-- A flashback to 2018--


“…there is no end game…the goal is being in love with right here, with the process.

There’s a mystic nature to Gainesville’s self-proclaimed lifestyle company, Always True. Founded by three genuine souls with a passion for positivity, the brand is now discovering that it’s in a peculiar position — there’s a definite buzz around the name, but nobody’s sure just where it’s heading. “No matter what we do, there’s somebody there saying that we should do it another way,” said Kevin Masaro, one of three original founders.

That may be a good thing, though.

I sat down with the trio on a rainy afternoon in early November to discuss the company’s identity, among other topics. When I arrived, Kevin was setting up a sign out front while Drew hung wall art — the rest of the town gawked at the university parade going by the window. They were in a rented space; The SL8 Gallery would be their home for the next two weeks. The Always True pop-up shop was revving up for the day.

I didn’t know what to expect — this meeting was only taking place because of a mere Instagram DM. Perhaps that’s how most millennial-run companies operate; maybe it’s just Always True’s organic nature. Regardless, I found myself in a four-man forum on the floor within an hour of arriving. Lo-fi beats played in the background as we settled in — two of us in bean-bag chairs, the remaining two in traditional seats.

While all three of them treat each other with the type of love that only brothers possess, Drew and Sam are the true blood relatives. The pair lost their older brother over six years ago. Brandon Howard, who went under the stage name Always True, was struck by an automobile in Orlando, FL and passed away on August 18, 2012. He was twenty years old.

When Drew, Sam, and Kevin first conceived the idea of starting a lifestyle brand, they weren’t sure what to call it. There were many ideas — one involved starting a fitness apparel company. But once it was settled that they would produce authentic, artistic apparel, a name still had to be chosen. Brandon’s legacy was revived, and the moniker Always True lived on.


To be frank, while I knew of Always True from a distance and was quietly curious, I was only sitting down with them because of their continued rise. A.T. was showing up at local events in Gainesville. I saw people I knew promoting and wearing their garb on Instagram. In my heart of hearts I knew that notoriety led me there. Thus, I began by asking the trio if they’d identified a point in the recent past where their company had jumped up to a new frontier, the next level.

“Where we are right now is exactly where we’re supposed to be,” said Drew. “Obviously we have distinct goals of where we think we want to be, but ultimately we’ve come to the conclusion that we don’t control too much…it kind of just all goes down the way that it does. We still put in the work, we still are here every day, and we’re still here talking to everyone.”

I asked early on in the interview if there had been any arguments in the past, if they all had individual interests that prevailed at times. They quickly shot down the notion. They each had their own artistic tendencies, sure, but no idea was right or wrong. It just was.

I quizzed them on their success. “At times…you feel like you’re on Cloud 9,” Kevin said. But he quickly delved into the dichotomy such success creates. The brand has always evolved, so sticking with one model of success isn’t really in the cards. Drew elaborated: “It’s funny ’cause a lot of people are like, ‘Yo! You’re just goin’ with the flow, that’s not good business!’ — but it’s not go with the flow, you don’t do shit, just sit on your ass — it’s seeing what’s happening, going as hard as you can at what’s in front of you. It’s going with the flow in that essence and pushing as hard as you can within the time that you have, accepting what’s in front of your face and being cool with it and at peace with it.”

Kevin spoke about how those Cloud 9 moments can sometimes overwhelm. When A.T. traveled to New York City and rented out a basement studio to showcase their artwork and threads, the space rapidly filled with local performers and observers. What should have been an environment easy to appreciate turned out to be one that induced anxiety. “What I think I see — it looks like Cloud 9. Because it’s the most interaction, the most stuff involving Always True…everything we wanted.” That seemed to be worrisome to Kevin, at least to some extent. “Sometimes the most ‘Cloud 9 feeling’ is just this.” He spread his arms out towards the room, to all of us. “It’s peaceful. There’s nothing crazy going down, you know? We’re just doing our thing. Chillin’.”

A moment passed. We all nodded in agreement. I clumsily muttered, “Understandable.” Someone got up to close the door, a lizard was spotted, and one of the Howard brothers relocated it outside. I picked up roughly where we had left off.

“How has your personal psyche changed?” I asked. “As individuals.”

“Just dealing with stress…the stress I have in my mind. You can have so many thoughts on where Always True can go. And those thoughts can bring anxiety and stress,” Drew said. “And that sort of freezes you?” I asked. “Yeah, exactly,” he continued, “and it’s seeing that, realizing Holy shit, those things could probably happen, but letting it go and not staying too attached to it. Being more attached to what’s here, what’s in front of your eyelids. That’ll bring more bliss to myself and people around me.”

The whole group was on the same page: they couldn’t give in to their innate controlling tendencies. I pressed on: “It seems that if you had to sum up the brand in one word, that word would be ‘authenticity.’ Is ‘authentic’ a word you’d use to describe Always True?”

