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The Feminine Founder
Heyyyyy & welcome to The Feminine Founder!
I’m your host Caroline, former executive recruiter turned Digital Marketing Expert OBSESSED with helping female entrepreneurs how to start, grow and scale their personal brand & business online. I have a passion for empowering & supporting women with entrepreneurial ventures.
On this podcast, you’ll hear from women sharing their stories and unpacking exactly how they did it in their business because we believe that as curious & ambitious women we can ALL learn from one another and to be inspired!
Every week you'll hear from entrepreneurs and workplace experts and no matter the size of your organization- you’ll gain insight and knowledge to help support you in your journey too!
So happy you’re here! Now, let’s dive in!
The Feminine Founder
130: {Interview} From Corporate Marketing to Storytelling Success with Toby Myles
In this conversation, Toby Myles shares her journey from a corporate marketing career to becoming a successful storyteller and business owner. She emphasizes the importance of authentic storytelling in connecting with audiences and discusses the strategies behind effective messaging. Toby also talks about launching her podcast, 'Her Origin Story,' and how she helps clients build a story hub for content creation. The conversation wraps up with insights into Toby's personal life and passions beyond work.
takeaways
- Toby transitioned from corporate marketing to storytelling.
- She emphasizes the uniqueness of personal stories.
- Authenticity in content resonates more than perfection.
- Effective messaging requires clear goals and understanding of the audience.
- Origin stories are crucial for building trust with clients.
- Toby's podcast focuses on the journeys of women entrepreneurs.
- She teaches clients to create a story hub for content.
- Personal experiences can enhance connection with audiences.
- Toby enjoys motorcycle riding and outdoor adventures.
- Building relationships is key to success in business.
Connect with Toby more HERE and on LinkedIn HERE
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ABOUT THE HOST:
Former Executive Recruiter turned LinkedIn Expert & Entrepreneur. I'm here to show you that you can do it too! I help women how to start, grow and scale their personal brand and business on LinkedIn. In 2021 I launched ChilledVino, my patented wine product and in 2023 I launched The Feminine Founder Podcast and in 2025 I launched my LinkedIn Digital Marketing Agency. I live in South Carolina with my husband Gary and 2 Weimrarners, Zena & Zara.
This podcast is a supportive and inclusive community where I interview and bring women together that are fellow entrepreneurs and workplace experts. We believe in sharing our stories, unpacking exactly how we did it and talking through the mindset shifts needed to achieve great things.
Connect with me on LinkedIn HERE and follow the podcast page HERE
IG @cpennington55
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I'm so happy you are here!! Thanks for listening!!!
Caroline Pennington (00:01.294)
Welcome Toby. So you and I connected through a mutual connection, a fellow podcaster, and I'd love to hear more about where you are now and how did you get there.
Toby Myles (00:02.645)
Hey, Caroline, how are you?
Toby Myles (00:14.161)
wow. Okay. I worked in corporate marketing for 15 years in a direct response marketing division. So that's essentially just a fancy way of saying junk mail. It really was junk mail is what I did. But I used to use the fancy name because nobody wants to talk to someone who potentially could add their name to an email list or email list or, you know, mail list. But it was in that job.
Caroline Pennington (00:23.694)
So this is the best you can say.
Caroline Pennington (00:36.59)
place.
Toby Myles (00:42.055)
where I managed, I was a client strategy manager. I managed huge multimillion dollar direct mail campaigns. I managed teams of creatives, copywriters, designers, strategists, and I always loved the copywriting piece of it. And I did not get to do as much as I wanted to. And there was a part of me that thought if I ever get the opportunity either in this job or outside of this job, that's what I'm going to do. So fast forward.
to 2019, I was offered a promotion at that job. It was a horrible promotion. I was reporting to someone new who was a micromanager and I was miserable. I just, I just, I stuck it out to the end of the year, but I just couldn't do it anymore. That is not, I'm not somebody that needs to be micromanaged. I've owned businesses before and it just did not fit. So at the end of 2019, before the world shut down because of COVID, I
start my business. And in the beginning, I was writing all different kinds of copy. You know, I just felt like to really make a go of it in my business, I had to say yes to everything. And I quickly realized like that was really not the way to run a business. And so I, for a period of time, I specialized in email marketing. I got certified as an email strategist. And then I slowly evolved into
storytelling and using our stories to connect with people, which I feel like is even more important now with so many people using AI to write their content and copy. Nothing can replace your original stories. So that was kind of like a condensed version of how I got from point A to point B.
