How Reese Witherspoon made fortune being best friend every woman needs

How Reese Witherspoon made a $400 million fortune by being the best friend every woman not only wants… but needs

Reese Witherspoon was still in her 30s when she found herself facing that ‘don’t-call-us-we’ll-call-you’ scenario that every actress dreads in Hollywood. Despite garnering praise for her charm and impeccable comic timing in films such as Sweet Home Alabama, and winning an Oscar for her impressive performance as country singer Johnny Cash’s spirited second wife June Carter Cash in Walk The Line, her phone rarely rang with offers.

It was a painful time. To add to the stress, she remembers meeting with a financial adviser who told her to start saving fast, because it was likely she would be making drastically less money in her 40s.

Yet today, still only 47, she is not only a Hollywood power player on and off camera – starring in and producing hit films such as Wild, along with hugely popular TV series like Big Little Lies and The Morning Show – but is also one of America’s most influential business brains.

Millions of women hang on her every word for advice on everything from interior styling to what book to read, which has helped make her very wealthy.

In 2021, Witherspoon sold Hello Sunshine, the production company she co-founded in 2016 and which is responsible for many of her biggest hits, to a media company backed by the private equity fund Blackstone Group Inc for a reported $900 million, making her worth an estimated $400 million.

GIVING WOMEN A VOICE: Witherspoon, left, at the premiere of Daisy Jones & The Six, with stars Riley Keough and Suki Waterhouse

A-LIST: Witherspoon at the Oscars in 2021

How, then, has she achieved such a metamorphosis – and, remarkably, all without a single person in the notoriously catty industry having a bad word to say about her?

Sue Enquist, one of America’s most respected athletic coaches who trained Witherspoon for a role as a former Olympic softball player in the 2010 movie How Do You Know, is rhapsodic when talking of the actress’s qualities.

She might be 5ft 1in but, Enquist tells me, she has ‘the same performance and character skills possessed by perennial Olympic and world champions – strong character and high standards’.

She adds: ‘I can find a thousand people who can win once. But there are very few people who can win and win again over time and are sustainable champions. Reese is one of those people. She has this unwavering desire to be better every day.’

When she was asked to train Witherspoon, no-nonsense Enquist initially questioned whether the actress, known for her quirky charm, would be up for such a mammoth task.

‘She came to it with no skill or experience and really went for it,’ recalls Enquist. ‘She could have done an OK job and the cameras would have made her look good, no matter what. But that wasn’t good enough for Reese.’

Enquist says she came to recognise that the petite actress had the same kind of character traits top athletes have, the ability to ‘recover fast and have a next-play mindset’.

Witherspoon herself has said that when things get rough, she thinks back to the advice Enquist gave her during filming: ‘You’re allowed to have one bad innings, but you’re not allowed to have seven. So give yourself a minute to feel rotten, and then move on.’

No doubt this inner steel and resilience will be coming to the fore at the moment. For Witherspoon has recently announced her divorce from her second husband, Jim Toth, formerly one of the top agents at Hollywood’s Creative Artists Agency.

His love and advice was widely accredited – not least by Witherspoon herself – as a catalyst in her transformation. She paid tribute to him in her 2018 book Whisky In A Teacup, about life in her hometown of Nashville, Tennessee. ‘On our first date, I told you the woman I wanted to be, and your endless support has helped me become that woman,’ she wrote in the credits.

What next, then, for Witherspoon, after the couple announced their split just a few days short of their 12th wedding anniversary?

They have one son, Tennessee, aged ten. Witherspoon also has two older children, Ava, 23, and Deacon, 19, from her first marriage, to the actor Ryan Phillippe.

‘Reese is obviously disappointed and upset. She never saw herself getting another divorce,’ an insider has said.

‘They will continue to co-parent amicably. There is no drama.’

No one should doubt that Witherspoon will bounce back.

In fact, she has admitted that she operates best when under pressure. It was her financial adviser’s original prediction about her future that, she said, ‘put me in a panic state’ and spurred her on.

She later fired that adviser, saying she didn’t need his negativity.

It was during her 12 years of marriage to Toth, 52, that she transformed herself, with his counsel coming firmly to the fore.

She has described how in the early days of their marriage she told him she worried about the standard of roles she was offered. ‘He said, “Are these the movies you want to be making?” And I said, “No, I’m waiting for the scripts to come in.” And he said, “You don’t seem like the kind of person who sits around and waits for the phone to ring, and you read more books than anybody I know, so why don’t you start making them into your own material?” ‘

That led to her optioning the film rights for the chilling psychological thriller Gone Girl by author Gillian Flynn, which she produced, then doing the same with Cheryl Strayed’s bestseller Wild, about a flawed and feisty woman putting her life back together by hiking the Pacific Crest Trail. Witherspoon also starred in Wild, earning another Oscar nomination.

It is key to note the emphasis on women’s authors and stories. Not only is this an immensely marketable sphere, attracting lucrative middle-aged female audiences, but it taps right into Witherspoon’s own dearly held values.

