Episode 1: Fantasy Fest & Event Planning with Nadene Grossman Orr

July 18, 2019

Q:​ First time in Key West, a week before Fantasy Fest, right out of college.

A:​ I had no idea what I was in for.

INRO ~ Welcome to the Backyards of Key West Podcast with your host Mark Baratto. 

Q:​ We have our very first guest and I’m very excited to have her. I don’t know if I should say both names, is it one name?

A:​ It gets tricky.

Q:​ Let’s get people educated here on this first episode.

A:​ I was the eternally single girl, so I kept my maiden name and started my business under my maiden name. Now I have a married name, and you know, my husband gets upset when I get called by my maiden name, so I just kept them all in there. So, they are all in there. Nadene Grossman Orr.

Q:​ Nadene Grossman Orr, see that was like in unison too, we could never have planned that. 

A: ​That was pretty good.

Q:​ That was nice.

A:​ And no hyphens, I am opposed to the hyphen. 

Q:​ Cool. Well it sounds even more impressive because it’s one…

A:​ Well, it’s just hard to say. 

Q:​ Do I say hyphen, Orr?

A:​ No. No. No hyphen 

Q:​ Well, if you are a local Key West’er, and I don’t know if I’m even supposed to say Key West’er down here, we can get to that in a second, but if you are local, you definitely know that name. You’ve heard it and if you’ve not, then you have been attending one of the festivals that she puts on for sure. 

A:​ Yeah.

Q:​ So, let’s educate the people a little bit.

A:​ Yes, that’s a safe bet.

Q:​ Yeah, let’s educate the people a little bit more. But we can start with Key West’er. Should I be saying that? Being a new person.

A:​ I say that. I say I’m a Key West’er. Yeah, I think I’ve said that a time or two. 

Q:​ And then what about the…

A:​ Just a local.

Q:​ So, let’s just get this thing out of the way, right away, which is this conch, fresh water conch, like, okay so educate us on that.

A:​ And you are ahead of the curve because you said conch (pronounced “conk”), instead of conch (pronounced “consh” which is incorrectly). You, don’t go there.

Q:​ No. Not gonna say “consh.”

A:​ You go into a shop and ask for your local “consh” discount.

Q:​ Yeah, I’ll have a “consh, a fried consh,” yeah.

A:​ Yeah, I’ve been here a really long time now, so I don’t know even what my status is, but… 

Q:​ Well, if you’re born here right? You’re a conch.

A:​ Right, so my daughter, yes and, in fact, in Key West, in the hospital here they give you a little onesie that says that you’re a conch.

Q:​ Aw, that’s cool. I think after five years, you’re now a freshwater conch? 

A:​ I don’t know, maybe seven?

Q:​ Maybe seven?

A:​ I think it’s seven.

Q:​ I’m sure I’ll get the social media tweets.

A:​ You’ll get the memo. The postcard comes and says “Well, sir.”

Q:​ And then I’m just here a couple of months. So, I’m just a local.

A:​ Uh?

Q:​ Or, am I not even a local?

A:​ Uh? You know I think that people would argue that, you have to be here for a little while to earn your local status. 

Q:​ Okay, so I’m just a …

A:​ I’d say you are a local when you get recognized the places that you go. And the locals embrace you, and then you’ll seem like a local.

Q:​ So, I just live on Key West. I’m allowed to say that, I have a house and I live here.

A:​ You can say you’re a local, I won’t tell.

Q:​ Okay, well, I don’t want to get anybody mad. Especially on the first episode.

A:​ Well, you’ve been here a lot of times. You’ve visited.

Q:​ Yeah, well, being from Miami, we’d come down here a lot, but I don’t like to tell people that I’ve lived in Miami.

A:​ No, you shouldn’t. Yeah, I think even people say, “Don’t Miami my Key West.” 

Q:​ Yeah, right. Which I am not doing. I don’t drive a Lamborghini.

A:​ Don’t do that.

Q:​ I am not snobby.

A:​ That would be frowned upon down here.

Q:​ Yeah, I usually don’t wear socks. So, I’m fitting in already.

A:​ You are, it’s perfect.

Q:​ Yeah, okay so… let’s ask you this, “How long have you been in Key West?”

A:​ I came to Key West in 1991. Fresh outta college. So, I’m going on 28 years here in Key West. 

Q:​ And what was the reason, were you just like, I want to go visit.

A:​ I graduated college and I got a little job in my hometown of Port Jeff (Port Jefferson) on Long Island. I got a job in an art gallery, I had been an art major with… sociology and art.

Q:​ First job outta school.

A: ​First job outta school, yeah, an art gallery. You know it was kind of a schlocky little art gallery, it’s not open anymore, so I can say that. Right? Yeah, and it was kinda like the tourist town like paintings, driftwood frames, and mix and match the frames. But the owner of the gallery was a super great guy and he opened up a gallery on Duval Street and asked me to come down here and run the gallery for him in Key West.

