I am so thrilled to have Ashleigh Henry on the show to talk about ways you can build community as a brand. 

Ashleigh Henry has been in marketing, sales, and leadership positions since she was handed her first paycheck at the young age of 15. She was driving traffic in a well-known shoe store, watching the feet of our entering customers to be able to run sales that influenced said customers to purchase urgently and intentionally.

It was exhilarating for Ashleigh to climb the retail, corporate, higher education, and start-up ladder, holding positions such as Marketing Strategist, Copywriter, Social Media Strategist, Manager, Editor, and Co-Editor…until it wasn’t. Alongside her degree, Ashleigh decided to bring all of her experience into the online business space; she founded The Cheetah Company to serve modern businesswomen through their education, coaching, and consulting services and, in doing so, has helped nearly 100 female founders, nationally and globally, to build timeless and everlasting brands.

Ashleigh is out here killing it, and I am so glad you’re here with us today.

“Empowered isn’t just a brand word. That only half explains a brand and there’s no action behind it.”

– Ashleigh Henry, Marketing & Sales Consultant at The Cheetah Co.

You are so skilled at cultivating community. we may not all be able to hold this space at the capacity you can for others – but why is community connection like this vital for entrepreneurs building any type of brand?

As people are opening up more and reaching out to their clientele, How do you navigate that “vulnerability hangover,” as Brene Brown says?

It is a lot. Cymatics are my favorite place to go deep with breath work, meditation prayer, every Friday before I end my day, I’m like, journaling a time, and if you’re not a journal or an audio journals, fine. Something to get it out of your, headspace to go back and like self analyze a lot. That’s a good skill to have as a CEO and founder, but we can definitely take it to a higher spectrum of like, did I look a certain way it was I perceived this way.

So I really like to sit and think, where am I feeling this vulnerability in my body? Is it in my chest? Is it in my throat, my stomach, and I just focus on that physical feeling? To try to help it get out to have a space to just like, have a presence with it, have a moment with it, and help it calm down—very nurturer kind of setup, you know, almost mothering yourself or parenting yourself.

Then letting the words come out in audio or journal of like, okay, this felt like kind of an intense week, maybe I overdid it and my energy and connection. Can I slim down the amount of time that I do it? Can I turn off my notifications and set up a specific time when I do it? Time blocking for me is extremely helpful.

Then having those practices where I’m like, okay, I can lean on that. I don’t have to focus on like being embarrassed right now. Because I’m not a perfect conversationalist. I’ll, at some point, do something that’s a little awkward. And that I think, awkwardness is a beautiful thing, as a human. We don’t have to be perfect, and all put together just because we’re CEOs and founders.

I often see people put up a poll asking how people are feeling as if that is all you need to build a community. What are some of the big mistakes or cop-outs when it comes to connecting with community? 

My next question would be, hey, did you message every person to say, I’m so glad you’re feeling great today? What’s got you going up? Like what’s happening on a Tuesday? And we usually put a couple of like, positive pieces in a poll, like how are you feeling? And then we always put, do you need a pep talk or like, need a pep talk, click here. And we get a lot of clicks for pep talks.

Women founders are so incredible. A lot of them are breadwinners; a lot of them have to put on that masculine forward piece. No one’s really asking them how they are, truly caring and making sure that they are actually feeling empowered. Empowered isn’t just a brand word that only half explains the brand and there’s no action behind it. That’s what I would say, depending on what your brand profile is and where you’re coming from.

For us, we’re very passionate, we’re expressive, we’re gonna go out and like, if there’s 99, and we’re missing the one, we’re gonna go find the one and make sure they’re doing okay, that matters to us. And if it doesn’t matter to you, and maybe you’re like, a bit more of a prestigious brand or mysterious brand, that’s totally okay.

But at some point, you’ll still have to connect with people on a real level. I would say that’s where I see it the most is like prestigious brands becoming so unapproachable and disconnected. By remaining mysterious and just like behind this curtain that folks will start to fall out of love with it.

At first, it’ll be like, interesting, and ooh, I’m in suspense. But I feel like that’s a cop-out with branding, to not care about people and take a step forward and, and be approachable enough to have leadership while having, I would say, friendship. If you are treating your community like they’re an audience, that becomes voyeuristic.

If you’re treating them like a community, it becomes tribal; it becomes a village. So cop-outs, I would say, hiding behind the curtain, not being approachable, never asking how someone else is, and always wanting the attention, spotlight, and voyeuristic view of you.

How does this cultivating community impact the bottom line for brands?

I feel like just the overall future is getting shifted more and more with AI technology. We can really lose this personality, this piece of conversation, this community effect. Of course, there are so many gains to AI; we love AI, but was really focusing on community; your bottom line changes in ways that you can’t even expect.

