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Hey, what is up?
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Welcome to this episode of the Wantrepreneur to Entrepreneur podcast.
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As always, I'm your host, brian LoFermento, and I'll tell you what.
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All of you know what my word for this year is.
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It is bigger and when it comes to marketing and branding and growth and all things business and all of our goals this year, I can't help but think about how much that word is shaping my attitude towards all these things, and that's also why we went out and we found an incredible guest for today's episode.
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This is someone that, when I look at the entire portfolio of her work whether it was her professional career, her entrepreneurial career it is so clear to me that this is someone who doesn't do small things.
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This is someone who doesn't think small.
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This is someone who really thinks big and creates radically different solutions and strong brands.
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You're going to hear it in her messaging and the way that she does business.
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This is an amazing entrepreneur that I'm so excited to learn from.
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Her name is Rachel Chestnut.
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To tell you a little bit about Rachel, she's the founder and CEO of the Play Nice Agency, which is a trailblazing marketing and branding firm dedicated to reimagining and redefining the identities of today's leading brands by empowering clients to outperform their competition and expand their influence.
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Rachel's leadership has positioned the Play Nice Agency as a force to be reckoned with in the industry.
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Now, like I said, even before her entrepreneurial journey, rachel was up to some big stuff.
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Before she started her business, rachel spent a decade steering corporate communications for Deloitte Consulting's Office of the CEO and managing congressional responses for the Missile Defense Agency's Directorate of Operations.
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Her rich experience across both private and government sectors inspired her to establish an agency that fills the communication gaps that she witnessed in these fields, infusing a human voice You're going to see how much she loves this stuff that she does and culturally relevant storytelling into brand narratives.
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We're going to cross a lot of different intersections here today between marketing and branding, and growth and strategy and intentionality.
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I'm excited about this one.
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I'm not going to say anything else.
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Let's dive straight into my interview with Rachel Chestnut.
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All right, rachel, I am so very excited that you're here with us today.
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First things first.
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Welcome to the show.
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Thank you so much for having me.
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I was really excited when you guys reached out.
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I dived into the archives.
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You've had some really cool people.
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Yes, no.
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Thank you so much, Rachel.
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Honestly, it means the world to me when guests take the time to see all the other amazing guests and entrepreneurs in our ecosystem.
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It's why listeners love tuning in is because of amazing guests like you, Rachel.
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So you've got a lot to live up to today.
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You've got to kick things off by taking us beyond the bio.
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Who's Rachel?
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How'd you start doing all these cool things?
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Yeah.
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So where should I start?
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I started out in government.
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That was my first kind of foray.
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My professional career, working for the Department of Defense, went to grad school for military studies, all things defense.
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I thought I was going to be a squirrelly super secret spy.
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That's what I wanted to do.
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And then, you know, I kind of realized, after being stalked for a while by various agencies and kind of losing a lot of my independence throughout the process, I was like you know, this life's not for me.
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I'm going to go something and do something corporate after I've done the government squirrely stuff I can easily handle corporate went and joined Deloitte very quickly after that and then was with them for about six years leading corporate communications for the office of the CEO and consulting.
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So it was quite the transition from government to private sector.
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But I learned a lot along the way and kind of learned how agencies worked at the government level, how agencies worked at the corporate level, and then that kind of sparked my interest in, okay, how does it work when you start your own business?
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Because I kind of saw how everything worked, being built from the ground up, and so that kind of led me to where I am now, which is starting to play a nice agency.
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We're now a little over four years old.
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I founded it four years ago, when I actually it was after the week after my 30th birthday and we've been rocking and rolling ever since.
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Yes, I love that overview, especially because, rachel I mean, you heard me tease it in the beginning of today's episode and to me, what it really reveals is how big you think is that everything seems to be a stepping stone for you to something even bigger, and I can see that it shapes even the way that you see the world and the way that you see projects.
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I'll reveal this to listeners is that when we first came across your website, that big, bold headline of let's build something that matters.
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It really stands out to us.
