Strawberry Letter

Two-time Emmy and Three-time NAACP Image Award-winning, television Executive Producer Rushion McDonald interviewed Dr. Isaiah Tatum.
A 24-year-old entrepreneur, touring artist, and hotel owner:
🎯 Purpose of the Interview
The interview showcases Dr. Isaiah Tatum’s extraordinary journey from homelessness to becoming a venture capitalist, hotel developer, and touring saxophonist. It aims to inspire young entrepreneurs by highlighting the importance of faith, planning, mentorship, and financial literacy.
🔑 Key Takeaways 1. Early Passion for Music
Began playing saxophone at age 10.
Influenced by legends like Kenny G, Curtis Mayfield, and Aretha Franklin.
Practiced obsessively, leading to proficiency and touring opportunities.
Maintains a strong connection to music despite business ventures.
“I couldn’t wait to get home and play… I practiced six hours a day.” — Isaiah Tatum
2. Entrepreneurial Drive & Financial Literacy
Overcame homelessness and used that experience to fuel ambition.
Became an equity investor in Jazz Pharmaceuticals at 18.
Invested in real estate and hotel development with a focus on recession-proof models.
“I didn’t want to be an artist who had to stay on tour to maintain. I wanted to be financially free.” — Isaiah Tatum
3. Hotel Ownership & Strategy
Owns two Candlewood Suites and an Embassy Suites in Georgia.
Focuses on extended-stay models for consistent revenue.
Emphasizes customer experience and operational efficiency.
“Even if they’re spending $160, make them feel like they’re spending $1 million.” — Isaiah Tatum
4. Mentorship & Education
Studied finance and earned credentials from Wall Street Prep.
Values mentorship from icons like Kenny G and Keith Worsham.
Now mentors others and encourages financial literacy and self-confidence.
“Don’t look for who you are to fit in with everybody else… Elevate yourself.” — Isaiah Tatum
5. Vision & Future Endeavors
Developing new properties in Tupelo, MS and Nashville, TN.
Planning a Sweat Hotel concept and returning to music with a new album and tour.
Driven by a daily mindset of growth and execution.
“Even though I’ve done really good, it’s about what I’m doing tomorrow.” — Isaiah Tatum
📌 Notable Quotes
“Faith and a plan. A lot of people jump out there on faith. You better have a plan in your back pocket.” — Rushion McDonald
“I fell in love with credentials… I wanted to maximize every opportunity.” — Isaiah Tatum
“Let your results speak for themselves.” — Isaiah Tatum
#SHMS #STRAW #BEST
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Two-time Emmy and Three-time NAACP Image Award-winning, television Executive Producer Rushion McDonald interviewed Keith Milner.
Purpose of the Interview
The interview aims to inspire aspiring entrepreneurs by sharing Keith Milner’s journey from corporate America to entrepreneurship. It emphasizes discipline, leadership, risk-taking, and strategies for building generational wealth, particularly for underrepresented communities.
Key Takeaways
Foundational Lessons from Childhood
Growing up in a disciplined, hardworking family taught Keith accountability, integrity, and the principle of choices and consequences.
Education was highly valued in his household, shaping his drive for success.

Corporate vs. Entrepreneurial Mindset
Corporate careers can feel secure but are often riskier because you lack control over your destiny.
Entrepreneurship offers greater control and potential for generational wealth.

Leadership and Teamwork
Lessons from sports—teamwork, discipline, and leadership—translate directly into business success.
Establishing a common goal and coaching employees is crucial, but underperformers must eventually be let go.

Risk and Value
Many African-Americans view entrepreneurship as risky, but Keith argues it’s less risky than employment in an at-will state.
Success depends on creating value that customers are willing to pay for.

Franchising Journey
Relationships opened doors to Jersey Mike’s franchise ownership.
Entrepreneurship requires hands-on involvement—Keith still works in his stores when needed.

Advice for Aspiring Entrepreneurs
Adopt a growth mindset and positive attitude.
Follow the Five P’s: Plan, Prepare, Produce, Pivot, Persevere.
Understand that entrepreneurship is a daily grind—“Every morning in the jungle, the lion wakes up running.”

Notable Quotes
On discipline and accountability:
“If you said you were going to do something, you did it. If you were told to do something, you got it done.”

On choices:
“We make choices every day, and if you don’t make the right choice, there are consequences.”

On entrepreneurship vs. employment:
“Entrepreneurship and small business ownership is the best way to create generational wealth.”

On leadership:
“There are very few things in life you can do alone. You need people, you need a team.”

On success formula:
“You control the inputs, and therefore you can charge what you want—as long as you generate enough value.”

On entrepreneurial mindset:
“Plan, Prepare, Produce, Pivot, Persevere.”

Swahili proverb:
“Every morning in the jungle, the lion wakes up running… The question becomes, who’s going to run the fastest?”

