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

September 6, 2025 44 mins

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

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

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

Rustb...

Mark as Played
August 5, 2025 31 mins

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...

Mark as Played
August 3, 2025 12 mins

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 ...

Mark as Played
July 28, 2025 57 mins

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 P...

Mark as Played

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...

Mark as Played
July 18, 2025 22 mins
Getting ready, start is a few hours away! Thanks for listening.
Mark as Played

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 V...

Mark as Played

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 ...

Mark as Played

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/@passagesfromtheheart

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.pay...

Mark as Played

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 adven...

Mark as Played

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/33F36RF3...

Mark as Played
June 19, 2025 33 mins

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/...

Mark as Played

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