Sarah Syman of The Dandy Crown: 5 Things You Need To Know To Successfully Run a Live Virtual Event

Take the first five minutes to introduce yourself and your background. I like to talk about my experience in the industry, a few places I’ve worked, and tell the story of how I started in the cocktail world. Offering up information about yourself will make the attendees feel like they know a bit about you. It will be more relaxed and willing to interact with you throughout the presentation.

As a part of our series about “5 Things You Need To Know To Successfully Run a Live Virtual Event”, I had the pleasure of interviewing Sarah Syman.

Sarah Syman is the brains behind the cocktail program at The Dandy Crown, a cocktail-focused bar and restaurant in Chicago’s River West neighborhood. Syman got her craft cocktail start at The Drawing Room and continued onto Public Chicago Hotel, The Dawson, Beacon Tavern, Otto Mezzo, and most recently, split her time between The Drifter and Beatnik. Syman has participated in numerous cocktail competitions, including Speed Rack, Heaven Hill’s Bartender of the Year, and World Class. In 2019, Syman was selected to join Tales of the Cocktail’s Apprentice Program, and in 2020, she was a member of the prep crew for the San Antonio Cocktail Conference. Sarah creates a warm hospitality culture where guests will feel at home, whether they want a High Life and a shot of Bourbon or to nerd-out about spirits in a meticulously prepared craft cocktail. The Dandy Crown is aptly suited for either experience in their laid-back-luxe vibe. Nestled in a stand-alone, two-story vintage brick building, the Dandy Crown interior seats over 90 in a combination of bar space and lounging areas. The first floor features a fireplace lounge surrounded by mid-century modern, comfortable chairs and couches, while the second floor offers overflow and private party space with another full bar. Adjacent to the property is a spacious and comfortably chic patio, seating 130, and open year-round with fire pits and heaters.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a bit about your “childhood backstory”?

I’ve worked in restaurants in Chicago for as long as I’ve been working. When I was a junior in high school, my first job was as a hostess at a now-closed upscale Chinese restaurant/club in the West Loop. I continued to work in restaurants on and off, in some capacity, ever since.

Can you tell us the story of what led you to this particular career path?

When I first moved back to Chicago after college in southern Illinois, I began working in art gallery management. I did that for three years after college, with one gallery in particular. When I stopped working at that gallery, I was becoming burnt out on the art world, so I didn’t try very hard to quickly get another arts management job. Instead, I began working full-time at the Wicker Park bar, where I worked as a part-time server, while still working at the gallery. Once I started working there full-time, I immersed myself in the menu and looked deeper at how much there was to learn and how many ways there were to grow within the industry, and I was hooked.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I don’t know that I have a particularly funny mistake I made, but I know I faked it a lot the first year I was behind the bar. I was learning at a very well-known craft cocktail bar in the Gold Coast, and the guests there often liked to ask a lot of questions about our cocktails and spirits, as they were curious about the process. I was just starting out; I only knew the basics, so I would give a lot of very vague answers and then come up with an excuse to run to the kitchen or the bathroom so I could pull out my phone and Google the correct answer before running back behind the bar. I probably could have just admitted that I was a newbie and referred them to one of the more experienced bartenders behind the bar. Still, I was too afraid of the guests looking down on me for not knowing the answer or worried that the other bartenders would think I was dumb. I guess the lesson there is to own your weaknesses and ask for help. That’s something I preach to my barbacks and bartenders who are just starting: no one should ever look down on you for not knowing the answer or how to do something. We were all that young bartender once, and, as someone with more knowledge and experience now, it’s my job to help educate and bring up those that are young in the industry.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

We jokingly referred to The PDT Cocktail Book as “the bible” when I started. At the time, it seemed to be the most comprehensive collection of classic cocktails. I carried it around everywhere I went and was always reading and earmarking individual pages with recipes I wanted to try to make. My goal was to recall any cocktail in that book from memory because I thought that’s what an expert cocktail bartender should be able to do. Spoiler alert: eight years later, I still can’t do that!

