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Strawberry Letter

Overcoming the Odds: Motivational journey from rural America to corporate success and owning multiple Jersey Mike’s Franchises.

Strawberry Letter

iHeartPodcasts

Society & Culture, Relationships

4.51.7K Ratings

🗓️ 19 February 2026

⏱️ 23 minutes

🧾️ Download transcript

Summary

Listen and subscribe to Money Making Conversations on iHeartRadioApple PodcastsSpotify, www.moneymakingconversations.com/subscribe/ or wherever you listen to podcasts. New Money Making Conversations episodes drop daily.  I want to alert you, so you don’t miss out on expert analysis and insider perspectives from my guests who provide tips that can help you uplift the community, improve your financial planning, motivation, or advice on how to be a successful entrepreneur.  Keep winning!

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

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. Franchising Journey

    • Relationships opened doors to Jersey Mike’s franchise ownership.
    • Entrepreneurship requires hands-on involvement—Keith still works in his stores when needed.
  6. 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.

Transcript

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0:00.0

This is an IHeart podcast.

0:02.6

Guaranteed Human.

0:04.3

Welcome to my show.

0:05.6

I'm Rishon McDonnell, the host of Money Making Conversations Masterclass, where we encourage

0:09.8

people to stop reading other people's success stories and start planning your own.

0:14.1

Now, you don't want to miss an episode, so please take a moment right now to follow or

0:18.2

subscribe to Money Making Conversations Masterclass.

0:21.4

It's free.

0:27.0

You can follow me on IHeartRadio app, Spotify, Apple Podcasts, or wherever you listen to your podcast. New Money Making Conversation Masterclass episodes drop daily. I want to keep you on alert

0:32.9

because my guests provide tips on how you can uplift your community, improve your

0:37.0

financial planning, motivation, or advice on how to be a successful entrepreneur.

0:42.2

Now, let's get this podcast started.

0:43.9

My guest left corporate America and is the co-founder and president of Coaching Catalyst, LLC,

0:50.2

a boutique executive coaching and business advisory firm and co-founder and president of social capital LLC,

0:58.6

which owns and operates multiple Jersey mic franchises in the Metro Atlanta area.

1:04.9

Please welcome to Moneymaking Conversations Masterclass Keith Mildner.

1:09.7

How you doing, Keith?

1:12.7

I am terrific, sir. I hope you are as well. Tell us about your background before we get into the journey of being a person

1:17.0

in the corporate world and then leaving the corporate world to believe in yourself and be an

1:21.4

entrepreneur. Let's start at the beginning. Sure. I was born and raised in a small farming

1:27.3

community in North Carolina, Reedesville, North Carolina.

1:31.1

Both my parents were farmers. My dad was a second or third generation sharecropper,

...

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