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When you’re wearing every hat—from sales and marketing to operations and HR—you aren't just the founder; you're the bottleneck. If you are struggling to scale your business without losing your sanity, this podcast is for you.
Hosted by Catherine Brown, Chief of Everything is designed to help founders trade the "all-the-hats" hustle for high-impact growth.
In each episode, we interview subject matter experts who have been exactly where you are. We skip the fluff and distill years of expensive mistakes into essential principles you can use to make your business more efficient and your leadership more effective.
Ep03
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Introduction to Dana Casto
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[00:00:00]
Catherine Brown: On this episode of Chief of Everything, I introduce you to my friend Dana Casto. He is a fractional chief marketing officer who works with consultants and coaches. Fractional CMO means that he cares about your plan first and foremost. Not random tactics like [00:01:00] outsourcing Instagram posts that your neighbor's kid does for you, or buying ad hoc ads, you know, rushing before a speaking event.
Understanding Marketing Overwhelm
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Catherine Brown: I. Dana addresses the marketing overwhelm all micro business owners have felt. You will see that a marketing strategy is something anyone can think about because he shares his three-part framework and teaches us. This framework is a Venn diagram that you won't wanna miss, and I love Venn diagrams. So let's dive in so you can stop doing random acts of marketing.
It's time to have your marketing produce the qualified leads you want. I.
Dana. I'm so excited to talk with you about marketing. You're the marketing pro. I'm the marketing loving amateur. So glad to have you here.
Dana Casto: Thanks for having me, Catherine. Really appreciate it.
Catherine Brown: So.
Three-Part Marketing Framework
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Catherine Brown: On this episode, we're [00:02:00] talking about how people move from being the chief of everything in their business in a bad way, which is just how we all start to being a smart chief of everything. And we're gonna talk today about marketing strategy with you. And so my first question that I wanna open with is kind of a paradigm shift I wanna ask.
What is the marketing principle that feels kind of wrong to that founder, but is actually a secret to scaling?
Dana Casto: Yeah, absolutely. I love this question. So from where I sit as a marketing advisor, I see lots of B2B service providers think they actually need to do more when it comes to marketing.
Catherine Brown: Hmm.
Dana Casto: What they actually need is clarity around what's working, what's not, and where they should focus their energy when it comes to their marketing and sales. So I see a lot of wasted time. I see a lot of wasted energy and a lot of wasted [00:03:00] money. Because they're unclear on where to focus.
Fragmentation in Marketing
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Dana Casto: And I bucket these focus areas into three themes. first theme is fragmentation, and what I mean by that is everything that they're doing is kind of disconnected.
So nothing really compounds over time that often looks like. marketing as isolated tactics or creating content in every format they can think of, but not really understanding which format performs best for them and their audience.
Catherine Brown: Fragmentation.
Dana Casto: they, they should be doing needs to relate to everything else that they're doing. They need a measurable, goal aligned strategy. Okay.
Reactivity in Marketing
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Dana Casto: So the second bucket is what I call reactivity. And what I mean by that is that they're chasing momentum instead of building consistency
Catherine Brown: Hmm.
Dana Casto: that often looks like reacting to slow periods, kind [00:04:00] of panicking a little bit, right? Or they're reinventing messaging instead of just fine tuning it over time.
Catherine Brown: Okay.
Dana Casto: Marketing is a long game, not necessarily a quick win. Small adjustments along the way, yield better understandings over time than throwing everything out and hitting a reset. That hard reset, don't really learn a lot from it.
Catherine Brown: Hmm.
Dana Casto: just starting over.
Misalignment in Marketing
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Dana Casto: And this third bucket I call misalignment. And what I mean by that is they're visible. have a website, they're on social channels, they're sending emails, they're going to events. they're not reaching the right people
Catherine Brown: Hmm.
Dana Casto: that often looks like they're talking to too broad of an audience, or they're going where they want to go instead of where their audience is. So they're not necessarily showing up in the right places to meet the right people at the right [00:05:00] time.
Catherine Brown: Okay.
Dana Casto: So the advice that I give. Is that they need to get specific about one audience
Catherine Brown: Okay.
Dana Casto: really understand where that audience is and go there.
Catherine Brown: One audience. Where are they? Question mark And go there. Now, something you've said, Dana, that I'm gonna bring up and play devil's advocate or pretend to be that small business founder, which. I am, I don't have to pretend very, very, very hard for that. Okay. When I hear some of the things you say, this little flashing light is going off in my brain, and it's saying, when you're talking about proof or data or things that indicate, how do you know?
And I literally think, oh, that feels hard. Are you telling me that as a chief of everything, I have to learn to understand Google Analytics? What are we talking about? That is the baseline for a solid foundation for [00:06:00] founders.
Dana Casto: yeah, absolutely. And if we're talking about lots of different service offerings or products, it can feel really overwhelming.
