Ready To Be Your Own Boss? These Charlotte Entrepreneurs Share Their Best Tips

How to succeed at doing your own thing.

Workin' Girl

This article is in partnership with Visit Charlotte.

Trading the security—hello, regular paychecks and benefits—that come with a 9-to-5 for the unknowns of entrepreneurship requires a big leap of faith. Yet, for the women who dare to start their own venture, and muscle through challenges (particularly those of the last year), the experience is intensely rewarding—doubly so when your business helps bring vitality to your neighborhood, and is supported by your neighbors. But where to start?

These three women, all of whom left successful careers with big corporations to be their own boss, found the welcoming, mid-sized city of Charlotte to be fertile ground for opening up shop. Spoiler alert: They're happier than ever!

Remi Haygood, Charlotte Yarn

Courtesy of Remi Haygood

Remi Haygood learned to knit to deal with the stress of a corporate banking job. As she knit and purled each new skein of yarn, this calming pastime slowly became her passion.

In 2005, Haywood learned that the owner of Charlotte Yarn was looking to sell the store and she decided it was time to leave the corporate world and embark on a new career.

"Even though I had never worked retail, I have never been shy about trying new things," she says. "I liked knowing that I was in control of whether it failed or succeeded."

Haygood admits the learning curve was steep: She'd never used a cash register or run payroll and had no idea about business essentials like applying for tax identification numbers or paying sales tax, all while researching knitting trends, building a local knitting community, and marketing her store to bring in shoppers.

"I thought, 'I'll order yarn and teach people to knit,' but there was a lot of work on the back end to make the business run," she says.

It didn't take long for Haygood to master the basics; she took to entrepreneurship the same way she took to knitting: quickly and passionately. Charlotte Yarn customers embraced the business—and the change in ownership—and cheered Haygood on as she put her own spin on the shop.

The business skills that Haygood developed running Charlotte Yarn were essential for navigating the pandemic. She changed the store hours, introduced beginner knit kits to help people learn the craft during quarantine, promoted one-on-one (socially distanced) knitting lessons and introduced virtual "sit and knit" gatherings. Haygood's now launching corporate team-building events to help others relieve stress through knitting.

"I don't knit as much as I used to and my hobby is now my work," she says. Yet the locals who've supported her from the start are all the better for it. "I find joy in seeing how much knitting has helped other people."

Lindsey Williams, Davidson Wine Co.

Courtesy of Lindsey Williams

After graduating from law school, Lindsey Williams spent a decade working for a big bank. Williams was successful, climbing the corporate ladder and receiving accolades for her work, but she was burned out and looking for new opportunities.

"I started thinking, 'What if I went out on my own? What is something I would want to do?'" she recalls. "I'd always loved wine…and I fostered that love of wine into my next career."

Williams took winemaking classes and participated in an internship with a winemaker in California before opening Davidson Wine Co. in 2019. "As a lawyer, when you have a difficult case, you do a lot of research," she recalls. "I wasn't going to feel comfortable going into wine without knowing a lot about it."

The "urban winery" in Davidson (about a half hour from Charlotte) produces popular wines like merlot, cabernet and chardonnay as well as unique wines like petit verdos and pinotages. As head winemaker, Williams makes all of the wines and offers tastings, wine sales and a bistro menu from the wine bar in bustling downtown Davidson.

Her legal background proved helpful for navigating the federal and state regulations but, Williams admits, "I had no idea all of the hats I'd be wearing: winemaker, retail, marketing, human resources all fall on me."

Opening a wine bar meant trading a (mostly) 9-to-5 career for one that requires working nights and weekends, and the transition to entrepreneurship required several other adjustments. Williams credits local mentors for helping her navigate the challenges and celebrate the successes of being her own boss.

"It's important for women to find other mentors and support," she says. "Having someone to provide a sounding board when I'm having a challenge and leaning on others to help is one of the things that's been really beneficial to me."

Sherry Waters, The Pauline Tea Bar-Apothecary

Courtesy of Sherry Waters

Although Sherry Waters had a background in marketing and public relations, she credits her work as a hospital chaplain for inspiring her to open an herbal tea lounge. "The idea of having a sacred space for the community was planted in my heart," she recalls.