Caroline Pennington (02:32.631)
Okay, I love that you brought the storytelling piece because I'm fascinated by that because I'm with you. I want to get to know the actual human that's behind the screen, not just the AI or chat GBT that you can just plug into your computer phone and slap up their post size content. So why is storytelling so important?
Toby Myles (02:54.709)
Our stories are so unique to us, right? Even if you take two people who maybe have similar jobs, right, or similar childhoods or similar life situations, it's still no two stories are identical. And the more that we can talk about those things that are unique to us, the more our audience and our clients, potential clients,
see themselves in our stories and they start to trust us, right? Because they start to see like, wow, this person's really not perfect. They have like horrible days just like I do, you know, they spilled their coffee all over their white sweater right before meeting just like I did.
Caroline Pennington (03:43.222)
you but I feel like the messy content does better than the super polished perfectionism thing and I I'm active I'm not active on Facebook or TikTok but I am active on Instagram and LinkedIn but I feel like both of them people want to get to know like the messy office behind me and like I you know was flustered because a mic went out the first
Toby Myles (04:09.717)
Great. Yes.
Caroline Pennington (04:12.554)
So what type of stories do really well?
Toby Myles (04:16.553)
Well, like you said, the real, you know, this is actually real life. This actually happened to me, to me today, or in business, you know, my launch didn't go well. And here's why, here's why I think it didn't go well. Or I showed up on somebody's podcast and my dog was barking or the landscapers were here, right? Like that's just like real life stuff. I personally feel like the more, the more I have seen like super highly polished
Caroline Pennington (04:20.542)
This is actually real life. This is actually how it's supposed So you turn right, you go, and yes, yes, you know, you're supposed to be at the bottom. And here's what I'll tell you it.
Toby Myles (04:45.525)
content online, the more I'm just like that. I, it doesn't like, don't connect with that. Like I'm not a real highly polished person in my life. I'm lucky if, you know, I put on makeup and blow dry my hair, right? Like I want to connect with people who I feel get that and get me in that way. And so that's what I try to do with my own kind of content. And that's what I try to do with my clients to help them feel comfortable just being who they are and sharing their stories.
Caroline Pennington (04:45.815)
I take it.
Caroline Pennington (05:14.944)
Is there any type of story that's off-limit, like maybe something that's too personal or would be a turnoff to potential clients or your audience?
Toby Myles (05:26.473)
Yeah, I think there's kind of a rule of thumb that if it's something like really traumatic, it's okay to share it, but usually once you have already healed from that situation, right? Like not right in the middle of that situation. And like even that stuff helps people connect with you, right? Because other people are going through things too, you know, our lives aren't just all about our businesses, you know, there's personal stuff that goes on too.
Caroline Pennington (05:41.262)
situation.
Toby Myles (05:55.411)
And so I think that it is okay to share that, not in those really, you know, while the wound is still open, so to speak more later, you know, when it's kind of healed and maybe there's still a scar there. But I also think it's like very personalized individual, I guess is what I should say. Like people feel comfortable sharing different levels of.
intimate things behind the scenes. And I would never push somebody to like share something if they really were highly private and they didn't feel comfortable sharing something personal.
Caroline Pennington (06:29.102)
like something personal. Yeah, I'm big about energy and I feel like people can feel your energy across the screen and people are attracted to your energy and you can attract clients that way. And if you're out there sharing your laundry, that's maybe not storytelling, it's fencing and maybe you to keep that in a therapy session.
Toby Myles (06:47.477)
Hmm
Toby Myles (06:51.7)
Yes.
Yes.
Caroline Pennington (06:56.258)
But yeah, I know I hear exactly what you're saying. So why is the effective messaging piece and the strategy? Why do you need to have a strategy when you're going to want something online?
