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.

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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.

Oprah

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.

Oprah

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.

Oprah

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.

Oprah

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.

Oprah

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:

When I was called in and put on the edge of being fired, and certainly demoted, and knew that firing was only a couple weeks away, I was devastated.

I was 22 and I mean embarrassed by the whole thing because I'd never failed before and it was that failure that led to the talk show because they had no place else to put me.

They put me on a talk show one morning and that, I'm telling you, my very first interview was the Carvel ice cream man and Benny from All My Children, never forget it, and I came off the air thinking this is what I should have been doing because it was like breathing to me, like breathing, you just talk, be yourself is really what I've learned to do, and so from the very first day I did my very first talk show I felt I knew it was the right thing to do.

Oprah

The local talk show Oprah joined was called People Are Talking, a great name by the way, with co-host Richard Sher. The first episode aired on August 14, 1978.

While Oprah found her calling as a talk show host, Baltimore ultimately wasn’t where she was meant to be:

The truth is I have from the very beginning listened to my instinct. All of my best decisions in life have come because I was attuned to what really felt like the next right move for me. And so, it didn't feel right. I knew that I wouldn't be there forever.

Oprah

Oprah also knew she wouldn’t be in Baltimore forever because her co-host on the show, who was doing the same job as her, was making more money.

She just knew she wasn’t going to be able to get what she needed from that job.

So she left.

AM Chicago, which recently had a host leave, had an opening, and Oprah sent in her audition tape to host the 30-minute show which at the time had very low ratings.

Dennis Swanson, who was the television executive hiring for the open role, asked Oprah to come in to do a mock version of the show.

He was blown away.

It’s also worth noting, Dennis is an interesting character in his own right. He famously brought Regis and Cathy Lee together and it was also his idea to stagger the Winter and Summer Olympics every two years.

He’d hire Oprah, putting his job on the line to do so, and having the belief that what their TV station needed was someone who was different than the norm. Oprah was not only different, she was exceptional.

But everyone thought she’d fail in Chicago:

So when I got the call to come to Chicago after starting with a co-anchor and working in talk for several years, I knew that it was the right thing to do.

And I knew that even if I didn't succeed, cuz at the time there was a guy there named Phil Donahue who was the king of talk and was on in Chicago, and every single person, except my best friend Gayle, said you are gonna fail. Every single person.

My bosses by this time thought I was terrific, and said, “You're walking into a land mine. You're gonna fail. You're gonna fail. Chicago's a racist city. You're black you're not gonna make it.” Everything to keep me sane. Then they offered me a car and apartment and all this stuff, and I said, “No, if I fail, then I will find out what is the next thing for me.”

Oprah

She made the move anyways, going to Chicago in 1984, the same year Michael Jordan joined the Bulls. How crazy for two future icons to join the city at the same time?

The first episode Oprah did of AM Chicago aired in January 1984 and within months the show became the highest-rated talk show in Chicago passing Donahue, which had led for years. Phil Donahue, the host, had in many ways invented the daytime talk show format and his show had national syndication.

In September 1984, AM Chicago changed its name to The Oprah Winfrey Show and by then had expanded from a 30-minute show to a 60-minute show.

Oh, and remember that whole “making $30,000 by age 30” thing with her best friend Gayle King? Well, Oprah was already making $230,000 at this time.

Having her own show also led to Quincy Jones discovering Oprah while he was on a business trip in Chicago, and selecting her to play the role of Sofia in The Color Purple.

Oprah had wanted to become an actress for some time and was beyond grateful:

Quincy Jones had, I would not even say an important role, I would say THE role in my acting career. Quincy Jones discovered me.

Oprah

Oprah starred in The Color Purple in 1985 and was even nominated for an Oscar.

At one point during the filming of the movie though, she told the director, Steven Spielberg, that she had to leave for a few days.

Why?

Because she was negotiating her national syndication deal.

The Oprah Winfrey Show Goes National

In 1986, Oprah started her own company, Harpo Productions Inc. (Oprah spelled backward), and signed a national syndication deal with King World Productions, a company that sold local shows nationally, with Wheel of Fortune being one example.

On September 8, 1986, the first episode of Oprah’s nationally syndicated show aired with Oprah, in front of a studio audience of 75, announcing:

I’m Oprah Winfrey, and welcome to the very first national Oprah Winfrey Show!

The night before the show, Oprah wrote in her journal:

I keep wondering how my life will change, if it will change—what all this means. Why have I been so blessed? Maybe going national was to help me realize that I have important work, or that this work is important.

Oprah

Her life would certainly change and The Oprah Winfrey Show would absolutely explode in popularity.

