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The Marketing Agency Leadership Podcast

Apr 1, 2021

Ashley Logan is the Founder and CEO at Yakkety Yak, a full-service purpose-driven content marketing agency that provides blog writing, social media marketing, video production, and website design and development for brands and organizations that want to make the world a better place. 

Ashley says that the agency’s “sweet spot” is content creation and storytelling. She believes alignment with the greater good and “giving back” are two things that are necessary for changing the world. “You have to be purpose-driven,” Ashley says. “You have to stand for something.”

A writer from age 5, Ashley graduated with an undergraduate degree in creative writing and landed a job selling for a private label candy manufacturer. She was  “a creative person trapped in a corporate world.” As she traveled around “slinging candy,” Ashley saw that widely different companies used the same words talk about themselves in the “digital space.” She decided she wanted a “bigger ticket” career and moved to commercial real estate. 

To appease her creative drive, Ashley volunteered and created content for nonprofit organizations. Social media platforms were just starting to rise. She wondered, “How could you turn those social media engines into a marketing machine?”

In 2012, Ashley finally understood that she needed to combine all of her “passions for business, storytelling, content, and nonprofit work.” She went back to school to pursue a master’s degree in Journalism in a program renowned for teaching people how to write for target audiences. 

Ashley officially launched Yakkety Yak in 2014 and took clients as they came . . . until she realized she could no longer tell stories and work hard for jerks. The agency now maintains a focus on content and storytelling for a far more restricted clientele: 

  1. Organizations that “do good” (nonprofits), 
  2. Have, as a component of their organization, the intention of “giving back” (perhaps a part of the company raises funds to donate to non-profits), or 
  3. Are amenable to adding a “do good” component to their organization (Yakkety Yak works with these organizations that do not yet have a purpose-driven mindset to help them define and build that “piece” into their company culture). 

Ashley thinks it is important for its clients to inform people of their “contributions to the greater good” by “putting it out there in your story, putting it on your website, weaving it into your social media, holding your teams accountable, and shouting it from the rooftops.” She thinks high quality video will become an increasingly more powerful marketing vehicle.

Ashley is working with a designer to “revamp” Yakkety Yak’s office space with improved ventilation and flexible seating and intends to “open the doors” after Memorial Day. Ashley sees “the new office” as a safe place where “people can come and work if they want to escape” and gradually get people back together with flexible hours and a combination of in-person and remote work. She misses the “vibration” that comes from having a “team all together” but also notes that COVID has done wonders for work-life balance.

Ashley is best reached on the agency’s website at, where visitors can find links to all of the agency’s social channels.

Transcript Follows:

ROB: Welcome to the Marketing Agency Leadership Podcast. I’m your host, Rob Kischuk, and I’m excited to be joined today by Ashley Logan. Ashley is the Founder and CEO at Yakkety Yak based in Chicago, Illinois. Welcome to the show, Ashley.

ASHLEY: Thank you so much. I appreciate you having me here.

ROB: Absolutely. Why don’t you start off by telling us about Yakkety Yak and what makes the firm unique?

ASHLEY: Yakkety Yak is a full-service content marketing agency based in Chicago. We do everything from blog writing, social media marketing, video production, website design and development – basically any mechanism to help our clients tell their stories, we work with them. I guess what makes us unique is that we focus on working with brands and businesses that care about doing good. We’re a totally purpose-driven agency working with brands and businesses that want to make the world a little bit better.

ROB: What does that look like when we actually get down to a client? What does a client look like who has this purpose-driven focus? Are there maybe some examples you can share of how they’re getting out in the world?

ASHLEY: Absolutely. That can be nonprofit organizations, of course. They fall into that category. We work with many patient-facing organizations like the American Migraine Foundation, the American Brain Foundation, and other brands in that category. But purpose-driven doesn’t have to be nonprofit; it can be an organization whose culture focuses on giving back. They have volunteer events where they donate proceeds to a nonprofit organization.

Ultimately, that alignment with a greater good is our sweet spot because one, it helps with storytelling, but also, in this day and age, giving back is such an important part of changing the world, making it a little better.

ROB: Finding that sort of specialization and alignment can sometimes be a journey. How did you come to focus on that as a specialty?

