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Reckless Success

Reckless Success

Written by: Jesse May
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About this listen

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 Economics Leadership Management & Leadership
Episodes
  • Episode 38: I Can Go Dark Real Quick
    Jul 25 2025

    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

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    52 mins
  • Episode 37: Marlboro Man
    Feb 9 2025

    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

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    2 hrs and 19 mins
  • Episode 36: Hot Rod
    Nov 24 2024

    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

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    35 mins
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