Cindy Winslow

Copywriter Cindy Winslow left 20 years in real estate to start Your Cup of Copy, a virtual copywriting business. She uses AI for brainstorming, focuses on storytelling for clients, and has shifted from serving realtors to writing LinkedIn profiles and newsletters for entrepreneurs. She shares tactics for profile optimization and talks about emerging platforms like Chatter.
Chapters
All right everyone, who's Cindy Winslow? I have zero idea. I do love your cup of coffee, is awesome. So Cindy, hello, you're live, you're brave, you're beautiful, you're brilliant, and like to do this, to go live. So tell us about yourself because I have no idea.
Well, this is very unlike me to do live without preparation. Um, I am Cindy Winslow. I'm a copywriter and I run my own business, Your Cup of Copy. Um, I kind of have a fondness for coffee and I played off of that when I named my business. I was looking at something— should I do something very professional so people take me seriously, or should I use some of my wit? And I decided to go with the wit and fun side of me.
I love it. All right, so let me guess, just with the title, if you think you what it is, put it in the comments. Your cup of copy— you are a copywriter creating content for businesses. Yes. Then you did what you need to do. Like, I love it. Your, your cup of copy. And then how else do you like market that with, um, with that fun phrase that you have?
We brew copy that converts.
Oh my God, I love that. Okay, so tell me about the start. So like, have you always been a copywriter in business?
No, I, um, spent 20-some years as a full-time real estate agent, mentor and trainer, and I had an opportunity to start a nonprofit with a couple other real estate agents, and we built new homes and modified existing homes for people with disabilities.
I love that job.
I thought that was where I would retire. And we had— our parent company was also a nonprofit. 2 years to the day, we got a phone call from them saying that they had their funding cut and therefore they shut us down. And I understand their situation, but at that point I had been out of full-time real estate. I was still using my real estate skills and marketing in that position, but I, um, I wasn't doing the weekends and the evenings and all that as much anymore. So I couldn't really see myself going back to full-time real estate. I was getting remarried. My youngest daughter was a senior in high school. My husband traveled a lot, so I wanted something that I could do and travel with him. So at that point, I knew a virtual business was what I wanted to do. And I started a real estate support virtual business because I knew real estate and real estate knew me. There were a lot of people in my area that knew me and I was able to bring on clients pretty quickly. Then I had an opportunity to coach with a virtual expert training program, and part of the lesson is they have to select a niche for their virtual business. And I would get to that lesson with them and I would be emphatic, you know, you've got to do something you love, not something you know how to do. Do something that you really love. And that's One day I had to say, well, why are you so emphatic about this lesson in particular? And it dawned on me that I wasn't loving what I was doing and I needed to make a change. And that's when I looked at, you know, all my skills, all my desires, what I was, what I did like doing in the business that I had, and that was blogging and writing social media content for realtors. So that's when I decided to make the switch.
Okay, love it. I love the, the whole niche. And it's interesting that doors open up when you were looking, and then it kind of all fell into pieces. I— bear with me for one second. I want to make sure I don't have some— nope, I don't. Okay, as you, you're coming a little, um, crackly, so I just wanted to see if it was high end. That's okay. All right, so Oh, I'm on Toastmasters. I'm not supposed to say so, so let's rewind that. Take it back. I didn't use a filler word. So, oh, see, it comes out then when you start to do it. Wow, so many changes taking place in content and being like a copywriter. So tell me, like, at what point did you realize, oh, things are changing right now with the chat AI. Well, I should just say AI. Um, what did you— did you have, like, were you questioning what that would look like, or did you just say strong, you know, the content I create is my content and I'm proud of it?
No, I, I, I actually use AI in my business. Um, I use it as an idea generator, um, help me outline things, um, when you just get stuck and you can't— like, writer's block really isn't a thing anymore because I can say, you know, this is what I want to do, give me some ideas, and it It's like having a partner in my office with me who can brainstorm. So I love that. I haven't been afraid of it. I love new things, so I was ready to jump into it and I found a way to use it in my business that is very helpful.
You know, it's so funny because when I first heard of ChatGPT, my first thought was to try it and then I fell in love with it and then I questioned why I wasn't as familiar as I should have been when other people were like, well, I've been using it forever. And I never put two and two together, like the chat, like in, you know, GoDaddy or in a website where you have the chat box. And that's part of AI. So, but I agree with you not to be afraid of it and to use it because it can only enhance. It's still coming from you.
Right, right.
It's still your copy. So, Cindy, where are you located?
I am in Pennsylvania. I'm in northwestern Pennsylvania. Almost halfway between Pittsburgh and Erie.
And so explain to us, because I, you know, I guess I would say I'm a copywriter too. I am a podcast producer, so I write the show notes, the socials, all of that, you know, put everything in. I use a system, but I also have to review everything and read a lot of mistakes. But I don't— and I write my own blogs and articles and all of that. So I, I guess I could say I am, but I'm not sure. So tell us What really makes someone a copywriter? And if you know you are and you're good at it, how do you help them to actually develop a career around it?
I don't know. I think I find for me, I love the storytelling aspect of it. So no matter what I'm writing, it's a story and you got to connect with your clients. So being able to And coming from the real estate world, this is very hard, is to just put yourself aside and put your client first. So you want to talk about your client's problems, not how great you are. So, um, I think if you have that ability to, to look at the client and focus on the client, everything from the client's aspect, I think you're you're going to be a good copywriter.
Sydney, everyone out there, I don't know if you heard what Sydney had to say, but this is really important because— and Sydney, I want to just kind of like spread that out a little bit more too, because what I've noticed with other consultants, what— so whatever that position is, I want to say when you're a consultant, it's not about you. The time that you're spending with your client, they're paying for that time. So don't talk about yourself. Don't talk— you know, you have to really keep it in the straight and narrow, right, about what it is that you could do for your client or what you're doing or whatever your accountability. And I know too many times, even myself, when I go to look at someone for myself as a coach or consultant, I'm like, oh, if you're always talking about yourself, where, where do I fall in? So I think that's amazing advice. Yeah. And not many people talk about that.
Yeah. I, um, you know, it was a— there was a lot of it in the real estate world where I came from, and I always felt like, well, you know, it's great that you are a multi-million dollar producer, but the people that you're trying to attract don't understand what that means. And, you know, did you make a million dollars? No, you sold enough houses that accumulated, you sales prices accumulated to $1 million. So it's unclear messaging and it doesn't tell the client what you're going to do for them.
Plus, I mean, if you're a realtor and you're so busy selling homes, I think that we have to remember that, you know, hire the right people. So if you're going to talk to— it's not like you're going to sell a home and say, Cindy, you should buy this home and you can easily put up— go to YouTube and you can find out how to install a new roof. It'll be easy for you. Like, that's not how it is, right? But that's how people think. So So I think that's really important. Now, is your niche still realtors or have you expanded?
I have expanded. I like writing for entrepreneurs, small business owners. One of the services that I provide that I get the most reward out of is helping to write LinkedIn profiles, especially for entrepreneurs, because I think their story needs to be part of that. Not, I mean, I don't believe in redoing your website on your LinkedIn profile. I want, you want people to be able to relate with you. And I've had the opportunity to work with a LinkedIn strategist working with her clients. She found that her clients didn't want, didn't do a good job of writing their own profile. Writing about yourself is very hard. So, you know, I get— I interview them just like we're doing here. I get to find out a lot about them, and usually there's some story in there that makes them unique, and that's what I like finding and bringing to their profile. It's not easy with the limited characters we have there, but watching somebody just read their profile that I wrote for them and see their— was that really me? Is amazing.
I love that. So Cindy and I do some similar things, which is great because we can't, we can't help everyone with their LinkedIn, right? Cindy, what I know— so I, my niche market is the promotional products, the logo merchandise business. That's what I grew up in. And so I'm surprised how many in our marketing and branding industry don't understand the importance of having their LinkedIn be awesome on like showing, showcasing branding and marketing. And I think it's like the cobbler's daughter who never had the shoes. It's kind of the same thing. So I'm always telling, um, our industry, my niche, which is that niche, to— that they really need to work on it. And I have a lot of clients I do very similar to you. But what I do also show, and I'm curious if you do this too, when I'm working with my clients, I show them the reason why, not just you know, someone finds it. But every time you make a post or you make a comment or you connect with someone, all they see are those lines. And so it surprises me sometimes that someone will have, like, in our industry, some of them are branding experts, will just have, you know, mother to 3 kids or something that doesn't really say, like, yes, you should put your company name in your profile if you can, because if you are a marketing executive, at where. That is important because people are only seeing 3 lines. So I— there's a lot of times where you really want to know who do they work for and should go in. So I love what you do, and I think that, um— oh yes, you and I were talking because I want to do, um, I want to do a social audio room on LinkedIn. And so I was wondering if you would be interested. It hasn't come out yet, but it's, uh, 3 guys in Clubhouse that are taking social audio like Clubhouse, Twitter Spaces, LinkedIn, and kind of, you know, creating something a lot bigger with videos. Hopefully it all works out for them. They're a little delayed. That's what happens. But I think it's important to get another voice, like more voices, because we all— we used to all get on together. All us LinkedIn experts would get on together and do rooms because it was fun to hear each of us also have different, you know, some of us like you and I are in our clients' accounts, right? Like you're, you're it. And then some people are actually not in the account, so they don't really see. Like, okay, let's talk about a couple things. One is I have clients that don't have Premium, don't have Sales Navigator, but still have— yes, Chatter! Thank you. Yes, I'm very excited about Chatter. The, the three— so, okay, so let me go back because I just got, I got excited about chatter for a second. So hold that for one second, let me get my brain together. Okay, so we are— so I know I still lost it. It's like not coming to the tip of my mind. What? Thanks for putting in chatter, but you, you took my chatter away. Oh my gosh, I can't believe it's my husband's birthday. So I'm probably just excited that it's his birthday.