However, I often give that book to my younger bartenders and challenge them with doing what I did; earmark several cocktails they think sound exciting, or they’ve never heard of, and then go through with them, step by step, make, taste, and talk about each one.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

This speaks to a reasonably particular “life lesson”, but it’s left a lasting impact regardless. In 2018, I was at a Womxn in Leadership conference in Chicago (geared specifically toward womxn in the hospitality industry). During one of the earlier segments, there was a discussion about three prominent womxn in leadership roles about their experiences rising through the ranks and the challenges they faced while doing so. During the conversation, one of the womxn interjected: “We have to treat each other as if we’re all geniuses, poets, and artists,” and I thought it was just so brilliant. I quickly scribbled in my notebook to remember the quote but not miss out on anything else anyone had to say.

That quote stuck with me over the years, and I think it applies to just about any community you find yourself in. We need to not only treat each other well but lift one another as though we are each that genius, poet, or artist. When you feel confidence surrounding and amplifying you, especially in the face of challenges or disappointments, it just might be that extra push you need to succeed.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. For the benefit of our readers, can you tell us a bit about your experience organizing events in general?

I’ve worked at many bars and restaurants that would regularly do large events and buyouts, so I had many secondary experiences facilitating those. There always seemed to be many moving parts ahead of the event, but everything seemed to come together magically. In the last few years, I’ve worked on some large-scale independent events, doing cocktail batching, planning, prep, and building out displays for massive groups of people.

Since I began working at The Dandy Crown in the last year, I’ve gotten much more hands-on experience planning and executing events, from the very first email or phone call until the last glass is cleaned at the end of the party. As I suspected, there is a LOT more that goes into it! However, the biggest thing I learned throughout all of the events that we’ve done is the importance of communication. At the end of the day, the host and I want the same thing — for everyone to have fun at the event — and the only way to do that is to keep open communication lines between me, the host, and the staff working the event.

Can you tell us a bit about your experience organizing live virtual events? Can you share any interesting stories about them?

Virtual events are really interesting. On the surface, they share a majority of things with live, in-person events. There’s still a ton of moving parts, and communication is always paramount. There are many more logistics to work out — facilitating pick-ups or drop-offs safely (especially during a pandemic!), legalities of transporting cocktails, and ensuring the cocktails and garnishes retain their longevity and freshness.

Now, the biggest goal is creating a unique and enjoyable experience virtually, when everyone is separated. Most groups opting for a virtual cocktail party, demo, or class have been sitting in Zoom meetings for months now, so, inherently, a virtual cocktail party can start to feel like any other meeting. A big part of my job is to inject some energy and excitement and keep the attendees interested and engaged.

There’s a bit more of thinking on your feet that happens during a virtual cocktail event because there’s absolutely no way to predict what each group’s dynamic will be. I can come in with every expectation for how it will run, but there’s no guarantee it will pan out the way I planned. And that’s ok! I’m here for whatever the group needs, so I just have to remember what I think is essential to teach and talk about, and then I let the group dictate the flow of the presentation.

In your opinion, what is an example of a company that has done a fantastic job creating live virtual events? What specifically impresses you? What can one do to replicate that?

Tales of the Cocktail is a HUGE cocktail conference that (usually) happens once a year in New Orleans at the end of June. Industry professionals worldwide travel there for a week of education, conversation, and celebration. With the pandemic completely taking over this year, they had to move their conference online. For four days, they offered a wealth of virtual seminars with industry leaders, sparked conversations within our communities, and even had a virtual awards show. While certainly unlike any Tales of the Cocktail I’ve been to in the past, it was incredibly impressive the amount of content they could make available and the amount of reach they could get.

Tales of the Cocktail has a huge team, so I imagine delegating responsibility for different events played a huge role. Allowing various team members to have ownership over different parts of the week ensures that much focus is placed on each virtual event.

What are the common mistakes you have seen people make when they try to run a live virtual event? What can be done to avoid those errors?

I’ve seen some events where the presenters or speakers can’t roll with the punches. They get caught up with the awkwardness of a virtual presentation, stumble over their words, or just generally can’t get across the point they’re trying to make. I think the best way to avoid that is to make sure you know what you’re talking about, like the back of your hand! That way, whatever unexpected curve balls get thrown your way, you can pivot and still get your message across.

