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Carlos Valencia stops by to educate Jason about life as a road comic. This is one of those conversations about comedy that comedians will really enjoy. The rest of you and my mother should listen as well.

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The incomparable, intelligent and always hilarious Janet Williams (A.K.A. Tennessee Tramp) Joins Jason to talk comedy, race, religion, politics, criminal counseling and more comedy. Janet’s natural curiosity about life and her love of people make her an ideal guest on the show. Plus, she proves her willingness to try anything because before today, she didn’t seem to fully grok what a podcast even was!

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Activist, Veteran, and fellow boarding school survivor Wes Clark Jr. calls Jason to compare notes on how each has spent the last 30 years. Wes won. His life has been way more compelling and now he is a hero to many, including Jason.

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TV writer, comedian, playwright & intellectual, David Castro, visits Jason to spin yarn about the old days of Hollywood in a hilarious and informative conversation about how he got his start. But not before they cover issues of race, economic inequality, revisionist history, and the importance of honoring the past while determining how best to integrate it into the present.

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Jason sits down with the incomparable Sean Patton, the day after they perform together at The Grey Eagle in Asheville. If you’re unfamiliar with his work, Sean is one of the more amazing comedians on the road today. Lots of young headlining comedians put Sean in their top 5.  Today you will hear him talk about his past, his present, and witness him conjuring up several funny riffs and bits out of thin air, on the air! If you’re a comedian, this is a can’t miss interview. If you’re a fan of comedy, this is a can’t miss interview. If you like the sound of Jason’s voice, this is a can’t miss interview because Sean even has a few funny things to say about that!

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Kelly Kreye and Dale Krupla crash in Jason’t guest room, eat a bunch of pancakes, and talk about their life on the road filming Season 2 of Dave Made Me Do It — a documentary style YouTube series about the various open mic comedy scenes in America. Asheville showed them a pretty good time, and they lived to tell about it. Jason and his daughter, Sula, feature heavily in their episode on Asheville. If you ever wanted to hear what 3 dudes talk about when they think nobody’s listening, here’s your chance. We think you’ll enjoy listening to this episode. Jason's mother, most likely, will not.

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Road comic extraordinaire, Julie Scoggins, sits down with Jason between shows to discuss politics, religion, and most importantly, comedy. Julie is is a 19-year veteran comedian, and had a lot of great tips for Jason. She’s also just really down to earth and fun to talk to. Her personality on stage is as delightful as it is in person. She’s just a pleasure to know and listen to, as you’re about to find out. Funny, frank and unafraid, Julie has a voice that brightens every room.

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Yoga teacher and physical therapist, Ryan Conrad, joins Jason to talk about everything you might want to say and do when you’ve been told you only have 18 months to live. This interview took place about 6 months after Ryan found out he had Pancreatic Cancer, and about a year before he died. It is part of the legacy he leaves behind for his son, Harper Reed. But hey, don’t get depressed. This is a fun and funny episode, with two guys swapping stories and talking about the things in life that truly matter. This conversation gives the very existence of Learning To Fail reason for being.

If you feel inspired to donate after hearing this conversation, please consider contributing to Ryan's son, Harper Reed’s college fund. The information on how to make a donation can be found here.

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LTF Podcast producer, Adam Fields, joins Jason in the studio to discuss the feelings he has in the wake of the 2016 Election results. Together, they try to make sense of it all. They tap into the nature and structure of existence, and how karma, dharma and lila may have played integral roles in the political process. Or was it all just God’s will? If you like philosophy and ideas and if you’re allergic to or have a strong affinity for spirituality, this episode is a must-hear.

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Jason sits down with Voiceover Artist, Fine Woodworker, old friend and mentor, Scott Peterson, for a trip down memory boulevard. The streets are adorned with good times, bad ideas and wounds that needed healing. If you fail to learn from Scott, you can’t Learn to Fail from anyone.