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Episode 13: How Artist Anna Sweet is Making Waves in the Art Community

October 18, 2019

We are having a conversation between Mark Baratto and Anna Sweet. 

MARK:           My name is Mark Baratto. This is the Backyards of key West podcast and I am sitting here with Anna Sweet. Anna, welcome to the show. 

ANNA:           Thanks for having me.          

MARK:           You’re welcome. We are in, now you have two studios, right?

ANNA:           I have a studio and a gallery, yes. 

MARK:           We are in the studio and then the gallery is on Duval Street, right? 

ANNA:           Correct. 

MARK:           I need the origin story. The how did you get into this? Where did it come from? Obviously, you’re an artist so tell me about you as a little girl.

ANNA:           I grew up an art gallery. My mom is an artist but she raised us basically buying and selling antiques for, gosh ever since I was born. We lived in Charlotte, North Carolina in the upstairs of an antique gallery. That’s where me and my nine brothers and sisters were raised and my mom did that by buying and selling and making her own work and selling that as well. So, I was constantly surrounded by that growing up.

MARK:           And did you, was this, did you want to be an artist? Or, did you want to have a gallery, or be more on the business side of it? 

ANNA:           I guess, well I saw my mom and I saw her struggle and I saw her painting away hours on end and I knew that I wanted to be creative. I knew that I was creative. But I didn’t necessarily want to follow down her path and then look where I am now. It’s funny, but I decided to go into photography. I decided to study something that was a little bit more instant gratification. I picked up a camera at 13 – 14 and I obsessed. I would video everything, I would photograph my little sister, I’d photograph all my friends at school. Then I guess, I decided hey maybe I can make a career out of this? So, I started looking at art school options and that’s how I ended up in New York.

MARK:           Tell me why the camera? Was it?  

ANNA:           I think it was because I could never draw as well as I wanted to. I wanted to capture what I was seeing. I wanted to show the beauty of the world accurately and I didn’t feel like I had the skills to do that with a paint brush. 

MARK:           You knew that you wanted to get into art. You saw your mom doing it, you saw there was struggle in there, you’re like all right, I don’t know what direction I want to go in, but art is definitely the world that I want to be in. 

ANNA:           I was always moved by powerful imagery and with these classic paintings all around my house and just magazines that I would see growing up, I would feel an emotion when looking at certain imagery and I wanted to be able to evoke that same emotion out of people with my own vision. I think that’s where the camera came into play because I could literally see something how I saw it captured exactly how I see it and then display it as such. 

MARK:           When you were doing that, when you were younger were you like, this is a career path or were you thinking hobby? 

ANNA:           Oh no, I was obsessed, and I was like…

MARK:           You were like, this is it! I have to find a way.

ANNA:           I decided the dream job would be to do what I love and support a family at the same time. And, I think I just had that in my head and I never let it go.         

MARK:           I love that. What other things were you into that were outside of the art world? 

ANNA:           Well, I fenced for a while. My brother was a great athlete and he succeeded at every sport and there was nothing that he couldn’t beat me at, so I decided to start fencing just to throw him for a loop and it went well. I kind of excelled with that and went to national tournaments and kind of, I don’t know, I wanted to be like my brother, I guess. And, so I did that for a while but then ultimately came back mostly to the arts and like, I had a one-track-mind.     

MARK:           With all the brothers and sisters, where did you fall? 

ANNA:           Seven of nine.

MARK:           Wow, okay. They had a lot more experience in working with the children before they got to you. And the brother you’re talking about was he the one he looked up to the most, or? 

ANNA:           It’s actually my little brother, so I kind of joke and say we came in litters and there was like three, six, nine. I was the youngest litter, the third litter, and I was the oldest of that litter. So, it was me, my little brother and my little sister. My little brother was mama’s boy and he was the head of every team he was ever on and so I think, and part of trying to get attention from my mom, it was like, well maybe if I play a sport? I’ll get that attention.    

MARK:           You were the head of that pack, in a way.

ANNA:           Yes, the leader of the pack. 

MARK:           And, are you still competitive with your brother now? 

ANNA:           Oh my god.    

MARK:           Is he an artist? What does he do?

ANNA:           Well, he’s actually in life insurance and he also just opened a gym, but he helps me all the time. He’s my right hand when it comes to art shows. I just got back from Sausalito, the Art Festival in California and every time I do a show like that, I make sure he’s by my side. He gave me all the confidence I needed to be a business person in the art world, I think? My first show I sat in the corner and I didn’t talk to anybody and he just was my advocate and my pioneer and after seeing him talk about it so easily and answer questions, I just realized one thing, you just have to talk to people. You just have to engage, you have to ask questions, if you’re shy and you’re quiet and you let’s say you let someone walk by and decide that oh maybe I like that, maybe I’ll buy it or maybe I won’t, then you’re not going to get very far in this industry. So, he taught me a big lesson and it’s like, what do you have to be scared of? What are you worried about? People love your work, otherwise they’re not coming up to look at it. They are not coming in here to give you insults, they are coming in here to praise you, so he’s just like accept that and listen to what people have to say and it’s as easy as that. 

MARK:           Great advice. What about when you guys were competing against one another? Did he go easy on you? Or, did he not let you win purposely on a lot of things?

ANNA:           No, he’s good at heart you know? As competitive as we both are, I think at the end of the day we want to see each other succeed and be happy. I don’t think it ever got to be vicious or anything like that, but we definitely butt heads a lot because we are both very strong and we have our own way of seeing and doing things. It’s my business and it’s close to my heart, but he sees the business side of it and how it could be better. We are constantly playing that battle. 

MARK:           The reason I asked is because, having somebody that won’t sugar coat things and won’t let you win, to let you win, builds fortitude for real world. 

ANNA:           I agree.           

MARK:           Because that’s how it is. So, him battling you like that, and not going too easy on you, helps shape you. Just like, I have an 11-year old and I try to do the same things with him. I’m not letting him win everything, I’m making him have to work for certain things, because when he gets older and he goes out there, it’s how the world’s going to be. 

ANNA:           100%. Sometimes and I have a 2-year old and just for fun, she’ll ask for gummy bears, or a pouch the little fruit pouches, and she’ll ask for one every day. And I’m like, well I could easily say yes, but you don’t always get a yes in life. So, sometimes just, and not to be mean, but for the Hell of it, I say, “you know what? Not right now.” We are not going to have one of those just because you want it, doesn’t mean that you can have it, so I try to do the same thing. 

MARK:           It’s important to instill that because not so much my generation, but the generations below me a lot of things that are happening, and I guess even in my generation a lot of parenting is like, protective parenting. Like, oh no I don’t want my kid to get hurt at all. I don’t want them to lose at anything. You know, you failed at this but it’s okay! You did the best you did and it’s like, well you may have but you still failed and it’s important to understand that. 

ANNA:           I, 1,000% attribute where I’ve gotten so far in the world from growing up in a family that did not sugar coat things. With so many brothers and sisters, you were lucky to get a word in, or even a bite of food in, you had to really stand up for yourself. You had to be independent, you had to go get it, if you wanted it you had to get it. Otherwise you’d starve basically. 

MARK:           Yeah and your brothers and sisters all helped parent each other, too. So, you are parented as peers which is even harder and the lessons are stronger there because your brother is going to be like, I’m not your dad, go screw yourself, right? Whereas your dad maybe wouldn’t say that. 

ANNA:           Well, I don’t know. My dad wasn’t the nicest guy back in the day but he’s made a 180 since then, I think all the stress off of him has changed him as a person, but that’s a story for another day. But, if you ask my husband, he is the first person to say the one thing about Anna is that she doesn’t sugar coat things. So, I give it to you how it is and I just don’t see any constructive way of going about it other than that. I have learned from him as a very affluent business man that you have to go about it a certain way. You can still tell people exactly what you’re thinking, but people’s emotions are real, so you have to take that into consideration, and you always say what they are doing great before you tell them what they are doing wrong. That’s one thing that I’ve learned in owning the business and has been the hardest is managing employees and remembering to do that.             

MARK:           And these are the lessons that you learned from your husband? 

ANNA:           Yes, him a lot and then also having the business. 

MARK:           From doing. 

ANNA:           I lean on him a lot because he’s had a business for 20 years and he’s never fired an employee. He has had the same people the entire time and it’s like, well that’s definitely and when we get into that in Key West, we’ll talk about I’m sure about how difficult and that’s one of the biggest things, one of the biggest challenges for Key West. 

MARK:           Is that because he’s really good at hiring beforehand?

ANNA:           Gosh, I think he’s a good read of people, but I think he treats his employees with such respect and just and just a great guy. He doesn’t put up with things, but at the same time, he’s very patient and nurturing and I think that makes him a good father and a good boss.

MARK:           Excellent, and I’d ask more but only if he was here today. There’s a pillow here where he should be sitting. Tell me about the first job that you had, that was not in the art world and not fencing. 

