Reckless Success

Jesse May
  • 5.0 (7)
  • Entrepreneurship
  • Updated Weekly

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.

  1. 07/25/2025

    Episode 38: I Can Go Dark Real Quick

    Jesse and Lesa talk about their Chevy Duramax being stolen off the jobsite, karma, Jesse's El Camino driving babysitter, and excavation life after taking a small hiatus. 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

    52 min

  2. 02/09/2025

    Episode 37: Marlboro Man

    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

    2h 19m

  3. 11/24/2024

    Episode 36: Hot Rod

    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

    35 min

  4. 11/10/2024

    Episode 35: Chapel Isn't a Safe Place

    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

    1h 9m

  5. 10/13/2024

    Episode 34: Everybody Loves Watermelon

    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

    32 min

  6. 09/29/2024

    Episode 33: Chemical Romance

    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

    1h 1m

  7. 09/15/2024

    Episode 32: Tow Truck Chronicles

    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

    1h 1m

  8. 09/01/2024

    Episode 31: Get Your Mind Right

    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

    1h 15m
See All (38)

Ratings & Reviews

5
out of 5
7 Ratings

About

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.

Information

  • Creator
    Jesse May
  • Years Active
    2023 - 2025
  • Episodes
    38
  • Rating
    Explicit
  • Copyright
    © Jesse May
  • Show Website
    Reckless Success