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As a small business owner, you need to be a lot of things to make your business go—but you don't have to be a marketer alone. Join host Dave Charest, Director of Small Business Success at Constant Contact, and Kelsi Carter, Brand Production Coordinator, as they explore what it really takes to market your business. Even if marketing's not your thing! You'll hear from small business leaders just like you along with industry experts as they share their stories, challenges, and best advice to get real results. This is the 2x Webby Award Honoree Be A Marketer podcast! New episodes coming in July!
On today's episode, you'll hear from an island based entrepreneur who turned her passion for place into a powerful marketing platform, and she teaches others how to do the same. This is the Be A Marketer podcast.
Dave Charest:My name is Dave, director of small business success at Constant Contact, and I help small business owners like you make sense of online marketing. And on this podcast, we'll explore what it really takes to market your business, even if marketing's not your thing. No jargon, no hype, just real stories to inspire you and practical advice you can act on. So remember, friend, you can be a marketer. And at Constant Contact, we're here to help.
Dave Charest:Well, hello, friend, and thanks for joining us for another episode of the Be a Marketer podcast. That can mean only one thing. She's here again, my indispensable cohost, Kelsi Carter. Hi, Kelsi.
Kelsi Carter:Hi, Dave. I love that indispensable. Indispensable. My head got huge.
Dave Charest:Oh, boy. Calm down.
Kelsi Carter:Job security? No.
Dave Charest:There you go. There you go. Listen. I think we are long overdue for yet another DUCA update.
Kelsi Carter:Oh my god.
Dave Charest:What's going on?
Kelsi Carter:Well, I think the latest thing is they have a TikTok page now.
Dave Charest:Congratulations to them.
Kelsi Carter:So I feel like that that is pretty, like, dedicated one that they're actually, like, being posted on, but they're doing really well. We're still getting three eggs a day consistently.
Dave Charest:Okay.
Kelsi Carter:They're loving the pool. They're loving the warm weather, and they can't get enough of it. And we have given them we made them the other day a duck margarita. A duckarita. We called it a duckarita.
Dave Charest:Okay.
Kelsi Carter:So it was like strawberry puree pretty much. We put like a little mint garnish on it, we just put it in one of those, like I think it was like a Moscow mule glass or something like that. But we put that, and then they just went at it, they loved it. Mango practically stuck like her entire face in it. It was so funny.
Dave Charest:Amazing. Good thing you didn't make a mango margarita.
Kelsi Carter:Yeah. Honestly, she probably would have looked at me a little weird.
Dave Charest:So this TikTok page, you said it's a dedicated TikTok page?
Kelsi Carter:There is some, like, lifestyle stuff for, like, my fiance and I, but the ducks are heavily featured on it.
Dave Charest:I gotcha. I gotcha. So well, it's interesting. Right? Like, I think well, one, I know we were talking a little bit the other day how you are are, like, actually starting to, like, plan out some content for this TikTok page.
Dave Charest:So maybe you can tell us a little bit about that. Like, what are you learning right now just in terms of a marketing perspective?
Kelsi Carter:Of course. So my fiancee and I kinda have just a fun time. We're not really try expecting anything from it, but we decided to try to post on TikTok every day for a month at least. We're thinking about maybe doing two months. What our initial plan is because obviously you have to film and post something every single day.
Kelsi Carter:So we have a shared notes app where we go in and we have days of the week, what we're gonna film each day, and then what's gonna be posted each day. So that's held us accountable and just like keeps us organized because then the day will come of like, oh my god, what do we post? But I've been learning a lot about just certain times to post on, like, different days because each day you can have, like, a varying time to post, especially on the weekends. So that's been really interesting. And just learning a lot about the algorithms and analytics in TikTok itself because there are certain things that you can do as a creator that could help boost your video from getting seen if you're doing certain things like creating a template in their it's like a content creator studio, I think it's called.
Kelsi Carter:And if you use a template that is trending in there, they'll boost that post more. So that's something when we first started posting, we had no idea. We would just post and we're like, only getting like 20 views, like, which is we didn't have many followers. So obviously, we're like, oh, who's gonna see this? Now we have 40 followers and we're averaging like seven, eight hundred views.
Kelsi Carter:So Yeah. Which is pretty impressive for only having 40 followers. So
Dave Charest:So interesting thing there. Right? Because this was actually something that I've been kind of investigating a little bit too. So, you know, we always talk about this idea of really focusing on one channel before you start adding another to the mix. And I feel like I've got a pretty decent handle on LinkedIn.
Dave Charest:There are a few things I still need to experiment with and and do, but I've been thinking about more about kind of adding Instagram to the mix. That seems to be the other place where I kinda do some things. And in that, I was learning, and I think it's a good tip to as you're saying, right, pay attention to what things the platform itself is prompting you to do. Mhmm. Because those are the things that, to your point, start to get a little bit more eyeballs on things.
Dave Charest:And it's beyond like, before it used to be really all about, like, who's following you and your following. And now it's really a lot more about the topic and the interest that somebody has and the thing that you might be publishing. And so they don't you don't need to be following somebody for them to see your video. Right?
Kelsi Carter:Yeah. If you just have relevant content that shows up in your for you page, it's perfect.
Dave Charest:Right? And so I think that's a that's a good tip for everyone kinda listening here is to, like, pay attention to what's happening on the platform, what it's prompting you to do, and then taking advantage of those things in an authentic way that it's kind of prioritizing within its algorithms because that might stand a better chance of getting in front of people. So something I I may also start playing around with as well, not on TikTok, but like I mentioned on Instagram. It's funny how the things that we do in life and the things that we're doing in work I mean, I feel like people often talk about that idea of, like, work life balance, and I I actually don't think that's like a thing. Because, like, everything is really kind of integrated today.
