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An Inspired Chat with Amos Gregory Jr of Southwest Houston

Amos Gregory Jr shared their story and experiences with us recently and you can find our conversation below.

Amos, it’s always a pleasure to learn from you and your journey. Let’s start with a bit of a warmup: What is something outside of work that is bringing you joy lately?
Outside of work, the thing that’s been bringing me the most joy lately is getting my hands dirty with my 1981 Yamaha XS1100. There’s something almost meditative about working on a machine that predates the internet, predates modern conveniences, and yet still feels more alive than half the tech we surround ourselves with today. The XS1100 has this stubborn, muscular presence — a big, air‑cooled four that doesn’t apologize for anything. When you wrench on it, you’re not just swapping parts; you’re in conversation with decades of engineering choices, previous owners’ fingerprints, and the kind of analog honesty that’s hard to find now.

Riding is its own kind of therapy. The weight, the rumble, the way the engine settles into that low, confident growl — it forces you to be present. No screens, no notifications, no abstractions. Just the road, the wind, and a machine that rewards attention with absolute loyalty. Every time I take it out, it feels like stepping into a different timeline, one where things were built to last and built to be understood.

That mix of restoration, maintenance, and pure riding joy has become a grounding ritual for me. It’s a reminder that not everything needs to be optimized or automated. Some things are meant to be felt, tuned, and experienced with both hands. The XS1100 gives me that — a little rebellion, a little nostalgia, and a whole lot of joy.

Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Amos, and Sinkhole 42 is my little corner of the world where skate culture, DIY engineering, and art collide. I build and customize skateboards and longboards, but the real soul of the project lives in the deck art — each board becomes a canvas for the strange, glitch‑touched universe I’ve been shaping over the years. I love taking something as raw and functional as a deck and turning it into a piece of moving art, something that feels like it rolled out of a forgotten arcade or a dust‑choked neon back alley.

What makes Sinkhole 42 special is that every board is personal. I’m not mass‑producing anything; I’m crafting one‑off pieces that carry their own attitude, their own story, their own little bit of chaos. Lately I’ve been deep in new deck art, pushing the visuals further — more texture, more distortion, more of that feral energy that makes a board feel alive even before it hits pavement. It’s been a blast experimenting with new techniques, mixing analog grit with digital weirdness, and letting the boards evolve into something that feels both rideable and collectible.

At the end of the day, Sinkhole 42 is about motion — the motion of wheels on concrete, the motion of ideas mutating into art, the motion of a world that’s always glitching forward. If you’re into boards that ride hard and look like they slipped through a crack in reality, you’re in the right place.”

Great, so let’s dive into your journey a bit more. Who were you before the world told you who you had to be?
Before the world started handing out labels and expectations, I was a quiet, poetic stoner — the kind of kid who spent more time watching the sky than trying to impress anyone. I liked being on the edges of things, observing, drifting, letting ideas come and go like smoke. I wasn’t trying to be anything; I was just trying to feel the world in my own way.

That part of me never really went away. It’s still in the way I build, the way I draw, the way I move through the world. Sinkhole 42 is basically that same kid grown up — still curious, still wandering, still chasing the strange beauty in overlooked places. The only difference now is that I’ve learned how to turn that quiet, dreamy energy into something people can ride, hold, or hang on their wall.

Is there something you miss that no one else knows about?
Something I miss that almost no one knows about is bombing hills. Before the accident, that was my purest form of freedom — dropping in, letting gravity take over, trusting my body and my board completely. Getting hit by a car about a year ago changed all of that, and I’m still learning how to move with these new metal‑filled legs.

I still cruise on my longboard, just not as hard as I used to. The speed, the chaos, the full‑send rush — that’s the part I miss. But the love for riding never left; it just shifted into something slower, quieter, and more intentional.

So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. Is the public version of you the real you?
Yeah — the public version of me is the real me. I’m the same in public as I am when I’m alone. I don’t really have a performance mode or a curated persona. What you see is what you get: the quiet, poetic stoner energy, the maker, the rider, the person who moves through the world at their own pace. I’ve never been good at pretending to be anything else, and honestly, I don’t want to be.

Okay, we’ve made it essentially to the end. One last question before you go. What is the story you hope people tell about you when you’re gone?
The story I hope people tell about me when I’m gone is that I was a funny person. Not in a loud, look‑at‑me way, and not because I was trying to be. I’ve never been the type to chase attention or craft some big persona. But I like the idea that the people who crossed my path caught those moments where my lighter side slipped through — the dry comments, the unexpected jokes, the quiet humor that shows up when I’m relaxed and comfortable.

I think a lot of people see the art, the boards, the tech, the grit, the rebuilding, the metal in my legs, the whole robotic vibe — and they assume I’m serious all the time. And yeah, I can be focused, I can be intense about the things I care about, but underneath all of that, I’ve always had this soft, funny streak that only certain people get to see.

If there’s a story that survives me, I hope it’s that I made people laugh in those small, honest ways. That I brought a little levity into heavy moments. That even when life got weird or hard or chaotic, I still had that spark.

I don’t need to be remembered as some legend or some tortured artist. I’d be happy if people just said, ‘Yeah, Amos was funny. He had this way of dropping a line that cracked you up when you least expected it.’ That feels real to me. That feels enough.

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Amos A Gregory Jr

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