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Talk to us about those big ideas, because you've got different language and you've got different messaging than what we typically see in the marketplace, which I want you to show.
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The contrast to us, because you clearly know how most people are, but you recognize that difference in the way you think and the way that you operate.
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Fill in that gap for us.
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What is that difference?
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How do you think so big fill?
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in that gap for us.
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What is that difference?
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How do you think so big?
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Yeah for sure.
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So you know, starting out in the government, it's very clear.
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If anyone's ever worked I mean, everybody has had some type of communication with the government.
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It's typically not the kind of communication most people want to have, whether it's the IRS or whoever you're dealing with.
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But you know, we were writing in a way that was very robotic.
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There was nothing that was human sounding, everything was very passive in terms of the way people interacted with one another.
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And I found that, you know, I expected things to be different when I left the government to go work in the private sector, thinking, you know, the stakes are a little bit higher here, in the sense that it is supposed to be relationships based, it's supposed to be client based, and so at least that perception for my end was that it would be more human interaction, more authentic communications, and it turned out that it wasn't at all.
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It wasn't at all.
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It was actually very similar to the way that I was used to 70,000 people, you know, trying to elevate the language and the way that we were appearing internally and externally to our people and our clients.
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It just became formulaic, boring, and I began thinking how is anyone supposed to relate to us?
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Why do they care about what we have to say if what we're saying sounds the same as everyone else?
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And so that's when I decided to branch out on my own and I made a point for our agency to be very authentic and transparent in the way that we not just represent ourselves but the way that we represent our clients.
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And I think one of the biggest differentiators of our agency is that, you know, people think of small businesses and they think, okay, they're always buying to get work, they're always trying to, you know, get RFPs, get contracts.
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We turn down work with people and clients who don't want to have that kind of authentic, transparent, more conversational, funny, engaging, lighthearted kind of approach to some of their communications.
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There's obviously a time and a place for that.
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Sometimes it's not always appropriate, but we like to kind of push people towards that edge so they become more of a human and more relatable to their consumers.
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Yeah, Rachel, I love hearing the building blocks of your views on communication, branding, marketing, because when I think of the most impactful and memorable brands of our lifetime, it's they all have something big to say.
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I think about the Nikes of the world.
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We all know those three words that make us think of Nike every single time.
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With just you and hearing you talk about I guess you have a unique vantage point, coming from the world of government and coming from corporate, in that you've seen that boring way to communicate.
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I remember when I was 22 and I started my marketing agency in Boston, I was presenting to the board of a big manufacturing company in Massachusetts and I started that presentation by saying to everybody hey, what's up?
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Everybody my name is Brian.
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And the CFO said to me after he's like did you start by saying what's up?
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And still, here we are, over a thousand episodes into this podcast and what is up has become the way that listeners have accustomed to me greeting because it's just me, I can't help but be me.
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But I want to ask you this, Rachel, because it is a little bit of a balance and you alluded to that is that we have to know the time and the place I've always wanted to have this conversation with someone like you here in the open, for everyone to listen to.
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A lot of times in my life I didn't feel edgy, I didn't feel bold.
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Why?
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Because you know, when I started my business, I was a 22-year-old white suburban dude from central Massachusetts.
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And I was like there's nothing edgy about me.
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I had a four-year degree and I've done all this.
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Where's that edginess come from?
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How can we find ourselves in a way that makes us different from everybody else, even when we just feel truly like, you know, every other social media agency or web development agency, or lawyer, whatever our industry might be?
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Yeah, I think that probably not the easy answer to the question, but the really honest one is it starts with who founded the company and the tone in which they founded the company.
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And for me, I learned that when I thought I wanted to be perceived a certain way and I thought, okay, this is gonna be edgy, this is going to be alternative, this is going to be something that may be hard for some people to swallow or get on board with, I realized every time I thought that it was a fear-based response.
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And so I have learned through my last 15 years and various careers, but also as a founder, that fear is really the thing that holds you back the most from achieving the most amazing things for yourself personally and also your business.
