One Woman's Instagram-Fueled Ascent to ‘Boss Lady Status’

Jesseca Dupart’s patience was pretty much spent. What her manufacturer had termed “growing pains” were wearing her down. There was the shipment of Miracle Drops that never arrived at a beauty supply store in Chicago; the furious shop in Oakland, California, that received two orders of Edge Control instead of one; damaged deliveries of styling gels that were returned to her business, Kaleidoscope Hair Products, at full cost; and boxes of shampoo that were so chemically pungent, the fumes gave her staff headaches.

Courtesy of PublicAffairs

Excerpted from The Soul of an Entrepreneur by David Sax. Buy on Amazon.

Jesseca Dupart started as a simple hair salon in this northeastern section of New Orleans, called Little Woods, back in 2012, when she was 30 years old, and by the time I visited her six years later, Kaleidoscope was a rapidly growing brand in the African American beauty market. Salons and beauty supply stores in every state, as well as Canada, the Caribbean, and the UK, sold its products. All of that was driven by Dupart’s relentless marketing on social media, particularly Instagram, where her handle @DArealBBJUDY was about to gain its millionth follower.

Dupart stands little more than 5 feet tall, with big eyes and a wide smile. “BB” stood for Big Booty, a God-given asset that Dupart wasn’t shy about deploying in the steady stream of photos and videos she cranked out around the clock in the service of her business. “If I knew what I was doing was going to be hair, I probably would have changed it,” Dupart says about the @DArealBBJUDY handle, with a grin. This morning she is wearing a pair of Adidas workout tights, Yeezy sneakers, and a bejeweled T-shirt that says Pray Girl, Pray. Her hair was straight and black (one of many extensions she rotates through each week), and her fingernails on this day are nearly 3-inch-long glittering gold, purple, black, and jeweled talons.

In 2018, Kaleidoscope’s growth exploded, with sales going from $100,000 a month at the start of the year, to $1 million by the end of March. The company in Houston that manufactured and distributed Kaleidoscope’s products simply couldn’t handle the speed and volume of the scale, and these problems were irritating Dupart. “We don’t have room for error,” she tells me, as she sits behind her desk at the company’s office, which occupies a few units of the strip mall where her salon had once been. “A mess-up now costs thousands of dollars, where just a few months ago it was a few hundred. We went from having a two-day turnover to 12 days,” she says, flipping between her two phones and her computer. “That shit won’t work!”

Dupart is conflicted, because the man behind these mess-ups was her mentor in the business. He personally convinced her to start selling products when she was a hairstylist, launching her from one of the many African American women with a salon in New Orleans, into a nationally recognized figure in the black hair community, with a rapidly growing multimillion-dollar business.

Kaleidoscope’s demand was growing faster than the company could manage. People would call daily and even show up at the doors trying to buy products that were sold out. But her distributor was on an extended trip to Africa, and failing to help her sort out the growing logistics mess over the phone.

“If he can’t contain a small order, that’s my concern now. I mean, I’m a loyal person, but if this fucks up, it fucks up for everybody that works here,” she says, shaking her head. Dupart pauses, takes a deep breath, puts her hands together in prayer, and closes her eyes. After a few seconds she opens them. “It’s my company, and I can’t sacrifice my company for someone else. There’s too many people counting on me … too many.”

Those people included her family, friends, colleagues she supports in various ways, and her dozen employees. But the most important is the wider community in New Orleans and beyond, who looks up to Dupart as an example of an entrepreneur to follow.

As we walk out to Dupart’s Escalade, which is wrapped in Kaleidoscope decals with a “BB Judy” license plate, a car pulls into the plaza and begins frantically honking at her. Four young African American women jump out and run up to Dupart, screaming in delight as they embrace her. Pulling out phones for selfies, the women explain in giddy tones how they’d just finished their first year of college in Baton Rouge and drove here directly after packing up their dorm rooms to meet Dupart. To these women, DArealBBJUDY is more than a larger- than-life figure marketing hair products through hilarious social media skits with celebrities. She is a budding celebrity herself, whose influence extends far beyond New Orleans, the beauty industry, and hip hop culture. She is a successful black female entrepreneur, telling other young black women just like her that they too can be entrepreneurs.