Q:​ And, had you ever visited before?

A:​ I had never been to Key West. Never been.

Q:​ Wow.

A:​ Never been, so I credit Paul Welch, that is his name.

Q:​ Shout out to Paul.

A:​ Yeah, cool guy, shout out to Paul. I think he’s back in Massachusetts now somewhere, but yeah, he got me to Key West. I managed the art gallery for him for about a month, well, he went on his honeymoon and did some traveling and I fell in love with Key West. I really did.

Q:​ Wow. And do you remember what time of year that was?

A:​ Well, funny enough, it was about a week before Fantasy Fest.

Q:​ Oh my God. So, first time in Key West, a week before Fantasy Fest, right outta college.

A:​ I had no idea what I was in for, and I’m working in the gallery one day and in comes this little senior couple and she’s got him on a studded collar and a chain and they are wearing harnesses and all the accoutrements. I’m like, “Wow!”

Q:​ Whoa.

A:​ What is going on here? That was my introduction to Key West. But I loved it, I love the island, I love the people, I loved everything about Key West, I loved the small-town feel, I loved… I think one of the things I loved the most was the smell of the island.

Q:​ Like the ocean?

A:​ The ocean, the way the island smelled after it rained, the flowers, you know? Just walking around town, especially in the evening time and the whole island just smells like flowers. And I still love that.

Q:​ Yeah. And I’m sure February, no freezing cold rain was a thing, you didn’t miss that either, coming from New York.

A:​ Right. Yeah, Long Island winters.

Q:​ The breeze on the beach is great in the summer, but in the winter, it is just brutal. So what year was that? How long ago was that?

A:​ That was 1991. Yup, I graduated in May or whenever and moved down here in October. 

Q:​ And never a thought of, “Well, maybe this isn’t for me, you just hit the ground running and really loved it.” 

A:​ So, it was a great deal because I had his little apartment and this little Nissan Pulsar ridiculous car with T-tops, but I thought that was pretty cool. You know, I was 22 and thought, this is great! I’ve got a car, an apartment, I’m living on an island.

Q:​ Right, you are like working on Duval Street.

A:​ There’s a cute guy delivering pizza. All these cute little boat boys, it was a lot of fun. So, after I was here for a month or so working in the gallery, I decided this is it, I’ll just move to Key West, why not? I went back home, packed up a suitcase, my mother thought I was crazy and I think she lectured me for about 48 hours straight while I was home. About how crazy I was and I was like, “Okay, see you Mom, I’m outta here.”

Q:​ Yeah, like sure Mom, I’m outta here.

A:​ Alright, you can come visit. And I moved down here with a couple of suitcases and a box and very little money in my pocket, but you know, I’ve come a long way.

Q:​ Yeah, and how long did you work in the art world?

A: ​I worked in the gallery about a year and a half or so, and then I decided I needed to do something more Key West’y. There’s that word, right?

Q:​ Yeah, which was?

A:​ So, I started working for Sebago catamarans and I worked on the boats and I worked in their booth in the seaport, checking folks in to go out snorkeling and sailing.

Q:​ Is it cause of these boat guys? The boat men you talked about? The boat boys?

A:​ Yeah, lots of cute, you know there’s a funny joke I like to tell about, “What do you call a boat mate in Key West without a girlfriend?” 

Q:​ What?

A:​ Homeless.

Q:​ Yeah, I see that already.

A:​ That was the joke back then. Yeah, I definitely, enjoyed the boat boys.

Q:​ The boat life.

A:​ Yeah. The boat life and to this day, I think I had so many influential people, that have influenced my time in Key West, and that I actually still do a great deal of business, to this day that I met while I was in the seaport there for Sebago. People coming and going and like, back then Richard Hatch and his wife who have Blue Heaven Restaurant. They lived on a boat and they would come in on their boat with their two kids and they would have coffee with me at the Sebago check-in booth at the seaport.

Q:​ Wow.

A:​ And then head into town to work. Mel Fisher used to shuffle by my booth, you know, with a cocktail and a banana and tell me a story and pull out a pocket of emeralds, and I mean, I have just, it was an amazing time. I met so many people, just hanging out in the seaport all the time. I’d ride my bike to work and it was great.

Q:​ Wow. And then you got into being a concierge. Like in the concierge type business.

A:​ Right. So all that time, like you know working on the boats and working in the industry first hand and actually after that gig, I was a cocktail waitress and worked at the Hogs Breath, and that’s how I met Charlie Bower, who would become, and you know I would work with him in the songwriter’s festival to this day. But I met him back then, so, yeah, concierge, boat crew, cocktail waitress, I’ve got all the C’s in there. 

Q:​ Yeah.

