This interview was edited for length and clarity.Soon, David Caruso will celebrate 25 years of planning many of Milwaukee’s biggest and most meaningful celebrations through his business, Dynamic Events. And he couldn't be more jazzed about it.

A few of the events Caruso created include the Baird Center Grand Opening Gala; the Milwaukee Bucks Foundation’s Sixth Man Soiree; Heart of Canal Street at Potawatomi Casino Hotel; Aurora Healing & Advocacy Services’ Hope Shining Blue; The Big Gig Dress Rehearsal – Uptown Hoedown; Rite Hite’s Celebration of Service; the Republican National Convention Welcome Party and many more.

Caruso is also the host of “Milwaukee Made," a three-episode TV series by Visit Milwaukee and TEAM LAMMI that explores the city's vibrant culture.

Smart, creative, organized, stylish and thoughtful are all qualities possessed by Caruso (sorry, folks, he's married) and are integral to his event planning and television hosting success. But what really comes through in Caruso – and conjures extra magic in his projects – is his passion for Milwaukee. 

Born and raised in Wauwatosa, Caruso was the youngest of four children, and the only boy. He says he learned a lot about life from his three older sisters.

“I always feel grateful that I was the youngest because it gave me an opportunity to observe things through a different lens and create my own path," says Caruso.

His loving and supportive family made him the confident and capable man he is today.  

“My mom is very creative and she always, no matter what, gave me the space and freedom to try things,” says Caruso. “So I really didn't grow up with reservations. It was wonderful. It made me comfortable in who I was and confident that I could do a lot of things.”

During grade school, he became involved with community theater, which was life-changing for him. 

“Being in the theater was really a great place for me to develop around other creative people. That's where I fell in love with production. Creating things. Creating environments. Creating scenes,” says Caruso.

Caruso graduated from Marquette University and, after a brief time in Chicago, returned to Milwaukee for good. He currently lives in Milwaukee's Enderis Park neighborhood with his husband, Adam, and their dog, Miss Mabel.

“I’m incredibly fortunate and blessed with my career and my family,” says Caruso.

OnMilwaukee: What were the early days of your business like?

David Caruso: It was a “fake it 'til you make it” type of situation, but I always knew I could do it. I was never nervous about it. I didn't have any doubt. The hardest part was getting the traction.

The event that changed the trajectory of my early career was the grand opening of the Milwaukee Youth Arts Center. There were two really fabulous women who were co-chairs of that event, and they had seen my work, and reached out to see if I would help them with their event. From there, it was a little bit easier to get people to talk to me, consider me, and ultimately hire me to do some of these most talked-about events over the past almost 25 years. 

So what makes you so good at this? I know you can't give away all the special sauce, but why is event planning a natural fit for you? 

You know, it's an excellent question, and I think one of the things that has given me the confidence over the years is exactly what you said: what is it about you? This is why I don't get nervous about competitors. Because it really is about the event producer as a person that makes events special and unique. So much of what you see in the events that I have the privilege of producing is my heart and soul. It’s my creativity, my mind, my energy that’s bringing a client's vision to life. 

For me, ultimately, I love to produce experiences that make people feel something. Something that is very engaging. Very immersive. Something that tells a story. I figured out how to do this in event experiences and it gives my events a signature stamp. Often times, as soon as people arrive at a party or celebration, they tell me they knew it was one of my events immediately.

There are a lot of people who can make things look great, can put on a great party. But there is another layer to it. And I have really honed in on that part of my ability and turned it into something very special.

What event are you most proud of doing?

Most recently, the opening of the Baird Center. The Baird Center is an unbelievable gift for our community, for our region, for the convention industry as a whole. It’s something that we should be so proud to have in Milwaukee. And when Marty Brooks (president and CEO of the Wisconsin Center District) and his team approached me to be the lead producer for the grand opening, I was beyond ecstatic and so excited because of how much I love this city.

Even more recently, just a few weeks ago, The Big Gig Dress Rehearsal Uptown Hoedown was so much fun. It was Country Western to the max. People showed up dressed in cowboy hats and leather pants and fringe vests. They really got into it. And it made it even that much more fun to be a part of. 

Do you have fun during the events you plan? Or is it just a blur?

I do have fun, first of all. And yes, at the same time, it is very high stress. But I learned really early on in my career the importance of remaining calm. Clients have told me that’s one of the qualities they appreciate in me the most. I listen, I observe, and I stay calm and positive. 

If there's something that needs to be dealt with, I do it behind the scenes. Or if I need to shake something off, I allow myself to step out and take a moment. 

People ask me for tips about entertaining at home – and it's the same as a large event. The host’s energy has a huge impact on how the guests experience the party. And so, whether someone is hosting a small dinner party or the grand opening of the Baird Center, the energy that you give is going to have a huge role in the overall vibe. 

