Financial Tip: We discuss his mission as a financial leader and his focus on expanding diversity in the financial services industry.

Two-time Emmy and Three-time NAACP Image Award-winning, television Executive Producer Rushion McDonald interviewed Brett Chestnut.

Summary of the Interview

On Money Making Conversations Masterclass, host Rushion McDonald interviews Brett Chestnut, Managing Director of Northwestern Mutual Goodwin, Wright Gwinnett. The conversation centers on Brett’s mission as a financial leader, his journey from engineering to financial planning, his commitment to mentoring, and his focus on expanding diversity in the financial services industry.

Brett describes how he transitioned from engineering in 2015 to financial planning because he wanted to help people regain the ability to dream—not just survive. He discusses his work in recruiting diverse advisors, supporting career‑shifting professionals, mentoring, and educating people on foundational financial decision‑making.

The interview also explores money mindsets, budgeting, the challenges of building wealth in communities of color, and the often‑overlooked emotional side of money. Brett emphasizes starting with the basics, not skipping steps (e.g., jumping straight to cryptocurrency), and building strong financial foundations.

Rushion repeatedly highlights Brett as a powerful brand and role model, underscoring the importance of Black leadership in financial fields and the role of representation in increasing trust and access.

Purpose of the Interview

The interview’s purpose is to:

1. Introduce Brett Chestnut as a trusted financial leader

Rushion aims to elevate Brett’s visibility as a Black managing director in financial services—an industry where representation has traditionally been limited.

2. Educate listeners on financial empowerment

Brett provides practical, relatable guidance on budgeting, investing, career transitions, and developing financial discipline.

3. Highlight Northwestern Mutual’s diversity initiatives

Brett explains how the company is intentionally investing in diverse advisors and underserved markets.

4. Inspire career‑based and financial self‑reflection

He encourages people to examine their spending habits, consider new career paths, and align decisions with long-term goals.

5. Promote mentorship and community uplift

Both Brett and Rushion stress the transformative power of mentorship and generational investment.

Key Takeaways

1. Financial empowerment starts with awareness

Brett urges everyone to analyze their last 2–3 months of spending to understand what their habits really prioritize.

2. You must “choose your hard”

Saving and planning may be difficult now, but the alternative is harder later. Financial success requires discipline, not magic formulas.

3. Wealth building is emotional as much as logical

Money connects to family, relationships, self‑worth, stress, and confidence. Advisors must understand clients emotionally, not just mathematically—especially women and diverse communities.

4. Don’t skip steps (especially with investing and crypto)

Many want to “get rich fast,” but Brett warns that skipping foundational steps (budgeting, savings, retirement planning) leads to confusion and poor decisions.

5. Mentorship works only with real relationship

True mentorship requires understanding someone’s full life story, not just giving advice.

6. Representation matters in financial services

Northwestern Mutual is investing heavily in diverse advisors not just for optics, but because entire markets have been historically underserved.

7. Closing the wealth gap requires generational strategy

One generation must be willing to be selfless, disciplined, and intentional with assets to move future generations forward.

8. Brett sees his work as multiplying impact

By developing new advisors and helping create “15 millionaires,” he hopes to create compounding community uplift.

Notable Quotes (from the transcript)

On financial empowerment

“I want people to dream again. We’re not dreaming no more—we’re living because of obligation.”
“When we’re born we look like our parents, but when we die, we look like our decisions.”

On career purpose

“I help people who are successful but career‑disturbed. They want more.”

On money habits

“Look at your last three months of spending. Your money tells you what your real priorities are.”

On investing and crypto

“People want to skip steps… going from no savings straight to crypto.”
“If you don’t understand it, maybe it’s not time for you to invest in it.”

On mentorship

“To give someone feedback without relationship is harassment.”
“Let me hear your story… mentorship starts with knowing the inner person.”

On diversity and empowerment

“Their growth strategy is diversity… whole markets haven’t even been called on yet.”

On community and identity

“We’re special… if we regain that confidence and approach the marketplace with courage, everything changes.”

On wealth-building reality

“You have to choose your hard. Hard now or hard later.”

#SHMS #STRAW #BEST

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Two-time Emmy and Three-time NAACP Image Award-winning, television Executive Producer Rushion McDonald interviewed Dr. Justin M. Lee. Purpose of the Interview To showcase Dr. Lee’s journey from a young real estate agent to a multi-industry entrepreneur. To inspire listeners with strategies for wealth-building through real estate, construction, and logistics. To encourage financial literacy, ownership, and collaboration within underserved communities. To issue a call to action for minorities to explore opportunities like Amazon DSP and real estate investment. Key Takeaways Early Career & Education Started young in real estate, embraced discomfort in rooms dominated by older professionals. Leveraged millennial tech skills (social media marketing) to help veteran brokers grow. Earned a doctorate degree and became a licensed real estate broker. Social Media as a Business Tool Built a strong presence on TikTok (90K followers) and other platforms. Helped older real estate firms thrive by creating digital visibility. Emphasized that “business must look as good online as in person.” Financial Literacy & Homeownership African-American communities often lack foundational financial knowledge. Key barriers: misunderstanding credit, fear of debt, and lack of exposure to ownership benefits. Advocates teaching the difference between good debt (real estate) and bad debt (consumer credit). Real Estate Process Initial onboarding: credit score, income, tax filing. Connect clients with lenders, secure pre-approval, then negotiate and close within 30–45 days. Uses property tours as motivation even for those not yet approved. Pooling Resources for Wealth Industry dominated by white men and foreign investors who use syndication. Dr. Lee created a private family fund with fraternity brothers and friends. Acquired 150+ apartment units and commercial properties by pooling resources and forming LLCs. Amazon DSP Opportunity Owns an Amazon Delivery Service Partner business (42 trucks, 200 employees). Offers minorities a chance to apply for DSP with $10K grant. Taught him true CEO skills: HR, payroll, compliance, and scaling operations. Construction Business Entered construction after experiencing exploitation in fix-and-flip projects. Learned the business side (permits, change orders) and got licensed. Built major projects like a 10,000 sq. ft. restaurant in Atlanta. Advocates for Black representation in construction, an industry dominated by whites and Hispanics. Personal Background Raised in New Orleans during Katrina by a single mother and grandparents. Mother invested FEMA checks into real estate, teaching him property management and renovation skills early. Believes knowledge is power and emphasizes planning and consistency. Notable Quotes On embracing discomfort:“I learned to embrace the uncomfort and make it one of my biggest strengths.” On social media:“You have to make your business look the same way online as in person.” On financial literacy:“Real estate is always going to be good debt. Bad debt is the Macy’s card.” On collaboration:“Pooling resources shows how far we can go and how fast we can go—but together.” On planning:“If you don’t plan, you plan to fail. All you have to do is stick to the plan.” #SHMS #STRAW #BESTSupport the show: https://www.steveharveyfm.com/See omnystudio.com/listener for privacy information.

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