2021 TIME100 Most Influential Companies
April 27, 2021 6:18 AM EDT

It’s about 12 minutes into the Q&A when Reese Witherspoon starts to cry. “A long time ago, people drew some lines on this world,” she says, reflecting on families separated by immigration policy. “We are just part of a common humanity.”

She’s talking to Patricia Engel, the author of Infinite Country, for a Reese’s Book Club event in front of a Zoom audience of publishing professionals, influencers and readers. “I didn’t think I was going to get emotional,” she tells the far-flung crowd, likewise moved by Engel’s story of a family divided between Colombia and the U.S. “You’re not the only one who cried, Reese,” someone writes in the chat. And later: “This story needs to be made into a movie.”

That’s the exact sentiment that drives Witherspoon, 45, who has transformed her role in Hollywood from movie star to business leader—and maker of her own fortune. After rising as a child actor, she shot to household-name status for 2001’s Legally Blonde, going on to win an Oscar in 2006 for Walk the Line. But even after those triumphs, for a time she struggled to find satisfying roles in Hollywood, where women’s stories have long been sidelined. She discovered a way to change that in a lifelong love: books. Celebrating books through her book club—and adapting them for the screen—is now the foundation of Witherspoon’s business at Hello Sunshine, the media company she founded in 2016, where she’s established a track record for spotting, and making, hits.

At Hello Sunshine, Witherspoon picks titles for the book club. Of the 54 selections to date, often titles that hit a sweet spot between commercial and literary, more than 30 have gone on to make the New York Times best-seller list, making a tap from Witherspoon one of the most coveted accolades in publishing. And her executives have built a machine around accessing intellectual property and swooping in on screen rights, evaluating more than 1,000 books, articles, original scripts, pitches and life-rights documents each year. The company has produced buzzy series based on books like Big Little Lies and Little Fires Everywhere, which was also a Reese’s Book Club pick, and has a number of titles on option.

Before Hello Sunshine, Witherspoon ran another company, Pacific Standard, which produced Gone Girl, Wild and the first season of Big Little Lies, all based on books. But Witherspoon had invested her own funds to get that company off the ground, and it wasn’t enough, even after those hits. So she began looking beyond Hollywood. “I didn’t have money to pay for all the employees, plus benefits, and keeping the lights on in an office,” she says. “I started thinking, How could I make this into a bigger, farther-reaching, scalable endeavor?” She looked for partners, finding a backer and eventually her CEO at Otter Media, a joint venture between AT&T and the Chernin Group.

It’s a common practice for actors to build production companies around creating work for themselves. And celebrity-led book clubs—from Emma Roberts’ Belletrist to Kaia Gerber’s Instagram discussions to Oprah’s original—abound. What sets Hello Sunshine apart is the power created by combining the two pursuits, and the breadth of its ambition. Witherspoon doesn’t want to run a vanity shingle—she wants to build a media empire. What started as a direct response to the dearth of compelling roles has grown into a 70-person, multi-platform company. It has four productions currently shooting: Truth Be Told, From Scratch and The Morning Show in Los Angeles, and Where the Crawdads Sing in New Orleans. And Hello Sunshine now also has divisions focused on unscripted TV, kids and animation projects, podcasts, digital series and social media endeavors like an app for the book club. The company expects to be both profitable and cash-flow-positive for the first time this year.

In a crowded content landscape, Hello Sunshine has a clear directive: to create work that centers women, showcasing their agency and offering a glimmer of hope. The challenge is honing that goal, and living up to its full potential, in a world where the standards for equity and diversity continue to evolve. The once revolutionary premise of centering women, which so often means white women, is no longer enough. Achieving true equity means constantly examining biases and pushing to do better. “It’s embedded in our mission,” CEO Sarah Harden says. “This isn’t about changing the world for white women. It’s elevating intersectional voices.”

Recently, a friend of Witherspoon’s—and the author of a Reese’s Book Club pick—texted the actor a photo of a house. She had just become the first homeowner in her family, thanks to her book sales. It was a big moment for Witherspoon, who declares a personal goal: “I want to make a lot of women a lot of money.”

That feminist perspective shows up throughout our two-hour Zoom conversation in March, Witherspoon calling in from a vacation with her family in the Caribbean. She’s frank about the meaning of money, and the meaning of power, in an industry that has so long denied women both.

