#112 – After 13 Yrs In Prison, Trucking Entrepreneur ONLY Hire’s Ex-Felons

Early Life:

When describing Keidrian Brewster, aka “Bossman” Brewster, how to start a trucking business we could refer to him as an entrepreneur, fleet owner, author, and motivational speaker. At the age of 17, he was sentenced to 13 years and nine months in prison by the Texas Department of Criminal Justice. At the age of 32, he finally got out. Brewster lost his family during his imprisonment. His mother died from a drug overdose, and his younger brother was killed. He said that it was life-changing for him. Upon his release from prison, he worked in a warehouse for a while as he tried to adjust to society; however, he disliked it.

Brewster was exposed to trucking through one of his homeboys. How to start a trucking business he thinks it’s crazy because his wife used to come and tell him about trucking when he was in prison. His partner had pulled off the perfect trucking job, which inspired Brewster to take it seriously as a career choice. He soon obtained his commercial driver’s license (CDL) and began pursuing a career in trucking.

Brewster started his trucking career driving a semi-truck. After driving a semi-truck for a company called U.S Art for a year, he got himself a Dooley truck, 40-foot gooseneck trailer, and two-three hotshots. He is now the owner of Brewster Logistics, a company that employs only formerly incarcerated individuals and gives them the opportunity to lead productive lives.

Interaction With TN’H:

Brewster is an exemplary role model for other formerly incarcerated individuals; his passion for helping others attain the same level of success that he has had is truly admirable. In his interactions with TN’H, he covered all the details necessary for them to begin their trucking careers. He contends that the biggest key to success in the trucking industry is dealing with day-to-day operations.

The primary source of income for Brewster’s hotshot operation is from containers he has contracted with. He explained how the operation works and gave the audience some insights into how to find loads for hotshots. For loading these types of containers, one requires a Tilt Bed Trailer. Brewster explained the difference between a regular Tilt Bed Trailer and a regular flatbed trailer. He also expresses his views on how the business has changed over time, and he feels that consistency is vital in order to grow a company.

For those interested in a container business like his, Brewster offered some beneficial advice to entrepreneurs looking to start one. The best thing, he said, is to research online. Brewster started his business with Hotshots and transits to semi-trucks. In the interview, he revealed why the transition was right for him and how he knew when it was time. He also explains how he mastered the art of getting comfortable with this transition. To top it all off, Brewster offers some helpful hints for those who are thinking about scaling a semi.


Final thought:

After an hour-long interview, Brewster ended with a piece of advice: ‘Invest in yourself.’  He emphasized that we must invest in ourselves and our brands in order to succeed.

To know more about Brewster Logistics, Please view the Video Below


Episode Timeline

[skipto time=1:43]1:43 – Early life. [/skipto]

[skipto time=5:43] 5:43 – Why semi-truck.[/skipto]

[skipto time=17:13]17:13 – how to find the container business. [/skipto]

[skipto time=22:12]22:12- The story of transition. [/skipto]

[skipto time=34:42]34:42- Prison reform . [/skipto]


About The Host

rahmel - how to start a trucking company

Rahmel Wattley

The creator & host of Truck N’ Hustle, is a renowned personality in the trucking & logistics industry who hosts podcasts with the reputed & successful trucking entrepreneurs to share the knowledge required to start & sustain the logistics business!

how to start a trucking business

Keidrain Brewster

Keidrain Brewster is, without doubt, the undisputed new “face of prison reform”. Not only does Keidrain inspire people daily with his vlogs in and outside of the jail, he has also created a re-entry pipeline for formerly incarcerated individuals to have a career path in trucking once they return to society.

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