Meet Ryan Rud

We were lucky to catch up with Ryan Rud recently and have shared our conversation below.

Ryan, so great to have you with us and we want to jump right into a really important question. In recent years, it’s become so clear that we’re living through a time where so many folks are lacking self-confidence and self-esteem. So, we’d love to hear about your journey and how you developed your self-confidence and self-esteem.

I was a shy kid. I had friends and what not but I was always a shy kid and never really had a lot of self confidence. We could go into reasons why but I’ll leave that to my therapist. Anyways, It wasn’t until I started playing music that I began to cultivate a little self esteem and confidence. Music was mine. It became the “thing” that I was actually good at. I believe we all have that “thing” that we are passionate about and excel at. Music was that thing for me. Since I was shy and didn’t say much, music allowed me to speak without actually talking. A way to show people who I was with a safety barrier of sound. Music protected me. It gave a space to really find who I was and who I wanted to be.

The more my band wrote, recorded and performed it felt like those layers of self doubt just kept slowly peeling away revealing more of myself. My confidence just kept growing. This spilled over into other aspects of my life. I started to feel more comfortable around people. Music is a very dear thing to me and I figured if I’m willing to give something that is so special to me to others, how bad could it be if I started sharing other aspects of my life with people. Crowds got more comfortable for me. Conversations became easier. I think that all laid the foundation for where I am now in radio.

After decades playing in the local music scene I started doing radio. I started a radio show with my brother called The Rabbit Hole and last year we started Rabbit Hole Radio. Rabbit Hole Radio is an internet radio station that streams music 24/7 and has other podcasts/radio shows sprinkled in at various times. The Rabbit Hole being one of those shows. I love it.

Radio became something very similar to music for me. It allowed me the space to even further explore who I was. I found a different voice. I also found I was pretty good at it. After a youth spent trying to find my voice I can now talk with anyone. With The Rabbit Hole and Rabbit Hole Radio I wanted to build a community. Soon people started coming to me asking to be on the show and have their songs on the station. As The Rabbit Hole grew, so did my confidence. If you would’ve told me when I was 12 that I’d grow up to have a radio show and that I’d run a radio station I would have thought you were nuts, but here we are.

If I could offer some advice to young folks…Find your passion. That thing that makes you feel alive. That thing that you know in your soul that you excel at. That thing that inspires you and helps you stand tall and confident. We all have it. Find it and feed it every day.

Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?

What do I do? Great question. I do a lot…I’m a husband, father, musician. What I’m most focused on right now, besides the aforementioned things, is my radio show “The Rabbit Hole” and running Rabbit Hole Radio.

Let’s start with the radio show, “The Rabbit Hole”. The Rabbit Hole is a weekly LIVE radio show hosted by myself and my brother Matt or “Mattchew” as he’s more commonly called. It’s Thursdays at 8pm CST on our internet radio station “Rabbit Hole Radio” on the Live365.com platform.

The unique thing about The Rabbit Hole is many fold. First, it’s live. there’s no safety nets, no edits, and it goes over the airwaves as it’s happening. It’s old school radio. In a world of prerecorded podcasts that take the best moments and stitch them together (nothing wrong with that FYI), The Rabbit Hole is a throw back to days past where you get the entire show as it is. I like to think it’s an experience. It’s a moment in this collective space for all who were there listening at that specific time. If you were there? Great. If you missed it? Sorry. Tune in next Thursday I guess.

We chat about our lives, play music, have guests, talk movies (mostly 80’s teen comedies), and will discuss just about anything that comes to mind, except politics. We are a politic free zone. There are a million other places you can go to discuss and debate politics to your hearts content. The Rabbit Hole is not that place. We like to think of ourselves as a safe haven from that for 2 hours every week. Sit down, have a cocktail, put on a supper coat, laugh and take it easy for a few hours.

A supper coat? Yes, a supper coat. Some may call them a “dinner jacket” or a “blazer”, but down here in The Rabbit Hole they are supper coats. In fact a supper coat is required to even get into The Rabbit Hole.
Yes. My brother and I have a dress code for our radio show. I’ll say it again, we have a dress code for our radio show. And yes, our guests must adhere to the dress code as well. Why do we have a dress code for a radio show you might ask? Because it’s fun. It’s our one time a week my brother and I get to sit down, have a few cocktails, talk about whatever, and look really really good while we do it. It’s sort of like our weekly radio bookclub. Over the past 5 years we’ve been doing this, it’s evolved and we kind of created a bit of a lifestyle for the two of us. On the show? Supper coat. Out in public? Supper coat. Between Matt and I we pretty much have the vintage mens supper coat market cornered in the Twin Cities area. We both have extensive collections. Extensive. Collections.

In the words of Ron Burgundy, “It’s boring but it’s my life”.

But wait! There’s more! The Rabbit Hole is not only our radio show but it’s a specific location. The Rabbit Hole is the room in my basement dedicated to the show, my music, and any other Rabbit Hole Productions related thing. It’s where the radio show is broadcast and is the central hub for Rabbit Hole Radio as well.

