Makin’ Money Moves: Lessons from Four Trailblazing Black Women Entrepreneurs

We've been talking about capitalism a great deal lately: boycotts and buy-nothing days being among the enduring forms of dissent that we collectively possess. Given how motivated the "powers that be" (from business to government) are about money and power, and their (frankly) shocking acquiescence to the "throne," many of us feel disappointed, and abandoned as consumers, or just simply humans engaging with "brands." In this light, managing our personal and communal finances is not just participation in the marketplace—it's actually a powerful form of activism.

Over the centuries, our society has bestowed disproportional praise upon the rich, oftentimes to the detriment of everyone else. In shining a light on these four women moguls, it is not their wealth I wish to celebrate, but rather what they did with their money: the influence and benefit they brought to their communities, and also the representational value of their business ascent. In eras where they did not possess the right to vote. Never forget women were given the right to vote in 1920, but that was white women; Black women could not vote until the Voting Rights Act of 1965. Today, we see an effort from these so-called "powers" to restrict that law. Stay vigilant.

Looking at the past, Madam CJ Walker, Mary Ellen Pleasant, Biddy Mason, and Maggie Lena Walker symbolize our collective climb out of subjugation and towards a more empowering future. They stared down overt hostility, economic exclusion, and many attempts by the broader power leaders to squash their ambition. And yet—they persevered, built, sheltered, organized, and funded new possibilities for themselves and for all who followed. We thank them!

What Madam CJ Walker, Mary Ellen Pleasant, Biddy Mason, and Maggie Lena Walker Can Teach Us About Making Money and Using it for the Greater Good

I don't celebrate these women just because they became rich, but because, more importantly, they exemplify the concept that true wealth is making a community thrive. Let's learn more about them.

Madam C.J. Walker: Black Hair Pioneer, Self-Made Millionaire - December 23, 1867 – May 25, 1919

Black Hair Pioneer, Self-Made Millionaire (December 23, 1867-May 25, 1919)

Because of the dominance of European features as the standard for beauty and worthiness, Black women faced intense pressure—socially, culturally, and economically—to emulate the silken hairstyles of white women. This convention carried on through the centuries.

In the face of this inequity, Sarah Breedlove, known later as Madam C.J. Walker, saw both a need and an opportunity. Through trial, error, and diligence, she developed the Walker System, a line of shampoos, scalp ointments, growth lotions, and heated combs that gave Black women that sought-after “processed look.”

The success of her products not only brought joy and confidence to countless Black women but also made Madam Walker the first self-made Black woman millionaire in the U.S.—rewriting the rules of race and gender, and, through a beauty empire anchored in the fulfillment of Black women, portending the symbolic and real significance of the Black dollar.

Born Sarah Breedlove in 1867 to formerly enslaved parents, she was orphaned by age seven and sent to live with her sister. She married at fourteen to escape poverty and abuse, became a mother by seventeen, and was widowed by twenty, left with a toddler to care for on her own. She moved to St. Louis, Missouri, where she worked for nearly twenty years as a laundress—the only work open to Black women—scrubbing clothes for little pay, and later as a saleswoman for another hair product entrepreneur (and rival).

The agony of her own stress-induced hair loss prompted her to experiment with remedies. By 1905, settled in Denver and having learned basic chemistry, she created “Madam C.J. Walker’s Wonderful Hair Grower,” launching her enterprise with less than two dollars in her pocket. She used her third husband’s name, Charles Joseph Walker, as her brand moniker. Staving off competition and keenly determined, she turned her own struggle with hair loss into what would become a global beauty business—today the Black haircare industry is a $10 billion global affair—and her fiercely loyal customer base was a precursor to today’s “Buy Black” movements.

Starting with door-to-door sales and advertisements in the Black press, Walker built a nationwide business, expanding to mail-order distribution and franchised sales agents. In 1910, newly divorced, she constructed a factory in Indianapolis and soon reached international markets—including Central America, the Caribbean, and a glamorous Harlem salon managed by her daughter. At the height of her success in the late 1910s, her net worth ranged between one and two million dollars, equivalent to roughly 18–36 million USD today.

