How to Craft a Winning Content Strategy: Ross Crooks from Column Five

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Welcome back to Agency Journey. This week, I've got the pleasure of bringing on Ross crooks from column five. Column five, media.com Ross, thanks for making time and joining me today.

Yeah, thanks for having me. I appreciate it.

So we got a chance to meet earlier this year. You guys have. You got a really cool story, and I want to dig into a couple of similarities in your journey and some of what we've been through. But first, could you give us maybe the 32nd minute long, kind of the overview of column five and your own. Your role at column five?

Yeah, yeah, sure. So column five is a creative agency. We do a lot of marketing work for brands, and in more recent years, that means kind of working with them from anywhere in the brand strategy, content strategy, and then into sort of content production. So we've done a lot of creative content production in a variety of forms over the years, and our client base looks like a lot of tech brands, but we a pretty diverse array of clients in education and the nonprofit space as well. So it's spread around quite a bit. And then my role with the company, I'm a co founder. I have two partners that I started calling five with about 12 years ago, and I oversee our creative teams and our kind of operations teams.

Were there three co founders when you started as well?

That's kind of a trick question. There were five originally, but we actually sort of separated from the other two pretty early on. So it's been three for most of the ride. I.

We started Andrew, my current business partner, who, you know, he and I, along with two other good friends, out of our college dorm room back in 2011, started our first agency and I went and met with a friend, totally different. He's a big pole barn builder, so totally different industry. And had lunch with him like, my senior year, and he said, so you're starting a business? He's like, yeah, how many founders? And he said. I said, four. He. He's like, a year from now when we're talking, there's not gonna be four of you. I was like, it's kind of a rude thing to say. Why'd you say? He's like, no, it never works out. Don't take it personally when it happens. Like, you guys probably won't be in business together for the whole time. A couple years later, it was the two of us. Yeah, still great relationships. I mean, it's just hard to get. You know, a business is a. Is a big undertaking and not everyone's a fit and you don't know all that stuff going in. So it's kind of.

Yeah, it's really. It's really has to be kind of a perfect balance of equal contribution and skill sets that work well together and personalities that work well together. It's interesting how that plays out.

It is.

We still like to give each other a hard time about ownership, jokes and who's going to be out next.

That's classic. So as I was doing some digging through some of your background, this theme of data design or data visualization came up. You are an author. We didn't mention that at all. But you've written a book on infographics. You started a software that looks like it was around infographics. Was that. Where did that focus? Maybe tell us a little bit, I guess set the stage on what that background looks like. But where did that come from?

Yeah, yeah, good question. And it's a bit of a long story and a little bit of an accident, but what happened essentially was the. My co founders and I were all kind of working in different businesses. We were all working in the clothing industry. I had started a clothing, like a men's clothing brand with one of my partners and our other partner was doing the clothing. He had a boutique. And so we were all kind of working together in the space trying to make our first companies work. And we started a blog that was sort of like an artist, music, fashion, lifestyle type blog to be able to cross promote our own brands, but also like bring, you know, partners in and build relationships and that sort of thing. To be able to create something of value basically through like sharing and giving media. And as we got into that and started creating content for this thing, we started getting pretty good at like creating and promoting content and getting it. Getting popular, having it go viral and that sort of thing. This is like 2007, 2008. And what happened is a lot of brands started to see us have success in that. And some of the early startups that were getting into kind of content marketing and trying to go. Trying to stretch their marketing dollars a little bit further. And so they started hitting us up to create and promote content for their blogs. So mint.com was a really early one that was, that was a client of ours that was kind of a startup at the time. And we started, we started creating content for them. And how the. The data visualization and infographics focus came was really what was happening is we were creating and promoting content in a lot of the social news sites at the time, which was like the Reddit.dig.com. yeah, like StumbleUpon and what we were seeing was a lot of people really geeking out on old infographics, like scanning them out of encyclopedias, looking at them at old newspaper clippings. But no one was really creating new contemporary infographics outside of a few news outlets like the New York Times at a very high level. So as we were writing articles for these startups, we started to kind of piece together, hey, we can use this data from these startups and visualize it and use contemporary graphic design to make a more visual artifact. And that was kind of how we made a name for ourselves was in pioneering those common. Now it's a mainstay in the marketing ecosystem. But this long skinny blog infographics kind of developed organically like that.

That's wild. Remember Noah Kagan? Was it mint back in the day.