Drew shook his head. “Probably ‘peace,’” he said. “Recently we’ve been saying ‘rest in peace’ — based off of Brandon, but taking that and extending it to peace of mind. Everyday. Rest in peace.” In a sense, Always True is out to combat the manic nature of our modern society. I went down an excited rant of my own, but circled back around and inquired whether they were out to give a message, to change people, to mold others. They conceded that it may be a reaction to society, but they weren’t in the business of preaching to folks. Never had they tried to induce the highly sought after eureka moment. They unanimously responded “No” when I bluntly asked if they were out to change people.

“I think what we’re trying to do is nothing crazy,” Kevin explained, “We’re just doing us. We’re staying true to our own path. Even though we are doing this together, we do different things every day. We’re not with each other all day, every day. And that’s with everybody — just stay true to who you are. Follow your own path.”

We were beginning to boil things down to absolute base layers. However, with each layer we peeled off, I had more questions that arose. Does being true to yourself lead to peace of mind? What is the truest form of yourself? If it’s constantly evolving, like Always True, how do you ever know your most authentic self? I had dragged the conversation into the weeds, but Sam was there to attempt to pull us all out:

“It’s about finding yourself through our clothes, I guess. And to just give something for people to feel comfortable with in order to do what they want to do…to use our clothes as a bounce-board to propel the negativity away…to stay true to yourself.”

We were still getting further away from the concrete foundation of Always True, though, into a more philosophical realm that had ideas and answers as slippery as fish lathered with butter. “The world as I see,” Drew said, “there’s everything in front of you, but it’s nothing at the same time. Whatever your thought of Always True is, whatever you think this is, just is what it is to you. At first, we were like ‘Always True…oh, so that means that everybody has to act truthful,’ and now we’re like ‘Who gives a fuck about that?’ Everyday your mind is like I’m this, I’m this, I’m this and your body is like I’m this way now, I’m this shape now. But who really are you?”

“I think we used to think that we knew everything,” Kevin interjected, “We thought everyone was doing it wrong and we were doing it right. But now it’s like, everyone is just doing. We are just here on this earth, trying to figure it out.”


Part of realizing that they weren’t right about everything, that perhaps nobody is ever truly right about anything, was the acceptance of advice from others. But, once again, there are at least two sides to every opportunity. I asked if there had been any corporate interests or souls who wanted to buy into the company and steer it a certain way. Aside from a past fraternity brother who wished to offer seed money in the company’s early days, most of the assistance given now is simply advice. “There’s nothing wrong with taking advice from people,” Drew said. “Some people do know more when it comes to business, but what you do realize is that they aren’t you and they aren’t in your position…You aren’t in their position. I don’t know what they’re doing, what they’ve been through. They’re just giving advice based on what they’ve done. But they don’t know what we’re doing, what our stats are. We appreciate their opinion. Ultimately, it isn’t up to them or even us. It kind of just happens. We’re just the ones doing it.”

All of these ideas we were discussing were so lofty that they often contradicted one another. Yet, it all made sense in a way.

The loose ideas pair well with the way the company does business. Drew explained, “The way we sell stuff is super organic. People either order online and we ship it out of our crib, or people hit us up on Instagram and ask to come by and see what we have at the house.” I wondered if having a brick-and-mortar establishment might benefit them. “I think the pop-up thing is the move,” Drew responded, “Nobody has any idea what the fuck is going down in this whole landscape — internet, technology — it’s trippy. A lot of people are going out of business. You have to invest a lot of money in a brick-and-mortar place just to stay there…I do think it would be super cool to have a stationary spot. I want to go to other places first and see what’s good. We already go direct to the consumer. Realistically, we don’t even need a place.”

It became clear to me that there never was a master plan — not one at the company’s inception, and certainly not one now. It was legitimately organic. I wasn’t sure, nor am I sure now, that the group intended on this organic nature from the start. Part of me believes that the trio, in their naive youthful days, just wanted to express themselves. They didn’t need a manifesto; they needed no guidelines or promises. And now, years later, they’re at the point at which they can attempt to make sense of it all — what it means, what they stand for, what the purpose of this all is. Perhaps the trio should never answer those questions completely, never put them neatly in a mental box to be stowed away. The never-ending cycle of contemplation isn’t driving this group manic — it’s strengthening them. While the rest of the world is busy defining themselves and subscribing to various ideologies, Always True is proving that never being certain is the most stable existence of all. At least then one is free to judge the next soul, thought, personality, or idea as authentic and worthy of reverence.

As Drew put it, “You’re just on a planet. Born in the middle of nowhere. You didn’t choose when your mom and dad did it. Who are we? We’re here. The stuff we make is lit. It’s pretty tight. But you could do the same exact thing. You’re just as special as us. We’re just as nothing as you.”


To check out Always True’s inventory and upcoming events, head over to www.alwaystrue.co. Their biggest collection, Chill Pill, is set to come out in the next few months. It’s the first time they’ve done a screen printed collection since May of 2018. Follow the company on Instagram — their handle is @alwaystrueco. Find out more about The SL8 Gallery here


Chase H



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