Mine was yesterday. Happy birthday to your husband.
So all of us have different ideas, but put together, it's really interesting to hear. And so I have clients that don't have premium, don't have Sales Navigator, but they get 300 characters. And then I have some that don't have anything. They're limited to 100 characters. Then I have some that have premium and I can do a lot of lead generation for them. And then I have some that don't have Sales Navigator Premium. No, you're fine. But I'm able to actually do the work for them. So it's crazy how people— unless you're in it, right, that you— there's so many different things. Tell me what you find when you're in your clients' LinkedIn and what you see that's not across the board.
I generally don't go into their accounts. You know, I leave the, the copy and pasting to them. If I'm writing content, I usually will schedule that in a third-party scheduler still working on LinkedIn. So for now, we'll see. But, um, no, I'm a little cautious about going into somebody's accounts, just the strategist that I work with.
Oh, maybe I should know why. Is there something I should know?
I guess some people have been shut down by having third parties into their accounts, um, and I think that's some of the big companies that are out there writing, you know, interest.
I've been doing it for 3 years and probably maybe 100 accounts and never had an issue. So I've been also getting, um, doing LinkedIn events is really big too. I had a client that did a great LinkedIn event, so that's something for, uh, for other people too. You're doing the content, but they want more, more visibility, so LinkedIn events are fantastic. Tell me about where your cup of coffee came in. Like, what was— what were you drinking? A cup of coffee? What happened that made you come up with that?
Well, I always— I was always posting a lot of coffee memes on Facebook and, you know, making coffee jokes. And my business coach said, you know, you really should go with that coffee thing because that's how we identify you. And I thought, well, it could be fun. And, you know, I— when I was coming up with my name, I went back and forth and back and forth. Should I do something clever or should I sound more professional. And, you know, coming from the real estate industry, it was all about being professional. And I thought, no, I gotta show that I'm creative. And Your Cup of Copy is a creative name, as opposed to your copywriting, whatever it would have been. I don't know.
It's such a creative name because you got the creativity, but you know right away what you do. So it's like really almost it's at that level of perfection. But how do you protect yourself? So do you have you trademarked it?
I have not.
You should.
There are some similar names out there.
Don't even— we'll sic our attorneys on you if you think we'll have— well, I'll show this recording and you will be put into jail. I'm serious. No, it's so fantastic. And how does someone work with you? Like, what does that look like? They go to your LinkedIn profile?
You can go to my LinkedIn profile or my website, which is yourcupofcoffee.com.
What is it?
Yourcupofcoffee.com.
Amazing. I love it so much. I mean, I think to me that's like one reason just to work with you. If you're creative and you're creative enough to come up with a name like that, your copy has to be creative.
Well, I love using humor in my copy as well. So anybody that likes to have some fun content, we'll have fun working together. I write for the— for a business coach that she was my coach and now I write some her LinkedIn content and she's very witty and she is an oversharer to a degree you probably haven't seen yet. But she lets— but I tried to take one of her stories a week and write a personal, um, story and relate it to how— what she teaches in her business. So it's a lot of fun.
I love this. It'll be fun to actually— we really need to do the Chatter together. I'm gonna send you the link so you can do the test if you have time and you like to like test new apps and stuff and see. I've been on Clubhouse for about 4 years, so I've seen these guys grow. They're fun. They do a debate style, um, program. But I would love for you to sell me and our audience on why newsletters from LinkedIn— or don't sell it, say no, don't do a newsletter LinkedIn. I would love to hear more on your thoughts on the newsletter side of LinkedIn.