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And so for me, I knew I already had an edge.
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I always did.
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I'm very individualistic in the sense that I kind of don't care if people love who I am, because I know that I'm a good person and that I'm, like, generally likable and Sometimes can be funny.
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My friends and family think that I'm pretty funny and sarcastic and I just kind of let that tone carry off with a lot of my clients and a lot of our internal comms and it's been received really well because I'm not afraid to be me and it gives people permission to be themselves and I think that that's a really healthy message at the end of the day is for people to be able to just be their authentic self and feel safe doing it.
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And they're not going to do it unless you know leadership is giving them the green light to do so.
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Yeah, I really agree with that, especially because what you're talking about us being us, it's going to transcend every single thing that we do.
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I mean the impacts of our personality, our tone, our voice permeates into whether we're on a podcast together or whether we send an email to somebody.
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I always smile.
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I think it's high praise when someone says I could hear your voice when I read your book or when I read this email, and I think to myself good, because it was me that wrote it, so I hope it sounds like me, and so I really appreciate those insights and that approach to it.
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I want to ask you about that, because when we talk about the downstream effects of using our personalities, using our voices, what does it create?
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An experience?
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And that's why I love the language on your website that says the brand.
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Experience is the brand.
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Talk to me about that messaging, because I don't think a lot of people embrace that when they think about what is my brand?
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How do I bring my brand to life?
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Erase?
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that when they think about what is my brand?
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How do I bring my brand to life?
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Yeah, absolutely.
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I think I actually recently saw a commercial that was for Amazon Prime, but they did something very similar to what Apple does and Apple's whole branding and marketing team, which is fantastic.
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They actually do a lot of their commercials and you don't even know that they're advertising for a product.
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It's about a human experience, it's about something that we can all relate to, and, at the very end, the solution to whatever problem they're having turns out to be a product.
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But that really wasn't the point of the advertisement.
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The point was creating that emotional connection, and so I think that when companies are able to understand their consumers well enough to be able to relate to them on that personal level and get it right, that's an art and it's also a fine line, because if you get it wrong, then you look careless.
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If you get it right, then you look very adept and attuned to other people's personalities or the sentiments of the moment.
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And another thing that we have on our website is that brands are, you know, agents of cultural change.
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So what's the point of a brand if you're not trying to have an impact in the current moment in which you're existing.
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It just doesn't make sense for any brand to be able to say, okay, yeah, we're putting out this product, the service, whatever, but we're gonna stay clear of whatever's happening in the world, like no one has the luxury of doing that.
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And if you do, then you don't have it for very long because those things aren't going to impact your business and your bottom line.
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So why not get ahead of it and make that part of the conversation?
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And so so you know, the brand experience is the brand, because what you're experiencing your human emotions, cultural transitions the brand has to be able to relate to and speak to you in that moment, or it's not doing its job.
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Yeah, rachel, I'll tell you what most listeners can't see us right now.
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Obviously, you and I'll tell you what most listeners can't see us right now.
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Obviously, you and I can see each other, and I see it even in the way you talk about it.
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With your hands, you bring these things together and I think that's so important because I always used to view these two forces that we're kind of talking about right now as separate.
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There's the person, the people behind the businesses and the brand.
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I always viewed them as separate and I remember I used to really struggle with this in my early twenties of should I build my personal brand Like a Tony Robbins?
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Is that what I want to be one day, versus building a business brand that I can stand by this business, even if it's just me up front and say this is my company, this is how I service people.
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I always thought the two were opposing forces, but I really think about it and I reflect on so many visionary founders that have left a lasting legacy on society, on the world at large.
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You and I talked off the air about Elon Musk and what he's doing with Starlink.
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You're in the mountains of North Carolina, so Starlink has been a particularly important solution for your geographic region over the past 12 months, and when I think about Elon Musk, it's a two-way street.
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Not only does everything he touched seem to turn to gold, whether it's Starlink or the Boring Company or Tesla or any of his various companies, but also it works in reverse.
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Is that when we think about Starlink, we know the founder behind it?
