Building Brands That Win: Drew Webb on the Affari Approach to Creative Strategy

In this episode of Making Cents of It All, Jesse Stakes sits down with Drew Webb — CEO, founder, and the creative force behind Affari, a marketing and digital innovation agency helping brands grow through strategy, design, and AI‑driven transformation.

Affari has spent more than a decade building the future for its clients — from branding and visual identity to custom websites, digital marketing, and AI‑powered search optimization. Drew breaks down how Affari helps companies tell their story, stand out in crowded markets, and stay visible in an era where AI is reshaping how people discover and engage with brands.

Jesse and Drew explore:

• How Affari blends creativity, technology, and strategy to build cohesive brand experiences
• Why AI‑driven search optimization is becoming essential for modern businesses
• The process of transforming complex ideas into clear, compelling design
• How Affari’s team of designers, strategists, marketers, and technologists collaborate to bring a client’s vision to life
• What it takes to build a creative agency that has been “creating the future since 2011”

Drew shares the real founder story — the early days, the evolution of Affari’s capabilities, and the mindset required to lead a team that helps clients envision a better future and actually build it.

If you’re a business leader, marketer, entrepreneur, or someone fascinated by the intersection of creativity and technology, this conversation delivers insight into how brands grow, adapt, and thrive in a digital-first world.

Tune in and make cents of it all.

Transcript

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Jesse Stakes: Hey everybody, welcome to this week's episode of Making Sense of It All. I'm your host, Jesse Stakes, and I am pleased to bring you Drew Webb. He is the founder and CEO of Afari. Drew, thank you so much for joining me.

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Drew Webb: It's a pleasure to be here. Thanks for having me.

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Jesse Stakes: So, high level, before we even get into anything, tell my audience, what is Afari?

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Drew Webb: Afari. Afari is a digital creative firm. We do marketing, branding, web design, and development, so we're kind of an all-inclusive, one-stop shop for companies, to take their brand from start through marketing,

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Drew Webb: And try our best to keep a single voice throughout the process, so they don't have to work with multiple people. So it's, it's kind of what we do.

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Jesse Stakes: Very cool. The first thing that comes to my mind when I hear the name is Safari, like, is there any kind of a… like, where did the name come from? I'm just absolutely curious.

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Drew Webb: Yeah, that's a fair question. We get it quite often, and it has nothing to do with Safari.

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Drew Webb: We get the Safari project or the affair project, which are the two mess-ups most people give us. But no, so Afari is actually, like an Italian term for business.

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Drew Webb: So we're the business project, and our mission was always to work with companies, businesses, to bring their story to life, and to try to tell their story.

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Drew Webb: The reason we always left the word project in it, is because, I think most people

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Drew Webb: If you think about, like, a project, it's something, like, you are passionate about, like, around the house, you have projects and you have chores. And so we've always viewed, like, our clients and the businesses we get to work with as projects.

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Drew Webb: Things that we like to do, things we choose to do, not things we have to do, so…

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Jesse Stakes: It also sounds pretty cool when you call something a project, too.

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Drew Webb: Yeah.

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Drew Webb: So it's good. It works out well. So, that's kind of the mission behind the name. The next question everyone always asks us is, why an Italian word? And I was like, well, because it sounded cool. Yeah. We do marketing, and it sounded cool, so, yeah.

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Jesse Stakes: So, I'd love to… let's take a step back a little bit. Like, what kind of, you know, I'd love to learn what brought you to founding Afari. Like, was it something that you always wanted to do? Was it something, like, marketing was kind of that… that was your end goal, or what got you here?

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Drew Webb: No, honestly, I never wanted to run a company, ever. It was my mission to not do that, in life, and yet here I am.

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Drew Webb: So, what brought me here? I, in college, I studied kinesiology.

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Drew Webb: So I tried my best to stay away from business altogether. My dad back in the day was like, you should take a business class, and I was like, nope, not doing it. And then I got my master's in public health, in, administration, so it kind of was my first, like, touch into the business world, but kind of like a gentle.

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Drew Webb: Nudge that direction, but not… a full mission by any means. And so…

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Drew Webb: What got me here? I had a nonprofit that I ran in college, for about 7 years, and during that time, I worked with, a designer who was trying to work on his college thesis.

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Drew Webb: And so we became part of his design, like, final senior project, to brand, the nonprofit that I had at the time.

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Drew Webb: And he and I became fast friends over the course of years, and

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Drew Webb: And then a few years later, he was like, I want to start a marketing firm. And I was like, well, I have zero history in that world.

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Drew Webb: But, I'm happy to run the business side. And so I stepped in and jumped into the business side of that with him. He ran the design, he was a creative director and developer, and I just ran the administrative side of the company, and…

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Drew Webb: Over the past 15 years, we grew a fari, to where we are today, so…

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Jesse Stakes: It's very cool. I mean, it's… was there a particular gap, or was there something that you guys saw that you could fill at the time, or was it just, you know, just organic growth?

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Drew Webb: A little bit of both.

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Drew Webb: I obviously, I came from the nonprofit side of the world, and we…

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Drew Webb: In that side of the world, you really have to get your story told well in order for people to, like, understand what you do, and for people to give money to it. And so, crafting the story and getting people to engage with a story was so critical, in what we did in the nonprofit world that

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Drew Webb: our goal was to bring that same kind of idea to more nonprofits, and make it approachable, and make it affordable. Nonprofits don't normally have big budgets, and so our hope was to be able to bring

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Drew Webb: that storytelling ability, that creative side, and bring it to nonprofits in a way that they could afford it, and be able to reach people, in a bigger way. And so, that was kind of our mission from the beginning. We've grown bigger than

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Drew Webb: grown outside of nonprofits, but we still do a lot of work with them to this day, and it's kind of our passion, still to this day, and then we get to have bigger clients that help, you know, build a team around. So, it works out well.

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Jesse Stakes: Very cool. I think that it… I mean, nonprofits and business development, for nonprofits, it's all storytelling. I mean.

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Drew Webb: Oh, yeah.

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Jesse Stakes: They got a mission that they're trying to fulfill, or they're trying to, you know, solve one of the world's problems, and if you can't tell your story, if you can't… if you can't articulate and narrate that vision that you have.

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Jesse Stakes: I guess you could say that about all business, but especially in nonprofits, because there's really nothing tangible that you can… aside from your story, and aside from the way that you present your story, whether it's through pictures, videos, and narration, you don't have anything.

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Drew Webb: Yeah, in nonprofits, it's, you are… you're kind of, for lack of a better way of saying it, kind of tugging people's heartstrings.

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Jesse Stakes: 100%.

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Drew Webb: And so, your goal is to tell your story in an engaging way that people can

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Drew Webb: kind of connect with in a way that they don't normally do with businesses, usually. Obviously, with businesses, you still want your customer to connect, but in nonprofits, it's about someone who is passionate about what you're passionate about, or has a connection to it in a way

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Drew Webb: That touches their life, and so it's trying to tell your story in that way. So it's kind of what our mission has been over the years, was to create

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Drew Webb: Brands and stories and messaging for nonprofits that would, draw people to them and allow them to, to kind of build their base from that, so…

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Jesse Stakes: Yeah, I mean, I think you're answering this question as we go along here, but I'm gonna ask you anyways. What do you feel differentiates Afari from your competition and from other firms that are in marketing? Because I know it's a very competitive space.

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Drew Webb: Oh, yeah. You can… you can throw a rock and hit a marketing firm. Or two or three. And so, yeah, it's definitely a very crowded space, but I think at the end of the day, though, as much as there's a lot of firms out there.

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Drew Webb: our biggest hope is that we just get to connect with the right people, and that we get to tell the story of people that are looking for it under one roof. What sets us apart? I don't know that every… I think every marketing firm kind of has, at their core foundation, the goal to…

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Drew Webb: you know, grow a business, a client.

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Drew Webb: I think from our side, our goal has always been to form a, like, a relationship with our clients in a bigger way, and not just be

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Drew Webb: you know, the, like, transactional company that they go to, but to always be available to them, more on a, like, a relationship level. It's a culture thing. I think for us, our biggest goal is to get to know our clients in a really personal way, get to know what they're doing.

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Drew Webb: Who they're trying to reach out to, what the heart is behind their company, and then really work with them to,

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Drew Webb: To explain that to their audience in a way that has never been done before.

