Aiesha Letman Turned Her Twitter Wit Into Jobs Running Bossip & The Shade Room—Now She's Sharing Her Story

It all started with Twitter.

Like most of us, Aiesha Letman often found herself scrolling her timeline to catch up on the latest in pop culture. The difference between her and many other users though was her witty tweet responses got noticed by the head of a major media company, which then led to a life-changing offer.

“In 2014, Twitter particularly Black Twitter was just fun,” Letman said. “People were just talking—using it as a dumping ground—speaking your mind without much consequence. But for reason, my tweets would far because of how I expressed my opinions. One day, the managing editor at Bossip at the time DM’ed me and said I had a really unique voice about the happenings in Black culture at the time, and she wanted to hire me as a freelance writer.”

That opportunity to work for the wildly popular blog was the launchpad for Letman’s career in media, but her storytelling skills were honed long before then.

Growing up, the Jamaica Queens, New York native learned early on that the power of quick wit and crafty word play was tantamount to survival in her neighborhood. “We were always talking mess to each other, sharing stories about what happened around the way which could easily turn into a roasting session, and you needed to know how to handle yourself,” she said. “It was always a battle of the wills and I shaped my ability to think on my toes that way.”

That natural wittiness was coupled with her love of writing, a hobby Letman said she picked up to help escape some of the tough realities of her childhood. “Queens is such a big and busy place to grow up in,” she explained. “So, I knew early on I had to find a thing to concentrate on and funnel my energy into.”

Letman shared that her mother faced substance abuse while pregnant with her, which led to them being separated. “I was told that as an infant, I would violently shake from the drug withdrawals–that’s how intense my mother’s addiction was,” she shared with Essence.

Before she was adopted in her later adolescent years, Letman spent time as a ward of the state–something she says changed the trajectory of her life forever.

“Growing up in foster care, I had lots of hobbies to kind of distract me from real life,” Letman said. “That’s where my interest in writing started. I would journal and write about my feelings, and then that turned into creating fictional stories…just making things up.”

This early interest led to her working on her high school’s newspaper crew and penning short stories. But instead of exploring her talent after graduating, Letman dove into the job market. Admittedly, that was a move she couldn’t have predicted would inadvertently lead to the career she has today.

“I went straight from high school to bartending, then jumping on the internet, and then getting into this,” she said, explaining that after a short time freelancing with Bossip she was named as a lead editor. But it isn’t lost on her that the path she took was untraditional.

She continues, “I have a team of writers who have Masters’ in Fine Arts and Bachelor’s degrees in journalism, and I didn’t formally study this at all,” she shared. “But I’m leading them because what we really care about is reaching our audiences in impactful ways and hitting our goals no matter what.”

After working with the outlet for nearly a decade, Letman said she helped build the platform into what it is today. “I led editorial at Bossip for eight years, and also spent time at the blog OnSite! for two years in a leadership role where I was running the page, very quietly, and attracted tens of thousands of dollars a month in ad sales,” Letman shared.

After educating herself on digital advertising and growth strategies, she realized she was selling herself a bit short in terms of pay equity.

“A goal I set for myself was focusing on being comparably compensated for my impact, because at the time, I’d grown online followings from 70,000 to 700,000 in a year. I wanted more for myself.”

In early 2022, she was offered a role with social media behemoth, The Shade Room. Starting as a wildly popular Instagram account that reported on Black celebrity news, it quickly turned into a cultural staple and needed support with running and monetizing their website. The Shade Room’s CEO and founder, Angelica Nwandu knew Letman was just the woman for the job. It took Letman some self-convincing though. “When I was first approached by Angelica, I was hesitant to accept the role because I was so used to being behind the scenes, ideating and quietly making things happen for these huge media companies but never allowing myself to fully receive the credit I deserved,” Letman said, sharing that she was largely responsible for steering Bossip’s brand strategy toward creating punchy and often alliterative story headlines to stand out from their competitors. She also mentioned that the stories she’d written were often uncredited, so she began to share them on social media and attribute herself. This tactic clearly worked.

Letman eventually accepted the role as managing editor for The Shade Room in April 2022, and has already made an incredible impact.

She says she’s helped drive more site traffic by ensuring readers’ interests are prioritized above all else. “Right now, video is king in media,” she pointed out. “The message will get lost if we don’t add a strong visual element to the story and that’s what we’re focusing on right now.”

This strategic insight is something that’s second nature to her through years of observation and hard work. For Letman, that’s just the beginning. “I want those who read the stories I quietly wrote for years or decided to follow the account of the blogs I ran to finally see the person behind the content, and beyond that, hear my story,” she said. “I had to realize that my journey can inspire others to champion themselves. That’s what this has always been about.”

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