Bold Branding & Authentic Leadership: How to Build an Unforgettable Brand with Judy Winslow

What does it really take to build a brand that turns heads and leads with impact?

In this inspiring episode, Deanna sits down with brand strategist and business mentor Judy Winslow to explore how embracing what makes you different is the secret to building an unforgettable brand. Judy shares her deeply personal journey from feeling like she didn’t fit in to becoming a powerhouse in brand leadership—and how you can do the same.

You’ll learn:

• Why trying to “fit in” holds your brand back
• How to uncover your unique strengths and brand DNA
• Simple assessments and exercises to define your personal brand
• How leadership is already part of who you are—and how to own it
• The one mindset shift that unlocks personal and professional growth
  
  

If you’re in the early stages of building your business or redefining your brand, this episode will give you the clarity, confidence, and tools to stand out your way. No cookie-cutter formulas—just bold, strategic authenticity.

✨ Plus: Judy’s brilliant “Power of Two” exercise and how to create your own brand MAP (Motivated Action Plan)!

Connect with Judy Winslow: 

Website: unforgettablebrands.com

Social Media Links: 

https://www.facebook.com/judywins

https://www.linkedin.com/in/judywins/

https://www.instagram.com/jWInsCEOpro

Chapters

• 5:22 You Are a Walking, Talking Brand
• 7:44 The Struggle to Fit In vs. The Power of Standing Out
• 10:07 How to Start Building an Unforgettable Brand
• 13:40 Two Exercises to Clarify Your Brand Voice
• 16:28 Why Comparison Kills Authentic Branding
• 19:16 Redefining Leadership (It’s Not What You Think)
• 22:01 Branding as a Strategy for Leadership Growth
• 24:47 The #1 Branding Mistake Entrepreneurs Make

Transcript

[00:00:01.120] - Deanna Hinsz

Have you ever felt like you had to shrink yourself just to fit in, just to belong in business or life? Well, today's guest is here to lovingly shake that mindset up and help you see that standing out is your greatest asset. Judy Winslow is a powerhouse in brand strategy and leadership. She's the founder of Unforgettable Brands where she helps leaders build brands with sole and teams that grow personally and professionally. With over 30 years of experience, including co founding a marketing firm in New York City and working with major Madison Avenue brands, she brings next level expertise paired with heart. Judy's work has been featured in Market Insider, Yahoo Business, ABC, and even Small Smile Jamaica TV. She's a TEDx curator, an international best selling author, and a Canfield Success Principles trainer. But what makes her truly unforgettable? She believes that your brand is not your logo on your website. It's how you show up. It's your leadership. It's the special sauce only you can bring. In today's episode, we're diving deep into the value of being different, why fitting in is not a recipe for success, and how your greatest brand asset might actually be the very thing you've been trying to hide.

[00:01:30.560] - Deanna Hinsz

Get ready for some serious insight, soul and strategy. Welcome to she Is Unstoppable, the podcast for ambitious women ready to break free from the 9 to 5 and build a life and business they love. I'm your host, Deanna Hins, digital marketing strategist, entrepreneur, mentor and a woman who took the leap from corporate life to full time entrepreneurship and never looked back. I've been where you are and now I'm passionate about showing you how to build and scale a business that works for you. In each episode we dive into actionable tips, inspiring stories, and real strategies to help you grow your business, boost your confidence and create create unstoppable momentum. Whether you're just starting out or ready to elevate to the next level, you're in the right place. Let's get started.

[00:02:25.550] - Deanna Hinsz

Judy, thank you so much for being here today. I am so excited to talk to you just about branding and being bold and standing out and just making your brand unstoppable. I love it. So thank you so much for taking the time and coming onto the show today.

[00:02:44.720] - Judy Winslow

Thanks for having me. I'm thrilled to be here.

[00:02:47.840] - Deanna Hinsz

Oh, wonderful, Wonderful. This is going to be so good. So first off, before we start getting into exactly what personal brands or small businesses can do to make their brands stand out, I want to find out a little bit about you. How did you get into branding.