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So talk to us about how all these things play together, rachel, because it is a lot of moving parts and I think for most entrepreneurs it's just big question marks.
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Yeah, totally I, you know that's something that I personally struggled with at the very beginning of starting.
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The agency was okay.
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How do I have to change my profiles now on social?
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Do I have to start acting a different way in meetings?
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How should I present myself when I'm out in public?
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Because I am the face of this, and that's a good and a bad thing.
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I'll say we worked with a client about seven months ago where that very question was asked.
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It was for a food and beverage brand and alcohol sales, and the person in question who wanted to be the face of the brand was an A-list celebrity that was known for getting in trouble.
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And so we kind of came in and had a conversation with him and his team and you know it was a very large contract that we knew we were going to probably lose if we told him the truth.
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And the truth was that for this brand, having him as the face was not going to work, because if he messes up once and it becomes public, that's going to reflect on the brand.
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However, that's not the case for a lot of brands.
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For us, I mean in my team, I've told my team I am the same way.
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I'm very honest and transparent.
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I make jokes, I upload funny videos.
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I want people to know who they're working with.
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I don't have anything to hide and I think you know the higher up profiles, like an Elon Musk that we were talking about.
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You know, anytime something negative happens in the press, obviously it's going to impact perceptions of whatever product he's putting into the market.
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But he's put himself into a place where he could probably do a horrible, horrible thing and we would still be buying Teslas and Starling.
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So it really depends on where you're at in your business journey and as an entrepreneur and walking that fine line between how much you want to show people and how much you're comfortable showing people.
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But I think one of the biggest mistakes that you can make is not being present at all, because a faceless company again kind of gets into what we were talking about is really kind of hard to engage with from a human interaction perspective.
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Yeah, and I think the biggest way that people fool themselves is that term.
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B2b I've mentioned this so many times before on the show is business to business companies think well, nobody needs to know.
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I think of my most successful friends, eight figure entrepreneurs.
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A lot of them own a lot of software companies, and a software company doesn't need a human face behind it, but a lot of them make that conscious decision to be the face behind that software.
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I mean, a big one that a lot of listeners will be familiar with is Russell Brunson with ClickFunnels.
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He didn't just launch ClickFunnels and let that be its own brand, which it is, but he powers a lot of the content.
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He's visible on the website, the video marketing, the ad campaigns, and I guess that's a perfect segue, rachel, that I want to talk to you about today, because part of what I really respect and admire about your agency is you guys are a full stack agency.
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You don't just do the strategy.
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Part of it is you help people with messaging and copy, with the website development, with social media content.
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A lot of people can tell you what their brand is, but of course, your brand needs to show up in all of these places.
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Talk to us about the importance of those platforms or communication channels or how we can make sure that the things that we say we stand for are actually visible in all the places that people find us.
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You know, what's funny about what you just said to me, working in branding and marketing is, you know, people actually don't generally understand their own brand.
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They think they do and where they play, but they often don't.
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And if I had a dollar for every time we had a client or prospective client come to us and didn't have a robust competitor analysis or profile made, you know, for their agency, or they didn't understand the engagement ratio of new followers and what that means for engagement on their you know, various social platforms, like I, would be very, very wealthy.
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I think that actually the biggest problem for most brands that at least what we have seen in the market and it's certainly the ones that we have worked with and helped over the years is that they actually don't know what their brand is or what it should be and how that should appear externally on their owned media platforms.
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And I think that kind of goes into earned and owned media is you kind of have to get the own media under control before you can go to earned media channels and really have that solidified brand.
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And so, depending on what company it is that you're talking about, like the social, your social engagement right now what we're seeing is.
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Linkedin is far and beyond taking the front seat in terms of getting engagement and actually leading to new business opportunities.
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Instagram has fallen back into.
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It's just a social platform that is there to generate awareness but no one's really getting business from it.
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Tiktok is an example.
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If done right, it has been very successful for companies looking to go viral, but their whole strategy then hinges on their ability to quickly adapt to TikTok.