Dave Charest:Right? You gotta kinda know when to shut things off and do things. But in so many ways, we're doing our business things. We're doing what we do for work. We're also building our personal brands at the same time.
Dave Charest:Like, all of this stuff kinda plays together and similar, you know, you and your fiance are doing your thing. My wife and I, we do a podcast. And, you know, as we're doing that, I'm like, oh, we're gonna start sharing, like, drink recipes for the drinks that we have while we're doing the show. And, like and then also, you know, we talk about things that we really like, and I was like, oh, we should start a recommendations page. Right?
Dave Charest:Of, like, the things that we enjoy that we think other people will like as well. Right? And all of these things really start to come together to kinda help you build something that could become something else. Right? And I think whether it's, you know, restaurant recommendations or sharing travel tips or even just having a knack for, like, organizing things.
Dave Charest:Right? Like, we often overlook the pieces that can end up fueling something that we do that makes us human from a marketing perspective, especially when we start to think about how all these things connect. And I think our guest today really does a really great job of kind of weaving together, like, multiple businesses, marketing channels, and and even, like, her personal stories. Right? Those types of things.
Dave Charest:And so it's a great conversation that we have for people today, and it really shows how kind of integration, right, both in life and marketing kinda creates this momentum for you, authenticity, and results, right, when you start thinking about what it is that you're doing. So, Kelsey, I wanna go to you. What can you tell us about our guest today?
Kelsi Carter:Today's guest is Cindy Clearwater, also known as Cindy Lee. She is the creative director and content strategist for Cindy Lee Media, and she runs My St. Croix VI, which is a popular island travel guide based in The US Virgin Islands. It literally looks like Adrian. She's also a Constant Contact partner, the founder of IDM Strategy Lab, and the soon to launch Exploranista, which is a platform designed for Gen X women who love to travel smart.
Dave Charest:Nice job on that word there. I was like, uh-oh.
Kelsi Carter:Thank you. I was looking each one like, don't mess it up.
Dave Charest:I was like, I'm gonna screw that up. I'm glad I don't have to read it. Cindy lives on the island of Saint Croix, of course. And she has really built a a vibrant, I would say, multichannel brand that includes blogs. She's got an email list that's very important to the work that she does.
Dave Charest:Events, right, all really tied to her love of the island and really love of digital strategy in many ways. And so Cindy has really turned her passion for island life into this sustainable business by doing something oftentimes a lot of people avoid, which is showing up as herself and really making real connections through both email and the content that she shares. In our conversation today, you're gonna hear how to turn personal passion into a business that markets itself in many ways, why building and nurturing your email list gives you more power than chasing social media likes, and the role of content consistency and integrated tools like Constant Contacts Campaign Builder, for example, in saving time and getting results. So let's go to Cindy now as she shares how she went from marketing Caribbean cruises to building an email list that powers multiple businesses.
Cindy Clearwater:The way I ended up on Saint Croix is I was working for a data syndication company called Hollywood Media Corporation. It was founded by the founder of the SciFi channel, but my section of the company, CinemaSource, was founded by a guy who worked at the AP and then got hired by the New York Times to collect their showtimes. Long story short, he realized he collected at once for the New York Times while he could sell it to everybody. The show movie showtimes in New York. He expanded that globally, started this big business.
Cindy Clearwater:So pretty much any website since the nineties that you've gone to, even newspapers, and it was a big client. All of those movie Showtimes were collected by our office and then that data was sold a million times. So the concept of digital products and scaling your business from digital products was something that wasn't new to me. He got bored though and he decided to start a travel company. I was his assistant.
Cindy Clearwater:He moved me over to be VP of that. We started this travel company February, beginning of 02/2001, scouted. We were partnered with Royal Caribbean. We scouted different places in The Caribbean on the itinerary. The adventure was the boat that we were tied with, and it was just launching.
Cindy Clearwater:Penn launched yet, but we we knew what their itinerary was going to be. Worked on a bunch of Caribbean deals, ended up that I was moving to Saint Croix to set up our Caribbean base. I was VP of operations. We all know what happened unfortunately in September 2001. Mhmm.
Cindy Clearwater:And that was not great for a startup travel company that was just getting off the ground. But I still ended up moving here. I was supposed to move here in October, moved in December. We tried. We tried really hard, but just nobody was traveling.
Dave Charest:Yeah.
Cindy Clearwater:And so by July, the company folded. But in the course of that time, I was developing games. We were kind of taking the concept of a vacation and matching it up with competition like in Survivor and The Amazing Race and The Mole and we were creating this vacation package that you could pay to play these games. So I was developing business relationships throughout The Caribbean and I was working on national ad campaigns. We were working with a PR firm in Manhattan.
Cindy Clearwater:We had hired Amber Birkets from Survivor as our spokesperson. I was helping produce some of our videos. So we were doing a lot of marketing work. I was helping develop the website. And then July 2002, my boss just decided it wasn't just we'd sunk too much money and time into it.
Cindy Clearwater:So he invited me to come back to Connecticut, but I had always, for my entire life, wanted to live in The Caribbean. I was obsessed with Gilligan's Island, where he runs as a kid, because I wanted to live on an island. Right?
Dave Charest:Shipwrecked. Whatever. We'll take it.
Cindy Clearwater:I was like, stay on a Caribbean island or come back to, like, snowstorms in the winter. I was like, no. I'm staying. So I had been working with some local hotels, and they offered me a ton of jobs, different jobs. And finally, they offered me the event coordinator job.
Cindy Clearwater:So I took that and became a wedding planner and event planner, which I'd been doing events already for the other company for years. So that was kind of in my wheelhouse. After about six months of working for the resort, I really decided that I wanted to be my own boss. So I branched out, still kept some of my resort clients. They came with me and I still produce their weddings.
Cindy Clearwater:I didn't wanna leave them high and dry. So that was when I started in 02/2002, my destination wedding business. There was a need for it here. There was a market for it. But I needed to market my own business.
Cindy Clearwater:So I started the business and really took my knowledge of the digital space in those early days of digital marketing and media. I knew I needed a website. I taught my I had somebody start a website for me, but I knew what I wanted so I taught myself basic web design, got that up there. In 02/2007, I went back home to Massachusetts for a year and interned with a graphic design company that my mother runs in Massachusetts. So got a little more marketing and sales and graphic design experience under, but I still came back in 2008 to my wedding business.
Cindy Clearwater:But at that point, social media had started. I had some good sales and graphic design marketing under me. And frankly, the wedding business here in the islands, it's seasonal and it's very hard, like many things, to make enough money doing those things to still be able to afford to live here. So I started branching out and helping a lot of the wedding vendors that I worked with and some other small businesses here to market their businesses through social media. And at that point in time, I had become familiar with and became a partner with Constant Contact.
Cindy Clearwater:So started to teach people how to use email marketing. So it all kind of evolved together. I was market doing marketing and graphic design business alongside of my wedding business, but I was also marketing my destination wedding business and doing a really good job at it. I had a very good corner on the market here. But anybody who's worked in that industry, it's a very emotionally charged job Yeah.
Cindy Clearwater:Dealing with the most important day in many people's lives at that point. And so after about fourteen, fifteen years and when hurricanes Irma and Maria came through, I just decided it was time to retire from that and focus full time on supporting small business and entrepreneurs with their marketing. And my St. Croix really kind of grew out of my destination wedding business as well. So I started focusing in that.
Cindy Clearwater:When I was planning destination weddings, would have two, twenty, 50, a 100 people coming to the island and they'd all ask me the same things because the guests would get in touch with me for travel arrangements. They'd be asking me where should we eat? What should we do? What are the excursions? What do we need to not miss?
Cindy Clearwater:And over time I found I was answering the same questions over and over and over again. And I was like, I know how to build a website. Let me build something over here where when they ask me these same questions over and over, I can say, go over here to get more information. So it all kind of evolved out of me finding demand and sort of filling a niche for market demand here in The Virgin Islands.
Dave Charest:Was starting a business something that you kinda thought you would end up doing or or like how did that even I I mean, I know how you'd kinda transitioned over to that, but was that something that was kind of always on the on your foresight?
Cindy Clearwater:I don't think so, to be honest with you, but maybe in the back of my mind. I mean, I was that kid. I had a paper route when I was a kid. I was that kid that was always looking to make extra money so I could buy the things that I wanted to get that maybe my parents didn't have a budget for. So I think my entrepreneurship is something that's innate.
Cindy Clearwater:I've always worked. I've always worked a couple of jobs and living in the islands is not like it's great when you're on vacation. Yes. But when you live here, it's a pricey lifestyle. And not because necessarily we're out every night and partying all the time, but just the cost of living is expensive.
Cindy Clearwater:So, you know, most people here have more than one job if they're here working. And so I think it just kind of evolved from me just always looking for a way to make sure I could stay here in The US Virgin Islands and have a decent lifestyle. Yeah. So I think it's just kind of always been in me to look, how can I do this? I definitely am somebody who likes to figure out things and how I can make something happen.
Cindy Clearwater:So just kind of I kind of fell into it.
Dave Charest:Well, what do you love most about running your own business as you've transitioned into doing that?
Cindy Clearwater:I like that I can set a goal for myself and work towards it. I don't have somebody telling me, oh, you can't do this. It's challenging for sure. Anybody who's run their own business knows that it can be real challenge sometimes. But when you achieve certain things, when you can expand, when you can pivot, which I think is so important in today's economy, figuring out ways to pivot.
Cindy Clearwater:I think it's just really kind of self satisfying to know that I can figure something out, figure out, all right, if I'm taking my business in this direction, but this isn't really the way it should go, The market's going over here. I have the ability to pivot because I'm making the decisions.
Dave Charest:Mhmm. Well, you mentioned some of the challenges here and and particularly with the economy going on. And so I actually have a pointed question about the economy. I mean, how would you say or how has inflation impacted your business over the last year, let's say?
Cindy Clearwater:It's definitely had an impact. I definitely have seen a reduction in people who want to hire marketing services one on one. I see a lot more people trying to do the DIY route. I specialize really in organic marketing so that's helpful because people's paid marketing budget is definitely down. But I think that on the bright side of that, especially where Constant Contact comes into things, is that I've had opportunity where a lot of people have been so focused on social media and growing their followings, which they don't really own as we know.
Dave Charest:Yeah.
Cindy Clearwater:I've been able to point out to people in this economy how valuable it is to have an email list where you've got people that have already said, hey, I'm interested in what you've got. Like, I wanna learn more about you. So here's my email address. Tell me more. And you own that.
Cindy Clearwater:You own that list and then you are able to remarket to people who've given you the opportunity to land in their inboxes. So I think the economy has been tough on people who are marketers but if we can find the areas that we can shift the client's focus to where they have a little more ownership, I think it definitely is a positive because, you know, the market's gonna go back up, economy's gonna go back up again, everything ebbs and flows. But if we can teach people right now how to hold on to their following through list building, then we're gonna make them even stronger when things start to swing up again.
Dave Charest:Yeah. I wanna talk dig in a little bit more in some of these things, but I guess maybe first, help me understand, like, what are the things that you're doing? And I guess you tell me, like, what's different between when you think of, I guess, your consulting business. Right? But then you've also got MySaintCroix.
Dave Charest:Like, how are those businesses different? And I guess, what are the things that you're doing to market them?
Cindy Clearwater:I guess I'll start with MySaintCroy because that's probably my biggest following is MySaintCroy. And that's also my testing ground, which is kind of a good thing to for me to have a business that I'm marketing that's marketable because it's, you know, about vacation and aspiration and beautiful pictures and sunny beaches. So I'm able to use that as my testing ground for new marketing techniques, for new platforms, to see what works and doesn't work. If something works really well for my St. Croix, then I'm going to start to apply it to clients that I'm working with or if I'm teaching a class, I use it as an example a lot.
Cindy Clearwater:So one of the things that I have found really useful, I started it as a blog and also a business directory. I realized early on when I was trying to sort of set myself apart from other island guides in The Virgin Islands or on Saint Croix that had business directories that were promoting local businesses, I realized one thing that every traveler has in common, literally no matter where they go in the world, they don't have to stay at your resort or your Airbnb, they don't have to go on your boat, they don't have to do your excursion, but they all have to eat. And most of them are gonna eat three times a day. So I really focused on my restaurant guide and I focused on it not just being a paid guide. I do have paid spots and that bumps restaurants up on the list, but I list all the restaurants that I would recommend or that I go to whether or not they pay me because everybody's got to eat.
Cindy Clearwater:So because I have a really robust restaurant guide, it's become a go to for people that are traveling and even for people who live here. From there, I was able to branch the directory out to places to stay, doing some affiliate marketing. But I also really do a lot of blog posts that are about the culture and the history of the island and about the nature, about the marine animals because that's a lot of interest. So I'm able to capture people who are looking for a restaurant, but then capture their interest to keep them coming back. Several years ago, I was offered the opportunity to take over, an entertainment calendar that a friend of mine had started many years ago for just live music.
Cindy Clearwater:He literally started it off by sitting at the bar and asking people for their email addresses. This is like, I think, gosh, twelve years ago. I was one of the first people on his email list and he just blind copied people. It was something he did in his past, you know, his hobby. He loved a few he was really good friends with a few of the local musicians.
Cindy Clearwater:He loved going to live music. Everybody loved him. Great guy, Joe. And, he started email marketing that way. He didn't have anything fancy.
Cindy Clearwater:Eventually, somebody helped him out with a little bit of a website where he could post some things, but he was still doing things very like grassroots. Sadly, he passed away from cancer several years ago and so the people who had given him the website sort of took things on. It went through a few different hands because it's a lot of work and not a lot of return on the investment and eventually I was given the opportunity to sort of take it over. Because I had such deep experience with email marketing, I recognized the value of it. So and that it was a great compliment to what I was already doing with my blog.
Cindy Clearwater:So I inherited an email list of subscribers. I already had a great email list for my St. Croix. And so what I started developing was, a little bit different. He they would send out just a weekly rundown of the events.
Cindy Clearwater:That was it. And people subscribed and it was great. But I recognized that I wanted to tie in more St. Croix information, a little more news. So it took me a little bit of testing to see what would really work.
Cindy Clearwater:But now for the past, I think, five years, I send out an email every Friday to people that have subscribed. But I have a lot of people that stay on even after they come on vacation and they go back home. They stay on my list because every email opens with a beautiful image of the island or an event, something going on, but something really, like, enticing to remind people in the dead of winter how nice it is here on the beach. I start with a little opening and I've made myself vulnerable. I talk about what's going on on the island.
Cindy Clearwater:We just had a tropical storm go through here and it was the first big storm really that's affected us since Maria, which was a category five that decimated the island. So there's a lot of storm PTSD going on on the island. So I talked a little bit about that and things I learned. So every week, I talk about something that's going on. Maybe it's the boat parade or it's an event going on or it's just how gorgeous the weather is.
Cindy Clearwater:And then I give the rundown of the next week's calendar with links to my web calendar website so people can go get more information. And at the bottom, I usually have a sponsor or a product. Right now, I'm selling calendars, wall calendars that I do yearly to help fund all the work for this. So I found that I have not only developed an email list where I'm sharing information that's valuable. They learn what's going on on the event calendar for the next week, which is great if you're visiting the island or if you live here.
Cindy Clearwater:But people have made a connection with me. I've been recognized on planes in Chicago, which is kinda mind blowing. You know, I get recognized here sometimes, but I don't do it for the recognition. I do it because I really love the island that I live on. And by me highlighting our island, it supports fellow local businesses.
Cindy Clearwater:But what I've really learned is that and through experimentation through is that the way to market your business through your email list is to make a personal connection in your business. And when I started, for so long, I was worried about being that person that was on my the face on my social media in every picture. So I wasn't in any of the pictures. It was all landscapes. It was all events.
Cindy Clearwater:I was always behind the camera. But when I realized in my email marketing that talking about what was happening in my life on the island and what island life was like, people wanted to see me a little more. So it's helped me to come out from behind the camera a little bit more on social media. Still not too much. I don't wanna be that girl.
Cindy Clearwater:But, but I found making those connections, I get the loveliest replies from people to my calendar emails. They really do think I'm talking directly to them. And I really am because I have my ideal client in my mind and I'm talking to that person. It keeps me going because people tell me either in person or in email replies that they value what I do. And all of this is just because I wanted to get a calendar out to people.
Cindy Clearwater:But making those connections is really helpful. And then on the flip side of it, like any business, I do need to make money. And so I sell products. I I have my wall calendars that are for sale right now and through that I've made these connections throughout the year. So I do pretty well.
Cindy Clearwater:I would say at minimum 95% of the sales I make from my wall calendars each year are from my email list. That's where they're gonna happen from. And I take all of those things that I've learned and I'm able to translate them into the businesses that I work with to try to figure out, okay, I work with a local dive business, helping her with some of, we're helping them with some of their marketing. How can I take what I've learned through my St? Croix and help them apply it to what they do?
Cindy Clearwater:I've worked with medical practices. How can I help them make a personal connection with somebody, give them valuable information that's going to keep them coming back for more and recognize that, okay, they've given me all of this great information about preventative health? Now that I've got something I need to deal with, I want to go there. So I try to take what I've learned through experimentation in my own business and figure out how to twist it and mold it to apply it to other businesses.
Dave Charest:A couple of things, I guess. How do people find My St. Croix then? Right? Like, how do actual people get into your circle?
Dave Charest:Right? Like, how do you get people there? And then I guess similarly, how do you get the word out about your consultancy? Like, how do people find you if they wanna work with you in in a marketing perspective?
Cindy Clearwater:So as far as my Saint Croix goes, SEO, I'm really good at SEO. Like, really sparks me. I it's kinda like a puzzle to me and a challenge. So I'm always looking at what are people searching for when it comes to travel on Saint Croix and how am I going to get them to my website? What are they looking for and what can I give them to match up so that I rise to the top of that SEO search?
Cindy Clearwater:Then when I get to my website, I have pop ups that encourage them to join my email lists immediately. And for me, sometimes I'll have a lead magnet whether it's a discount. I I do on on my online shop, sign up, get a discount automatically to shop online. But also it's just, you know, get my weekly email, learn about island life, and people are really curious about island life, whether they're dreaming like I did for all of my childhood or they're in the plans or they live here, they wanna know more. So email capture is huge so that I can go back to them.
Cindy Clearwater:And from there, those people that have joined my list become fans and they share that information. If they're travelers and they're coming with other people in a group, they share information about my website, go here. I also spend time doing a lot of social listening. So I pop into the groups on Facebook in particular where there are people interested in the island or island life, and I listen to what they're asking for. What are they searching for?
Cindy Clearwater:What questions are they asking in these groups? And I try then to curtail some of my information to answer those questions. Sometimes they'll drop a link. Oh, I've got that information here for you. Or I'll just say, wow, everybody's looking for what's the best restaurant for a birthday to celebrate a birthday.
Cindy Clearwater:Okay. Let me sort of put some information together about great restaurants for celebration. So, you know, I'm always looking from that perspective. So it's SEO. It's lead capture.
Cindy Clearwater:It's word-of-mouth. A lot of the Airbnbs, hotels, whatnot, they're trying to entice their guests to come to St. Croix. So they're gonna tell them about my website because I sell the island
Dave Charest:Right.
Cindy Clearwater:As well as things. So so that's kind of how I've I've been able to market and get a good piece of the market. As far as marketing my media business, that has been a challenge for me because that's really me. It's my name. It's Cindy Lee Media.
Cindy Clearwater:And I have for many years had, you know, the luxury of having a lot of word-of-mouth. I work with a lot of clients who know me through my Saint Croix or they know me from other businesses. We're friends. It's a very small tight knit community down here. So I get a lot of word-of-mouth but I'm really trying to branch out more now.
Cindy Clearwater:So I'm a lot more focused now on my business. My Saint Croix is a travel focused business. I'm a b to b business. So I'm putting a lot more emphasis starting to get a lot more emphasis on on LinkedIn because that's where other businesses are hanging out. I am doing a little bit more on social media on Instagram to try to get some of my classes and courses out there.
Cindy Clearwater:I just did a great summer camp. I did it for the second year in the road which is somewhat modeled on Constant Contact Summer Camp. I kinda got that idea from it of having like three weeks of a little more intense information. So I had a great group of entrepreneurs and small business owners. So I kind of hope for them to like get out and tell more people who tell more people.
Cindy Clearwater:But also SEO, that can be harder when you're a marketing business because you really do have to niche down because nowadays everybody's a digital marketer. Right?
Dave Charest:Yeah. Yeah.
Cindy Clearwater:I mean, it seems to be the buzzword these days. I'm a digital marketer. A lot of those I'm a digital marketers are selling master resell rights and they haven't even taken the course. And so it's kind of hard to weed through that to be like, no, really, really I am a digital marketer. I've been doing this for like twenty five years now.
Cindy Clearwater:So that can be kind of a challenge to sort of sell me and get out there. But again, through that, it it's a lot of trial and error and list building, list building, list building. You know, once people find out about me, I hope to give them reasons through lead magnets, through valuable pieces of content, getting them to know me and what I do and what I offer so that they wanna get on my list. They want to maybe get one of my freebie courses or something so that eventually when I'm launching something a little bit bigger or if they need one on one help, I do offer one on one sort of done for you stuff coaching and then also classwork. So, you know, it's a lot of trial and error.
