Jenell Stewart
Course creator

The natural, inherent value of you

What happens when you ask yourself, “What if?” For creator Jenell Stewart, the answer was the freedom to be herself, understanding her value, and the start of a new business.

It started 10 years ago. Just outside a Manhattan night club.

Jenell and her cousin Nenjae walked in; Nenjae turned to Jenell and said: “I’m thinking about going natural with my hair.”

“What? You want to do what?” Jenell responded. “It was just so foreign to hear that a decade ago,” she remembers.

Jenell had been chemically relaxing and straightening her hair since she was six years old.

Every eight weeks, for her entire life, she went to the salon or enlisted a relative to apply the chemicals to her scalp that would straighten the roots that grew in.


And while the chemicals are harsh, and the process can be, as Jenell shares, “painful,” she never questioned the routine.

It was all she knew.

It was also the only option available – or so she thought – for her to feel beautiful.

At 25 years old, Jenell had no idea what her natural hair looked like.

So when her cousin told her she was thinking about going natural, Jenell’s guttural response was fear.

With the stereotypes that have been ingrained in us for a long, long, long, long time from movies to TV commercials, magazines, books – what we see in the world – it wasn't something that I think a lot of Black women were comfortable doing back then, because we didn't have many examples of what beautiful, natural hair could look like.

Jenell didn’t know what she would look like.

She didn’t know what her natural hair would feel like.

She didn’t know how she would take care of it; at that time it was hard to find products for natural hair.

But Jenell’s cousin told her about this small community she’d found on YouTube – women doing what they called The Big Chop: cutting off all their relaxed hair in one swoop to then grow out their natural hair.

“It also sounded like a kind of freedom.”

These women were recording their experiences in salons and barbershops, and made videos about their growth process and the new ways they were styling their natural hair.

Despite Jenell’s initial fear, she was intrigued.

She’d never even thought she had another choice when it came to her hair. And as scary as it sounded to get to know her natural hair for the first time, it also sounded like a kind of freedom.

She started to research, but had no idea then that such a seemingly small act of curiosity was about to change more than just her hair – it would change her life.

The Big Chop

When Jenell got home that night she binged all the YouTube videos where women were documenting their Big Chop.

She was blown away by what she saw.

I never knew Black hair could look like that. Could that be me?

She called her cousin right away: “Let's do it. Let's do it this weekend. I'm going to come over on Friday. You're going to cut my hair and I'm going to cut yours.”


“What?” her cousin replied. “I was planning on transitioning” (i.e. waiting until her new growth was longer before chopping off the relaxed part, to avoid having super-short hair).

Her cousin wanted more time.

But Jenell’s enthusiasm convinced her: “Let's do this.”

I was ready to commit to anything. I just really wanted to be free.

On March 26, 2010, they got together for their Big Chop. They ordered chinese food and made toasts; it was a celebration. Then Nenjae cut Jenell’s hair, and Jenell cut Nenjae's hair.

It was a great experience. We will never forget our big chop date because it's one of those things that for Black women, that day means so much to you.

For 10 years Jenell and her cousin celebrate March 26 “like a birthday.”

Jenell fell in love with her natural hair and all the possibilities she’d never known before – and she couldn’t keep it to herself.

“I just really wanted to be free.”

“It is so hard for me to know something and not tell people.”

Jenell started a blog about natural hair the day after her Big Chop and called it “Kinky, Curly, Coily Me.”

“It is so hard for me to know something and not tell people,” she explains.


Educating people came naturally (she had a master's degree in education and spent her career thus far as a special education teacher).

People loved Jenell’s blog, but readers kept asking her to make video tutorials too.

But Jenell didn’t know how to make videos back then.

And she had no video equipment.

But that May, two months after The Big Chop, Jenell’s uncle called her.

“Hey, Princess,” he said, calling her by her family nickname, “I have a Mac for you.”

Jenell felt like “the universe was sending me this Mac.” It had iMovie installed.

She started making videos right away.


She laughs as she remembers all the mistakes she made early on, learning how to shoot and edit as she went. But she kept going, studying the videos of those she admired to learn how to get better.

