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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:

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:

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:

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:

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:

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:

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

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:

And Oprah led the charge, setting high expectations:

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

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:

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:

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:

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?

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:

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:

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:

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:

On success:

On failure:

On the greatest lesson of her life:

On the value of being honest with yourself: