Garrett Phillips is a humanist humorist or vice versa, born and raised in Canton, Ohio. He lived nearly thirty years in Atlanta and most recently lived in Los Angeles pursuing writing and podcasting projects before COVID-19 ran him out of town. Currently in Richmond, Va., near family.

The author created The Tree Fort Report podcast, which he has hosted and produced since March of 2020. Phillips formerly occupied himself as an on-air morning radio talent, stand-up comic, courier, golf instructor, waiter, video blog host, and chauffeur, among other follies. He attended Georgia State University and always wants to hit a golf ball.


Q&A for Lookout For Shorts: A Prison Memoir

Q. When did you decide to write a memoir?

A. You could say the memoir decided on me more than anything. The state of North Carolina provided three years of research for the book, free of charge. Who was I to say no?

Q. The cover delivers a cartoon-ish, South Parky vibe. Is the story a comedy?

A. I like to think so, at least mostly. As with most creative types, I use humor to mask pain. The slammer pretty much demands this, so the theme chose itself. I learned that no matter how low my situation gets I can still laugh.

Q. What was the funniest thing that happened in there?

A. Probably when a fellow felon got drunk at his work-release job and wandered off to find a crack house. He became cop cam footage and appeared all over the TV news and newspaper. The joint was lit rehashing that for a while. But God knows a million funny things happened. Enough to fill a book, you could say.

Q. What about the more serious events? Were they difficult to write about? If so, how did you deal with it?

A. I detailed a lot of background about my life, explaining how I put myself in the position to start dealing drugs to dig out of debt. This invited feelings of regret, to say the least. When writing, I just tried to plow through it. I assume sitting around in prison wallowing in regret for three years helped make it less difficult when writing time came. I’d already been over it so many times by then.

Q. What surprised you most about your prison experience?

A. Probably how many “tough guys” like to rock out to pop music. Seeing a tatted-up dude in for manslaughter singing along to Taylor Swift happened pretty often. Also, how often I transferred camps in less than three years. I endured over forty different bunkmates. Inmates get moved around a lot, especially at the minimum security level.

Q. How long did the book take to write?

A. About five years, but not working on it constantly. The first seventeen months following my release I wrote and edited pretty much every day because I didn’t have a real job. I lived with relatives who let me repay them later. Once I’d moved on to working for a living, I wrote and edited when I felt like it. This worked out well because setting it aside helped me see it with fresh eyes when I picked it up again.

Q. Were you trained as a writer?

A. Aside from a ton of personal journal and travel blog entries, no. I took a 101 class in college before I dropped out, but before this project I just picked up tips here and there. I have a knack for writing basics, and storytelling, but any high-quality prose found in Lookout was hard-earned.

Q. How so?

A. Throughout endlessly fine-tuning the manuscript I used an invaluable peer-to-peer critiquing site called Scribophile. I edited many other writers in exchange for their help on my work. Doing that off and on for three years was both fun and made my writing more concise and lively. I suspect that hands-on experience is equal to a series of quality writing courses. Not to mention it provided free editing services! Very time-consuming, though.

Q. You self-published Lookout For Shorts. Good or bad idea?

A. So many pros and cons! The good news is the physical quality of the book is on par with traditionally-published ones. I lucked into a great cover/interior designer named Euan Monaghan, too. I found him via Reedsy, which is an amazing resource for self-publishers. Not needing to find an agent and wait a year or two for the book to reach the market was also nice. On the other hand, the out-of-pocket costs are a burden and marketing/ promotion is a bitch of a job. I guess time will tell if I made the right choice.

Q. The acknowledgments page of the book mentions longtime Vanity Fair editor Graydon Carter. This seems like bullshit. What gives?

A. That dude hooked me up! I sent him a letter with a story suggestion and joked that I’d be out in time and available to attend the 2015 Vanity Fair post-Oscars party. He didn’t reply but got someone in his mailroom to send me a dozen or so promotional books. One of them was Confessions of a Call Girl, or something like that. Great trade bait in the slammer!

Q. You namecheck extensively in this book, in all sorts of directions. Why?

A. Gratitude. Every mention is of people or things that helped me through a cultural and intellectual drought. I took a lot of excellent radio shows and magazines for granted on the outside. They made me so happy on the inside that they deserved a nod. They made me feel like I was stealing time from The Man.