Kyle Smith — Meeting Him, Playing Cali Roots Together, and Watching Him Inspire a Generation of Musicians

Brendan Clemente
6 min readFeb 28, 2022

I first connected with Kyle Smith for one simple reason…

I was too afraid to play the California Roots Festival alone.

I wanted to play an acoustic set at the fest, but was concerned I wasn’t a big enough artist to play it by myself. I was also nervous about being onstage without anyone else — the thought of hundreds of people watching just me scared the shit out of me.

This was back in 2019. I had watched curiously as Kyle took the reggae/rock scene by storm, marketing his music and memes in the Facebook groups of the biggest bands, while cultivating his own fan group at the same time.

As a fellow musician in the scene trying to get my music out to the world, I was very intrigued by the way Kyle marketed himself. He would speak openly about everything from his past addiction struggles, to masturbation habits, to frustrations with his music career… I think that really gave people the sense that they personally knew him.

He also just wasn’t afraid to say shit that everyone else would never say or admit publicly; it wasn’t the same old boring, “Look at me, I’m making music, please care about it”.

He’d say stuff like (please note that I made this up as an example, it’s not an actual quote from him)- “Fuck — I stayed up until 3am surfing Youporn last night, got up at 7am for work today, worked until 5pm, drove 3 hours to play an open mic, and no one showed up… you can say a lot of things about me, but I’ll do anything to fucking make it in music.”

Stuff like that is a million times more interesting than saying something like, “Open mic after work today — tired but blessed to be doing this!”

The amount of work and thought that he put into social media is inspiring and amazing — it’s something that any artist who wants to market themselves better could learn from. Before long you couldn’t look anywhere in our scene on social without knowing who he was.

And whether you loved or hated his style (there were definitely several moments of drama and backlash along the way), he was unapologetically himself from the start, and became a master of telling his story in an entertaining way that got people to rally around him.

Although even I admittedly didn’t personally love every one of his posts, you can bet your ass that I respected every minute of his work, hustle, and unwavering confidence.

Anyways, back to Cali Roots 2019…

In short, I saw that Kyle was busy making a splash in the scene, and immediately had the sense from his persistence and attitude that he’d be a name people all around the world would know sooner or later. I was super inspired by his story and confidence, and thought he’d be a perfect person to play the festival with.

I had a personal connection with Cali Roots, and knowing that Kyle really wanted to be there playing it, I sent an email to the fest one night and asked if they would allow me and Kyle to play a little acoustic set in the arts area.

To be honest, I figured they’d either say no, or that this would just be us sitting on a curb and jamming a little bit — nothing major. That’s why I was blown away and panicking when the festival responded and said they’d do us one better, and allow us to jam an official acoustic set, taped by Sugarshack Sessions.

To understand the gravity of the situation, because I had just thought it would be something small, I hadn’t even asked if Kyle would play the set with me yet — I’d just gotten us a gig that he didn’t even know about. Not to mention, we’d never played together before.

I messaged Kyle on social and said I needed to chat about a show opportunity. Later that week we hopped on a call and I told him I got us an acoustic set at Cali Roots. He couldn’t believe it at first, and said,

Like, at the actual festival? Like we’d be on one of their stages getting taped?”

Yup”, I answered. “Completely official.

I could tell that Kyle was both surprised and stoked, but to be honest, I think we were both wicked nervous.

Whose songs would we play? How would we learn each other’s songs? How would we practice being that he lived in California and I was in Minnesota? What if we just embarrassed ourselves up there?

In addition to all that, I realized that in my haste to ask about jamming with Kyle, I had neglected to mention anything about his amazing band (Scotty Brown and Christopher Nishida). Would they be able to jam with us too?

There was a lot of shit to figure out, and this wasn’t some open mic night that we could just wing — there would be hundreds of people watching us at one of the biggest festivals in the scene.

It ended up not being feasible having the whole band, and in order to get at least somewhat of a set together, I flew out to Ventura 5 days before the festival to stay with Kyle and teach each other some of our songs. We basically practiced for 24 hours straight and that was that.

It was a small miracle, but with a lot of work and a bit of stress we pulled it off. And despite the fact that Cypress Hill was crushing it across the festival grounds while we played, several hundred people still showed up to support and watch us. That’s a moment I’ll never forget — the people who were crazy enough to miss Cypress Hill to see us — I think we’re both eternally grateful for that.

When we finished playing I hugged Kyle and smiled. “Sorry again about surprising you with this man — next time we’ll have it more planned out” I told him.

Man, please never feel bad about bringing surprises like this into my life”, Kyle replied laughing.

And now here we are a few years and a global pandemic later. Kyle’s playing main stage at festivals, touring with bands like The Elovaters and Arise Roots, and really starting to hit the stride him and the band have worked so hard to achieve.

But perhaps most significantly, Kyle did something that the majority of musicians either never find the courage or momentum to realistically do: he left the security of the day job he’d held for years so he could go all-in on his dreams.

I know myself and a whole lot of other musicians are rooting him on and taking notes — his inspiration can be seen in all the comments on his posts, from who have been helped with everything from addiction to growing their music careers.

If you ask me, Kyle, Chris, and Scott are just getting started, and this will be the beginning of what I hope is a long, beautiful career of selling out venues and seeing all the success they dream of.

With every day that goes by, Kyle’s marketing slogan “Who the F*ck is Kyle Smith?!”, a sarcastic expression he used to poke fun at himself for marketing a name no one really knew during his early career, becomes less relevant as more and more people across the scene know who he is (though I suspect the community will keep this one alive for the long haul — it’s way too fun to say).

As for me, I’ll be right here cheering Kyle on during every step of his journey. Most people don’t know how much blood, sweat, and tears it takes to actually make it as a musician, and I respect the hell out of anyone crazy enough to try it.

I look forward to sharing the stage with Kyle again someday, and making music until we’re both old men reminiscing about the good ole days. In the meantime, Kyle just started a Patreon — go show him some love and support!

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