Listen in today's episode as entrepreneur extraordinaire Mark Walker shares Direct Digital Holdings journey.

Mark reveals how laser-focusing on people, processes and credibility grew revenues from $6M to $120M in just five years. His insights on genuine networking and understanding capital raising are invaluable.

We also explore leveraging AI for personalized ads and how concentrating on small wins propels growth. Mark's servant leadership style emphasizes collaboration in decision-making.

Transitioning from private to public, Mark outlines assembling experienced boards through professional connections. Continuous learning, reading and informed networking develop strong leadership. This glimpse into Mark's exemplary journey offers a treasure trove of strategies for success.

Show Notes

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Mark: Yeah, thank you for having us.

Chris: So let's just get started by you telling us, tell us, direct Digital Holdings. What is that company? What are you known for?

Mark: Yeah, very simply, direct Digital Holdings. What we do is we help companies buy and sell media and we leverage technology to do it. We have a buy side platform where we actually work with roughly about 250 different clients all across the United States, focused on the middle market, and when we look at the middle market, there are companies that are five to 500 million in revenue and we help them purchase media in order to drive our way of performance for their company. The second half of our business is Colossus SP, which is a supply side platform, and that side of the business we help publishers such as USA Today, gannett, hearst, brands of that Nature actually sell media in an automatic or programmatic way throughout the digital ecosystem, and so we work with about 26,000 publications, helping them sell media online and that's everything from digital banner ads to CTV, ot, streaming audio ads and help them generate revenue for their publications and for their websites.

Chris: That's great. So what was your inspiration to start this company and grow it to where it is today?

Mark: Yeah, absolutely. My business partner and I. We actually worked on another publisher, ebony Media, and while we were at Ebony we saw how the value chain of the programmatic ecosystem and media buying was changing.

We saw that publishers were having difficulty specifically multicultural publishers were having difficulty getting connected into the programmatic ecosystem because their websites were too small and typically the larger players in the marketplace would want to work with publications that had 10 million unique visitors Well, anyone less than that. They didn't think it was worth their time giving them the technical expertise, know how, wherewithal, to connect into the programmatic ecosystem and purchase media automatically. So we saw the opportunity to buy two nascent platforms. One was Huddle Masses, which was the initial buy side platform. The other one was Colossus, which was the sell side platform. We put them together underneath one brand direct digital holdings and we started off with roughly about $6 million in revenue, and this year we're projected to grow to about 120 million in top line revenue over the course of these five years, and we've been really blessed and honored that many clients and partners have decided to work with us over this time.

Chris: Yeah, I get a meant remarkable growth. Let's talk about a little bit. So this is your first stint at being an entrepreneur.

Mark: Yeah, absolutely. Yeah it's myself and my business partner, Keith Smith. It's our first time really stepping into the role of operator. Previously I worked at startups. That's really where I first got my digital expertise and worked at Deloitte, worked at NRG Energy here in town and then also at Ebony Media. So all the while I've been working in the digital space, but this is my first entree into entrepreneurial space, really around the digital platform.

Chris: So what were some of the lessons that you've learned, starting basically your own company and taking on that leadership role where everything you know, the buck stops with you? Maybe explain to our listeners, maybe, some of the things that that you've learned along that journey.

Mark: Yeah, you know, I would kind of frame it up into three different categories.

Chris: One one.

Mark: It was about building up credibility in the marketplace. Having a good name, having a good reputation, having a network that you could lean on, I can tell you has been categorically valuable. That network is what I've leaned on for board members, what I've leaned on for contacts, relationships all throughout my career and really it's been 20 years of building up relationships that has come to fruition through this organization.

Chris: That's number one.

Mark: The second was really building up the credibility as well as the connections, but really the credibility of learning a craft and an expertise. That's been the second thing. And staying inside of the digital space and having 20 years of experience, it just kind of gives you secondhand knowledge of how things are gonna operate and how digital operates and flows.

And then the third piece is understanding how to raise capital and put capital into the ecosystem. My business partner he came from private equity, worked on Wall Street and so he had the expertise and really brought that to bear, and so really it's been the culmination of those three things that we made a good partnership in bringing all three of those together. That's actually allowed us to have the success that we've had today.