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Drew Webb: And obviously using platforms that every other marketing firm uses, but to hopefully use them in a way that is a bit more engaging, or a bit more, storytelling type approach. Clients… clients want to be heard as much as they want their…

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Drew Webb: Their audience to be found, and so our

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Drew Webb: goal is to connect with our clients and get to know them on a really personal level. Afari has been a 100% remote agency since we started, and so our clients are all over the U.S, and so we

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Drew Webb: The nice part about that is we always have a team member within a little bit of distance from our clients, and so we try our best to, like, get to know our clients, no matter where they are in the U.S, in person as well. So we'll travel to them and get to know them and, kind of get to… to feel who they are, and who their clients are, who their audience is, and…

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Drew Webb: Do that in a real tangible way, so…

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Jesse Stakes: I, I think one of the biggest things that… that I think… People do business with people.

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Jesse Stakes: People, I mean, it doesn't really matter what the name of your company is, if you can't connect with somebody on a personal level, and if they can't relate to you, and relate to the people that work for you.

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Jesse Stakes: It's difficult to do business on a long-term basis. I mean, you said the word relationships, and I think it… I think the word gets abused a lot in business.

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Drew Webb: For sure.

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Jesse Stakes: And it's… and I think that, you know, people forget, what is a relationship? What does that actually mean? What does that look like? And I think you just described it incredibly well. The fact that you're… you're not just looking to try to fill a, you know, a demand from your client or a request.

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Jesse Stakes: You're trying to, you know, ingrain yourself in their business. You are… you become a part of their business. You truly become a partner in a lot of ways.

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Drew Webb: It's always been… our goal is to almost function as an in-house marketing pers- er, team, or in-house marketing firm, or in-house design team.

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Drew Webb: So that we feel like a part of their company from the beginning. We want our clients to treat us as though we are in the cube next door, or down the hall from them.

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Drew Webb: we're always a call away, we're always a text away. A lot of our clients have my phone number, so they'll just text me, like, hey, we got a question. I'm like, cool, no problem at all. Let me get you connected with, a team member who can actually bring that to life for you. And so, our goal is always to be that approachable

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Drew Webb: down the hall part of your team, so that you don't feel like you're reaching outside of your organization. In fact, we try to get to know your company as well as you know your company. And that way, when you talk to us about what you do, you can talk about it the same way you would talk about it

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Drew Webb: with someone else within your company, so that there's no loss of voice, or no loss of message when it comes to what we then take to your audience.

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Jesse Stakes: Yeah. I always tell people, you don't want to be a bad game of telephone. When you're working.

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Drew Webb: No. When you're working.

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Jesse Stakes: in between them and their audience, or them and their customer base, you cannot be… you can't be bastardizing the message. You gotta do… you gotta do a very good job of retelling their story, just with a lot of polish on it, and, you know, with a better coat of paint on it.

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Drew Webb: And it's a huge responsibility, too, at the end of the day. I mean, that company, or that nonprofit or that organization is looking to you to tell their story, and that's a huge trust that they've put in us.

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Drew Webb: And if we don't take the time to get to know all about them, and what they do, and the way they function, and…

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Drew Webb: the way they want to talk to an end, you know, audience.

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Drew Webb: then… then we're doing them a disservice, and so it's our job to get to know their business as well as they know their business, so…

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Jesse Stakes: No doubt. So, I'll ask the flip side of this, because I think it's as important as it is to know who you want to do business with.

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Jesse Stakes: it's also important to know who you don't want to do business with. So, you know, as you were growing this company, or as you, you know, even now, as you guys have been established, you know, people love stories. They'd love to hear any kind of stories. You can change the names of the, you know, to not impact the innocent, but have you had any stories where you had to fire a client?

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Drew Webb: Yeah.

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Drew Webb: Yeah, we have. And it's funny because that client…

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Drew Webb: we would work with again today in a heartbeat. And that's a weird thing to say. I didn't… we didn't let a client go in the past. One of the biggest ones that comes to mind is we partnered with another design firm, actually.

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Drew Webb: For the very first 3-4 years of our existence, as an agency, we became a support to a client who had big, big client names. Which for us was great, because it allowed us to have those clients in our portfolio.

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Drew Webb: Which was a fantastic stepping stone for us. But at the same time.

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Drew Webb: That client became very quickly

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Drew Webb: 50-60% of the revenue at Afari, and became a huge part of, the demand on my team in a way that limited us from bringing in new clientele.

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Drew Webb: And so the only reason we kind of separated from them was only… was… had nothing to do with the relationship. And my mission during that period of time was to maintain the relationship. In fact, I think one of their directors to this day, he and I still talk, and we still message, semi-regularly.

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Drew Webb: When we can. I'm still trying to look for projects that we can team again on.

