Struggle is often one of the major themes when popular culture covers Black History Month. This month, we’re looking not just at struggles, but at successes. Throughout American history, the contributions of Black entrepreneurs have often been overlooked or relegated to the footnotes of history. Get inspired by these three amazing entrepreneurs, through history until today.
1800s: Josephine N. Leary
If you’ve been watching the successful Black women in real estate on the reality series Ladies Who List: Atlanta, you’re seeing a bit of the legacy of Josephine N. Leary. Born into slavery, Leary became a trailblazing real estate maven in North Caroline during the post-Civil War era.
Leary was born into slavery around 1856, and she was freed at around nine years old. Following the war, she married Archer “Sweetie” Leary, and the couple settled in Edenton, North Carolina. Both Learys were barbers by trade and ran a barbershop in Edenton, but the idea of expanding further appealed to them, especially to Josephine.
Over the next several years, Josephine Leary broke barriers of both race and gender, as a Black woman who owned and developed property in her own right. By 1881, after navigating a challenging real estate market that, like many others aspects of life, saw her at a disadvantage due to both race and gender, Leary owned six properties. One such set of buildings, on Broad Street in Edenton, was part of a historic business district called Cheapside.
Leary’s real estate business hit a major bump in the road in 1893, when a fire tore through the Broad Street area of downtown Edenton, including Cheapside and Leary’s buildings. Instead of giving up on the properties, Leary redeveloped and rebuilt. The rebuilt 421-423-425 South Broad Street, the old Cheapside property, still stands in downtown Edenton today, with “J.N. Leary – 1894” proudly displayed on its façade. Leary would be proud to see her legacy continued by leagues of successful Black women working in real estate sales and development across the country.
1900s: Madam CJ Walker
You’ve almost certainly heard of Madam C.J. Walker, whose revolutionary beauty business led her to become the first American woman confirmed to be a self-made millionaire. Born Sarah Breedlove, Walker lived through a tragic childhood (both her parents died by the time she was seven) and a difficult start to her adult life.
In 1888, after the death of her first husband, Walker and her daughter moved to St. Louis, where she worked as a laundress. Her brothers worked as barbers in the city, and it was during this time that she began developing scalp, hair, and skin problems. Around 1904, Walker began working as a sales agent for Annie Malone, a Black woman who had made haircare into a million-dollar enterprise.
Over the next few years, Walker made major changes in her life. At the age of 37, she moved to Colorado with her daughter. She married Charles Joseph Walker and took on the moniker of “Madam C.J. Walker,” and she developed her own line of products for skin and hair care. With her husband as a business partner, Walker sold cosmetics door-to-door and taught other Black women how to best care for their hair and skin – an early focus on “customer experience,” one might say!
Eventually, Walker’s business grew to the point that she launched a mail-order branch. Over the next several years, she moved to different cities, established salons and training facilities, offered advice and training to other women looking to become entrepreneurs, and built a bona fide beauty empire – all while promoting women to positions of influence, management, and power.
Today, Black-owned beauty brands are bigger than ever. One survey from 2020 revealed that, while Black-owned brands represented just 4% of “prestige” makeup, they performed 1.5 to 4 times better in May, June and July 2020. Major retailers have signed on to the “Fifteen Percent Pledge,” committing at least fifteen percent of their shelves to products from Black-owned beauty brands.
2000s: Robert Reffkin
Founder & CEO of real estate company Compass, Robert Reffkin was inspired by his mother’s challenges working as a real estate agent. Reffkin grew up with a single mother – an Israeli immigrant — and often cites her as the inspiration for his resilience and entrepreneurial spirit. After graduating from Columbia, his early career was filled with impressive achievements, including being named a White House Fellow and working for major companies like McKinsey and Goldman Sachs.
During this time, he also spent significant time on philanthropic efforts, including career development and mentorship for low-income students. His signature effort is the nonprofit America Needs You, which has grown from a New York-based program to a national organization supporting first-generation, underrepresented, and low-income students as they pursue their dreams.
In 2012, Reffkin co-founded Compass, an online real estate technology company founded on the idea of using advancing technology to give real estate agents the ability to analyze data, research the market, and even develop their personal business brands. When Compass went public in 2021, market experts projected that Reffkin was now on the path to becoming the youngest Black billionaire in America.
Today, Reffkin is one figure among a growing wave of Black entrepreneurs making their mark across a variety of sectors. In September 2021, Bloomberg reported that Black-owned business owners hit a high of 1.5 million, up 38% from February 2020. Although Black entrepreneurs were hit particularly hard by the COVID-19 pandemic, they’re on the rebound and still growing.
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