Catherine Brown: Yeah.
The 1-1-1 Rule for Marketing
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Dana Casto: So one of the pieces of, of advice that I give all the time is think about one service offering getting really good at that one problem solving solution that you've developed over time.
Catherine Brown: Hmm.
Dana Casto: And so when you're focused on one offer, you can follow the 1 1 1 rule,
Catherine Brown: Okay.
Dana Casto: one clear audience that they serve for that problem that they're solving and one meaningful problem that they're solving for, and they're going to one channel to show up consistently for that.
Catherine Brown: One audience, one problem, one channel.
Dana Casto: Yep. One
Catherine Brown: Okay.
Dana Casto: one problem, one channel.
Catherine Brown: Okay, so what are you gonna say to the person who says, I feel like I have to do a test? How [00:07:00] do I know which channel's? Right for me,
Dana Casto: Hmm. Yeah. So this comes to often a question around like content. Or format for their marketing.
Catherine Brown: okay.
Finding Joy in Marketing Strategies
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Dana Casto: And so one of the questions that I ask clients all the time is, do you love to show up?
Catherine Brown: Hmm.
Dana Casto: brings you joy? Do you like online communities or do you like in-person events? Do you like one-on-one conversations or do you like group format? when you can identify. Marketing or strategies that actually bring you joy and you love doing it, guess what? You're more likely to actually do it consistently over time.
Catherine Brown: It is kind of like you're a trainer, a health trainer that's saying if you are willing to do that, you just go, you like, I don't have to convert you to liking Zumba if you don't like Zumba. Right? That's not gonna work. You're not going to go. [00:08:00] So what is something that gets you moving that you do enjoy?
Dana Casto: Motivation is a huge deal, and you really to, to actually move the needle. It's actually much more about consistency and read repeatability, you know, new year, new you often means people are going to the gym more and more often, right?
Catherine Brown: Right.
Dana Casto: what, what's the statistic? Like 90% or so drop off after. February one.
Catherine Brown: Yes. Yes.
Dana Casto: But if you think about it in terms of like, okay, I'm gonna block 60 minutes once a week to go to the gym. I'm only gonna try to achieve that. Try to go once, well translate that to marketing and content creation, right? You gotta block time to actually do the work. And this is not like. Implementation time or sending the email. This is creative time to create where you are. Setting aside time to [00:09:00] think, to generate ideas, to actually create that content. That is a muscle that has to be developed over time too, just like going to the gym.
Catherine Brown: All right, so let me state back some of my favorite things that you've said and that'll lead to our next question. It sounds like you believe that founders early stage businesses, micro businesses, they're reluctant to narrow down the scope of offering and they're reluctant to pick a key audience to go after and have that target persona or early enough.
So they're talking about too many messages to too many different kinds of industries, and they feel like they have to show up everywhere. And so. This feels like a big energy drain to me. Is this the same, would you say it's the most common energy drain? Or are there things that you think, friends, if in the first year you would do X, that's a [00:10:00] better, is there something that's even a better energy saver?
Dana Casto: Hmm, that's a really great question. So. You know, it's, there's sometimes there's fear behind
Catherine Brown: Yes,
Dana Casto: know,
Catherine Brown: I would. I'm gonna, I'm gonna jump in and say it's almost all about fear. Okay. I mean, personal from personal testimony and all the sales coaching I've done, there's just so much we don't know. And let's be real. A person starts as a founder and becomes the chief of everything because of a variety of reasons.
Sometimes it's an aspirational identity, sometimes it's out of necessity. There was a layoff, who knows? And nobody knows how to do all the things. It's very overwhelming.
Dana Casto: Yeah. It absolutely is. And when you're starting a business or you're hitting certain milestones in your business there is a tendency to try to grab at anything that's gonna stick and get momentum. When I'm working with clients, I really want them to answer three questions with me, and it's a Venn diagram.
And the thing that we go after is the overlap [00:11:00] of these three things.
Catherine Brown: Okay.
Dana Casto: The first is are you really an expert in,
Catherine Brown: Okay.
Dana Casto: just good at, but exceptional at.
Catherine Brown: Okay.
Dana Casto: And the second thing is in that area. What are people most likely to buy from you and what is that problem you are solving for them? And that third area is what brings you joy in your work.
Catherine Brown: You are back to joy 'cause you feel like they won't do it. They won't stick with it.
Dana Casto: Yeah, absolutely. You know, I've been in marketing for 25 odd years.
Catherine Brown: Hmm
Dana Casto: worn all the hats, I've done all the things, so I can do all of the different parts of marketing that's available to do. But strategy is what I love.
Catherine Brown: hmm.
Dana Casto: It's what brings me joy I know that I [00:12:00] bring the best to my clients when I'm in that zone of genius for me, when I am doing the thing that I truly love. It's really the reason I started the business in the first place
Catherine Brown: Hmm.
