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Episode 55: Taking a second look at Oprah

What we can learn from Oprah Winfrey
Episode 55: Taking a second look at Oprah


This “Money With Mak and G” podcast episode, I go over the lessons we can learn from Oprah Winfrey’s legacy, the struggles she went through, and her qualities that led her to success.


Oprah Winfrey is an inspirational billionaire, not only did she come from a poor background with limited opportunity but she’s also done a great deal of good with her wealth.


This episode, I look at the struggles Oprah went through in her life before she became successful, the qualities she had that enabled her success, and what we can learn from the legacy she left behind…


“Oprah had talents anyone could possess.” Ben Jones

Time Stamps:

00:20 – What America was like in the 60s.

00:57 – Why I wanted to travel when I was younger.

01:25 – How C J Walker helped the black community.

02:12 – The struggles Oprah went through when she was younger.

03:00 – Oprah’s qualities that made her successful.

04:00 – The importance of persistence and grit.


Connect with Ben Jones:



BEN: I’m not sure why Oprah really hit me. When I started research on this last episode, I think my feelings were part realization of all the good she has done, how I missed a lot of it being outside the country, and the real hardships in her life that she had to overcome.

As someone born in the late 60s, there was a lot going on in this country at the time. But Oprah was a teenager in the late 60s, the Vietnam War was raging. The Civil Rights Act of 1964, led to desegregation, the ending of Jim Crow laws in 1965. And then the turmoil that followed these events, I wasn’t even born yet for most of it. And when younger, I wasn’t even aware of any of these massive changes in the fabric of our country, but she was faced with it daily.

I was born and raised in Indianapolis, and a big part of my desire to travel was to expose myself to more of the world than Indiana alone. And what I saw around me, I guess I should have opened my eyes a bit more at home. I definitely noticed the madame Walker theater growing up. It was downtown near the Indiana Purdue campus in Indianapolis. But it took until this moment to ask myself who she was or what she did. Talk about an absolutely unbelievable story. I can’t even imagine the thought of my older siblings being born into slavery and I wasn’t. That goes beyond mind boggling. It’s been three days since I learned that fact and I still can’t stop thinking about it.

Both CJ Walker and Oprah did things that were first in their time, CJ Walker helped 1000s of black people through jobs that she created that weren’t available to them at the time. She was the first female black millionaire. Sometimes we see money as being evil, but she provided jobs and a product that was needed and helped 1000s more. I didn’t know this, but heavy dandruff and scalp infections were commonplace in the black community at the time. And having a product that helped with that must have felt pretty good. Because she helped so many. Oprah has never hidden the fact that she was abused in several ways when growing up. She ran away at 13 and was pregnant at 14 But her baby was born prematurely and passed away.

I have thought many times about what my life would have been like if my parents didn’t demand that I get educated and give me the support to succeed. Oprah clearly didn’t have the support she needed during many points in her life. She credits her fourth grade teacher and grandmother for a lot of the support she received during her life, which is great to hear. But her life was not easy. It’s literally hard to comprehend how she could have gotten through her early years, let alone grown to such a success. With so many hurdles that were in front of her. Yes, she had something special. But when we think of attributes that make people billionaires, they don’t always have to be magical.

Oprah had talents that anyone could possess. She wasn’t a prodigy or born with some rare physical talent, but she was someone who had her share of issues. She had weight problem scars from childhood and she let people treat her poorly early in her career, but she chose to be kind, caring for others, treat people with respect and be a force of good. It makes me think of the quote by Calvin Coolidge. Nothing in the world can take the place of persistence. Talent will not. Nothing is more common than an unsuccessful person with talent. Genius will not unrewarded genius is almost a proverb. Education will not, the world is full of educated derelicts. Persistence and determination alone are omnipotent. The slogan press on has solved and always will solve the problems of the human race. People with talent can be found everywhere. But persistence and determination is sometimes more rare. But it’s available to us all.

Research from Angela Duckworth focuses on grit, which is a very close cousin to persistence. You have to believe in yourself and persist with grit. That’s why the internal messaging you provide yourself is so critically important. Oprah came from nowhere from nothing with very little inner corner. She got pushed around, abused, knocked down and decided to go ahead and get up anyway. She spoke to the heart of America and looked at what she did.

She received over 20 million fan letters and over 25,000 emails each week. She interviewed over 28,000 guests, including five presidents. She had an audience somewhere between 30 and 50 million people each week. She’s donated over $400 million, mostly to education. And she gave away around $24 million worth of giveaways on her show. I think you’d be hard pressed to find anyone during those 25 years who could justifiably say something bad about her. She’s a class act that will be remembered for many years to come. For a girl that wore potato sacks and came from Cassie Jusco, Mississippi. I think we can say she did pretty well. And we got to benefit from what she brought to the world. Thanks for being here. We’ll see you on our next episode of Money With Mak and G.

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