ANNA:           Wow, my neighbor, because I lived in an art gallery, my neighbors was also commercial so it was a music store. They sold woodwind instruments, so flutes, trumpets and all kinds of stuff, and my mom was friends with the owner, so she convinced him to hire me, I was 14-15 years old, my first job. I would literally sit there and sort the little pads that would go into flutes, the keys of flutes, and I would have to count them out in sets of thirty and put them in little Ziplock’s and then label them. I did that for four hours every day and that’s actually how I discovered fencing because the guy I worked with was a fencer. We would talk and we had nothing else to do and he said, you know there’s a club right by here, you could probably go check it out. That’s how I ended up doing that. 

MARK:           And you were just like, okay fencing, I might as well. I can beat my brother at this one!

ANNA:           I thought it was really cool, something Joe Joe can’t do, so sure!

MARK:           That’s great. What about anything earlier than that? You were hustling to do because I’m assuming with that many brothers and sisters your parents weren’t like, “oh you want this? Sure. You want that? Sure.” 

ANNA:           Definitely. We struggled for sure, and money was just never handed out, it was always earned and for me, I saw how hard my mom worked to pay the bills and so I did so many things from, after the fundraiser was over continuing to sell candy at school. I would throw benefit concerts for a charity and say I would give all the ticket proceeds to the charity but then I would keep the food money for myself. Like I would sell pizza at that event, and that actually almost made more than the ticket sales. So, it was always like, okay how can I pay for my gas. How can I pay for my cell phone? How can I pay for this? And so, I had to get out there and do it. 

MARK:           It was like, I want this particular thing and, well even paying the gas or paying the bill, or the film.

ANNA:           Yeah, the film for my camera, yeah.         

MARK:           How can I do something to get that? It’s an important people need to realize that because the place where you’re at now sometimes think the overnight success and stuff like that.

ANNA:           Or, it was given to you in any way. People tell me every day they come in here and they say, man you’re young! I say, “I feel like I’ve worked the same amount of time as the person that is in their 50’s has worked because I just never stopped.” I don’t take days off, I don’t you know, when you have a baby that you are trying to nurture, literally two babies – a business and a child – you are just never off. I work constantly.    

MARK:           That’s the reason why I’m hung up and asking these origin story questions because it’s important for people to realize when it comes to running your business and when it comes to doing a business, things aren’t handed to you. It doesn’t matter how old you are, it matters when you started doing the thing you did that lead up to where you’re at (now). And you, at a 12-13-year-old, are hustling to pay for a cell phone bill. I mean, I didn’t have to do that. I did little things on the side like, when it would snow, I would shovel people’s driveway and I’d make money doing that. But it’s like, up until I was 18 and even went to college, my parents helped. That was in my eyes, a little bit of a detriment because I had to struggle more after college when my parents were like, well now it stops. And I was like, oh there was a little bit of a ride going on there for four years. 

ANNA:           Yeah, and how do you all of a sudden as an adult say, “Shit, now I gotta be an adult!” like overnight.      

MARK:           Luckily, I understood the situation and wanted to gear up especially having that 80’s – 90’s man mentality, I gotta work, I gotta take care of these things, right? So, that was my drive to be like cool, I don’t need anything from anybody else. But having that, I don’t get it unless I work for it mentality, that’s what I’m trying to instill in my kid now. Oh yeah, he’s got a couple of hundred dollars saved up and he wants to buy something for Fortnite or something like that, and he’s just like, “I’m going to use my money!” And I’m like, I can’t wait until you burn through all this money. 

ANNA:           Or, you can say, “what can we put that money into?”    

MARK:           That’s what I, trust me, being from that. 

ANNA:           Then you can afford all the Fortnite things. 

MARK:           He doesn’t get it and I tried to explain it. 

ANNA:           Let’s turn one Fortnite into many!

MARK:           I’m like well, if you just put it all in Facebook stock, just that or Amazon. 

ANNA:           They just got really bad press, now’s the time.    

MARK:           Yeah, I told you dude when it was at 80, we should have went in and now it’s 180. But yeah, I’m trying to teach him that, too. Especially coming from the background that I have with being in a market and stuff like that, make it multiply, or you want this? You have to earn it. Instead of earn it for a piggy bank, earn it for something that you can tangibly see. 

ANNA:           I think passion is so coupled with what we are talking about. You can understand the responsibility of something but if you don’t have passion and if you’re not passionate about it, it’s not sustainable. It’s not going to last. So, I think a huge influence or beneficial side of it is that you have to remember that, to be passionate.       

MARK:           Agreed, the thing that people struggle with, some people will say, “I don’t know what my passion is?” 

ANNA:           Oh, that’s so annoying. 

MARK:           How do I find that? A couple of things I tell people is, first you’re never too old. You could be 40 years old and you don’t know what your passion may be so you need to try things. What’s your favorite food? Oh, it’s this, well how did you know? Well you tried all these things. Have you ate oysters? No. Well, maybe that’s your favorite food. Time to taste. Taste a lot of things and it’s easier to do that when you’re younger. You have zero responsibility or less that you can taste a bunch of things. It’s almost like, what do you enjoy doing that if you “had all the money in the world” you would do. Why don’t you do that? So, sometimes it is judgment of others that’s keeping you from really doing what your real passion is. 

ANNA:           And a lack of self-confidence, unfortunately for a lot of people. They might enjoy something but they don’t think they are good at it. Or, not good enough at it. They need someone to tell them that you should do that. You’re good at that. Why don’t you? Maybe they didn’t have parents that said, “you know, man that’s good.” Maybe you should try that out so I’m all about inspiring people as much as I can. A lot of my employees are young and up and coming artists and I find myself spending half my time trying to nurture their career rather than having them help nurture mine.      

MARK:           That’s the thing, they can and never will work as hard as you. The reason why is because this is your business. 

ANNA:           That’s a lesson I’ve had to learn, yes.        

MARK:           That’s a lesson that for the people out there listening, if you own a business and you complain that, “why aren’t my employees working as hard as I am for the same dream?” It’s like, well give them as much equity as you have and then you’ll see a difference. It doesn’t work that way. They are never going to work as hard as you. It’s important to realize that you’re the one in charge, meaning anything that breaks, any employee that steals, any problem they have, you hired them so you have to take responsibility for that and learn about them. How many times have you taken your employees out to dinner? How many times have you seen where they are at, at that particular time in their life? Maybe right now they are single, maybe in five years they are married. Maybe in five more they have kids. Maybe at the beginning they wanted more money, maybe now they want more Work/Life balance. Who knows? You have to understand your employees in order to direct them in the right way. Then you’ll have long lasting employees which obviously your husband knows how to do really well if he still has all his employees. 

ANNA:           I think it’s building those relationships and gaining that respect from your employees and I think a big way in doing that is showing that you care. I think that’s the #1 complaint for a lot of employees is that they feel underappreciated. The more you can show your employees that you appreciate them, the more they know that they are doing a good job, you have to show people constantly that they’re being appreciated and they will continue to be inspired.  

MARK:           Tell me, when did you first come to Key West? 

ANNA:           Oh man, that’s a fun story. I was engaged once upon a time, we all had tickets to go on the bachelorette party and it was in the Caribbean and I for many reasons had to call the wedding off. And, we decided to have an unbachelorette. Now that we all had the tickets to Miami connecting through, I decided why don’t we just drive to Key West. So, we all came here on an unbachelorette party, which was way more fun than a bachelorette party! 

MARK:           Oh, I bet. Was this your first time here? 

ANNA:           Yes.     

MARK:           And, you didn’t just stay? You came and partied and had fun and then went home and then? Then when did you come back? 

ANNA:           Correct. Then I realized, oh my gosh it’s such a cute town. My parents were living in Miami at the time. My mom was doing her art and we both decided, “hey maybe we’ll go down and find a gallery to represent us in Key West.” I did, and ended up being represented at the James Coleman Gallery and this must have been like 6-7 years ago, when I first came out with my first line of work. I literally went door-to-door at every gallery and I had it in my hand, my work, and…

MARK:           You had a brochure of it? 

ANNA:           A brochure, my book, but then I also had my pieces in the car. As soon as I showed them my book and my brother actually helped me put together a little sales pitch as you could say for galleries which showed my numbers. I had one gallery in Ft. Lauderdale at the time and they were doing pretty well with my work, so he said, “hey just take these numbers into… and everyone’s a business person, and show them what you’re doing and show them the work.” That’s what I did. I said here’s my book, here’s my sales over the last year, and then immediately he said “sure, bring it in let’s look at it.” It fit the bill and his name is Bill – no pun intended – but yeah, he decided to carry it right there on the spot. So, I was in there for about five years and when I was in Hawaii two years ago, right before we moved here…      

MARK:           You were living in Hawaii? 

ANNA:           I was living in Hawaii and I, well I know we are backtracking a little bit and hopping around…  

MARK:           Well, we’re going to go all over the place. 

ANNA:           Okay good, so basically five years there and then decided to make a transition and do my own thing. They were my best-selling gallery so I thought, well we know Key West, let’s do it there. Let’s open a gallery in Key West.    

MARK:           I’ve got a lot of questions. Let’s go back to when you were a photographer and thinking, okay this is the business I’m going to get into. When did you start believing in yourself and picking up the paint brush and going in that direction? 