[00:03:07.110] - Judy Winslow

Mm. I would like to say it was highly intentional, but it wasn't. It was. It's sort of like the universe shows your path and sometimes we are. Oh, I don't want to even say smart enough. Sometimes we sort of fall into it and sometimes we resist it, but it usually comes back around in some manner. So I was the kid that did not. Well, I still am the kid that didn't fit in, but when you're young, it was so torturous. Like, it was. I was dark and depressed and suicidal. It was bad. And all I wanted to really do was like, be like everyone else. And that's really never worked out for me. Now I'm thrilled and delighted that that is the case, but as a kid, it was absolute torture. You know, there's something about our culture and the programming that, you know, we value this whole fitting in thing, which is so goofy because we spend so much of our lives trying to fit in and then we're kind of kicked out of the nest and told, you know, go, do you? When we don't even really have access to, like, what is that?

[00:04:21.670] - Judy Winslow

Who is that? Where do I find that? So that's kind of how I got started. I was a visual designer who. I wanted to specialize in logos and brand identity. And my teachers told me that that wasn't a thing. So this was way back, way in the bar, in the dark ages. So I went home and found this company, which still exists in London, which is a huge, very multinational design firm, and that's what they specialize in. And I went back to school and I went, well, these guys are doing it, so I'm doing it too. And that's really how I got into branding back in the day when people only thought branding was for like Coca Cola and the Marlboro man at the time, which is kind of funny. Now we have languaging. Yeah. So people would say, I'm a small business, what do I need that for? I'm a human. What do I need that for? But we are all a walking, talking brand all the time. We just don't realize it.

[00:05:22.080] - Deanna Hinsz

You know what, you're right. We don't realize it. But explain what that means. That we are all a walking, talking brand and we don't realize it. How are we a brand?

[00:05:31.130] - Judy Winslow

I mostly work with founders and leaders and C level type people. And it's so interesting to me that, well, you and I talked, just touched on it briefly, that we so often don't even have access to what makes us special. What makes us different? What makes us us? Like what? Like, I was just speaking to someone and I said, you know, I just recently found out, like, in the last year that your fingerprint is formed in the womb, and it's one of the first things on a human that is created. I did not know that. So I always talk about, like, you have this very unique fingerprint, but you. You really do. Like, no kidding. And literally so, the way that you see the world, the way that you perceive, the way that you problem solve, the way that you imagine and identify and create and lean into your unique gifts, those are all very important brand elements that most people either ignore. We don't value, we don't leverage, we don't monetize. We don't even, like, we don't embrace on the level that would allow us all to be lifted, because really, that's why we're here.

[00:06:46.630] - Judy Winslow

Right? I think so. Is to lift one another and become stronger and better together. So you can't do that if you can't access your own fabulosity.

[00:06:57.250] - Deanna Hinsz

You know it.

[00:06:58.040] - Deanna Hinsz

And you make it sound super easy. Right. And it's harder, I think, to do that sometimes. I remember when you were talking about when you were a kid and, you know, you just wanted to be like everybody else. You wanted, you know, to fit in. And it's. It's interesting. My name is Deanna, and when I was growing up, you did not hear that name anywhere. So when we would go, like, on field trips, you could never find. I couldn't find the pens or the keychains or anything with my name on it. And I hated my name because it was so different. People misspelled it. I couldn't find. Was just so frustrating. And I remember feeling like, why can't I just have a. A normal name like everybody else? And. And it's really not that different. But as a kid, it felt so, so different. And I just wanted to fit in. And I don't think that it was until I was older that I was. I liked that my name was not like everybody else. Yeah. People. A lot of people only knew one. Deanna.

[00:08:01.940] - Judy Winslow

Yeah. And so funny. It's so funny because we. So there's this level of like, that's just cultural that we're programmed to fit in. Right. We're supposed to have a buddy and you're supposed to hold my hand when you cross and all this stuff. And then as we get older, like, for me, the real awareness was when I started working and I was sitting in a meeting with all these muckety mucks, and I was teaching them. Basically, what I was sharing was the value of not fitting in. Because that's what great brands do, right? They have the audacity to stand out, but so few are really willing to even investigate that, much less own it. And so a lot of my work is around accessing that and owning it. And part of the reason that it is hard is because we can't see that for ourselves. We need that reflection. We need somebody to say, hey, did you know that I can't do that? Like, what you do is so unique and special. And then the way you take this and combine it with that and make this peanut butter cup. Wow, that's amazing. Why aren't we sharing that with the world and using that as your platform, your process, your widget?