Cindy Clearwater:It's a tough market, but if you're able to find that niche of people and for me, my niche, my ideal client really are Gen X women entrepreneurs and small business owners who really know their stuff in their business but are maybe a little intimidated by some of the tech but see the value. So they wanna learn a little bit more, whether it's that they wanna do it themselves or be informed enough to hire somebody to work with so they're not, like, giving away the keys to the kingdom.
Dave Charest:Yeah. Yeah. Well, I'm curious. You you know, you mentioned goals earlier and that you like to, you know, set those and work tow towards those things. So when you start thinking about where you are now, what's that process like for you?
Dave Charest:What are your goals right now for the business? And and when do you start to, like, think about those things as you move into the next year?
Cindy Clearwater:Goal setting has always been challenging for me, to be honest. Like, cause I have so many ideas going on and I have so many goals and so many things I wanna do, narrowing them down. But I've, in the recent past, become a huge fan of SMART goals. I tend to be a deadline oriented or deadline focused person. Maybe it's a little bit of adult ADD, but if I have a date that I gotta get something done by, I'm more likely to achieve it.
Cindy Clearwater:And if it's specific rather than being like, I wanna be like the best, like the most popular travel guide on St. Croix next year. Like, what does that mean? You know? But if I break that down to, okay, in the next six months for these search terms, I want to be within the top five results organically.
Cindy Clearwater:I want to increase my social media following by a thousand over the next three months. That might not be so achievable these days, but, you know, by having those goals. So I have become a big fan of that because it is measurable and it's something I can write down and I can put in front of me and it feels good when you achieve them too. I think that gives you a sense of achievement and now I can move on to the next thing. So I've learned to take those big goals of I want to be the best and break them down into bite sized nuggets.
Cindy Clearwater:Okay, here's the next step. So for me, the next step for my St. Croix is that I do want in the next six months, for some high level key terms to make sure I'm coming up in the top. I wanna grow my email list by another thousand And we're coming it's been slow. Summer's always slow for everybody, but I have pretty consistent growth on my my lists.
Cindy Clearwater:So that's good and and on my social media. The other side of things for my goals is I want to get my new website, Exploranista. Travel out there to tell stories about the places I've been and encourage people to travel. I think that's how we become better human beings in this global world is by learning about other places and Mhmm. How people do things different from us and just appreciating other cultures.
Cindy Clearwater:So that's really important to me. And for Sendili Media, I really want to grow my courses. I have some goals of expanding my list building and launching a course this fall that's focused very much on email marketing and list building because I do think from all the things that I see out there in the world right now, the courses that people are selling online courses where so many of them sort of fall short is the email marketing side of things. And not just, hey. You should build a list.
Cindy Clearwater:Do you need to build a list? Do you need to have a lead magnet? But how to do it? Yeah. The actual, like, nuts and bolts of how to get it done.
Cindy Clearwater:How can you grow that? What should you be focused on? What are your content pillars? What are content pillars? Those kind of things.
Cindy Clearwater:We touched on a lot of those in my summer camp, my three week summer camp course. And that's also a testing ground for me to see, okay, what do I need to teach more of? Where do they need more information? And I pretty consistently find that people need more information about list building and the value of not just sending an email once a quarter to sell something, but actually nurturing people and setting up those nurture series and those automations that can help nurture somebody on autopilot so you can focus on growing your business.
Dave Charest:Well, let me ask you this. I mean, with with so many things going on, right, like between the different things and the different goals that you are setting for yourself and the different businesses that you have, how do you actually approach then getting things done when it comes to the marketing pieces?
Cindy Clearwater:That's a great question. I am a calendar user, and I like building out time. So many people fell into home offices during the COVID pandemic and realized the beauty of remote work and working for themselves, but I've been doing it since 02/2008. I've been working from a home office. So I really learned the value of having a set space and having a time.
Cindy Clearwater:This is my nine to five job mostly, but as an entrepreneur, we know it's more than nine to five. But I have a schedule. I come in here at 9AM. I say to my dog, let's go to work, and he knows let's go into let's go into the office. So I have a schedule.
Cindy Clearwater:I use my calendar. I block things out. I use those SMART goals to sort of backtrack. And that's something interestingly that I learned from wedding planning. I was really amazing at timelines, day of wedding timelines down to like the ten, like nine, ten.
Cindy Clearwater:We are going to do this. And it all started from, alright, here's the end goal, walking down the aisle, cutting the cake, whatnot. What do I need to do to get to that end goal? Who needs to be where, and how do we work backwards from that? And so I really do that when I'm working on a project with a deadline.
Cindy Clearwater:I know, okay, this has to be done on this date. What are the things that need to be done to get to that completion? When do I need to fit that in? So I actually mark things out on my calendar. On this day, I'm working on this.
Cindy Clearwater:On this day, I'm working on this at this time, this chunk. I also know I've learned from myself working for myself for so long and working in my own home office. I know what time of day I'm most creative versus when my brain just wants to shut down and maybe do something that's like just easy grunt work stuff that I've gotta do. So I try to build my daily calendar based on, okay, I'm really creative and my mind is really focused first thing in the morning for the first few hours until lunch and then around lunchtime. I also am very adamant now and that for years I wasn't.