ASHLEY: That’s such a great question. When I founded the agency back in 2014, we didn’t have the luxury of selecting the types of clients that we worked with. I’m sure you’ve heard this a lot with your guests. We worked with some people that we probably didn’t want to work with. Ultimately it came down to that if we’re going to tell stories and work hard, we don’t want to work with jerks. [laughs] So we didn’t. We stopped working with jerks, and that’s it in a nutshell. Is that terrible?

ROB: No. I mean, who wants to work with jerks? I don’t know anybody who says they do. I haven’t heard that strategy yet. I’d be fascinated if we have somebody listening who has a strategy built around working with jerks and charging a premium for it. I’m here for that conversation.

ASHLEY: [laughs] I love it. So that’s really what it came down to. We also help businesses who don’t have a purpose-driven mindset to build that into their company culture. Maybe they came to us and wanted to think about “How do we put our story out there in a way that has more employee retention, that we can attract more visibility from our clients?” We always say you’ve got to be purpose-driven. You’ve got to stand for something. So, we’ve also helped coach our clients into getting into this space, too.

ROB: What does that transformation look like? Maybe an example of where a company was starting. The purpose is usually there, much like your own firm; you just have to find your way to it.

ASHLEY: That’s exactly it. Just setting the intention, putting it out there in your story, putting it on your website, weaving it into your social media, and holding your teams accountable too, and just shouting it from the rooftops. That’s especially applicable to clients of ours that aren’t necessarily nonprofits but are doing something to give back – make sure that their employees know about the work they’re doing at an executive level and then down to a grassroots level. A little bit less in COVID time but coordinating fundraising events or teambuilding events around giving back.

ROB: It sounds like it would almost pull you towards being involved in – if an organization didn’t have core values, you might not even be working on marketing. You might be working almost on their internals before they get to the externals. Do you end up getting pulled in that deep?

ASHLEY: Sometimes, yes, we do. But I think that primarily our sweet spot is in the content creation and the storytelling. That’s where we really like to be. Certainly, we will help clients define their brand strategy, and that includes core values and messaging. But we definitely like to focus on the story element.

ROB: Understood. You talked about not having as much of a focus when you started, but let’s even go a little bit further behind that. What led you to have the sort of audacity to create your own job and create some other jobs along the way? How did you get into that lane?

ASHLEY: I love that word. I love the word “audacious.” Let’s see, I’ve been a writer for my whole life, ever since I was in kindergarten, I think. I won a Young Authors contest for a short story I wrote called “Crystal Met the Ogre.” I still have it. Kind of funny. But I’ve been a writer my whole life, and I loved to tell people stories, but I also had a knack for business and trying to create processes and connect people.

After I finished my undergrad at University of Tennessee – I was a creative writing major; I worked at the school paper – I ended up in a sales position. I wasn’t expecting that I was going to be in sales, but also that I was going to like it so much. I started off working for a candy manufacturer based in Chicago. It was a great experience. I was 22, had half the country as my territory, was flying all over, slinging candy. But I wanted a little bit more of a high-volume sale, and I moved into commercial real estate.

Through that experience, I was a creative person trapped in a corporate world and interacting with people at the C level. What I found was that all of these brands and businesses didn’t know how to talk about themselves. They were all innovative. Every single one of them called themselves “innovative.” All of them called themselves “streamlined.” I realized it was a problem that in this digital space, people didn’t have the words to differentiate themselves from one another. You could close your eyes and hear across multiple industries and see people using the same exact words to describe themselves, with no differentiation.

So that was an observation. In the meantime, I was volunteering for nonprofit organizations in Chicago and helping them with content creation. This was that sweet spot when social media was just starting to go from being that you needed a .edu email address to that anyone could sign up for Facebook at this time. How do you turn those social media engines into a marketing machine?

I cut my teeth on that through nonprofit work and ultimately decided that I was onto something and needed to combine all of my passions for business, storytelling, content, and nonprofit work. So I left my career in commercial real estate and went back to school to earn a master’s in journalism from Northwestern University’s Medill School of Journalism. They have a great program for writing for a target audience. I simultaneously founded Yakkety Yak, and the rest is sort of history.

