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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

You may not know her by Elisabeth Ovesen – writer and host of the love, sex and relationships advice podcast Asking for a Friend. But you definitely know her other alter ego, Karrine Steffans, the New York Times best-selling author who lit up the literary and entertainment world when she released what she called a “tell some” memoir, Confessions of a Video Vixen.

Her 2005 barn-burning book gave an inside look at the seemingly glamorous world of being a video vixen in the ‘90s and early 2000s, and exposed the industry’s culture of abuse, intimidation, and misogyny years before the Me Too Movement hit the mainstream. Her follow-up books, The Vixen Diaries (2007) and The Vixen Manual: How To Find, Seduce And Keep The Man You Want (2009) all topped the New York Times best-seller list. After a long social media break, she's back. xoNecole caught up with Ovesen about the impact of her groundbreaking book, what life is like for her now, and why she was never “before her time”– everyone else was just late to the revolution.

xoNecole: Tell me about your new podcast Asking for a Friend with Elisabeth Ovesen and how that came about.

Elisabeth Ovesen: I have a friend who is over [at Blavity] and he just asked me if I wanted to do something with him. And that's just kinda how it happened. It wasn't like some big master plan. Somebody over there was like, “Hey, we need content. We want to do this podcast. Can you do it?” And I was like, “Sure.” And that's that. That was around the holidays and so we started working on it.

xoNecole: Your life and work seem incredibly different from when you first broke out on the scene. Can you talk a bit about the change in your career and how your life is now?

EO: Not that different. I mean my life is very different, of course, but my work isn't really that different. My life is different, of course, because I'm 43. My career started when I was in my 20s, so we're looking at almost 20 years since the beginning of my career. So, naturally life has changed a lot since then.

I don’t think my career has changed a whole lot – not as far as my writing is concerned, and my stream of consciousness with my writing, and my concerns and the subject matter hasn’t changed much. I've always written about interpersonal relationships, sexual shame, male ego fragility, respectability politics – things like that. I always put myself in the center of that to make those points, which I think were greatly missed when I first started writing. I think that society has changed quite a bit. People are more aware. People tell me a lot that I have always been “before my time.” I was writing about things before other people were talking about that; I was concerned about things before my generation seemed to be concerned about things. I wasn't “before my time.” I think it just seems that way to people who are late to the revolution, you know what I mean?

I retired from publishing in 2015, which was always the plan to do 10 years and retire. I was retired from my pen name and just from the business in general in 2015, I could focus on my business, my education and other things, my family. I came back to writing in 2020 over at Medium. The same friend that got me into the podcast, actually as the vice president of content over at Medium and was like, “Hey, we need some content.” I guess I’m his go-to content creator.

xoNecole: Can you expound on why you went back to your birth name versus your stage name?

EO: No, it was nothing to expound upon. I mean, writers have pen names. That’s like asking Diddy, why did he go by Sean? I didn't go back. I've always used that. Nobody was paying attention. I've never not been myself. Karrine Steffans wrote a certain kind of book for a certain kind of audience. She was invented for the urban audience, particularly. She was never meant to live more than 10 years. I have other pen names as well. I write under several names. So, the other ones are just nobody's business right now. Different pen names write different things. And Elisabeth isn’t my real name either. So you'll never know who I really am and you’ll never know what my real name is, because part of being a writer is, for me at least, keeping some sort of anonymity. Anything I do in entertainment is going to amass quite a bit because who I am as a person in my private life isn't the same a lot of times as who I am publicly.

xoNecole: I want to go back to when you published Confessions of a Video Vixen. We are now in this time where people are reevaluating how the media mistreated women in the spotlight in the 2000s, namely women like Britney Spears. So I’d be interested to hear how you feel about that period of your life and how you were treated by the media?

EO: What I said earlier. I think that much of society has evolved quite a bit. When you look back at that time, it was actually shocking how old-fashioned the thinking still was. How women were still treated and how they're still treated now. I mean, it hasn't changed completely. I think that especially for the audience, I think it was shocking for them to see a woman – a woman of color – not be sexually ashamed.

I hate being like other people. I don't want to do what anyone else is doing. I can't conform. I will not conform. I think in 2005 when Confessions was published, that attitude, especially about sex, was very upsetting. Number one, it was upsetting to the men, especially within urban and hip-hop culture, which is built on misogyny and thrives off of it to this day. And the women who protect these men, I think, you know, addressing a demographic that is rooted in trauma that is rooted in sexual shame, trauma, slavery of all kinds, including slavery of the mind – I think it triggered a lot of people to see a Black woman be free in this way.

I think it said a lot about the people who were upset by it. And then there were some in “crossover media,” a lot of white folks were upset too, not gonna lie. But to see it from Black women – Tyra Banks was really upset [when she interviewed me about Confessions in 2005]. Oprah wasn't mad [when she interviewed me]. As long as Oprah wasn’t mad, I was good. I didn't care what anybody else had to say. Oprah was amazing. So, watching Black women defend men, and Black women who had a platform, defend the sexual blackmailing of men: “If you don't do this with me, you won't get this job”; “If you don't do this in my trailer, you're going to have to leave the set”– these are things that I dealt with.

I just happened to be the kind of woman who, because I was a single mother raising my child all by myself and never got any help at all – which I still don't. Like, I'm 24 in college – not a cheap college either – one of the best colleges in the country, and I'm still taking care of him all by myself as a 21-year-old, 20-year-old, young, single mother with no family and no support – I wasn’t about to say no to something that could help me feed my son for a month or two or three.

xoNecole: We are in this post-Me Too climate where women in Hollywood have come forward to talk about the powerful men who have abused them. In the music industry in particular, it seems nearly impossible for any substantive change or movement to take place within music. It's only now after three decades of allegations that R. Kelly has finally been convicted and other men like Russell Simmons continue to roam free despite the multiple allegations against him. Why do you think it's hard for the music industry to face its reckoning?

EO: That's not the music industry, that's urban music. That’s just Black folks who make music and nobody cares about that. That's the thing; nobody cares...Nobody cares. It's not the music industry. It's just an "urban" thing. And when I say "urban," I say that in quotations. Literally, it’s a Black thing, where nobody gives a shit what Black people do to Black people. And Russell didn't go on unchecked, he just had enough money to keep it quiet. But you know, anytime you're dealing with Black women being disrespected, especially by Black men, nobody gives a shit.

And Black people don't police themselves so it doesn't matter. Why should anybody care? And Black women don't care. They'll buy an R. Kelly album right now. They’ll stream that shit right now. They don’t care. So, nobody cares. Nobody cares. And if you're not going to police yourself, then nobody's ever going to care.

xoNecole: Do you have any regrets about anything you wrote or perhaps something you may have omitted?

EO: Absolutely not. No. There's nothing that I wish I would've gone back and said to myself, no. I don’t think at 20-something years old, I'm supposed to understand every little thing. I don't think the 20-something-year-old woman is supposed to understand the world and know exactly what she's doing. I think that one of my biggest regrets, which isn't my regret, but a regret, is that I didn't have better parents. Because a 20-something only knows what she knows based on what she’s seen and what she’s been taught and what she’s told. I had shitty parents and a horrible family. Just terrible. These people had no business having children. None of them. And a lot of our families are like that. And we may pass down those familial curses.

*This interview has been edited and condensed

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Feature image courtesy of Elisabeth Ovesen

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