ANNA:           Gosh, it’s funny I was just thinking the other day as I was painting one of my pieces and I’m like, I never thought in a million years that I’d be painting. I wanted to be a fashion photographer and I wanted to shoot for Vogue, I wanted to shoot for Vanity Fair, I interned for one of the world’s biggest fashion photographers in London, Rankin. I was there for three weeks and realized, man I don’t know if this is for me. I mean, the guy barely did anything. He’d walk in and wouldn’t even hold his camera and I probably shouldn’t say this on the air but…

MARK:           I don’t think he’s going to be listening. 

ANNA:           Okay good. 

MARK:           We’re not that big yet.

ANNA:           All of his interns did every single and last thing for him. 

MARK:           What did he, just push the button? 

ANNA:           He literally, his intern held the camera over his head, and followed him around set and he would push the button. So, I just got turned off at that point and decided, well maybe I need to go more into the art world. My mom you know being an artist my whole life, I was familiar with that, so and I saw it as more instant way to pay the bills. It’s really hard to fight your way through the industry in New York, as you know, to get any kind of paid job you’re going to be working for free for ten years before you get any kind of job. So, I needed to pay the bills then and there, so I decided to approach an art gallery for the first time with my photography. They said, “wow that’s beautiful, but we don’t sell photography.” 

MARK:           You approached a gallery for the photography work. 

ANNA:           Correct. 

MARK:           I see, yeah because I’m like, trying to make it as a photographer in New York City is you know, being a painter in New York City is just as hard or even worse. 

ANNA:           So yeah, I started with photography, I studied photography as the School of Visual Arts in Manhattan and that’s how I ended up in New York and then working for several photographers in New York, eventually moving to London to work for Rankin, and then I didn’t start painting until two years ago. My whole, well my photography actually encompasses a lot of abstract painting, merged with it and this is one of my underwater photographs over here. But that work evolved because that first gallery told me, “no, we don’t sell photographs.” So, I said “cool, let me make something you can sell.” I decided to, and I had been to so many different art shows and museums that I saw work with mixed media and texture and I decided maybe I’ll add that into my photography and that’s exactly what I did. I thought this is kinda crazy and this is not what I’d ever thought I’d be doing, I thought I’d be shooting fashion and so I just went crazy on the canvas, you could say. Through materials and paint, and just tried to make it something truly one of a kind and unique, so that the gallery could say, we’ve never seen this before. Let’s, sure, and that’s how I got my first gallery. I went back six months later with these five pieces that I had added paintings and texture and …

MARK:           Were these photos that you printed on canvas and then painted? 

ANNA:           They were all underwater photographs, but then I wanted them to be very sleek and at the time metal was just kind of, well metal printing was just coming about, so I actually the first line I printed myself at Costco because it was the cheapest place to print. I glued it to plexiglass that I got from a guy in Ft. Lauderdale, and I put wood from Home Depot and I cut it up and used wood glue on the back, it was totally botched together. I took it to the gallery, they loved it and wanted to give it a shot, they had a show for me and all the pieces sold out in the show and then I quickly realized that I had to replace them all because…

MARK:           Well, tell me that moment, did you see them all sell out? Or, did you get a phone call? I want to know that moment. 

ANNA:           I was at the show when they started to sell and as soon as one piece sold – at the time I think was $3,600 – I mean…

MARK:           How did you price them? Did they price them for you? 

ANNA:           This is funny, too because they asked me, “well what do you think you want for them?” So, I just took my cost and I tripled it as my mom has always said, “you triple your costs.” I said, that’s what I want. I want, I don’t know, I want $1,200 or the price should be $1,200, and in my mind, I wasn’t thinking the gallery’s going to add 40, 50, 60% on top of that. 

MARK:           Right, you’re thinking the customer would pay $1,200.

ANNA:           Yes. Okay, so if the customer pays $1,200 and it’s like a 50/50 split, then I get my cost plus a little blah blah blah, so I’m like oh okay. Then great, they’re like $3,800. And I’m like, oh, you really think people are going to pay $3,800? 

MARK:           You tell them $1,200 and they are thinking cool, that’s what we’ll pay for them meaning the gallery.

ANNA:           Yes. 

MARK:           And then, you get anything from, like you get the $1,200 and they get everything above that? 

ANNA:           How they work and every gallery has its own way of doing it, but they are a 60/40 split. So, they take 60% and the artist gets 40%.  Okay, so if we price it at $3,800, you’re getting and I can’t remember what, it’s like 1,500 something. And I’m like, holy crap! I just didn’t realize, oh my God my work could actually sell for that much and when it did at that show. 

MARK:           Yeah, you should have told them $5,000!

ANNA:           I still just didn’t believe them. Like, no one is going to pay that. That’s crazy and no one is going to pay that. 

MARK:           But when you painted and I’m sorry I keep interrupting, but it’s so juicy, when you went crazy the first time and it’s your first time doing this and you’re looking at all these pieces, are you like, wow they are awesome? Or, did you have confidence in what you did? 

ANNA:           Both, it was like, oh my God that’s so different. But who’s going to buy that? I don’t know, I didn’t … it had never been done before, I guess? It didn’t look like anything I had ever seen before so I just didn’t know how people were going to react?

MARK:           Did you call some friends and be like, hey do you like this?

ANNA:           Oh, all the time. I would send pictures and I still have a panel. Every piece that I produced to this day, I send to about five people and say, what’s your honest feedback on this piece and every one of them comes back at me with a different opinion and it’s great. That’s how I really just like hone in. 

MARK:           Do any of them come back and say, “no, I don’t like this.” 

ANNA:           Yeah. 

MARK:           Good. So, then you have the right panel. Because if they were all like this is great! You’re like…

ANNA:           But you know what? It’s great but you have a lot of stuff already like that, or I don’t really like the expression in that one, and 

MARK:           That’s fine, we had to take a pause because there was this massive – was it art coming in? 

ANNA:           It was actually a commissioned piece that just came in on a giant freight crate so…

MARK:           Yeah, it was this enormous piece. 

ANNA:           And you can hear the truck leaving now. 

MARK:           If they were not careful it could have been catastrophic in here. I don’t want to take responsibility for that. But it was good, because I was able to get a little bit of a tour on everything that you’re doing. Well, not everything, but a couple of pieces like that and we are going to keep that beeping in the background, I love that. I looked on your website and I saw some of the stuff you’re doing, but I don’t like to do any research. I don’t like to know anything about you, or anything, I didn’t know if you were married, I don’t know where you were from. I knew nothing because, why am I asking the questions then? If I already know everything. 

ANNA:           It needs to be natural. Organic. 

MARK:           It’s nice to know all those different things, so when it comes to your art and when it comes to designing and when it comes to pricing it out, you were mentioning that you were in the studio and they are like, oh we are going to put it at this price and then you’re like, oh my God, is anybody going to buy it at this price? And then you’re at, so it was like a gallery showing where it was just you they were showing? 

ANNA:           It was new and emerging artists that the gallery was promoting at that month and so I think it was me and three or four other artists all coming together to do a show for the first time. 

MARK:           Right and so you saw people gravitating to your work and then, did they buy it on the spot? How did that go? 

ANNA:           Yeah, they are really good at that gallery. They have great salespeople and me being there and my first show, being something new and exciting, I think that really spoke to people and it was I guess the right kind of magic to happen for them to write that big of a check. 

MARK:           Was mom there for this? 

ANNA:           Oh yes. 

MARK:           She was like, was she beaming too seeing this stuff getting sold. And you’re like, okay you gotta tell me, it’s the end of the night and you’re looking around and it’s sold on all your pieces, are you like holy shit. Was there a pinch me moment? Tell me about that. 

ANNA:           When I took that first check to the bank and I was sitting at the ATM and I had never even seen a check for that much in my whole life, I was just like, okay now I’m going to go make more art. That’s all I wanted to do. 

MARK:           Was it believable until you saw it like in the bank account. 

ANNA:           Correct, I never count on anything until it’s in the bank. 

MARK:           You’re like, they could say no and not pay. 

ANNA:           Or, decide it was literally and I had put those together with wood, glue and plastic so I was like, maybe they are going to return this and it’s going to fall apart but luckily those checks allowed me to remake them properly for all those clients I literally just put together what I could afford to put together. It wasn’t archival, it wasn’t something to sustain time, so luckily, they did sell and I could use that money to make them how I make them now which is on aluminum and proper resin. 

MARK:           So, they bought them and then you’re like, hey give me a month before I deliver them to you kind of a thing?            

ANNA:           They took them, and then I just slowly replaced them for each client. Yeah, I’m like you know, you …

MARK:           Wow, and how did that phone call go where you’re like uh? 

ANNA:           Well, they were like you know, and I mean they get it, it was my first show, my first producing anything like that and they were just happy to have it and happy for me to remake it properly. 

MARK:           I would have been ecstatic. You could have been like, hey you buy what you get, it’s a first timer, you bought it and if the thing falls apart, there’s wood glue coming out, but that was wonderful that you actually did that. 

ANNA:           I think that’s something that I’ve had to take with me through owning this business is that there’s always going to be that client whether it’s your fault or not, that you have to appease. You have to swallow your pride and say I’m a businessperson and this is part of the price of doing business that you have to make people happy. So, even if it’s a crazy request, like I get crazy requests. 