Also, I am completely aware this is a fun business. It’s a party. I truly enjoy myself while staying very focused on what needs to be done. And finally, I never forget that my work is a privilege. I am creating a once-in-a-lifetime experience. 

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What's your dream event to plan anywhere in the world? 

I’ve had a dream this whole time, and I'm not afraid to talk about it, because I do believe talking about dreams is how they come to fruition. 

I grew up in the age of the Oprah show. I was glued to the television when Oprah was on. Some people might think that's kind of cheesy or they are really not into Oprah, but for me, she was a person who I related to very early on. Even though I was very young when I started watching her show, I knew she was doing what she loved and in her own style. So my dream is to do an event that is somehow associated with Oprah. 

You do events outside of Milwaukee too, right?

Yes, around 12 years ago, I started traveling to do events in other parts of the world. I just got back from doing an event at the Four Seasons Resort in Tamarindo, Mexico. The experience of doing events in other regions of the globe has really transferred to making what I do here even more special. I get to see what hospitality is like, what standards are like, in other places, and I incorporate those things at events here at home. 

You are also a great television show host. How did that aspect of your career start?

Coming out of the pandemic, I had the idea to start a television show. The first iteration of it was called, "Good Things Brewing." We did it for two seasons, and the second season was Emmy nominated. Now, I’m doing the show with Visit Milwaukee and it’s called “Milwaukee Made.” Our first season just aired across 13 markets in the Midwest in June. It's been a really, really fun project.

Part of why I wanted to host a show with Visit Milwaukee was because there were so many things that I love about Milwaukee. We have architecture that's unmatched. We have an entertainment and performing arts sector that is just unheard of for a city of our size. The lakefront, the parks. It is endless what makes Milwaukee awesome.

I think we (Milwaukeeans) are finally in a position of not being bashful. We're finally like, yes, let's shout it out to the world. This is a super special place for so many reasons, and I just love that I not only get to experience it every day, but I get to be a part of telling that story. 

You've ran your business for almost 25 years. How has Milwaukee changed during that time? 

Gosh, in a lot of ways. But specific to the event industry, people have truly realized that doing events, investing in quality experiences, and working with people that are able to communicate your mission, your vision, your story, all of those things in a live experience, in a well-done way, has a huge impact. 

We have drawn major conventions, like the RNC, major music experiences and theatrical debuts and so many other large events because Milwaukee has developed in a way that the rest of the world is noticing. No matter what people's politics are, the RNC put Milwaukee on a new map in terms of that level of caliber experience – and it was locally produced. 

Would you say it’s the details that make an event great?

Ah, yes. I always pay very, very close attention when I'm talking with clients. One of my favorite things to do is have chill conversations with people who are getting married and get into the nitty gritty. I want to know their story and then infuse elements of that into their celebration. 

It's not just about making things luxurious and over the top. What I love is when people walk into an experience that is luxurious and over the top, but they start noticing the details – the little touches, the personalized aspects. And when people feel that they're in a personalized environment and that there was intention behind everything they see, they completely relax and have fun. That's where the magic happens. I can't tell you the number of times I have checked in with guests or said, "How's your evening” or “I hope you're enjoying yourself,” and they tell me the event feels just like the couple or it feels just like their granddaughter. To me, that is so special.

Here's a funny example. I had a client who is a medical examiner for the city and she was getting married. She was extremely passionate about her job and a really smart, fun, quirky person. One of the things I did to personalize her wedding was ask the baker to put two legs coming out of their gorgeous wedding cake and hang a little tag from one of the toes. I didn't tell the couple about this, I just did it. And I'm telling you, it was the talk of the night. Everyone loved it. And it was nothing. Like, it didn't cost any money. It was just a thoughtful detail.

Here's another one that I was just thinking about the other day: Right after the Calatrava addition was added to our art museum, I went in there and saw that big hole in the middle of the floor that looks down into the parking level. And I immediately thought that, at some point, I had to find a bride who wanted to rise out of the floor. Long story short, and many, many years later, I remember walking into the art museum with a couple that was getting married and I was showing them the venue to consider for their event. The first thing the bride-to-be did is walk right over to that circle and look over. I was like, “Oh, my God. This is her. I found my Beyoncé bride.” I walked right up to her and I said, “Do you want to rise up out of that floor?” And she said, “I don't care what else we do for this, but yes, I do." 

I love your confidence and that you are willing to take risks.

That's part of it for sure. I'm not afraid. I just want to open up my client's imagination and their creativity and their minds to possibility.

What I'm really, really, really blessed to have are clients who completely trust me. Because in order for these experiences to be extra special, they're very customized. I'm not just pulling pictures off of Pinterest.