A:​ Yeah, but I really learned this industry from the inside out. I worked it. I worked it.

Q:​ Right. Understanding the people that make and add the most value that come to visit, which is what supports the island. 

A:​ Exactly, and I know you know how it will work, and why it will work, because I’ve actually done a lot of it, ya’ know? 

Q:​ Well, that’s the thing, sometimes, and we’ll get into what you do now, but sometimes when you’re running a business from a high level, making these decisions you may not know what’s really going on – on the ground. Who the people are, really managing and running this thing are feeling or acting, and you live that, and you know a lot of those people. So, it makes it easier to manage both expectations, right? That of running a big business and the other, understanding what goes on, and mechanics that go on.

A:​ Absolutely. Yup.

Q:​ So, let’s segway into what you are doing now.

A:​ Oh, well, what am I doing now. A little bit of everything. So, after my cocktail waitressing, and my boating, and then I took a job as a concierge in the hotel industry and worked in the hotel industry and in the hotels for a long time, and I loved what I did. I loved the tours and industry, and I thought if I could do just a little bit of what I was doing for this great big hotel company for myself, then I would be able to keep the lights on and support myself. And I took a leap of faith in 2004 and I started We’ve Got The Keys, and knock on wood, I’m still doing that to this day. We are a destination management company.

Q:​ So, what. Take me back to what you were thinking, it was a while ago when you started this, so what were you thinking going, “I’m just going to start this business.” Because a lot of people dream about doing these things and not many people take this kind of action. So, what was that drive?

A:​ If I look back at it now, I think it’s kind of like having kids. If you knew all the stuff you were going to have to deal with? 

Q:​ You’d maybe not do it.

A:​ Ah, you would probably not do it. I learned as I went, but I had a lot of great role models and a lot of great influences and a huge support system. You know, this little island? I suppose it either really embraces you and lifts you up or it chews you up and spits you out, just as fast. But if you are a really hard worker and you are really dedicated and you have made the right friends along the way, I mean, I can look back and think you know, and still I rely on a lot of those people for resources, influences, and ideas, or just to bounce something off of them. 

Q:​ Well, was it anybody in particular that you were talking to that gave you that push or that nudge? Or was it just all inner.

A: ​It was me. It was definitely it. My mother, well I had just bought a house and my mom said, “Well, you know I can’t pay your mortgage for you, if it don’t make it.” Thanks, Mom! I’m gonna do it anyway.

Q:​ Well, sometimes there’s a little bit of “look at you”in there, you know, in a good healthy way, right?

A:​ Right? No, and it worked out alright and she is so proud of what I do. And I don’t think she really understood it, but I remember four or five years in, I was hosting a huge event at the Hemingway House and they happened to be in town and she came by and you know, the light went off and she was like, “Oh, now I understand what you do.” 

Q:​ And shew as like, “It was all my idea.”

A:​ Right? That’s an interview for a whole ‘nother day. 

Q:​ That could be a part two, but in a darker episode. That’s over the cocktails.

A:​ We’ll need cocktails for that, for sure.

Q:​ Yeah. So, what business would your friends say you’re in?

A:​ Well, I’m sure that they would say that I’m an events plan, events girl, I’m an events planner.

Q:​ So that if someone, but, not in the wedding space. So, do they know that? Or are they like, “Joanne’s coming out for a wedding, could you plan it.” And you’re like, “uh no.”

A:​ I still get those questions and for some people, I will definitely help and you know, we did weddings for a very long time. So, when I started the company, I knew I would need to do destination weddings in order to make it sustainable. The corporate business has taken a really, really long time to find and establish that network. But weddings in Key West are a sure thing. Key West is like #3 destination for weddings and it’s still hugely popular destination. It’s big business.

Q:​ Yeah, but I’m sure it’s like any other business, all these new topics that are coming up. People are like, “Ah, the quick buck!” and I like this and there must be millions of people trying to migrate down here and start another wedding events business and they come and go. 

A:​ Yeah, I can probably rattle off a lot them, there are several. Some of them who worked with me over the years and have gone out and done their own thing and are incredibly successful at it to this day. And now, I have a great place to refer all my wedding business. But, yeah, if you are doing this job right, you make it look easy. And then, other people think, “Well, I can do that.” And you know, it’s definitely not easy and it’s not glamorous and all the things.

Q:​ Nobody understands. But everybody always sees from a tech world standpoint, everybody always sees …Oh, the big break. They see the company being sold, or the actor in this movie gets the Oscar, but they don’t see like the 20 years of eating dog poo that came along before you actually got that. 

A:​ It hasn’t come to that yet.

Q:​ Yeah, there was never this, like, overnight success, that doesn’t exist. Really.

A:​ No. No. It definitely wasn’t overnight and like I said, Key West can chew you up and spit you out or it can really embrace you and I’ve worked really really hard. I know how important those relationships are to maintain and manage and support and network. And you know, so even what we do, the root of what we do is, as destination management, is that we work for our clients to curate the perfect Key West experience. But I’ve always held the belief that I’m working as much for my clients as I am for my vendors. My event partners. So, I have been able to strike a balance, I feel like there is always a win – win. There’s always a way to do something within the best capabilities of my vendors to keep the client happy.

Q:​ Well, you understand both because you’ve worked in that vendor type world and now you’re working in the other side of it, so you kinda want to help both people out.

A:​ Absolutely.

Q:​ And you never thought of, oh my business is successful here, I want to branch out to other parts, or you’re always like, you’ve been a Key West girl from day one.

A:​ Yeah, you know it’s funny, so the name of my company, We’ve Got the Keys. I chose that name because I thought, well it doesn’t limit me to Key West. We’ve got the Keys, all the Keys. 

Q:​ Exactly.

A:​ I can work in all the Florida Keys. 

Q:​ Yeah.

A:​ And I imagined, that I would. But, you know, I’ve been, well I keep myself busy down here in Key West and I love that I have become an expert, you know, in what I need to be an expert in. Also, I recognize the strengths of my vendors and my team and I’ll let everybody be an expert at what they’re experts at, and just sort of choreograph it all together.

Q:​ So, no, you’re not doing the #1 mistake that bosses do, which is over micromanage. 

A:​ No.

Q:​ Which I don’t see you do.

A:​ No, I am not a micromanager, no.

Q:​ Well, I also see you as a people person, and I think that if you had business that was three hours away, it would be harder for you to shake hands and meet face to face. I take it you like to do that.

A:​ It would. I am very hands-on, I’m in the trenches setting up, rolling tables and I’m there at the end of the night cleaning up and hauling out the garbage. You know, eating behind the scenes with the catering staff, so I’m very hands-on.

Q:​ That’s the only way to do it. So, how do you see that your business has changed since you started, besides the growing pains of it. Just, in general, Key West with the business.

A:​ The business has evolved and we did many, many destination weddings. Almost 800 of them, I would say over the time, and then in 2015 we stopped doing that, and were able to focus and sustain ourselves on the corporate events. We also took on a few city-wide festivals, a few more, I would say, and we have been very fortunate. I think probably the biggest, I don’t know what I would say, I would call it a tip or advice, or whatever, I’ve always grown my business to the strengths of my team. My team has changed a lot over the years, I’ve had many wonderful employees and some, that you know, it wasn’t quite the right fit, but we have always evolved my business to the strengths of my team. I think it’s one of the things I love most about it, really, we could do anything.

Q:​ Right.

A:​ We do events, parties, we go after different markets because that’s the strength of my team and experience that they bring from where they life experience has come.

Q:​ So, I don’t want to put words in your mouth, but it sounds like the no micromanaging and the believing in your team is the advice you would give to someone wanting to even get started in any business. 

A:​ For sure. Absolutely. If you build up your team and play to their strengths, you can’t fail.

Q:​ Yeah. And the thing is, even in my experience in working with a number of businesses, a lot of times, the owner is always thinking and acting like, these employees I have over here, can never it do it as well as me. So, let me jump in there and always tell them what to do, and that may be the case that they are not as good of an operator as you, but they are experienced in other things. It’s better to have ten people working at your 80% than two at your 100.  And, you’re going crazy and they’re unhappy and you’re unhappy. 

A:​ Right. You know, and I think that, I mean, yeah. If you put it that way, absolutely. But also, I love the brainstorming. I love the creative process, so we and my team and I spend a lot of time just kinda talking about great ideas and I make sure it’s one of the first things I say when I bring on a new team member. Don’t ever be afraid to say whatever crazy thing comes to mind and say what you’re thinking and say, tell me about your experience, and you like it, you don’t like it, you know we pick it apart and put back together and make it that much better. But, yeah, there’s no… creative brilliance, let everyone shine… I think I lost my train of thought there.

Q:​ Nope, that’s right on. Yeah.

A:​ I zoned out on you for a minute there. 

Q:​ You were getting all psychedelic on us. 

A:​ Yeah, but we have had great strengths and I don’t micromanage them at all. I think that currently, my current team, I mean they are even better at doing the things that they are doing, than I would be. So, I just, I am air traffic control. We just direct, divide, conquer and they all go out and accomplish.

Q: ​Well, I have seen you lean on them for things that you know that they are maybe more of an expert on, in a specific thing. But as a leader, you also are the one steering the ship and avoiding the icebergs while they may be down there like shoveling coal, and going wait a minute, it’s perfect down here, why are we changing course? You’re like, we need to make adjustments. 

A:​ Yeah, and I love that. I love them. If I could make a living on networking and just connecting the right people to the right projects, that would be my dream, I think I’d love it. I’m always out kinda meeting and interacting and paying attention to what all the other creative teams in town are up to. 

Q:​ So, Key West being a smaller town than it is, what do you do to kinda stay relevant and sharpen your craft and to do things to keep bringing innovation to the town? In your business? 

A:​ Good question. Well, you know Key West might be small, but it’s kinda like, everybody wants to come to Key West, and be in Key West, and visit here at some point. So, there’s a little bit of everything down here, there’s something that appeals to every walk of life, so you know, how do I stay relevant? I keep people around me that are more in-tune with it than me. 

Q: ​Smart. Smart.

A: ​I’m learning, I’m always learning and I like to laugh, I try to even in my communication style and in my emails, and on the phone I try and like, I want to be hip, and relevant, and I want to sound like that cool person that they want to hang out with and create this experience with, ya’ know? So, I learned from my team, too.

Q:​ And vendors, and sponsors, and all these other people, and it seems like you love, genuinely love being involved with learning what they are doing and talking to them. 

A:​ Yes.

Q:​ I mean, people are going to tell you what they want and if you’re a good listener, then you’re going to take that and make that work.

A:​ And, if I see somebody doing a great project, I mean there’s so many brilliant people in this town, so many wonderful creative people, like more people you should interview. You know, David Sloan, Marky Pierson and the Wonderdog team, and Liz Love, I mean there’s just so many brilliant creative people. I find ways to do projects with these folks and it works.

Q:​ Yeah, the thing about Key West is, you can’t, you can’t ever judge a book by its cover. At all. 

A:​ That is for sure.

Q:​ It’s incredible because it has a small-town feel, but a lot of worldly people. Cause I remember when I first came to visit, and I am in a restaurant, or I’m in a bar, and having a conversation with the bartender and she’s like, “Oh, I’m not going to be around next weekend because I’m going to Paris with my boyfriend.” And it’s like, a lot of traveling because sometimes the island fever, or whatever, just to get outta here. People save up and they spend their money on what’s important, which is, kinda traveling which is great. 

A:​ Yeah, seeing the world. All walks of life, all different cultures, and income levels, and they are all right here in this little 2×4 mile island. And, Miami is a long way away. We need something, and if we don’t have it here, we are really resourceful and creative and we figure it out. 

Q:​ And that’s the thing, you have to start thinking like, you know cause when we first moved here, it’s like, “Oh, Miami is down the road.” But then you’re like, well, it’s not, and there’s certain things that you can’t get here that you can get there. I’m like, “Where’s Whole Foods?” and it’s like can I get stuff shipped from there and you just can’t. So, then you just learn to live simpler on certain things. Right? It’s not like we don’t have running water and electricity here, but you are still, because there’s less choices of certain things, you get to use your capacity for things that are more important.

A:​ That’s a biggee. That’s a biggee in the success of my business.  We don’t have ten vendors that provide the same service. You know, to use DJs, or musicians, or florists, or all the elements and all of the different types of vendors that I work with to create these events? I don’t have 20 people competing for the same business, I have three or four and sometimes even less, that I have that confidence level in. They’re as much my clients as my clients, because I need to work with them.

Q:​ Right, because after the event, guess what? You see them at the sandwich shop down the road.

A:​ And they’re, and I rely on them for the success, and we build each other up, so you know, we help sell each other. We help each other succeed. 

Q:​ For sure.  I love that about the island. You can feel that community for sure. So, any recommendations for people looking to get into this business? Not down here, of course, we don’t want to give up those tips for competitors, but if they are going to a smaller town, or if they live in a small town, maybe up in New York, or New Jersey or wherever, and they want to get into this business. What do you recommend they do?

A:​ I say, I mean I think that I feel like I really did it right. I would say start small. Break it apart to the important elements and really learn. Work. Work as a caterer, work as a server, work on a boat, work in a hotel as a convention services person and learn how to work within that system. I mean, I spent almost nine-ten years working for a big hotel company and I learned every department. I paid attention to housekeeping, food and beverage, and the banquet service and how it was all interrelated. I worked with human resources even, and then they bought a guest house, and they needed a manager and I said, “Sure, I’ll do that!” Just be willing to learn every element, like everything that comes your way, there’s a reason why it’s coming your way. And it all is invaluable to me today. 

Q:​ And there you go folks, from running a business, to cleaning the toilets, she can do it all.

A:​ Yes, that too. Yeah, those glamorous wedding rehearsal dinners and then the bathroom overflows. I’m in there with the manager, this literally happened, we were fixing the toilet at a wedding rehearsal dinner and the buyout in the dining room.

Q:​ Holding the bridesmaid’s hair as she’s…

A:​ No, no, no.

Q:​ No, that’s somebody else’s.

A:​ That’s a different story.