Right before our time there? Yeah. Okay.

And then.

I think so, yeah. But yeah, I know from, from someone that's.

That's kind of a wild journey. So is that, at what point then does the agency become like, was that, did you just get enough traction on that side? That that was the evolution of hey, we want to start, we might as well do this for other people now as an agency or what's the start really?

Yeah, I mean we were just trying to figure out a way to work together and to do something that was fun and creative and make some money. And yeah, that started to get traction and so we sort of slow, over the next year or so kind of shuttered our other businesses and developed something together and it started growing really quickly. So we kind of put all our eggs in that basket.

And then. So you wound up building out a software. My impression is it's a infographic. It was an infographic generator, right?

Yeah, somewhat. Yeah. Kind of a web based design tool.

That was yam meant for like canva for infographics? Basically.

Basically, yeah. Yeah, I think, yeah, there were a lot of similarities there.

Okay, makes sense. And then is that still active?

There are a few clients that we're still kind of working actively with, but we're not actively like marketing it or selling it.

Yep, makes sense. How was that? I assume at that point the agency already had legs. Was that the. I mean, I feel like every agency goes through it at some point in time. The like, we're going to build the software on the side. We've got these extra development hours and resources that we can put into it and build it out. And some of them take. And some of them don't take as much. There's a range but was the agency the main thing the whole. The whole time? And software was side business or what's your.

Yeah, yeah, it was. So we started the agency in. In 2009 and kind of properly started it and then we started incubating the Software maybe in 2012 or 13, and then spun it out into a separate company in 13 or 14 and raised some venture capital receipt round for it and kind of made it split off the company and made a separate go of it with a separate team. And we did that for three or four years and we had a lot of good traction, but didn't get quite the traction that we needed to have it survive on its own. And so we ultimately kind of folded it back into the agency and kind of kept focusing on that.

I can 100% relate. I mean, we. A project management tool starting in 2013 in house, spun it out as its own business, took all our best people from the agency and moved them over to the software. And ultimately we weren't that good at software and consulting and had a. Had a choice to make between one or the other and went down the road that we were better at the less lucrative path from evaluation perspective.

It's hard work. It's a competitive, competitive area. Especially when you're something in something like project management or market is like just an insanely busy ecosystem.

But that's awesome. And then. So for a little while you were also teaching at Columbia, right? And you were writing and you're building an agency and you had a fashion like, what's the. Let me, I'll back up, I'll start with a book.

Here.

Was the book. What was the journey to say, hey, I need to write a book. And then was it worth the effort that it took?

Yeah, good question. Yeah, you make it sound like everything happened at once. And it kind of did. It was like I think 2012ish. But yeah, we had the opportunity to write. Wiley approached us, book publisher, to write a book on infographics. And we were kind of the leaders in that space and had done a lot of the thinking around it and developed more practices and things like that. Other people were creating infographics, graphics for sure. But I think we were the first people to start to do it at scale and really commercialize it. And so we, I mean, that was like an exciting opportunity for all of us to be able to put our name on something and share what we knew. And, you know, also a good kind of marketing tool to have to say that we wrote a book on the topic and yeah, I think it was the exact same week that Columbia University approached us to write or to do a course on visualization of information. So we couldn't really say no to either. And so we were developing the course and writing the book at the same time. And I was on my honeymoon for some of it and moving into a new office and building it out and that sort of thing. So it was kind of, it was a very, kind of crazy time. But I think looking back, I mean, certainly I think it was worth the time and effort to be able to write the book and the experience of teaching as well. I kind of wish I had more time to dedicate to it. And obviously thinking and philosophy and all those things has evolved quite a bit over the years from those early days. So I think, you know, I'd love to, to be able to update it sometime or, or to, you know, do a follow up.

Right. Well, I wanted to bring it up because you're saying like, oh yeah, Wiley approached us and Columbia approached us. And then if you go to column5media.com for anybody who's looking at the site, you can see a bunch of logo. You know, you guys have worked with like LinkedIn and Uber and Netflix and Dropbox and you've got all these big household names in the tech space where. So. But those connections obviously don't come to most four year old agencies or kind of early stage agencies. Is this largely a product of networking or. I mean, I'm sure it's always a combination of. You guys were super early on a trend that stuck as well. And so you got a chance to be first movers and benefit from that advantage. But you're saying things that most agency owners don't get to live through early on in their career, which is why I wanted to have you on, because it's a fascinating story. Where did those connections come from?

