The Video Trifecta from Teddy Robb

“Really Shouldn’t Drink Around You”

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“Lead Me On”

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“Tell Me How”

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You can learn a lot about a new artist from his or her first music video. So when a guy walks into the country music scene with three videos? He’s pretty much an open book. That’s how we think you’ll feel after watching newcomer Teddy Robb’s first, second and third videos, and reading all about his conversation with First, tell us about your journey from Akron to Vail. What made you want to call Colorado home? Was it hard leaving your home in Ohio? How did you make a living?

Robb: I love Akron, Ohio, and it was tough to leave. I have incredible friends and family there. That being said, it has always kept me focused. I knew I was making a sacrifice to be doing what I love. From the time I was a kid I had always been fascinated by the mountains and ski towns. When the opportunity came to move out there, I wasted no time packing my bags! Bucket list! I made a living playing music at a few different bars and hotels: Pepi’s, The Ritz Carlton Beaver Creek, Shakedown Live Music Joint, Beano’s Cabin and more. I spent one full year there before heading back to Nashville.

Okay. Now tell us about that journey from Vail to Nashville.

Moving back to Nashville was always in the back of my mind. I just didn’t quite know how or when. Music Row had always seemed impossible to break into. I was actually at Pepi’s in Vail, eating a cup of soup to warm up from the cold, when a group walked in looking for a table. I happened to have a couple extra seats at my table and offered for them to sit down. After getting to know each other for a bit, one of them asked what I wanted to do with my career and I responded with, “I want to be a country music artist.” Turns out, one of the guys was in the industry, and before I knew it I was connected with one of my producers, Ben Fowler, and I was moving to Nashville. Just goes to show you should always give up your seat!

Your bio says that George Strait was an influence, and then on Instagram you’ve revealed a couple more: Gary Allan and John Prine. What is it about their music that was the influence: the way they sing, the lyrics they write, or something else?

I am always drawn to a vocal that has conviction and a lyric that is believable. Artist like George Strait and Gary Allan make me believe in what they’re singing. Hearing George sing “Troubadour” for the first time really changed my perspective on life. I knew when I heard it I had to keep pushing forward in my music career.

You also mention on social media that your goal was always to be a traveling musician. Now that you’re doing just that, is it everything you imagined it would be? Any down sides to it (yet)?

Being a traveling musician is even more than I imagined. I am constantly pinching myself that I get to do this.

What do you hope listeners will learn about you from these first three videos?

These three videos are an opportunity for listeners to begin the journey with me. It’s kind of a way to catch everyone up to where we are now: in Nashville, working every day to make great music.

Tell us the story behind the day you wrote “Tell Me How” and “Lead Me On,” and how you found your first single “Really Shouldn’t Drink Around You.”

I wrote “Tell Me How” with Blake Chaffin and Aaron Eshuis. The song came about after we all got into a discussion about how difficult it is to not talk to your ex while going through a breakup. When you love someone they often times become your best friend, and when you break up you have to cut that line of communication off. “Tell Me How” is about that struggle and some of the questions I would ask her if I could.

I wrote “Lead Me On” with Matt McGinn, Aaron Eshuis, and Ryan Beaver. We wrote the song about how even though it may hurt, being led on is better than not being led on at all. At least this way, we may have a chance in the end. The idea kind of started when I met a girl in line at a show. We had chemistry, and had a really great night together. The next day she called me to tell me she didn’t want to pursue anything, and for a brief moment I thought, man I wish she would have just led me on for a bit so I had a chance to change her mind.

Shane McAnally, Josh Osborne, and Trevor Rosen wrote “Really Shouldn’t Drink Around You.” When I first heard it, I immediately connected with the song on so many levels. I think we can all picture that person we shouldn’t drink around. I love playing it live and feeling the crowd’s reaction. It’s such a relatable lyric.

Where were the videos shot?

The videos were shot in a cabin about an hour outside Nashville. I started thinking about the concept of “Lead Me On” when I was still living and playing music in Vail, before I came to Nashville. Because of that, we wanted to give that video a Colorado Ski Town feel with the mountains in the background and the cabin. When we decided to make all three videos a series following one relationship from start to end, we decided to film all three videos at that location over three days.

What was the worst gig that you’ve ever played that made for a good story later?

I played two gigs in one day in downtown Nashville — eight hours of music — just to find out I got a parking ticket and my car was towed. I lost money that day.

What was your first Nashville gig?

My first gig in Nashville was on Rippy’s roof and I was terrified, excited, green, and had no idea what I was in for!

What has been your most interesting side hustle?

I interned at a country radio station in Akron, Ohio (FM 94.9 WQMX) as a part of the marketing team. I got to see Thomas Rhett come into the station and I thought to myself, “That’s what I want to do.” It wasn’t very long after that when I moved to Nashville.

Robb’s next stop on tour is on May 1 in Oxford, OH at Miami University’s favorite country bar, Brick Street Bar.

Alison makes her living loving country music. She’s based in Chicago, but she’s always leaving her heart in Nashville.