We had the good fortune of connecting with Ryan Fleming and we’ve shared our conversation below.

Hi Ryan, how do you think about risk?
I am a very analytical person and use that part of my mind for my daytime work in affordable housing/housing finance to assess risk and the financial viability of affordable housing developments for the State of Georgia. However, for personal endeavors, like pursuing my career as a standup comedian, my assessment of risk is often more of a gut reaction. When the fear of not taking a chance starts to eat at me and mount up to something that causes more anxiety than the thought of actually making the attempt itself (even with likely failure), that is when I know it is time to try something scary. I remember my first attempt at stand up comedy (even the faces of those strangers in the front row staring at me). For most of us comics, you basically black out the first time on stage and forget most of what you said (or want to forget it). It is a very scary proposition to stand in front of a room full of strangers and try to turn silence into laughter. It is kind of like learning to ride a bike for the first time while an audience who paid money watches you stumble along for a couple feet at a time as you try to balance on the comedic pedals. But, the accomplishment of looking fear straight in the face that first time and trying to elicit laughter from strangers energized me enough to keep going again and again.

In the past year, a couple major life events have shaped the way I see risk as well. Through these events, I have learned that risk is always present whether you choose to try something new every day or try to protect yourself at all times. Life is inherently dangerous and risky. Last August, my apartment building burned to the ground in Atlanta and everything I and over one hundred other people ever owned was lost forever. In January of this year, I almost lost my life in a car accident in Indiana on the highway traveling for the holidays from my childhood home in Milwaukee. Luckily, I only needed hand surgery and fractured a bunch of ribs (yes I actually do mean luckily).

Both of those events taught me that life is full of danger and risk, whether you are pursuing your goals, hopes, and dreams, or not. There were moments where those events made me want to minimize the chances of the unknown from creeping back into my life, but after further reflection those events have freed me mentally to face fear and continue to pursue my goals in comedy. No one gets to pick a path which results in growth without any risk or opportunity for failure, so you might as well follow your gut, and listen to it when it tells you not taking a risk is eating you away. I have to keep reminding myself of this every day. Risk, and the fear that accompanies it never goes away. But my capacity to face it grows each time I decide to take a chance.

Let’s talk shop? Tell us more about your career, what can you share with our community?
It would be odd to hear a straight, white male in his late 20s say he is often a fish out of water. But my life has often been just that, an attempt at walking on land. I love being around people who grew up differently and most importantly, don’t think like me. Growing up my best friend was black and I have made many black friends in the comedy scene in Atlanta. After grad school, I lived with two gay guys. The majority of my bosses in my professional life have been women.

Hearing different perspectives and seeing how people live and think differently has informed my opinion on the world and impacted my comedy a great deal. In comedy, when the crowd does not look like you or comes from a different background, you have to find common ground quickly and make fun of different groups of people without stepping over the line. I think what distinguishes me from other comedians is my ability to relate to different groups of people by flirting with the line of appropriateness, while making people laugh together about their similarities and differences.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
I would take my friend to a few stand up comedy clubs in the city: Laughing Skull and Uptown Comedy Club in particular. We would go for a walk along both the Eastside and Westside Beltline and check out Piedmont Park. We would also need to make a trip out of the city to North Georgia to go hiking in the Appalachians.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
My fiends and family pushed me to try stand up comedy for several years before I gave it a shot. A very big shoutout to my parents and brother, along with a guy named Nico in grad school who instilled so much confidence in me that I could do it, I gave it a shot.

Instagram: @rooreddy

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