Chewhiker – 44 in Chicago

Chewhiker – 44 in Chicago

During February and March 2016 I traveled North America to meet the Chew community, DJs, partners and investors.

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My light sleep broke with the sound of a factory-default Android ringtone. A man answered, projecting three words into the phone in a thick southern drawl. The only word I understood was the name of the town, Kentucky. Immediately after the words came, so did a bout of deep chested whooping coughs. After fifteen minutes of the same it was clear I wasn’t going to get any more sleep. I cracked open the curtain to find the first light hitting fresh snow on the fields of Indiana. I got up and moved to the observation car.

The observation car was completely empty. I unlocked my phone and scrolled through my collection of podcasts. The time on the screen showed 5:32am. Small towns, farms and schools rolled by. The day got brighter and the snow got heavier.


I arrived into Union Station just after 9:30am. Upon walking out of the station into the snow my hands froze in seconds. I searched for somewhere to sit and work out what to do next. Chicago’s downtown district was tall and imposing. Low cloud masked the tops of the blue-grey tower blocks. The station backed a wide waterway with bridges of red steel crossing at regular intervals. Each car passing over the bridge made a sound similar to trucks passing over a cattle grid back home. Crossing the bridge closest to the station, I headed downtown.


After fifteen minutes I’d failed to find a coffee shop that would take me in for the morning. Hiding in the entrance of a Wells Fargo out of the wind I found a list of top spaces to work in the city. Number two on the list was Brooklyn Boulders. With numb fingers I dug into my backpack for some gloves, and began trudging through the thin layer of fresh snow back across the river, away from the skyscrapers of downtown, towards the west loop.

Brooklyn Boulders greeted me with a blast of warm air as I pushed through the double doors. Back In London I spent many mornings climbing before heading into the office. This place combined work space and climbing walls into one. Genius. My fingers turned from pink to yellow. Once I could type I set about planning the next couple of days.


News of my trip had now spread beyond just the first email and the Chew network. While I was staying in The Bay Area with Wax n’ Cats I’d heard a great deal about the Chicago scene. At the time, I only had one offer to stay in the city. Thanks to Justin and a few quick emails, two of his friends offered me their home.

As I walked north from the work space, warehouses gave way to skinny townhouses of wood, brick, and brownstone. The houses felt like a supersized version of Amsterdam’s city streets. I rounded a block and approached a dark brick house. Knocking on the door Molly and Aaron greeted me with a smile.

The couple were deeply linked with with the music scene in the Chicago, and their entire basement space was given over to decks and a sound system. What I’d chanced upon was a whole community of DJs and fans of the music. I’d only been in the city for a few hours but felt right at home.

The evening started with some Mescal. I’d had this drink for the first time a year ago while traveling abroad. A clear spirit made from the agave plant, it has the punch of tequila and the smoke of whiskey. The small bar we went to had opened a few days before, so we had the pleasure of being the first to taste each imported bottle. Each drink came in a terracotta dish with a slice of blood orange and salt mixed with crickets and cacao. On an empty stomach the spirit hit me fast. It was time for some food.

When thinking of “real American food” before this trip I wouldn’t have thought of sausage and pretzels. Germany and America were not two countries I’d ever linked before in a culinary sense. But since a particularly drunken night in New York I’d eaten pretzels and sausage in every city.

Fed and watered to excess, we moved on to a local club. From outside I could pick up the tempo of house music playing to the packed bar. At home, house music can often mean the same overplayed tracks again and again (Just take a look at my DJ sets!). Here, every track was fresh and heavy. The selection from the local DJs flowed from stacks and boxes of vinyl spread around the booth, and new productions played fresh from burned CDs. Leaning over the booth to catch a glimpse of the artist I began talking to the DJ. He told me he’d been DJ’ing for seven years in Chicago and was just starting to build up respect in the house community.

On the way home I could feel my head nodding against the taxi window. The weeks of train chairs and hard sofas had toughened my shoulder and my back ached. In the house I was lead passed the sofa (thankfully) and up the spiral stairs to a full en-suite room right off of AirBnB. For the first time in the trip I spread myself from corner to corner on the soft mattress and fell asleep, dead to the world.

When Curly Alan first started streaming on Chew, the whole office stopped to watch. We’d all seen some wild visuals before but his were unique. Musically, his routine consists of lively scratch DJ sets mixing hip hop and funk. On video all you notice is his huge white afro wig – this alone would grab your attention. Taking it to the next level, the wig is full of LEDs that move and change with the bassline of the music.

Alan and I had been speaking online since he joined the site, and I was looking forward to meeting up with him. Traveling out to his apartment along the shore it was clear that Chicago definitely is the third largest city in the country. The car traveled along the waterfront for over thirty minutes, passing a steady stream of uninterrupted flats facing out over the lake.

I jumped out of the car and walked the last half-block to the apartment building. As I approached, a resident held the door for me and I continued in and up the stairs. The corridors smelled a bit like smoke as I counted the brass numbers on each door to reach Alan’s flat. Three locks slid back before the door opened to reveal the man himself. This time without the afro.

The flat was the smallest I’d come across in the country so far but about standard for a London flat. Inside was wall-to-wall with two full sounds systems, monitors and decks. Across one wall a large flatscreen TV that looked like it had come from an airport departure lounge. Cameras pointed in from either side of the DJ setup. The Chew logo, projected on the back wall, was chopping and changing in shape and colour.


I found out that Alan works for a video editing and production company in the city. His friends greeted me as I came in. A perk of working for a production company is access to professional level equipment, and in that small space Alan had club-grade visual software running the projector.

After ordering a pizza and grabbing beer we started the show. Each DJ brought a new style and skills to the decks. As the small room heated up so did the mixing abilities. With a lot of switching around we got the CDJs plugged in and I joined the mix. Finally as the end of the night approached Alan stepped up. He put on the net of cables and LEDs and scratched and cut from track to track while his headwear filled the room with bursts of bright light with each kick drum. After six full hours of mixing the guests began to drift off. Before calling it a night I had a go at some beat juggling (without the afro) before crashing on a brand new air bed right under the decks.


The next day I woke to the sound of a British commentator’s voice coming from the television. Alan was a big fan of football so I tried my best to remember what little I know about the sport. We watched the rest of the game before heading to breakfast.

I felt like this leg of my trip was much too short. With every host I wanted to stay longer. In every club I wanted to grab the DJs collection of vinyl and take it home with me. I saw such a fleeting glimpse of the music, art and food in Chicago and it really connected with me. Before leaving I promised myself that I’d come back for longer, and next time I’d bring an empty suitcase ready to fill with records. I said my goodbyes to Alan and headed back to Union Station for another eighteen hour train ride to Denver. This time I made sure to buy some ear plugs.



Hi, my name is Ben and I’m a startup founder and adventurer. Highlights of my career include building three startups from zero to exit (, StreamOn and working on Aux) and cycling – halfway – around the world in 2018. Subscribe for updates, blog posts and videos on my startup life and adventure travels.
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