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So what we generally advise, and what we spend a lot of time thinking about, is what's the balance between your presence on social media, what you're wanting to do with earned media, so how you're going to position yourself with PR and PR outlets which we secure relationships with, and then what is your presence look like on your website?
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All of those things have to speak together, because if you're posting something on Instagram or LinkedIn or any of your social platforms that's not reinforcing or speaking to what you're putting out in the Financial financial times or, you know, on your website, then it's just going to fall flat and it's going to sincerely be a waste of time to even bother with managing social.
00:21:24.247 --> 00:21:30.811
Yeah, rachel, I'm sure a lot of people who are hearing you talk about this are thinking that's so overwhelming, how the heck am I going to manage all of that?
00:21:30.811 --> 00:21:32.583
And that's why agencies like yours exist.
00:21:32.583 --> 00:21:34.224
But I want to share this with you.
00:21:34.224 --> 00:21:46.425
It's praise that I often give to my entrepreneurial friends, and it's probably the nicest thing that I can say, because I know how hard it is to get this right in business, and that is my friends who are crushing on all these fronts.
00:21:46.425 --> 00:21:59.105
I always say to them I love your ecosystem, I love the consistency, I love the value that you give throughout your ecosystem, and I really mean it with that word ecosystem because, to your point, it doesn't matter where you go to find them.
00:21:59.105 --> 00:22:02.611
You could land on their website and you'll see all the exciting things that they have going on.
00:22:02.611 --> 00:22:03.502
You go to their social media.
00:22:03.502 --> 00:22:05.782
It's the exact same thing, rachel, transparently.
00:22:05.823 --> 00:22:13.790
It's one of the things we're very committed to here in 2025 is, if you follow me on LinkedIn, you have no idea what episodes are maybe coming out this week.
00:22:13.790 --> 00:22:18.509
If you follow me on Instagram, you hear from me like four times a year, and we want to change that.
00:22:18.509 --> 00:22:20.021
That's the hardest part.
00:22:20.021 --> 00:22:22.868
Is that consistency across the ecosystem.
00:22:22.868 --> 00:22:28.309
So the question that I pose to you with regards to the ecosystem is how strategic and intentional is it?
00:22:28.309 --> 00:22:32.428
Is this something that you look at on a weekly basis, that you plan out for the next month?
00:22:32.428 --> 00:22:34.551
Is it a quarterly planning process?
00:22:34.551 --> 00:22:38.891
How the heck do we get the entire ecosystem right and consistent for the long term?
00:22:39.819 --> 00:22:41.625
Yeah, that is a very fair question.
00:22:41.625 --> 00:22:46.223
It's actually one of the biggest questions that we get asked from all of our prospective clients.
00:22:46.223 --> 00:23:10.810
And I will say, having the background that I have and my team's also, my team's background in corporate communications and marketing strategy has been a huge, huge asset to how we're able to serve our clients, because how we generally start every relationship, it's very similar to how many marketing and branding agencies start through a discovery process.
00:23:10.810 --> 00:23:22.422
However, we're a little bit different in the sense that we start with, if they have a analytics platform, whether it's Sprout or whatever back-end tracking metrics for their social websites.
00:23:22.422 --> 00:23:24.626
We ask for access for that.
00:23:24.626 --> 00:23:26.790
We ask for competitor access.
00:23:26.790 --> 00:23:33.851
We basically every piece of information that we can get about their company over there since being founded.
00:23:34.151 --> 00:24:04.465
We put together this story and we go through all the material and then we work with those teams to develop a year over year marketing, very comprehensive marketing and comm strategy to include everything from external comms, which is, you know, social media, earned media placements, their website, all of that, whether they want, you know, video advertisements, thought leadership POV to internal newsletters or, you know leadership communications to the team.
00:24:05.328 --> 00:24:12.964
And then we're also looking at okay, how do we marry that internal communication and culture to reflect what's external.