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Drew Webb: But we separated because… It was,

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Drew Webb: it was holding back the potential of what we wanted to do as an agency, and it also was a risk because if we didn't have them as a client, we lost 50% of our revenue. So, for me to be able to make the decision to say, hey, we're gonna step back.

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Drew Webb: because I need to bring in clientele that isn't as volatile or isn't as potentially damaging if you do walk away from us. We made that decision at a period of time that we knew we could afford it, and also had enough in the pipeline to bring in to cover it.

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Drew Webb: You know, instead of having 50% of my revenue from one client, we then were able to spread that over costs of 10. And so that way we had 10 new clients, but also we had… the risk of losing one of them was a tenth of an impact on our business. And so at the end of the day.

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Drew Webb: That client brought us some of the biggest names in, like, footwear and sports, which was great, but, you know,

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Drew Webb: It also brought the risk of, you know.

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Drew Webb: you know, a loss of revenue that would have been detrimental down the line had we, you know, not planned for it accordingly. So it was a need to step back, and I don't know that we necessarily fired them, we just had to have that conversation of, like, hey.

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Drew Webb: We can't deliver this much work for you on a regular basis without

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Drew Webb: Either completely scaling my team to a place that put us at risk, or…

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Drew Webb: setting clients aside that we already had in our workforce, like, in our workflow, and prioritizing only this one. And so it was just kind of a conversation of, like, hey, we need to, like, take less from you, not just not work with you, if that makes sense, so…

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Jesse Stakes: Makes perfect… makes perfect sense. I mean, it's…

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Drew Webb: Yeah.

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Jesse Stakes: the challenge of concentration, I mean, as far as whether it's in people's accounts receivable, or if it's in the work that you're, you know, that you're actually bringing in from your sources, it can be very dangerous. I mean, it can affect… I mean, I've seen very successful $100 million companies go out of business

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Jesse Stakes: you know, not overnight, but over a… over the next 3 years after they lost an enormous contract that represented 70-75% of their work, because they put all their eggs in one basket, basically. And then when they… if they do that for a long enough period of time, they forget what it looks like to go out and chase in new business, too. They forget what it means to add new logos to their… to their list of customers.

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Jesse Stakes: So, I mean, I have seen it. I've seen it on the flip side of it. I've seen it where companies are also…

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Jesse Stakes: They're trying to leverage

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Jesse Stakes: their business, as far as who they have in their customer base, and how much business they have coming in, in order to borrow money, and it's the same kind of a thing. Banks look at it as an incredible risk when you have all your eggs in one basket, or in a couple of baskets, you know.

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Jesse Stakes: It's the what-if, it's that… it's that… it's always the what-if the worst-case scenario happens, and if it does, if the answer is that you go out of business, I mean, kudos to you for recognizing that before you got to a point where it was a hard pivot, that you did it when it was an easier pivot to make.

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Drew Webb: And we did it when our team was smaller, and I think that was an important move at the time, because it was either hire 2 or 3 more people to cover this one client, but if that client left, then I'd instantly have to fire people, which was not something I ever wanted to have to do.

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Drew Webb: Or it was say to the client, hey, we've got to step back, because we need to grow…

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Drew Webb: this other side more organically, and take on clients that are… have been asking, or that we have kind of said, hey, we're on a 4- or a 6- or an 8-week, delay on kicking off your project because of what we have in queue.

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Drew Webb: And so it was… I think the timing was…

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Drew Webb: to our advantage, because we weren't large. And I think that's something we've always tried to avoid at Afari. I mean, I've never wanted to grow a firm so fast that, we were at risk of having to fire people or hire simply to cover one contract.

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Drew Webb: And I think that's something I can safely say. We're not a huge agency by any means. I've always tried to keep it at a fairly, tight-knit group of people.

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Drew Webb: But that has allowed us to be nimble through tougher times. It's allowed us to be able to, you know, take the clients that we love, versus taking clients just because we have to.

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Drew Webb: And I think it also allows our team to have the stability. We hire full-time team members, we don't contract out ever, and that's because I've always wanted my team to not worry about where their next paycheck came from, I wanted them to worry about the project that was ahead of them.

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Drew Webb: It's on me and our, Director of Growth here now at Afari to find clients. That's our goal.

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Drew Webb: It's my team's job to deliver, and to focus on being creative, and not having to worry about it. And so, over the course of…

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Drew Webb: 15 years, we've never in the history of Afari had to let someone go because of staffing or because of a lack of work. Because we've only ever staffed when we knew we could support that person for the future, so…

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Jesse Stakes: I think that's fantastic. It really speaks to the… to your leadership style, and it speaks to kind of the culture that you're… that it seems like you're instilling in your organization.

