How Dogfish Head’s Sam Calagione Built An Off-Centered Beer Empire On Analog Moments

“Grandma’s snack mix was excellent.”

Sam Calagione told me this dead serious. We were in the middle of a photo op at Analog-A-Birthday, the massive festival celebrating Dogfish Head’s 30th anniversary, surrounded by the industrial hum of his brewing empire in Milton, Delaware. He wasn’t talking about quarterly earnings, all those “no one is drinking beer anymore” trend pieces you see from city-slicker magazines on Instagram, or the synergy or the $300 million merger with Boston Beer. He was making sure I passed a message to Connor Toole, BroBible’s long-time deputy editor, who had slipped Sam a bag of his grandmother’s homemade Chex Mix at a beer festival in New England a few weeks prior.

Most CEOs would have tossed it in the trash or handed it to an assistant. Sam ate it. He remembered it. In fact, he brought it up unprompted the night before, while we were holding court at Chesapeake & Maine, his seafood spot in Rehoboth Beach. Somewhere between slurping oysters, decimating a bowl of Maryland crab dip, and trading war stories about our favorite Dead & Company shows from the Sphere run, he paused to make sure I knew. He wanted Connor’s grandma to know it didn’t just survive the journey—it slapped.

That specific attention to detail—that genuine, unmanufactured appreciation for the little, human things—is freakin’ everything. It is the secret sauce, or perhaps the secret yeast strain, that explains how a guy brewing weird beer in a New York City apartment in the early ‘90s turned into the godfather of East Coast craft brewing.

I witnessed scenes like this all day Saturday at the festival. People were stopping him constantly—handshakes, hugs, high-fives… so many high-fives—treating him less like a distant CEO and more like the mayor of a village they’re very proud to call home. It was his and his hard-working employees’ birthday party, sure, but it felt like an off-center coronation for a business he started 30 years ago that has grown into a formidable institution, anchoring coastal Delaware and rippling out across the entire country.

I flew across the country for this. Literally. I crossed the digital divide of three time zones, trading the Pacific for the Atlantic, to celebrate that 30th anniversary, enjoying a weekend-long revival of the tactile, the real, and the off-centered.

For me, it wasn’t just a press trip. It was a pilgrimage home.

Dela…where?

Let’s talk about Delaware. For most of the country, the “First State” is a punchline from Wayne’s World (“Hi… I’m in Delaware”). It’s a screen door banging in the wind. I make this joke a lot when I write about the First State, and it always comes from a place of off-centered love. I’d like to think my Delaware cred runs deep. I come from a family of teachers who scraped together pennies all school year just so we could spend two glorious weeks every summer at the beach. My great-aunt had a trailer in Dewey Beach back in the ‘60s, when it was just a three-bar town.

We spent our days surf fishing off the coast and riding bikes to Cape Henlopen and the Indian River Inlet. Friday nights were for people-watching at the Lighthouse by the Rusty Rudder, or peering through the chicken-wire windows of the Bottle & Cork to catch a glimpse of the bands sweating it out on stage. Later, when I moved to New York City, I became a sort of unofficial correspondent for the town, writing prolifically on this very website about the sacred virtues of Orange Crushes and Starboard Bloody Marys. I have a drawer full of Dewey Beach souvenirs my mom has shipped me on her trips to the beach, of which I’ll never part ways with.

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Brandon Wenerd is the publisher of BroBible.com. Read and subscribe to his weekly Substack newsletter, The Wenerd Weekly, where he shares thoughts on men’s fashion, footwear, Grateful Dead, and the intersection of music, media, and culture.

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As a West Coaster now, I’ve always called Dewey “the most California beach town on the East Coast.” It’s a special place where the humidity wraps around you like a heavy blanket and the salt air, at least for me, smells like nostalgia. In a way, I feel like I saw Dogfish Head’s upward trajectory alongside my own coming of age. I watched it grow from a scrappy brewpub—sporting a badass shark logo that looked a hell of a lot like the sand sharks we’d catch surf fishing—into a cultural leviathan that seemed to be everywhere in the Mid-Atlantic and Northeast, all while I was still trying to figure out what I wanted to be when I grew up.