Q:​ Okay, so the last business question and then we get into the juicy personal stuff, which are not that juicy, but they are fun. Name something that people don’t know about your business.

A:​ What don’t they know about my business? I think probably that we really could do anything. If they can imagine it, any kind of event, we do social events, parties, you know.

Q: ​So, let’s break that down for a second. So, if I’m a business and I come down here and I want to do, let’s say I have 100 employees and I want to do some kind of brainstorming growing business together.

A:​ Yeah, brainstorming, teambuilding, motivational stuff, or you want to launch a new product and do some guerilla marketing all around Key West. If you can dream it up, we can do it. We produce experiences and events, and it could be something as simple as a 50th Anniversary, or as complicated as a big corporate brainstorming think-tank where they are expecting a huge return on their investment and all of their employees to leave motivated and refreshed and full of great ideas.

Q:​ Nice.

A:​ We really are, you know, consulting for our clients and customizing an experience, a one-of-kind Key West experience. 

Q:​ Or, as giant as Fantasy Fest. Which we can’t stop, we can’t move onto personal until we talk about Fantasy Fest.

A:​ City-wide festivals, and yeah. Yes, as giant as that.

Q:​ So, tell me about, if you can, your first Fantasy Fest as a participant. The most radical thing you can say that your daughter won’t mind hearing.

A:​ My daughter, my mom. No, I’m really not that radical. I encourage the creative and crazy, the wild, but me – myself – I’m pretty tame. But I have made some amazing costumes over the years and participated and that’s what I love about it, the creative costumed participation. The locals and the visitors really make this event. So, Fantasy Fest has been going on – and we are celebrating our 40th year this year.

Q: ​It’s unbelievable.

A:​ The previous director was in place for 27 years, so this will only actually be my 3rd year as the Director of Fantasy Fest. I’ve had a lot of fun with it, you know, just having been here all this time, having it be my introduction to Key West. You know, I got here a week before it kicked off.

Q:​ Right? Imagine that 40 years later.

A:​ What the heck is going on in this crazy little island?  But I’ve seen it change a lot and I come from, well I have a degree in art and sociology, and so, people and creativity are my things. And it’s served me well, right? So, it’s just steering it back and getting the locals to embrace Fantasy Fest again, because really in Key West, if you don’t have the support of the locals you won’t succeed.

Q:​ Right. Which is why it started; the locals wanted to bring business to the island. 

A:​ They needed something to increase the, yeah bring people, bring tourism so that they could all make some money and sustain themselves through the off-season.

Q:​ And what’s your vision for the five-year vision from now where it’s going to be? 

A:​ Well, we are working really, really hard to appeal to the next generation of festival goers. So, we are paying close attention to other really successful festivals. Like Coachella, Burning Man, and we are learning from how they do things and how they market, and keeping it Key West and Fantasy Fest. Targeting, marketing, social media, technology, we are really trying to keep up with all of that and appeal to our festival goers. It’s also, you know people that have been coming for 30 – 40 years to this festival, so there’s also a very big part of this festival fan base that’s an older crowd, too. And they have to be able to afford Key West, and there’s a lot of elements that go into it.

Q:​ So, grandmother and granddaughter both partying at the same festival and both loving both parts of it.

A:​ Wouldn’t that be something? 

Q:​ Yeah, right?

A:​ It’s not easy to do, it’s really not easy at all. 

Q:​ No, so you’re keeping the tradition of Fantasy Fest strong, but you’re just adding the proven things that the younger generation enjoys, and that is working at these other festivals. I mean, that’s smart. 

A:​ Yes. Absolutely.

Q:​ But what I love about it, is that I’m not knocking anything being in the desert, or in these remote locations, because those experiences are fun, too. But, you’re on an island in a small city, and all this stuff is going on. So, like, there’s a lot of other things that are happening, besides setting up camp, food and beverage. You have to deal with the city, you have to deal with officials, and there’s still tourists, and there’s still people that aren’t here for Fantasy Fest, and you have to cater to all of that.

A:​ Right. Yup. Our year-round residents and visitors, yeah. We almost triple the population of Key West during Fantasy Fest, when you think about it. It’s pretty crazy, but the locals rely on these things. Key West is a great place for a festival, too. We have a few of them, almost every weekend, there’s something amazing, creative and fun to do in Key West. 

Q:​ And one other thing I did want to talk about, because I know you’re passionate about it, is the Key West Songwriters Festival, if you can tell me about that. 

A:​ Yeah, so you know, way back when I met Charlie Bauer.

Q:​ At the Hog’s Breath.

A:​ Yup, at the Hog’s Breath, right? And now he’s at the Smokin’ Tuna, and I have followed him along and we have worked together on this songwriters festival. He originated it with a guy named Drew Reed and a couple of songwriters and it is an amazingly awesome organic that has grown up from that, just from a couple of great performances. Key West embraced it and now it is one of the largest performing songwriters festivals in the world. And now we have over 200 performing songwriters that come to Key West.

