2016 Rust Belt Rising Star Bartender Will Hollingsworth of Spotted Owl

2016 Rust Belt Rising Star Bartender Will Hollingsworth of Spotted Owl
November 2016

Eugene, Oregon native Will Hollingsworth is a bit of an unlikely bartender. He’s an intellectual with degrees in philosophy and history of math and science with concentrations in classics and comparative literature. He’s self-professedly not a cocktail nerd. What draws him to the bar is the bar itself, the community of people holding the glasses. 

Before Hollingsworth found himself behind the stick, he worked in political communications, most notably with the 2008 Barack Obama campaign. Victory secured, Hollingsworth zigzagged across the country, finally settling in Cleveland, where he landed his first bartending gig. He mixed at Rising Star Restauranteur Jonathon Sawyer’s Greenhouse Tavern and later Michael Symon’s Lolita, loving the work but becoming increasingly obsessed with creating the ideal bar atmosphere. 

Hollingsworth set out on his own, opening The Spotted Owl in an old monastery complete with stain glass windows. He expected to people to flock to the bar for its vibe rather than his esoteric drink list. Cocktail sales quickly surpassed beer, though, and Hollingsworth hopped over to New York to for an intense stage at the Dead Rabbit, working with Rising Stars alum Jillian Vose. Back behind the stick of Spotted Owl, Hollingsworth leads a bar that’s at once seedy and sacred, but above all else hospitable, welcoming, and communal—it also happens to serve the best damn cocktails in Cleveland and for miles around. 

Interview with Rust Belt Rising Star Bartender Will Hollingsworth of The Spotted Owl

Caroline Hathett: How did you get your start?
Will Hollingsworth:
I came to Cleveland when I was 23 and wanted to try my hand at bartending, and had never bartended before. I sat at The Greenhouse Tavern and maxed out my credit cards sitting there during happy hours. Eventually I wore them down, and they hired me. I got in there, like “When can I get back there?” and was told I’d be running food. I got behind the bar within three months through sheer force of will. I left in September of 2010 to work at Lolita. In January 2011, I started writing business plans. I spent six months raising money, a year in design, and a year in construction. 

CH: Who’s your mentor?
Nobody really taught me how to make cocktails until six months after we opened. I felt like my compass was spinning. I needed to go to New York and see drink making done at the highest possible level. I thought, “Is what they’re doing in New York qualitatively better than what we’re doing here, or quantitatively better than what we’re doing here.” I put it out there on Facebook that I wanted to visit. It was February 2014. Dead Rabbit’s third menu had just come out, and my team had spent a month obsessing over it. I’m watching the Facebook comment thread populate and Jack McGarry wrote. Then I shit my pants. I was a wreck. Then I e-mailed him. I spent a week with Jillian Vose. In terms of cocktail mentors, she would be it. After the experience, I called a staff meeting. I knew what I wanted—no more compromise. New York cocktails are better than ours, but they not so much better that we can’t keep up. There’s an opportunity for us here to do something world class. 

CH: Tell me about your drink making philosophy.
The watch word around here is that simple is elegant and elegant is simple. A good thing is better by making it simpler rather than making it more complicated. I’m a reductionist thinker. All of the best drinks aren’t terribly overwrought in their conception or execution. 

CH: How do you name your cocktails?
I don’t name them until they’re made. I like to make a drink and sit with it and attempt to have a pure experience with it and find out what it reminds me of. Sometimes it reminds me of a poem. Sometimes it reminds me of a pair of sneakers. Generally speaking, I’ll name it based on that association.

CH: Tell me about opening the bar? What was your biggest challenge and how did you overcome it?
I raised a quarter of a million dollars. A liquor license is $30,000. I pulled it off because we built all of this from scratch. All of our electric, plumbing, HVAC—it’s all brand new. I negotiated that my landlord put in a lot. He put in $150,000. All in all, I would estimate that it cost $400,000 to open. But this bar had to get built. Someone had to build a bar like this.