Three Acts of a Brewing Rock Star

Sam Calagione is easily one of the entrepreneurs I admire most. Not because of the money, but because he treats business like cutting punk rock albums. He’s been shaking up the status quo in the beer business for three decades now. It’s serious work, and he seems to go about it effortlessly. Standing in the shadows of Milton’s hundred-thousand-case tanks, I asked him to break down this “long, strange trip” into chapters.

“It’s been wonderful,” he said, that charismatic grin spreading across his face. “Time flies when you’re having fun. We’re a brewery obsessed with time—from 30 Minute to 60 Minute, 120 Minute—the time’s flown by.”

He breaks the Dogfish saga into three movements:

Chapter One: The Horror Film.

“I would say the first chapter was kind of a horror film in that we didn’t know we were going to make it,” Sam admits. “We opened here in rural, coastal Delaware. We were the only brewery in the state.” Back then, brewing with culinary ingredients wasn’t “innovation.” It was heresy. “The first generation of craft beer lovers were like, ‘What are you putting coffee in your beer for? Why are you putting raisins in your beer?’” Sam recalled, mimicking the outrage of purists. “They were more mad at us for fucking with tradition than they were excited about our creative journey.”

Chapter Two: The Pioneer Era.

Then came the turn. The critics who hated the raisins started calling him a visionary. The Today Show called. People Magazine. The Discovery Channel gave him a show. “That was the chapter of just tremendous growth,” he says.

Chapter Three: The Soulful Scale.

This is the part that usually kills the vibe. The “sellout” phase. But Sam flipped the script. “The journey still feels real, and it doesn’t feel like we grew too fast,” Sam said, gesturing to the massive infrastructure around us. “Because all those giant tanks are filled with beers that have granola in them and black limes in them and pumpkin meat in them. So we didn’t have to homogenize or dumb down our beers and spirits to grow. If anything, the industry grew with us.”

The status quo sucks, after all.

Analog Moments and a Setlist of Deep Cuts

The weekend’s tone was perfectly set during a fireside chat at the Dogfish Inn in Lewes. It was a crisp November night, the kind that demands a hoodie and a koozie for your beer can. Sam and his team talked about the symbiotic relationship between great music and great beer.

Hearing them speak about the Grateful Dead’s spirit, which I talked to Sam about earlier this year, made me feel compelled to testify like I was at a revival. I shared a story about going to the Dead 60 show at Golden Gate Park, running into friends on that huge field that I hadn’t seen in years—from high school, from my time in Los Angeles. That sense of instant, unexpected community, amplified by the bonfire and the beer, was the ideal way to kick off a celebration of off-centeredness.

And the beer? It was a setlist of deep cuts. The Dogfish Head team truly celebrated the analog spirit by experimenting across their entire portfolio. I was a huge fan of the rich, full-bodied Alternate Takes #1 (45% ABV), the OG whiskey in their series, inspired by the analog age of music and alternate sounds. It’s a mind-blowingly delicious whiskey.

Kolsch is my favorite beer style these days, and there was the unexpectedly crisp Gin Rations Kolsch, aged on lemon peels, juniper, and spices (5.0% ABV). The 90 Minute IPA base was taken up a notch with the Succulent Chinese Meal (9% ABV), served from a firkin with candied bitter orange, red chili, and Szechuan peppercorns for a unique peppery kick.

I also really loved the Snowy Spruce (9% ABV). It’s a riff on their Pennsylvania Tuxedo pale ale—a beer paying homage to the red-and-black Woolrich hunting suits ubiquitous in the woods where I grew up. This version, brewed with smoked star anise, pemba clove, and cloud forest yellow cardamom, was wonderfully piny. It tasted like a walk through a Christmas tree farm in December—a beer meant for those crisp days when you’re zipped into a Carhartt jacket and lacing up L.L. Bean duck boots.

Their special SpaghettDE (6.66% ABV)—an American light lager cocktail brewed with gourmet corn grits and Dogfish’s Scull & Crossbones Italian-style aperitif—was a delicious surprise, as the head brewer promised. Before we toured the iconic Dogfish Head Steampunk Treehouse, he called it “a special beer”, brewed after a classic dive bar concoction, and boy was he right. Finally, the Pan-Am-Jam-Band (5.6% ABV), brewed in collaboration with Relix, a music magazine I’ve been reading since a teenager, blended cabernet sauvignon juice, wild berries, prickly pear, and peaches into a perfect summer wheat ale.

