From media icon to business mogul: A look at Oprah’s path to building a $2.8 billion fortune

BY Ben Ebuka Oji October 13, 2023 3:14 PM EDT
Oprah Winfrey attending Barack Obama Campaign Rally for Democratic Presidential Primary with Oprah Winfrey, The Verizon Wireless Arena, Manchester, NH, December 09, 2007: ShutterStock: 181470764
Oprah Winfrey attending Barack Obama Campaign Rally for Democratic Presidential Primary with Oprah Winfrey, The Verizon Wireless Arena, Manchester, NH, December 09, 2007: ShutterStock: 181470764

Media icon Oprah Winfrey has ascended to the exclusive realm of dollar-billionaires, a status attained by only a select few worldwide. However, for someone like Winfrey, who emerged from humble beginnings in a society marred by systemic bias, racial discrimination, and segregation, the journey to joining the ranks of the “world’s billionaires” was far from an easy one.

Born on a modest farm in Kosciusko, Mississippi, on January 29, 1954, to parents Vernon Winfrey and Vernita Lee, Winfrey’s early life was marked by separation and adversity, with her parents parting shortly after her birth. Raised under the loving care of her maternal grandmother, she endured a challenging childhood marred by abuse, trauma, and unmet basic needs.

Yet, even amidst these hardships, Winfrey displayed remarkable talents and promise, excelling academically despite her family’s struggles. She remained resolute in her pursuit of education, garnering numerous honors and awards, including a full scholarship to Tennessee State University. Her teenage years saw her shuttling between her parents’ homes, and she attributes her strong sense of responsibility to her father’s strict upbringing.

At the age of 19, Winfrey embarked on her career journey, landing her first job at WTVF, a CBS station in Nashville, Tennessee. Her career trajectory took her to various media organizations in different cities, eventually bringing her to Chicago in 1983, where she hosted a 30-minute talk show. With her unparalleled presentation skills and media prowess, the morning talk show quickly gained a devoted following, transforming Winfrey into a nationwide media sensation within a year.

Her charisma drew the attention of not only the public but also revered figures like film analyst Roger Ebert, who provided guidance and encouraged her to syndicate her talk show in 1986. The show expanded to an hour and was rebranded as “The Oprah Winfrey Show,” solidifying her status as one of America’s most beloved and influential media personalities. At the age of 32, Winfrey became the first African-American syndicated television host.

Winfrey’s career continued to evolve, encompassing acting and other forms of entertainment. She also ventured into the business side of the industry, establishing her television production company, Harpo Inc. This groundbreaking move made her the first Black person and the third American woman to own a major studio.

Over the years, she strategically diversified her sources of income through prudent investments and lucrative deals, converting her career into a thriving media and business empire. As a serial investor, she astutely reinvested profits from her shows, films, and other endeavors into high-yield ventures. This shrewd financial acumen has culminated in a sprawling business empire valued at an impressive $2.8 billion, according to Forbes’ recent billionaire tracking.

Below, we delve into some of the exclusive investments, businesses, and assets owned outright by Winfrey, as well as those held in partnership deals.

Oprah Winfrey Show

At the advice of the Chicago-based film critic Roger Ebert, Winfrey signed a syndication deal with King World, a media distributor, which resulted in the Oprah Winfrey Show airing nationally for the first time on September 8, 1986. The show gained millions of viewers from over 134 countries and became the highest-rated talk show in TV history. The show concluded on May 25, 2011, after 25 years of airing 4,561 episodes. The success of the Oprah Winfrey Show created more spin-off ventures, including the O Magazine.

Harpo Inc.

In 1986, Winfrey launched Harpo Studios, a multimedia production company through which she handles her talk show and other media productions, including popular films like ‘The Color Purple,’ ‘Selma,’ and Beloved. She later sold the Chicago-based Harpo Studios a few years ago but still retains the ownership of Harpo Inc.

Oprah Winfrey Network (OWN)

On January 1, 2011, Winfrey launched OWN a few months before ending the iconic Oprah Winfrey Show. OWN was established through a 50/50 joint venture partnership between Warner Bros. Discovery and Harpo Studios. OWN became a premier cable destination for African-American audiences seeking lifestyle and entertainment programming. But by December 2017, Discovery acquired 24.5% of OWN from Winfrey, leaving her with 25.5% worth, about $75 million, according to Forbes’ estimate. Discovery subsequently increased its stake to 95% in December 2020, making Harpo Inc. a “significant” minority stakeholder. Winfrey remains contracted to the channel through (at least) 2025. The present value of her stake is not known, but it is estimated to be worth around $100 million.

Discovery Deal

The purchase of more OWN shares by Discovery in December 2020, resulted in a $35 million stock deal that granted Winfrey’s Harpo Inc. approximately 1.34 million shares in Discovery. In April 2022, Discovery Inc. merged with WarnerMedia to form Warner Bros. Discovery; resulting in the placement of OWN under common ownership with Warner Bros. Television which has produced many of OWN’s scripted series.

