The Art of Managing: Shannon Kohlmeier, Shawn Creamer, and Chef Tyler Cunningham of The Whippoorwill

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The Whippoorwill, is the winner of the Best Burger Reader’s Choice for 2013 and 2014 by NOW magazine, here in Toronto. It is a restaurant diner doing fresh, seasonal, and kitsch for families, friends, date nights, and everything in between, with bonus live music (literally and figuratively speaking). The trio of business partners behind The Whippoorwill, are married couple Shannon and Shawn, as well as Chef Tyler Cunningham. The couple are the perfect balance of opposites to run two very famous spots in the city, and as for The Whippoorwill, they leave plenty of creative space for Chef Cunningham to create his elevated diner staples with seasonal and fresh products.

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Coming in from that day’s extreme freeze, we immediately stepped into a very cozy and warm atmosphere. It was in between service, and we took in the warm tones of the room, walking over to Chef Tyler Cunningham near the back of the restaurant as he and his team prepped for a catering event that night. Soon after, Shannon, The Whippoorwill’s co-owner walks in and we proceed to sit down in one of their cozy four-person red booth seats.

For first-time guests, what would you recommend, and how would you describe The Whippoorwill experience?

I would definitely recommend one of our cocktails, it’s something very important to us, setting the tone for your meal with different flavours. We always use what’s in season, and have a section on our cocktail menu called ‘Going to the Market.’ Our bar manager will bring in what’s in season, and Chef Cunningham will bring in things from the food terminal. If people are adventurous we recommend leaving it in the bartender’s hands, and in terms of food, literally there is nothing that you could order that isn’t delicious.

We’ve won Toronto’s best burger in NOW Magazine 2 years running, and it’s definitely a neighbourhood favourite. I consider it something that brings people in the door, which then opens the door for them to see all the different things we have, how unique we are, and how creative Chef Cunningham is. We want to get people to step outside their comfort zone, and what many would consider typical Bloor & Lansdowne fare.

Come with an open mind and come hungry

After this Shawn, Shannon’s husband and fellow co-owner walks in and joins in.

What makes the burger so special?

Shannon: Chef Cunningham has this way of describing it. When you take a bite you have to expect that it’ll be messy and just close your eyes, and take a minute to just really taste it. He cares about his food, he cares about how it looks, tastes, and having consistency. It is going to be the same every time you have it, and you’re gonna crave it.

Shawn: Everybody gets the same burger, the recipe for the burger so simple, and Chef Cunningham doesn’t put and fillers.

Shannon: it’s burger meat…it’s juicy, and he serves it rare to medium rare. It’s delicious, you can’t go wrong.

How did you get into the food and hospitality industry?

My dad owned a pizzeria from when I was around eight years old. I used to stand on a milk crate and punch in orders. Neighbourhood people would come pick stuff up. I saw my dad go through so much stress. I thought to myself ‘I will never do this as a job’…and here we are. I saw how hard he worked, but I loved it. I loved the people. I worked at Eastside Mario’s when I was old enough, then stayed with Prime for quite a while. I worked at the Bier Markt, when I first moved to Toronto over a decade ago, and then Cadillac Lounge. I’ve worked at every different variation, and then I left it all. I got a new career in publishing, thinking those days were behind me, and then my husband lured me back in when he opened a bar.

Shawn: I worked in kitchens as a line cook and prep cook when I was younger, and then I didn’t for 15 years because I was a touring musician. Then, I opened the Dakota Tavern, and that was my first experience in the hospitality industry.

Shannon: From there I helped. Shawn wanted to go into the bar industry, specifically to have a place to play for musicians.

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Shawn: I wanted a place where I could play, all my friends could play, that treated musicians well, that had a certain aesthetic, a certain vibe. I met Tyler (Chef Cunningham) at the Dakota. We had mutual friends and we talked about opening up a restaurant for a long time. This place came up and we saw it as a good opportunity.

Shannon: There were a bunch of different reasons that pulled us here. It seemed inevitable that we just had to stay in this industry, it just kind of kept coming up.

Shawn: When we opened The Whippoorwill, part of it was like growing up. We had the bar for 7 years, and when Tyler and I talked about opening another place together, we knew that we wouldn’t open with anyone that wasn’t a family person. Tyler’s married with a child, and we’re married with 2 kids. We wanted to open a place where kids were welcome, and where parents could have a date night.

Did you have any mentors?

Shannon: Shawn, truthfully has been a big mentor of mine. Honestly, most women would be hesitant to say that their husband is a mentor of theirs, but he really did work so hard for so many years before I came on board. We’ve worked together for the last 2 years and I can see there is a method to his madness, and even at times when it’s against my nature to follow his lead, he definitely knows what he’s doing.

He’s offered me a great career, or what’s turning into a great career, and not everyone, can say that of their husband.

Shawn: As far as the restaurant is concerned, I learned most of what I know about restaurants from Tyler, our business partner and Chef. A lot of what I learned was through trial and error at the beginning, which was probably frustrating for him, but he’s worked in some of the best restaurants in the city, so he really knows what he’s doing.

