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How do you turn a passion for fandom into a professional career with legacy publications like Rolling Stone? In this episode of Portrait of a Fangirl, host Jenna Wrenn sits down with freelance writer Dana Reboe to discuss the freelance hustle, overcoming imposter syndrome, and the power of the perfect pitch.
Dana shares her journey from writing reviews for Temple of Geek to interviewing all eight founders of Critical Role. Whether you’re an aspiring writer or a seasoned fan, this conversation offers a raw and honest look at balancing a 9-to-5 with creative ambitions while navigating the modern media landscape.
Portrait of a Fangirl Podcast
The Portrait of a Fangirl Podcast is a series from the team at Temple of Geek. Portrait of a Fangirl initially began as a web series and has now expanded into a podcast series. You can watch and listen both here and on our YouTube channel. The podcast is also currently in its third season.
Hosted by entertainment journalist and historian Jenna Wrenn, at the core of the project is the importance of telling the stories of women who have found inspiration, growth, and power through fandom.
You can listen to the Portrait of a Fangirl Podcast directly on this page and also stream it on Apple Podcasts / iHeart Radio / Spotify and wherever you stream your podcasts. Also, you can watch it on our YouTube channel. We’re also on social media on our website, Instagram, Bluesky, and TikTok.
A Freelancer’s Guide to the Galaxy
In the landscape of modern media, few stories are as unlikely—or as deeply earned—as a freelance writer parlaying a genuine passion for tabletop roleplaying (TTRPG) into a cover story for the most iconic music and culture magazine in the world.
In the latest episode of Portrait of the Fangirl podcast, the conversation turns to the professional trajectory of freelance writer Dana Reboe. Dana discusses the rare alignment of personal passion and high-stakes journalism, specifically focusing on how she transitioned from a dedicated member of the Dungeons & Dragons community to the author of a landmark Rolling Stone cover story on Critical Role.
Reboe’s journey is a prime example of the power of niche expertise. Rather than viewing her fandom as something to be hidden when searching for professional work, she called upon her deep understanding of TTRPG and the power of the a Nat 20 to craft a story that felt both authentic to insiders and accessible to a global audience.
By embracing her roots in the D&D fandom and bringing that some enthusiam into her writing, Reboe proved that fandom isn’t just a hobby; it’s a source of power that can redraw the map of pop culture.
About Our Host
Jenna Wrenn began her career in entertainment journalism in 2022 as a reporter and editor for Temple of Geek, getting a late start on her childhood dream of being a professional writer. She has bylines as a Features Writer at ComicBoook, Senior Comics Reporter at Screen Rant, CBR, and Anime Fire.
Jenna is a seasoned podcaster and the host and executive producer of Portrait of a Fangirl and the co-creator, co-host, and executive producer of Femsplaining. Her work has led to moderating panels for Webtoon at New York Comic Con with acclaimed artists like Rachel Smythe of Lore Olympus — a creator who has inspired Jenna for years. Jenna has also served as a panelist for Portrait of a Fangirl at San Diego Comic-Con 2024.
Jenna is a historian by trade, a writer by passion, as well as a cat mom by birthright. She loves to travel, forge new connections, and also drink large cold brews. Jenna is excited to bring more fascinating interviews to viewers/listeners of the Portrait of a Fangirl podcast.
Listen to the rest of season 3 of Portrait of a Fangirl Podcast
Check out episodes from season two of the Portrait of a Fangirl Podcast
- Episode 20: A Conversation With Voice Actor Briana White (1/10/25)
- Episode 19: The Recipe for Success with Chef Mary Lou Davis (10/17/24)
- Episode 18: What is Post-Con Depression and How to Cope (9/27/24)
- Episode 17: A Conversation with “The Lovers’ Author Rebekah Faubion (9/13/24)
- Episode 16: The Ripped Bodice: How Women Are Reclaiming the Romance Genre (9/5/24)
- Episode 15: From Fangirl to Sci-Fi Icon: A Conversation With Katee Sackhoff (8/16/24)
- Episode 14: Candice Miller, Audience Winner at the 2024 Her Universe Fashion Show (7/30/24)
- Episode 13: Wes Jenkins Wins Her Universe Fashion Show With Barbie-Inspired Design (7/29/24)
- Episode 12: Interview: Raeven K, Winner and Judge of the Her Universe Fashion Show (7/22/24)
- Episode 11: Journalist Laura Sirikul on Balancing Professionalism and Fandom (7/14/24)
- Episode 10: Blazing Your Own Path in Fandom (7/8/2024)
- Episode 9: Ashley Eckstein on 10 Years of the Her Universe Fashion Show (7/3/2024)
- Episode 8: Micahel James Scott Returns for the Her Universe Fashion Show 10th Anniversary (6/27/2024)
- Episode 7: Breaking inot Hollywood Writing with Victoria Male (6/8/2024)
- Episode 6: FeliciaDay3D: Bringing 3D Printing, Tabletop, & Geek Culture Together (5/24/2024)
- Episode 5: Beyond the Stereotypes: How TikTok Star Shiv Reddy is Changing the Narrative (5/18/2024)
- Episode 4: From Retail to Red Carpet with Amanda Castrillo (4/25/2024)
- Episode 3: The Evolutions of Fangirling with Tara Sands (4/16/2024)
- Episode 2: Fandom as a Window to the World with Alice Fanchiang (3/29/2024)
- Episode 1: Fandom in Academia With Dr. Sabrina Mittermeier (3/15/2024)
Check out season one of the Portrait of a Fangirl Podcast
- Conversation With Author EK Johnston (11/10/2023)
- Rachel Smythe Roundtable Interview at New York Comic Con 2023 (10/19/2023)
- Inclusivity and the Authentic Self in Content Creating (10/3/2023)
- Emily Zemler on “The Nightmare Before Christmas: Beyond Halloween Town” (9/8/2023)
- Kayleigh McKee on Creativity, Industry, and Personal Growth (9/1/2023)
- Fandom From Behind the Scenes – POAFG Podcast (8/15/2023)
- Discussion With Graphic Novelist Ghezal Omar (7/20/2023)
- The Art of Fangirling With “Let’s Play” Creator Leeanne Krecic (7/19/2023)
- Interview with Ashley Eckstein – Her Universe Fashion Show (6/28/2023)