Later in life, Walker edged her way into the upper crust, building an estate, Villa Lewaro, in Irvington-on-Hudson, a hamlet in Westchester County, New York, designed by a Black architect—home to some of America’s wealthiest industrial families, including the Vanderbilts, Morgans, Astors, and notably John D. Rockefeller, whose mansion was just a few miles down the road.

Madam C.J. Walker believed in using her success to benefit others. Her philanthropy helped fund the YWCA, the NAACP, and multiple historically Black schools and colleges—especially meaningful for her as someone denied a formal education.

Yet amid this acclaim, Walker faced the persistent barriers of race and gender. In 1917, she joined Harlem leaders seeking President Woodrow Wilson’s support for Black veterans and anti-lynching legislation; he declined to meet with them.

She also frequently clashed with Booker T. Washington, who resisted her prominence and the beauty standards she promoted. At a 1912 National Negro Business League conference, Washington tried to sideline her, but Walker spoke up: “Surely, you are not going to shut the door in my face. I feel that I am in business that is a credit to the womanhood of our race.” The next year, she headlined the conference—yes, she did the thing!

Not bad for a girl born on a Louisiana plantation, two years after Emancipation!

Reflection: How do you define success—and who benefits from it?

Mary Ellen Pleasant: The Harriet Tubman of California - August 19, 1814 – January 4, 1904

Mary Ellen Pleasant’s early life remains shrouded in mystery, but we do know that as a child, she ended up living in the home of a Nantucket, Massachusetts, abolitionist Quaker family as an indentured servant (how one can be both an abolitionist and still have an indentured servant escapes my reasoning…).

Outspoken, and exceptionally observant, she learned household management and business skills while absorbing the family’s deep belief in human equality. As a young woman, she married James Smith, a prosperous merchant who shared her abolitionist ideals. When he died, Mary Ellen inherited a considerable sum—capital she would later convert into both financial independence and fuel for liberation.

After Smith’s death, she moved to San Francisco in 1852 (she purportedly stopped along the way to apprentice with Marie Laveau, “The Voodoo Queen of New Orleans). In San Francisco, she lived a double life—passing as white to navigate white-dominated commerce while quietly building one of the most effective abolitionist networks in the West. She extended the Underground Railroad to California, sheltering fugitives like Archy Lee and funding the movement for civil rights.

Wealthy and strategic, Pleasant (she had remarried since then, though Mr. Pleasant figured little in her life and eventually faded from public record) opened laundries, restaurants, and boarding houses catering to elite Gold Rush clientele.

With her business partner, Thomas Bell, she amassed a joint fortune worth millions by modern standards. She designed and built a grand 30-room mansion at 1661 Octavia Street in the Nob Hill neighborhood, where she lived alongside Bell, the wife she allegedly handpicked for him, Teresa, and the Bell children.

Mary Ellen’s avid support for Emancipation crested in 1859, when she secretly financed John Brown’s failed raid on Harpers Ferry, a bold act that nearly cost her life.

Around 1865, as the Civil War ended, Pleasant “came out” as a Black woman, an act that rapidly degraded her social standing. Rumors spread that Pleasant and Bell were secret lovers and that “Mammy Pleasant” (her new nickname, foisted upon her by the local press) practiced voodoo or ran illicit gatherings in the home. After Bell’s accidental death in 1892, his widow Teresa accused Mary Ellen of manipulating her husband and stealing their wealth. Legal battles over intertwined finances drained Pleasant’s resources, and the courts awarded most assets to Teresa.

Once one of California’s richest women, Pleasant was forced out of her mansion in 1899 and died nearly penniless in 1904.

Despite her unfortunate demise, we remember her today for her enterprising mind and willingness to operate from society’s margins, becoming one of the richest and most influential women in California in her time.

She should also be remembered as a forerunner to Rosa Parks; Pleasant won a landmark California Supreme Court case in 1868 that outlawed racial discrimination on streetcars. She also built community organizations, funded press outlets, and provided housing and employment to freed and free Black residents.