Cindy Clearwater:I take a lunch break. I walk out of my office and I take an hour lunch break and I might I live downtown which is nice, so I might walk downtown and grab something or I might just make lunch in my kitchen and sit down, watch TV for an hour, but I take a break and then I come back to it. And I know that in the afternoon is when I'm good at sort of like goal setting kind of stuff and thinking ahead. So I break down my day based on where I know during the day I'm gonna get the most done. And yeah, I'm just sort of backtracking from this is when it needs to be done, this project, and what are the pieces that need to be done to achieve that?
Dave Charest:Got it. Well, talk to me a little bit about, you know, what brought you to Constant Contact through all of this?
Cindy Clearwater:So interestingly, you know, I was thinking about that in anticipation of of this podcast. So it was actually a political campaign here locally, believe it or not. Yeah. It was an email I got back, I think it was 2006 or 02/2007. I was still on St.
Cindy Clearwater:Croix. And I got this email from a a governor's campaign and I saw the little logo at the bottom and I was like, that's interesting. So there was a link at the bottom and I clicked on it to learn a little bit more and I saw that I was getting emails through there. Prior to that, like most people, I was blind copying, you know, groups. I wasn't using an email service provider really for email marketing in that way.
Cindy Clearwater:So I was on that list and I started to see things. While I was stateside, I actually picked up a marketing client who needed some design work, who was a friend of a friend in Massachusetts and she needed to get some email marketing out and I was like, you know what? I heard of this constant contact company. This would work in well. She did real not real estate.
Cindy Clearwater:She did sort of event planning, but for corporations and and sending them to resorts. So she worked with a bunch of different resorts and
Dave Charest:Yeah.
Cindy Clearwater:And had she already had an email list. So we built out her email marketing. She was kinda my first email marketing client, and I realized I was only up there for the year. I was still running my wedding business and planning to come back to it. So I had all these past clients on my own email list.
Cindy Clearwater:So I started using that to encourage them to share the information about my business. If they were coming back down, share information about St. Croix. So yeah, it was through somebody else and then a client and started test marketing and when the partner program became available, I jumped on it. I was like, yeah, this email marketing thing is going somewhere.
Cindy Clearwater:I wanna be in on this.
Dave Charest:So many years later. Right? We're coming up on thirty years for for Constant Contact, which is is is amazing. Right?
Cindy Clearwater:Wow.
Dave Charest:Well, what are the results that you've been seeing from using Constant Contact since you've jumped on board with that?
Cindy Clearwater:The results from it are sometimes immeasurable, but I guess they are immeasurable because we have such great backend data that we can can glean so much information from. What have I learned from it? I mean, it's grown my business. It's helped me reach other people. One of the things that I do when I try to do it very carefully is because I have a huge following or a good size following for my St.
Cindy Clearwater:Croix on my email marketing list, I recognize that among those people that are travelers, there's also small businesses, there's also entrepreneurs, whether they live here on St. Croix or not, that I can help. So I do some cross marketing into that list from time to time. I try to do it very carefully and infrequently because when I do it, I do get some drop off. That's okay.
Cindy Clearwater:I've learned over time that when people unsubscribe, that's actually a good thing because some people are interested in what I've got for the season, literally here for a season. Right? I don't want them to be on my list. I don't want them to be taking space and me paying for them if they're not interested in what I've got. And because of that, I have a very highly engaged list.
Cindy Clearwater:I have great open rates. So I know that I can reach out to them for my other business. I've already been growing a list that are interested in my travel Exploranista website. So I've found ways to sort of offshoot them by segmenting them, by saying, hey, if you're going to be interested in what I'm going to do over here, click here, put them onto a segmented list so that I can then reach out to them and target. Alright.
Cindy Clearwater:Now I've launched. Click over here to subscribe to this list. So I've been able to grow my ancillary businesses or my other businesses from this pool of people by recognizing that some of them, not all of them might be interested in what else I'm doing over here and being careful about not just mass emailing all the time about everything Cindy Lee Media is doing but when it might be relevant or I might be able to get some crossover, I'm careful about it. And it's helped me to stay top of mind. Somebody might have come to Saint Croix and loved the island and they're not, you know, they're not gonna come back next year or the next year.
Cindy Clearwater:Maybe four or five years later, they're coming back and they remember me because they're getting my email or, you know, they got the email for a while and they're like, oh, well, now that I'm planning my vacation again, I I remember Cindy. They don't necessarily always remember my Saint Croix, but they remember me, which is kind of good because I've made that relationship with them. And it's because I can get into their inbox. You know, when you look and I I tell my marketing clients and my students all the time, you might have 10,000 followers on a social media channel, but the stats are like two to 3% of them are actually even going to see what you post organically. But if you have a really engaged email list of 5,000 and half of them are opening what you're sending, that's a heck of a lot more.
Cindy Clearwater:So recognizing the value of keeping them on the list, of nurturing them by not just sending them, hey, buy this, hey, buy this, hey, buy this, I'm selling this, hey, look at me, look at what I'm doing, but meeting them where they are and recognizing what they're looking for and just nurturing them and becoming friends. I like to say that all the time. You have a friend in the Virgin Islands. I get people that email me, hey. We're we're down here.
Cindy Clearwater:We'd love to meet up with you, you know, and sometimes I do. I I end up with friends.
Dave Charest:Have you played around with any of the AI features within Constant Contact recently?
Cindy Clearwater:Yes.
Dave Charest:Tell me about that.