Toby Myles (07:06.517)
You have to know what your goal is. And if you don't know what your goal is, there's no way you can go from ground zero to achieving that goal. So that's like the big picture. But then like really drilling down to understand like, what is your goal? Who are you helping? And what are those people talking about? You know, if, if somebody was going to spend money right this minute, what would be the thing that would really resonate with them that would get them to say yes.
Caroline Pennington (07:16.494)
Thank you.
Toby Myles (07:35.527)
I need this, this is gonna solve a problem for me right now.
Caroline Pennington (07:40.632)
What's a common thing that you see with most of your clients that they all get wrong?
Toby Myles (07:46.837)
I think that my clients, a lot of them don't understand where they can use their stories and literally everywhere. Some stories are better for different pieces of your content. Some stories are better for online, for your website. Your kind of how you got your start, your sort of origin story is perfect for your about page on your website, which is.
the number one, number two most visited page on your website for that very reason. People, they might be drawn to you because you make a claim about how you can solve a problem. But once they get over to your website, now they want to know who is the person behind this brand and why should I trust them? Right. And we know like we are not for everybody, but the right people will read our origin stories and, and feel like we are speaking directly to them. So, and
The other mistake is that lots of times people don't understand like what parts of the story do you keep in? What parts of the story do you leave out? Like it shouldn't be, once upon a time. And then this long drawn out thing, right? You have to start, you you start somewhere and talk about a challenge or conflict, talk about how that was resolved and the lessons learned. And that is a very simple framework that you can use for storytelling in.
content on social media and in your emails.
Caroline Pennington (09:19.298)
love that. And when I read people's stories and it creates an emotion in me, it creates more action or more motivation for action for me to sign up for the course or get a one-on-one session with them or even just follow them, you know?
Toby Myles (09:35.509)
Yeah, I think that we, you know, that goes back to seeing ourselves in other people's story. Like who better to teach me something than someone who has already been through the same struggles.
Caroline Pennington (09:43.823)
that's something that's already built into the same structure. Yeah. So we were talking about something before we press record and I want to bring it back up because I'm so excited for you. You launched a podcast today called Her Origin Story and I want to hear exactly about how the launch went, how the lead up to it went. I want to hear about everything. So I'm so excited for you.
Toby Myles (10:06.645)
Thank you so much. Yeah. So the lead up was two years because I kept thinking of all these reasons why I shouldn't do this thing. Like there's so many podcasters out there already. Who's going to want to hear from me? Like all a bazillion excuses. And I was with my coach one day and had been talking about doing this podcast and we were kind of like, well, you know, maybe that's a, a maybe thing. Maybe you do that later this year.
Caroline Pennington (10:08.206)
Thanks watching.
Toby Myles (10:35.175)
And I was on a call with her one day and I just was feeling like really not excited about a workshop that I was hosting. And she's like, let's talk about like, what do you really like to do? What do you love to do most? And I said, I love to talk to people and I'm kind of nosy and I like to hear like, how, how did people end up where they are? Right. And I feel that curiosity in a lot of ways in my life. If I meet somebody in my neighborhood and they say, I'm from Illinois.
And then I'm like, well, how did you end up here in Pennsylvania? You know, I have that natural curiosity, but the same thing with other business owners and particularly with other women who I think, you know, I see online doing amazing things. I'm very curious about what was that thing that sparked them to the, on the journey that they are on now. And my coach said, just start talking to people, just invite people to a conversation and record it on zoom. That's, that is all you have to do for now.
Caroline Pennington (11:04.622)
I'm sorry.
Toby Myles (11:33.377)
And I said, okay, that's, what I'm going to do. But by the time I started scheduling my first interviews, which was beginning of April, I had already, it was already a thing. There was no turning back for me at that point. I had already designed the graphics and I knew for sure that it was going to be a podcast.
Caroline Pennington (11:43.982)
It's those tiny actions that really create excitement and compound into really large actions. And I'm backing up to what you said when you first started, when you answered my question. When I first started this podcast, the number one thing that people would say to me is,
Isn't the podcasting space overcrowded? I, every single time it would be from someone who didn't have a podcast.