Well, newsletters are an awesome way to stay in touch with your clients. And, you know, you can not only do the newsletter on LinkedIn, but you can use the same content as an email newsletter to your database. So, you know, repurpose that content as much as you can. I, I am a big fan. I write it. I usually share blog posts. Like, I had a package for a client where I would write a blog post for her that we would first post on LinkedIn. It was written in a way that I could split it into two separate blogs. So we would then every other week put a blog on her webpage and then her, her team took the blog and created social posts out of it. So it was a nice— and then I would write some emails for her. So every time the blog got posted, we sent an email directing people to her blog.
That's the way to do it. I love that.
So you can really use that same content all over the place.
I get that a lot, you know. Well, I don't have content, and then I go on their website, I'm like, wait, you have all this content. People are— people don't understand that when you're going on to someone's website, like, okay, in all honesty, for me, I dig. When I'm interested, I will dig around and go around, and even if things open another window, I'll do all of that. But I think the average person isn't like me. They're going in for a second. So the more, the more you can like take the articles and bring it into LinkedIn and then bring it back, it makes sense.
Yeah. Yeah. And I think that so often what we do, we think everybody knows how to do because we know how to do it. So everyone must. So we don't even realize how much we know. And other people don't know. And sharing the basic stuff is just as important as sharing the more complicated things. So true.
I was a coach. I did a live coaching call, and he called me. He told me that I have an addiction to being— I have an addiction to input, and that I need input all the time. And, and I was like, oh my God, he's right. Like, I'm always having to listen to a podcast or listen to the news or listen to Clubhouse. That'll be chatter. Like, I always have to have information coming into my brain. And I thought, well, that's just so weird. But I, I think that it really is important to remember that people don't know what they don't know. And so as often as we can teach them, it's so important. All right, I'm going to ask a question.
I'm going to whisper it because I don't want LinkedIn to hear.
What do you think about Alignable?
Same, same strategies work there. I think that worked on LinkedIn.
Are you doing it for your clients? Are you touching Alignable?
Not really. I've been, I've been using it myself a little more and just realized this morning I hadn't been on it in a while.
Someone send you an invite?
No, I just, I just was looking at my LinkedIn. I was working in LinkedIn this morning and I thought, Oh my gosh, I haven't been on Alignable. I forgot all about it.
Wasn't there a point in time where Alignable cost money and LinkedIn was free? So at that time, it didn't make sense for me to put my energy into Alignable. But now I actually don't even know if Alignable and LinkedIn are on the same page. You know, I don't know if like with costs.
I don't know either. But I know that, you know, what you do on LinkedIn, you could do on Alignable as well.
So it's another location where you could actually get your information out, and that does not hurt. And I'm sure Alignable probably has good SEO because that's the thing I tell people. You want to, if you have a business, create the company page, it's free. And LinkedIn's SEO is going to be a lot stronger than probably your SEO. So the first thing, right, is you Google your client and say, oh, look at your LinkedIn popped up. That's why most people are like shocked with that.
Yeah, Google anybody and LinkedIn's going to be in those top results somewhere.
Isn't it? It's so crazy to me. Do you also get this? I get this a lot. Clients, I don't like LinkedIn. I will never use it, but I need it. People are telling me I need it. So blah, blah, blah, blah, blah. And then like 3 months later, I'm like, are you ready to let me go? Because I do— how I do is I let my clients— I try to call them like fly. So like I do a program for them, I get them to do it. But then I notice at one point they're like, they're doing it. I'm like, yay, that's what I want you to do it and get the joy of doing it. And then they go off and I always have another client coming in. So do you feel the same way?
Yeah, I think that I know in like 2008 or 2009 when I was working in real estate, we were told to start a LinkedIn profile. It was necessary, but we really didn't know what it was yet. And I had a LinkedIn profile for a long time and never did any— as a real estate agent, I didn't do anything with it. So I think now real estate agents need to pay attention to it because they're going to have to prove their value a little more than they used to, just because of the NAR settlement, proposed settlement, and, you know, all that's the talk out there about commissions. And so it's a great place to prove who you are, and I think it's a great place to find your ideal clients too, and referral partners.
Um, so yeah, makes you credible. Yeah, but realtors have a hard time because it's not like they can find like someone who's actually looking to buy a home So, but they can find business owners or human resources of large companies that are bringing people in and looking to move.