[00:09:11.500] - Judy Winslow

Like, why aren't you using that to kind of stand out, be different, and then allow yourself to be separate from the pack? Because being in the pack is not. It's not where the joy is, it's not where the fun is, it's not where the juice is for living a fulfilled, full life. And that's what a brand isn't like a logo. That's just one element. It's like you're a diamond. You don't have a diamond doesn't have one facet. The more facets, the better. Well, you don't just polish one facet, you're going to polish the whole bloody thing.

[00:09:47.770] - Deanna Hinsz

Absolutely, yes. That's so true. It's so true. But if somebody's listening right now and they're like, okay, it does make sense. But how. How do I create that brand? How do I create a brand that stands out? What do I look at? What do I look for?

[00:10:07.850] - Judy Winslow

So the first thing is to really start with assessing your assets. So we. It's so cool because these days we have so many cool tools to do that, and I love that. So I'm a big fan of assessments, but I like funky assessments. So Gallup strengths is one. Like, my first Gallup Strength is strategic. So I'm someone that, when I call it pushing off, like when you push off from shore and you're on a boat, what are you pushing off with? So I go to strategy, because that's how I. That's how I process life. But then you can also access all these other things. That's why people are so into human design and enneagrams and astrology and all the things, because those give us tools to understand our inner self better. It doesn't Start out there. It's not an external process, it's an internal assessment. And once you have those, you can assess. Just like in a business, you would figure out your numbers and your costs and your revenue and your talent. You're above the line and below, you know, all the things that we're going to do the same thing with your abilities and your fabulosity and your inherent qualities.

[00:11:18.740] - Judy Winslow

So we know how to create that peanut butter cup that makes you tasty, delicious and unresistable.

[00:11:26.760] - Deanna Hinsz

Yeah, I love it. I love it. So, so once you figure it out, then what do you do with that?

[00:11:33.970] - Judy Winslow

Well, it kind of depends. So it depends on, you know, are we talking about scaling your business? Are we talking about.

[00:11:40.820] - Deanna Hinsz

Yeah, let's talk about. Let's assume that it is. Most of my audience are women entrepreneurs.

[00:11:48.260] - Judy Winslow

Okay.

[00:11:48.880] - Deanna Hinsz

And they're just starting out their business. So they're in that early stage and probably figuring out who they are right now. Yeah, they might finding out who they are and really getting clear, working on, getting clear on who their ICA is, what they want their brand voice to be right through that early stage.

[00:12:09.170] - Judy Winslow

Right.

[00:12:09.670] - Deanna Hinsz

So they've heard, you know, take this strengths test, the strategic, any of the strategic tests. Right. I like strengths. I know offline, we were talking a little bit. You're a big strengths fan too, and you identify what makes you unique and different. But then how do you incorporate that into your business or yourself?

[00:12:31.690] - Judy Winslow

So there's again, the first part is like data collection. Right. So first of all, we want to know what your strengths are. We want to know. You know, when I first started this, we didn't have some of the verbiage that we have today. So I wouldn't say like, what are your values? Because people would be like, what? I would ask people what's important to you? And when we know about your business, what do you want us to think when we think about Diana Heinz? Right. Like, we want to think about what's the perception? What are people thinking? How are we using this? And one fun way to do it. Well, there's a couple that are super easy and reveal a lot. So one is to make a little short list of like three to five companies that you admire. Three to five businesses, three to five humans. Like, is it Steve Jobs? Is it Disney? Is it? Who is it? And then list some of the attributes that you think are amazing about them and that's why you admire them. And once you start that list, you can then see, oh, are these attributes that I also own or are they Attributes I would like to own.

[00:13:40.200] - Judy Winslow

Like, what in here is a piece of meat? Because sometimes when we look at ourselves, we come up with nothing like, you know, negative.

[00:13:50.260] - Deanna Hinsz

We don't see the good stuff sometimes.