Toby Myles (12:16.799)
Yeah.
Yes.
Caroline Pennington (12:19.694)
So you have to consider your audience always.
Toby Myles (12:23.379)
Yes. Yes. Yeah. I think that I just, you know, I got to the point where it's like, I've been thinking about this for so long. This is something I really want to do. And I just, I really had to just kind of tune everything else out and do it because it was something that I wanted to do without any expectations or without being tied to a specific outcome. But I realized pretty quickly when I started inviting people to be my guests, that I, I could offer something.
beyond just, sign up for my workshop or hey, join my program or buy this or buy that. I now had a platform where I could invite women to come and talk about their thing, whatever they're doing, what's their big thing. And that really started to feel really good.
Caroline Pennington (13:12.206)
love that and I'm excited to see where your journey takes you. So what's lighting up some of the clients that you're working with right now?
Toby Myles (13:15.157)
Thank you.
Toby Myles (13:21.253)
I am working with, I still do a fair amount of email marketing with my clients because that was really where I got my start. But I am really teaching people how to kind of build their own story hubs so that they never run out of content. So I'm actually working on something now, the core story hub where we create a structure.
where these stories live and we fill it with our origin story and our vision story and our client transformation stories and all these different types of stories that will live inside this hub so that you're never at a loss for something to share and you can start to stand out from everybody else online.
Caroline Pennington (14:13.102)
So when you're not working with your clients, how do you spend your free time?
Toby Myles (14:18.253)
my gosh. Well, I love my, I love hanging out with my family. I have two grown children. I have a grandson who's almost four, who I just absolutely adore. I love to read. I work out. I do yoga. I like to play around in the kitchen. My husband on husband and I ride motorcycles. go camping.
Caroline Pennington (14:43.008)
exactly what I was trying to pull out of you is the motorcycle thing because I thought that was fascinating when I saw that on your LinkedIn
Toby Myles (14:47.893)
Yes. Yes. Yes. I started riding motorcycles. I got my license in 2009 and you know how I was talking about, I overthought the podcast for two years. I overthought the motorcycle riding thing for 10 years. And, um, I did have young children at the time. So there was that to consider, but I had seen somebody
the sister of a close friend of mine ride her own motorcycle. And that was where I first got the spark. Like I am going to do that someday. I just thought it was so cool. So when I first met my husband, he had been riding motorcycles forever and we met online and I didn't know we were going to end up getting married, but I did love his motorcycle and I did think, well, this will be fun. If nothing else, this will be fun.
So for three years I rode behind him on his bike, but I never lost that sort of itch to do it myself. in 2009, I got my license, got off the back of his bike and just started riding my own and it's been what 16 years? Is that the right math? think 16 years. Yeah.
Caroline Pennington (16:05.41)
love that. What's your favorite place to take your motorcycle to?
Toby Myles (16:07.935)
my gosh, we're lucky where we live in Pennsylvania because there are a lot of really great back roads around here. Anyplace, anyplace. Back roads are my favorites. We've been out West to South Dakota to the Sturgis Rally, which is the big biker rally that, you know, everybody likes to go to, but that area is really beautiful for riding the Black Hills. We've been down to Florida.
West Virginia, all over the place. The thing about, the thing about adventuring on a motorcycle is that you're out in the elements. And so it really like awakens your senses, right? Like you can smell everything. Every state smells different. things look different when you're out in the air as opposed to in a car. and honestly, I've probably met the most amazing people through motorcycling.
Caroline Pennington (16:44.11)
Thanks.
Caroline Pennington (17:05.934)
I love that. as we wrap up, how can our listeners find you?
Toby Myles (17:11.317)
I am on LinkedIn primarily. You can look up the podcast, Her Origin Story. You can take a listen there. My website is tobemiles.com and I have a bunch of goodies over there, a pretty active blog over there. And I love meeting new people, so I would love to connect with your listeners.
Caroline Pennington (17:32.27)
Thanks so much for being here.