Like, that would be probably other agents in other areas who are, who can send referrals back and forth.
Yeah, I think that's the best part. I love is trying to figure out, okay, who is, because I always say you're not going to find a 61-year-old chunky brunette with glasses on LinkedIn because that's me. And you have to know my name, and that's the only way to figure it out. I love, I love speaking to other LinkedIn experts. I hope you think about Chatter, or we could do LinkedIn audio events. I think that's important to teach people, get them a chance to be on stage, get them a chance to ask their questions, maybe do some live LinkedIn profiles, which is fun. And it's always fun not doing it alone. It's not fun doing it alone. It's more fun, you know, having a team around you. So I would love to co-host with you. I'm putting this out to the universe, Cindy. I knew right away. I did a little peek, but not much when I said no prep needed. A little peeky peek. I'm trying to think, is there anything else that you want to share? We've got your website. We've got what you do. We've got how to reach you. Anything else that I missed?
I don't think so.
I'm just here for the— I do have that question. Are you using a CRM?
I am not.
No, I'm only asking because I started to use Keep and it's made such a big difference because it allows me to automate so that I actually can automate and say, can you give me a referral? Can you give me a review? Um, you know, it allows me to put everything in one spot and then I could do what's called, uh, landing pages, which I absolutely love. So it just gives me a more of a way of of understanding. So maybe something you'd be interested in.
Well, I use, I started using MailerLite, which I guess is my CRM right now. Coming from real estate, I think of CRM as something much more robust.
Yeah, I think of it that, well, you can place orders, but I always just bring it up because I absolutely thrilled that I have it now and it does make a difference in your business. So anything else that you would say about someone who says, I don't need LinkedIn, I am an insurance agent and I'll never find my people on LinkedIn?
Let's talk. I just wrote a profile for an insurance, a Medicare insurance agent. So, and she knows that's where she needs to be. Somebody that she works with got a speaking opportunity through her LinkedIn profile. So they're important.
It really is. And I absolutely love, um, you know, being able to look at someone. So actually, just before I let you go, I will tell you I'm a trusted house sitter. So I sit for people's pets for free and travel, and it's a program. We're insured and background checks and all of that. I actually get most of my sits, like 98%, because they find me on LinkedIn, or I send them my LinkedIn and they see immediately I'm credible and that it's on my website. So there's even more things that are not business related, but just fun, like being a trusted house sitter. Yeah.
And I don't— before people talk to you, they're gonna, they're gonna Google you. And that's one of the things that comes up. So exactly.
Oh, so nice to meet you, Cindy. Thank you so much. So just to be clear, so this interview, I actually take it it's live now. Thank you for not saying anything. Thank you for not doing any. Okay, but, but no, thank you. And then I'll turn this into an actual podcast that'll be on the different— I still haven't figured out my way to get into Apple. I gotta do that one. But everything else, uh, iHeartRadio, Spotify, we go on. You're amazing. I'm gonna touch base with you after the fact. And I— and how did you celebrate your birthday?
Um, I watched my grandchildren on Thursday, so I spent it with a 5-year-old and a 2-and-a-half-year-old.
And that is just so fun. I love that. I love being a grandma too.
Yeah, yeah, it's the best.
Yep. Uh, wait, so where do you live again? I'm sorry, or where do you—
Pennsylvania, Northwest.
Okay, I'm a Connecticut girl, so maybe that's why the— our— us New Englanders, we're kind of similar.
My husband's from Connecticut.
Where?
Torrington.
Oh, I love Torrington. Does he ever visit? Does he have family?
Yeah, his sisters and his brothers in Torrington, his sisters in Harwinton.
Wow. So in Cheshire, Connecticut, on Route 10, is my parents. They both passed, but their legacy was left, and it's called the Barker Cartoon Character and Comic Museum. It's a toy museum, barkermuseum.com. So if they're ever in the area, they should stop in to see the museum. And it's all— it's the, the one of the first toys on through with a history, 80 So, oh wow, that's exciting. Thank you. Yeah, and then we have the Barker Animation Art Gallery, um, in Cheshire and also at Tanger Outlets, which I just like to bring up. So always fun when someone's in Connecticut. All right, so thank you so much. Have a great rest of the day, and I look forward to connecting with you because I really want to see if you would be interested in being, uh, co-moderator with me on Chatter.
Absolutely.
So thank you.
Thank you.
Bye-bye, everyone. Give Cindy business. Bye-bye.










