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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.

Jesse May


    • Feb 9, 2025 LATEST EPISODE
    • monthly NEW EPISODES
    • 1h 4m AVG DURATION
    • 37 EPISODES


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    Latest episodes from Reckless Success

    Episode 37: Marlboro Man

    Play Episode Listen Later Feb 9, 2025 138:53


    Back after a holiday break, Jesse and Chad catch up on the Midwest ice storm, President Trump, Jesse's health scare, Marlboro Merch from the 90s, hippie encounters, and so much more.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. He does not condone or recommend any reckless behavior shared in these stories.https://www.mayexcavating.com/Follow us on social media:Tiktok :  / reckless.success  Instagram: @RecklessSuccessIntro song: Put Em in They Place by Matt Cormanwww.mattcorman.com

    Episode 36: Hot Rod

    Play Episode Listen Later Nov 24, 2024 35:23


    Jesse shares stories about tormenting his stepdad while living in his parent's basement during his drug using days. Then, Jesse and Lesa give an update on the commercial projects they've been working on for the excavating 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok :   / reckless.success   Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 35: Chapel Isn't a Safe Place

    Play Episode Listen Later Nov 10, 2024 69:05


    Jesse is joined by new friend Chris Boland who served 12 years in Federal Prison in Texas after a wild ride in his 20s. They share about their time in prison, the halfway house, and acclimating to life outside prison walls. Special Background Guest Teddy Brown. 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok :   / reckless.success   Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 34: Everybody Loves Watermelon

    Play Episode Listen Later Oct 13, 2024 31:34


    Jesse and Lesa are in the spirit of Halloween as Jesse elaborates on his story of owning a trailer in Colp & the watermelon wagon. They discuss risks of drinking alcohol, encountering drugs after quitting, and touch base on upcoming excavation work. 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 33: Chemical Romance

    Play Episode Listen Later Sep 29, 2024 61:28


    Veteran and friend, Mitchell Wright, joins Jesse to discuss falling into addiction after being injured in Afghanistan and how he overcame it. Jesse shares stories about some of the dangerous activities that sent him to federal prison, including learning to tap anhydrous tanks. 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok :   / reckless.success   Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 32: Tow Truck Chronicles

    Play Episode Listen Later Sep 15, 2024 61:13


    Jesse talks about reading his Motion of Discovery from his Federal indictment and stories of his long history with tow truck drivers before Jesse & Lesa discuss commercial bidding and their new storage unit 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok :   / reckless.success   Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 31: Get Your Mind Right

    Play Episode Listen Later Sep 1, 2024 75:17


    Intuitive Reader and counselor, Gizelle Luccio - MA, CADS II, QMHP, joins Jesse as he shares how prison helped him get in touch with his spirituality and open up his mind to the Bible, healing, and energy. Jesse & Gizelle each share unexplainable experiences they've had in their lives, how they've grown and made changes, and ways they try to help people now. Gizelle shares her religious path taking her from Catholicism to Seminary to becoming a Quaker and now helping and healing people with her spiritual gifts. Learn more about Gizelle at: www.raven-light.com www.soulnavigation.net 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 30: What Happens in Vegas, Stays in Vegas

    Play Episode Listen Later Aug 11, 2024 37:37


    Jesse and Lesa talk about Jesse's 40th birthday celebrations before discussing hurdles they've encountered when bidding commercial jobs. 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok :   / reckless.success   Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 29: Blondes Have More Fun

    Play Episode Listen Later Jul 28, 2024 54:24


    Lesa is joined by her best friend and fellow business owner, Leah, to discuss their upbringing, breaking cycles, work ethic, trips to Las Vegas, and having good, clean fun. Have no fear, Jesse will be back on Episode 30! 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 28: Is That a Rack of Ribs in Your Pants, or Are You Happy to See Me?