MARK:           Craziest request, tell me. 

ANNA:           Gosh, well…

MARK:           You don’t have to name names, and it could be someone not in Key West. 

ANNA:           Well, one thing popped into my mind the other week. I’m selling these little coasters now and they have my sticker on the bottom and this woman, and it was so sweet of her, but she emailed me a self-addressed envelope, requesting one sticker because one of the coasters didn’t have a sticker. And, so I just had to put a sticker in the envelope and put it in the mail for her, but she had to have stickers on all of the pieces. That’s what I did. 

MARK:           Is it like the barcode scanning sticker? Or what sticker? 

ANNA:           No, just like, it just has my name on it. 

MARK:           Well, she wanted, I guess…. the authenticity of you. 

ANNA:           Well, it’s like a $10 coaster and she wanted the sticker on the bottom. I don’t know, it was sweet and she was really nice. 

MARK:           She sells it for $15, it was a day in her life. 

ANNA:           Exactly. Maybe she’s like, this is not a complete set and I cannot sell this on eBay. That and then people asking for certificates of authenticity on things that are like $100. I know that sounds like, I don’t know, if you don’t know art, it’s something they want to prove it too. Well, my signatures on there. Like, what else, what other proof do you need? People get hung up on these certificates sometimes and I don’t understand it, but I’ll do it. 

MARK:           Yeah, I bought a couple of original pieces in Miami that reminded me of stuff when I left and I didn’t ask for it, but they obviously gave and that was the whole thing like, all right, I’m going to tell you this story. My wife bought me this piece of art that she hates that she bought it, but she loves it and I love it, is it when I was and I went to University of Miami and when I was in Miami all the time and South Beach and stuff like that, on one of those side roads Española, there was this artist that always and I remember in college always seeing this, it was Miss Piggy with like her boob hanging out. 

ANNA:           Nice. It was a painting? 

MARK:           And it was, yeah, a painting. Different Miss Piggy’s portraying different famous people but always a boob, like always her dress strap popped off and it was like, all original stuff that this guy did. It was like, I want one of these Miss Piggy’s because it will always remind me of Miami and then right before we left for my birthday my wife had one commissioned for me. And we have it in the house and she’s like, all right listen, we cannot have this in the living room, Miss Piggy with her tit out, we have to put it in a more obscure spot. Now it’s like every time I come out of the bathroom, there’s Miss Piggy right there. She doesn’t have full glory, but she’s got enough.

ANNA:           That’s nice. 

MARK:           Yeah, I understand what the certificate is and people want that because if you’re going to be a collector, you want to have that for in the future if you sell it? Is that a necessity?

ANNA:           No, it’s good. If it’s an original work of art and it’s a $5,000 thing that you need to have on your insurance policy and all this stuff, I get it. But sometimes when it’s just a print of mine, you know and it’s like…

MARK:           Not an original. 

ANNA:           Yeah, like it’s a $200 print and you know, it’s digitally signed and numbered and it’s something that I guess, and I’m always happy to make clients happy I’ll put it that way. 

MARK:           Yeah, of course. 

ANNA:           I’ll do anything to make a client happy. Just reading my emails today, I have a client that ordered a print and it’s a canvas print and one of the artist’s that I represent and it’s just wrapped around, on the canvas. But she doesn’t want it wrapped around on the canvas. So, now we’ve got to reprint the print to just be on the front. That’s how she wants it, so we are gonna do it. 

MARK:           That’s the reason why we may be harping and talking about these things and it’s important if you’re running a business, starting a business, is that you value your client your customer. 

ANNA:           Absolutely. 

MARK:           If you don’t.

ANNA:           They are your lifeline. 

MARK:           Then that’s it and that’s like when I talk to people about social media and stuff like that, it’s like listen, if you’re posting stuff and this is trivial compared to all of this but if you’re posting stuff and people are commenting and they are writing about the things that you posted that you like, you you’re complaining about why you don’t have more followers or all these different things, then why don’t you nurture the ones you have. Why don’t you be in communication with them. Why don’t you do the things with them that will show you that you appreciate them as a fan of whatever you’re doing.

ANNA:           Absolutely. That’s one of the things that I’ve had to learn being the scatter brain that I am, I always want to go to more, next, what else and then I realize… wait a minute, I need to focus on what’s right here and I need to develop what I’ve already started and I need to finish what I’ve started in a way. I’ve got so much traction already, and like you said, I’ve already got people engaging, why don’t I just engage with those people? Then more will follow, so I totally agree. 

MARK:           And the people that have purchased from you, are you getting reorders and buying more pieces? 

ANNA:           Yeah, surprisingly I mean, I guess there’s a lot of fans out there that have houses full of women. Today, it still blows my mind that people, and I shouldn’t be so insecure about my work, but it’s I don’t know, it’s something that to this day that people don’t really have it really decorated with photography of women. Literally it’s like, for centuries yes, paintings of women no problem. But when it’s something so literal, I still think it’s something so new and maybe that’s what makes the work successful is that it’s different and exciting and new. 

MARK:           I don’t find it surprising that they are rebuying because of the way that treat them. All of the things that you’ve said, those little things matter. You just never know and you want to do right just for doing right with no intention.

ANNA:           Every Christmas I try to think of something different and unique to send out to my clients to make them feel special and thought of, and all year long they’ll come back to me and say, “oh you know Anna, I got that coaster or that tree ornament in the mail, and it just made me feel so special thank you so much for thinking of me.” It’s just this little thing that I want to do to let them know how much I appreciate them because without them I wouldn’t be here. I’m always thinking of ways to let them know, thank you. You know? 

MARK:           And in a non-creepy way. You can get their social media and you can stalk them and see some other things that they like and they are like, I like this Merlot and you can send them a bottle of that with your signature on it or whatever. 

ANNA:           All the time. It was a woman’s birthday the other week and she really wanted this wave and I’m not bragging about this; I’m just saying because we are talking about it and she couldn’t afford it and so I said, you know what mom? My mom directs the gallery for me, she head of sales and so, I said “mom just let her have it for her budget.” And she was just over the moon, “oh my God you made my birthday, thank you so much.” When I was packing her wave up, I went ahead and threw like all these extra little things in there for her, like little surprises. I was just and I couldn’t wait to like hear her expression when she opens that package and finds something more than she was expecting already, you know? So, I do like to just, life is short and the more smiles I can put on people’s faces, the better. 

MARK:           Also, I can tell just from talking to you that you’re not high on your own supply at all. Which is important, right? You’re still pinching yourself. You are selling stuff for $4-5,000 or maybe more, and I see you still pinching yourself.

ANNA:           I think owning the business has really knocked me on my ….

MARK:           Ass, you can say that. 

ANNA:           It’s been such a wake-up call and very humbling, super humbling. I thought when I was 21 in New York City that I could anything and I love that I thought that because it’s made me do those things and it’s gotten me to where I am, but over the last year with my business on Duval Street and opening the studio and providing to the 20 galleries that I provide to and hiring multiple employees and having to worry about paying my rent. It’s made me see how hard and it’s a lot harder than I could ever have imagined. 

MARK:           Why did you go from artist to artist owner? Of a studio and stuff.

ANNA:           I think it was just one of those bucket list things that I wanted to prove that I could do. I’m always looking for a new challenge and I’m like, oh a gallery sounds like a great idea and if so-and-so is selling my work and taking 60%, I’ll open my own gallery and I’ll take 100%. But what I didn’t realize is it really comes down to being ultra-involved in your business. You could not put that business in anybody else’s hands and I just didn’t really at the beginning have the time to do everything. I couldn’t produce for my galleries and sell every day at my gallery, it’s a 12-hour shift on Duval Street. 

MARK:           And create the art.

ANNA:           Exactly, so producing and then selling and I couldn’t do both. Luckily my mom stepped in and took over the gallery director position and she’s been doing it her whole life. She went back to selling art and she’s great at it and she has really helped the gallery sustain over the last two years and thank god I have her. 

MARK:           You sell out this first run, and you’re like I gotta make more art and then are you now looking for different studios to place your art in? How did that go? 

ANNA:           I’ve been with my line of women, I’ve been carried in galleries for the last six or seven years since Key West and Ft. Lauderdale, Hawaii, New Orleans. I’ve had shows kinda all over in London, New York and different pop-up things here and there but over the past 2-3 years I started to want to expand my portfolio and have things as a business owner that has to pay rent on Duval Street you quickly realize if you only appeal to one person or one type of person, why limit yourself? So, it forced me to go outside my comfort zone and develop something that would appeal to Key West. 

MARK:           That’s before you opened the gallery, or as…

ANNA:           This is after. Once I opened, and sorry I’m jumping all around. Once I opened the gallery, I quickly realized that I couldn’t pay rent off of just my women, it was such a nice market. 

MARK:           The gallery had all women in here and you’re just like, ok. 

