Entrepreneur: Stephanie Comfort

Business: Oh! StephCo

Tilt: Honest takes on dating and life in her late 30s

Scene: YouTube (66.6K), Instagram (5K)

Snack Bites: 

  • Former school teacher Stephanie Comfort posted a video on the privilege of pretty, which garnered over 900K views to date. 
  • With her content brand Oh! StephCo, she shares her personal dating experiences, complicated friendships, and life in her late 30s. 
  • Her videos elicit thousands of comments from people motivated to respond.
  • Though some brands prefer to stay away from the topics she covers, Stephanie has found some willing to work with her.

Why We’re a Stan: Dating woes, friendship fumbles, and the complicated parts of everyday life, Stephanie has created a content business revealing her major and minor life events. What makes her stand out are her honest takes and opinions on the implications of topics, such as being pretty. 

#ContentEntrepreneur @OhStephco1 turned her honest takes on dating and life in her late 30s into a full-time #ContentBusiness. #Stan #CreatorEconomy Click To Tweet

The Story of Stephanie Comfort

Before amassing thousands of views online, Stephanie Comfort made a living as a middle school teacher. As she taught media and language arts classes, Stephanie found time to produce educational marketing materials and video content for schools she worked.

In 2021, her content creation skills came in handy when she made the transition to become a full-time YouTuber with the Oh! StephCo channel. Her video about pretty privilege attracted over 900K views and 18K comments.

A video take from @OhStephco1 on the privilege of pretty attracted over 900K views and 18K comments on @YouTube. #Stan Click To Tweet

She shares her experience of being considered average in a competitive dating market. In the video, the former educator touches on colorism, ageism, and other issues she faces when dating. Though Stephanie had been uploading videos to her channel for a few months, this one on desirable politics pushed through the YouTube algorithm. After drumming up attention online, she discussed her dating highs and lows and personal takes on self-esteem, fertility, and relationships. 

Being vulnerable online

In an interview with Forbes, Stephanie shares what it’s like to open up to strangers online, especially since the subject matter doesn’t align with Black women’s respectability politics. “I know there’s just so much history there with how we have to pay a higher tax in society when it comes to how we choose to represent ourselves,” she says in the Q&A. “If I choose to talk about certain things, it’s like, ‘Oh, you’re just adding to reasons why people won’t like us,’ … that’s one criticism that I got when it came to the pretty privilege video.” 

Even so, her comment section is filled with messages from subscribers. Some writing similar supporting takes, as seen in her latest video, Mental Health, Femininity, & Living a ‘Soft’ Life. One user wrote, “I haven’t heard about the ‘soft life,’ but it describes perfectly the life I’ve always wanted to live.” Another chimed in: “Loving the content. Ignore the haters. Some of us are SO happy you’re here and being your authentic, unfiltered self.” 

Similar to pretty privileged videos, other sensitive subjects often receive harsher responses. She does what she needs to do to protect her mental health when this happens. She explains to Forbes: “I will limit how much I let the outside world’s opinion get to me by doing things like that, like taking comments away, unlisting certain things. If I feel like it’s not being received in the way that I wanted, I’ll do those things to balance it out and protect myself.”

When content from @OhStephco1 isn't received the way she intended, eliciting harsh responses, she'll take comments away and unlist things to protect her mental health: via @Forbes. #Stan #ContentEntrepreneur Click To Tweet

Sponsorship deals vs. authentic content

Sometimes, the Texan has difficulty finding sponsorship deals because of her content’s subject matter. In an April Fool’s Day video labeled – My Final YouTube Video – Stephanie explains: “What you say and how you say it can affect your collaborative or sponsorships opportunities. I used to work with this company that said they could get [me] brand deals. They were able to get me a couple, but there were a lot of brands that they pitched me to and brands passed.”

She has overcome this obstacle as Hello Fresh, Care/of, and LoveHoney sponsored recent videos. And outside of sponsorship deals, the millennial brings in revenue from fans on Patreon ($5 monthly subscriptions).

In the April video, she adds an important note all creators should follow: “Make sure your content matches who you want to grow into because people are watching, collaborators are watching, and you can miss out on opportunities.”

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About the author

Shameyka McCalman is a wordsmith whose work often centers around fashion, art, and other creatives of color. She earned her communications degree from the University of Massachusetts Boston and enjoys sifting through clothes in local vintage shops, frequenting nearby plays, and gazing at exhibitions on view in museums.