Over the past two decades, minority women—including African Americans, Latinos, Asians, and Native Americans—have become the fastest-growing group of entrepreneurs in the US. As of 2018, women of color accounted for nearly half of all female-owned businesses in America, representing nearly 6 million entrepreneurs, and a third of a trillion dollars in annual revenue. African American women represented 20 percent of these entrepreneurs, making up the largest segment of female entrepreneurs after white women. Black women are also the only cohort of female entrepreneurs in America whose rates of business ownership exceed those of their male counterparts. If there is a boom in one cohort of American entrepreneurs that matches the mythology of rising interest in starting a business, then that group looks a lot like Jesseca Dupart.

Part of the growth in minority entrepreneurship is due to the demographic shift around America, as immigration changes the face of the workforce and nation. However, African Americans don’t drive that demographic shift in the same way Asian Americans or Latinos do through immigration; their numbers as a percentage of the US population are relatively steady. These women stand out as a group whose entrepreneurial ambitions are backed up by their willingness to put those ideas into action and actually go into business for themselves.

That’s the good news. The more complicated news is that black women and other minorities, like women overall, face greater hurdles to becoming entrepreneurs and succeeding at entrepreneurship over the long term. A 2016 Kauffman Foundation report on gender and entrepreneurship found that women are half as likely as their male counterparts to start a new business. Those businesses tend to be smaller on average than male businesses, financed at a lower rate, less profitable, slower to grow, and more likely to be based at home and in female-centric industries, such as beauty (all hands-on, in-person businesses that are particularly hard hit by the economic fallout of Covid-19). For minorities, the disparity is even deeper. African American female-owned firms generate an average of just $24,700 in revenues annually, compared with $212,300 for white-female-owned firms, presenting a drastic disparity in wealth and opportunity that cuts to the heart of systemic inequality in America.

This, of course, is not merely an economic story but also a cultural one. With a smattering of exceptions, minority entrepreneurs and female entrepreneurs have been left out of the heroic story of modern American entrepreneurship.

“When I’m speaking I ask everyone in the room to close their eyes and picture a successful entrepreneur,” says Julianne Zimmerman, the managing director of Reinventure Capital, an impact investment firm that targets companies run by minorities. “Then I say ‘Who thought of Tristan Walker, Sarah Blakely, Richelieu Dennis, or Robin Chase?’ The room is very quiet. Because everyone was thinking of the same icons: Steve Jobs, Elon Musk, Zuckerberg, Gates,” she adds. “The prevailing simple story is one that gets retold again and again. That’s the unconscious bias. None of us is intentionally thinking of excluding those stories. But when we encounter or think of entrepreneurs, we look at what we expect to see. And when we find something that doesn’t fit, we have lots of questions.”

For investors, whether they’re Palo Alto venture capitalists or loan officers at a New Orleans bank, that bias leads them to ask women and minority entrepreneurs seeking financing for more answers, details, and data to overcome those biases—something that white male entrepreneurs are not required to do in the same way. The Silicon Valley startup model of entrepreneurship produces more Silicon Valley–style startups, reinforcing inequality for entrepreneurs.

“We see for certain that women, people of color, and immigrants are far more likely to start businesses and actually stick with them, than in fact the target demographic among VCs,” Zimmerman says.

These entrepreneurs also tend to be more community focused than others. They set up businesses to serve their communities, foster relationships in those communities, and use entrepreneurship to strengthen their communities. For black women in New Orleans’s hair and beauty trade like Dupart, community isn’t just a place where you set up a business. It anchors the very soul of entrepreneurship.

Jesseca Dupart’s rise into the upper echelons of this business is pretty typical of female African American beauty entrepreneurs, especially those I spoke with in New Orleans. She was raised in the city’s Seventh Ward to a middle-class family. Her beloved father, Jesse, who died in 2011, was an accountant that worked for Shell and a local university, as well as an entrepreneur who owned a liquor store and rental properties. Dupart’s mother, Evelyn, worked at the post office and had been helping her daughter with Kaleidoscope’s shipping since her retirement.

Like many other women I spoke with, Dupart’s love of hair was born during weekly visits to the salon. “I just liked doing hair and nails and dressing up,” Dupart recalls, as she drives her Escalade on the highway while simultaneously juggling two phones. “Me and my sister went to the salon every Saturday. It was an all-day thing. We had long full hair that wasn’t manageable. As a kid you hated the dryer, but there’d always be people there. Someone would bring in supper plates … crawfish or gumbo or barbecue. I liked getting my hair done. I liked the look after. But more than anything I liked the atmosphere. When you were young it was positive energy.”