ANNA:           Yes, and everyone is telling me how to, and I had a salesperson that was helping me in the beginning had worked here in Key West for a long time, and she was like “Anna, you’ve gotta appeal to every single person that walks in the door.” And I’m like, I just don’t know, this is my name, this is my brand, this is my identity, I was so stubborn. Then my brother calls me one day and he’s very persistent and he’s a great salesperson because of it, but he said “you’ve got to carry this artist. I went to school with him, he paints with his fingers, he’s incredible and you won’t believe it.”

MARK:           Not to interrupt, but did you think that you were going to carry other people’s art? 

ANNA:           No. Absolutely not. 

MARK:           It’s me and that’s it. 

ANNA:           Correct. My name, my brand, I wanted to go big or go home. And so…

MARK:           And you’ve got the name for it. I mean come on. 

ANNA:           Yeah, I’ve been told that my whole life. So, I just had to run with it and I had to try. I did that and I think I quickly realized as a businessperson without an ego, an artists’ ego, I want to pay my rent and do what I love and I want to afford to stay. 

MARK:           You were paying all the bills anyway.

ANNA:           We were making by.

MARK:           But you were focused on, all right forget about my commission work and all that other stuff, I want to focus on this studio and how I can grow this studio. Is that what you were thinking? 

ANNA:           Well, with the gallery?

MARK:           Yes, I’m sorry the gallery. 

ANNA:           Yeah, so I dropped everything else and was just bleeding into the gallery. I had to be there every day, I had to oversee everything, I had to constantly figure out new ways to market, promote parties, openings, and I was working so hard and I realized well, maybe I should just try something different. 

MARK:           Your brothers like, I got this finger-painting guy. 

ANNA:           So, I’m like all right Joe, fine, I’ll do a show for him. It’s fine and we did a show and he sold out the first night. 

MARK:           Right, and you’re full circle. 

ANNA:           I guess this is God telling me that I just need to be more open minded and evolve. I did and now I represent 5 or 6 emerging artists at my gallery on Duval Street and everyone is so different that literally almost every person who walks in the door can find something that they connect and relate to, so I think from a business side, I had to really reach deep and put my artist ego to understand if this is going to be sustainable, I’ve got to give Key West what it wants. 

MARK:           Are you, yourself painting art and doing things more for what Key West wants? Or, are you still sticking with your type of brand and bringing other artists? 

ANNA:           Key West has had a huge influence on what I produce. I interact with my customers every day because my studio is 4,000 square feet here on Southard across from the Green Parrot and people can literally walk in every day and tell me what they do and don’t like about my work. I think that’s so valuable for me being that I’m in the retail side of things and I’m trying to sell. 

MARK:           That’s so hard to hear, but so smart.

ANNA:           It’s great, I can take that feedback and say, “you know what? I’ll make that for you, no problem.” And let me try, that sounds exciting, I’ll try something new and my art has changed a lot to appeal to the local demographic, which is funny because when I take my work and I have several galleries that represent it and the galleries in California sell completely different than the galleries in Miami. I’m learning, okay this is the style there, this is the style here and this is what people want here. Luckily Key West is a huge melting pot and you get people from all over the world that come here, so I don’t really have an issue. There’s something for everyone here. 

MARK:           Is that where waves, that art…

ANNA:           Waves, yeah, I’ve been doing the women and like I said…

MARK:           It was water from the beginning. 

ANNA:           Yes, all about water and I wanted to make a surfboard with something on it. I wanted to, I just wanted to make a surfboard and I don’t know why I was obsessed with the thought and I’ve been reaching out to people for a long time and doing so much research, going on Instagram and anywhere I could to find inspiring images of what I wanted to produce. I came across paintings of waves and I thought, “wow, that ties really well into my work and it’s not figurative, so it will be easier to decorate with for people” and I decided to try to paint a wave. 

MARK:           Which is like clouds, it’s so difficult. 

ANNA:           Yes! But I had been working with resin for so long that I thought, well I can just try to use the resin because it’s already like water and I started to develop this and it just, and I’ve developed a process that is incredibly unique and one of a kind and people see it and they think it’s a photograph. Every day people say, “what camera did you shoot that with?” 

MARK:           Yeah, I did too. Because I see a lot of your work as photography work and so I thought, oh you took a picture of that. 

ANNA:           I think I hit on something and God blessed me once again with something that has paid my rent since I started selling them. 

MARK:           How many did you do right away? 

ANNA:           I had a little tiny studio across from Fausto’s, like 250 square feet and I was producing as many as I could out of that space, experimenting, and in the beginning, I was like. 

MARK:           And that was private, right? 

ANNA:           No, the public came in. I was just like, man these are hideous, but I’m getting there. But every time I made a hideous one, someone would come in and say, “god that’s beautiful.” 

MARK:           How many “hideous” (said with air quotes?) 

ANNA:           With me, I’m a perfectionist and to me, I’m not seeing it the way they might be seeing it in an abstract way, but I’d say it was 6 months of developing the process where each one got better in my mind, but every person that walked in it was a gem to them. 

MARK:           So, listen everybody, that’s 6 months of failure, her failure, not from an outsider’s perspective but for the creator, 6 months of failure before getting to where you needed to do. Not like, this stinks, I’m done, I’m going to move onto the next thing.

ANNA:           What was important during that time was understanding that just because I think it’s a failure, doesn’t mean the world does. 

MARK:           Of course. 

ANNA:           I think we talked about that earlier in the episode, it was, you have to have confidence in yourself and a lot of people don’t think that their work is good enough. That’s what I was thinking right then and there in my studio and I’m like, I’m not going to put this on the wall for sale, but someone would come in and see me making it and they would be like, “wow can I buy that?” 

MARK:           Little blips of people saying, and you’re like… this stinks, and they are like… this is beautiful. And you’re like… I’m onto something. 

ANNA:           Yeah, maybe it doesn’t stink. Yeah, so. 

MARK:           Like a little gas on the fire to keep it going. 

ANNA:           Totally, and then I couldn’t keep them on the walls, I couldn’t keep them out there at all. I made the transition to an apartment because Key West rents are so high for commercial, and I was like I’m just going to rent a two-bedroom apartment and make ‘em out of there. So, I did that for a year and then I stalked this place on Southard, and I would go eat at Charlie Mac’s with my husband and there would be paper on the windows and I’m just like, what are they doing with this big building? So, I contacted my realtor and I’m like, can you find out who owns this building? I really want to make it my studio and it’s huge and it’s all the space I need. I’ll make it pretty for them, I promise. So, she reached out and initially it was no sorry, hurricane damage, we need to fix the building. 

MARK:           That’s because they are putting glue to keep it standing. 

ANNA:           Yeah, this building, well new owners and he wanted to do it right. Joe Walsh owns the brewery and a lot of things in town, Caroline’s, Jack Flats and all that, but he finally agreed to meet me and once he met me and realized that I just wanted to bring this place back to life, he gave me the opportunity and I am so blessed with this space. It’s really allowed me the space I need to produce, and grow, and it is great retail exposure, it’s right on the way to Truman Annex so if people walk by every day.

MARK:           It’s right on Duval, pretty much. 

ANNA:           And it’s a block from my gallery. I couldn’t have asked for better. Like I said, I wanted to buy this building at one point because it’s so perfect, so I got really lucky with this space and it’s allowed me to develop into where I am now which is producing at a pretty big level. I’ve got galleries on every island of Hawaii and West Coast to East Coast to Martha’s Vineyard to the Hamptons to Miami to New Orleans, all over. So, it’s definitely a dream and something I will tell anyone that wants to build their career in the art world you have to just ask for it. You’re not going to get anything in life unless you ask for it. Literally, I’ve cold called and it’s the most uncomfortable five minutes of my life, but I will cold call a gallery and I will say “hey, did you get my email. I sent you an email and I want to mail you a piece of work and I want you to see it in person.” (if I can’t go there myself) You just have to get there and ask for it. I think that’s what has helped me. 

MARK:           Ask for it a number of times. Not just one time. 

ANNA:           Yeah, and not just one time because I’ve had galleries ignore, ignore, and then I’ll follow up and follow up and it’s maybe on the third or fourth time when they say, “You know what? I’m so glad you were persistent about this because we do love it. It is doing well, or whatever.” 

MARK:           It’s funny because 80% of yes’ come on the 5th ask. Serious, it’s crazy. It’s like being in sales and it’s so funny how the majority of the yes’ come after all those no’s. That’s like the secret, of doing that, right? 

ANNA:           Persistence. 

MARK:           Everybody could do it, but then everyone would be doing it. It’s not easy. 

ANNA:           You just have to remember that just because someone said no the first time, doesn’t mean they always will and I read a really good book recently called the Third Door, and it’s all about there’s the front door, there’s the back door, and then there’s the third door. You either go in the front door, because you know that person or you don’t know that person but you have a connection. You go through the back door because you know that person. Or, there’s the third way to get in. So, it’s a guy that interviews and you might want to check it out, he interviews the world’s most successful people. That’s his goal for this book and he’s a college kid that drops out of medical school and decides to write this book. It’s all about him getting to these people no matter what. 

MARK:           I love it. 

ANNA:           He uses this third door to get to them and he’s persistent and just wants to find out what makes them tick and how they got to be successful. But it’s a pretty good book. 

