Hidden Gems: Meet Terrence Phillips of Awkward Monday

Today we’d like to introduce you to Terrence Phillips

Hi Terrence, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
My name is Terrence, and the story of how I started Awkward Monday is pretty funny. I went back home to California for a few weeks just as the world was opening up again after Covid. I’ve always been a high-energy person who loves social media, hanging with friends, and partying, so I ended up on an accidental 14-day bender with my friends. No regrets—those two weeks were full of amazing and crazy stories!

Afterward, I thought, ‘Hey, we should start a podcast called The Weekend 6.’ But with me in Missouri and my friends back in California, it was hard to make it work. Plus, they all had ‘real’ adult jobs, and I didn’t yet. So, I decided to create something on my own. The name ‘Awkward Monday’ actually came from my friend Kat, who just said, ‘Why don’t you call it Awkward Monday?’ It stuck—and it definitely catches people’s attention!

Since I love throwing events and sitting around talking with friends, I figured, why not turn this into something bigger?
So, I started taking my camera to the bars, snapping pics and recording videos, and just sharing them online. Before long, I got pretty good at it and started building a following.”

Here’s a polished version that flows with the rest of your story:

Now, I have the pleasure of working with some amazing people, all of us aiming to take Awkward Monday to a nationwide scale.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
None of this has been a smooth road—being an entrepreneur is one of the scariest things you can do. There’s no one to fall back on, and not everyone believes in your vision the way you do. Competing with bigger companies that have more money and experience is tough. But I love going through this process, because one day, all the hard work is going to pay off. I also think my lack of consistency has held Awkward Monday back. While building this company, I’ve been working a day job that has me putting in 10-12 hour days, five days a week—including every Saturday. Juggling both means my time is really limited, and that’s definitely made things harder.”

Appreciate you sharing that. What should we know about Awkward Monday ?
What is Awkward Monday? We’re a media entertainment company based in Kansas City, Missouri, known for creating unforgettable weekends. We specialize in events and podcasts that bring people together. One event I’m especially proud of is our Crawling Santa bar crawl, which perfectly represents who we are as a company while giving back to the community.

What sets us apart is our focus on making every event consumer-friendly. I’m always looking for ways to keep our ticket prices affordable, so people can enjoy the experience without breaking the bank.

Are there any apps, books, podcasts, blogs or other resources you think our readers should check out?
Honestly no! I think what helps me is just knowing im not where I want to be yet.

Contact Info:

• Website: https://Crawlingsanta.com
• Instagram: https://www.instagram.com/awkwardmonday?igsh=MXg5bHdobnhtNTdrNw==
• Youtube: https://www.youtube.com/@Awkwardmonday