What was that transition like from working separately, to working together?

Shannon: It was rough in the first year, because we had to adjust to each other. I’m a morning person, and he’s a night person. I like lists, whereas he knows what needs to get done, but he doesn’t have to do it in a certain timeframe, there was a bit of a conflict there.

Shawn: We’ve needed Shannon’s organization skills with all the businesses that we’ve had.

Shannon: We balance each other out, we’ve learned to. From him, I’ve learned to just delegate and let it go. It might not be the way you do it, but it might actually be better if you can look at it with the right vision.

How would you define great service?

Shawn: I think great service comes with the knowledge of the food first and foremost, and a really good table presence. Knowing the steps of service is very important, good training, and a good personality.

Shannon: Knowing how to read a table, there are times where it calls for you to read the situation and that’s just as important as having a presence. My number one thing, when I’m serving is saying, “heads up hockey people, look around.” It’s having an awareness of the whole room, which can be a difficult.

Shawn: We’re really lucky here. Our staff are really friendly, and they care about the place. It’s a really unpretentious room, we want people to know that you can talk loud in here, you can laugh, and you can have a cocktail. It’s a great place to sit with 8 of your friends or even just one.

Why did you choose this area, specifically the Bloordale community and its growing culinary scene?

Much like what we did with the Dakota, it was a bit of real estate speculation. From the people that we knew, like a lot of musicians and actors that were moving here. Similar to what was happening in Ossington, all of a sudden, the condos were popping up, and you knew you were going to get young professionals, that are foodies and liked to go out for cocktails.

My best friend owns the Three Speed, and his partners own the Communist Daughter. Interestingly, they are the best at speculating which neighbourhood is going to happen next, and we just say ‘oh well they’re right, so here we come’. There are new neighbourhoods popping up on this strip, it’s changing fairly quickly and I don’t think you’ll even recognize it in probably 3 to 4 years.

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Quickly, within in 10 Days. It didn’t look anything like this. We had to do it quickly because there was a built-in brunch crowd we didn’t want to lose. It was super busy on Saturday’s and Sunday’s. We were closed only for one weekend and we were literally here 24/hours a day. The backbar we found in the Junction at a place called Smash. When we saw that, it changed how the front was going to look, and it was the defining piece.

Shannon: What’s always a struggle for restaurateurs is that our vision is bigger than our budget. We would love to do things, but usually it’s going to be ‘what you have at that moment and what you can do with it.’

How has the crowd responded?

Shawn: People mourned their $7 breakfast, but it only took a short period of time before people realized, ‘Wow, this food is so good,’ and that the cocktails were really good too. I think people are more excited about there being a restaurant and cocktail bar in their neighbourhood now. Most regulars from the previous diner stayed, and now get their new favourite, but because Tyler keeps everything seasonal and fresh, the menu changes constantly. Everybody just waits for their favourite food item to come back. We even get emails asking, ‘is this on the menu yet?’

Shannon: Social media is such an important piece of the restaurant and bar industry, and we get so much great feedback from there.

It warms my heart when people take the time to actually say something nice about you, which happens 99% of the time with us

For someone to take the time to search you out, find your Twitter handle, and say something nice…I try to always acknowledge that or thank them because their feedback is invaluable.

Shawn: It’s always nice to work in a place where people are always happy too. They are always happy with the food, and service.

How would you describe the typical brunch, dinner, and late night crowd?

Toronto has an unnatural love affair with brunch…

Shannon: and that is not a secret. People here order their favourite. They know what they’re here for.

Shawn: The dinner crowd changes. At 6 o’clock we have families, that are the early dinner crowd. At night we have a lot of big groups of friends. Saturday night is 80% ladies and their friend’s eating dinner. The late night crowd depends on the night. If there are bands playing, we get a little boisterous, and if there isn’t, it’s mostly just people coming in, sitting with their friend’s, and having cocktails.

After this, Shawn shifts out of the booth and tags in Chef Tyler Cunningham.

Why is farm-to-table, seasonal, and fresh important to you?

Tyler: It’s for environmental reasons, and how it is reducing our carbon footprint, but mainly it is that each part of our season here in Canada and Ontario, have special foods that are of that time of the year. I believe it is very important for people to anticipate, appreciate, and remember those moments and products. It makes food more important when you anticipate and want something when you can’t have it.

Brunch is already really big in the city. What sets yours apart?

Tyler: I’m not too sure if it’s setting us apart, or if it’s just giving people what they want. I modelled the menu to emulate a diner style. I didn’t want to shock people with the transition from Bloordale Pantry to The Whippoorwill. What we do is more or less inspired diner classics. The seasonal toppings change, everything’s very current, but I think that people can always rely on the fact that everything’s going to be well prepared. It’s always going to be consistent. When I opened, my goal was to have a community neighbourhood restaurant.

