Jesse May
Reckless Success
Jesse May lived life on the edge, leading him to being sentenced to 87 months in federal prison. Jesse will share stories from his reckless past and how he progressed from prison to successful entrepreneur in 5 years. Fellow business owners and lifelong friends will join Jesse throughout the podcast.
Author
Jesse May
Category
Podcast website
Latest episode
Jul 25, 2025
Where to listen?
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Episodes
Episode 13: Giner Gummies 03.03.2024 40:49
Jesse shares stories of being chased by a purple Cadillac with gold rims and wrecking his Raptor over a bag of marijuana tops. Then, Tyler Larson, owner of Arrow and Plank, discusses how he stopped traveling for work to start his own specialty carpentry business. Find Tyler on: Facebook - https://www.facebook.com/arrowandplank/ Instagram - tycrafterlarson YouTube - www.youtube.com/@UCM_uDE_sm91Yfc...
Episode 12: My One-Eyed Friend 25.02.2024 46:14
Jesse shares stories with Lesa about his friend, Cyclops, before they discuss addiction risks in families. Jesse & Lesa discuss how they grew their business. Check out HONESTAV on social media. His entire playlist on Spotify is incredible. Jesse May lived life on the edge, leading him to being sentenced to 87 months in federal prison. Jesse will share stories from his reckless past and how he...
Episode 11: Flat Tail Stories 18.02.2024 1:09:04
Robert Dill, owner of Flat Tail Metal Works, joins Jesse to talk black panthers, stolen dogs, double-decker hunting trucks, and metal fabrication, including aluminum welding. Contact Flat Tail Metal Works on Facebook or e-mail flattailmetalworks@gmail.com Jesse May lived life on the edge, leading him to being sentenced to 87 months in federal prison. Jesse will share stories from his reckless past...
Episode 10: This Is Where Stuff Gets Broke 11.02.2024 1:13:49
Jesse, Justin, and Chad discuss the unstable snowpack, injuries, -38 degree temperatures, and adventures they had on their annual snowmobile trip to West Yellowstone. Jesse May lived life on the edge leading him to being sentenced to 87 months in federal prison. Jesse will share stories from his reckless past and how he progressed from prison to successful entrepreneur in 5 years. https://www.maye...
Episode 9: You've Done A Lot of Work to That Thing 04.02.2024 1:22:18
Jesse shares how his meth addiction began, the process of being federally indicted, and a glimpse into adapting to prison life after he shares wild stories with our producer and owner of Union Street Arts, Luke O'Neill. Find Luke at www.unionstreetarts.com for all your videography, podcast, or wedding video needs. Jesse May lived life on the edge leading him to being sentenced to 87 months in...
Episode 8: Mom, It's a Party 28.01.2024 1:02:22
Jesse shares stories about helping his friend spend $130,000, going to Mardi Gras as a teenager, and schemes to make more money. Then, Jesse and Lesa discuss the importance of building relationships and handling difficult situations. Jesse May lived life on the edge, leading him to being sentenced to 87 months in federal prison. Jesse will share stories from his reckless past and how he progressed...
Episode 7: The High Road to Success 21.01.2024 1:08:00
Owner of Skaggs Builder, Phillip Skaggs, shares how he overcame an opiate addiction to build a successful construction company. Jesse and Phillip discuss their upbringing and how they changed the direction of their lives after hitting rock bottom. Follow Skaggs Builder: YouTube - @SkaggsBuilder Instagram - @skaggsbuilder Jesse May lived life on the edge, leading him to being sentenced to 87 mont...
Episode 6: Catch Me If You Can 14.01.2024 1:11:19
Jesse shares stories about close calls with the police and fleeing on his four-wheeler before Jesse and Lesa discuss how your presentation impacts your business. Jesse May lived life on the edge, leading him to being sentenced to 87 months in federal prison. Jesse will share stories from his reckless past and how he progressed from prison to successful entrepreneur in 5 years. https://www.mayexcav...
Episode 5: Dirty Hands, Clean Money 07.01.2024 1:32:00
Owner of Southern Illinois Excavators, Justin May, and Jesse discuss their excavation businesses, highs and lows of being self-employed, and how they each started out. Jesse May lived life on the edge leading him to being sentenced to 87 months in federal prison. Jesse will share stories from his reckless past and how he progressed from prison to successful entrepreneur in 5 years. https://www.may...
Episode 4: Hot for Teacher 30.12.2023 1:37:36
Multi-business owner and friend, Chad Skaggs, talks off-roading, jet boating, high school, and everything in between, before Jesse shares run-ins with the police and a look at life in federal prison. Jesse May lived life on the edge leading him to being sentenced to 87 months in federal prison. Jesse will share stories from his reckless past and how he progressed from prison to successful entrepre...
Episode 3: Fleeing to Mexico 30.12.2023 35:04
Jesse shares a story of the time he fled to Mexico and Jesse and Lesa give a quick introduction to the podcast and a timeline of Jesse ending up in federal prison and bring released. Jesse May lived life on the edge leading him to being sentenced to 87 months in federal prison. Jesse will share stories from his reckless past and how he progressed from prison to successful entrepreneur in 5 years....
Episode 2: Fighting in a Small Town 29.12.2023 39:32
Episode 2 of Reckless Success Army Veteran, lifelong friend, and business owner, TJ Hale, joins Jesse to share wild stories from their childhood and how he started a Veteran Owned Small Business. Jesse May lived life on the edge leading him to being sentenced to 87 months in federal prison. Jesse will share stories from his reckless past and how he progressed from prison to successful entrepreneur...
Episode 1: Police Raids 29.12.2023 1:01:09
Episode 1 of Reckless Success Jesse shares a story of being raided years before his federal indictment, followed by business talk with his wife and business partner, Lesa. Jesse May lived life on the edge leading him to being sentenced to 87 months in federal prison. Jesse will share stories from his reckless past and how he progressed from prison to successful entrepreneur in 5 years. https://www...
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