Daniel Frank Grimsley is a 33-year-old licensed therapist, school social worker, content creator, and motivational personality from Shorterville, Alabama, who has lived in the Washington DC-Baltimore area for most of his adult life. He is an Aries. He describes himself as the “big boy with big personality” — a phrase that became his Season 4 calling card — and has spent years building a brand called Frank N The City around body positivity, self-confidence, and the radical idea that you belong in every room you walk into, regardless of size.
His academic credentials are staggering for a reality TV contestant: he earned his Bachelor’s degree from the University of Alabama, his Master’s in Social Work from Howard University, and a PhD in Organizational Leadership from The Chicago School of Professional Psychology. He is not a person who stumbled into therapy work. He built toward it deliberately, for years, before Netflix called.
‘The Circle’ Season 3 — The $150,000 Win
“The Circle” Season 4 premiered May 4, 2022, with the prize money increased to $150,000 — the highest in the show’s history at the time — after Spice Girls members Emma Bunton and Mel B joined as celebrity contestants and completed a mission to boost the fund.
Frank entered as himself, which by Season 4 was still the exception rather than the rule in a cast that included multiple catfishes. His strategy was the same one he had been deploying his entire life: genuine warmth, radical openness, and the confidence of someone who has decided the room belongs to him before he walks in.
He built alliances with Yu-Ling, Alyssa, Bru, and Rachel and never went out of his way to start a fight or belittle anyone behind their backs — a discipline that made him one of the most trusted players in the building. He was an influencer three times during the season and was never once targeted — a run so statistically improbable that producers reportedly started getting invested because they kept expecting him to fall and he never did.
In the penultimate episode, he became the Superinfluencer, earning an automatic finale spot. In the finale, the five remaining players ranked each other face-to-face for the last time. Frank won.
His win made him the first LGBTQ+ winner in The Circle’s history. Trevor St. Agathe — who had entered as “Imani,” his wife DeLeesa‘s friend — finished as runner-up. Josh “Bru” Brubaker won Fan Favorite.
After the win, Frank told Tudum: “I’m not overwhelmed with so many emotions because it kind of feels normal to me. I knew I would get to this place one day, so that feels great. But it’s almost like all this stuff belongs to me. I deserve all these things.”
Why He Played as Himself
Frank’s decision to compete as himself was not just strategic — it was a statement. “I really wanted to show little fat boys, little fat girls, and other men and women of big size that we could get into these spaces and be just as popular. I think, growing up, I had this idea that you’ve got to have washboard abs to be popular. You never really see somebody my size being in a space and not only occupying it but owning it. Because I believe every space I walk into, I own it.”
He had also spent years as a therapist helping other people find that belief in themselves. Winning $150,000 on national television by doing exactly that was, in his words, proof of concept.
What He Did With the Money
Frank was refreshingly direct about the finances. “I owe a lot of people money, so I will be definitely paying some people back. I might do a little splurge here and there. I might get me a little vacation, a little bag, but really just trying to save and invest. I want to make this money work for me for the rest of my life.”
He cleared his debt. He took a vacation. He invested the rest.
What He Has Been Up To Since
After filming wrapped, Frank returned to work as a school social worker in the Washington DC-Baltimore area. “The Circle” fame made things interesting at work. One of his students eventually recognized him from Netflix, came back the next day, and confirmed: “Mr. G, are you sure you don’t know a show called ‘The Circle’?” Frank played dumb. He wanted to show them the winning moment eventually — just not the whole season, because he curses a lot.
Beyond the day job, Frank has continued building his Frank N The City brand — event hosting, licensed therapy work, business strategy consulting, and his role as Committee Chair of the Joshua K. Spann Scholarship Foundation.
He also became a content creator for the New York City DMV, which is either the most unexpected post-Circle career pivot or the most Frank Grimsley thing imaginable, depending on how well you know him.
He has 148,000 Instagram followers and posts with the same motivational energy that made him compelling on screen — gratitude posts, body positivity content, and the occasional reminder that some days it is okay to just be.
The Legacy
Frank Grimsley won The Circle by being exactly who he said he was from the first episode to the last. He did not strategize his way to the top so much as he was so genuinely and sustainably himself that the cast ranked him there every time they had the chance. The $150,000 was the largest prize in the show’s history. The first LGBTQ+ winner in the franchise’s history. The PhD therapist who went back to being a school social worker the week after the finale aired.
When one of his students asked if he was sure he wasn’t on Netflix, he said no. He must have a twin. Couldn’t be him.
“The Circle” Seasons 1 through 7 are streaming now on Netflix.
Read next:
- Who Is Nick Uhlenhuth? ‘The Circle’ Star’s Netflix Journey & What’s Next
- Where Is Kai Ghost From ‘The Circle’ Season 3 Now?
- Who Is Chloe Veitch? Her Netflix Career & Where She Is Now
- Where Is Lee Swift (River) From ‘The Circle’ Season 2 Now?
- Where Is Joey Sasso From ‘The Circle’ Now?
- Who Is Shubham “Shooby” Goel? ‘The Circle’ Star’s Career & Netflix Shows — Where He Is Now
For more “The Circle,” click here.
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