MARK:           Wow, I’m definitely going to do that and if you’re listening you should get that book, too. We are not getting royalties, so don’t worry. I know we are going long, but you mentioned Hawaii. 

ANNA:           You can edit this later, it’s fine. 

MARK:           Your successful selling the work and what location was that? Was that in New York? 

ANNA:           I was in New York, hadn’t started producing when I lived there, but my art and I was just doing photography. But when I was living in London, I developed that first line of work and I got it. 

MARK:           Okay, so London is where you sold your first pieces. 

ANNA:           I did an art show on the street in London, that’s where I first tired the concept and I sold one piece and it stunk so bad of polyurethane polyester, what was it? Polyester resin that I had to go take it out, the first piece I ever made with resin and you couldn’t buy resin back then, it wasn’t something that artists used at all. I went to an auto shop and I bought stuff to fix your car resin and I covered this piece and it was so yellow. 

MARK:           It smelled like an old Buick.

ANNA:           Oh my God it was bad. And she’s like, I love it but you’ve got to come get it out of the apartment, it stinks so bad. So, I’m like, okay let me fix this for you. Anyway, did that show in London then brought it to the gallery in Ft. Lauderdale and I moved to Ft. Lauderdale and my parents were there and I was over the greyness of London and that’s when I was coming down to Key West to visit my gallery here and met my husband. Just to fast track and then we decided, oh may be a little dangerous for a new relationship, let’s try to get out of this town. So, we went to San Francisco and lived there for a year and I would shoot my underwater series in Hawaii quite a bit. I’d bring a team of models and do my whole production out there. Then we fell in love with the islands and decided why are we paying all this money in rent in San Francisco when we could live here? 

MARK:           Pay all that money in Hawaii.

ANNA:           Well, own a home in Hawaii, you know? So, we invested and bought a property on the Big Island and it’s on a coffee farm and it’s beautiful and we love it. We got pregnant and had the baby there and then I was like, I want to open a gallery.

MARK:           How did you leave? And I’ve never been and everyone’s like, once you go you don’t. 

ANNA:           It’s so peaceful there. That’s not my personality. My personality is go, go, go and so I wanted to start a business. I just really wanted to prove that I could do it. 

MARK:           And you weren’t like, New York, because that’s where artists go. 

ANNA:           Oh gosh, New York, well New York was great for nurturing me to be a hard worker and not take anything for granted and to understand what it takes to succeed in the arts, so to say. But I think you’re not giving yourself any kind of advantage to produce in that city when you’re up against millions and millions of people. You come to Key West, that’s the great thing about Key West. You are one of 100 people.

MARK:           There’s a lot of art here, too. You keep mentioning New Orleans, it’s like, it reminds me of that little art culture in New Orleans that they also have here. 

ANNA:           But for the most part, I can afford a space here. A space in New York, oh my God. I mean, I can barely afford a space here don’t get me wrong. It’s the most heavy financial decision I’ve ever made, but what made us choose Key West was the tourist traffic vs. the rent prices. Maui – $26,000 for 1,000 sf., in Lahaina. And you maybe have, I don’t know how many hundred people a day. Key West? Do you know how many cruise ships stop at the end…?

MARK:           It’s a million people a year come through Key West.

ANNA:           It’s so many and you have one little street and they are all going to see everything on that one little street so that coupled with my gallery was so successful that was carrying my work, well it has to be Key West. We knew Key West. We met here, we lived here, we said let’s go back to Key West. From Hawaii we had our baby and she was four months old and we brought her on the plane with our dogs and opened the gallery, a week before Irma!

MARK:           And then, your parents were living in Ft. Lauderdale during that time? Right, that’s another decision too because closer to family. When you’re in Hawaii, you are not seeing anybody. 

ANNA:           But everyone came to see me! 

MARK:           It’s still hard to do that, you’re like 12 hours from East Coast. 

ANNA:           True, but you’d be surprised. Everyone was like, so when can we come visit? Same with Key West, I mean, people love it here too. Lots of visitors. 

MARK:           For sure, we were here like four months and we already have people lining up that want to come here. 

ANNA:           Everyone’s lining up, and that’s why you’re building that little backyard. 

MARK:           Okay so Key West …you’re here, you have the studio, you have the gallery, you are seeing success, are you thinking of expanding? 

ANNA:           I don’t know what the future holds for me. I’m, like I said I always look for what’s new and exciting and right now, I think we want to open, and this is out of left field you’re going to think, but a winery in Oregon. 

MARK:           Oh my god, no it’s not. It would be like my dream. If you need me to come work there, in the summers for free because you know the kid.     

ANNA:           We will definitely be taking all the help we can get. 

MARK:           I will work there, my whole family will come, we will bring our own tent, we will sleep in the tent. We just need soap. 

ANNA:           That’s what we are excited about. We are excited about doing something that people can come together and produce organically and enjoy, not only do you get to grow this beautiful thing, but you get to consume this beautiful thing, and with my art background and my husband’s financial background and science background, we are thinking Art + Science is what we are going to call it. 

MARK:           Listen, it’s nature and art combined. It really is, to be able to use nature and I’ve researched a lot on wineries and just, not even being the winery, just being a producer of the grapes and you’re like, I’ll sell to other wineries. Just the, unless you’re buying a winery already, and you’re growing that’s like having a child times 1,000. It’s maybe five or six years before you’re producing anything and then there’s so much science and art and intuition that goes into that. 

ANNA:           It’s the ultimate challenge so we are excited to do that and then have an art gallery within the tasting room and kinda scale back a bit. I think I want to take a breather after these three years in Key West which was the length of my lease. With the amount of overhead that I’ve had to meet, I’ve gone from zero to space I feel like. I’ve just worked myself so hard that I want to get back in touch with nature and nurture. Maybe have another baby, I don’t know. 

MARK:           This is like, definitely a round two, I’m looking at my notes and I don’t know if I’ve touched on anything yet. 

ANNA:           Oh no!

MARK:           Let me ask a couple of other questions, and it’s my fault, it’s not your fault because you’re like, winery and I could go on and skip over that, but I’m like Oh my god, no please. Tell me, and we may have already touched on some of these things, biggest and worst more horrible failure at the time?  

ANNA:           Oh man.

MARK:           Not personal, you, no no about your business. 

ANNA:           No that wasn’t a failure, that was me doing what was right for my life.

MARK:           Congratulations. 

ANNA:           But I guess with the art…

MARK:           Or business… it could have been I should have priced it at this and it did this. Or, I made this and nobody bought it or whatever. 

ANNA:           I think if you’re maybe speaking to take a lesson away from this, it’s that you gotta be a numbers person. You’ve got to accept the reality; it’s not just a dream and they don’t loan people money to buy a house unless you can prove on paper that you’ve made that much money for two years. For me, it’s like I was kind of, well I had no track record. I had no history. But my husband being in finance, he was like, look let’s sit down and talk about and I’ve done this all by myself. He loaned me the money at the beginning and I know this is personal information, but I’m not ashamed of it, he gave me a loan and I’ve been paying him back ever since. I want this to be 100% mine, but what I didn’t realize is how much working capital it would take to sustain growth and sustain the slow season. I think that when you open a business anywhere there’s going to be a season unless you’re in a service industry. If you’re selling goods in a tourist town, there’s usually a season so you have to think about six months of not making any money and you have to think about how am I going to grow this? I have to buy new inventory. I have to move into a bigger space. It all takes money. If you want to grow, you have to have that capital to grow. I think just trying to be realistic about the business side of it and understanding exactly what it’s going to take not only to withstand a year of business, have that money in the bank, but what you’re going to need to grow after that.

MARK:           And not to be ashamed to go to friends or family and this, this is your husband and ask for that. That is so much better. There’s three degrees on how you want to raise capital (1) you want to go to friends and family, the good news about that…

ANNA:           No interest rates. 

MARK:           You’re not going to screw them over either because you’ve got to see Uncle Frank at Christmas and if you’ve screwed him over. Yeah, this is good people. Then (2) you can take a loan which sounds like the 80’s but people can actually take a loan, or (3) you can raise capital and give away a big chunk of your business. Nowadays it’s so easy to raise capital because there’s so much in the system, fake capital in the system that it’s like now you have to answer to someone, and someone else is your boss, you may lose a big percentage of your company, you are now worried about answering to someone with a Harvard degree instead of a business degree of life, why you have to pay back or why you can’t and things like that, and the good news about that is, when you take a loan from a bank or when you take a loan from friends and family, you now are in a cash flow business. You are thinking about how can I make money with the business to not just pay the loan back, but sustain the business. Whereas when you’re getting it from a venture capitalist it’s like, hey it’s been 10 years and we are losing a million dollars a year for the last ten years, that doesn’t take a genius to do that, to lose money month after month after month. But it does take somebody with skill to take the loss and shrink it month after month until you’re now profitable and then you have enough money to start paying back the people that helped you.

ANNA:           I got in that position about a year ago and this time it’s dead, it is the deadest time. Nothing was coming in and I’m like and I was getting so nervous and I don’t want to borrow more money from Steve, I just want to do this on my own, and I’ve been so blessed to have been able to do it up to that point and then I just thought, what am I doing wrong? Do I need to get out of this? I was having all this self-doubt and wanting to just get rid of it and move on. Not think about the hard part of it.