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Jesse Stakes: question I have around that, because you said you guys are 100% remote. Like, is it difficult? Like, does it make it difficult to instill a culture or, like, an intentional culture in your employees?

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Drew Webb: Yes, yes and no. So, my business partner, my… the one I started a fari with, who… who isn't with us anymore, but who I started Afari with,

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Drew Webb: he was based out of California. I'm here out of, Hampton Roads, Virginia. And,

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Drew Webb: And so we were about as far apart as we could be. We also started the company having never met each other in person.

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Drew Webb: We were friends for years, just by, like, correspondence and email, and we were talking on the phone, and I just had never flown out to where he lived, and we never had…

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Drew Webb: you know, spent time in person, but we had formed a relationship as friends, you know, over a distance, and so it allowed for that to be the norm, and so as we looked at bringing on team members.

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Drew Webb: We brought on team members no matter where they were, but because we wanted them to be the most creative. We're a creative agency. I want people to live where they feel inspired.

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Drew Webb: Not to be forced to live in a place that could… could inhibit or hamper, their creativity in any way, and so…

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Drew Webb: We've always done it in that way. I, over the years, have always traveled to team members to ensure that we get to know them. Whether they are local to Hampton Roads or to wherever we might be, with, my current business partner lives in Montana, he's been with me for…

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Drew Webb: 10 years now. And so a lot of our team members are both based out of Virginia and Montana, but we also have team members in North Carolina and Iowa.

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Drew Webb: Oregon, Texas, I'm probably forgetting a state, so…

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Drew Webb: I'm gonna apologize… Colorado. I knew I was forgetting one. And so, you know, we… it also is a benefit to our clients, though. Our clients love having, a team that spreads all…

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Drew Webb: you know, time zones of the United States. We're able to work East Coast or West Coast time seamlessly. Our PM team are both East Coast and West Coast, and so we're able to

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Drew Webb: handle client comms in a really efficient way. And our team, we try, like I said, we try to meet up, so anytime we have a few people in a close proximity, we'll gather together.

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Drew Webb: Or I'll fly out to Montana, or I'll fly out to Texas and meet with our team members accordingly. So it's… it's, and there's a big Slack conversation at all times at Afari, so, there's, yeah, there's a lot going on still, no matter what, at all times, so it's good.

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Jesse Stakes: It seems like, I mean, there are people a lot in different types of businesses, whether it's the finance business or in construction, all kinds of stuff, they're having to make a big shift right now with the way that the economy is changing, with the way that.

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Jesse Stakes: modern technology is changing. It really seems like you guys were kind of a… kind of before the curve. Like, you were identifying that this was just by choice, the way that you guys wanted to work and the way that you wanted to organize your company, but it really has worked out in a way that you guys were in front of the curve and doing it before it was cool, basically.

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Drew Webb: Yeah, it's… it's funny, because…

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Drew Webb: a lot of companies, a lot of agencies went through a bit of a transition. A lot of companies, every company, let's be real almost, went through a transition to COVID, when we went through that whole process, and…

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Drew Webb: People couldn't go into the office, and so remote became the standard, and…

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Drew Webb: A lot of agencies didn't have the tools in place to account for that, and we saw a lot of fluctuation in agencies and the way they communicated with their clients, and a lot of clients left agencies during those times, because those comms weren't really in place, because it wasn't something of a standard at the time.

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Drew Webb: During that period for us, our clients saw no change in the way they interacted with us, because that's how they'd interacted with us for years before that, and so…

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Drew Webb: that shift was actually really not an impact on our team. I went from working at home to working at home. So, and so did every single one of my team members, and so…

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Drew Webb: there was no shift in our productivity, there was no shift in our creativity, during that period of time, and our clients noticed that. And so, it actually was a period of growth for us, which was nice, instead of, like, a period of pulling back.

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Drew Webb: We ended up hiring a few more new people during COVID, which was not the norm, I feel like, for a lot of companies. And it allowed us to continue to deliver for clients in a bigger way, because they were…

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Drew Webb: you know, not used to having to be remote, and so they were used to working with us remote already, so they sent us more things that they didn't know how to handle internally, so it…

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Drew Webb: Definitely, I felt like we were a little ahead of the curve in the moment. I think today, you know, we're watching companies kind of forced to going back to work, which I'm interested in, because I'm like.