By age 7, Dupart was already cutting and styling the hair on her dolls. By 12, she was braiding her friends’ hair after school. Dupart’s parents initially discouraged this (they had high hopes she would become a lawyer or another professional), but when she got pregnant at 15, they let her start charging for her services and transfer to a trade school to study cosmetology.

Dupart worked out of her family’s home before and after school, styling the hair of fellow students, relatives, friends, and neighbors, until she built up a loyal clientele. “I didn’t just do good hair,” she says, “I had good customer service.” By 18, Dupart had two children (she now has three) and was making good money, far better than she could have made at the minimum-wage jobs available to her. She soon rented a chair at a beauty salon.

After Hurricane Katrina struck New Orleans in 2005, Dupart moved to Houston. She had $20,000 saved from her business but had no access to FEMA funds and quickly spent it covering living expenses for her family. She set up shop in a rented house and began doing hair for other New Orleans exiles, advertising by printing photos at Kinko’s of hairstyles she’d done, then pasting them around Houston.

For half a year, Dupart lived between the two cities, rebuilding her life and business in New Orleans during the week, then driving to Houston Friday night, to see her kids and cut hair for two days straight before driving back. “It was exhausting,” she said. “I love money, opportunity, and growth, but it was exhausting.”

By 2007, Dupart had saved enough to open her own shop and beauty salon with her romantic partner, Ro. This is when she first began to dabble with social media marketing, posting photos and videos on Facebook to draw in business, then hiring local hip hop celebrities, radio DJs, and social media influencers to attend events at the salon. Eventually, as a result of the recession and changing dynamics with Ro, she sought to go solo. She registered the name Kaleidoscope, inspired by her love of colors, at the end of 2012.

“I’ve decided to branch off on my own,” Dupart announced in an Instagram post. “God has placed on my heart a phenomenal plan … and I’m just executing it.” Kaleidoscope salon opened in August 2013, secured with an $1,800 rent deposit (out of her remaining $2,000 savings). Dupart worked tirelessly over the next months to acquire the chairs, sinks, dryers, and other infrastructure she needed and paid for them one cut, style, braid, and weave at a time. There was no investor. No bank. No debt. She didn’t even consider them. Dupart became an entrepreneur by what she calls “grit ’n’ gravel.”

Of the dozen black female entrepreneurs I spoke with in New Orleans, not a single one, regardless of their financial success, went to the bank for a loan or sought venture capital or outside financing of any sort. That idea was so drilled into their head as inaccessible that it seemed ridiculous to even consider. As the dismal diversity of the venture capital industry’s deals and dealmakers shows, even when they get in the door, black entrepreneurs are rarely given access to the contacts, networks, and communities of money that white entrepreneurs often have. Without that capital, many African American entrepreneurs are destined to remain in a state of limbo, unable to fully realize their dreams because they lack the wealth and privilege to take a bigger risk.

Unfortunately, being a black entrepreneur in America has never been as simple as opening a business. Ownership may be the first step to overcoming inequality, but it is insufficient on its own. There have been overt economic and political barriers that restrict black businesses at every turn and subtler racism that undermines their efforts.

Even today barriers continue to grow. Tennessee has fined hair braiders (an exclusively African American group) hundreds of thousands of dollars for braiding hair without a license, hitting young black women right as they are dipping their toes into starting potentially successful businesses of their own.

In December 2013, a stylist left a curling iron on overnight, and Dupart’s entire salon burned down. Kaleidoscope reopened in July 2014, and Dupart soon began selling hair products under its brand name. To market these products, which included Sleek Edges (a styling product) and Miracle Drops (a hair repair formula), Dupart got increasingly creative on social media, teaming up with Raynell Steward, a makeup artist who worked at the salon and went by the social media handle Supa Cent, to create funny skits online.

