The Business of Celebrity: Breaking Down the Business Ventures of Oprah Winfrey

By Charlotte Fortier

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Oprah Winfrey is undeniably one of the most influential and successful women in the world. From humble beginnings in rural Mississippi to becoming the queen of daytime television, Oprah’s career is nothing short of extraordinary. Best known for hosting The Oprah Winfrey Show, which ran for 25 years, Oprah’s influence extends far beyond her television career. She is a media mogul, philanthropist, and entrepreneur whose business ventures and wealth-building strategies have reshaped how we think about celebrity and success.

 

Oprah’s business acumen is often overshadowed by her iconic TV show, but it’s the entrepreneurial moves she made off-camera that truly built her empire. Here are some of Oprah’s most significant, yet often lesser-known, business ventures:

 

Harpo Productions

Oprah founded Harpo Productions (Oprah spelled backward) in 1986, which became the cornerstone of her business empire. The production company has created films, television specials, and produced The Oprah Winfrey Show as well as Dr. Phil, The Dr. Oz Show, and Rachel Ray. Harpo not only allowed Oprah to maintain creative control but also made her one of the few media moguls to own her own production company.

 

OWN: Oprah Winfrey Network

Oprah’s OWN Network, launched in 2011, was a significant leap into the cable network business. While the network initially struggled, Oprah’s influence and investment eventually turned OWN into a profitable entity. It now generates hundreds of millions of dollars a year in revenue through a mix of original programming, documentaries, and partnerships with companies like Discovery Communications.

 

O, The Oprah Magazine

For almost 20 years, O, The Oprah Magazine became one of the most widely read publications in the U.S. Oprah was heavily involved in editorial decisions, focusing on lifestyle, self-improvement, and empowerment. While the print version of the magazine ceased publication in 2020, Oprah’s digital presence remains strong with her lifestyle brand and O.com.

 

Weight Watchers (WW)

In 2015, Oprah invested $43 million into Weight Watchers and took an active role as its spokesperson. The investment led to a massive surge in the company’s stock and brought Oprah back into the wellness space she had helped shape through her show. Her involvement was not just as a celebrity spokesperson, but as an active board member, helping guide the company through a major rebranding effort. Oprah later sold off a portion of her shares, though she continues to hold a stake in the company.

 

Oprah’s Book Club

A mainstay of Oprah’s brand, Oprah’s Book Club has turned countless authors into bestsellers. The book club, launched in 1996, started as a segment on The Oprah Winfrey Show but later expanded into a full-fledged book publishing imprint under Flatiron Books. Oprah still selects books for her club, generating millions in sales for her chosen authors.

 
The Oprah Winfrey Foundation and the Oprah Winfrey Operating Foundation

Oprah’s charitable endeavors are a key part of her legacy. Through her foundations, Oprah has donated hundreds of millions of dollars to causes related to education, empowerment, and poverty alleviation. She famously donated $12 million to the creation of the Oprah Winfrey Leadership Academy for Girls in South Africa, and continues to focus on helping underserved communities around the world.

 

‘Oprah’s Favourite Things’ Product Line

Every year, Oprah’s list of Favorite Things (products she endorses) is a massive marketing success. The list, which began as a segment on her show, has evolved into a billion-dollar brand. Oprah has also used her platform to partner with several brands to create exclusive, Oprah-branded products in categories such as food, home décor, and wellness.

 
Oprah’s Apple TV+ Show

In 2019, Oprah signed an exclusive partnership with Apple TV+ to create original content, including interviews, documentaries, and other productions. Oprah’s deal with Apple, reportedly worth $100 million, bolstered her already expansive media empire by tapping into the streaming market, where she continues to build her brand of deep, authentic conversations.

 

Outside of her business venuture, Oprah Winfrey also has a legendary real estate portfolio. Known for her impeccable taste and luxury properties, Oprah has accumulated several significant pieces of real estate over the years:

 

Oprah’s The Promised Land estate in Montecito, California, is the crown jewel of her real estate portfolio. Acquired in the early 2000s for around $50 million, the 65-acre property is a breathtaking example of luxury, complete with a Mediterranean-style mansion, lush gardens, and vast grounds. But Oprah’s connection to Montecito goes far beyond this initial purchase.

 

In 2015, she added to her holdings by purchasing a 23.26-acre equestrian estate nearby for $28.85 million. Then, in late 2019, she secured Jeff Bridges’ long-time retreat for $6.85 million, increasing her total Montecito estate size to nearly 70 acres.

 

Not one to rest on her investments, Oprah further expanded in 2021, buying a 2-acre property for $10.8 million. She split the estate in two, selling the main farmhouse—boasting stunning mountain and ocean views—to actress Jennifer Aniston in 2023 for $14.8 million. Oprah then sold the two smaller cottages to her close friend and personal trainer Bob Greene for $2.3 million. These moves not only reflect Oprah’s refined taste but also her sharp real estate instincts, as each acquisition has further cemented her place in Montecito’s exclusive and lucrative market.

Oprah also owns several properties in Hawaii, including a massive estate on the island of Maui. She purchased a 163-acre property for $32 million, which includes a main residence, guesthouses, and vast gardens. Oprah has also bought several neighboring properties, and her Hawaiian holdings are worth an estimated $100 million.

 

In Chicago, Oprah owns a penthouse in the prestigious Water Tower Place, which she purchased for $5.6 million. The property boasts stunning lake views, modern amenities, and is in one of Chicago’s most luxurious buildings. While Oprah doesn’t spend much time in Chicago, this is one of the key properties in her real estate portfolio.

 

Net Worth:

As of 2025, Oprah Winfrey’s net worth is estimated to be around $2.5 billion. This makes her one of the wealthiest women in the world, and the richest African-American woman in history. Her wealth is derived from her smart investments in television, media, and business ventures, as well as her numerous philanthropic efforts. 

 

Looking ahead, Oprah’s entrepreneurial journey shows no signs of slowing down. With her deep commitment to storytelling, empowerment, and social change, it’s likely that she will continue to shape the media landscape through her collaborations with Apple TV+ and beyond. Oprah has also expressed interest in further expanding her influence in the wellness and mindfulness sectors, possibly through new ventures in digital platforms and health-related content.

 

Moreover, her philanthropic efforts remain a key focus, with plans to continue investing in educational initiatives and global outreach programs. As always, Oprah’s ability to reinvent herself and remain relevant in an ever-changing world will ensure that her legacy only grows richer in the years to come. Whether it’s through new projects, strategic partnerships, or groundbreaking investments, Oprah Winfrey will undoubtedly keep inspiring generations of entrepreneurs and leaders.