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Strawberry Letter

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Strawberry Letter
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  • Strawberry Letter

    Money Tips: He emphasizes discipline, leadership, risk-taking, and strategies for building generational wealth.

    2/15/2026 | 22 mins.
    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
    See omnystudio.com/listener for privacy information.
  • Strawberry Letter

    Brand Building: She creates AI Clones that can produce content without the owner being physically present.

    2/15/2026 | 31 mins.
    Two-time Emmy and Three-time NAACP Image Award-winning, television Executive Producer Rushion McDonald interviewed Brittany Benson.
    ***
    ### **Purpose of the Interview**
    The interview on *Money Making Conversations Masterclass* aimed to:
    * Showcase Brittany Benson’s journey as a **brand strategist**, **AI consultant**, and founder of **The Branding Bar**.
    * Educate entrepreneurs and small business owners on **branding**, **social media strategy**, and the **impact of AI** on marketing.
    * Inspire listeners to leverage technology and consistency to build authentic brands.
    ***
    ### **Key Takeaways**
    1. **Early Branding Journey**
    * Brittany unknowingly started building her brand in college through her TV show *On the Air with Brittany B*.
    * She leveraged early platforms like YouTube and Facebook before “social media” was a term.
    2. **Consistency is Key**
    * Success in branding comes from **consistent engagement**, even before monetization was possible.
    * Brittany grew her Instagram following to over 130,000 by focusing on consistency rather than chasing trends.
    3. **Influencer Myth**
    * Large follower counts don’t guarantee success; **engagement matters more than numbers**.
    * “If I have 2,500 followers who listen to me, that’s more powerful than 100,000 who don’t.”
    4. **Paid vs. Organic Growth**
    * Paid ads can help, but **organic growth builds trust**.
    * Best practice: build an organic base first, then use paid ads to amplify.
    5. **Pivot to AI**
    * Brittany pivoted from a traditional social media agency to **AI-driven branding solutions**.
    * She creates **AI twins** for business owners—digital replicas that can produce content without the owner being physically present.
    6. **Generative AI in Marketing**
    * AI tools can create graphics, videos, and even voice clones.
    * Brittany emphasizes AI as a **tool to enhance workflow**, not replace human creativity.
    7. **Consulting Approach**
    * Offers strategy calls to identify problems and recommend AI tools.
    * Services range from **strategy planning**, **consulting**, to **done-for-you solutions**.
    ***
    ### **Notable Quotes**
    * **On branding:**
    *“I was always building a brand, even when I didn’t realize I was building a brand.”*
    * **On engagement vs. followers:**
    *“If I have 2,500 followers who listen to me, that’s more powerful than 100,000 who don’t.”*
    * **On AI’s role:**
    *“AI is just a tool. It’s not going to replace your job—it still needs human direction.”*
    * **On staying ahead:**
    *“I’ve been told I have the gift of insight to see what’s coming, even if it’s not popular yet.”*
    * **On her pivot:**
    *“I started generating AI twins for business owners so they could show up online without showing up.”*
    ***
    #SHMS #STRAW #BEST
    See omnystudio.com/listener for privacy information.
  • Strawberry Letter

    Uplift: He was raised in poverty, now a real estate tycoon, top Lowe's contract and community leader.

    2/14/2026 | 29 mins.
    Two-time Emmy and Three-time NAACP Image Award-winning, television Executive Producer Rushion McDonald interviewed Michael Woodward.
    He is the founder of Woodward Property Group, and discusses his journey from poverty to entrepreneurship, his success in real estate, and his commitment to education.
    🔑 Key Themes & Highlights
    From Poverty to Business Success
    Grew up in Miami’s Liberty City, learning business skills from his grandmother, who ran a small candy shop in the projects.
    Used his experiences to build a career in real estate and education.

    Educational & Entrepreneurial Journey
    Founded Alpha Educational Consultants, a tutoring company that expanded into real estate consulting.
    Mentored students, led college tours, and helped individuals navigate property investments.

