In the span of ten days, America lost two of its most beloved icons: Dolly Parton on August 25, and Gloria Steinem on September 2.

Their deaths were mourned as a single story , though an odd pairing to some at first glance.

On the surface, they could not have been less alike — the rhinestoned country superstar from a one-room cabin in the Smokies, and the aviator-glassed journalist who became the face of the women’s movement. But read their lives side by side and a different pattern emerges.

Dolly Parton and Gloria Steinem were two of the most disciplined entrepreneurs of the last century.

Lesson 1: Leave The Platform That Made You, At The Right Moment

Let’s start with the exits. In 1974, Parton walked away from The Porter Wagoner Show — the platform and eponymous creative force that had made her a star — to build her own career. The song she wrote as her resignation letter was “I Will Always Love You.” She had promised five years and stayed seven, on a show where Wagoner controlled the format, the producing, and a web of shared royalties and business interests. Her paycheck never moved — he answered her requests for a raise with necklaces and Cadillacs. “I don’t want the gifts,” she recalled telling him. “I want the money.” Leaving cost her dearly — Wagoner later sued her — but she understood that the platform’s terms had become the ceiling on her career.

Steinem’s version came earlier: as a freelance writer in a media industry that assigned women the fashion pages, she stopped waiting for a seat at existing publications and started building her own. She used her founding editorship at New York Magazine — the platform she’d helped build — to launch Ms. inside its very pages in December 1971, then left to run the magazine that was hers.

Both understood something founders relearn every generation: you cannot build the thing that matters while renting space in someone else’s vision.

Lesson 2: Own What You Create

Parton controlled her publishing from the start , through her own publishing companies — beginning with Owe-Par, which she co-founded in 1966 at age 20, holding the controlling interest. It is difficult to overstate how unusual this was: a 20-year-old woman in 1966 Nashville keeping a controlling stake in her own copyrights, in an industry built on artists signing theirs away. Half a century later, the biggest stars in music were still fighting for what Parton secured at the start — Taylor Swift spent years re-recording four entire albums to wrest back control of her catalog before finally buying her masters outright in 2025, and Prince performed with “slave” written on his cheek over the same fight.

In 1974, when Elvis Presley wanted to record “I Will Always Love You,” his manager called the day before the session with a condition: Elvis got half the publishing. She said no — to Elvis — and cried all night. “These are my songs,” she later said. “They’re like my children, and I expect them to support me when I’m old.” Eighteen years later, Whitney Houston’s cover spent fourteen weeks at number one, and the royalties came home to Parton. She went further in 1995 , releasing her music through her own label — first Blue Eye Records, later Dolly Records — paying for her own sessions and leasing the recordings out on terms that returned the masters to her. Every artist now fighting to own their masters is running Dolly’s playbook.

Steinem’s ownership story is about institutions rather than copyrights, but the instinct is identical. When advertisers insisted no woman would buy a magazine without recipes, she and her co-founders launched Ms. anyway — shrewdly, as an insert inside New York Magazine , using someone else’s distribution to prove demand before building their own. The preview issue sold out on newsstands in days. She went on to co-found the National Women’s Political Caucus, the Women’s Action Alliance, the Ms. Foundation for Women, and — at 71 — the Women’s Media Center.

Parton built Dollywood as a jobs engine for the mountains she came from, and the Imagination Library , which has mailed more than 332 million books to children since 1995 . Neither woman was building for an exit. They were building things designed to outlast themselves.

Lesson 3: Let Them Underestimate You — & Use It As An Advantage

Both also turned being underestimated into an operating advantage. Parton leaned into the caricature, while negotiating like the shrewdest dealmaker in Nashville: “I’m not offended by all the dumb blonde jokes because I know I’m not dumb,” she famously said, “and I’m not blonde either” ; and the lesser known: “I always understood guys would want to look at my boobs. I would say in a business meeting, ‘I’ll give you a minute to look at these, but then I want you to listen to what I have to say, because I’m here to make money for all of us.’” .

I always understood guys would want to look at my boobs. I would say in a business meeting, ‘I’ll give you a minute to look at these, but then I want you to listen to what I have to say, because I’m here to make money for all of us.’ Dolly Parton

Steinem saw this before almost anyone. In January 1987, she put Parton on the cover of Ms. as one of its Women of the Year, beside a senator and a novelist and a nun who sheltered refugees, and wrote that anyone who hadn’t listened to Dolly Parton or to feminism might be surprised to learn they went together. “If feminism means each of us finding our unique power, and helping other women do the same,” Steinem wrote, “Dolly Parton certainly has done both.”

Consider what Parton did with her power in her own songwriting. “Jolene,” written in 1973, is a woman addressing her romantic rival directly — and it contains not a single unkind word about her. The narrator calls Jolene beautiful, envies her hair and her eyes, and asks rather than demands. Half a century on, it remains one of the only songs by a woman about the woman who threatens her that refuses to make her the villain; the biggest female pop artists were still writing “Better Than Revenge” (Taylor Swift) and “ Becky with the good hair” (“Sorry,” Beyoncé) decades later. It may be the most quietly feminist song in the American catalogue — written by a woman who spent the next fifty years declining the word.

Parton never returned the feminist embrace , at least not in public. Asked directly in 2019 whether she thought of herself as a feminist, Parton said no; she had too many fans on both sides of the fence.

Steinem judged the work, not the label, in her 1987 tribute — and the work was a woman who had taken every devalued symbol of femininity and turned it to her own ends.

Steinem herself knew the same trick; her beauty and glamour were used constantly to dismiss her, but she used the attention it drew to put unglamorous issues on the front page.

Every founder who has ever been talked down to in a boardroom — and every woman founder has — knows this move: let them underestimate you. Being underestimated is a free advantage; take it.

Lesson 4: Build For A Long-Term Horizon

The last lesson is about time horizons. I met Steinem several times over the years , beginning as a student at Wellesley in 1997. On a Zoom call a few years ago, as the fall of Roe v. Wade loomed and the women on the call were despairing, someone asked her how to stay optimistic when the world seemed to be moving backwards. She put us in our places. The law had been wrong for most of her life, she reminded us: she grew up under segregation, had to travel to another country to access an abortion, and could not have opened her own bank account until well into adulthood. Progress takes time, she said. Keep fighting.

Parton would have nodded. She held onto a song for eighteen years before it made her fortune. Steinem worked at the same cause for sixty. Both operated on horizons no venture fund would underwrite, and both compounded accordingly — one in copyrights, the other in altered defaults: the Ms. honorific on every form, the books arriving in the mail, the assumption that a woman can own the stage, the song, and the company.

They never called themselves entrepreneurs. But between them, they wrote the best founder’s curriculum we have: leave the platform that constrains you, own what you create, let them underestimate you, and build things designed to outlive you. Class dismissed.