Alright – so today we’ve got the honor of introducing you to Alan Giles. We think you’ll enjoy our conversation, we’ve shared it below.
Hi Alan, thanks for joining us today. We’ve love to hear an interesting investment story – what was one of the best or worst investments you’ve made? (Note, these responses are only intended as entertainment and shouldn’t be construed as investment advice)
I believe the best investment I ever made for my creative and personal growth was moving to Chicago.
I arrived in Chicago sight unseen in September of 2013. I went there because halfway through my senior year of high school, I ran into Adam Archer, my former improv teacher, who had recently made the move from our hometown of Columbus, Georgia to the Windy City. “It doesn’t matter where you go to college,” he told me on a sidewalk outside of a bike shop. “If you want to do comedy, just go to Chicago.”
So I did.
At 18 years old, my parents moved me into my dorm room in South Loop and left. On my second night in the city, I took the Red Line up to Wrigleyville to watch Adam perform in an improv show at iO Theater, and then I was doomed. I loved it. I obsessed over it. Within a month, I had signed up for classes and started picking up midnight tech shifts at the theater so I could watch shows for free. I was young and in the big city, and my life was just starting, and it was everything.
Chicago is a special city because it has a dense population of creatives, but without as much “industry” presence as NYC and LA. This makes it the perfect place to study, learn, fail, and grow. I would do a show in front of an audience of 100+ one night, and then the next night, do a show for an audience of two. Both experiences are valuable.
I met my best friends, many frequent collaborators, and my wife in Chicago. Though I live in LA now (and love it), I credit Chicago for building me into the artist I am today.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.
I am a comedian and filmmaker based in Los Angeles. I fell in love with theatre and performing in high school (my mom was my theatre teacher, so I was a nepo baby) and narrowed my focus toward comedy in college while studying at Columbia College Chicago and The Second City.
Most people would know me for my viral comedy sketch videos online. I frequently collaborate with my friends to make videos about the parking lots at Trader Joe’s, a running club that sings Maroon 5 as they run, and everything in between. I also am a stilt walker and sometimes make videos playing an original character named “The Tallest Man in Los Angeles”. The stilts are one thing that makes me stand out, as there isn’t much stilt-walking comedy out there right now (yet).
I am most proud of two larger projects I completed last year. One is a short film called “The Tallest Man in Los Angeles” and the other is an original solo show I wrote and performed at Hollywood Fringe Festival called “Alan-cadabra”. I’ve been able to show these projects to several audiences and am hoping to have them both available online soon.
The main thing I’d want potential new followers to know is that I cook beans a lot!
IG: @alan_is_tall
Tiktok: @alanfgiles

What can society do to ensure an environment that’s helpful to artists and creatives?
I think we eventually will have to ditch the internet and go back to experiencing the arts IRL as our default. Concerts, comedy shows, plays, art shows, poetry slams, film screenings. These types of events allow us to feel human and create community. Get out of the house and go experience art in the world!

Any resources you can share with us that might be helpful to other creatives?
I wish I had started journaling earlier than I did. I’ve kept a daily journal since 2019, and it has completely changed my life. I recommend it to everyone.
Contact Info:
- Website: https://alan-f-giles.weebly.com/
- Instagram: https://www.instagram.com/alan_is_tall/
- Youtube: https://www.youtube.com/@alanfgiles

Image Credits
Andy Forsberg, Sarah Elizabeth Larson, Monique Hernandez

