EP#341 Guest Appearance on the M42 Adventures Podcast

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 o…

01:28:54  |   Thu 29 May 2025
EP#340 Back from Work with Friends

EP#340 Back from Work with Friends

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.  T…

00:26:45  |   Tue 27 May 2025
EP#339 Midnight Ramblings and a Call for a Camping Trip

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

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…

00:40:46  |   Thu 15 May 2025
EP#338 Checking In with @sailingwithPhoenix AKA Oliver

EP#338 Checking In with @sailingwithPhoenix AKA Oliver

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 In…

00:27:26  |   Tue 13 May 2025
EP#337 Spring is in the Air! Boat Prep

EP#337 Spring is in the Air! Boat Prep

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 summ…

00:52:09  |   Tue 13 May 2025
EP#336 Francesca Clapcich, Olymipian, Americas Cup, Ocean Race, now Vendee Globe 2028 Sailor Sailor

EP#336 Francesca Clapcich, Olymipian, Americas Cup, Ocean Race, now Vendee Globe 2028 Sailor Sailor

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…

01:23:00  |   Sun 11 May 2025
EP#335 Back at JeromesTown and Answering a few Emails

EP#335 Back at JeromesTown and Answering a few Emails

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.  T…

00:39:51  |   Mon 05 May 2025
EP#334 Rutherford Files Continue!

EP#334 Rutherford Files Continue!

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…

01:50:29  |   Thu 01 May 2025
EP#333 Part 2 Speed Run Recordings

EP#333 Part 2 Speed Run Recordings

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 podcast!

Support this Podcast on Patreon: https://www.pat…

01:23:55  |   Mon 28 Apr 2025
EP#332 Part 1 Speed Run Offshore Recording

EP#332 Part 1 Speed Run Offshore Recording

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 …

00:59:45  |   Sat 26 Apr 2025
EP#331 Offshore Atlantic Sailing With Marc

EP#331 Offshore Atlantic Sailing With Marc

Today I bring you the post adventure chat with Marc after our nearly 2,000 mile offshore trip aboard his Westsail 32. We had a great time sailing the high seas and I couldn't have asked for a better …

00:56:15  |   Tue 22 Apr 2025
EP#330 Back on Land, for Only a Day

EP#330 Back on Land, for Only a Day

Here is a little update after the last trip, in depth podcast about the trip coming soon.  Thanks for listening!

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

On…

00:32:36  |   Thu 17 Apr 2025
EP#329 Elliot Smith Returns to the Show

EP#329 Elliot Smith Returns to the Show

While in San Diego I met up with Elliot Smith for a return podcast to check in and see how life is going. We talk about past adventures, letting go, and moving forward.  Really applicate his honest a…

01:32:38  |   Sun 06 Apr 2025
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