[00:13:51.730] - Judy Winslow

Right. I know it's special. What are you talking about? But when we start to look at. Okay, I really like this brand. It's reliable, it's beautiful, it's consistent. I understand the message. I relate to its leadership. I love the product, whatever it is. Right. I like their campaigns. I think their spokespeople are amazing. Why? Just keep asking why? Be curious. So that's one way to get. Really start to dig into these assets that will then translate into your content, your marketing, your copy, your outreach. You'll start to see how these dots connect. And then another fun exercise is to. I call it the power of two. So you'll ask in writing. Because we don't want to rely on what we hear, because we often interpret what we hear. So it's like when we see color, I'm wearing gray. But what you might see as this gray could be completely different than what I am perceiving. That's why we have the Pantone matching system. That's why we have paint chips. So we can agree that we're seeing the same thing. So we want to do this in writing. And you're going to ask two friends, two colleagues, two clients, two vendors, and two family members, what do they see as your top attributes?

[00:15:10.720] - Judy Winslow

What do they think is fabulous about you? Because everyone that interacts with you in a different manner will have a different response, or some of them will be similar, and you'll see the commonalities, and you'll start to see how the world views you, which may not line up with how you view you.

[00:15:28.640] - Deanna Hinsz

Yeah.

[00:15:29.180] - Judy Winslow

Which is awesome.

[00:15:29.850] - Deanna Hinsz

That's so interesting. Both of those. I'm like, oh, I might try, actually, both of those things you just shared. Because I've never done either one of those. And I see the value and the information that you get from both of them. I mean, oh, my gosh, it's like, why didn't I ever think of doing this?

[00:15:47.970] - Judy Winslow

There's a lot. Yeah. And so that's what's really cool about branding. So, yes, it can be really challenging to see it for yourself, and that's why it's awesome to have people like me to help lead you through it and then see how to apply it and then step into this bolder version of you. But the same thing is true with whatever it is that you offer. But the thing about it is that it can also be very easy and very fun and very systematic. Really. There's a lot of ways to kind of get to the information that are really enjoyable and not, like, super painful, that people think it's very like, oh, this is going to hurt. No, no, it's going to be fun.

[00:16:27.500] - Deanna Hinsz

Do you find that sometimes people are afraid to step into that because there's a fear of being judged or that they. They're looking at maybe another business or another personal brand that they like and respect, and they're doing it this way, so they feel like they need to do it that way as well and not take your advice and step out into their own personal brand. Do you see that?

[00:16:56.950] - Judy Winslow

So one of my little. I call them isms. Like mine are Judy isms. Get it? Oh, I love it. Is that fitting in is not a recipe for success. So one of the things that happens when we. I find. This is what I find happens a lot often is when we start a business, we're just like, yippee. This is so amazing. I'm gonna rock the world. I feel it. I feel it, right? And you just lean into it, and your passion and your enthusiasm kind of fueled the ride. And then at a point, things sort of flatten out or they kind of get a little bit wonky. And that's when we lift our head and we start looking around like, oh, crap, you know, like, what am I doing wrong? Right? That's our first internal question, right? What am I doing wrong? So we start looking at other people and other businesses and think, oh, well, they must know better. And that. I get super crazy over that, because what works for one person? And then the gurus who are like, do it this way because I did it this way, and I'm a gazillionaire.

[00:17:57.170] - Judy Winslow

And it's like, no, dude, that's your formula for success. That's not my formula for success. Part of the journey is figuring out your formula, your recipe for success. You don't go on the show Chopped where they give you a basket of goodies and we don't all make the same bloody dish.

[00:18:14.910] - Deanna Hinsz

That's true.

[00:18:15.710] - Judy Winslow

We have our pantry of fabulosity and our own personal ingredient list, and we are cooking up something amazing every day. But we have to be curious. You know, when you use your curiosity and your creativity and your business smarts, that's where we start to uncover your own formula. But you have to lean into it and be curious and kind of stop looking at other people for their success story and be Committed to writing your own.