But the beating heart of the Dogfish ethos is music.

“Nothing’s been more influential to the Dogfish Head brand journey than music,” Sam asserted. “I mean that even more than the culinary world.”

Sam, a self-described music head, grew up in Western Massachusetts, dialing into tiny radio stations from nearby colleges in the 1980s. This exposure to underground sounds—hip hop shows from the Bronx, punk scenes at CBGBs—ignited an appreciation for the DIY approach. It was cool to see that spirit alive at the festival, with bands like Bushwick’s Dead—a modern interpretation of the Dead—keeping the vibe spinning.

“You think of Afrika Bambaataa pulling electric cords into a basketball field to do the first DJ sets, or you think of Sonic Youth getting in the van, making their own post-gig posters,” he mused. “That really inspired us at Dogfish to use the DIY approach of hip hop and punk rock to grow our brand in a really kind of punk rock, rootsy way.”

I decided to pull the ultimate music snob move and hit him with the “Oh, you’re a fan? Name five bands” challenge. It’s the kind of internet-poisoned question designed to trip up casuals, but Sam didn’t flinch. I knew he wouldn’t. He didn’t give me a corporate-approved playlist of harmless classic rock; he gave me a manifesto of taste: The Felice Brothers (“underrated”), The Replacements (“an all-time favorite”), Stereolab, Aphex Twin, and the undeniable Guided by Voices, who just released their 48th album.

It tracks. A buddy from Philly who used to work at the famed Monk’s Cafe, a beer mecca in Philadelphia, DM’d me on IG to confirm Sam’s legend status. “He rules,” he wrote. He recalled playing a gig at the brewery with musician Steve Gunn about a decade ago where Sam stepped in to DJ. “If I recall correctly he only brought like 3 records and they were all jazz.” That is a level of specific, confident curation that you just can’t fake.

A Full Circle Realization

The success of Dogfish Head means that Sam’s punk-rock approach now fuels an entire Delaware experience. The Milton brewery is a full-blown Charlie and the Chocolate Factory for beer nerds. Down the road, the Dogfish Inn serves as a basecamp for the lifestyle.

And the food? My god, the food. I told my mom the night after I ate at Chesapeake & Maine that their crab cakes were some of the best I’ve ever had. And I’m from the part of Pennsylvania where we take our proximity to Maryland crab seriously. It’s a James Beard Award semi-finalist spot for a reason.

“Inspired by my summers in Maine and our roots in the Chesapeake,” Sam explains, “we’ve crafted a menu that’s bold, fresh, and uniquely Dogfish.”

Back in my last semester of college at Penn State in 2008, I was debating whether to be the English teacher I was studying to be or go chase the dream of being a writer. That same fall, The New Yorker published a brilliant profile on Sam Calagione called “A Better Brew.”

Seeing that piece, tracing his origin story from an English major to a brewing outlaw, was a foundational spark for my own journey. It made me decide to abandon the syllabus and commit to writing something like that myself someday. That made me run off to Aspen for a year, then to New York City to help get BroBible off the ground and see where the ride would take me.

I don’t know how close I’ve come to achieving that dream in life—I’m usually just trying to keep the lights on in the content mine—but getting to write about the founder of Dogfish Head thirty years into his journey feels like I’m finally running my own version of that playbook.

To be back in Delaware, celebrating his vision, listening to music I love, eating crab cakes that taste like summer memories, and writing this profile—that is the very definition of an analog moment.

Flying back East to that home away from home this weekend to celebrate their 30th anniversary with Sam and his team was such a hoot. Perhaps even my favorite side quest of the year so far. It’s the moment when the long, strange trip makes perfect sense, when the creative, off-centered spark that launched a $300 million empire validates the pursuit of every single, genuine, punk-rock, DIY dream.

Cheers to 30 years to Sam and the Dogfish team. And cheers to grandmas everywhere making excellent snack mix.