    Play Episode Listen Later Jul 14, 2024 82:19


    Jesse brings longtime friend and businessowner, Ben Mace, on to tell hilarious and dangerous stories from the throes of addiction and discuss recovery and relapse. They touch on gas station adventures, fighting blind men, crack palace trailers, and psychedelics. Ben shares about moving to Miami for rehab, building a homemade cold plunge out of a freezer, custom car building, jiu-jitsu training, and being a single father. Check out Ben's custom car building and IT business on Instagram: @nitrogearhead https://www.instagram.com/nitrogearhead?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw== 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 27: Outlaw by Age 9

    Play Episode Listen Later Jun 30, 2024 53:58


    Jesse shares about his first police chase at age 9, four-wheeler adventures, and scary encounters partying with his dad and friends before Lesa discusses their excavation business getting Certified Women-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 in 5 years. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 26: Party in Your 20s, Hangover in Your 30s

    Play Episode Listen Later Jun 16, 2024 56:28


    Jesse is joined by friend and business owner, Eric Speakman, to learn about his path to opening Leading Edge Fire & Water Restoration. They discuss handling competition, investing in the right tools, and building a team of the right people to grow your business. Check out Leading Edge at https://le-restoration.com/ https://www.facebook.com/lefireandwater 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 25: Booty Bandit

    Play Episode Listen Later Jun 2, 2024 52:52


    Jesse discusses his close calls with the Booty Bandit and a brutal dirt bike wreck before Jesse and Lesa give a quick update on life. 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok :   / reckless.success   Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 24: When Customers Murder Your Friends

    Play Episode Listen Later May 20, 2024 85:25


    Justin May, owner of Southern Illinois Excavators, joins Jesse to discuss working through rainy season and lowboy mishaps before Jesse talks about the customer who murdered his friend and their West Side Story altercations through the years. Find Justin at www.southernillinoisexcavators.com or on Facebook 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 23: Hammer Time

    Play Episode Listen Later May 12, 2024 69:15


    Jesse and Lesa give an update on the arrested jet boat buyer, share stories about career criminals and a front yard brawl, before sharing their negative experience with real estate auctions. 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok :   / reckless.success   Instagram:   / recklesssuccess   @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 22: Network for the Net Worth

    Play Episode Listen Later May 5, 2024 83:24


    Business owner and author of From the Streets to the Throne, Eugene "Teddy" Willingham, joins Jesse to talk about changing their lives after prison, influencing men in today's society, and finding priorities to pull them away from the wrong path. Find Teddy's Micro Bullies on Instagram Willingham Exotic Bullies (@willinghamexoticbullies) • Instagram photos and videos On Facebook Teddy Willingham Asog Or e-mail: eugene_willingham@yahoo.com Teddy's book, From the Streets to the Throne is available on Amazon. 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok :   / reckless.success   Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 21: Canceled Check for the Cocaine

    Play Episode Listen Later Apr 28, 2024 57:19


    The buyer of the mini jet boat gets arrested outside while Jesse and Lesa record this episode! First, Jesse and Lesa discuss getting into real estate investing and Jesse talks about job site accidents with loose cannon co-workers. Then, the buyer of the mini jet boat gets pulled over outside the studio after driving 3.5 hours and ends up in jail. 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 20: Branching Out With Clearview Tree Services

    Play Episode Listen Later Apr 21, 2024 49:17


    Nathaniel White, owner of Clearview Tree Services, joins Jesse to discuss the start of his business, equipment upgrades, nuclear power plant work, and mishaps Jesse has had on job sites. Find Clearview Tree Services on Facebook 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 19: Reunited and It Feels So Good

    Play Episode Listen Later Apr 14, 2024 54:24


    Jesse and Lesa share how they ended up back together after an 8 year break up that included prison time and cross country moves. Then, they share about the time they were caught together as kids and an APB was put out for 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok :   / reckless.success   Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 18: First Class on Con Air

    Play Episode Listen Later Apr 7, 2024 95:55


    Jesses discusses getting in trouble in federal prison causing him to be transferred numerous times on Con Air, becoming Pod Boss in Elmore County Jail, and an inside look at prison life. Wes Lawrence, owner of Next Level Tint and Next Level MX, discusses his businesses, bike week, and his RC Track. Find Wes at www.facebook.com/nextlevelwindowtint 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 17: Prison Pie

