Until the late 20th-century, woman faced enormous challenges if they dared to run or start a company. Meet a few who did.

Mary Katharine Goddard

Her Revolutionary Newspaper Gave Real Meaning to "Publish or Perish"

Between prison stints, the canny but less-than-dependable William Goddard handed his newish newspaper over to his older sister, Mary. The year was 1774, and Mary, most likely the colonies' only woman newspaper publisher, wasted no time in giving the British what for, even printing Common Sense, Thomas Paine's pro-revolutionary treatise. Mary was later named Baltimore postmaster, likely making her the first female federal employee.

But Mary's knee to the establishment's groin did not stop there: When it came time to print that doc we call the Declaration of Independence, Congress turned to Mary--and she obliged, becoming the only woman whose name graces it: "Baltimore, in Maryland: Printed by Mary Katharine Goddard."

Madam C.J. Walker

She Discovered the Beauty of Black Enterprise

Starting a business is tough enough, but imagine doing so under these conditions: Your sharecropper parents had once been enslaved; you were orphaned at 7 and widowed at 20; and, oh, yeah, you're also a single mother. It'd be enough to make your hair fall out--which is what happened to pioneering entrepreneur Madam C.J. Walker, who in 1905 promptly invented her own hair care products for Black women. Making over the Black hair care industry made Walker a millionaire, the country's first Black woman to achieve that distinction.

Beyond the products themselves (including the named-without-nonsense Wonderful Hair Grower), Walker employed Black women--who, in the early 1900s, didn't have many job prospects--to sell the products door-to-door. Walker shrewdly relocated her business from Denver to Indi­anapolis, because the latter had both a sizable Black community and was serviced by railroads, making product distribution a snap. Walker was so ahead of her time on women's empower­ment that her firm's charter stated that only a woman could serve as president of the company.

Brownie Wise

The Party Starter Who Made Plastic Fantastic

Today, when women routinely apply ice picks to glass ceilings and lead high-flying global companies, selling Tupperware might seem, well, agonizingly domestic. Invented by plastics man Earl Tupper in 1946, Tupperware was initially considered too high-tech and unfamiliar to sell in department stores; despite its catchy colors and whiz-bang double-seal, the product simply wasn't moving.

Enter Brownie Wise, a divorced mom, who, in the late 1940s, pioneered the home-based, woman-focused Tupperware-party method of selling. Her rah-rah parties included games, sales incentives, and ample servings of self-help talk. They were effective--viral, even--and quickly made Tupperware a household name. Wise rose from salesperson to a vice president--an almost unfathomable position for a woman in 1951.

In three years, she built a Tupperware army of 20,000 sellers, while revenue hit what would be about $250 million in today's dollars. She gained fame as the first woman to appear on the cover of Business Week--but maybe too much fame for Tupper. The two tangled, and, in 1958, shortly before he sold the firm, he kicked her to the curb.

Elizabeth Arden

Her Business Makeover Launched an Industry

Florence Nightingale Graham turned a neat trick: In the early 1900s, she found a way to take makeup--at the time used primarily by prostitutes--and market it to middle-aged women. By 1910, she'd outgrown her kitchen-slash-laboratory and plunked down a hefty $1,000 to open her first salon on Manhattan's Fifth Avenue with her business partner, Elizabeth Hubbard. Four years later, the partnership fizzled and Graham created a nom d'entrepre­neur for her salon and herself: Elizabeth Arden. From there, Arden innovated like crazy, applying a scientific approach to the products themselves and a wildly inventive tack in her marketing. Among her many firsts: She introduced eye makeup to American women; created in-store makeovers; concocted travel-size beauty products; and was the first to create (color-coordinated!) makeup for women in the military.

Serena Williams

A Champion at the Net Who Scores as a Investor

Yes, she's won more Grand Slam singles titles than any other player--man or woman--in the modern era. (Twenty-three, if you're counting at home.) Yes, she's held the No. 1 spot in women's tennis for a combined 6.1 years. And, yes, along the way, she's pocketed about twice as much prize money as any other woman athlete ever. But Serena Williams has also expertly leveraged her on-the-court dominance into entrepreneurial winners, turning herself into a sought-after global brand.

Like any superstar, she's done a ton of endorse­ments. Williams, though, has started new businesses (her own fashion lines) and, through her Serena Ventures, she's looked around corners, investing in dozens of startups, from crypto­currency trackers to plant-based burgers and NFTs. She's also into football--both the global kind, as part owner of a new women's soccer franchise in Los Angeles, and the American version, having an ownership interest in the NFL's Miami Dolphins.