Witherspoon, pulled like so many viewers to the narrative of exploitation put forth in the New York Times Presents documentary episode “Framing Britney Spears,” draws comparisons to her own story as a young woman in the tabloid spotlight of the early 2000s. She got divorced the same year Spears did; each was raising two kids under the relentless eye of paparazzi, sometimes chased by the same photographers. Witherspoon was followed to church, to school, to soccer practice; there was a period of time when an RV was parked outside her home, cameras pointing into her kitchen window every hour of every day. “My children will tell you stories about being in preschool and people climbing on the roofs of our cars,” she says. In 2006, she moved the family home to Nashville.

For all that, Witherspoon considers herself one of the lucky ones. She’s clear-eyed about the fact that women like Spears, Paris Hilton and Lindsay Lohan were considered “bad,” while women like herself and her friend Jennifer Garner were “good.” She recalls all the times she was filmed screaming at the cameras, which never stuck to her reputation as they did to other famous women. “What if the media had decided I was something else? I would be in a totally different position,” she says. “I want to say it’s my decisions or the career choices I made, but it felt very arbitrary. And kind of sh-tty.”

Much more deliberate was the wave of empowerment for women in Hollywood that came with the #MeToo movement in 2017. Witherspoon came forward, sharing that she had been sexually assaulted by a director when she was 16 years old, and that she’d suffered other incidents of abuse as well. The end of 2017, she says, was a difficult time—she hardly slept, struggled with anxiety, contended with memories that she had long closed off. And while she has chosen not to name her abusers, Witherspoon says she has been able to speak with the people who were responsible for her safety yet failed to protect her. The most healing part, she says, was finding herself in rooms with other women who could relate, and who were driven to make change.

There was the night with Rashida Jones, Kerry Washington and America Ferrera in Eva Longoria’s living room, when Witherspoon cried and lamented that they wouldn’t be able to force others to act. Ferrera looked at her with intensity and said, “Yes, we are.” There was the secret initiative that Witherspoon will speak only vaguely about—“One day I’ll tell you what happened”—where she says Shonda Rhimes put her up to calling 30 business leaders in Hollywood who had no women or people of color on their boards. “There was something about Shonda believing that I could,” she says. “I was proud of myself.” And there’s the group text. “Whenever I feel discouraged, I have a group of women. We all text each other, and we’re like: Just keep going.

Witherspoon likens Hollywood to a giant cruise ship, which she tries to steer, painstaking degree by painstaking degree, in a better direction. As she says this, she gestures her hands as if she’s scooting a toddler toward his first steps, smiling and offering words of encouragement. “Come on, you can do it,” she says.

The move is very Elle Woods, that perpetual optimist Witherspoon is still best known for playing. The character, like Witherspoon, will have entered her 40s if and when Hello Sunshine eventually produces a third Legally Blonde movie. I ask Witherspoon what Elle is doing now, and she thinks a moment before conjuring the image: “She’s hitting barriers and obstacles that she never thought she’d be hitting later in life,” she says. “She reminds me of the woman at the Women’s March, holding the sign that says, I’M STILL DOING THIS SH-T.”

How do we do better? That’s a question at the heart of Hello Sunshine’s work, and one many companies have focused on since George Floyd’s murder set off a tidal wave of protests last May. The reckoning with racial injustice has changed the conversation about the distribution of power in institutions across the U.S. The leaders of Hello Sunshine—like the leaders of any organization with a hope of meeting society’s demands for change—understand that the work of equity is never finished.

Hello Sunshine’s COO Liz Jenkins remembers struggling through the weekend last summer when protests first surged and logging on for work that Monday. In a team meeting, she decided in the moment to be honest about how she was hurting as a Black woman. “I thought to myself, as I took a deep breath, ‘No. I’m not going to pretend that everything is O.K.,’” she says.

Harden tears up when she remembers the impact Jenkins had that day, and the letter she wrote to the staff in place of the CEO’s typical weekly note. “It helped create the room for others to not be O.K., and to listen and recognize the importance of active allyship,” she says. As is the case for so many companies, the dialogue about diversity and inclusion at Hello Sunshine can be tough. “Are there sometimes uncomfortable conversations? Of course,” Jenkins says. “But if we don’t have those conversations, everybody’s going to keep getting canceled, nobody’s going to grow, and there’s not going to be real change.”

That attitude shows up in the work that Hello Sunshine produces. The executives describe a commitment to creating opportunities for people of all backgrounds on their productions, and hold up their 2020 Hulu series, Little Fires Everywhere, as the embodiment of the Hello Sunshine ideals: they started with a powerful book about motherhood by Celeste Ng, found a like-minded collaborator in Washington and her production company Simpson Street, and hired writers who could connect with the material in different ways.