00:24:13.005 --> 00:24:21.722
And I'll say this is not a popular thing to say and I think I've already gotten in trouble once, at least with Deloitte's PR team since I left, for saying this.
00:24:21.722 --> 00:24:40.635
But the reality was that internally you know there's 65,000 of us we would get you know newsletters and what was being said, what the information that was being shared none of that matched with what we were seeing in the marketplace externally.
00:24:40.635 --> 00:24:51.413
So, as an employee, you're starting to feel misled or misunderstood or like you're not getting the full picture, and so that really led us to start off every engagement with.
00:24:51.413 --> 00:25:07.420
I mean we take a solid three to four months of really understanding every aspect about the agencies that we're working with to develop a very comprehensive marketing and communication strategy to hit all of their platforms so that the message is tailored for each platform.
00:25:07.420 --> 00:25:16.844
But we're also singing from the same song sheet every time we post something, so we're not looking like, you know, one hand is not talking to the other.
00:25:17.506 --> 00:25:27.126
Yeah, and of course, in order to do that, that song sheet must first exist, and I love the depth and comprehensiveness that you bring to the table and help developing all of this strategy.
00:25:27.126 --> 00:25:29.231
It sounds like for the very long term.
00:25:29.231 --> 00:25:47.555
So, rachel, I almost feel bad asking you this, but here in Q1, I have to inject this into every conversation because it's what we're getting all the emails about from our listeners, and that is, of course, ai, and I would imagine in your line of work, everybody just wants to spam AI and get all the AI answers from all of that and have it do all the work for us.
00:25:47.555 --> 00:25:56.481
How can we effectively and appropriately use AI to actually retain our unique brand voices and the experience that we want to deliver to our audiences?
00:25:57.585 --> 00:26:07.701
Yeah, of course, as you already know and I'm sure a lot of people know that have been listening to your podcast and just paying attention to the news in general, ai has come really far.
00:26:07.701 --> 00:26:21.153
I think we all experienced the early days of chat GPT, when you know we were surprised by its capability, but it also wasn't capable enough to actually sound like us and not sound like a robot.
00:26:21.153 --> 00:26:25.087
And it's gotten to the point where you know the proficiency is there.
00:26:25.087 --> 00:26:28.520
I know with Jasper AI, for instance.
00:26:28.520 --> 00:26:35.413
For people who are familiar with Jasper, it's actually a tool, an AI tool that our agency leverages is Jasper.
00:26:35.413 --> 00:26:38.924
We do not use it for content.
00:26:38.924 --> 00:26:42.333
We are very much hands-on when it comes to the content.
00:26:42.333 --> 00:26:47.451
You know, if there's refinements in language or like what's a better word for this, we will use it for that.
00:26:47.451 --> 00:26:52.030
But we generate all of our content organically and it's us doing the work.
00:26:52.211 --> 00:27:01.212
What we have found AI to be very helpful for and using Jasper AI as an example is actually putting together visuals.
00:27:01.212 --> 00:27:06.728
So our design work obviously has to mirror the content that we're working with.
00:27:06.728 --> 00:27:11.806
So, for instance, I'm a writer, I'm a content strategist, I'm a marketer.
00:27:11.806 --> 00:27:13.090
I'm not a designer.
00:27:13.090 --> 00:27:15.681
I don't know the first thing about design.
00:27:15.681 --> 00:27:18.790
My head of design is amazing at design.
00:27:18.790 --> 00:27:20.315
She's incredible at her job.
00:27:20.315 --> 00:27:26.250
She doesn't really know how to write a lot of content, which is why we're in the roles that we're in.
00:27:26.250 --> 00:27:41.669
What becomes difficult is when I have this content, I need a design to go with the content, but there is not really a way for us to figure out what's the best way to approach this into a visual.
00:27:41.669 --> 00:27:52.240
So it kind of helps initiate those first ideations of visual direction for design, and that's typically what we lean on AI for the most.
00:27:52.622 --> 00:27:53.505
Yeah, I love that.
00:27:53.505 --> 00:27:55.590
No longer do we have to start a blank canvas.