Oprah's Path to Extraordinary Success

How She Became a Multi-Billion Dollar Media Mogul

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Oprah Winfrey

Oprah Winfrey is, let’s be real, enough of a legend to just be called a singular name - Oprah.

She’s an icon and she dominated daytime television like nobody had before her and likely like nobody ever will again.

Her show was critical for a number of entrepreneurs I’ve written about previously, including Sara Blakely and Tory Burch, as well as Tyler Perry.

Her story is one of the most remarkable you’ll hear of, becoming a self-made billionaire, and one of the richest women on the planet.

There’s so much to her story, more than I can cover here in one post and everyone, especially entrepreneurs, can learn a great deal about resilience, self-belief, and the value of ownership from it.

Let’s get to it.

Early Days

To say Oprah had a rough start to life would be a colossal understatement.

Born in Kosciusko, Mississippi in 1954. Her name was actually Orpah at birth but was misspelled on her birth certificate so she became Oprah.

She was born to a single teenage mom, Vernita Lee, who was a housemaid, and her father, Vernon Winfrey, who at the time of Oprah’s birth was in the Armed Forces.

Oprah grew up in poverty, living with her grandmother, Hattie Mae, for the first 6 years of her life, learning to read before age 3 and speaking in her church around the same age. That practice of speaking would pay off later in life, as we all know.

Oprah would later reflect on her grandmother’s impact on her:

I came to live with my grandmother because I was a child born out of wedlock and my mother moved to the north, she's a part of that great migration to the north in the late 50s, and I was left with my grandmother like so many other black youngsters were left to be taken care of by their grandmothers and grandfathers and aunts and uncles and I was one of those children.

It actually probably saved my life. It is the reason why I am where I am today because my grandmother gave me the foundation for success that I was allowed to continue to build upon. My grandmother taught me to read and that opened the door to all kinds of possibilities for me and had I not been with my grandmother and been with my mother struggling in the north you know moving from apartment to apartment I probably would not have had the foundation that I had.


At age 6, Oprah moved to inner-city Milwaukee to live with her mother.

The next few years would be her most traumatic.

She was raped at 9 years old by a relative, something she later revealed on her show on November 10, 1986, and she also suffered years of sexual abuse.

At age 13, she ran away from home, and by 14 she gave birth to a son, born prematurely, and who sadly passed away in infancy.

Oprah started high school in Milwaukee but after a rebellious streak was sent to live with her father, Vernon, in Nashville.

He was a godsend.

Yes, Vernon was strict, but it paid off for Oprah, who became an honors student, and, as she’d later say, he saved her:

When my father took me, it changed the course of my life. He saved me. He simply knew what he wanted and expected. He would take nothing less.


She expanded on his impact on her with an example of his expectations for her in another interview:

He had some concerns about me making the best of my life and would not accept anything less than what he felt was my best.

I remember my father saying to me, “You can't bring C’s in this house because you're not a C student. If you were a C student you could because I'm not trying to make you do or be anything that you can't be, but you're not a C student, you’re an A student, so that's what we expect in this house.”

And it was just so matter-of-fact and I mean I knew he was not faking it one bit so I just I never even tried it, I never even like tried to bring in a C because I realized it's just not acceptable.


We all need people like that in our lives to hold us accountable and help us become our best selves.

Oprah had that person in Vernon and he changed the trajectory of her life.

High school would be a pivotal time for Oprah.

At 17 years old, she won the Miss Black Tennessee beauty pageant. Yes, there’s a lot that could be said about the problems of beauty pageants and why there needed to be a separate one for black people, but alas, this was helpful for Oprah at the time.

From that experience, she landed a job in radio, working at the WVOL radio station part-time during her senior year of high school. Her first two years of college she’d work there as well.

Oprah would attend Tennessee State University after receiving a full scholarship for winning a speaking contest.

In the next few years, she’d find her calling and build the foundation for her extraordinary success.

Getting Into Television

While at college, Oprah didn’t waste any time getting a jump on her career.

As a freshman, she was recruited into television:

I started getting calls about my freshman year to come into television. I had never thought about it. And still was living at home, and couldn't figure out how I'd manage those, I had biology at 1 o'clock, and so I couldn't figure out how I would be able to manage my schedule.

And Mr. Cox said to me, the one same professor who said, “You can't draw a straight line with a ruler,” I came back from taking this phone call and he said, “Who was that?” I said, “There's this guy at CBS he keeps calling me, he wants me to interview for a job,” and Mr. Cox said, “That is why you go to school, fool, so that CBS can call you. That is why you are in school. You leave now and go call him back.”

And, I did. And I was hired in television not knowing anything about it.


At just 19 years old, Oprah would become the youngest news anchor and the first black female anchor at WLAC-TV in Nashville.

She was also making $10,000 per year while still in college, even getting a job offer to go to Atlanta for $40,000, but she turned it down because it didn’t feel right to her.

In 1976, she moved to Baltimore where she would co-anchor the six o’clock news.

She was 22 and had, in hindsight, hilarious ambition:

A couple of years later I moved to Baltimore… By this time, 22, I'm making $22,000. I met my best friend Gayle there who said, “Oh my god, can you imagine when you’re thirty and your making $30,000? And then you're 40 and then it's $40,000?” We actually had that conversation in the bathroom.


Spoiler alert: Oprah would make just a wee bit more than that.

However, in 1977, she was demoted from doing the news, a move that changed her life forever, here’s why:

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