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Drew Webb: you… you didn't see a loss in productivity. In fact, you probably, when your team members are happier.

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Drew Webb: The work they put out is better. So, I'm a big fan of working wherever you are.

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Drew Webb: however you want to. And being able to be creative wherever you are, so it's nice.

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Jesse Stakes: I think it's fantastic, especially for creatives. Like, for people who are in a creative industry, I think it works well. I have seen where it is challenging when you have people in, like, a customer service, like, type-oriented job, or when they're expected to have a level of productivity,

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Jesse Stakes: I've seen where that has fell off, when people went home to work, and it's like, they were throwing the laundry in all the time, they were catching whatever the daytime programs were, like, anything they could avoid, but I agree with you 100%. When your job is creativity, and you enjoy what you do, and you're passionate about what you do.

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Jesse Stakes: nobody has to clock you in or out. You're gonna wanna do your job anyway, so…

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Drew Webb: Yeah.

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Jesse Stakes: Question for you then, you know, I mean, like, we talk about you being in front of the curve going into that, but the future, like, when you look over the next 3 to 5 years, or even further than that, you know, we've got so many things that are on the horizon, whether, you know, people… people… AI is a buzzword. I mean, a lot of it is

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Jesse Stakes: A lot of it's automation, what is happening right now, but there is going to come a point at which AI does start to, you know, act on its own, or actually truly act as intelligence, not just an automated prompt that we're giving it. You know, what do you see as the future of your company? Where do you see Afari going?

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Drew Webb: It's a good question, in all honesty, because AI is…

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Drew Webb: it's coming in quick. I feel like a year ago, we knew it was there, but it wasn't as much of an impact. Six months ago, or even 8 months ago, you would use Google to search for something, and you'd see the, like, AI automated response of what it found, but it wasn't, like.

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Drew Webb: well detailed or super helpful. And so you kind of ignored it. And just in the last 6 months, they have honed it in in a way that

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Drew Webb: Most people aren't scrolling past it. They're literally searching for stuff through AI search, whether it's.

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Jesse Stakes: through their.

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Drew Webb: on ChatGPT, or through Claude, or through, you know, Google's automatic AI overview,

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Drew Webb: And we're watching it shift. In fact, we're having conversations with our clients right now. I mean…

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Drew Webb: our clients are seeing more engagement than ever at times, because we're making a shift for them on a marketing side, in a big way with, an expanse on SEO, so a lot of this new AEO and GEO world, which is… it's a lot of acronyms, but ANSWER and Generative Search.

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Drew Webb: So it's that piece. It's, hey, I'm gonna go to ChatGBT and ask a question, and…

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Drew Webb: At the end of the day, is your site or is your brand visible to ChatGPT? And that's where we're starting to see this shift, and so we're now having to say, hey, you know what? Your website's critical, but it's gonna be less traffic, which is a weird thing to tell people, because it's critical in order for you to be found.

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Drew Webb: by an AI agent, or Google's AI Overview, or ChatGPT,

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Drew Webb: But are people gonna go to you, is the question. No, because a lot of times.

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Drew Webb: ChatGPT is gonna give them an email address, or a phone number, or a way to reach out to you directly.

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Drew Webb: And they don't have to come to your site, but they found you. And so it's a… it's a weird conversation to have with people right now, as we see marketing shift, because we have to think about who's finding us, really? Is the person finding us, or is the person prompting someone to find us?

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Jesse Stakes: Yeah, yeah.

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Drew Webb: it's that second piece that we're starting to see happen more and more, and we're starting to make sure our clients are prepared for it, so…

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Drew Webb: We have a full dev team in-house, which is nice, and so a lot of this piece is the development back-end piece to websites, and so having our team be able to pair creative with a full dev team in-house, allows us to help our clients, again, in a very comprehensive way.

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Drew Webb: That a lot of agencies aren't able to do, which is nice, so…

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Jesse Stakes: I think a lot of… you know, what comes to mind, I mean, because it's… you've got so many professionals, intelligent professionals, or intelligent owners of companies, that…

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Jesse Stakes: They haven't either taken the time to learn this, or it's something that has happened kind of beyond their educational years, or, you know, it's in their adult… they have to commit to adult learning to catch themselves up on this, and a lot of the times, confused minds say no.

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Jesse Stakes: And it makes me think about the whole shift when Amazon kind of took, you know, kind of took a large piece of business from Walmart.