Mary Ellen Pleasant’s tombstone bears the words she requested: “She was a friend of John Brown.” A street and a park in San Francisco’s posh Nob Hill neighborhood are named in her honor. Frustratingly, Mary Ellen Pleasant Park is the smallest public park in the city—a small plaque and six eucalyptus trees. Still, I’ve gone there to pay her tribute and if you visit or live in the Bay Area, you might want to do so as well.

Reflection: How do you work the system from the shadows?

Bridget "Biddy" Mason: From Enslavement to Philanthropy (August 15, 1818-January 15, 1891)

Bridget “Biddy” Mason was born into slavery in Georgia in 1818. As a child, she was separated from her mother, sold and resold among white families, and eventually given as a wedding gift to Robert Marion Smith, a plantation owner in Mississippi. With no rights and no claim to her own children, her life was shaped from the start by forced migration and loss. Skilled in livestock tending, herbal medicine, and midwifery—knowledge passed down from other enslaved women—Biddy became invaluable to the Smith household.

When the Smiths converted to the Church of Jesus Christ of Latter-Day Saints in 1847, Biddy was forced to accompany them on a grueling 1,700-mile trek from Mississippi to the Utah Territory. Prohibited from riding in the wagon, she walked every step alongside it, tending livestock and small children, and still cooking, cleaning, and laundering for the party, while enduring extreme weather, hunger, and exhaustion.

Though slavery was discouraged in Utah, it was still legal, and so Biddy and her children remained enslaved. In 1851, Smith relocated again—this time to California, a free state. As she grew more connected to the free Black community there, she began to learn she was entitled to be a free woman, but for a time she continued to live in servitude, walking an additional 400 miles to San Bernardino.

By 1855, Smith feared losing his “property” and plotted to smuggle Biddy and her family to Texas, where slavery was still legal and she would have been re-enslaved under the Fugitive Slave Act. Friends in the Free Black community learned of his vile plan and alerted the authorities, culminating in a dramatic scene in the craggy Santa Monica mountains, where a band of Black cowboys (vaqueros) and the sheriff rescued the family from the spot where Smith had been hiding them.

After a highly publicized court case in Los Angeles, Judge Benjamin Hayes ruled on January 21, 1856, that Biddy Mason and thirteen members of her extended family were free—making her one of the first Black women to win such a suit in California.

Biddy adopted the surname “Mason” (in tribute to Amason Lyman, a Mormon mayor of San Bernardino) and remained in Los Angeles, where she found work as a midwife and nurse, delivering hundreds of Los Angeleno babies regardless of race or class. She risked her life caring for the sick and incarcerated during smallpox outbreaks, and arranged grocery credit to support flood victims. Consolidating her savings, she began buying land in what would become First African Methodist Episcopal (FAME) Church in 1872—L.A.’s first Black church and the oldest A.M.E. congregation in the city—donating the land on which it still stands.

As one of the first Black women to own property in Los Angeles, Mason reinvested these holdings, worth approximately $300,000 (7.4 million in today’s dollars), to benefit her Black community: establishing a travelers’ aid center, supporting an orphanage, and creating one of the city’s first daycare and elementary schools for Black children. Through her generosity, Biddy Mason became known as a benefactor to the poor, the incarcerated, and the unhoused, and by the time of her death, she had accumulated an estate valued at roughly $6 million today. She is memorialized in Los Angeles for her valor and legacy of healing, perseverance, and service.

Reflection: How do you define freedom—and what are you doing with it?

Maggie Lena Walker: Banker, Organizer & Visionary of Collective Wealth - July 15, 1864-December 15, 1934

Born in Richmond, Virginia, to a Black laundress and a formerly enslaved man during the final months of the Civil War, Maggie Lena Walker grew up amid the harsh uncertainties of Reconstruction, with menial labor and entrenched racial inequality the backdrop to her early days. Her mother worked as a laundress, and young Maggie helped keep the household afloat by delivering clean clothes by hand to white families. After her stepfather’s mysterious death, she took on new financial duties, but never lost her hunger for education.

After attending the Richmond Colored Normal School, she became a teacher, and soon—at just fourteen years old—joined the Independent Order of St. Luke, a fraternal and mutual aid society providing sick benefits, burial insurance, and uplift to Black families navigating the racism and economic pitfalls of postwar Virginia. Within this organization, Maggie discovered her life’s calling: building real financial power for Black communities long excluded from mainstream institutions.