ROB: That’s a great upscaling moment on the writing there. I like that. I wonder a little bit – I’m just going to pull on a thread here that’s a little random, but we’ll see where it goes – if you don’t mind me asking, what was the candy? Who were you selling to, and what made it desirable for them to buy this candy?

ASHLEY: [laughs] It was a private label contract manufacturing. That’s what we pitched. I worked with Cost Plus World Market and Harry & David, and we were doing premium toffees. We would produce it for them under their own private label brand. Coming from Chicago, we’d make the candy and then it would be in like a Harry & David package, for example. They also did those really beautiful Christmas candies, ribbon candies. That was it. No chocolates and no gummies, but pretty much everything else.

It was cool. There was a factory. The CEO of the company gave me my first job out of school, tolerated me, trained me in sales. He actually passed away a couple of years ago, and he just made such a positive impact in my life, giving me this opportunity. It was pretty cool getting to walk through the candy factory and make friends with the factory workers and be part of creating something from end to end.

ROB: That’s very cool. Those are typically, in my reckoning, pretty high end, nice candies. It’s a creative process. It’s not what it sounds like at first when you say sales. I think we all sometimes miss doing tangible work, something you can put your hands on and something you can see sitting on a shelf.

ASHLEY: Yeah, it was cool. And it was fun. It was my first experience in business. We would go to these candy conferences, and I was the youngest by far. I was the only female, interacting at Happy Hour with the good ol’ boys who’d been in the business for 40 years. It was fun. It taught me a lot about how to defend myself. It taught me a lot about how to keep composure as a woman in business and overcome challenges. That experience grew me really well for commercial real estate, which was a little bit more of a cutthroat type of industry.

ROB: Right. You went from a boys’ club to a mean boys’ club.

ASHLEY: [laughs] I did.

ROB: Even trickier. Maybe a little bit gentler in a more creative space. But I think what’s interesting is the through line is, as we all know as an agency owner, you are selling, but it sounds like a common thing across your sales experience is you’re really helping people get what they want – which is much easier than trying to convince them they need something they’re not aware of.

ASHLEY: I think so, yeah.

ROB: Very interesting. Ashley, as you reflect on – you said 2014 was the starting of Yakkety Yak?

ASHLEY: I have two dates. 2012 is when I founded the agency and I went back to school, and I had a few very small clients at the time. But 2014 is when I hired my first employee and Yakkety Yak became my full-time job. So I use that as my real date.

ROB: Got it. Over the course of that 7+ year time, what are some things you’ve learned that you might do differently if you were starting from scratch?

ASHLEY: That’s a great question. My journey has been really interesting. I built the agency from scratch. I had no outside investors. I’m pretty risk positive; I’m comfortable in a space of jumping and leaping to the next level. It doesn’t make me nervous. I don’t spend a lot of time dwelling on mistakes made because I do believe that every experience leads you to the next, and you’ve got to build upon it and take with you the tidbits that help make you stronger.

For example, looking at my career trajectory, the candy business, while I knew it wasn’t my life’s passion, that sales experience helped take me to the next level. Any adversity that I faced in commercial real estate, I took that with me to become a founder and CEO and be gutsy as hell.

But one thing that stands out for what I would do differently is I think in the area of hiring. I have worn every hat in the agency, and I wish that I’d had more help sooner because that would’ve helped me scale faster.

I haven’t mentioned this part yet, but I’ve got three really little kids – and a COVID baby. It would’ve been great – when my second son was born, it was 2018; I was 38 weeks pregnant, and I had an employee resign, which meant that I was not going to get any maternity leave. I had my baby on a Tuesday and I was back to work on Monday. If I had built a deeper bench, then I would’ve been able to have a little bit more balance early on.

ROB: What do you think it was that prevented you from building up that team?

ASHLEY: I think when you’re an agency starting out and you’re competing in a market like Chicago – we have some major players here. I’m going up against, from a benefits standpoint, a salary standpoint, and a credibility standpoint, some powerhouses. It took a little bit of time to earn some credibility and name recognition. People, I will say, do remember the name Yakkety Yak, so I am proud of that.

Recruiting top talent takes time and building up a team and building that referral network where people say “Hey, that’s a place where I really want to be and where I want to work.”

ROB: Got it. What were your first couple of hires when you went from a team of one to a team of more?