Yeah, I think a lot of it did come from being kind of a first mover in that space. So we were able to be found when people were looking for execution on that. I think the other, the other piece was we were working with a lot of these kind of scrappy early stage startups. So as these people got acquired, we kind of came into their mother companies. Right. So Intuit acquired Mint, so we worked with TurboTax and we worked with QuickBooks and these sorts of things. We worked with LinkedIn and Microsoft and they came together and GitHub and things like that. So I think some of that just happened naturally through this sort of M and A cycle. We had A lot of really good clients early on that we were, you know, friends with and that were really helpful to us and just making introductions and those people went places. And so I think a lot of that is just sort of the organic things that happen when people move from company to company and clients acquire each other. But I think the nature of our work has always been pretty visible because, you know, early on it was like, you know, the goal was always to go viral. So we had a lot of that and we had attribution on a lot of our graphics. So it's Created by Column 5. And so a lot of people would find us through those sorts of things. And now that that's shifted away from the novelty of the format and it's shifted away from being able to get credit on everything we do, it's much more about our own content marketing strategy. So creating useful resources on our blog and kind of pulling people in through that.

The blog, outside of being beautifully designed, you guys produce a ton of content on all these different topics. Definitely recommend looking at the blog if you're listening for inspiration as well as the resources themselves. So that piece hasn't. Even though infographics have, you know, they zoomed up in terms of a trend and then maybe have cooled off a little bit, the dedication of content hasn't changed at all, which is cool to see from the story. So one of the things that a lot of early stage agencies struggle with, agencies in general struggle with, is like, who's my market? What are we doing for them? What's the fit between what we're good at and what the market needs and how do we get in front of on those people? Was the tech ecosystem, was that an intentional decision or was that kind of an accident of, hey, they're early adopters and you guys were early adopters?

I think it was more just the coincidence of that. And even over time we've asked ourselves that question of do we need to narrow our focus? Because we work with a lot of different companies, maybe 100 plus companies in any given year, and those are all across different industries and verticals. So I think there tends to be a tech focus just because those are people that have pretty well established digital marketing practices. And so it tends to be a good fit. But yeah, we've never been exclusive in that way.

Right, that makes sense. How is users have scaled out and are servicing the volume of clients that you are. What does that look like, scaling client services to support that kind of growth?

Yeah, it's always a work in progress. I think we're even looking at. We've been experimenting a lot, even this year, just with reorganizing our teams and working in different ways that might better serve our clients. I think that there's. What I noticed there, I guess, is that there's always this balance between the flexibility of staffing anyone on anything at any time, with the focus of having a dedicated team that works really well together and has clear established ways of working and that sort of thing. So there's pluses and minuses to both those things. And I think we're trying to figure out what's the balance of the most pros.

Right.

As many cons.

As you looking forward to. Because I was just mentioning this is a great time to. To grow. Like, we're coming up on the fourth consecutive quarter of the best growth, like across the board for agencies that I've seen in the last 10 years being in the space. But staffing for that is. Is a challenge at the same time. So I'd imagine that's. That's part of where you're spending some of your time now, but kind of inclusive of that and other priorities, kind of as you're looking forward to. What is the end of 2021 look like? What does 2022 look like for the agency? What are some of the big targets that you guys have as a firm?

Yeah, I think recruiting has definitely been a big one for most of this year. I think coming out of last year, that was pretty uncertain. We were sort of hunkered down and just making do with what we had and. And figuring it out. And then the beginning of the year hit and felt like we needed to grow by 25% overnight. And so that's been a longer than usual cycle to get new people in the door. But we've just had maybe five or six new people start in the last month or so, which is really exciting to have some new faces and to be growing again. Yeah, it's been. I think what that looks like is we're really trying to. I think we've been behind in some of the things that we've been doing just because we haven't had the staff to be able to be really proactive in some of those ways. So I think it's getting more intentional and more proactive with each of our clients to be able to look forward into what needs are not being met, what opportunities are there to grow with those people now that we sort of have the capacity to do it. And one of our big focuses and sort of one of Our this might be going back to your other question sort of about the evolution as well, is one of the more intentional shifts that we've made in the last couple of years was to start to move upstream from just a lot of like creative content production into the strategy realm. And so we've really built out that practice and those roles on our team to be able to, to build the foundation that's needed to create content. And any marketing down the road, any sort of communication is understanding, you know, at the core of the brand, what is their, what's their sort of purpose and values and then flowing that into a strong content strategy and then being able to actually create content for them. So that's, you know, some of the roles that we're hiring for. Right now we're hiring a couple strategist roles. We're hiring for a new account director or maybe two and a new video producer as well. So.

