Oprah's Path to Extraordinary Success
How She Became a Multi-Billion Dollar Media Mogul
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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 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.
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:
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:
She expanded on his impact on her with an example of his expectations for her in another interview:
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:
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:
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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