So for example, we’re launching a retreat in September, we haven’t done a full launch for it, but because we have such a strong community online, folks are coming in paying in full and they’re ready to go. I think that has been the most obvious piece for me to say, community definitely is here. If we can help people for three years online, and now they want to come and sit down with us in person, that’s life-changing.

So thinking about how the community you’re creating right now may, at some point, want to be with you in person or have more of an exposure to the brand on a tangible field beyond the online space. That’s just where the future is going. We want to sit down, we want to break bread, and we want to have time together for marketing and money.

That’s why I say, bless the brand strategists of the world, because we cannot, we cannot like we have to end up building brands while trying to market while trying to create sales processes and just restructure the business usually. That is difficult, like we do it. But it’s definitely difficult because we would rather someone come in with branding guidelines that we can say like, you spent hours with an expert, and now we can build off of this; people have to go to you first, in my personal opinion, to have great marketing, I think you can have good marketing.

You could start, I don’t think it should hold you back by any means. But I do think that having a brand just elevates because it’s an obvious promise from the outside of this is who we are, this is what we do money connected to marketing, you’re only going to be able to get as many people into your offers and into your suite, to receive money from them and impact them through your service or product, you’re only going to be able to do that so far is the way that you can articulate your value through marketing. And so that’s where I think working with a brand strategist really comes into play.

My pet peeve is calling your community “family.” I think it blurs a boundary line, as if there are no rules and you would do anything for them. What is your perspective on that?

Being in startups, higher education, and corporate, I fully agree with you. I mean, you could just hear it, “we’re all a big family here.” It is like; I’m always on call. I understand. I love boundaries. I think boundaries are the sexiest thing that any person can have. But especially a modern business woman who wants to have a life outside of business.

I think for modern businessmen too, but for focusing on female founders here, which is predominantly who we work with. It’s just It’s insane how the spectrum has shifted from, you know, maybe 50, 60, or 70 years ago of women don’t work as often and they’re at home. They’re taking care of the children, home rearing, and child-rearing. Now we have swapped to this other side of the spectrum of; she’s kind actually working, she’s always on her phone, she’s always on her laptop… and that gives me the ick as well.

I want us to have a true holistically harmonious life and business without boundaries and creating a space where our peers, colleagues, and professionals in one room supporting each other to accelerate the growth of their brands. That’s what we’re doing here. It’s not necessarily family; there’s some feeling family feelings, maybe friendship feelings, village feelings.

What do community flocks look like for brands?

I like to put anything that’s in the online space that could feel like rejection or validation, a perception of approval into physical craft. Let’s imagine we were at a conference, and you’re literally locking the door saying like you, oh, can’t leave, you’re my community. Cops would be called; that’s very strange. So I hope that like makes the listener that’s listening smile.

But just remembering that’s essentially what we’re doing when we’re like, no, my community can never change. And my close day ones, from regular friends to business friends, to colleagues and peers, can never change, you’re going to outgrow each other at some point, or you’re going to grow in separate directions. And that’s okay.

I’ve seen a lot of polarizing content and overall, perspective-shifting content; some people are not ready for the perspective shifts that you’re trying to bring. And it’s just okay, don’t lock the door to the conference room. Let them go.

Ashleigh Henry bio

Ashleigh Henry has been in marketing, sales, and leadership positions since she was handed her first paycheck at the young age of 15. She was driving traffic in a well-known shoe store, watching the feet of our entering customers to be able to run sales that influenced said customers to purchase urgently and intentionally by way of the promotions she was running based on…them.

It was exhilarating for Ashleigh to climb the retail, corporate, higher education, and start-up ladder holding positions such as Marketing Strategist, Copywriter, Social Media Strategist, Manager, Editor, Co-Editor…until it wasn’t.

Alongside her marketing degree, Ashleigh decided to bring all of her experience into the freelancing world until it became clear that she didn’t just want to pay the bills – she wanted to create a company that was foundationally built on cheetah print, legacy-minded marketing, and sexy sales structures that could stand the test of trend and time.

The Cheetah Company, founded by Ashleigh, does this for female entrepreneurs through their education, coaching, and consulting services.

Since its genesis, The Cheetah Company has helped nearly 100 female founders, nationally and globally, to shift the way they approach their marketing and sales structures, to be focused more on the traditional elements that have worked for centuries while conceptualizing trendsetting pieces into their strategies without fear.

The Cheetah Company has supported female entrepreneurs seeking to move their brick and mortars’ into the online marketplace, scale their current businesses, or add new arms to their already profitable and existing businesses to move from four-figure months to five to six to multi-six and even to seven figures.