Brand Breakdown: The Highroller Lobster Co. | Portland, ME

Welcome to Brand Breakdown. A little series where I take a closer look at brands that are doing things the right way (as far as Kyle Johnston is concerned). This isn’t about who has the fanciest logo or the deepest pockets. It’s about the details that actually matter: how a brand makes you feel, what makes it memorable, and why it works beyond the surface-level stuff. Basically, I’m here to nerd out a bit on brand strategy in the wild, told through real experiences instead of boring marketing jargon. And what better place to kick things off than a lobster joint in Portland that does branding better than some Fortune 500 companies?

My first impression of The Highroller Lobster Co. wasn’t even food-related. I walked in the wrong door. Instead of the restaurant, I ended up in their gift shop. But while I was swiveling my head around the room, looking for where to go, the dude behind the counter greeted me right away, pointed me in the right direction, and made the whole situation feel intentional. Instant hospitality points.

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But here’s where it got interesting. Even before I sat down to eat, I was already kind of hooked by what I was seeing. The space is in an old brick building in downtown Portland, but inside it’s a full-on red-and-white brand explosion. Walls tiled, logos everywhere, and a gift shop packed with swag. And not that cheap throwaway swag that ends up in a donation bin in six months, but high-quality hoodies, jackets, hats and shirts all with designs that could live in a Brooklyn streetwear boutique. Some pieces were clearly “inspired” by other brands (some call it paying homage, some call it copying, and another dude in history would’ve called it the ol’ “good artists copy; great artists steal.” Whatever label you slap on it, the stuff looked super good). 

Everywhere you looked, the brand was alive. Pens, cups, glasses, placemats. Even the old-school plastic Coca-Cola cups had been reimagined with a Highroller stamp. On the way to the bar we passed an oyster station where the guy shucking was casually rocking a red velvet cowboy hat, which felt perfectly on-brand in its own quirky way. And yes, even the bathrooms carried the vibe. The walls were bombed with stickers and mural art, like the brand refused to take a break just because you did.

My wife went classic with a lobster roll. I grabbed fish and chips with a couple of local IPAs. (Yeah, I know this is starting to sound like a Yelp review from a middle-aged soccer mom, but just bear with me here.) The food was phenomenal, the beer was ice cold, and the staff? Honestly the best part. Not just our bartender, but literally every person we interacted with.

What stuck with me most was how authentically themselves the staff were. No fake “corporate voice,” no robotic persona, just real people. Most folks were covered in tattoos. Metal music blasting. Conversations that sounded like conversations, not scripts. They were just being who they are, and that energy spread across the whole restaurant. You know that feeling when you can tell someone’s putting on an “at work” mask? People can see right through that BS and thankfully, there was none of that here. This was pure authenticity, and it made the experience that much better.

Here’s why it works: Highroller nails what so many brands miss.

• Authenticity: Their employees aren’t pretending. They’re not polishing themselves into some soulless corporate mold. They’re real, relatable, and genuinely enjoying what they do. Customers notice that and remember it.
• Design & Branding: The logo, the swag, the interiors, the cups, the pens, the bathrooms. All on-brand, all the time. Nothing feels half-assed. And because it’s executed so well, the brand feels bigger than “just a restaurant.” It feels like a lifestyle.
• Consistency: From the gift shop to the oyster station cowboy hat to the sticker-covered bathroom walls, there’s a thread connecting every touchpoint. That consistency makes the brand stick.
• The Food Itself: At the end of the day, people are spending their money on the food and drinks. That's the core product. Highroller pairs that with branding that amplifies the experience instead of cheapening it. The lobster roll, the fish and chips, the cold IPAs, all of it felt just as considered as the design and atmosphere. When your core product (in this case, some good-ass food) is backed up by a brand that feels authentic and intentional, it turns a casual lunch into something memorable. It creates the kind of experience that you want to share with the world. And that, my friend, is why investing in your brand is worth it.

The Highroller Lobster Co. proves that branding isn’t a logo or a tagline. It’s an atmosphere, an attitude, and a thousand little choices that add up to an unforgettable experience. That’s the kind of branding worth breaking down.