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

May 5, 2025 39 mins

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

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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/Jero...

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April 28, 2025 83 mins

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.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?...

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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://...

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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 Captain or a better vessel.  Cheers!

Check out Marc's YouTube Channel here: https://www.youtube.com/@SailingSVMonta%C3%B1a

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

One Time Donations Via PayPal...

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April 17, 2025 32 mins

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

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:/...

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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 and open insights and sharing his time.  Thanks for listening.

Check out Elliot's Rigging Company here: https://nonstoprigging.com/ 

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

One Time Donations V...

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Here we go folks, I have tried my best to shed some of my own insight into getting out of a rut and back to our happy place in life.  I have dealt with post adventure depression for years and come up with some of the key points that help me to get back on track.  If this helps one person then I have done my job.  These shows are not easy to put out into the world, lot of self doubt when it comes to wheather this is wisdom or just B...

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March 30, 2025 43 mins

After five grueling days ripping the San Diego Bay, I sit down with Justin to talk about how the coaching session went. From my end it was amazing, we had great weather, a nice boat and best of all, good company. Big thanks to Justin for the hospitality and showing me around SD, can't wait to get back on board East Coast style.  Enjoy the show. 

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

One...

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March 28, 2025 31 mins

Hey everybody, just wanted to do a quick update show while I am out here on the West Coast on a coaching trip. The schedule is busy, but it has been a blast sailing in new waters and meeting some great people. 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/saili...

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Today I want to make a case for starting your adventure now. After speaking with so many people who have reached their goals or who are working hard to get to them, I'm feeling inspired. And if anything in this show rings a bell or helps to get you moving to chase after your dreams, well, my job here is done. I hope you enjoy this podcast and thanks for listening.

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

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Today we have a very special guest on the podcast, I have wanted to sit and chat with Kirsten Neuschafer, winner of the GGR 2022, for a long time and was so happy when we were both on land and could make it happen.  We chat about everything from some of the technical parts of her boat to how both she and I deal with overwhelming odds and tough times. It was an honor to sit and talk with such an amazing sailor!  Thanks for listening...

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Today I sit down with Josh Wright and talk about his adventures crossing solo to Hawaii and then joining another boat to sail all the way to Japan. Josh has some great insight into the mind of solo sailing and was a pleasure to sit and chat with. We will for sure be talking again in the future!  Thanks for listening.

Check out his Instagram and YouTube channel here: https://www.instagram.com/joshwrightsailing/?hl=en https://www.you...

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Today I sit down with Oliver and talk about his big plans to cross from Oregon to Hawaii starting in a few short weeks. Oliver has been documenting the learning process aboard his Com-Pac 33 in a very authentic and upfront way. I wish him the best of luck and can't wait to have a follow-up show after the crossing. Thanks for listening.

Check out @sailing_with_pheonix YouTube here: https://www.youtube.com/@Sailing_With_Phoenix

Insta...

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Today we talk about the concept of how setting specific goals in life unlock a path to success and perhaps more importantly, a feeling of purpose.  I use examples from some of my trips to shed some light on the subject.  Thanks for listening and your continued support!

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

One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRa...

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Today we have Colin Denker back on the show as he prepares for the solo trip to Hawaii from San Francisco. Always a pleasure to chat with Colin and I wish him the best of luck with the upcoming adventure! Check out his video about the trip down the West Coast here: https://www.youtube.com/watch?v=Q5fZcBC__gc

March 5th Show in Madison Wi: https://www.hoofersailing.org/

March 7th Show in Chicago: https://corinthian.org/content.aspx?p...

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Today, I get into the wrap up of the last few months and how things went well and not so well, but learning all the way. I say farewell to Sparrow for the next month and much more.  Thanks for listening!

March 5th Show in Madison Wi: https://www.hoofersailing.org/

March 7th Show in Chicago: https://corinthian.org/content.aspx?page_id=4091&club_id=845458&item_id=2481856

Support this Podcast on Patreon: https://www.patreon.co...

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Well folks, you made it, if you have listened to all of these, you deserve a gold star! Back to the regular schedule of one or two shows a week.  Thanks for listening and I hope you enjoyed sailing with me aboard Sparrow.

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/sailingintooblivi...

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We are moments away from spotting land and finishing this voyage up, 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 WishList:https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share

Children's Book: https://a.co/d/1q2Xkev

Sailin...

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February 20, 2025 25 mins

Getting into the dog days f the trip at this point, 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 WishList:https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share

Children's Book: https://a.co/d/1q2Xkev

Sailing Into Oblivion C...

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