Q:​ Wow, that’s incredible. 

A:​ Really, we have built it just like that. You know, we need accommodations to put up the writers, and so we worked with more hotel and accommodation partners, and we host a great show poolside, or on their beach, or we put songwriters out on the boats, and of course in all of the bar venues, we have an amazing historical intimate theaters here in Key West. Nothing is too big. Now Key West has evolved into such an amazing music destination.  

Q:​ Yeah, it really has.

A:​ We are lucky now to have the Key West Amphitheater that we can bring even bigger groups of people together to enjoy the same.

Q:​ I mean, I’m getting goose bumps because what I like about it is that, and because I love going to New Orleans a lot, and there’s a lot of that feel down here. Between the city and between the music and the food, but a lot of those musicians don’t just come to like, say you come to a Madison Square Garden and ten people are playing there and they play and they leave. This is like a lot of musicians come down here to also play, but also listen to other musicians.

A:​ Yes.

Q:​ So, you’ll go to a local bar and there’s somebody playing and 10 other musicians in the bar, drinking, having fun, listening, yeah.

A:​ So, they do the… as I understand it, they do more networking here in Key West sometimes than they do back home wherever they are from. At home they set up appointments to write with different people and get connected to different people and down here, you just never know who you are standing next to. We put them up in all these great guest houses and hotels, resorts, bed-and-breakfasts, and you know there’s a couple of different writers in each of these places and they run into each other poolside and get their guitars out and write hit songs. It’s magical.

Q:​ It’s incredible. 

A:​ This festival is really pretty magical.

Q:​ And the sights outside aren’t too bad either with the sunrise and sunset and the water and all that. 

A:​ I know it’s a fun place to be. It’s like an incentive trip for songwriters.

Q:​ It’s definitely artistic down here.

A:​ If they are selected and get to attend and participate, they have as much fun as the fans do. Everyone is so close, and you can talk to them after they step off stage, you can introduce yourself and they can, it’s great. 

Q:​ I think they expect that. So, in knowing that, they are like, “Well, I’m going to be talking to everybody anyway. I might as well go to dinner and have my own fun.” Which I love.

A: ​Yes, exactly. 

Q:​ All right good. The Business part is done. We can now get to the juicy personal questions. Although, they really aren’t that juicy, just trying to be fluffing it up here. Okay. What is your favorite event to attend, and I know we can already say Fantasy Fest and these other ones off the list, but…

A:​ Well, I’m working, I’m working. I’m forced to attend those because I’m working.

Q:​ How about one you’re not working?

A:​ You know, I had to think about this for a long time, but I think I’m going to say aside from my daughter’s dance rehearsal and her dance recital, I’m going to say that the Papio Kinetic parade is one of my favorite things to attend.

Q:​ And what’s that? I don’t even know what that is.

A:​ It happens in May right after the Songwriters Festival. It is awesome, I mean you could say obviously I like a parade, we have a little Fantasy Fest parade. This is all the local people making these kinetic sculptures so their human powered sculptures.  A lot of bicycles, wagons, walking groups, you know as the people are pedaling the bicycles the sculpture, they’ve created around them is doing things.

Q:​ Like, coming to life?

A:​ And it’s unbelievable. We have so many creative talented people in this town who put in so much time and energy and it shows. That is just, well it’s relatively new it’s a couple of years that it’s been going on, but it’s one of those things that the locals have embraced and it’s only gonna get better and better.

Q:​ So, it’s more locals than it is for out-of-towners? Or is it a mix?

A:​ You know what, that’s the great thing about it. I mean, obviously the locals are building these sculptures and they are creating these things for the parade, and then the spectators as these things go, they didn’t know it was happening and they see this coming down the street and they are like, “What? Holy cow this is so great!” And then they’ll make a plan to come back to Key West and see it again. And then, of course, a lot of those folks participate in Fantasy Fest too, which I love. But supporting the creativity, any kind of thing like that I love. 

Q:​ All right, favorite restaurant?

A: ​I think I’m gonna have to say Santiago’s because I have a five-year-old and I don’t get out much. So, date night, we really spend a lot of time thinking about date night. You cannot go wrong at Santiago’s, it’s my go-to when I get a night out. I absolutely love it.

Q:​ Favorite meal there?

A:​ Oh my gosh, really everything is great. But I would say to save room for dessert because the bread pudding is incredibly memorable.

Q:​ Nice. I may have to eat that bread pudding tonight. 

A:​ You’re going to.

Q:​ Okay, what about hidden local spot?

A:​ Well, since I have a five-year-old.

Q:​ Well, I have a ten-year-old, so work it for me, I’m ready.