#SHMS #STRAW #BEST
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The Strawberry Letter heard on The Steve Harvey Morning Show Monday, February 3rd, 2026. Subject: "He Left Me Out To Freeze"
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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 Alicia Lyttle.
SUMMARY OF THE ALICIA LYTTLE INTERVIEW
From “Money Making Conversations Master Class” with Rushion McDonald [
1. Purpose of the Interview
The purpose of this interview was to:
Showcase Alicia Lyttle, CEO and co‑founder of Air Innovations, known widely as the “Queen of AI.” [
Educate small business owners, entrepreneurs, and nonprofits on how to leverage AI for growth.
Highlight her mission to empower the African American community to not only keep up with AI—but lead in it. [
Demonstrate how AI tools can transform operations, content creation, finances, and productivity in minutes instead of months.
Inspire listeners through her entrepreneurial journey, professional pivots, and personal resilience.
2. High-Level Summary
Alicia Lyttle returns to the show two years after her last appearance, now positioned at the forefront of the global AI movement. She explains how her work has shifted from annual summits to monthly AI Business Summits, teaching tens of thousands of entrepreneurs how to use AI hands‑on for content, marketing, operations, and scaling.
She breaks down how simple tools—such as NotebookLM, ChatGPT, Jasper, Gemini, and HeyGen—can turn a single piece of content into newsletters, PowerPoints, videos, study guides, and more. She stresses that AI is now accessible, especially with free versions like ChatGPT.
Alicia also shares her origin story in AI, beginning with a 15‑year‑old speaker at Walmart Tech Live describing IBM Watson. This sparked her fascination and ultimately led her to pivot her entire company toward full-time AI training and consulting by 2022—despite skepticism from her peers.
She details the massive growth of her brand, including 21,000+ live summit attendees and explosive social media expansion. The interview also addresses AI’s role in finance, healthcare, government, job disruption, and how individuals can future‑proof themselves.
Her personal story of overcoming a restrictive ex-husband who told her she would “never speak again” underscores her powerful message: no one should silence your gifts. Now she speaks to thousands, leads major events, and helps others build new careers in AI.
3. Key Takeaways A. AI Is Evolving Fast—and So Must We
AI is changing so quickly that entrepreneurs cannot afford to wait for annual updates. This is why Alicia shifted to monthly training summits. People need ongoing education to stay competitive.
B. Hands‑On AI Education Is the Key
Alicia doesn’t just lecture—she walks participants through real demonstrations:
Uploading YouTube links
Creating summaries
Generating emails, mind maps, PowerPoints, quizzes, videos, and more
…all from a single input.
Her approach eliminates fear and teaches entrepreneurs how to use AI immediately.
C. Accessibility Has Changed the Game
The release of ChatGPT, especially the free version, democratized AI. Before that, tools like IBM Watson were too complex and expensive. Now anyone with a laptop and internet connection can build websites, write content, or automate business flows in minutes. [
D. The African American Community Must Lead—Not Follow
Alicia emphasizes that historically, Black communities have been “last in line” in tech innovation, but this AI era presents a once‑in‑a‑generation opportunity to jump ahead.
She sees it as her mission to speak everywhere Black entrepreneurs are to ensure they seize this moment.
E. AI Will Replace Tasks—But People Can Future‑Proof Themselves
Jobs are already shifting. Companies are laying off non–AI‑literate employees.
Alicia urges people to:
Become AI‑fluent
Join AI committees at work
Pursue certification
Use AI to become their company’s internal expert
“There’s no maybe—you have to learn AI,” she warns.
F. AI is Transforming Every Sector: Finance, Healthcare, Government
She provides insights on…
AI receptionists (“Monica” and “Leslie”) that boost customer interaction to 92%
Financial analysis using secure ChatGPT setups
AI mental health companions
Government calls for national AI leadership
G. Alicia Monetizes Through Education, Certification & Consulting
Her business model includes:
Free monthly summits
Paid masterclasses
Corporate consulting
AI certifications
Live Atlanta workshops
She teaches others to become AI consultants too.
H. Her Personal Triumph Story Inspires Thousands
A powerful moment is when she recounts her ex-husband saying:
“There’s only one quarterback on a team—and you will never speak again.”
Yet today, 1,200+ people attend her live events, and tens of thousands join her virtual trainings.
Her success proves resilience and purpose overcome adversity.
4. Key Quotes On AI Opportunity
“Never has there been a better time in history to start, build, or scale a business than right now.”
On Training Entrepreneurs
“Open your laptops… use the same prompt I use. See what results you get.”
On the Power of AI Tools
“You can take one episode and repurpose it into all these different content ways.”
On Pivoting Her Entire Company
“In 2022, I said we’re closing this business and going all in on AI.”
On Being Black in Tech
“My mission is to make sure our community is not left behind—but ahead of the curve.”
On Personal Resilience
“You will be speaking on the best stages… people will come to see you.”
(A friend’s response after she was told she’d “never speak again.”)
On Future-Proofing Careers
“Those using AI will replace you. You have to learn how to leverage AI.”
On AI as a Human-First Technology
“AI plus human intelligence—that’s what takes things to the next level.”
#SHMS #STRAW #BEST
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