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Jesse Stakes: Or they, you know, you essentially… some of these, like, clothing manufacturers almost went obsolete when they said, nope, we're staying brick and mortar. And it's, like, there's a huge shift in the market that's happening right now, and unless you ca… as a business owner, if you don't work with people that are making sure that you are…

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Jesse Stakes: That you are on those searches, that you are being found through those tools.

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Jesse Stakes: you're gonna be Walmart, or you're gonna be a… I mean, I think of it locally, in my area, there was a place called Steinmart. Fantastic clothing shop, was around for years, gone now, doesn't even exist. That's true.

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Jesse Stakes: Yeah, and so it's… I mean, I think that there are things that you have to address, whether you want to or not. If it's, you know, confused mind says no, but it's like… but you gotta get beyond your… you gotta get past your own confusion, or past your own fear and doubt of it, or just lack of understanding.

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Jesse Stakes: And find some… find someone like yourself that you trust, and actually engage with it, and, you know.

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Jesse Stakes: Bring yourself up to speed, and bring your company up to speed.

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Drew Webb: I mean, we've seen it, I mean, year after year, decade after decade, and you mentioned a couple good ones, but, I mean, the other most obvious ones of recent, I think.

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Drew Webb: this generation doesn't even know what Blockbuster is, which was, you know, pre-Netflix, and so there was the elimination of Blockbuster, there was Kodak back in the day, which digital… they didn't go digital, and so here they are, a defunct company at this point. And so.

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Jesse Stakes: hurt Rochester, New York, very badly when they went out of business.

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Drew Webb: Yeah, I know, I know. And so… It's interesting because…

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Drew Webb: there's always going to be businesses that don't see the shift, or don't see it soon enough. And I think that's the key, is you have to see it soon enough.

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Drew Webb: To adapt. I think what we're trying to do with our clients right now is stress the criticalness of, like, hey, AI may not be a part of your world at all. Maybe you're a professional service company who, you know, is a law firm, or a CPA firm, or maybe you are…

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Drew Webb: you know, a firm that is a nonprofit that, you know, runs as a conglomerate of funding from other big organizations. Either way, AI is going to affect the way people find you, see you, or interact with you at some point over the coming

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Drew Webb: You know, 3 to 6 months, and if you're not preparing for that, if you're not preparing to remain visible to people, then you'll be very quickly invisible.

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Jesse Stakes: 100%, I couldn't agree with you more. I mean, I think that it's absolutely… and I would say even the industries that you named.

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Jesse Stakes: AI is affecting their business in some way, fashion, or form. It is not… it is not being unaffect… it's not unaffecting any industry at this point. I think it's touching everything.

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Jesse Stakes: 100%. Before we wrap up, I've got some rapid-fire questions for you that I want to hit you.

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Drew Webb: Oh, boy.

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Drew Webb: Sure.

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Jesse Stakes: Best advice that you ever received?

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Drew Webb: Love your job.

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Drew Webb: Love your job. My dad said that to me at a young age, especially when I told him I wasn't gonna take over his company. He was like, that's fine, just love what you do.

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Drew Webb: Because if you do…

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Drew Webb: You know, the cliche is you'll never work a day in your life. That's a lie. I work every day, but I still love my job. But it makes it worth it. It makes it worth it.

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Jesse Stakes: No doubt.

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Jesse Stakes: Book a res… book a resource that changed your thinking.

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Drew Webb: Oh, boy. You know, most recently, and this is just a… it's a resource,

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Drew Webb: And it's funny, so…

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Drew Webb: The last couple years, I've been attending, this event, up in DC, and it's been around AI, and they've been running it now, I think, for 3 years, and it was before AI became even where it is today.

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Drew Webb: And it's an event that is typically free, it's called Axios. I don't know if you've ever heard of Axios, the news, they have an AI event in DC and New York, and in San Francisco. And it has been the most enlightening,

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Drew Webb: conference every… I go to it every year, and it is where they pull big companies in, and their CEOs, or their CFOs, or their CTOs are there, and you just get to, like, sit and listen to, like, how

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Drew Webb: the world is shifting, and I think that's, for me, like, where we pull a lot of our, like, okay, we have to adapt. These are what's coming, whether they've seen it 3 years ago, or we're seeing it today, or my clients might feel it in 6 months.