By October, in Chicago alone, 43% of households using a TV during the time her show aired were watching it, 312,000 households in all.

And she was also the top talk show in New York City, Los Angeles, Philadelphia, and San Francisco in the show’s first four weeks.

The show became the top daytime talk show in America, bringing in double the national audiences as the previous leader, Donahue.

Oprah’s first season of national syndication aired 228 episodes. She personally made between $11 million and $12 million from her share of the profits. She’s 32 years old when she becomes a millionaire, which, given her background and what she had to endure growing up, is astounding.

But what went into making the show a success early on?

Of course, we know Oprah herself was the biggest reason, but the show’s success goes beyond Oprah, her team was also putting in work:

We worked insane hours, and we were really single-minded about it. It was our lives. We ate it, breathed it, slept it. We worked weekends. We worked nights. None of us had a life outside of that.

Chris Tardio, Producer

And Oprah led the charge, setting high expectations:

Oprah gave a lot to us, but she expected a lot, too. She had really high standards. It was her ass on the line every day, and we felt that. It was palpable. She wasn’t nice. [She was] kind, openhearted. She’s not going to say, “That’s a great show” unless it’s a great show. And you’d hear about it if it wasn’t. So you wanted to deliver the goods for her.

Alice McGee, Publicist and VP of Communications

In the early days, nobody knew what they were doing either:

We were flying by the seat of our pantyhose. The only strategy was, “What do we think will work?” And every single thing, I gave a gut check to. And that’s how we operated…

When we’d have our meetings, [we’d ask], “What were people talking about at the hairdresser this week? What are people talking about in the restaurants you’re in? What are people talking about in your family?” That’s where we built the shows, right straight up out of our lives.

Oprah

With the popularity of the show, Oprah was creating raving fans.

Early on, she was already receiving 1,100 letters per week from fans of the show.

And Oprah and her team focused on the audience they were serving. They even came up with a persona, Suzy, the suburban woman, and thought constantly about what she wanted and what she liked.

Building on the success of the first season of her show’s national syndication, Oprah made a number of important moves that would later make her a billionaire.

Making Moves

In the first two seasons since starting national syndication, Oprah’s show would bring in $115 million in revenue.

In 1988, Oprah acquired her talk show from ABC’s WLS-TV in Chicago. Her production company would produce it and open Harpo Studios to do so.

This came about from the urging of Oprah’s business partner, Jeffrey Jacobs, a Chicago lawyer who Oprah started working with in 1984 after firing her agent.

The move to bring Jeff on board was a critical one.

Jeff not only encouraged Oprah to buy her show and build her own production studio, but he also got her a stake in King World Productions, the company that distributes her show.

But why bring on Jeff in the first place?

It came from Oprah sensing her old agent wasn’t doing his job well:

Three separate [ABC] people stopped me to tell me what a great guy my agent was and that didn’t make sense to me. Why were people going out of their way to praise the fellow?

Oprah

Oprah would go on to say, “I’d heard Jeff is a piranha. I like that. Piranha is good.

She also would say that Jeff, “Took the ceiling off my brain.

And Jeff got paid for that as well, earning a 5% stake in the company in 1986 and three years later earning an additional 5% stake.

Well, with the ceiling removed, Oprah took her business to the next level.

And remember that studio I mentioned?

It cost Oprah $20 million to buy and renovate, but the 88,000-square-foot facility would become the largest film and TV production studio in the Midwest and also become the home of her show starting in 1990.

Here’s why she opened it:

I ended up building my own studio because when I was shooting The Color Purple I was not allowed the kind of freedom that was necessary to do that work and what I really want to do is to create films for myself and other people that uplift, enlighten, and courage and entertain people and in order to do that I need time.

So I was working under a situation where I only had so much time to do it so when the studio came about, as I say, to me success is a process, there was this empty studio, old vacant lot available and I have a partner who said to me, “You know, there's a studio available and you can take over your own show,” well it had never occurred to me that that could happen. The studio came to be as a roundabout way for me to get to be an actress.

Oprah

If you didn’t catch that, her partner who told her that there was a studio available was Jeff. He stays behind the scenes but undoubtedly is an important piece of her empire and showcases the value of surrounding yourself with the right people.

Another important piece of her empire?

Her constantly evolving show.

The Early Evolution of Her Show

You can’t create a media empire without compelling media.

Obvious, right?

Well, with a daily talk show, the challenge is in creating compelling media repeatedly, year after year.

Oprah certainly did that.

In 1988, the same year she bought her show, she aired her most-watched episode ever, revealing her 67-pound weight loss journey by wheeling out 67 pounds of animal fat in a wagon. It was something she later regretted, but the episode itself was viewed by 45 percent of Americans who had their TV on at that time

Absolutely crazy.