Most were just short videos of Dupart talking, sometimes in the office, sometimes in a car, or at an event. But increasingly there were well-produced, pop culture parodies, including a takeoff on the NWA rap anthem “Straight Outta Compton” featuring all the Kaleidoscope stylists preaching the strength of their “wig game.” There was a series of videos called Judy Springer (a take on Jerry Springer), parodies of TLC and Atlanta trap rap videos, and even a trippy remix of the Willy Wonka Oompa Loompa song, with Dupart dressed as Wonka in a top hat, while half a dozen little people dance around her, twerking. As Kaleidoscope Hair Products grew, Dupart started posting videos where she would “run up” on African American celebrities and offer them Miracle Drops. These have included big names like Snoop Dogg, Floyd Mayweather, and comedian Michael Blackson, as well as Instagram celebrities like model/rapper Taylor Hing (aka Chinese Kitty). In addition to this there are thousands of photos of Dupart in every conceivable outfit and situation, from lying in bed in the morning to wearing gigantic ball gowns or fuzzy costumes, to her workout videos and weight loss challenges, and of course pictures of babies, dogs, family, and more dogs. Supa Cent remains a constant presence in DArealBBJUDY’s social media feed.

All of this might look like fun, but Dupart’s social media presence forms the core of Kaleidoscope’s financial success and comes at an increasing cost. Dupart spends most of her time marketing herself and her business online. Her phones are rarely away from those glittering nails, and as the production values rise, so do the costs. Celebrities appear in Dupart’s videos because she pays them; a few thousand for a local influencer, but for someone like Snoop Dogg, it’s well into five figures, paid in cash. When Dupart’s accountant inquired about getting 1099 IRS payment forms from one of these recent videos in Atlanta, Dupart laughed so hard she nearly fell off her chair.

“These are hood-assed niggas!” she told the accountant. “Young Jeezy ain’t gonna sign no 1099!”

As I followed the evolution of DArealBBJUDY’s ascent online, what really struck me was how her social media presence quickly evolved from selling Kaleidoscope products to a broader forum for inspiring entrepreneurship in young black women. Dupart regularly posted sales figures and portions of her tax returns, photos of products being shipped and the operation expanding, and stories about paying off her debt or buying a new house or luxury car. In each one of these she thanked God, but explicitly told women to trust in themselves and go out on their own. Dupart was showing other black women that entrepreneurship was aspirational, right down to the outfits, trips, cars, and other trappings of wealth she seemed to flaunt online.

Even now, amid the coronavirus crisis, Dupart has kept up her furious stream of content on Instagram, posing in outfits, announcing contests, and encouraging her followers not to squander this time and do that thing they always wanted to do. She is standing up for her entrepreneurs when they need it most.

“I define success as how many people you touch,” Dupart says, as we drive back to the Kaleidoscope offices after meeting the accountant. “Unfortunately, people equate success with money. I bought a Bentley [a luxury car that costs close to $200,000] not because I like cars … I couldn’t care less about them … but because it got respect and people listened to me. I got it for the purpose it served. I like the fact that the money I’m making is very influential. Me doing a skit with Snoop makes someone who went to school with me say, ‘That bitch did it, so I can too!’ That’s New Orleans for ya,” she says, as she hands a teller at the drive-through window of a bank a fat stack of checks to deposit. “I give ordinary people the game to make money. I’m influential by being inspiring.”

That influence is obvious when you read through the comments of her Instagram posts:

“real life goals!!! I come on your page just for encouragement…your such an inspiration!!” wrote @shebarber89 when Dupart posted about buying her house.

“Yessssss! This is what the hell im talking bout! I’m here for this type of boss lady status!!!” wrote @homes.pho.sale when Dupart posted a photo of her wrapped Escalade.

Even when she shared a $178,182 personal tax bill from the IRS, she got women like @branded_brashay18 saying, “Even though i know my taxes would look sick I’m ready for my business to prosper! This is only motivation”

These women see DArealBBJUDY not as a sex symbol or a style icon, but a brilliant businesswoman who wrestled success from a hard place. For African American women, one of the most economically and socially disadvantaged populations in American society, there is a burning need to see role models present entrepreneurship as something possible, desirable, and within their grasp. That comes from the tremendous economic success of businesswomen from C. J. Walker to Oprah Winfrey, but also from cultural icons like Beyoncé, who told all the honeys makin’ money to throw their hands up and be counted.

“Women are now trying to become a force,” Dupart says. “That sense of independence is more important than before. Women are relying on themselves. Women ain’t waiting for men for nothing!”

From the book The Soul of an Entrepreneur by David Sax. Copyright © 2020 by David Sax. Reprinted by PublicAffairs, an imprint of Perseus Books, LLC, a subsidiary of Hachette Book Group Inc, New York, NY. All rights reserved.

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