[00:18:49.490] - Deanna Hinsz

You know, when you said that we all get to, like, have the same ingredients, but we create something different, and I'm like, yeah, we absolutely do. And that's okay. Like, that's good that you want to be. So when you do this, when you start taking all this information, utilizing these tips that you gave us, we start to stand out as a leader. Correct?

[00:19:16.560] - Judy Winslow

Well, you know, leadership is an interesting journey, and I think the first piece of it is, are you willing to own that you have the capacity and. Or are already a leader? So to me, a leader is not somebody who is at the top of the mountain looking down on their subjects. A leader is pretty much, well, I think we're all leaders and that we've been lied to, that there is this, like, holy mound where the leaders live. But if you are leading your dog across the street, your family to dinner, you know, your little sister to be a better person, your marriage to flourish as well as your business, those are all examples and illustrations of leadership. It's not just confined to the business space and people who make lots of money and drive a Ferrari. That's such bullshit.

[00:20:09.950] - Deanna Hinsz

I love that you're so right.

[00:20:12.490] - Judy Winslow

Right. We have to say, well, okay, what's my version of success? How do I define a fulfilled life? What do I call leadership? And then lean into learning about it. Lean into the not. You know, now we know so much about energy and working with the field. Like, stuff that was considered woo woo wacko just a minute ago. And now it's like, it's common knowledge. We know that it's a thing. Like, there's so many cool things in the world right now that feed into this awareness that we are all leaders and that it's time for us to take up that baton and run with it. Instead of cowering and pretending that life is happening to us, rather than we are actually impacting the field, we're impacting our communities, we're impacting our neighborhoods. And really, you know, like, be an active participant instead of this. Instead of being. I don't want to call it victims, but sort of at the mercy of it, rather than. And it doesn't start, like a huge thing. It might just start with what you're eating or who. Who are the five people you surround yourself with or, you know, Marty Seligman talks about in his book Flourish, he's got this formula called perma.

[00:21:33.850] - Judy Winslow

And the first one is like, how are you? P is for positive engagement. How are you bringing positivity to the world? Because any of Us can bitch and moan and complain and trauma share, but it's. It's this invitation to do something else, to do something different, and to start looking for opportunities where your gifts and leadership will be valued and amplified.

[00:22:01.190] - Deanna Hinsz

So how can you. Can you use your brand to show this leadership and combine the two?

[00:22:09.110] - Judy Winslow

Well, not only can you. You already are. So it's really, you know, owning that awareness. So I have a little formula. I call it ask. And the first one is, we've already talked about it. It's around. It's like, what are your assets? How can you. You want to gather all your assets, all the data, like, get really clear what you're working with. Right. Like, what's the clay that you're going to be forming this wonderful sculpture? But then the next thing is now you have this awareness. And how do you want to use that awareness? Well, you want to design a strategy. We're always in the process. It's one of the reasons that I love this. This connection point between branding and. I don't do visual branding anymore. I'm much more in the strategic consulting arena and business advisory. So how do you take this? Connect all the dots so that now we are forming some sort of a strategy? Well, first you got to know where you going. So what's your end game? Do you want to. You want to go from Florida to California? Well, you're going to probably want a map, right? I call a map a motivated action plan.

[00:23:18.700] - Judy Winslow

So how do you plan to get there? That's your strategy? Maybe you don't know. Maybe you just know how to get from Florida, South Florida to North Florida. Maybe that's as far as you got. Okay, awesome. So let's get there, and then we can assess and start again. And it's an ongoing process. We evolve. I never thought I would be this person I am today. I didn't consciously say, like, oh, and I grew up. No, I mean, if you told me I'd be, like, teaching and training and living in Florida, and I would just think you were high. Like, that's just. That was whack, you know, like, life evolves, and we evolve with it, and part of it is just really leaning into those breadcrumbs and seeing what's there.

[00:24:00.570] - Deanna Hinsz

Yeah, yeah.

[00:24:02.050] - Judy Winslow

You start where you are.

[00:24:03.130] - Deanna Hinsz

I like how you shared about the map. And when it comes to branding that, you know, yes, there's that visual aspect of it, but there's also that strategic behind it of figuring out where do you want to go?

[00:24:17.590] - Deanna Hinsz

Right.