What are you working on right now? 

I'm super excited about this: at the end of the month, the National Association for Catering and Events is bringing a conference here for the first time. I have the pleasure of producing the opening reception at the Harley-Davidson Museum called “Fresh Vibes MKE.” It's gonna be a really super cool celebration of all Milwaukee is and I cannot wait. 

Another very exciting project coming up is the Wisconsin Athletic Hall of Fame’s 75th anniversary induction ceremony that’s happening at the Baird Center. The grand opening of the new Associated Bank Theater Center for the Milwaukee Rep is going to be extraordinary. Bernadette Peters is performing at the opening party.

Do you ever just lounge around the house? 

Absolutely. Being outdoors in our backyard and gardening and tending to the lawn is my relaxing time. If I need a break, I’ll go outside and do something in the yard and then come back to my computer and be ready to go. I've always been blessed with being able to sleep very well. That really, really helps, because otherwise, in this kind of environment, there are so many things always on my mind that could keep me awake.

What is your creative process like for event planning?

I always tell people that I appreciate being given grace and space because as a creative person, I need those things in order for ideas to come to light. Sometimes it takes me a minute to figure it out. I need to get to the moment when I'm feeling it, and then I'm like, "Oh, my God! I've got this!” I'll run to my desk and get to work. Sometimes this happens at really odd times and people understand this about my creative process. It isn't about checking off a task list or a timeline. If someone goes with the David Caruso experience, they know they are going to get something really special. That comes with an understanding that a lot of my process comes from organic creativity, and there needs to be a trust in that process. 

When people invite you to events, are they nervous, thinking you might judge or compare their event to one of yours?

When I get to go to an event that isn't mine, honestly, it’s so great for me to just be a normal guest and chill out and just experience it. I really have no interest in judging it at all. The hardest thing is when people come to me and they say, "So what do you think?" That’s the worst question, because I don't want to think about it like that. I just want to enjoy and have fun.

As your social media friend, I know you and your husband love to decorate your home. Is it fair to say that Christmas is your favorite time? 

Yes, yes, yes. Christmas! You are absolutely correct. Our house is definitely our sanctuary. We love it to be a reflection of our personality and who we are. Thankfully, me and my husband, Adam, are very, very in sync about our environment, and it is so much fun to create it together. So we love, love, love doing that. We get to make a lot of choices. We have a French bulldog, Miss Mabel, who we love dearly, but we don't have kids. So we can create our house exactly how we want it. When we moved into our house, one of the bedrooms had been used as a nursery by the previous owners. But we put in leopard print carpet and made it a dressing room.

And yes, Christmas is by far our favorite time of year. We have eight Christmas trees. They're all decorated differently. It takes a strong commitment and a lot of time to decorate our house. We have to take a lot out of our house to make room for Christmas. That's how crazy it is. And we do it, mostly, because we like to have people come over and enjoy it. Last year at our Christmas party, our favorite pianist was playing the piano and our neighbors and friends were singing at the top of their lungs. Adam turned to me and said, "This is a dream come true." 

I read somewhere that you're a wicked ping pong player. Is that true? 

Now, that's impressive, because that’s a hidden talent of mine.

How did you become such a good ping pong player? 

Growing up, my family had a ping-pong table in the basement. I also played tennis with my dad. Somehow, I never mentioned this to Adam, and a couple of years ago we rented a beautiful cabin Up North with some of our family. The cabin had a ping pong table and on one of the evenings, I started playing ping pong with Adam, and everyone was shocked at my ability. They were literally getting out their phones and taking videos.

Adam was really surprised too because he never knew that about me. So now it’s kind of a joke and when we meet new people, Adam likes to share that I’m a kick-ass ping pong player. 

How many years have you and Adam been married? 

We have been married for almost six years. We've been together for almost 10. And what's really funny is, when I turned 40, I said to myself, “OK, I don't ever think I'm gonna get married.” I never imagined that for myself. I was – and am –super career-focused. So for my 40th birthday I decided, because I would never have a wedding, to throw an amazing, fabulous-at-40 birthday party at Bacchus. It was really incredible. And then, two weeks later, I met Adam.

Did you plan your own wedding?

We planned it together. And that is what was really cool, because, of course, I could have just planned the wedding. But it was so much fun because we really did do it together. It was very “both of us” in so many ways. But Adam did say in front of 250 guests, "Can you imagine what it's been like for me to plan a wedding with David Caruso?” 

Other than budget, what makes a great event? 

Spending lots of money is not it. You can have a very beautiful, meaningful experience anywhere. In a place like this (Discourse Cafe) or sitting around a firepit with friends in your backyard. If you put the thought and effort into the experience you can make it literally unforgettable. And that’s what makes going through this journey of life so much more special. 

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