Jade Weatherington, 36, had long been teaching English on various websites when she created two classes on Outschool, an online course platform for kids, in 2018. One was in arts and crafts and the other was about mastering the five paragraph essay.

Business took a few months to pick up, but by early 2021, Weatherington had added six other classes and was netting $10,000 per month from the site, working just 10 to 12 hours per week.

Outschool offers teachers the opportunity to turn their individual profiles into organization profiles with multiple educators, and in June 2021, Weatherington decided she would take the plunge. She hired seven teachers through April 2022 and offered up to 60 classes on the site, including essay writing for various ages and creative classes like screenwriting.

In 2021, she also started creating courses teaching people how to build an online course themselves. She posted those on her personal website, Teacherjade.com.

Weatherington, who lives in Atlanta, Georgia, with her 14-year-old daughter, now makes about $15,000 per month and is still working around 10 hours per week. Here's how she built her multiple streams of income and dealt with hiccups along the way.

'I scaled too fast'

For the first six months after Weatherington turned her individual Outschool profile into an organization profile, everything was going fine. But in early 2022, "there was a plummet in enrollment," she says.

She noticed a $5 loss while she did her payroll as well. "I remember panicking," she says, "like, well, if I lost $5, what if it's $500" in the future?

Weatherington reached out to Outschool. It turned out the platform was undergoing some internal algorithm changes. She ended up meeting with representatives from the company in October 2022 to make some suggestions about how they might fix the problem.

In the meantime, in June 2022, she took all but 17 classes off the site and started offering a handful on Teacherjade.com instead. She also added classes to another platform she'd been experimenting with, Allschool, which caters to students worldwide.  

When she let her teachers know of the change, some decided to switch over to teaching on Allschool or through Weatherington's personal site, and some preferred to wait it out and see what would happen with Outschool in the fall.

In January 2023, Weatherington saw enrollment on her Outschool classes was back up. She continues to offer those 17 classes on the site and is still offering writing classes on both her personal site and Allschool. All seven of her teachers ultimately came back, and she just hired another.

In her moment of crisis, Weatherington is glad she was able to pivot. But realizes the problem would've been easier to solve if she'd had less people to manage.

"I scaled too fast," she says.

Without her second business, 'I probably would have lost money'

Luckily, even as she was navigating the mishaps with Outschool, Weatherington was able to bring in some revenue from her courses on how to build an online class yourself.

For years, she'd had people reach out to say they wanted to start teaching people online as well. She realized, "when you have something that you're really good at, you can always say that it's easy," she says. "But for someone who's never done it, every single step seems like a challenge."

In her courses, she breaks down how to start an online course including creating the course content and lessons and doing marketing for it. She offers various packages on the subject ranging from $25 to $600.

"If it wasn't for that, I probably would have lost money" when enrollment on Outschool started dipping, she says.  

'Find someone who's a professional in the area'

Her biggest piece of advice as Weatherington has built her businesses: Get a mentor and heed their advice.

"Find someone who's a professional in the area so that you don't hit those pitfalls and you know what you're up against," she says.

Weatherington got into a program called Our Village United, which helps Black entrepreneurs grow their businesses. As part of the program, she was paired up with a mentor herself, Atlanta-based entrepreneur Cole Jones. After hiring her two initial teachers, she told him she wanted to keep ramping up. "Maybe stick with the two that you have for at least a year," she says he advised.

"And I was like, 'Nope. I'm ready,'" she says. Looking back, she realizes had she listened to his advice, figuring out logistics around the Outschool challenges would've been much easier.

"I feel like it wouldn't have been so stressful," she says.

Check out:

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