Dana Casto: is to do only the thing that I love to do.
Dana's Personal Journey in Marketing
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Catherine Brown: Did that take you a little while, Dana? Like tell us just a little bit about your story. Did you start out knowing it would be strategy or was it process elimination because you became bitter about work that you had accepted? Thought? Why did I agree to that?
Dana Casto: so I started my business five years ago in some change, like five and a half years ago. probably took me three years into it, going through the process of like, I can, I can build websites, I can write email copy, I can do social media posting and implementation. And because I, I could sell those things.
I could do them. But what I noticed is along the way, the part that I was [00:13:00] actually loving doing was solving the problems that my clients were having and identifying them and figuring out solutions to them. That's really all strategy is at the end of the day, is understanding what's working, what's not working, and what we need to double down on to do more because it is and what we need to let go of because it's not actually working.
Catherine Brown: Okay, so. Even the teachers here are saying this is an evolution, it's a process, and our admonition to people would be niche as fast as you can into that ideal buyer. Simplify your offers and get honest with yourself. About where you're willing to show up. Do you love sending emails? Dana, I [00:14:00] love sending emails.
I know you know this 'cause you're on my email list.
Dana Casto: Yeah.
Catherine Brown: If you take all of the groups, I'm responsible for my leaders events. I'm counting every single email. Okay? But this is how much I love email marketing. Now I have a team that does this. So to be fair, to the solopreneur who's listening, know that I have.
A part-time contract writer and the person else, someone else who loads it in Kit. So I do have a team now that helps me. I don't do it by myself anymore, but my, I'm embarrassed to tell you, but for my little business, my team sent 68,000 emails in 2025.
Dana Casto: I love it. I absolutely love it.
Catherine Brown: Now for the listener, I've been doing this for 10 years. And this is me and two part-time people, you know, that put these together and it's across every single thing, across probably four or five brands. So, I mean, this is a lot of emails, but you know what? It didn't feel like that to me. I love email marketing.
Dana Casto: So I know why I love email marketing.
Catherine Brown: Why is that?
Dana Casto: about, well, I'm curious about [00:15:00] why you love it, but the reason that I love email marketing is I believe it's really relationship building. It's a one-on-one conversation if it's written in the right way. If, if it's really heartfelt, if you understand
Catherine Brown: who
Dana Casto: you're writing to, then it is a one-on-one conversation. You know, I think of current, and whenever I'm writing emails for my business or for clients, I'm thinking about one particular person. When I'm writing that copy or I'm having a contractor who works with me, actually write the copy. Like part part of the work that we do is like getting really specific about audience profile.
Catherine Brown: Yes,
Dana Casto: who is that person? What are their fears? What are their motivations? What are their desires? What's holding them back? What's, what's elevating them up? how do we align that with the service offering for the clients? How do we [00:16:00] align that with the service offerings that I offer?
Catherine Brown: I do love it for that reason. I think the other reason I love it, Dana, is because it's a little bit pathological. Truthfully, it's that because I want to serve the whole world, even though I know that that's not realistic. Email marketing is a way you can teach and give
Dana Casto: Mm-hmm.
Catherine Brown: that's free.
Dana Casto: Yep.
Catherine Brown: I mean, it's not free to me, right?
But that it's free to the consumer. And it just means a lot to me that, for example, if a person can't attend our conferences yet, because all in, by the time you fly and, you go to all the things, you know, it's several thousand dollars and we do it twice a year. And so some people just aren't ready to make that investment.
But there's lots of other ways they can engage and they want to learn. And so being on lists, signing up for workshops, things like that, and just being made aware of what's coming up, it's a real way to serve. And I, think that's part of it for me is that it feels like, [00:17:00] almost universally applicable, basically anyone who's willing to read an email, I like that part.
Mm-hmm. Mm-hmm.
Dana Casto: Yes. You know, it, it is one of those evergreen marketing strategies.
Catherine Brown: And I'll tell you my LinkedIn reason I love LinkedIn is because I love to comment and I like to comment on posts that a lot of other people didn't comment on because I notice when someone comments on mine
Dana Casto: Yep.
Catherine Brown: And I feel like if you wanna build a relationship with someone, it is one of the dearest ways to do it, and it's highly personal.
When people say they don't understand how people like LinkedIn and that it is impersonal, or they feel like they're getting trolled all the time, like, I don't know who you're following because the good humans are who are in my network. It is not like that.
Dana Casto: Right, a hundred percent.
Catherine Brown: I, I love to be someone I know on the other end.
They're going, oh, someone commented.
Dana Casto: I mean, it, it's,
Catherine Brown: We all have posts that we think will work.
Dana Casto: hit,
Catherine Brown: We all have, we all have, we all have posts we think will work, And then [00:18:00] no one responds. You know? I mean, like, it happens to the best of us, and so I'd love to be there in that way. It's really gratifying.