MARK:           Be more of the artist and less of the business. 

ANNA:           Yeah, but I also think the best thing about this three-year lease is that it’s the biggest commitment I’ve ever had to make business-wise and it’s forced me to work through the hard times. At that time, I was thinking like you said, shrinkage, how do I go through find out where I’m losing and cut that and then find out where I can gain and promote that. So, I had to reassess whereas maybe some people would just say, “screw it 

we’ll move onto the next idea.” I thought that I can’t afford to do that. I’ve already invested so much in this; I have to pull it through and that’s exactly what I did. I reassessed and I went out and did a few shows and called a few clients and like, “hey what are you… how are you loving your art today?” You just have to hustle, I guess. 

MARK:           Let me ask you a personal question. 

ANNA:           Sure.

MARK:           Do you hate doing that? Total honesty, over your art? Which one do you love more? 

ANNA:           It’s evolved. 

MARK:           It sounds to me, that you like a little bit of both. You’re like, I like the pain of the business part but you like the challenge of it. 

ANNA:           I think in all honesty, oh gosh, I don’t know. 

MARK:           We can always edit it. 

ANNA:           No, it’s fine. I just don’t want to come off sounding shallow or anything, but…

MARK:           It’s not and I’ll give an example for me. There are, and I’m a big Tony Robbins guy, I’ve gone to all of his events and he has a thing called Business Mastery and one of the things he talks about is people are ingrained with their DNA – is being an artist, an entrepreneur, or a manager/leader. Tony is an artist, because 80% of his time is to do these seminars and 95% of his income is not from those. 

ANNA:           You wouldn’t say he’s an entrepreneur? 

MARK:           No. He says that he’s an artist at heart. But he has built the muscle of being an entrepreneur. So, anybody could be all of it, but at your core like Steve Jobs or Mark Zuckerberg with Facebook, he’s not going to sell it. He’ll never sell it because he’s an artist. That’s a little bit of a difference there. 

ANNA:           I don’t think I can put a label on myself. I’m really split down the middle between entrepreneur and art because as much as I love art and I know that it’s my true gift in this world, I ask God at five-years old when we were in church and they were talking about gifts and I prayed and I said, “God tell me what my gift is?” And I picked up a camera at 12 and everyone told me I was good at it. So, I thought maybe this is my gift. And I have led my life from that, but at the same time I’m constantly wanting to build and grow new things and you could call that an artist or you could call that an entrepreneur. 

MARK:           If I were to give you a billion dollars but you could never be talented at art again, would you take it? 

ANNA:           Yeah. 

MARK:           Then you’re entrepreneurial. There’s your answer everybody! And there’s nothing wrong with that.

ANNA:           That’s shallow but…

MARK:           It’s not shallow, absolutely not, it’s understanding and this whole conversation has been about being self-aware. What a lot of people do is they are judgmental and they don’t really understand. This is why the origin story and the learning about hardship, or the things that you’ve done along the way, is important. She’s a young blonde girl who is an artist and whoopie doo. There’s so much more depth and meat that comes with that, that you have to understand that and you never pass judgment, but you still need to understand those things. 

ANNA:           I felt that judgment really quick when I was in art school in New York, I was in school with all these kids who were doing it for the art. They were true artists. Here I am wanting to sell things with my imagery, wanting to work for advertising agencies, wanting to make money with my talent, right? Because that’s what my mom always did growing up. So, I realized right then and there that I’m in this to provide, like we said, and to have a lifestyle. If someone said, here’s all the money you were ever worried about making and you can just enjoy your life with your family now and experience the world, Heck yeah! I wouldn’t need the art anymore; the art is what gives me the opportunity to live my life the way I live it. 

MARK:           Like we talked about earlier, it’s something you are passionate about doing so you love doing the art. 

ANNA:           Yeah, it brings me joy.

MARK:           And it brings you money.

ANNA:           But it brings me money more than anything, but do I enjoy spending time with my daughter? Or doing a photo shoot? I’d rather be with my daughter. I think that’s where it kinda comes down to. 

MARK:           You could always grow grapes and forget about that art thing. 

ANNA:           And me and my daughter can grow grapes and sell that and we don’t need to show our expression through the camera or whatever. 

MARK:           One other thing that’s good too is that it’s not like, and maybe that answer would have been different if you had just started. You know, you’re so young in the journey of being an artist and owning this studio and the gallery and all that, but you’ve also produced a lot of pieces. You’ve done this, as well. 

ANNA:           Yeah, I’ve gotten that itch scratched you could say. But also thinking more about that question, I feel like it’s kinda loaded because if you take away the creativity, would life just be bland?

MARK:           Right. Well it wouldn’t be creativity at all because there’s no money in the world to eliminate that, you can’t be happy anymore. 

ANNA:           Right, that’s what I mean. Yeah, if you take out any kind of creativity then there’s no spark for life so there’s no seeing things in a way that makes you happy. So, that is a deep, deep question. 

MARK:           It was more about you being more of an entrepreneur at heart who has sharpened the tool of being an artist and issuing that tool to fulfill your entrepreneurial tendencies. 

ANNA:           My spirit, which is get out there, produce something that people appreciate and want to be a part of. It doesn’t always have to make money for me, I just want to create new experiences for people like I’m throwing this crazy party for Fantasy Fest and I’m like, why do I do this to myself? But I want my clients to have a good time and I want it as a challenge to myself, can I do it? Can I pull it off? You know? And if everyone else enjoys it in the meantime, I’ve won. And I get fulfillment out of making other people happy in a way. 

MARK:           That’s great, and then that comes with being an entrepreneur as well. Also, manager/leader a lot of times they are thrown at the wayside like the people that are running the entire ship are very important, but when you’re an entrepreneur you are carrying – not that artists aren’t – but if you are an artist then you’re like, this is my work and I’m doing it this way. 

ANNA:           Right. 

MARK:           When you’re …

ANNA:           Doing it for the people, then you’re willing to evolve and change and do it for the people truly. Give the people what they want!

MARK:           Yeah, give it to them! All right, so what advice would you give somebody that is an artist but wants to get into the, and say they are a hobby artist but they are talented, and they want to, because we are not going to get into how do you feel that you’re talented, that’s a whole ‘nother thing, but if they know they are talented and people have told them they are talented and they want to go out there and start selling their work, besides calling you and showing it to you and your gallery, what do you do?

ANNA:           There’s so many ways, but first you know, if you are talented and you have something that is different, I think that’s the biggest thing to understand that it has to be different, it has to stand out and it’s like the big thing they ingrained in us in art school was that you want someone to look at it and know that that is your work. It has to have an identity. It has to be you. It has to be just as individual as you are. So, if you have that and you aren’t’ just doing the same thing everybody else is doing because you don’t want to lie to yourself that you’re maybe going to be successful if you’re just drowned out by all of the other people doing the same thing, then you could get an Etsy shop. You could sell it on Instagram. You could do an art show. You could do a local benefit at whatever charity is going on and donate some art so that it gets in front of people who will show up at that charity and talk to people about your work. Maybe you never know who you’re going to run into. You could approach galleries, that’s how I did it from day one. I went straight in the door and said, here’s my work, what do you think? Well, we don’t deal with photography, cool, be back in six months. Came back, evolved and if that’s what you really want, you find that third door. You know you find a way to get in and do it and so for that emerging artist it’s just always just look for ways to, if you want to get out there and sell your work, to do just that. It’s like you can start anywhere. You can literally start selling at your kid’s bake sale. I don’t know. 

MARK:           I mean it seems easier when, and I don’t want to make it sound like it is easier for this person or that person, but when you spend your youth through challenges and through getting a lot of no’s to get to a yes, that builds a skin for a lot of business in the future because you can’t just, like I don’t want people listening to think, wow, she went into a studio or a gallery and said “hey, I have this photography” and they are like, we don’t do this and then you just came up with this new original thing and brought it there and were successful. 

ANNA:           I mean, but it was like that. I knew that I was passionate about photography and I knew I was good at photography. I knew that I had something, I had something and I believed in it. When they told me that, I almost did it as a joke, to say “oh is this what you want?” You know? Oh, you like that? Oh cool, maybe I like that, too.

MARK:           Was it competitive? You’re like, I’ll show you, look at this.

ANNA:           Yeah, it was competitive but it was also kinda close minded at a young age to be like, you know, I don’t know – it was and it wasn’t – I was willing to evolve whereas if I was a true artist like you’d say, then maybe I would say, well screw you if you don’t like it then, I don’t want to. But you know what I can be humbled, I can try something new, just like with carrying artists in my gallery, I think that has led to my continued ability to do what I do. I’m willing to evolve and I think anyone in this world that’s not willing to evolve, I mean we are species of evolution, you have to be willing to evolve. 

MARK:           Great answer. I know this answer will probably change throughout your life because I think for me, when I think of the answer now and in 20 years it’s going to be different, but what legacy do you want to leave behind at this moment? 

ANNA:           I don’t often think about that. I am sure there will be one. 