She created nonstop.

And she had no idea who those videos were about to reach.

There were complications.

After almost two years and about 56 videos, the natural hair company SheaMoisture reached out to Jenell. They saw her videos, and loved them.

They were looking for ambassadors, and started sending her products regularly for her to promote on YouTube.

Then, because she did so well, they asked her to attend events as a SheaMoisture ambassador, flying her out to Virginia to speak.

Jenell thought that sounded fun and agreed. What she didn’t expect was how much, while walking around the event, she would hear people shout:

Jenell! I love your channel!iaac-jenell-stewart-youtube-screenshot

Then they’d run up and ask if Jenell would take a picture with them. She was floored.

“Who am I that you want to come and take a picture?” she thought.

It was one thing to see views on YouTube. It was another to see shining eyes and hair and hearts coming right up to you.

It was just so exciting.

SheaMoisture paid Jenell for that event, and the amount she made was 5X more than what she made in 40 hours of work at her current day job in education. “I'm in the wrong industry,” she started to think.

Around that same time, she became pregnant with her first child.

There were complications.

And after one doctor’s appointment, she was put on bedrest.

She wasn’t allowed to commute to work.

But she was able to sit at home and make content.

So she did.


For the first time, she experienced what it felt like to dedicate full days to content creation, and as she continued, she started to get that sparkly feeling creators get when momentum builds: “Okay, maybe this could be a thing.”

Then her son was born – healthy and happy – but once she returned to work after maternity leave, her manager wanted her to take a new job – one with more responsibilities but not more pay.

He was shocked when she turned it down. But the time off had helped her step away from the day job “bubble” and remember who she was and all she had to offer: “In the microbubble of everything, sometimes you feel like it's just you and them, and it's not true.”

Jenell knew she could get another job if she needed to – but she wanted to take this opportunity to see if she could turn her growing business into something more.


At the same time, other organizations were reaching out to ask her to speak, she started holding her own successful natural hair events, and she was getting sponsorships for her videos.

What if?

She left her job.

With some courage, and a lot of faith:

I know that I can make this a legitimate business. I just needed to have the faith to do it. And then, from there, it was just a matter of grinding. Grinding, grinding, grinding, grinding.

“I had a hunger in me to make this work.”

The biggest turning point, Jenell explains, was when she started to take herself seriously.

She wasn’t going to wait for brands or opportunities to find her. Before she even knew the phrase “media kit”, she sent out packages and proposals, showing brands what she could do, who she could reach, and how much it would cost.

I was just doing it and putting myself out there, fearlessly and not questioning myself. And not taking it personal if someone said ‘No.’ Just on to the next one. Because I had a hunger in me to make this work. I have to support my family.

iaac-jenell-stewart-with-her-cameraHer husband’s income wasn’t enough to keep them afloat. They kept their expenses low, but she knew she needed to make money soon or she’d have to find another job right away.

But for every 20 “No’s”, there was a yes.

During the first year working on her business full-time she made about half of what she made at her old job. But because they kept their expenses low, it was just enough for her to keep going.

She loved the work, and she loved being home with her son.

It was just enough for her to keep going.

And she knew that even if she hadn’t met her full-time financial goals yet, the part-time income was proof that there was potential. This was possible.

She just needed to leverage the potential that was already there.

And that’s when she started dedicating herself to learning online marketing.

“Why would we not spend that in any endeavor in life?”

Jenell is her own best example of what it looks like to take online marketing education seriously.

I was always reading blogs about how to blog. I was always watching YouTube videos about how to YouTube. I was always reading books.

iaac-jenell-stewart-typingShe saw too many people confuse the access of the internet with ease of building an audience. She was shocked to learn how some people think you can transition to a career in content creation and make money instantly, without education.

When you think about what we spend in time and money for college, why would we not spend that in any endeavor in life?

Jenell focused on finding people who taught online marketing that she trusted, people who were experts in the field. She listened to their podcasts. Attended their webinars. Joined their email lists.

The podcasters who inspired Jenell.