Cindy Clearwater:It's like angels saying when you when you launch the multichannel marketing. That is like literally in the, I think, fifteen years more that I've been with Constant Contact, the most excited I've been is the multichannel marketing. I've played around with it. Part of my summer camp that I just taught was about utilizing AI for your business and how to train it to be the best assistant you've ever had. This is the best thing that's ever happened.
Cindy Clearwater:You know, just walking through it, we did some modeling over summer camp with it by using ChatGPT to help come up with the information to feed into your multichannel marketing campaign, setting a goal, knowing what your content pillars and your voice are and walking through. So then it just cranks out social media posts, premade emails, sets dates for you. I just used it for my Saint Croix. I've got a whole series that I've got ready to roll out. Sometimes, especially when you're a solo entrepreneur like me, you just kinda get stuck in your own head.
Cindy Clearwater:So using AI in the right way, not to write everything for me because I rewrite a lot of what AI comes out with, but it gives me a starting point. One of the things I talked about in the course that I did was that think of it like that AI, like that intern or that brand new assistant that knows nothing about your business. You need to teach them everything about what you do. Teach them everything about what you do. But when you have that assistant, no matter how brilliant they are, even if they went to Harvard, you're not gonna let them just run your business for you and be your voice.
Cindy Clearwater:You're still gonna put yourself into it. So use them in that way. Use AI like this amazing, brilliant assistant, but still make it your own, still still do that. And I find the multichannel marketing is like that. You know, it give gives me a framework and then I can look at it and say, okay, maybe not this email, maybe not that social media post, maybe I wanna do something slightly different, but this was a great starting point.
Cindy Clearwater:And I also love with AI, using AI as my assistant, including the constant content AI. If I don't want to use that exact framework, they're not going to get mad at me. They're not going to feel bad that I changed something. You know, I'm not insulting them in any way to say, try again. You know?
Cindy Clearwater:But I I find it so brilliantly helpful.
Dave Charest:Yeah. Yeah.
Cindy Clearwater:It takes so much time.
Dave Charest:Well, I was gonna say if you had to say maybe just like even thinking from a time savings perspective, how much time would you say that the tool like the campaign builder saves you?
Cindy Clearwater:Hours. Hours and hours and hours. Because it does give you a whole list of things that you can then go in and batch and have scheduled. But if I were to sit down and start to think about it and start to think about where on my calendar, where I should put this, how I should do it, I mean, just the buildup of content creation is huge. This instead gives me a framework that says, alright, now I know what graphics I wanna go look, what images I wanna pull, I wanna tweak this.
Cindy Clearwater:This wasn't exactly what I wanted to say, but now it gives me like three more ideas. Yeah. Hours and hours and hours. It's huge.
Dave Charest:What would be your number one tip for a similar business maybe getting started with Constant Contact?
Cindy Clearwater:Absolutely make sure from day one on your website, you have list building or email capture built in. Even if you don't have a lead magnet, you don't know what you're gonna do, at least put it out there and say, hey, if you wanna keep in touch, give me your email address and share that everywhere. Don't just leave it on your website. Share it at links to it in your stories. Share it in the bottom of your email when you're talking to people.
Cindy Clearwater:Share links to it. Start capturing emails from day one because you never know whether you're selling a product or a service or whatever it is. You have a blog. Somebody might stumble across you for whatever reason by accident but not have time to really go through what you've got. But they might say to themselves, oh, wow.
Cindy Clearwater:Like, I'm really interested in that and I wanna learn more but I don't have time right now. I'm gonna give you my email. And now you have an ability to reach out to them and they have their inbox and they can remember who you were. I mean, how often how many websites do we go to on a daily basis that we see something? There's so much advertising, so much marketing out there.
Cindy Clearwater:We see so many things bombarding us and we see things that we like. I like this widget over here or I like that product. And then you get sidetracked with 18,000,000 things and you forget what it ever was. So I give my email up to places, to websites, to products, to services that I think I might be interested later on all the time so that I don't forget. Mhmm.
Cindy Clearwater:And so then the second part of that is make sure that you're sending something out to them. Make sure you're nurturing them and you're reaching out to them so you stay top of mind. It's how you separate yourself from the next guy because most people aren't doing that.
Dave Charest:Well, friend, let's recap some items from that discussion. Number one, start capturing emails from day one. Make sure you give people a reason to sign up and make it visible across your site and social channels. Cindy's seen 95% of her calendar sales come directly from her email list. Don't wait to start building that audience.
Dave Charest:Number two, make your marketing personal. People want connection. When Cindy began sharing stories from her own life in her weekly emails rather than just a beautiful beach photo, she saw deeper engagement. Your audience wants to hear from you, not just see what you sell. Number three, use one business as a testing ground for others.
Dave Charest:Cindy uses my Saint Croix to try out marketing ideas before bringing them to clients or courses. This not only sharpens her skills but creates real world case studies she can teach from. It's a great reminder that your own business can be your best lab. So here's your action item for today. Use Constant Contacts campaign builder to generate a multichannel campaign.
Dave Charest:Pick a goal, like selling a product, promoting an event, or even just growing your email list, and let the AI powered tool give you a starting framework. You'll get emails, social posts, and a calendar in minutes. Then make it your own just like Cindy does. That first step saves hours and gets your momentum going. I hope you enjoyed this episode of the Be a Marketer podcast.
Dave Charest:Please take a moment to leave us a review. Just go to ratethispodcast.com/bam. Your honest feedback will help other small business marketers like yourself find the show. That's ratethispodcast.com/bam. Well, friend, I hope you enjoy the rest of your day and continued success to you and your business.