Chris: Yeah, it makes sense. I mean you can't, I think, overemphasize the importance of building really good relationships throughout your career, because you never know what you're gonna need to lean on them.

Mark: No, that's exactly right. Yeah, my buddy, he gave me a saying a long time ago. He said network before you need something, and so I kind of lived by that ethos and I thought it was actually a good way of thinking about relationships. And usually if you do something good or nice for someone, even though you don't know how it's gonna come back to you, nine times out of 10, it always comes back when you need it, and that's really has been the story of our career and also our experience working with direct digital holdings.

Chris: Yeah, I like that Network before you need something which said in other ways be genuine, right, build relationships in a genuine way, and then, yeah, it's always nice to help people out, and then if you do that from a point of genuineness, then it gets returned. It always gets returned somehow. So let's talk a little about your growth. I mean 6 million to 120. What are some of the things you feel like you and your co-founding partner have done to help kind of manage that growth, Because sometimes rapid growth can destroy a company. Anything that you can kind of share with us, that you think you all have kind of put into place to kind of manage this growth so that it's a healthy growth and that the company is sustainable.

Mark: Yeah, absolutely, you know. It was really, you know, going from 6 million to roughly we did. God took about 30 million through an acquisition and so that was a good push for us and then, from that 30 million, really the next trunch from 30 to 90, which is what we did last year we really started working on processes. I can't stress enough in my experience back at Deloitte as well as with NRG really emphasize the importance of process people. You can't grow without people and you can't grow in an organized fashion without processes.

And so we internally have been focused for the last two years really building up the processes and bringing new people into the organization to work specific tasks you think about when we look at organizations inside of us, inside of our organization. Part of the training had incorporated is you look at the functional first. Remove all the bodies, just think about the functions that need to be executed, think about the KPIs and the accountability, and then you start assigning the right person for the right role within those functions and understanding that each leader can only manage roughly four or five people effectively.

So, we've definitely have had an emphasis and a focus on people, processes and accountability in KPIs inside of our organization. And that's really has led us really to take it from 30 to 90 million. And then we're putting more processes in, more what we call our third and fourth layer of employees inside the organization for us to really take that growth from the 90 to the 120, hopefully from 120 and beyond.

Chris: That's great. So totally agree process and people, especially people, are the most important right. You can't no chance of achieving that kind of growth without good people. So what are you doing? And I don't know, how's your employee head count grown when you were at the six and even maybe the 30 to now? How many people are we talking about?

Mark: Yeah, so back when we were at six we had probably eight, nine people total. Today we're at 85. So definitely like 12x growth from where we started off. The good thing is we've hired a significant amount of people with experience, a wealth of experience inside of the industry.

So that really cuts down on the learning curve. And then the next piece is giving people the distance and direction where we're trying to go, and give them the guide rails. We'll let them figure it out. The thing I try to say internally is if I had to tell you how to do your job, then one of us is not doing their job effectively. So my goal is to hire people who understand and aren't afraid to fail. Put them inside of a structure, give them the distance and the direction of the resources that they need to try to accomplish a task and hopefully, get out the way and try to remove boulders when necessary.

That's been kind of our leadership philosophy inside the organization and we think we empower our employees to actually accomplish a task that we put in front of them and hopefully we can celebrate at the end of the year for them achieving it. Most of the times nine times out of ten they actually outperform. So we think if we set up the right structure, giving them the right resources to help, them and then giving them the proper distance and direction and get out of the way.

usually that's an effective way If you hire the right people, for them to be effective in their jobs.

Chris: I like that. So, going with the people theme, you got to get them in the right seat, give them direction. What are you doing there at Direct Digital to foster a culture and so that people want to stay? Let's talk a little bit about that.

Mark: Yeah, the culture that we really try to foster is one based on integrity. So if you're going to say something, follow up and do it. If you don't do it, take account of it before it. That's number one we try to foster that. We also foster service to each other, and that's the biggest one. My job as a leader is really to be of service to the employees, so take it serious to try to provide service to them and getting them what they need in order for them to execute effectively, and so we try to instill that inside of our leadership team and view it as it's not you doing what I say. It's about you enrolling in what we're trying to accomplish, and then let me help you get there. And so, even though we give big goals to our employees, we feel like it's all of our jobs to own that goal. And so I'm right there making phone calls. I still go on sale pitches.