After a couple of questionable early shows, Oprah made more changes:

I went and I had a meeting with the producers, cuz I just had the Klan before, now I got the adulteress here and, some uplifting show, I must say. And I said to the producers, “We are gonna change. We're gonna turn this around. And I am no longer gonna be used by television. I am going to use television.”

What a concept! I am gonna use television, as a force for… I didn't say at the time for good, I said, you know, let's think about what we wanna say to the world and how we wanna use this as a platform, to speak to the world. How do we want to see the world change? How do we wanna impact the world, and then let all of our shows really, be focused, and seated around that.

I then said to the producers exactly what I said to you backstage. Do not bring me a show, unless you have fully thought out what is your intention for doing it.

Oprah

Oprah’s show would be the top show for decades, but the peak of her viewership actually came in the early 1990s when she was getting 12-13 million viewers PER DAY.

Those numbers are wild.

She would also become known for her ability to get guests to open up, sharing more than they probably normally would have, but why?

The reason why people open up so much on my show is because I open up. They feel comfortable doing it and they know that I am NOT going to ridicule them. I want everybody on the show, even if I disagree with you, to leave with a sense of dignity to maintain their own dignity.

Oprah

In 1993, she started Harpo Films, the film division of her production company, and the next year, she decided she didn’t want to do “trash TV” anymore.

She turned 40 in 1994, discovered her favorite book, The Seat of the Soul, and she started talking about and integrating the idea of intention into her show, even having it become part of the team’s planning process.

That year, her show grossed $196 million.

And the budget to produce it? $30 million.

Harpo Productions would make nearly $100 million that year, with Oprah’s business partner, Jeff, getting 10% or about $10 million and Oprah herself making about $74 million.

The brand that Oprah built also gave Jeff leverage to negotiate deals, with one notable deal being the reduction in King World’s revenue split from 35% to 30% over the course of five years.

By 1995, local stations were paying $100,000 per week to air her show, which the next year would launch her famous book club and “Oprah’s Favorite Things” segments.

With her book club, she'd often get a million people, or roughly 10% of her audience at the time, to actually buy the book. It goes to show the influence she had at that time.

A few years later, her audience’s appetite for reading would be fed with Oprah’s own product.

“The Most Successful Startup Ever in the Industry”

In 2000, in conjunction with Hearst Magazines, Oprah introduced O, the Oprah Magazine. 

This audience was more upscale than for her show, showcasing a bit of the value in diversifying the mediums of your content.

It’s also interesting to see that she launched her show nationally in 1986, but didn’t launch a magazine until 14 years later. She stayed focused and when it came time to launch the magazine, it exploded in popularity.

By 2001, the magazine was selling 2.5 million copies every month, bringing in $140 million in revenue that year and, while sales dipped a bit in 2002, the first international edition of O was released.

An April 2002 profile in Fortune called O, The Oprah Magazine “The most successful startup ever in the industry.”

The same year, her show brings in $300 million for Harpo Productions, remaining the No. 1 daytime talk show.

Harpo has a team of 221 employees at this time and production costs of her show grew to $50 million.

When asked about the growth of her company, Oprah offered up this gem:

I don't care about being bigger, because I'm already bigger than I ever expected to be. My constant focus is on being better. Should I be doing multimedia video production? Or seminars on the internet? How can I do what I'm already doing in a more forceful way?

Oprah

Well, that focus on “being better” paid off in a big way.

Billionaire & The Oprah Winfrey Network

In 2003, at 49 years of age, Oprah becomes a billionaire.

It’s the most improbable of climbs to the top and yet, Oprah is nowhere near finished.

The following year, the famous “You get a car!” episode of her show airs, with every member of the audience receiving a Pontiac G6.

In 2006, Oprah signed a 3-year deal with XM Satelite Radio for $55 million.

Two years later, in 2008, she has a scripted programming deal with HBO and announces her plan to create OWN: Oprah Winfrey Network.

The network officially launches in January 2011, but it initially didn’t turn out how Oprah thought it would:

What I did not realize until it was done is that we had created a habit. And that habit was a 4:00 habit.

Oprah

Who helped the network in a big way?

Tyler Perry, who I previously wrote about in this newsletter edition.

He would strike a deal with OWN in 2012, creating scripted programming for the network until 2019.

OWN would become profitable by June 2013.

But of course, during that time something else happened - the end of her show.

The End of an Era

The final episode of Oprah’s talk show aired on May 25, 2011, capping an unprecedented 25-year run.

200 talk shows came and went during the run of The Oprah Winfrey Show, but Oprah and her team stayed focused on their own show, with Oprah repeatedly saying, “You can only run your own race.