ASHLEY: Oh gosh, one of my first hires was – and he’s still one of my favorite employees; he moved back to California and is doing some really great things right now – a graphic designer. I had the way with the words, and I was bringing in the business but also doing a lot of the content creation, and Curtis was doing the graphic design elements.

And then support from a writing standpoint, so I eventually started to be able to outsource that and build a team. I shouldn’t say outsource; I mean delegate. That’s the word I mean.

And finally, 2018 was a breakthrough year for me where I finally was able to build – we had more than 15 people. Now we’re a team of 20. It’s great to have such amazing talent at the agency now. I wish that I had done that sooner. But when you’re bootstrapping your own business, it’s kind of part of the deal, I think.

ROB: Congratulations on that growth. You mentioned a COVID baby, so I’m sort of expecting, by your story, that maybe you did get some maternity leave this time around?

ASHLEY: [laughs] I didn’t. Well, lesson learned from the second child, but we were in crisis – not crisis, but I didn’t think that it would be good for me to have no visibility to my team when we’re all suddenly working remotely and in the middle of a global pandemic. So, I made sure to still be around for internal purposes, but I did remove myself from some client-facing work for a period of time. I had my baby Memorial Day weekend, and by Labor Day my clients were seeing me on the regular again.

ROB: Got it. I can definitely see a case for visibility to a team in a time where everybody’s in uncharted territory.


ROB: Where are you and your team in terms of office? Did you have an office, do you have an office? Are you going to have an office? Are you keeping the same geographic footprint moving forward? How are you thinking about physical space in the context of Yakkety Yak?

ASHLEY: That’s such a great question and something that’s so relevant right now. We have this awesome office in a loft building right near the train station, Union Station in Chicago, and it’s great. I love the space. It’s got that brick and timber feel, lots of natural light, open area. But we jammed a lot of people into that space.

I’m currently working with a designer, Lauren Ashley Allan. She’s a really awesome up-and-coming designer. We’re revamping and rethinking our space so that it is comfortable for people when we return to work. Flexible seating options is what we’re focusing on, in addition to little booths so that people who are a little more conscious or want more privacy can work in a confined space that has ventilation.

The goal is that we’re not going to mandate that the team come back to work, but we are going to open our doors after Memorial Day, and I’ll be there and give people a place that they can come and work if they want to escape and gradually start getting people back together. I think what I’ve been noticing is I miss the vibration, like the good vibes that come from having a team all together. So, we’re putting some thought and intention into how we’re designing the space, and we’ll move forward from there with some flexible hours, combination of remote work and in-person.

ROB: Right, but you’re probably not going to have folks moving to Portugal and being fully remote, that you could think of?

ASHLEY: I don’t think so. [laughs]

ROB: [laughs] It sounds like you’re being very intentional about your space, which is compelling, and it sounds like even within the office environment, you’re really differentiating that work environment. Knowing Chicago, knowing where you are, you have a benefit of accessibility and transit and that urban lifestyle for those who choose it. And obviously, in Chicago, you can get into the city from very, very far out on a train if you want. And then not knowing the specific block you’re on or whatever, during normal times, there’s probably a good vibe, good places to grab lunch together, grab Happy Hour together. It’s not just some nameless office park.

ASHLEY: Right, exactly. That camaraderie is just important. I really felt for people – especially those who are in there, mid to late twenties, single, living by themselves, and stuck at home during COVID. That’s a lot for people. I think that we’ve got a lot of healing to do as a country when it comes to finally starting to emerge back into everyday life.

I want to be there and I want to create a safe space for my team to come in and get work done and feel welcome and safe and so we can continue doing the excellent work that we’ve been doing and build off of that energy.

ROB: That sounds excellent. How’s your team thinking about that? I know everybody’s all over the spectrum, at least from people I know. Some people would be in a closet together tomorrow and some people are waiting until they get a shot or even longer. What’s the range of what you’re seeing?

ASHLEY: A range, you’re exactly right. I’m giving people space to make the decisions on their own for now. We continue to check in on it. I’ve said that in 2021, at this point, we’re probably not going to do a mandate to go back to work. But we will open the doors and encourage people to come in if they want to.