Last night, I had a client dinner we're still out here boots on the ground and if I'm not the number one salesperson trying to help generate sales and leads for the team, then I feel like I'm not doing my job. So that's kind of how we think about it. And when we try to hire employees, the word we termed as we want strategic doers. I like that. Yeah, we don't. We, you know, we're very deliberate that, especially in the growth phase that we're in, I need a strategic doer, someone who can be strategic but someone who doesn't mind rolling up their sleeves and getting dirty and running a report or making a sales call or generating leads. We need everybody doing it and then if you do effective job, then hire more resources underneath it. You can start moving into the strategic role.

Yeah, Every employee starts off that way. We think it's a bit of an effective way for us to grow.

Chris: Kind of that mindset of do what it takes to get the job done. Yep, well, it sounds like you know a lot of collaboration to kind of a team, teamwork, team, teammate mentality. Yeah, but you talked about you know just your hiring process, anything that you guys were doing there. Do you think they're somewhat innovative in how you go about the hiring process to make sure you're getting the right people? And maybe any challenges you faced in the last few years, given the environment and the economy?

Mark: Yeah, when we come to the hiring, what we adopt as our philosophy is everybody touches them. So if the team is going to interview, if the person is going to be working on team, everybody on team has a say. Everybody on team has veto authority. And then the one thing I try to remind the leaders is the problem is going to be the problem. So if one person identifies a weakness, another person identifies a weakness, then that's probably the weakness in that person and it's not going to change. So then you have to ask yourself the tougher question Is that weakness detrimental in this role, or is that something that can be covered up or managed?

And so that philosophy has been very instrumental in us being effective and we've been very. When we have our debriefs after we interview someone, everyone comes together. One person feels like I don't think they're going to be a good fit or I don't feel comfortable working with them. Then that's a no across the board. So very rarely have we made a decision that the collective wasn't comfortable with that person coming into the organization. Maybe it's my old fraternal approach to things, pledging a fraternity, and my business partner he actually played football at UT, but feel like a team and a collaborative approach is always the best way to try to find the best candidates and make sure you can protect the culture of the organization.

Chris: Yeah, no, I couldn't agree more. I think that you've got that cohesiveness. You just can't put a price on it. And one person you hear it a lot in sports right, but a bad apple in the locker room or can destroy a good team, or quite the opposite. Maybe not a group of the best stars, but they get along. They can play above their natural ability.

Mark: Yeah, absolutely.

Chris: And.

Mark: I love that yeah.

Chris: So let's talk about a setback that maybe you've encountered in the last since starting at the company. Explain, maybe a setback you've encountered, what you did to overcome that, maybe what the learning was and how it's made you or the company better. Yeah, absolutely.

Mark: You know, in moving and growing this fast, sometimes you miss processes and you know the way that we view it. One person didn't miss a process. We all missed the process. So for us you know, we've done that before where you know you have might be a process set up to protect the organization and you missed it.

Sometimes you got to go in and everybody has to rally around and say, okay, guys, let's figure out what happened. There's no fault to be assigned, but really what it is. Let's figure out where did the process break down and we're all collectively accountable.

So, that's really the approach we've taken, what I think it actually helped us. It actually helped us Really identify are there any other holes that we have in the organization we need to plug up? You know, you know what you know, but you don't know what you don't need. You don't always know what you don't know Right, and so it's that piece that, unfortunately, usually errors get pointed out and that's the correction that you have to go in place. But we try to take an attitude of it's no one's fault, it's all of our problem, let's all own it, let's take accountability for it, let's fix it.

Chris: I'd have to believe that helps foster that it's okay to fail type of mentality you talked about earlier. Right, that if everyone's kind of you feel like everyone, that's your coworkers are in it with you, then you're more likely to take that risk, knowing that failure is not going to point fingers at you as a result.

Mark: Absolutely, and that usually usually helps, because if everyone's in there with you together, then you're okay. You know you got coverage.

Chris: Yeah.

Mark: So that's the best benefit that you have.

Chris: Switching subjects a little bit, let's just when you think about what you guys are doing and both sides of your business, anything kind of innovative that you all employed, that you think has really helped the trajectory of the company and this growth you've seen.

