The Dig Inn Story
From Chicago Tech to Small Town Magic
Some people move to small towns to slow down. Ben and Holly? They cranked up the volume.
Trading their Chicago tech life for a farm in the heart of small-town Iowa might sound like the start of a Hallmark movie, but this isn't your typical 'city folks go country' story. These two could've picked anywhere in the world, but they chose a fifth-generation farm in central Iowa, nestled somewhere between Cedar Falls and Des Moines. And not to just casually exist there - they dug ALL THE WAY in. Because when you mix pure hustle with genuine heart, an eye for the extraordinary and souls full of creative energy, you get something entirely different. You get The Dig Inn.
THE JOURNEY BEGINS
The journey kicked off in Chicago, where Ben and a couple friends turned their vinyl obsession into something genius - the Flipbin. What started as a Kickstarter dream became this killer display system that screams Ben's style - bold colors, mid-century modern vibes, transforming your ‘Now Playing’ album into a piece of art. (The guy has an eye for finding magic in the everyday - just check out his Instagram @bfrobertson for proof). Still proudly Chicago-made but shipped from his Iowa barn, it's a perfect reflection of Ben's split-heart between city and small-town life.
Meanwhile, Ben and Holly were running Mac MD - their successful Chicago tech company serving up Apple solutions for businesses and high-end clients - but dreaming of something different. When the opportunity to take over Ben's family farm (generation five, if you're counting) came up, they sold the company and traded city life for small-town possibilities.
Their farmhouse quickly became a testament to their collector's soul - like a museum of cool crashed into a 70's time capsule, filled with vinyl records and quirky vintage finds that hint at the kind of curators these two really are.
There's this thing about Ben - he's got this energy that's hard to explain until you meet him. He's chill enough to appreciate slow farm life, but his mind's always spinning with ideas faster than the records he collects. When the old Broad Street Brewery space opened up in downtown Reinbeck, it was like the universe handed him a blank canvas. Why not add 'bar owner' to the resume?
WELCOME TO THE DIG INN
The Dig Inn quickly became pure Ben and Holly energy made physical. It's like their personal collection exploded into a public space in the best possible way - where Ben's carefully curated vinyl collection meets genuine small-town hospitality, where his childlike enthusiasm (catch him doing cannonballs at the local pool in summer) meets his deep baseball knowledge (just ask him about the A's - if you've got time). He's the kind of guy who geeks out over album pressings and can tell you stories about every record in his collection, turning each vinyl flip into a mini music history lesson.
The space feels like magic - vintage couches that look stolen from your grandma's house, a kitchen table that will spark memories of childhood, and walls lined with records that are part art and part music history. The taps are flowing with craft discoveries (including an impressive selection of sours you wouldn't expect to find in small-town Iowa), and there's probably a cult classic film playing on the tv over the bar.
COMMUNITY HUB
But here's the thing about The Dig Inn - it's evolved into something bigger: a true community hub where cyclers end their rides, Record Store Day feels like a holiday, and live music fills the intimate space several times throughout the year. Holly's annual Halloween parties (costumes absolutely required) have become tradition, just one more way this small-town spot keeps surprising everyone with its big personality.
FARM LIFE & FLOWER POWER
Meanwhile, Holly - a timeless beauty with a radiant soul who can effortlessly transition from arranging home-grown bouquets to chasing goats in muddy farm boots - turned those initial dreams of growing vegetables into Five R Farm. Here, specialty blooms and Dahlias thrive alongside honeybees, while she crafts everything from summer CSA baskets to winter wreaths and homemade beeswax wraps – she’s constantly creating. Between Frank and Otto living their best dog lives alongside the farm's growing menagerie of cats and goats (proof that Holly's heart is as big as her green thumb) and her natural talent for making everyone feel like a friend, Holly brings that same warmth to The Dig Inn that makes it more than just a bar. You know those people who just make everything better by being there? That's Holly's energy.
SHARING REINBECK'S FUTURE
But Ben and Holly aren't just business owners in Reinbeck - they're community builders. Whether it's Ben serving on the community development board and hosting Lions Club meetings at The Dig Inn, or Holly turning a simple farmers market idea into a thriving local movement, they're helping shape the town's future. And when they do take a rare break? You'll find them road-tripping to discover hidden dive bars or seeking out live music in unexpected places - always bringing those discoveries and that energy back home to Reinbeck.
The Dig Inn isn't just another small-town bar. It's what happens when you let joy run a business, when pure hustle meets genuine heart, and when you're not afraid to build something as unique as you are. It's where locals gather and mingle with vinyl enthusiasts, where farmers market goers grab a bloody-mary, and where everyone's welcome to just... be.
Some people move to small towns to slow down. Ben and Holly? They're showing us all how to speed up in exactly the right way.