MARK:           What do you think your friends and family would, or people or your kids or people you would want them to say about you when you’re gone? 

ANNA:           That I was incredibly inspiring and a joy to be around, no that sounds cheesy. I should have really gone over these questions before. 

MARK:           No, it’s better to be, like I didn’t know anything about you. For me, I want people to say you know what? This guy actually cared and he did things not expecting things in return. Like to me, that would be a blessing to leave and that’s what people say about me into the future. 

ANNA:           Okay, well I think, I don’t know I see myself as I want to help people be happy and get the most out of life and I love the, well the biggest thing I love about this space on Duval Street is that I get to talk to complete strangers everyday and this woman yesterday came in and she said, “you know I’m a survivor breast cancer and I’ve been thinking about this art that I want to do” and I’m like, well what’s there to think about? Why aren’t you doing it? And she said, “I just don’t know how to start.” And I said well, what have you got? What have you got for me? Like, ask me a question. I’ve been working with resin for years because she wanted to use resin but she didn’t know how. So, I said I’ll tell you right now if you’re going to use casting resin or if you’re going to be pouring deep, you need to use blah – blah – blah and I gave her all these things and you could go on YouTube and learn how. Just go home and I want to inspire people to take that step. To take that leap into finding their own fulfillment and happiness. I get so frustrated when you meet people that say, “well I don’t know what I’m good at.” I’m like no, you’re just apathetic, you’re really just kind of an apathetic person. 

MARK:           Or you’re scared. 

ANNA:           Or scared, or you lack passion. So, I like to inspire those people to believe in themselves and say, well maybe I could be good at this and maybe I should try it. 

MARK:           Great quality to have to be a mom, too. 

ANNA:           Yeah. 

MARK:           Okay, we are almost done and it’s been very long and we’re almost done. Just a couple of quick fun questions that I always ask at the end here. What is your favorite Key West event to attend? 

ANNA:           Oh boy. Fantasy Fest, you can just be who you want to be. You can be creative, you can be crazy, you can be naked, you can do whatever you want and it’s a blast. 

MARK:           And there’s so many days that you can do each one of those in a different day. 

ANNA:           Halloween is by far my favorite holiday ever. 

MARK:           It’s my wife’s too so she likes getting dressed up all the time. 

ANNA:           Totally. It’s so exciting to just be something different for a day. That’s my favorite thing about going to a move, you get to be in a different world for an hour. So, just experiencing that is pretty cool. 

MARK:           What about favorite restaurant to go to?

ANNA:           Nine-One-Five. Upstairs, Point Five. 

MARK:           That was not even a hesitation on that one. 

ANNA:           Go see Andrew and Heather there, they are amazing.

MARK:           Awesome, well maybe I’ll get them on the podcast. What about favorite hidden local spot? That tourists may not know about which is hard now.

ANNA:           Mary Ellen’s is pretty cool. 

MARK:           I don’t even know that. 

ANNA:           Really? It’s right behind me, right beside the old where Two Cents used to be, and Two Cents used to be my favorite. 

MARK:           Yeah, me too. 

ANNA:           They got demolished, but they are going to rebuild supposedly. 

MARK:           Oh, they are? Well, I know they moved the bar and they moved the whole bar to their other location. 

ANNA:           I think they are just getting city approval, but they are going to be back up and running, not too long. But I think Mary Ellen’s is a really cool dive bar they’ve got an amazing little restaurant and it’s like a tiny little kitchen that makes grilled cheeses and they do trivia night over there and it’s fun. It’s like, pretty divey. 

MARK:           I like divey, you need a little divey in your life. What about place for music? I mean we are right across over here from the Parrot. 

ANNA:           Oh, I get blasted by the Parrot every day. Music, I’ve never been but I’ve been told that there’s a jazz brunch at the Ocean Garden hotel? The Gardens Hotel? And it’s not far from here and I’ve been meaning to check it out.

MARK:           Yeah, my wife told me. She didn’t go yet, she’s like we have to go for this jazz brunch at the Gardens Hotel, we have to go. 

ANNA:           I know, we should all go. 

MARK:           Yeah definitely. What about for happy hour? 

ANNA:           Honestly, happy hour, Art + Wine coming soon to Anna Sweet Studios. But, right now I truly, truly love Sunset Key. I like getting out there and you don’t feel like you’re on, well you feel like you’re on an island in the middle of the ocean when you go out to Ocean Key, or sorry Sunset Key and you’re just staring at the water and you get the unobstructed view of the sunset. Whereas, anywhere else you are going to be staring at Sunset Key.

MARK:           What about tourist attraction that you take out of towners to? 

ANNA:           I always like to go to the butterfly garden and I know it sounds cheesy.

MARK:           No, it’s a big hit from a lot of people I ask. 

ANNA:           Yeah, the butterfly garden or I don’t really bother with the Hemingway House it’s just like okay that’s a house cool.

MARK:           Right, and then the guy killed himself and you’re like ugh.

ANNA:           Oh, it’s depressing. Honestly there’s a whole circuit and I’m sure that you hear from people from Key West it’s like just these bucket list things you gotta check off your list. One of them being Captain Tony’s flipping that quarter in the fish’s mouth.

MARK:           I always see people doing it and sometimes they go like one foot over and I’m like buddy, a little more juice into that throw. But there’s a bucket list of people that come and I want to do all these things and I always try to find that obscure thing. Do you have other gallery friends that you can do a little art tour with, or are you just too busy? 

ANNA:           I tried in the beginning. I wanted to develop an art crawl for the city but every person I asked about it, they were like, yeah, we tried that and it didn’t work out and so and so didn’t want to participate and so and so didn’t want to participate. I mean a lot of the art galleries here, unfortunately, have been around for so long and they are so set in their ways and they are so competitive and not really open to promoting any other business but their own. I’m not trying to talk bad about anybody, I’m just, I’ve tried to bring up these things and if I really had the time and energy I would push through anyway and do it anyway, but right now I’m just trying to make sure I pay my rent. 

MARK:           You’re focused on the important things right now. Last question, besides where they can find you and all that, we’ll get to that and that will be the last question. Give us a tip of the day, it can be a new gadget, a new food, a book you’re reading, podcast, anything. 

ANNA:           Oh boy, the pressure is on. Tip of the day, I think everyone should carry and this is going to sound so hippie of me, but everyone should carry their own refillable water bottle because our consumption of plastic water bottles just breaks my heart every day. I get so much joy from refilling this water bottle it’s incredible to think that the oceans are what have made my career and without that ocean I wouldn’t be sitting where I am today. To not be contributing any more plastic to that ocean is something that we can all remember. 

MARK:           They say 2050 there will be more plastic than fish. 

ANNA:           Yes, and it’s the sad truth and every bit of plastic that’s ever been made is still out there today. I think if you can buy a hydro flask and I just upgraded to the 40 because that’s how much water I drink every day and I just, it’s one of the best things I’ve invested in this year and I won’t go anywhere without it. 

MARK:           Awesome, I love that. It’s definitely something to do. People don’t understand when it comes to recycling, we don’t have to end the show on that big hippie rant, but when it comes to recycling of plastics, it goes in tiers. So, let’s say it’s a plastic bottle that you recycle, cool then that maybe goes to a bag. Then from the bag they can’t use it for anything else. Then it goes into the dump. So, all recycling…

ANNA:           And we won’t even go into the fact that 90% of recycling doesn’t actually get recycled because it’s not recycled properly there’s no recycle education. So anyway, that’s a whole podcast for another day. 

MARK:           Where can people find you, find about your work, let’s talk about here in Key West instead of the other locations. 

ANNA:           Here in Key West you can visit me at 513 Duval Street, it’s my gallery, my original space, or my new studio where I produce everything is juts around the corner across from Charlie Mac’s and the Green Parrot and that’s at 417 Southard Street. Pretty soon we are going to be opening a wine bar, so you can come enjoy the art and some really amazing wine.

MARK:           Then online, AnnaSweet.com? 

ANNA:           https://www.annasweet.com/

MARK:           And I’ll put all this in the show notes. 

ANNA:           And that’s on Instagram, too: https://www.instagram.com/annasweetgallery/

MARK:           Like I said, I’ll put all that in the show notes. There’s a couple of other Anna Sweet Instagram things I see.

ANNA:           I have lots of Instagram’s.

MARK:           I’ll put all this, and look, if I was a woman and my name was Anna Sweet, I’d be putting it everywhere too… because it is a very cool name. 

ANNA:           It’s my born name, I did not decide that name for myself. That is my grandfather’s name and it came from the Mayflower, English descent.

MARK:           As long as your husband’s name isn’t sour. 

ANNA:           Ahhh. It’s pretty cool because his Granddad was a very famous Yankee so it wouldn’t be the worst last name to take, but I am not giving up my name. 

MARK:           I wouldn’t not in this world. It was a pleasure talking to you, we dug down the rabbit hole and we could have kept going so I apologize if it was a little long winded and if that’s coming from me and I appreciate everything that you do. You are super talented, you are super down to earth, and people need to come check out your work. Thank you 

ANNA:           Thank you so much.  

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