Mark: Yeah, I would say a couple things. One, we bifurcated our sales groups, so we have lead generation and then we have our sales closers. That has been instrumental. Let the hunters be the hunters, let the farmers be the farmers and let them both work collectively together. That has been instrumental to help us grow. Specifically on our buy side business, we've been growing solid 10-20% year over year. That's a tougher business to grow but the level of growth that we've been able to see has been very effective for us. Very proud of what we've been able to accomplish on that piece On the sell side of our business, which has been growing 100-200% year over year we've been able to really foster an environment where a lot of companies will go in and try to get the big whale.

We play a lot of small ball inside of the game, so a lot of fruit what I call was low hanging fruit had gotten left by our competitors. We called, we made calls, not to the highest level person, to the lowest level person, told them to test out our platform and, sure enough, we were able to grow that business that way. Our business leader was very innovative on that approach, calling what we call fingers on keyboards those are the decision makers, the day-to-day decision makers to get them to try out our platform and through those efforts we were able to grow effectively. So sometimes, especially when talking to other entrepreneurs, sometimes look for the slow hanging fruit. Don't try to hit the home run, try to hit the single.

The single will get you on base and that gets you actually in the game. That's kind of the strategy we've taken.

Chris: I think that's great advice for some of our listeners out there that maybe trying to grow their company they just started is. You know, you don't always have to hit the home run of the Grand Slam right, you can start small and let that momentum build. What about AI? How do you see AI playing into your business model and what changes do you think are going to be coming down your path where you may need to make some adjustments?

Mark: Yeah, no good question. When it comes to AI, I think what you're going to start saying is it's definitely been around for some time, or some level of machine learning has been around for some time. We think of it in two different counts. We think of behind the house and then in front of the house. Behind the house, that's the stuff that you really don't see, but that's really inside of the processes. That's stuff that we're taking advantage of right now. We're taking advantage of a lot of different algorithms. We're incorporating AI into different pieces of it. You won't be able to see it, touch it, feel it, but it's actually making our systems run much more, our technology run much more efficiently. On the back end, that, I think, has been around for a while and we're definitely in that space and moving more advantageously in that space. Behind the house. In front of the house is where I think all the excitement is actually coming with AI.

The fact that you can do words with image imagery, natural language, learning, things of that nature I think we're going to start seeing in the next two years is a personalization of ads. Right now, you do a lot of ads. You might come up with 16, 17, 20 different recipes, trying to hit different segments. I think you're going to see a lot more personalization. On the data side, we have a significant amount of personalization of understanding what people like, what they dislike, their behavioral, demographic, psychographics all that information is already there. Now you're going to start seeing the creative reflect that, because creating new recipes of ads is going to be a lot easier leveraging AI technology than when you don't have AI technology. You have a human who has to replicate 20 different ads of the same idea.

I think that's really the next evolution that you're going to see. I think that's going to be the exciting part coming to our space in probably the next two years.

Chris: Wow, that'll be before you know it.

Mark: Yeah, it'll probably be here sooner than later.

Chris: Yeah, let's talk a little bit about leadership. How would you describe your leadership style?

Mark: I think it's more of a. As I said before, I try to serve all of my team members. On the personal, we all think of more of it as a collaborative approach. We think of each other as a work family. We try to foster that type of environment of a work family. If you go to our office space, there are offices, but the main area, about 3,000 square feet, looks like a house. It looks like a kitchen, has a TV, has couches. We try to foster a work family environment. We want kids up there. We ask employees bring your kids. We have X-pots for them to play. It needs to be a collaborative approach because we spend probably more time at work than we do at home.

Chris: Yeah, no question, right, so you might as well enjoy it while you're there.

Mark: The other way that I would say is my leadership style is I try to really believe in trying to be a servant leader, so every problem is my problem. If my team has a problem, it's my problem. I try to own it. I try to help people solve through it and work with them and try to hold them accountable for the result. But no one's held accountable on their own. We're all accountable, so everyone pitches in to try to help out. So that's what we try to do with the environment, that we try to foster Type of leadership style that we have. My team probably would say I get into the weeds a little too much. Sometimes you can't help it right.