[00:24:18.020] - Deanna Hinsz

So let's.

[00:24:18.580] - Judy Winslow

Not everyone wants to serve, you know, health professionals. Not everyone wants to serve attorneys. Not everyone wants to serve engineers. That's great. That's why we have all these flavors. Right? Figure out what's your flavor, and then where will you be valued and honored and can apply your secret sauce so that other people are lifted as you are? Yes, that's what we're here to lift humanity.

[00:24:47.810] - Deanna Hinsz

I agree. I agree 100%. Judy, what's the biggest mistake that you see people make when it comes to doing this?

[00:24:56.910] - Judy Winslow

Probably that we discount it as not important when actually it reveals so much and can help us live a life that we really deeply enjoy. And dismissing some of these aspects as unimportant, when in fact, they all translate powerfully. And they all translate into not only having a fulfilled life, but also being able to afford it, because now you're being rewarded for your gifts rather than marginalized in any manner. So, yeah, to me, that's sort of to not go. Like, a lot of people would think, oh, I can do it myself, or it's not important. And neither of those are actually true.

[00:25:40.460] - Deanna Hinsz

So if they're thinking that, if they're listening and they're saying that to themselves right now, what is your answer? What would you tell them?

[00:25:48.040] - Judy Winslow

Get curious. Like, really even think about that. Why would you even consider that that's unimportant? Like, where did you come up with that? And then what's the evidence of that? And then the next part of it is really, for me, the big shift. And a lot of what I share with my clients is really around personal development. I believe that you cannot grow your business without growing yourself. So the next place to look is, are you resisting growth? Are you uninterest? Do you feel like you're uninterested in growing as a leader? And if so, why? Why, like, if you had a child, would you not feed it? If you were. If you had a little sister or a best friend that wasn't developing, wouldn't you want to assist in that process? Like, this is a process life. Who you are at 20 is not who you are at 40 is not who you are at 20. Yeah, like, thank God, right? Yeah. Like, enjoy the journey, for Christ's sake, and figure it out. Yeah. So get some help. Find community, join a mastermind, Join a small book club. You know, figure out where you can go.

[00:27:01.210] - Judy Winslow

So for me, like, I was suicidal and dark, and when I got involved in personal development, it changed my life. It didn't just change my life that day. It's been 30, 40 years of a completely different trajectory. Curiosity, education, that's never. I will never, ever let go of. And it's what gives my life color and flavor and joy.

[00:27:25.870] - Deanna Hinsz

I love that.

[00:27:26.610] - Judy Winslow

Mine's yours.

[00:27:27.410] - Deanna Hinsz

Yeah, I love that. So, Judy, how can we find you if we want to work with Judy and really get clear on leadership and get clear on branding?

[00:27:39.060] - Judy Winslow

Yeah, I would love to have a chat. So I'm at Unforgettable Brands, 2 Ts, 1s unforgettablebrands.com and I'm all over social at Judy Wins, and I'm on Insta at Jwins CEO Pro. So I love it. I'm the CEO of your life, people.

[00:27:56.900] - Deanna Hinsz

Oh, my gosh. That's great. It's great. And all of the links are right below, so you can click on those links and connect with Judy, and I encourage you to do so because there's so much information you can learn from her and work with her. So, Judy, thank you so much for being on the show today. This has been a wonderful conversation. Thank you.

[00:28:17.090] - Judy Winslow

It was a pleasure. Thanks so much.

[00:28:19.380] - Deanna Hinsz

You're welcome. All right, everybody, we'll catch you next week.

[00:28:25.330] - Deanna Hinsz

Thank you so much for tuning in to she is Unstoppable. I hope you're walking away today feeling inspired, inspired, empowered, and ready to take bold action in your business and life. Remember, the world needs your unique gifts and talents, so don't hold back. If you love today's episode, don't forget to subscribe, leave a review, and share it with a friend who needs this message. And, hey, let's keep the conversation going. Join me inside the she Is Collective, where unstoppable women like you come together to grow, connect, connect, and thrive. Until next time, keep dreaming big, showing up boldly, and creating a business that fuels your freedom. You've got this. Because she is Unstoppable.