Witherspoon and her president of film and television Lauren Neustadter had the idea to cast Washington in the role of Mia, a single mother who is white in the book and spars with Witherspoon’s Elena. Washington likens Elena to “the archetypal Karen” and calls her co-star “brave” for embracing the character. “Reese was stepping into the role of this privileged white woman who imagined herself woke but had a lot more work to do,” Washington says. “She had to put a very real soul and humanity in that person.”

Those choices—and in particular, the decision to cast Washington and run straight at issues of racial tension—reimagined the story “in exactly the way that I would hope,” Ng says. Neustadter is moved to tears as she describes the pride the team felt to have Ng’s approval of the final product. “It was so important to us to do right by her,” she says.

But doing better also means acknowledging shortcomings, even within the most well-intentioned, values-oriented institutions. While Hello Sunshine’s leaders strive to tell inclusive stories, they have only one person of color on their executive team. And when it comes to the authors who have so far benefited the most from Hello Sunshine’s work, the majority are white women. Roughly two-thirds of the book-club picks have been by white women (even more by straight women), with a notable focus on Black authors last summer. “I feel like it’s a step in a process, and hopefully not the last step,” says Ng, who was excited to see Nancy Jooyoun Kim’s The Last Story of Mina Lee selected last fall.

Photograph by JUCO for TIME

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For productions based on IP by white writers, which represents the majority of Hello Sunshine’s slate, Neustadter asserts a “responsibility to expand the scope of the story.” She cites the example of the Apple TV+ show Truth Be Told, which they adapted from Kathleen Barber’s novel Are You Sleeping to create a role for Octavia Spencer, who co-produced the show, with Nichelle Tramble Spellman showrunning. “It’s a gigantic part of our initiative to have women of color writing, adapting and directing the stories,” Witherspoon says. But she adds that she’ll often share material to review with other women; Freida Pinto is adapting a former Reese’s Book Club pick. “If we don’t feel like it’s going to be authentically told, we don’t know if we’re the right company to tell it,” Witherspoon says.

As a next step toward amplifying new voices, the company is preparing to launch LitUp, an initiative designed to override some of the systemic inequities in publishing. The program, open to women from a list of underrepresented backgrounds, will aim to foster the careers of 25 new authors over the next five years. For the first round, Hello Sunshine will select five writers who each have a manuscript at the ready but have not secured representation, a crucial step on the path to publication, and offer them access to a network of more than 50 agents, an all-expenses-paid writers’ retreat and a mentor from its pool of former book-club authors. Part of the deal, designed to give new authors a boost in the process of selling their books to publishers, is a marketing commitment from Hello Sunshine.

“I know there are worthy stories sitting out there by underrepresented voices that haven’t been able to get through the structural gatekeepers,” Harden says. She’s expecting thousands of submissions, which will go through multiple rounds of blind reads in an anti-bias process designed by Hello Sunshine’s partner, We Need Diverse Books. Witherspoon will join in the later rounds of reading applications, and the company aims to select its first class of LitUp fellows by the end of the year.

Witherspoon acknowledges the need for her business to evolve on matters of equity and representation, whether through starting new programs like LitUp or honing existing ones. And her company isn’t the only one. During our interview, she begins to describe a demeaning photo-illustration of her that ran in a magazine in 2015, when she launched her fashion company Draper James; it was this magazine, but I’m not sure she would have said so if I hadn’t owned it first.

The art depicted her and four other celebrity women who had started businesses holding baked goods, toting cleaning supplies and wearing aprons. The sexism of the image, and its place in TIME, has bothered her for years, and she tells me about the conversations she had then with Gwyneth Paltrow and Jessica Alba, who were also pictured. Together, they decided they would speak about it in the future, when the world was ready to hear it. I offer an apology. We are accountable too.

“Culture shifts,” Witherspoon says. “Culture changes.” She’s talking about our mistake, but also so much more. “Once you know better, you do better. We have to make room for that.”

Cover photo: Dress: Emilia Wickstead, Belt: Alexander McQueen; Blazer: Gabriela Hearst; Shoes: Celine; Hoops, watch, and rings: Cartier

Inside: Suit and belt: Alexander McQueen; Shoes: Saint Laurent, Earrings and rings: Cartier

Write to Lucy Feldman at lucy.feldman@time.com.

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