Chris: Yeah, but I enjoy getting started. I get that. I get that there's some value, as long as you can regulate it to your team, seeing you willing to get in and get dirty get your fingernails dirty from time to time, right, and they're like, okay, you are in this with us, yeah, let's talk about. So. You've got your co-founder, keith Smith. How do the two of you manage the leadership roles in the company to be aligned and kind of maybe not contradict one another or step on each other's toes?

Mark: Yeah, so the way we operate Function is we both bring two different experiences and we actually did bring two different personalities to the equation my business partner, keith. He's definitely more on the finance side. So when it comes to the finance, when it comes to the administrator, when it comes to the legal, he owns that, that's, he takes the leadership piece on that and I'm more than happy to step out of the way. All those pieces we got to do refies. We're going through the IPO process.

He definitely took the lead on how to get that whole structure and organizing. Yeah, that expertise and experience for that.

Chris: When it comes to the operational side.

Mark: that's the piece that I bring more of my leadership style to, and so we meet in the middle. So when those two come together we meet in the middle. So it's really kind of clear lines in how we are structured. When it comes to investors, he takes the lead on talking to investors and stuff like that. If they need to hear from the operator, then I step in and have those kind of conversations.

Chris: But that's pretty much how we structure the organization and it works well that way, so clearly delineated roles and responsibilities, and then everyone in the organization understands that as well, how it shapes up.

Mark: Yeah, and then personality wise we make a good match, because I'm probably more of the passionate one, he's probably more of the sub dude one, so we meet in the middle that way.

Chris: Okay, yeah, that sounds like a great team. The results speak for itself. What about mentors? Any mentors you've had along the way? That kind of help get you to where you are, shape your leadership philosophies, your work ethic, etc.

Mark: Oh, absolutely, I had a thousand. You know a lot of them Some of them have been independent entrepreneurs. I call them my own personal board of directors. Reach out to a lot of them one-on-one to have conversations with them and get feedback and thought. Some of my mentors and leaders actually have joined the board, okay, and they're on our board of directors, and so definitely get a lot of leadership and good guidance from our board of directors, very happy with what they provide and the expertise that they deliver.

And then they definitely help shape the organization and also give me and challenge me to think through different either opportunities or also different risks that are out there. So definitely got the board, got my independent individual board of directors as well. Of friends that I actually call on that I've known for 20 plus years. Some are in the industry, some are outside the industry, but they haven't been shaped by all of them.

Chris: Let's talk a little bit about that. You know the board and board composition, etc. When did you and Keith decide to form a board of directors? Was it right out of the start or was it as the company was evolving and growing?

Mark: Yeah, so we started our when we were from 2018 to 2022, we were actually privately held, so we're probably I'll do as myself, keith and we had a third business partner who we ended up buying out, so we made up the constitute the board and, trust me, it was 100 times easier as a private company yeah. Because you look at Keith and I look at him and say what do you want to do?

Chris: Yeah, Right, which is typically how the small, privately held entrepreneur starts out. Right Exactly.

Mark: Yeah, and just kind of kind of keeping moving. When we ended up deciding to go public, we had to actually form a public board, and so then we had to start recruiting people with actually board experience and expertise and you know some level of ground toss and all that.

And that's when you know, we had to start tapping into our own connections, our own network. Our lead director we worked at Deloitte. We both worked at Deloitte, didn't know each other at that time but we knew mutual people and mutual friends and so we recruited her to come on the board as our lead director. She's been absolutely phenomenal. But really thought through, what did we need to help us grow to the next level? So we knew we needed technologists. We knew we needed someone with finance background and a strong experience and accounting around audit committee. Then we knew we needed someone with industry expertise, specifically from the agency side. So we're very strategic about who we brought on the board, why we brought them on the board and what value we were really looking to get in expertise.

So you know, my advice on performing a board is really to think through. Don't think about where you are today, but really think about where you're trying to go tomorrow and try to bring the people who have that experience and expertise to come on the board. Now I will say for us to recruit one of those members, best place to go is your law firm and your accounting firm. They know good people. They know people they probably worked with on other boards. My first piece of advice go to your attorneys and go to your accountants and see if they know of anyone who might be a good board member. That's how we started our recommendation process, yeah.