    Building Wealth Through Real Estate
    Purchased his first duplex at 20, living rent-free while tenants covered the mortgage.
    Continued acquiring properties, eventually amassing over $1 million in real estate assets.

    Woodward Property Group & Lowe’s Partnership
    Transitioned into property management and home improvement, securing a contract with Lowe’s to renovate high-end kitchens.
    Expanded his business to manage multiple Lowe’s locations across Atlanta.

    Lessons in Business & Financial Growth
    Emphasized the importance of credit management and strategic investments.
    Encouraged aspiring entrepreneurs to take calculated risks and seek mentorship.

    📘 About Michael Woodward
    Michael Woodward is a real estate investor, educator, and entrepreneur based in Atlanta. Through Woodward Property Group, he provides property management and home improvement services, while continuing his mission to mentor and uplift communities through education and financial literacy.
    #AMI
    #STRAW
    #BEST
    #SHMS
    See omnystudio.com/listener for privacy information.
  • Strawberry Letter

    Money Tips: He issues a call to action to explore opportunities like Amazon DSP, construction and real estate investment.

    2/14/2026 | 22 mins.
    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 #BEST
    See omnystudio.com/listener for privacy information.
  • Strawberry Letter

    Uplift: He oversees operations and financial strategy for Rolling Stone, Billboard, Variety, The Hollywood Reporter, Vibe, SXSW

    2/14/2026 | 23 mins.
    Two-time Emmy and Three-time NAACP Image Award-winning, television Executive Producer Rushion McDonald interviewed Paul Rainey.
    He holds a powerful executive role in the media world, shaping the future of iconic brands like Billboard, Rolling Stone, and SXSW.
    🏆 Paul Rainey’s Executive Career at Penske Media Corporation (PMC)
    Current Role
    Executive Vice President of Operations and Finance at Penske Media Corporation (PMC).
    Oversees operations and financial strategy for Rolling Stone, Billboard, Variety, The Hollywood Reporter, Vibe, SXSW, and more.
    Provides strategic input across PMC’s global media brands and live events, including the Billboard Music Awards, SXSW, and American Music Awards.
    Key Responsibilities
    Leads financial decision-making, acquisitions, and operational procedures across PMC’s portfolio.
    Serves on several boards, including as Audit Committee Chair of Redaptive, Inc. and a Director at SXSW.
    Background & Education
    Holds a Master of Science in Accountancy and a BBA in Finance and Computer Applications from the University of Notre Dame.
    Formerly held leadership roles at General Electric, Global Eagle, and Harris CapRock Communications, managing billion-dollar operations across five continents.
    📘 About PMC & Cultural Influence
    PMC is a global media powerhouse, reaching over 350 million people monthly. Its brands shape culture through journalism, entertainment, and live events, including SXSW
    Paul Rainey is a rare blend of creative storyteller and corporate strategist, bridging the worlds of graphic novels and global media leadership. Whether he’s crafting a sci-fi twist in a comic or guiding the future of Billboard and SXSW, his influence is both wide-reaching and deeply personal. Let me know if you’d like a visual timeline of his career or a deeper dive into one of his roles. 🎬📈✨

    #STRAW
    #BEST
    #SHMS
    See omnystudio.com/listener for privacy information.

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About Strawberry Letter

Got a situation? Steve Harvey and Shirley Strawberry deliver unfiltered advice on love, relationships, family, work, and life. Send your letter, subscribe, and get real talk every day! Every weekday, the Steve Harvey Morning Show tackle a listener-submitted “Strawberry Letter”... a real-life dilemma ranging from romantic entanglements to career choices, family drama to money struggles, and everything in between. With a blend of wisdom, wit, and brutal honesty, they offer candid commentary and heartfelt guidance, often sparking conversation (and laughter) among the rest of the morning show crew. Submit your Strawberry Letter at www.steveharveyfm.com for a chance to be featured, and get the truth, Steve Harvey style!
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