🎙️ Episode 12: From Rock Bottom to the Open Road — How My CDL Changed Everything

In Episode 12 of The Welcome Legacy Podcast, I pick up where Episode 11 left off and break down what rebuilding my life actually looked like in real time.

After leaving my old environment, my family and I moved to Kissimmee in early 2019. During that season, I was searching for legal paths forward—joining a LegalShield marketing team, attending meetings, and even creating an online course called How to Fail Forward, teaching how to use failure as fuel while I was still living it.

By October, I was already in communication with CareerSource and had started trucking school. In the middle of the process, my family moved, housing became unstable, and during my final week of CDL school in Dundee, we were told we had to leave due to having too many people in the home—11 total.

I talk about attending TDI Trucking School in Sanford, staying in a hotel Monday through Thursday for three weeks, driving home on weekends, and finishing strong even after my wife and kids moved more than 100 miles away to Newberry.

This episode covers getting my CDL, landing my first trucking job with J&R Schugel, life on the road, studying real estate while trucking, buying my first home in 2021, and earning my Realtor license in 2022.

This is a story about discipline, sacrifice, and using a legal skill as a bridge to stability and ownership.

If you’re under pressure, rebuilding your life, or trying to do things the right way for your family—this episode is for you.

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I Was Addicted, License Suspended, and Stuck — How Discipline Led Me to My CDL

In this episode of The Welcome Legacy Podcast, I tell the truth about a season of my life when everything felt lost.

I open up about battling addiction, dealing drugs, getting a DUI, and losing my driver’s license for five years. I talk about the role my grandmother played in my upbringing, the pressure of fatherhood, and the moment I realized I couldn’t keep repeating the same mistakes.

This episode is about being stuck—and choosing discipline anyway.

I share how my cousin pushed me toward getting my CDL, how I went on the road with him, studied, came back, and took the test. That decision became the turning point that helped me start rebuilding my life the right way.

If you’re struggling, feeling trapped by your past, or trying to find a legal way forward, this episode is for you. Discipline doesn’t change everything overnight—but it opens the door.

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📝 Spotify Episode Description

From Life Sentence to Legacy: The Jesse Crossman Story | The Welcome Legacy Podcast (Ep. 11)

At just 18 years old, Jesse Crossman was sentenced to 32 years with more than 100 years suspended. He went on to serve 19 years behind bars. Instead of allowing prison to break him, Jesse discovered faith, discipline, and resilience that would ultimately transform his life.

In this episode of The Welcome Legacy Podcast, Jesse shares his journey from the pain of incarceration to his release, the struggles of reentry, and his mission today. From launching his nonprofit Second Chancer Foundation to writing his upcoming book, Jesse’s story is about redemption, second chances, and building a legacy beyond the past.

🎧 Listen & Watch Everywhere

• Spotify → The Welcome Legacy Podcast

• Apple Podcasts → The Welcome Legacy Podcast

• YouTube → The Welcome Legacy Podcast

📚 Books by James G. Welcome
• Boy 2 Man → https://a.co/d/4EZ7kRj
• Cardin’s Big Idea → Link
• Lyla’s First Piggy Bank → Link

🎓 Free Course – How to Fail Forward
https://www.udemy.com/course/how-to-fail-forward/?referralCode=1786286125581977C5FD

🎶 Music by James G. Welcome
https://open.spotify.com/album/1sciuSepcoqFBXMc03Cmyh?si=-nG4AtO8QVS0rRfYLqdSNw

🕢 New episodes drop every Wednesday at 7:30 PM EST.

© Welcome Legacy Publishing

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