While attending the University of California, San Diego, he became a columnist for the humor website Cracked.com, and after graduating from college in 2007, he joined with Abe Epperson to co-found the internet sketch comedy troupe Those Aren't Muskets.

[7] In a 2011 interview with The Huffington Post, Swaim explained his artistic influences saying, "I'm sure The Simpsons is a big part of it, and I'd like to think there's some Vonnegut and even a little Shakespeare in there.

[18][19] Fellow MQ editor Abe Epperson befriended Swaim when they were both UCSD sophomores, and the two have remained frequent collaborators throughout their careers.

[9][20][21] Swaim continued during this time to be involved with UCSD's theatre program, producing his own original comedy play, Olympus Inc,[20][22] from which cast members occasionally crossed over into Those Aren't Muskets videos.

Videos produced by the troupe were posted to websites like YouTube, Revver, Cracked, CollegeHumor, and Funny or Die, in addition to the now-defunct thosearentmuskets.com.

[21][25] Gaining media attention,[26] it was identified by The San Diego Union-Tribune as Swaim and Epperson's "first bona fide hit".

[24] In 2008, Swaim's brother, David, guest-starred in "Chops", a Those Aren't Muskets video which placed fourth - over hundreds of submissions - in YouTube's Sketchies II competition.

[37] Those Aren't Muskets remained active for a few more years, producing the web series 8-Bits for Cracked, and joining in 2009 with several other internet sketch troupes for a two-week collaboration known as Genius Camp.

[2][8][43] He continued starring in original video series produced by the website, among them After Hours,[44] which won Best Writing at the 18th Annual Webby Awards.

[8] As Swaim became more involved with video production for Cracked, he wrote fewer columns for the website but took on supplementary work as a blogger for guyspeak.com.

[49][52] In 2010, Swaim told The Huffington Post that he hoped his tenure at Cracked would be a step towards eventually making feature films.

[8] Later that year, Swaim and Epperson were contacted by filmmaker Travis Long, who expressed interest in working with the duo on a feature.

[9][29][53] Swaim, who had a starring role in the film, wrote the screenplay and received a producer credit, while Long directed, and Epperson performed the cinematography.

It then had a limited theatrical release through Tugg, a service that allows people to bring screenings of films to their local city when enough tickets are pre-ordered.

"[64][65] After the release of Kill Me Now, Swaim hoped to quickly continue on to more feature films and grew dissatisfied with his position at Cracked, once it became apparent to him that the company's corporate owners were unwilling to fund any large-scale projects.

[67] Swaim later recounted that his depression, which he had suffered from since childhood, gradually worsened during this stage of his life, and over time, he continued to reduce his role at Cracked.

[68][69] Speaking to the company's struggles, Swaim expressed his view that Cracked had squandered its "potential to become an SNL or a National Lampoon-type brand with feature films and so forth.

[75] The following day, Swaim posted a video online, explaining his decision to resign from Cracked and offering further details about Small Beans.

Extree!, a news-themed series that provides both Small Beans-related updates and comedic takes on current events;[70][71] and Tales from the Pit, in which Swaim is joined by a guest each episode to discuss experiences with depression and other emotionally challenging issues.

[106][109] The first installment of Bean Town features additional voice acting from Burke, Tyler Brown, Noah Byrne, and Kelsey Hudgins,[106][111] while Bean Town II features additional voice acting from David Christopher Bell, Adam Tod Brown, Adam Ganser, Sarah Griffith, Nick Kocher, Mark Little, Jeff May, Jacquis Neal, Teresa Lee, and Tom Reimann.

[114][115] In February 2018, Small Beans premiered its first video series, LifeHax; each episode is a zero-budget improvised spoof of do-it-yourself YouTube tutorials.

[118][119] Another low-budget series, Family Meeting, followed in August; it stars former-Cracked members Cody Johnston and Katy Stoll, alongside Swaim, as siblings who reconnect over webcam.

Cast members announced for Off Hours were Johnston, Stoll, Greg Burke, Maggie Mae Fish, Daniel Vincent Gordh, Teresa Lee, and Damian Washington.

[134] In 2022, Collider named Small Beans one of the best producers of pop-culture podcasts, praising Swaim's work for blending "silly quips and often childish humor" with "surprisingly profound introspection.

[204][205][206][207][208][209][210] In early 2022, he left his position at IGN for what he described as "a narrative design role" with a video game "dev team that's brand new and has not announced themselves.

[211][212][213][214] In 2023, two short stories by Swaim, "The Chosen One" and "Run || Time", were published in the science fiction and fantasy anthology Impossible Worlds.

"[235] Elaborating on his description of the book, he said, "It talks frankly about my alcoholism, mental health struggles, and time at Cracked, but...there's also magic and robots.

"[236] One Last Job was self-released digitally through the Small Beans Patreon shop on February 16, 2024 and is illustrated by Garth von Ahnen.

[239][240] In 2023, Swaim and Epperson successfully raised money through crowdfunding to begin production on a feature film, Papa Bear.

[241][242][243][244] Swaim came out as queer in 2021, saying, "I'm in a monogamous relationship with a partner the world sees as female, but am sexually attracted to all sorts of folks.