In 2019, Waters opened The Pauline Tea Bar-Apothecary in Charlotte's Camp Greene historic neighborhood district. Customers order steaming mugs of herbal tea, read, meditate, journal or engage in quiet conversation. A grant from the Center City Small Business Innovation Fund allowed Waters to build a labyrinth behind the building in the Camp Greene neighborhood.

"It's quite different from a normal café," she says. "The intention here is to unplug and find respite and solace in a peaceful environment…it's a sanctuary space."

Creating that kind of environment required a great deal of work. Waters studied herbal teas, tapped into community resources, hired staff and maintained long to-do lists to keep things running. In an attempt to do it all, she realized the need to prioritize self-care.

"I've gotten better about learning to say 'no,'" she says. "There have to be boundaries to protect my time."

It's hard to take time off when the demand is so great. The community has embraced the unique space, dropping in for tea and renting the tea bar for special events. During the pandemic, Waters received invitations to sell loose leaf teas and cold brews at two local farmers markets. It added to her schedule but offset COVID-19-related business losses—and brought Waters even closer to her community.

"I've always found Charlotte to be generous, supportive and innovative," she says. "One of the most important skills you can have as a business owner is being part of your community, aware of their needs and able to respond."

Featured image courtesy of Lindsey Williams

ACLU By ACLUSponsored

Over the past four years, we grew accustomed to a regular barrage of blatant, segregationist-style racism from the White House. Donald Trump tweeted that “the Squad," four Democratic Congresswomen who are Black, Latinx, and South Asian, should “go back" to the “corrupt" countries they came from; that same year, he called Elizabeth Warren “Pocahontas," mocking her belief that she might be descended from Native American ancestors.

But as outrageous as the racist comments Trump regularly spewed were, the racially unjust governmental actions his administration took and, in the case of COVID-19, didn't take, impacted millions more — especially Black and Brown people.

To begin to heal and move toward real racial justice, we must address not only the harms of the past four years, but also the harms tracing back to this country's origins. Racism has played an active role in the creation of our systems of education, health care, ownership, and employment, and virtually every other facet of life since this nation's founding.

Our history has shown us that it's not enough to take racist policies off the books if we are going to achieve true justice. Those past policies have structured our society and created deeply-rooted patterns and practices that can only be disrupted and reformed with new policies of similar strength and efficacy. In short, a systemic problem requires a systemic solution. To combat systemic racism, we must pursue systemic equality.

What is Systemic Racism?

A system is a collection of elements that are organized for a common purpose. Racism in America is a system that combines economic, political, and social components. That system specifically disempowers and disenfranchises Black people, while maintaining and expanding implicit and explicit advantages for white people, leading to better opportunities in jobs, education, and housing, and discrimination in the criminal legal system. For example, the country's voting systems empower white voters at the expense of voters of color, resulting in an unequal system of governance in which those communities have little voice and representation, even in policies that directly impact them.

Systemic Equality is a Systemic Solution

In the years ahead, the ACLU will pursue administrative and legislative campaigns targeting the Biden-Harris administration and Congress. We will leverage legal advocacy to dismantle systemic barriers, and will work with our affiliates to change policies nearer to the communities most harmed by these legacies. The goal is to build a nation where every person can achieve their highest potential, unhampered by structural and institutional racism.

To begin, in 2021, we believe the Biden administration and Congress should take the following crucial steps to advance systemic equality:

Voting Rights

The administration must issue an executive order creating a Justice Department lead staff position on voting rights violations in every U.S. Attorney office. We are seeing a flood of unlawful restrictions on voting across the country, and at every level of state and local government. This nationwide problem requires nationwide investigatory and enforcement resources. Even if it requires new training and approval protocols, a new voting rights enforcement program with the participation of all 93 U.S. Attorney offices is the best way to help ensure nationwide enforcement of voting rights laws.

These assistant U.S. attorneys should begin by ensuring that every American in the custody of the Bureau of Prisons who is eligible to vote can vote, and monitor the Census and redistricting process to fight the dilution of voting power in communities of color.

We are also calling on Congress to pass the John Lewis Voting Rights Advancement Act to finally create a fair and equal national voting system, the cause for which John Lewis devoted his life.

Student Debt

Black borrowers pay more than other students for the same degrees, and graduate with an average of $7,400 more in debt than their white peers. In the years following graduation, the debt gap more than triples. Nearly half of Black borrowers will default within 12 years. In other words, for Black Americans, the American dream costs more. Last week, Majority Leader Chuck Schumer and Sen. Elizabeth Warren, along with House Reps. Ayanna Pressley, Maxine Waters, and others, called on President Biden to cancel up to $50,000 in federal student loan debt per borrower.