What is that when you say staffing up and kind of going upstream and you mentioned strategist role. So I'm assuming that that's maybe strategy roles. What's the correlation or how as you guys are scaling up, how is that set up from an org chart perspective, I guess, do you have. Because typically you'll see like an account manager or strategist, this kind of lead of X many accounts and they either working in pods or shared resources underneath them. But you mentioned account directors. So is a strategist working across more accounts, fewer accounts? What's an account director's role? How do you kind of break down those distinctions?

Yeah, our account directors are kind of responsible for growth in the relationship. So they're, they're maintaining the relationship and doing some planning and budgeting and things like that. But they're also really responsible for finding new opportunities and understanding what the client, what else client might need. Our strategists are really focused on actually just building out the strategy in any given engagement. So understanding where a brand is at the time, what gaps might need to be sealed in their, in their strategy and being able to do the research and make recommendations on that that then we can go and kind of execute.

On downstream and who coordinates that execution.

Usually a producer role on our team. So that's sort of our, our creative project manager. It looks a little bit different on different work types.

Right.

Some people are very tactical project manager and some are, you know, getting much more into creative and helping to guide the team in that. But yeah, they kind of help run the show.

That's awesome. Russ. I'll look this up Real quickly, the careers page. I'm trying to remember, but I think there's just. There's a link from the footer that takes you to the careers page on the site.

Yeah, just column5.com jobs.

Cool. Okay. That's even easier. Awesome. So, yeah, if anyone's interested in opportunities with column five, actually just saw one person who just. You just hired is from Erie, Pennsylvania.

Yeah.

So that's where I grew up.

I think we just hired two. Two Pennsylvania people. Okay. Yeah. Angelique and Keisha.

We're infiltrating. Infiltrating column five. Slowly, slowly happening. That's awesome. Awesome. Well, this has been really fun to dig into the column five story. I think as you look at kind of closing out this year. One question I've just started asking people, I did not prepare you for this at all, but is around. This is just kind of a fun question. Is around kind of year end expenses or like write offs? We run into a lot of agencies. This has come up a handful of times here recently in Conversations. Folks, I have made more money than I've ever made this year. What are we writing off? Do you have any fun end of year write offs that you're planning on for this year or past stories?

I don't think so. Usually it's a balance because we have clients that are trying to get rid of their budgets, but sometimes we're playing the bank in that and we're like, we might take it on the nose for on from on the cash or the tax bill, but we'll take your money and work through it next year.

Right.

But yeah, sometimes we're trying to, you know, we're also trying to wait to wait to cash the checks until the first of the year for sure. Yeah, nothing big. We started doing a little more just in terms of. We just like got everyone their own credit card. So we're having a lot more. Trying to put a lot more toward kind of connection and communication events. So a lot of times we'll have, you know, we'll all order lunch from our own respective places while we do our town hall meeting or we'll have, you know, different celebratory type events where everyone can just kind of spend their own meal budget or that sort of thing.

So that's cool. I'm obviously a tool nerd. Are you guys using. Is that. Do you run your credit card through Brex or through Ramp or are you using something else?

We're using Divi.

Divi.

Okay. Yeah, we just switched over to them earlier this year.

Makes sense. That's awesome. Yeah, I think all three of the. It's been cool to see just the business credit card space change in the last couple of years. It was like Brex kind of burst onto the scene and then all of a sudden Divi was the next big one, and then Ramp is just raising absurd amount of money right now. So it's been interesting to watch that space evolve.

Yeah, it definitely seems like a good evolution because I think it's been messy for a while or a hard thing to do.

That's awesome. Ross, for folks who want to connect with you or follow you online, outside of the Column 5 site, is there anywhere else we should point people?

I don't think so. I'm not active really on social media, which is strange for a person in.

My position, but try to preserve podcast episode about that.

Yeah, yeah, I have. I have a couple accounts, but don't use much. But yeah, everything's really through. Column five is kind of my. My focus. Awesome.

Cool. We'll make sure all that stuff's in the show notes. But I appreciate you coming on, being generous with your time. This is a fun conversation. Thanks, Ross.

Thanks, Greg. Appreciate.