Dana Casto: Appreciate that about you.
Catherine Brown: Thank you. You could count on me on the, the, the less clicked on post. Okay. We probably gotta bring this home. I've enjoyed talking with you so, so much. Last question. What would you encourage.
Advice for First Marketing Hire
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Catherine Brown: Someone to think about when they make their first marketing hire. What do that person tend to do, and what would you want these small businesses listening to?
What can we tell them that will save them time and money?
Dana Casto: So the pattern that I often see when it comes to hiring is that clients or B2B service providers that I've worked with, they often hire before I.
had to really define what business success looks like and how revenue generating activities will get them here. the most expensive misunderstanding usually looks [00:19:00] like. One of two things. The first thing is they're hiring for implementation before strategy. That could be that they're hiring social media managers or website developers or designers, or they're hiring a marketing assistant. These are all doers, and don't get me wrong, they're incredibly helpful and valuable, but without an understanding what success looks like, the these could really be wasted efforts. And the other thing that I often see happen is they're hiring for relief clarity on goals, audience, or message. here's what I often recommend that they do instead,
Catherine Brown: Okay.
Dana Casto: and this is the sequence to do it. Get clarity first. Then do a strategy around what you've gotten clear about, and then you move to implementation. Otherwise, you're putting the cart before the [00:20:00] horse.
Catherine Brown: And Dana, when you say get strategy, you're saying it's just a plan. It's just developing a plan that's observing what we've learned so far and then deciding how we're gonna go after what we're doing next.
Dana Casto: Absolutely. It could be as simple as a client deciding that they want to do workshops, and so their goal for 2026 could be to do one workshop every month for the year. So 12 workshops, that's, a measurable goal, right. And then they gotta get clear about, okay, what kind of workshop and where do I need to take that workshop and who needs to come to it in order to deliver the right kind of content and attract the right kind of prospects. And around that, they can set a, a benchmark that says in order for me to feel successful about this workshop, I need 20 people to come. And so we've now just set two goals and we have a sketch of what a plan could look like. [00:21:00] strategy doesn't actually need to be any more complicated than that.
Catherine Brown: Okay, that's helpful because strategy sounds fancy.
Dana Casto: Oh, it sounds terrifying to lots
Catherine Brown: really fancy data.
Dana Casto: It's really, it's, yeah. Yeah. I so appreciate one. One of the things that brings me joy about the work that I do is demystifying what marketing can actually do for a business and what marketing actually is. There's so much misunderstanding. And marketing gets a bad rap for lots, lots of very reasonable and viable reasons. Like a lot of times marketing and strategy doesn't work. Some of that is a misalignment of expectations. Like we're gonna just think that if we have a crystal ball or a magic eight ball, we can shake it and get an answer, and all of a sudden all of our problems are gonna be solved like that.
The reality [00:22:00] is that marketing isn't a quick win. There isn't some magic wand that I can wave. There are certainly tried and true things we can do to make marketing function at a higher level for any business often rooted in. Are you talking to the right people and are you talking to them in the right way? If we get clear about those two elements, then we can translate that to a website, to email, to social, to all of the marketing and sales things.
Catherine Brown: Dana, one thing I appreciate about you is that you do want to break it down for people and demystify it and make it not scary. And some people make themself more valuable, or they perceive they're making themself more valuable by making things sound fancy and hard.
Dana Casto: Hmm.
Catherine Brown: Every business needs marketing, and it's one of the.
Lie awake at night. Very first things they have to solve for because they have to get more leads. And so I really appreciate the way that [00:23:00] you approach that.
Final Thoughts and Contact Information
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Catherine Brown: How can people who hear this podcast a month after it drops a year after it drops years from now, how can they find you so that they can learn more about how you help put plans together?
Dana Casto: Yeah, absolutely. They can go straight to my website, which is Whisper without an E-W-H-I-S-P-R
Catherine Brown: Whisper us. Awesome. And I happen to know because I'm a commenter on the Post. He's also on LinkedIn. There's some other places to find him as well.
Dana Casto: That is true.
Catherine Brown: Dana, thank you for today. I appreciate you so much. I appreciate your partnership and your friendship and the way that you help. Businesses, specifically services providers, navigate this unchartered territory.
It's clear that you love it and that you're working in your joy, and that's a good model for people too.
Dana Casto: Well, I so appreciate you, Catherine, and I'd love to leave your listeners with one final thought or one [00:24:00] nugget, which is when growth is clear and intentional, it stops being something being chased
Catherine Brown: Hmm.
Dana Casto: and starts being something they can rely on.
Catherine Brown: If we all want that,
Dana Casto: Absolutely we do. I want
Catherine Brown: I.
Dana Casto: Thank you so much, Catherine. Appreciate you.