We couldn't agree more. By forgiving $50,000 of student debt, President Biden can unleash pent up economic potential in Black communities, while relieving them of a burden that forestalls so many hopes and dreams. Black women in particular will benefit from this executive action, as they are proportionately the most indebted group of all Americans.

Postal Banking

In both low and high income majority-Black communities, traditional bank branches are 50 percent more likely to close than in white communities. The result is that nearly 50 percent of Black Americans are unbanked or underbanked, and many pay more than $2,000 in fees associated with subprime financial institutions. Over their lifetime, those fees can add up to as much as two years of annual income for the average Black family.

The U.S. Postal Service can and should meet this crisis by providing competitive, low-cost financial services to help advance economic equality. We call on President Biden to appoint new members to the Postal Board of Governors so that the Post Office can do the work of providing essential services to every American.

Fair Housing

Across the country, millions of people are living in communities of concentrated poverty, including 26 percent of all Black children. The Biden administration should again implement the 2015 Affirmatively Furthering Fair Housing rule, which required localities that receive federal funds for housing to investigate and address barriers to fair housing and patterns or practices that promote bias. In 1980, the average Black person lived in a neighborhood that was 62 percent Black and 31 percent white. By 2010, the average Black person's neighborhood was 48 percent Black and 34 percent white. Reinstating the Obama-era Fair Housing Rule will combat this ongoing segregation and set us on a path to true integration.

Congress should also pass the American Housing and Economic Mobility Act, or a similar measure, to finally redress the legacy of redlining and break down the walls of segregation once and for all.

Broadband Access

To realize broadband's potential to benefit our democracy and connect us to one another, all people in the United States must have equal access and broadband must be made affordable for the most vulnerable. Yet today, 15 percent of American households with school-age children do not have subscriptions to any form of broadband, including one-quarter of Black households (an additional 23 percent of African Americans are “smartphone-only" internet users, meaning they lack traditional home broadband service but do own a smartphone, which is insufficient to attend class, do homework, or apply for a job). The Biden administration, Federal Communications Commission, and Congress must develop and implement plans to increase funding for broadband to expand universal access.

Enhanced, Refundable Child Tax Credits

The United States faces a crisis of child poverty. Seventeen percent of all American children are impoverished — a rate higher than not just peer nations like Canada and the U.K., but Mexico and Russia as well. Currently, more than 50 percent of Black and Latinx children in the U.S. do not qualify for the full benefit, compared to 23 percent of white children, and nearly one in five Black children do not receive any credit at all.

To combat this crisis, President Biden and Congress should enhance the child tax credit and make it fully refundable. If we enhance the child tax credit, we can cut child poverty by 40 percent and instantly lift over 50 percent of Black children out of poverty.


We cannot repair harms that we have not fully diagnosed. We must commit to a thorough examination of the impact of the legacy of chattel slavery on racial inequality today. In 2021, Congress must pass H.R. 40, which would establish a commission to study reparations and make recommendations for Black Americans.

The Long View

For the past century, the ACLU has fought for racial justice in legislatures and in courts, including through several landmark Supreme Court cases. While the court has not always ruled in favor of racial justice, incremental wins throughout history have helped to chip away at different forms of racism such as school segregation ( Brown v. Board), racial bias in the criminal legal system (Powell v. Alabama, i.e. the Scottsboro Boys), and marriage inequality (Loving v. Virginia). While these landmark victories initiated necessary reforms, they were only a starting point.

Systemic racism continues to pervade the lives of Black people through voter suppression, lack of financial services, housing discrimination, and other areas. More than anything, doing this work has taught the ACLU that we must fight on every front in order to overcome our country's legacies of racism. That is what our Systemic Equality agenda is all about.

In the weeks ahead, we will both expand on our views of why these campaigns are crucial to systemic equality and signal the path this country must take. We will also dive into our work to build organizing, advocacy, and legal power in the South — a region with a unique history of racial oppression and violence alongside a rich history of antiracist organizing and advocacy. We are committed to four principles throughout this campaign: reconciliation, access, prosperity, and empowerment. We hope that our actions can meet our ambition to, as Dr. King said, lead this nation to live out the true meaning of its creed.

What you can do:
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Featured image by Shutterstock

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