Her dedication to uncovering women’s voices has continued to drive her, and is perhaps particularly evident in Reese’s Book Club, which now has more than 2.5 million members. Inclusion on the list is highly sought after because it sends book sales soaring.

It has helped numerous unknown women authors reach the big time, as well as, handily, providing material for Witherspoon to adapt for film and television.

This includes the series Little Fires Everywhere, based on Celeste Ng’s novel and starring Witherspoon and Kerry Washington; the Amazon TV series Daisy Jones & The Six, starring Riley Keough; and the film Where The Crawdads Sing, starring Daisy Edgar-Jones.

As a debut author, being chosen for Reese’s Book Club felt like ‘winning the lottery’, says Ana Reyes, whose book The House In The Pines was January’s choice.

‘I can’t tell you how much it meant to me that she read The House In The Pines, and not just read it, but loved it.’

Author Nina De Gramont’s novel The Christie Affair, which reimagines Agatha Christie’s unexplained 11-day disappearance that captured the world’s imagination in 1926, was another choice.

She says: ‘Reese is a wonder. I love her guiding principle which is, to quote her, “women’s stories matter, they just matter”.

‘The community she’s created includes readers, the amazing women who work with her and grateful authors like myself.

‘Her support has changed my career. More important, her support of women’s stories has opened up worlds and amplified voices to countless readers who would never have found their favourite books without her.’

Reese Witherspoon (right) alongside Nicole Kidman (centre) and Shailene Woodley (left) in Big Little Lies

Another instance of timely marital advice from Toth came when Witherspoon mused about writing a blog to talk to her 29 million Instagram fans about the Southern-inspired apparel and home goods she loved. Toth suggested she cut to the chase and go into retail on her own.

Her clothing and homewares brand, Draper James, named after her grandparents, now has four stores in the US.

After all this success, surely, you might think, she will have trodden on a few rival toes along the way.

Not so, it seems.

A staunch believer in women collaborating, when she found that Nicole Kidman had optioned the rights to author Liane Moriarty’s book Big Little Lies, she suggested they team up.

The series has won multiple Emmys and Golden Globes for its cast, which includes the pair.

Similarly, Witherspoon starred in and executive-produced Apple TV’s wildly popular The Morning Show, alongside Jennifer Aniston.

It seems that she practises what she preaches. A champion of women’s rights in the film industry, she has demanded that actresses are paid the same rates as actors.

This has had discernible impacts on the prospects of women in Hollywood, as she recounted when discussing how, in 2018, as a founding member of Time’s Up, the organisation founded by Hollywood celebrities in response to the sexual crimes of producer Harvey Weinstein, she also helped shape new fair-pay policies at the television behemoth HBO, where she worked on Big Little Lies.

‘An actress came up to me at a party and said, “Do you know what you’ve done?” ‘ she recalled. ‘I had no idea what she was talking about. The day after the HBO equal pay thing went through, they called her agent to rewrite her contract. She was then paid twice as much as she had been.’

Reese Witherspoon (left) and Jim Toth (right) attend the Girls Inc. Los Angeles Celebration Luncheon at The Beverly Hilton Hotel in November 2016

It’s this real-life dedication to the sisterhood that Witherspoon’s enamoured fanbase find so appealing. Little wonder they hang on to her every recommendation, and spend their hard-earned money with her guidance, as Lauren Brown West-Rosenthal, author of Reese Witherspoon: The Biography, tells me.

‘Reese’s best quality is that she comes across as the best friend every woman not only wants – but needs,’ she says.

‘She’s the friend who will tell you that your outfit isn’t working, to dump the guy that isn’t treating you right, or offer up tough love that no one else would say to your face.

‘It’s also her confidence and intelligence that shine through in everything she takes on – from movie roles to business deals.

‘Her taste is impeccable, and she’s done extraordinary things in her career while staying true to the girl she was way before making Hollywood’s A-List.’

While married, Witherspoon and Toth have been as private as it’s possible to be in the goldfish bowl of Hollywood, but rumours had been circulating that the pair were growing apart.

Toth remains a founder member of the boards of Hello Sunshine and clothing store Draper James.

The sale of Hello Sunshine made the couple extremely rich, and sources have suggested that this huge influx of cash – and the fact that Witherspoon is still committed to her career while Toth wants a quieter life – is one of the reasons for the split.

Though they will still work together on some level, reports say they have been carefully disentangling their financial affairs in the run-up to their divorce, and their relationship is amicable.

A mark of the universal fondness for the petite blonde actress is the fact that everyone seems to be rooting for her as she navigates a new life post-divorce.

‘Reese can do no wrong in all the choices she makes for herself personally and professionally because she handles it all with grace, class and respect,’ comments Brown West-Rosenthal. ‘It’s a rare combination in Hollywood but ensures she’ll be well loved and revered now and in the future.’

As she moves on post-divorce, she can be sure the army of women – both famous and unknown – who she’s supported will now be wholeheartedly trying to support her.

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