    Play Episode Listen Later Mar 31, 2024 60:27


    Jesse talks about the time he befriended a heroin addict from Chicago and brought him back to Southern Illinois and about his friendship with Dirty Shane. Lesa and Jesse discuss ways they have improved their lives personally and professionally over the years. 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 16: Cranes, Barges, & Pile Drivers

    Play Episode Listen Later Mar 24, 2024 70:49


    Jesse and pile driver buddies, Mike Nasers and Mike Lucht, discuss the most difficult jobs they've worked on throughout their careers, river work, and crane work before discussing hotel horror stories. Jesse and Mike share fighting stories from their past. 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 15: Rainbow Festival

    Play Episode Listen Later Mar 17, 2024 48:36


    Jesse and Lesa discuss their purchase of a 750K dozer and scams they've come across after discussing their accidental hangout at a Rainbow Festival, wild stories from their youth, and putting themselves in sketchy 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 from prison to successful entrepreneur in 5 years. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok :   / reckless.success   Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 14: My Lesbian Girlfriend

    Play Episode Listen Later Mar 10, 2024 64:16


    Jesse tells Lesa about the time he dated a lesbian, then they discuss finding and buying used heavy equipment and issues they've run into. 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 13: Giner Gummies

    Play Episode Listen Later Mar 3, 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_sm91Yfc7tI4ZrfZA 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. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 12: My One-Eyed Friend

    Play Episode Listen Later Feb 25, 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 progressed from prison to successful entrepreneur in 5 years. He does not condone or recommend any reckless behavior shared in these stories. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 11: Flat Tail Stories

    Play Episode Listen Later Feb 18, 2024 69:04


    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 and how he progressed from prison to successful entrepreneur in 5 years. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 10: This Is Where Stuff Gets Broke

    Play Episode Listen Later Feb 11, 2024 73:49


    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.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 9: You've Done A Lot of Work to That Thing

    Play Episode Listen Later Feb 4, 2024 82:18


    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 federal prison. Jesse will share stories from his reckless past and how he progressed from prison to successful entrepreneur in 5 years. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 8: Mom, It's a Party

    Play Episode Listen Later Jan 28, 2024 62:22


    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 from prison to successful entrepreneur in 5 years. https://www.mayexcavating.com/ Follow us on social media: TikTok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 7: The High Road to Success

    Play Episode Listen Later Jan 21, 2024 68:00


    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 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.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 6: Catch Me If You Can

    Play Episode Listen Later Jan 14, 2024 71:19


    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.mayexcavating.com/ Follow us on social media: Tiktok : Reckless Success (@reckless.success) | TikTok Instagram Coming Soon: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 5: Dirty Hands, Clean Money

    Play Episode Listen Later Jan 7, 2024 92:00


    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.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success Instagram Coming Soon: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 4: Hot for Teacher

    Play Episode Listen Later Dec 30, 2023 97:36


    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 entrepreneur in 5 years. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success YouTube: https://www.youtube.com/@Reckless.Success Instagram Coming Soon: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 3: Fleeing to Mexico

    Play Episode Listen Later Dec 30, 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. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success YouTube: https://www.youtube.com/@Reckless.Success Instagram Coming Soon: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 2: Fighting in a Small Town

    Play Episode Listen Later Dec 29, 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 in 5 years. https://www.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success YouTube: https://www.youtube.com/@Reckless.Success Instagram Coming Soon: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

    Episode 1: Police Raids

    Play Episode Listen Later Dec 29, 2023 61:09


    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.mayexcavating.com/ Follow us on social media: Tiktok : https://www.tiktok.com/@reckless.success YouTube: https://www.youtube.com/@Reckless.Success Instagram Coming Soon: @RecklessSuccess Intro song: Put Em in They Place by Matt Corman www.mattcorman.com

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