A:​ I’m going to say Cozumel Park. This great little community park which is just a couple of blocks from my house out in New Town and it’s got a splash pad, green space, basketball hoop.

Q:​ Yeah, you told me about it and I was like, “I don’t even know where this is?” 

A:​ And it’s like two blocks away from your house. 

Q:​ I gotta go check this out.

A:​ And you know, if I go for a walk or a jog, I stop in there and it’s peaceful. There’s birds, big trees, it’s a nice little pocket park and the splash pad was a pretty recent addition and of course, Meredith loves that. 

Q:​ Cool. All right, best place for local music?

A:​ I get in trouble if I answer that one, right? I love the Smokin’ Tuna, I love the Green Parrot and probably most often I am at the Green Parrot enjoying the live music in there when I get out. You know, sound check and dinner at Santiago’s is date night dream.

Q:​ It’s like an anniversary!

A:​ Yes. 

Q:​ I love it. What about for happy hour? 

A:​ Here in my office on Caroline Street, I think my favorite happy hour is right across the street at the Half Shell Raw Bar. I sneak over there for some oysters.

Q:​ Yes, my neighbor, she works there and I always try to sneak over there during happy hour time. She’s like, “You gotta sit at the bar, it’s great. You get the happy hour.” 

A:​ It is, and the staff has been there forever, and they know ya’. 

Q:​ And the food is good, too.

A:​ It makes you feel like a local when the bartender knows ya’.

Q:​ Okay, tourist attraction that you take friends or out-of-towners? Who have never been here.

A:​ I’m going to say Blue Heaven. Everybody who comes to town and is visiting, no matter what, I try and get them out on the water. Something wonderful and in the backcountry, but for sure, Blue Heaven is my must-do. 

Q:​ Yeah, that key lime pie is like…

A:​ Breakfast, lunch, dinner, whatever it is, Blue Heaven is a must.

Q:​ Just don’t go there starving thinking you’re going to sit right away on a Saturday.

A:​ Well, you just get yourself a Bloody Mary and enjoy. There’s some olive, celery, lime. 

Q:​ Yeah, there’s a ping pong table behind it, just play a little ping pong, you’ll be fine.

A:​ You’re golden. And it’s worth the wait, and it goes fast, and it’s so good. 

Q:​ My favorite. Well see, those juicy personal questions, they weren’t that juicy. But we have to make the show exciting. 

A:​ That was, I handled it well. 

Q:​ Now, where can people find you? We’ve Got the Keys. If you have anything personal like Twitter or anything you’d like to say, now is the time. 

A:​ Sure. Well, it’s pretty much We’ve Got the Keys, across the board. http://www.wevegotthekeys.com/ and you can find us on Facebook https://www.facebook.com/wevegotthekeys/ and on Instagram https://www.instagram.com/wevegotthekeys/

Q:​ Perfect, and are you on social at all?

A:​ Me?

Q:​ Yes.

A:​ Yeah, but I’m way more fun in my business personality. 

Q:​ You can get to We’ve Got the Keys. You can get in touch with her.

A:​ Mostly you’ll see pictures of Meredith doing cute things on my own social media. 

Q:​ All right, and the last thing, I’m always going to ask the same question to everybody. The same one. Give us your tip of the day. Now it can be, something new you’re doing, a book you’re reading, a food you just ate, a favorite thing like I like weighted blankets, I mean it can be anything crazy, that right now you’re into. 

A: ​I haven’t tried a weighted blanket yet. 

Q:​ My wife’s got it, she loves it. Yeah.

A:​ Ah good to know. Right now, I am really into finding ways to make Fantasy Fest more sustainable and more green. I’m always looking to be more environmentally savvy and conscious and with this huge festival, bringing in all of these people to town, we consume a lot of plastics. So, there’s a lot of discussion about the throws from the parade floats, and how we can be more green in the street fair, so I have been scouring the internet and starting all kinds of social media conversations with suggestions. I think we’re coming up with some good ones.

Q:​ Is that trickling into your personal life, too? About green, and thinking more about, “Well, maybe I don’t need that red Solo cup, I can bring my own cup.” 

A:​ Yes! It always does and it’s fun having children. I know they spend a lot of time in school learning about the environment and gardening. I know they do at Meredith’s Montessori school, and so she’ll even call us out on it. We are good recyclers and try and be savvy about it.

Q:​ Yeah, and when you’re on a small island you can see the impact.

A:​ Hugely important. It really is. We work really, really hard to get that message out. 

Q:​ Well listen, this was a great first episode. You answered everything perfectly, you were like the perfect guest. I wanted to thank you again. Okay, no hyphen, Nadene Grossman Orr on the podcast.

A:​ No hyphen 😎

Q:​ That’s it, thank you very much.

A:​ Thank you for having me! It’s been super fun. Thank you.

Q:​ Okay, bye. 

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