Here’s why Oprah’s show worked so well, from a talk she gave at Stanford:

This is what I know to be true, the reason why the show worked is because I understood the audience, my viewers, the people who watched us everyday… I always understood that there really was no difference between me and the audience.

At times, I might have had better shoes, but at the core, the core of what really matters, we are the same. You know how I know that? Cuz all of us are seeking the same thing.

You're here at this fabulous school and will go out into the world. And each pursue, based upon what you believe your talents are, what your skills are, maybe your gifts are, but you're seeking the same thing. Everybody wants to fulfill the highest, truest expression of yourself as a human being. That's what you're looking for. The highest, truest expression of yourself as a human being.

Oprah

By the end, Oprah’s show was in 145 countries and had 48 million weekly viewers in the US alone.

She did 4,561 episodes of the show in total including 150 episodes per season in the final years.

About 1.3 million audience members attended her show in person during those 25 years, Oprah had more than 28,000 guests come on the show, and she received a staggering 20+ million letters from fans during that time.

An estimated 55 million books were sold because of Oprah’s Book Club and there were 283 different types of products given away during “Oprah’s Favorite Things” episodes.

Her show helped catapult the careers of a number of people, especially two entrepreneurs I’ve written about, Sara Blakely and Tory Burch, not to mention touching the lives of millions of people.

Of course, since the show ended more than a decade ago, Oprah has done many more things, continuing to do a number of notable interviews, growing OWN, working with Apple and Apple TV+, and more.

She’s a legend, there will never be another quite like her, and, with the rise of the internet, her show’s success will be nearly impossible to replicate.

Oprah’s Wisdom

In each edition of the Just Go Grind newsletter, I like to include a few more quotes at the end from my research into the founder who is featured, sharing their wisdom.

On listening to your inner voice:

And every decision that has profited me has come from me listening to that inner voice first, and every time I've gotten into a situation where I was in trouble, it's because I didn't listen to it. I overrode that voice, that instinct, within my own head, my own thinking. I tried to rationalize it, I tried to tell myself, “But, you know, okay, you're gonna make a lot of money.”

And so, I sit here, profitable, successful by all the definitions of the world. But, what really, really, really resonates deeply with me is that I live a fantastic life. My inner life is really intact. I live from the inside out and so, everything that I have, I have because I let it be fueled by who I am and what I realized my contributions to the planet could be.

Oprah

On success:

I think that success is a process and I believe that my first Easter speech and the Kosciusko Baptist Church at the age of three and a half was the beginning and that every other speech, every other book I read, every other time I spoke in public was a building block so that by the time I first sat down to audition in front of a television camera and somebody says, “Read this,” what allows me to read it so comfortably and be so at ease with myself at that time was the fact that I'd been doing it a while. If I'd never read a book, never spoken in public before, I would have been traumatized by it.

Oprah

On failure:

I just wanna end with this: there are no mistakes. There really aren't any, cuz you have a supreme destiny.

When you're in your little mind, in your little personality mind, or you're not centered, you really don't know who you are but you come from something greater and bigger. We really all are the same. You don't know that, you get all flustered, you get stressed all the time, wanting something to be what it isn't.

There's a supreme moment of destiny calling on your life. Your job is to feel that, to hear that, to know that and sometimes, when you're not listening, you get taken off track. You get in the wrong marriage, the wrong relationship, you take the wrong job. Yeah, but it's all leading to the same path. There are no wrong paths. There are none.

There's no such thing as failure really, because failure is just that thing, trying to move you in another direction. So you get as much from your losses, as you do from your victory cuz the losses are there to wake you up. The losses are to say, “Fool, that is why you go to school, so that CBS can call you.”

So when you understand that, you don't allow yourself to be completely thrown by a grade or by a circumstance because your life is bigger than any one experience.

Oprah

That to me has been the greatest lesson of my life is to recognize that I am solely responsible for it and not trying to please other people, not living my life to please other people but doing what my heart says all the time, that's the biggest lesson for me.

Oprah

On the value of being honest with yourself:

I think the most important thing to get ahead falls back to what I truly believe in and that is the ability to seek truth in your life and that's on all forms, you have to be honest with yourself.

You can be pursuing a profession because your parents say it's the best thing. You can be pursuing a profession because you think you'll make a lot of money. You can be pursuing a profession because you think you're going to get a lot of attention. None of that will do you any good if you're not being honest with yourself and the honesty comes from your natural born instinct which will tell you when you're doing something whether or not this feels right.

You feel a sense of accomplishment and fulfillment and worthiness to the world in such a way that you know you're doing the right thing, you don't have to ask anybody.

Oprah

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