Movie Gigs

Winfrey showcased her multifaceted talents by venturing into the world of acting, making her big-screen debut as Sofia in Steven Spielberg’s ‘The Color Purple’ (1985), a cinematic adaptation of Alice Walker’s Pulitzer Prize-winning novel of the same title. Her foray into acting continued with the 1988 film ‘Beloved,’ a project she both starred in and produced, which was based on Toni Morrison’s Pulitzer Prize-winning novel. Throughout her career, this TV luminary garnered substantial earnings from a range of notable films and television endeavors, including the following:

  1. In the 1998 film adaptation of Toni Morrison’s novel, she earned an impressive $10 million for her portrayal.
  2. She lent her voice to the character Eudora in Disney’s 2009 animated feature ‘The Princess and the Frog,’ securing a substantial $15 million for her contribution.
  3. Oprah also graced the screen in the 2018 Disney fantasy film ‘A Wrinkle in Time,’ commanding a remarkable $20 million for her role.

Oprah Winfrey created the website, a premier resource and destination for self-improvement and self-empowerment, providing people with extensive information and other resources on air, online, and in print. averages 71 million page views and 7.5 million unique visitors monthly.

Oprah Radio

Through Harpo Productions’ radio division, ‘Harpo Radio,’ Oprah Winfrey launched a talk radio channel signed exclusively for Sirus XM Satellite Radio. The channel officially launched and began airing on September 25, 2006, covering topics such as self-improvement, health, nutrition, fitness, home, and other current events. The eight-year deal ended on January 1, 2015. However, the original three-year deal Oprah Winfrey signed in February 2006 paid her $55 million.

O (The Oprah Magazine) and Oprah Daily

O was once American women’s favorite leading magazine. It was founded by Oprah Winfrey and published by Hearst Magazines, with its first issue on April 19, 2000. The magazine highlighted personal growth and empowerment and covered fashion, fitness, food, and relationships. In 2020, the publisher announced the closure of the print version of the magazine, with its last publication in December of that year. In 2021, Oprah Winfrey and Hearst rebranded it as ‘Oprah Daily,’ a membership-only community where you can connect live with Oprah Winfrey and all things in the Oprah universe. Oprah Daily became the digital product offering the latest thoughtful and life-changing stories, while ‘O Quarterly’ is the print edition published four times a year.

The Oprah Conversation

The media mogul launched ‘The Oprah Conversation’ in partnership with AppleTV+. The Oprah Conversation is an interview talk show that premiered on Apple TV+ with one season of fifteen episodes, from July 30, 2020, to November 5, 2021. It featured interviews and discussions between Oprah Winfrey and thought leaders across a range of topics.

Other Profitable Ventures

Aside from her media exploits, Oprah Winfrey has earned tremendously from other income-spinning ventures, including the ones below.


Winfrey has authored a series of highly successful bestselling books, including memoirs, self-help guides, and cookbooks, collectively generating millions of dollars in sales.

Weight Watchers

In October 2015, Winfrey paid $43.5 million for a 10% stake in Weight Watchers, a global health and nutrition platform inspiring good health through lasting weight loss, behavior change, nutrition science, and connection with the ideal food and activities for the body. Three years later (2018), the investment gained a massive value of over $400 million. However, she now owns a lesser stake today after selling about two million shares from her initial nearly 5.5 million stakes in March 2018, making a whopping $110 million from the sale, as reported by CNN.

Real Estate

Over the years, Winfrey has made substantial real estate investments, including properties in California, Nashville, and Hawaii. Notable acquisitions include a Chicago home sold for $4.625 million in 2015, an $8.3 million 43-acre estate in Washington State in 2018, and 870 acres in Kula, Hawaii, for approximately $6.6 million. She also expanded her Montecito estate, known as “Promised Island,” from 42 to about 70 acres, now valued at over $100 million. In March 2023, Winfrey sold the Ranch House of the “Promised Land” estate for $14 million. Additionally, she owns approximately 13 properties in Maui, including a 3-acre property in Kula with a 1,139-square-foot building, purchased for $7 million in 2021.

True Food

Oprah Winfrey recently invested in True Food Kitchen, a food restaurant chain offering ideal science-backed dishes and drinks for good health, vitality, and longevity.


The Harpo Inc. CEO acquired a stake in the goat milk company Oatly when the company sold a $200 million stake to a few investors that included other high-profile figures like Jay-Z.

Winfrey possesses an exceptional talent for assessing the investment landscape and identifying lucrative opportunities. Her remarkable journey from a modest and adversity-ridden background to becoming one of the world’s billionaires and a prominent influencer underscores the importance of determination, diversification, hard work, and purpose as vital elements in achieving extraordinary success.