I’ve also seen some events where products were supposed to be distributed to the attendees but didn’t make it there. While that’s not always the presenters’ fault, it’s still important to meticulously check and triple-check your outgoing packages before they leave your possession.

Also, most importantly, making sure you have a stable, strong internet connection. There is NOTHING more embarrassing than being expected to present to a virtual group and having your internet decide it doesn’t want to work in your dining room! If you can’t tell, that specifically happened to me when I was supposed to be doing a cocktail demonstration as a part of a more extensive happy hour. My internet was weak in the dining room, and I continually froze while making this cocktail. I eventually had to give up. I will no longer be attempting to take a Zoom call from my dining room!

Which virtual platform have you found to be most effective to be able to bring everyone together virtually?

For something official or professional, I’ve had the best experience with Zoom. For just groups of friends hanging out, Houseparty is the most fun!

Are there any essential tools or software that you think an event organizer needs to know about?

Good internet, a working microphone, and a camera are the essential tools. Those are the only essentials. Also, be mindful of your background. Make sure it’s appropriate for your event and nothing inappropriate can be seen!

Ok. Thank you for all that. Here is the main question of our discussion. An in-person event can have a certain electric energy. How do you create an engaging and memorable event when everyone is separated and in their own homes? What are the “Five Things You Need To Know To Successfully Run a Live Virtual Event” and why? (Please share a story or example for each.)

1. Take the first five minutes to introduce yourself and your background. I like to talk about my experience in the industry, a few places I’ve worked, and tell the story of how I started in the cocktail world. Offering up information about yourself will make the attendees feel like they know a bit about you. It will be more relaxed and willing to interact with you throughout the presentation.

2. Dress up your packages with something unique to your business. We label each of our bottled cocktails with our logo, address, and ingredients in the cocktail. I also include a little postcard with a thank you. It’ll help to bring a bit of your business’ personality to someone else’s home.

3. Ask questions of your attendees! While you may be the focus of the presentation, it’s important that the attendees feel comfortable asking for clarification or for you to go more in-depth about something. As the presenter, you have a wealth of knowledge on the subject, but allow the attendees to help dictate the course the conversation takes.

4. Be flexible! If everyone wants to sit back and mute themselves just to listen, allow that to happen. If they want to listen for 5 minutes or talk amongst themselves for 5 minutes, let that happen as long as it’s all within the agreed-upon presentation length.

5. Have someone there with you who can help troubleshoot in case something unexpected happens. In case you run out of something, drop something, the internet drops, whatever it may be — the second set of hands will help minimize the amount of time lost on the event and will get you back up and running quicker than if you’re trying to do it all alone.

Let’s imagine that someone reading this interview has an idea for a live virtual event that they would like to develop. What are the first few steps that you would recommend that they take?

Have a date, time, and length of event in mind — that’s likely going to be the first question someone who’s going to facilitate this will have for you. Beyond that, if there are any “musts” or themes for the event, make sure to communicate those clearly. Most of us in the bar world are excited and eager to help plan and execute these parties, and have a million different ideas of how to do that, but our ideas aren’t always what you have in mind! Give us a roadmap, and we can help fill in the gaps.

Super. We are nearly done. Here are our final questions. You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I would love to see even further strides made toward gender equality, both in society as a whole as well as the workplace. Being a white woman, I have inherent privileges that have allowed me to navigate specific workplaces better than others have. However, being a woman in a management position can still be a challenge, and it was certainly not a walk in the park for me to get to where I am.

That being said, I have had far fewer life and workplace struggles than women of other ethnicities and skin colors have, as well as those individuals that identify anywhere on the gender spectrum. We have begun to have the conversation about disparities and biases, but that is all we’ve done. We have only just started the conversation. I would love to see the world move toward a greater acceptance of all humans, based on knowledge, merit, and kindness, rather than what someone looks like or identifies.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

I just finished watching the West Wing, so I’m going to go with Allison Janney. She seems like she’d be a lot of fun to sit down with!

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.