Chris: And I think you're right in picking those disciplines that you have again as a mentor or resource to bounce ideas off of, get direction from. Yeah, and you don't have to be a public company, a privately held company trying to grow can that entrepreneur can benefit from those resources.

Mark: Absolutely Firmly believe that and then build the right culture even inside the board. You want to collaborate on board who can think through problems collectively and come to a solution.

Chris: Yeah, what about? You know we all, we all try to continue to learn and grow. What are some of the things you do to kind of keep yourself sharp, to keep learning, to be that servant leader? You know the type of person that you want to emulate in the company.

Mark: Yeah, a couple things. One definitely mentorship. So you know, one of the pieces of advice I give is get into a CEO group, because everybody has problems.

Chris: Right, then you can learn from other people's problems before they become yours.

Mark: Before they become yours. You're like, let me take note of that problem. That's number one. But I would also say you know I read a lot. Yeah, every morning I'm reading, every afternoon I'm reading, I subscribe to God knows how many publications. So you really try to absorb information and I have to say you have to get out of the ivory tower and get out on the street.

Yeah, I'm a firm believer in, you know, hearing kind of the qualitative information. To me, if it's in the news, it's already too late. It's really the qualitative information that you get from networks that really kind of give you insight on where the trends are going. So I always try to keep my ear to the street. By getting out and meeting with people and taking people to watch, I get a lot of good information that way.

Chris: These are great pieces of advice as far as how to kind of stay in tune with things, and I think you're right. These days there's some great publications, you know I think Bloomberg does since two meals a day, one in the morning, one in the evening, and all that where news is coming at you fast.

Mark: It's coming at you and you gotta be on it every day, For sure You're absolutely right.

Chris: Before we change subjects, one or two things that you would say to some of our listeners that are trying to start, or maybe just start, a new company about here. If you're about to embark on this journey to pursue a passion on your own or with a couple partners, here are one or two things that I think you should absolutely do or consider doing, as you kind of embark on that wisdom there.

Mark: You know, the one piece of advice I would give is be all in Like entrepreneurship. I will just say two things. One, it's not for the faint of heart, but you gotta be all in. And so I think there is something about failure and success. The risk of failure will drive you to success. But if you kinda have one foot in and I'm still doing my job, but I wanna do this then you're not wanting to be an entrepreneur.

You either gotta be all in, ready to risk it all, or you don't. That's probably the one piece of advice I would give Pretty much everyone. And if you're not in the position to get yourself in the position to and then go all in, Don't think you can do it half in, half out. It won't work.

Chris: That's great, great advice actually, and very true. It's funny that's a pretty consistent theme of the guest I've had. Is that all in mentality? And the second is it's not for the faint of heart.

Mark: Right.

Chris: So just know there's gonna be tough times and you just gotta muscle through it. So let's go a little bit on the personal side. What was your first job?

Mark: First job in high school was a sacker at Randalls. I used to sack groceries when I turned 16, over off of Jones Road and, yeah, you made good money. If I came home with $40 after a cycle, I was pretty happy.

Chris: Yeah, and in the hot Texas heat. Oh absolutely, yeah, okay, so your native Texan. I always ask all my guests you prefer Tex-Mex or barbecue?

Mark: Barbecue hands down Gavils barbecue.

Chris: Oh, okay, there we go, no hesitation, and applaud for Gatlins. I love it. It's pretty good stuff. They've gotten a lot more competition now, but Gavils gonna win, yeah. So let me ask you this so if you could take a 30 day sabbatical not that you would, if you could where would you go? What would you do?

Mark: If I could take a 30 day sabbatical I would probably. You know, I really wouldn't mind going to Asheville, north Carolina, getting out in the mountains and enjoy some of that, especially in the fall I'd be out there all day Just out in the woods and hanging out.

Chris: It's a beautiful area. Oh God, it's gorgeous. Yeah, it's got a sketch right out there. Well, mark, I wanna thank you again for coming on. Congratulations to you and Keith on what you've built and are continuing to build. Love hearing your story and the insights you shared.

Mark: Yeah, absolutely, absolutely. Pleasure being here. I appreciate your time and thank you for having us.

Special Guest: Mark Walker.