This isn’t about me, or about us. It’s about the community and when you come here, you don’t have to worry about the food or the service. When you leave, you know you’ll be happy, well-fed and taken care of.

Shannon: Which is what helps it stick in your head. When you think, ‘I want pancakes,’ you know you can get them here, you know how they’re going to taste, how much they’re going to be, and how good they were last time. You remember it.

Tyler: It kind of ensures our sustainability as well, because we’re giving people something they require more than once a month, which is a warm place to stay.

I’m firmly against restaurants and chefs that are not flexible towards the guests. If you are vegan, only eat raw food, or gluten-free, we’ll come up with something and it will be good. It shocks people so much that they have a hard time wrapping their heads around it. If it’s an unrealistic request that sacrifices the integrity of the dish…

Shannon: that’s where having an experienced front of house staff comes in handy, because they can speak eloquently. They’re going to find a polite and appealing way to describe an alternative.

How do you stay competitive and current in Toronto’s food scene?

Shannon: Social media is definitely a big part of it. I try to see what’s opening, what people are doing in social media, if they’re running promotions, if they’re working for people like Tab, or of any new trends. Shawn and I try to go to restaurants whenever possible. We have two small kids so it’s not alway easy, but we try to divide and conquer, and ask people what we have to try.

Tyler: Reading and staying on top of current trends not only in Toronto. I find that Toronto trends like to follow each other, where everybody likes to do the same thing for a while. For the most part, I try to avoid trends and just stay true to the food, its ingredients, its history, and the integrity of its preparation. Once in a while we’ll put some modern garnishes on things, but for the most part we keep it very simple. It’s kind of an anti-trend restaurant.

After what looks to be Shawn finishing some restaurant tasks, he joins us back at the table.

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Direction for cocktails?

Shawn: We had a smoked cocktail that came gift wrapped for the holidays.

Tyler: We’re all about kitsch, we’re not afraid to be cheesy

Shannon: Sometimes it really works. Whatever it is that gets guests to take Instagram photos or tell their friends about that great experience they had, then I’m all for it. We give a little brown paper bag of popcorn at the end of every meal with your receipt attached. People love it, they hashtag it.

Shawn: The kitchen makes it daily. It’s a honey fennel popcorn.

How do you prep for the day, and relax after hours?

Shannon: The first thing I do is take my kids to school, and then I have a routine of seeing what appointments I have. I have a lot of reminders set on my phone, and from there I decide what I have to do first. I finish my day in about the same fashion, from troubleshooting what needs to be done in a day, week, and month.

Shawn: Then Shannon tells me what I’m suppose to do for that day, and that’s what I do.

Shannon: we do try to take vacations a couple of times a year out of the country. On our downtime, I spend it with our kids. We try not to answer the phone too much, but other than that it’s all hands on deck, all the time.

Tyler: To relax, Manhattans, and once in a while I’ll take a little time off and go up to Owen Sound and spend time with my family. Usually, I start getting phone calls after I take my girl to school.

What’s the best part of your job?

Shawn: It’s eating Tyler’s food and drinking the cocktails. I love that this is my favourite restaurant. I love our customers here, because we have a good group of people who come here to eat.

Shannon: For me, I left my nine-to-five corporate job two years ago. As much as we don’t have “hours,” I love being able to make my own hours, and being able to take a vacation if I need to. I love the freedom of being your own boss, even with the stress it brings you.

Tyler: I love mentoring and watching young people grow, becoming better at what they do, and building confidence. From watching those cooks get compliments from people coming up the stairs, as they walk by the kitchen. It’s the look on their faces when they get a compliment for the first time.

Any go-to mobile apps?

Shannon: Instagram, Twitter, and Facebook, I’m on a lot, any mobile banking app, because I do all the banking for all our businesses, and the LCBO app.

Shawn: I use all my social media apps too, because I travel a lot. I have to admit I use yelp when I’m in a certain neighbourhood, although I wish people wouldn’t use it.

What’s in-store for 2015?

Shannon: Shawn and I are opening our third bar. The a bar, in a barn, in the Prince Edward county called The Hayloft, which was originally The Hayloft Dance Hall. It’ll open just when it’s warm enough to be in it, May – September. It is right beside Sandbanks Provincial Park, so there’s camping, wine country all around, and most people do B&B’s.

Shawn: It’s been there for 47 years, we’re just taking it over and making a live music venue for events.

Shannon: Here, we’re changing the menu seasonally, and we always have the Bloor Street Festival. It’s always fun because we get to have the patio for two days.

Tyler: We want to do our own thing; it’s an opportunity to learn something new. I think that that’s the way food and experiences might be going in the future, just because I think food itself is not enough to sustain people’s attention anymore. I think you have to create moments, and I would like to create more moments.

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About Amanda Chiu

Amanda is the Marketing Coordinator at Atomic Reach, writing posts, sharing news, and connecting with the community on the daily. Her attempts at clearing her ever-growing reading list continue to be unsuccessful, and she really does believe that sharing is caring.
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