Life, Values & Legacy: Our Chat with Ray Roberts of Uptown

Ray Roberts shared their story and experiences with us recently and you can find our conversation below.

Ray, so good to connect and we’re excited to share your story and insights with our audience. There’s a ton to learn from your story, but let’s start with a warm up before we get into the heart of the interview. What do you think is misunderstood about your business? 
When people think about comedy as an industry right now, they are pretty polarized. Especially when it wades into the political realm. Conveniently that’s my favorite type of comedy to do is to take big, scary things and make them more digestible for regular people. What’s more scary than the government taking over the city you live in? However, I do understand that people would like a break from the real world and I do my best to deal with these scary things in an approachable and non-preachy way so as many people as possible can enjoy themselves while also seeing a side of issues they maybe didn’t think about.

Can you briefly introduce yourself and share what makes you or your brand unique?
I am a stand up comedian based out of Chicago, Illinois. I like to think that I run a less needy and attention starved “business” than a lot of other people in my field. I pride myself in putting out more quality than quantity and building in a real life grassroots way. Anyone can ride trends but over here at Raycorp (my fake corporation name for my nonsense) we are dedicated to being good over being seen. It’d obviously be awesome to be both, but if we have to choose we’ve made our choice.

Great, so let’s dive into your journey a bit more. Who were you before the world told you who you had to be?
I, like most people, was way more flexible and happy and fun loving before the world got involved. Everyone from your parents, to teachers, to the TV tell you how to act and react to the world around you and that changes how you act and think. Over the past few years though, I’ve been reclaiming that part of myself the world tried to take away because the world actually wants YOU not what you think the world wants you to be.

If you could say one kind thing to your younger self, what would it be?
Trust yourself. There were many times in life where I made the “right” choice despite it feeling wrong and it has always come back to bite me. Follow your compass for what you think is right as long as nobody gets hurt from it.

Sure, so let’s go deeper into your values and how you think. Is the public version of you the real you?
Yes. Is it maybe a ramped up version? Sure. I might not be as aggressive or outspoken when I’m in a private setting but if you see someone change up how they act or treat people when the lights are off, it’s time to stop being around that person.

Okay, we’ve made it essentially to the end. One last question before you go. What will you regret not doing? 
Asking for help or calling in favors that you’ve earned earlier. People are usually more open to helping you than you think and for a long time I though it was weak to ask for help. It’s not a weakness at all, it actually shows a lot of strength to understand you can’t lift the whole world by yourself.

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