In the summer of 2020, Sully Finlay walked into an improv class alone. A friend who was supposed to sign up alongside him had backed out. Sully, an accountant from the Midwest, spent three years climbing the corporate ladder. “I walked into that class, and I was like, ‘Oh, this is where I was supposed to be, like, my entire life,’” he says.

That class was the first link in a chain of events that led to graduating from the Second City Conservatory, building a following of more than 325,000 across TikTok and Instagram, and landing brand partnerships with Delta Air Lines, Salesforce, and Gillette. After seven years as a CPA, Sully is now pursuing comedy full-time.

The Chicago-based comedian, writer, and content creator refers to himself as a “recovering CPA.” “The dirty little secret I tell people is like, I liked accounting,” he says. The comedy career he built online is just the beginning. Today, he is acting in web series, upgrading his camera equipment, and building toward a long-term goal that has nothing to do with follower counts: a recurring role in a sitcom.

Introverted, Anxious, and Playing Trombone

The pull toward performing showed up early. Sully played trombone and baritone in high school.  

In high school, he watched friends in theater. “I think that’s the thing. I think that’s what I want to do,” he remembers thinking. “I was just too introverted and socially anxious to go audition for things like that,” he says. He graduated from Taylor University with an accounting degree in 2017 and went to work.

Improv didn’t happen until just before everything shut down in the pandemic. Sully and his friend had first heard about improv on a podcast and suggested they sign up for a class together. Sully arrived, as he describes it, as “just a Midwestern accountant in an improv class.” The environment was unlike anything he had encountered professionally. “In a lot of school or work contexts, it’s like you’re kind of punished for being silly,” he says. “In improv, it’s not only accepted, it’s rewarded.”

In the pandemic, classes eventually went online. Sully began studying at ComedySportz, the  Second City, and Upright Citizens Brigade, eventually graduating from the Second City Conservatory in 2022. He started posting content in the fall of 2021, not to build a following but to give the characters he was developing on stage another outlet.

Seven Months of Silence, Then a Checklist About Chicago Neighborhoods

For seven months after Sully started posting, nothing went meaningfully viral. He posted every day. Growing up playing sports, his parents had enforced a rule that stayed with him: you do not quit before the season ends. “If I was playing soccer and a season wasn’t going well, I couldn’t just quit in the middle of the season,” he says. So, he kept posting.

The first traction came from an observation about something he had experienced repeatedly after relocating to Chicago: the predictable sequence of questions whenever someone new met him. Where do you live? What neighborhood? How far from the lake? He structured the exchange as a numbered progression, a format that later evolved into the checklist videos he continues to make today. “I think it was just hyper relatable,” he says. 

By late 2023, he had signed with his management company, Odyssey Entertainment Group, and was approaching the income threshold he had set as the condition for going full-time. “I wanted to get to a point where I’d fully replace my income as an accountant,” he says. “That was my trigger.”

Pillar Content, Monthly Big Swings, and the AI Coworker Nobody Remembered

Sully structures his content with a scheduled approach, setting aside dedicated time weekly for strategy. He divides what he posts into two categories: pillar content that reliably connects with his audience, and what he calls “big swings,” one or two a month, with uncertain outcomes.

One of the “big swings” was a series with fellow comedian and creator Jacob Capozzi that compares how movies portray workplace situations with how they actually play out in real life. The format became a recurring feature, with the first installment focused on accounting. An experiment that did not stick. An AI coworker character he posted about a year and a half ago failed to catch on. “Nobody knows what that is. It didn’t work at all,” he says. He’s fine with that.

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Follower counts are not the metric that drives him. “The biggest thing I think of is, ‘Is something funny?’ And if so, I want to make that,” he says. 

The Isolation Nobody Mentioned Before He Signed Up

Going full-time, Sully expected the creative freedom. What he did not expect was the quiet. “The thing that really surprised me was how isolated of a career it is,” he says. “There’s so much of it that’s just you and your phone.”

At Salesforce, even working remotely after COVID, there were colleagues to message and occasional office time to share. “I honestly miss the small talk over a cube wall,” he says. About a year into doing this full-time, he started reaching out to other creators. “Hey dude, we’re both in Chicago, do you want to work on something together?” he says of how the Capozzi collaboration began. He works with Callan Harrington as a writing partner. He uses a co-working space.

The outreach solved the problem it was designed to solve. The people he found through it were funny, and he liked being around them.

What Sully Wants CMOs to Stop Doing

Brand deals account for the majority of Sully’s revenue, by his own estimate, and he is actively working to change that concentration by expanding into acting, starting first with acting in web series. For now, those deals define much of how he thinks about his business.

The problem he identifies is familiar. A creator submits a script. It moves through the creator’s agency, then the brand’s agency, then the brand’s internal team. “The brand is like, ‘Okay, great, let’s mention our name in the first 1.5 seconds and then add a paragraph about our brand in the middle of the script,’” he says. The post goes out, performs below expectations, and both sides lose. He sees multi-video, branded miniseries agreements built around creative quality gaining ground. “I think we’re starting to see that change,” he says, “but still probably a ways to go there.”

What he wants from brands is attitudinal as much as structural. “I would want more trust that the creator is the closest person to their audience and engagement with a video,” he says.

On the Path to Film, TV, and Sitcom

Sully is building toward television with the same incremental method he brought to improv. He is currently acting in web series at the intersection of Hollywood’s growing interest in vertical content and brands’ appetite for higher-production creator work. He recently bought a high-end camera, intending to produce more high-quality content himself.

The longer arc is a sitcom, and he is specific about what draws him to the form. “I would love to work up to being in a sitcom and being a recurring character,” he says, “and just having that environment that you get to work in and just be silly and have fun.”

The path, he suggests, is becoming better worn. “Saturday Night Live” has begun pulling more performers from online platforms, and creators in his orbit are landing recurring roles in series and films. The corporate satire built his platform. It is, by his own account, the starting point. Whatever form the screen work takes, he intends to keep performing live alongside it. “Performing is my favorite thing,” he says. “It’s just so fun to be live with an audience.”

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