That’s when she learned about online courses, and how email and webinars could be a great way to sell them.

She loved that YouTube sent an email to everyone subscribed to her channel when a new video came out – but what about all the people watching her videos who weren’t subscribed?

And she didn’t think pitching a $1,000 course made sense via a YouTube video.


YouTube and social media would be perfect for getting people on her email list, and then email is where she would build trust and sell her course.

She used lots of opt-ins to build her email list, and still does: “I have tons of landing pages.”

Jenell dedicated two years to her own kind of self-created online business MBA. But instead of owing tens of thousands of dollars by the end of those two years, Jenell had a business that was now consistently making over six figures.

The last hurdle she would have to face was understanding that she was indeed worth six figures.

“Making a YouTube video is like making a peanut butter and jelly sandwich.”

Once Jenell hit six figures in her business, she was elated, but she was also fearful. She had imposter syndrome, and struggled to believe she was really worth what brands were paying her – “because what I do comes to me so easy, I sometimes feel like I have to overcompensate.”

If a brand asked her to make a video for $1,000, she would offer three videos, because making one video felt too “easy” to her: “To me, making a YouTube video is like making a peanut butter and jelly sandwich.”


She didn’t feel right charging someone so much for something that came so easily.

She feared that if she didn’t include a ton of other services along with the video, then brands wouldn’t take her seriously, even though she knew she had the numbers to validate the reach and value one video could provide; she just struggled to believe she was really worth it.

Like when she got hired by Nissan to do an Instagram story takeover at an event in Manhattan. “I got in my head so much,” she remembers.

She spent hours trying to get the perfect image, terrified every time she sent a new photo or video to the person at Nissan in charge of approving the content, thinking it wouldn’t be good enough.

But every time she sent an image, Nissan replied back, instantly: “Love it, post it.”

Their positive response finally helped her see what was there all along.

They hired me because I'm good at this. Why am I making it seem like I don't deserve to be here?

She started educating herself on her particular brand of imposter syndrome and realized:

I was undermining my gift.

When you first start out doing something, you charge a little bit because you're not that good. But would you charge even less when you got faster or better at doing it? iaac-jenell-stewart-using-ck-app

No, you don't charge less.

You charge more because you're better at it.

You can offer more to them.

I have the audience, I have the engagement, I have the experience, and they're coming to me; I shouldn't feel like I can't ask for what I want.

That has changed my life.

Once she tackled her imposter syndrome and started appreciating what she was worth, her income tripled.


“It's still crazy to me.”

Jenell with her 100K YouTube subscriber plaque from her first YouTube channel.

Jenell, the former teacher, can’t believe her life sometimes.

I'm a very by-the-book kind of person, so being in the field that I'm in, it's still crazy to me.

Since her early natural hair blog days 10 years ago, she’s expanded into all kinds of content topics, still that same enthusiastic woman who always wants to share what she’s learning with others. (She's also created a podcast and many successful online courses.)

When she had a daughter, and her fans – especially those who had done the Big Chop with her and were also having daughters of their own – asked if she would teach them how to do their daughters’ natural hair, she said yes.

Jenell with her kids.

Today, Jenell also has a YouTube channel with her daughter Elle, showing her how to be a creator, and together showing moms and their children that they have choices – that who they are is beautiful, and that the possibilities, for their hair and their futures, are endless.


Podcasts mentioned in this article: MyTaughtYou, Journey To Launch, Side Hustle Pro, Million Dollar Bad Ass, The Mattie James Show.

You can connect with Jenell on Instagram or visit her website at

Want to learn the strategies Jenell used to grow her business? Catch the workshop replay with Jenell and Angel Marie, Creator Educator at ConvertKit! You'll get real, actionable steps on how to leverage social media so you can increase your audience and overall sales.

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Isa Adney

Isa is an author and writer and has profiled incredible creators and artists, including Oscar, Grammy, Emmy, and Tony winners. When she’s not writing or interviewing creators, she’s probably walking her dog Stanley, working on her next book, or listening to the Hamilton soundtrack for the 300th time.

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