The beauty of the transition that’s taken place from a remote workforce standpoint is that now we see that we can work remotely, that if you’ve got to coach your kid’s softball team in the afternoon, you can work from home, and that’s going to be fine. We’re going to be able to connect, and no one’s going to miss anything. I think this has done wonders for the work-life balance, and I hope at least at Yakkety Yak, that’s a trend we’re going to really continue to let permeate our office culture.

ROB: I love the intentionality of it. I’m a little bit jealous. I’m a little bit more of a “ready, fire, aim” sort of person. Over the course of the past year, the last four people we’ve hired have all been remote, and we’re going to figure it out later. I’m hoping that late fall/early winter, we’ll get together and visit one of our team who lives down in Chile. It’s completely different. Walking away from the office and loading the furniture into our basement kind of made it real, you know?

ASHLEY: How did that feel for you?

ROB: I am very comfortable with the change. The thing I don’t like in my basement is there’s no people there. There’s fresh air and light. It’s a little rustic, shall we say. I do miss the getting together, but if part of it means that instead of being in the office and doing little things, we get to do something more pronounced like spending a week in Chile and getting some different gatherings, I’m interested in it. It’s a change of pace for sure.

Ashley, when you think about the future of Yakkety Yak, the future of marketing and how you’re working with businesses that give back, what are you excited about in the future that’s coming up?

ASHLEY: I couldn’t be more excited about video. We are doing some really, really, really incredible work when it comes to especially the patient space, telling people’s stories about how they’ve been impacted by various health conditions, diseases, disorders. I love using video as a mechanism for storytelling, regardless of the target audience. There are so many cool things now with TikTok and how to use visual elements to show a progression, and people are doing that every day in their homes as amateurs, and how that’s going to translate to professional level videos I think is something that is so cool and something you’re going to see exploding in marketing space over the next 18 months.

ROB: One thing I wonder about, if you have an opinion on it, is when I think about audio and the way it’s going, I see a lot more attention going into the sound on versus sound off experience and accommodating people who might be muted. What direction do you see that going? Are we going towards where every video’s going to adapt, or are we going to where we’re assuming that so many people have some sort of Bluetooth headset in that they’re going to have audio on? How is that trending?

ASHLEY: That’s a really great question. I’m going to answer it in two parts. One, I think that the pandemic has shown everyone the importance of quality A/V, like when you can’t hear someone on Zoom or there’s a delay in a recording when you’re watching things virtually. I think that high quality video and audio is something that’s more of a priority than it’s ever been.

With that said, I think it depends on the platform. We wouldn’t necessarily, for a virtual fundraiser or virtual event, have all of the text scrolling at the bottom of the experience, but when it comes to ads and what’s happening when people are scrolling through Instagram, I think it’s absolutely vital to have the words there because people are scrolling through Instagram in their beds at night when they’re not necessarily wearing headphones and they don’t want to wake up their partner, or they have babies that they’re feeding and don’t want to scare the babies. That’s my personal experience, but I think it applies across a multitude of scenarios.

And people are multitasking, too. They might have one window open or be on a conference call or a Zoom call and scrolling through Instagram. You can’t have that dependence on the audio in those scenarios. 

So, when it comes to social media, the text is vital. When it comes to other experiences where you’re holding people’s attention for a little bit longer, then I think you’re okay without it. 

ROB: Very, very interesting. Thank you for illuminating the topic. Ashley, when people want to find and connect with you and with Yakkety Yak, where should they go to find you?

ASHLEY: Our website is the best spot to find us because you’ve got links there to all of our social media channels. You can find us at The spelling isn’t necessarily intuitive.

ROB: How did you choose the spelling of Yakkety Yak?

ASHLEY: [laughs] I don’t know. I think it was probably the domain that was available at the time. But it was important that we were Y-A-K and not Y-A-C-K, so we went from there.

ROB: Perfect. Ashley, thank you so much for joining the podcast and sharing your experience. I definitely wish you the best as you get that revamped office up and humming and get everybody back working together in person.

ASHLEY: Thanks, Rob. I really appreciate your time today. This was fun.

ROB: Thank you so much, Ashley. Bye.

Thank you for listening. The Marketing Agency Leadership Podcast is presented by Converge. Converge helps digital marketing agencies and brands automate their reporting so they can be more profitable, accurate, and responsive. To learn more about how Converge can automate your marketing reporting, email, or visit us on the web at