Real Stories Ep 32: Derek – Redirecting His Energy to A Better Life

  • October 15, 2022
  • By: Greenpath Financial Wellness
  • GreenPath Financial Wellness is a trusted national nonprofit with more than 60-years of helping people build financial health and resiliency. Our NFCC-certified counselors give you options to manage credit card debt, student loans and homeownership.

A native of Chicago, Derek runs several small businesses. For him, success is not just measured by his financial success, but by the opportunities he creates for others in his community. Derek’s money story is as real as it gets. He has taken the lessons from his past life to fuel his personal growth. His wisdom reaches beyond money.

Our conversation is a roundtable interview with our co-hosts, Omari and Shamica and special guest, Mick Dumke. A reporter for ProPublica, Mick had originally interviewed Derek for a piece he wrote in 2013 which details how the drug trade in Chicago was run like a Fortune 500 company.

A Letter from the United States Bureau of Prisons

The path to financial freedom is hard, and GreenPath is so proud to be part of Derek’s journey. You can read Derek’s full letter here.

Key Moments

4:36 Derek describes how multiple businesses and jobs help him work towards his financial goals.

8:21 He shares how he has redirected his energy to do what it takes to find success hustling.

15:24 Derek reflects back on how his childhood experiences influenced the decisions he made.

18:47 He discusses how and why his mindset shifted, both in terms of how he invested in himself and his community.

25:29 Derek starts a financial education program for incarcerated individuals.

27:28 Listen to Derek’s first letter to GreenPath from prison.

30:32 GreenPath’s materials are a springboard for Derek to create a customized curriculum for a re-entry program.

35:05 Upon his release, Derek finds a creative way to make money.

39:59 Derek describes how people reacted to his new mindset.

43:18 He describes how a personal tragedy led to his first getting involved in his business ventures.

46:34 Derek shares his wisdom about having a long-term mindset when it comes to your financial goals.

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Music by Hir-O

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Greenpath Financial Wellness

GreenPath Financial Wellness is a trusted national nonprofit with more than 60-years of helping people build financial health and resiliency. Our NFCC-certified counselors give you options to manage credit card debt, student loans and homeownership.


GreenPath is a non-profit credit counseling organization. GreenPath’s goal is to offer guidance and support to individuals seeking to manage and overcome financial challenges through education, financial counseling and debt management programs. The information provided is for educational purposes only. Consulting with a licensed financial advisor and tax advisor is recommended before making any major financial decisions. GreenPath is not a debt settlement company, credit repair company, credit repair service, nor does GreenPath provide debt consolidation loans. By using this website, you acknowledge and agree that GreenPath is not responsible for any financial decisions you make based on the information provided on this site.