Ep#355 Pre-Race With Dobbs
Getting ready, start is a few hours away! Thanks for listening.
Jul 18, 2025•22 min
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.
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Episodes
EP#354 The Texas 200, Lightning, and Adventure with Brandon
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: https://www.youtube.com/watch?v=WUUZfe_Mw_w&...
Jul 13, 2025•1 hr 14 min•Ep. 367
EP#353 Rutherford Files from the Top of the World
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 https://accou...
Jul 07, 2025•1 hr 19 min•Ep. 366
EP#352 Coaching on Lake Superior with Chelle and Ben
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.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailinginto...
Jul 02, 2025•1 hr 13 min•Ep. 365
EP#351 Colin Denker in Person Aboard his new Westsail 32
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...
Jun 26, 2025•1 hr 39 min•Ep. 364
EP#350 Last Night Aboard Sparrow, Stay Positive!
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 Saili...
Jun 24, 2025•30 min•Ep. 363
EP#349 Why I Go Sailing
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 https://account.venmo.com/u/sailingintooblivion ...
Jun 20, 2025•34 min•Ep. 362
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. 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: https://www.paypal...
Jun 16, 2025•1 hr 19 min•Ep. 361
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 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: https://www.patreon...
Jun 11, 2025•3 hr 10 min•Ep. 360
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: 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/33...
Jun 08, 2025•52 min•Ep. 359
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 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: https...
Jun 06, 2025•1 hr 4 min•Ep. 358
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 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: https:...
Jun 04, 2025•1 hr 44 min•Ep. 357
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: 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 https://acco...
Jun 02, 2025•1 hr 15 min•Ep. 356
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 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-950 Instagram: @rustbelt950 Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpod...
May 31, 2025•1 hr 10 min•Ep. 355
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 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/wis...
May 29, 2025•1 hr 29 min•Ep. 354
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. 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 Amazo...
May 27, 2025•27 min•Ep. 353
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 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: h...
May 15, 2025•41 min•Ep. 352
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 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 https://account.venmo.com/u/sail...
May 13, 2025•27 min•Ep. 351
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 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 https://...
May 13, 2025•52 min•Ep. 350
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 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: https://www.patreon.com/saili...
May 11, 2025•1 hr 23 min•Ep. 349
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. 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/33F36RF315G...
May 05, 2025•40 min•Ep. 348
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 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 WishL...
May 01, 2025•1 hr 50 min•Ep. 347
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.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 In...
Apr 28, 2025•1 hr 24 min•Ep. 346
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 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 WishList: https://w...
Apr 26, 2025•1 hr•Ep. 345
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 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 and Venmo: https://www.paypal.com/paypalme/JeromeRand https://acc...
Apr 22, 2025•56 min•Ep. 344
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 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 Children's Audio Book: Audi...
Apr 17, 2025•33 min•Ep. 343
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 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 Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand http...
Apr 06, 2025•1 hr 33 min•Ep. 341
EP#330 Getting Back on the Horse and Out of the Rut
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 BS, I hope you find it helpful. Thanks for listening. Support this Po...
Apr 01, 2025•57 min•Ep. 342
EP#328 San Diego Sailing with Justin
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 Time Donations Via PayPal and Venmo: https://www.paypal.com/paypal...
Mar 31, 2025•44 min•Ep. 340
EP#327 Update from the West Coast
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/sailingintooblivion Amazon WishList: https://www.amazon.com/hz/wishlist/...
Mar 28, 2025•31 min•Ep. 339
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