The Rabbit Hole is definitely a vibe. I call it “vintage 70’s thrift store chic”. Dim 70’s era lighting, Bob Ross-esque paintings, velvet chairs to sit on and a fully stocked bar for cocktails. The Rabbit Hole is an experience. Not just for our guests but for both Matt and I every Thursday night. We definitely settle down and take it easy on Thursday nights and we invite our guests listeners to do the same and share those two hours with us.

Earlier this year, after about 4 years of The Rabbit Hole broadcasting on another platform, Matt and I started our own radio station. We’ve always had full control of our radio show but we wanted to also have full control over the music and programming around The Rabbit Hole. So in February of 2025 Rabbit Hole Radio was founded on the Live365 platform.

Rabbit Hole Radio is 24/7 radio. There’s a lot of diverse music, mostly from genre’s that Matt and I love and grew up on. We play 50’s, 60’s, Motown, classic country, a lot of 80’s and 90’s, yacht rock, just about all genres. We also play a lot of local Minnesota artists. I’ve been a musician in this scene for a very long time and we try to elevate our stellar music scene as much as we can. We also have other dedicated programming on Rabbit Hole Radio at various times throughout the week. Most of the time our playlist is very random. You could be listening to Little Richard and go into Waylon Jennings or Soundgarden or even Frank Sinatra. It feels like the days when you would wait by your boom box with a blank cassette in hopes of recording your favorite songs. Praying the DJ doesn’t talk too far into the intro of song.

I absolutely love running Rabbit Hole Radio and doing The Rabbit Hole. I always wanted to be in radio and it’s kind of cool that we’re able to this have the kind of freedom that we have. One of the bonuses of modern technology i guess.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

Three qualities? Wow. I’ve never thought about that to be honest. I’ve always been the kind of person that gets an idea and then just jumps in and figures it all out on the fly, for better or worse.

So first quality? I guess you have to be a bit fearless. I don’t worry about failure most of time because it’s the experience that is the payoff anyways. I learned from my dad that mistakes are learning opportunities and a way to get better at whatever it is you’re striving to get better at. People are sometimes afraid of the unknown and I think that can be a barrier for some to take a chance and try the things they always wanted to try. I honestly don’t know where The Rabbit Hole and Rabbit Hole Radio is going but I have a strong faith that the universe sorts that stuff out and will provide us with opportunities that will take us where it’s intended to go. So be fearless in your passions. Remove that fear and just do it. Sounds cliche and I hope Nike doesn’t sue me, but yeah, just do it be fearless about it.

Second quality? Hard work. My dad had an excellent work ethic and I apply that same ethic to the show and to the radio station. I work really hard at it and I see it pay off all the time. It may not always be as fast or as big a payoff as I’d sometimes like it to be but that also keeps me wanting to keep trying new things and get better at this craft of radio. I think about The Rabbit Hole all the time and how I can make it better. It pushes me and stretches my mind. It’s fun and I love it. When that ceases to be the case, I’ll stop. But in the meantime I’m going to put in the work.

Third quality? Be yourself. This world is full of BS and nonsense and people being someone other than themselves. Matt and I are not playing characters on Thursdays. What you hear is who we are. We like to laugh. We cry. We love music and John Hughes movies. We love our friends and family. We like to dress nice and drink good bourbon. But above all that we are good people. The Rabbit Hole has introduced us to so many fantastically good, kind people. Our goal with all of this was to create a community of good people. Creative people, funny people, musicians, small business owners, and just plain good people. If we’ve shared time together then we consider you part of The Rabbit Hole Family. We mean that. The cool thing is the family keeps getting bigger.

Is there a particular challenge you are currently facing?

We’re an internet radio station and LIVE radio show in the day and age of podcasts and streaming services. We ask people to tune in and let us decide what music they are going to be listening to. We’re asking folks to tune in specifically at 8pm on Thursdays to listen to The Rabbit Hole. It’s a big ask especially when they can just open Spotify and craft their own very specific playlist or listen to any podcast at a time that’s most convenient for them. Is this a challenge to overcome? Sure. But I think that’s what also makes us unique.

We’re all about experience and community in The Rabbit Hole. Maybe you were listening and happen to unexpectedly hear a song that brought you back to a time that made you smile? Cry? Laugh? Who else was listening at that same time and felt the same thing? Matt and I are music lovers and are moved by it every single day. We want to share that. We’re human here at Rabbit Hole Radio. There’s no algorithms. It’s run with care, intent, and love. You may not get to pick the playlist but we guarantee you’ll hear something you’ll enjoy. You may find something new. There’s community in that.

Yes, running this particular model and idea of radio show and radio station is not the most common way. But it’s different and it’s got a lot of heart and soul to it. Stop by sometime and stay as long as you’d like, we’ll be here wearing a supper coat with an old fashioned in hand.

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