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Drew Webb: It's an event that we've been, a big part of over the… or been attending, not a big part of at all, but attending, the last couple years, and it's been extremely enlightening just to help navigate where we're heading over the next 5 years, so…

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Jesse Stakes: That's excellent. Do you have any one habit that you feel like has made you a more effective professional or person in your day-to-day?

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Drew Webb: One habit. One habit.

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Drew Webb: Oh, lordy, that's a good question.

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Drew Webb: I start by, well…

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Drew Webb: I start my day with a run and email. It's a weird thing to say. I used to run a lot. I used to be a long-distance runner. I still miss it. I can't do it as much. I had Achilles surgery a couple times, and it's kind of slowed me down.

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Drew Webb: But I still use that time in the morning to go for either a long run that turns into a walk, or just a long walk. And, by the end of it, I've gone through every email that I didn't get to the day before.

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Drew Webb: And I've cleared out my inbox so that when I sit down at the desk, what I can do is something that I know I either need to do, or something I'm excited to do for a client. And I don't have the stress of something, looming, and so my mornings are…

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Drew Webb: get up, go for a run, get my email knocked out before I even get back to my desk, so that I can sit down ready to go, or it's group conversation, conversation with a team member.

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Drew Webb: And I can put my focus on them, and not something that's looming behind me, so…

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Jesse Stakes: I think that's… I think that's fantastic, and… and I… honestly, I could be… I could… I could…

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Jesse Stakes: I could do without the run, I can tell you that. I'm not a run for fun guy, but I absolutely could do with the second part of that and make sure that all my stuff is knocked out from the day before, before I start the next day. I think that's a fantastic piece of advice. You know, it's funny, I think your story is one of entrepreneurship, whether you wanted to be one or not when you were younger.

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Jesse Stakes: You absolutely are now. And so, I think that, you know, if that's inspiring to anybody who's listening, you know, the fact that maybe they didn't see themselves as something when they were younger, but it doesn't mean that you can't evolve, you can't change, or you can't just reshape your thinking, and realize that something is for you.

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Jesse Stakes: when maybe you thought it wasn't before. I think that that's a… I mean, I think that that's tremendous, and I think that a lot of people can… can…

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Jesse Stakes: Can, benefit from being willing to change, or willing to accept that maybe something isn't what they thought it was.

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Drew Webb: Fair. I, I don't know. I don't… I'm probably the worst person to talk to about it. I don't consider myself an entrepreneur, even though that's what I do, and that's what I've done over the years. Yeah. I see it more as just, it's more of a passion project, but I think that's what most entrepreneurs have, are passion projects, so… No doubt. I guess it works, so…

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Jesse Stakes: I got one more question for you before we wrap this up. The hat.

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Drew Webb: Yeah.

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Jesse Stakes: You've got it on… you've got it on your profile, you wear… you've worn it every time we've spoken.

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Jesse Stakes: You gotta… there's gotta be a story behind it.

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Drew Webb: Well, I've worn hats for a long time.

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Drew Webb: Well…

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Drew Webb: Mostly ever since I went bald. But that's not because of being bald, I have no problem with that. It's because I have a, I don't know, family history of, like, skin cancer and stuff, so I've just been overly paranoid about burning the top of my head.

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Drew Webb: So, long story short, a good, good friend of ours, about 5 years ago bought me one of these cloth hats.

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Drew Webb: And it has become…

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Drew Webb: probably one of the most recognizable thing about me over the past 5 or 6 years, to the point that, yeah, it's in my profile, and I think I have 3 different designs, and they get interchanged for, for meetings and calls, so…

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Drew Webb: My hat collection is, next level, and to the point that we have, like, 4 hat racks through the house that are all full, and it's a problem. So, it's a real addiction.

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Jesse Stakes: Nice. Well, that's fantastic. If… if people are interested in what they've heard about Afari and yourself, what's the best way for them to get ahold of you?

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Drew Webb: just shoot me an email, drew at Afariproject.com. Fantastic. So, super easy. I'd love to talk to them, see how we could hopefully team with them, or be of service, or just even just have a conversation. You don't even have to use us. I'll happily jump on a call and just chat, so…

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Jesse Stakes: Now, that was… that's fantastic. This has been great. I've… I feel like I've learned a lot. I think your… like I said, your story's tremendous. It's inspiring.

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Drew Webb: Thanks.

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Jesse Stakes: So, hopefully we'll get to catch you down the road again.

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Drew Webb: I love it. That sounds great.

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Jesse Stakes: Alright, take care.

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Drew Webb: Thanks, Tessie.