Under her leadership, the once-struggling St. Luke Order flourished. In 1903, she founded the St. Luke Penny Savings Bank, an institution that offered savings accounts, mortgages, and business loans to the underserved. It even distributed small “penny banks” to children to teach them about thrift and building community wealth. The bank’s success helped turn Richmond’s Jackson Ward district into a thriving center for Black enterprise and home ownership.

Maggie was the first Black woman—and the first woman of any race in the United States—to charter and serve as a bank president, harnessing the collective power of mutual aid to organize Black families to save, build, and invest in themselves in the face of discrimination and economic exclusion in Jim Crow Virginia. Her institution encouraged both adults and children to save, invest, and reinvest within their own neighborhoods—“turning nickels into dollars,” as she famously said.

Beyond banking, she launched the St. Luke Herald newspaper and opened a department store staffed by and for Black workers, creating a model of cooperative economics that defied the injustices of Jim Crow.

Maggie was the first Black woman—and the first woman of any race in the United States—to charter and serve as a bank president, harnessing the collective power of mutual aid to organize Black families to save, build, and invest in themselves in the face of discrimination and economic exclusion in Jim Crow Virginia. Her institution encouraged both adults and children to save, invest, and reinvest within their own neighborhoods—“turning nickels into dollars,” as she famously said.

Beyond banking, she launched the St. Luke Herald newspaper and opened a department store staffed by and for Black workers, creating a model of cooperative economics that defied the injustices of Jim Crow.

Reflection: What drives you forward when faced with personal challenge?

Reflection and Action: Journal Prompts for Everyone

Uplifted by Madam C.J. Walker? What wild invention would you like to create to bring joy and fulfillment to other women?

Moved by Mary Ellen Pleasant? How can or do you use your success to create change?

In awe of Biddy Mason? How do you turn adversity into opportunity for others? Write about a time you helped someone despite your own struggles.

Inspired by Maggie Lena Walker?If you could establish a new financial vehicle, who would it serve and what would it do?

HerStory / OurStory: Journal Prompts for Women of Color

Thinking about Madam C.J. Walker - Why was the haircare product line she founded so important to Black women at the turn of the 20th century?

About Mary Ellen Pleasant - When has silence been a strategy—not a weakness?

Reflecting on the heroism of Biddy Mason - How has financial knowledge in your family been passed on—or withheld?

Considering the legacy of Maggie Lena Walker - Name some other inspiring people who have turned their financial gain into community value.

Activated Allies: Prompts and Actions for White Friends

For Madam C.J. Walker - Patronize a BIPOC-owned business. Invest in or promote BIPOC entrepreneurs. (I’m one, by the way!)

In honor of Mary Ellen Pleasant - Learn about economic resistance in Black history.

Moved by Biddy Mason - Support organizations that provide direct aid to BIPOC communities.

Celebrating Maggie Lena Walker - Learn about Black-or BIPOC-owned community finance initiatives.

What These Women Knew, and What We Must Remember

In America today, under the shadow of authoritarianism and ruthless political rollback, it’s clearer than ever that capitalism is hardly a vehicle for justice—it’s a machine built for profit and exploitation.

But if there’s a lever that regular people still control, it is the power of the almighty consumer dollar. For those who have the option, every thoughtful purchase, boycott, or collective action stands as a small act of resistance.

Madam C.J. Walker, Mary Ellen Pleasant, Biddy Mason, and Maggie Lena Walker made money moves, using the dollar to invest in themselves, their communities, and building their legacies. We can be inspired by them and uplift others by investing what we can in our collective wellbeing. Let's build power, not just profit.

Thanks for reading this edition of #SistoryLessons, a biweekly newsletter that uses the lessons from Foremothers who led the way as encouragement and guide for these times of resilience. The series is based on stories from my award-winning book, Our Brave Foremothers: Celebrating 100 Black, Brown, Asian, and Indigenous Women Who Changed the Course of History, and other, ongoing research.

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