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I was in college. The owner, the founder of pdg, was a professor of mine. I finally got the guts one day to walk into his office and said, if you want to sell, I'm interested in buying. And I really was focused that whole year on preparing myself for business. I was like, numbers, numbers, numbers. And about six months into this business, I realized it had absolutely nothing to do with numbers.
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Andrew Olson is a creative entrepreneur, branding
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strategist, and the CEO of PDG Creative. Drawing from decades of experience in branding, marketing, and business leadership, he helps organizations clarify their vision, strengthen their identity, and build meaningful connections that drive lasting impact. We're full service. We do everything cradle to grave. So we don't just kind of do a design or do a logo or do a brand or whatever. We come in and we really evaluate the landscape of what they're trying to accomplish and say, okay, in our sector of the pie, how can we make you the most successful? It spans the globe like a super highest cold intersect. The eldest president. Today, Apple is going to reinvent the phone. It's not over until I win. The Living your Legacy podcast. For those who live to leave a legacy that's extraordinary.
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The impossible has been.
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Oh, that is sensational. Jordan Open Chicago. With the lead, Usain Paul is the
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fastest man on the planet.
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You can live your life.
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Welcome back to another episode of the living your legacy podcast. For Inside Success, I am Ray Gutierrez. Joining me today, which I just interrupted his interview session and brought him out to his podcast so he can stick him back into his interview session, is Andrew Olsen, today's operations CEO. Andrew, welcome to the show.
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What's up, Ray? How you doing?
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Fantastic. Thank you for asking. Andrew, what are we going to learn today about you, Andrew Olson?
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What do you want to know? That's a big question.
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Select all. All the above and go right.
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Seriously, where do you want to start, dude?
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Literally, where do you begin? What's getting you out of bed every day, every morning?
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This is my favorite thing to talk about. I could probably go on a soapbox about this, but we. We really get to work with my. My favorite types of people to work with are like the small to midsize businesses. Oh, hell yeah. Because those are the guys that actually write the check.
B
Yes.
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And they're. They're much more invested. They can be. I don't want to. I don't want to discount the big guys.
B
Sure.
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But they can be much more invested in what they do. And we get to come in and be. I mean, almost on a partnership level in their success.
B
Yes, sir.
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When it comes to marketing, we really, we don't just kind of do a design or do a logo or do a brand or whatever. We come in and we really evaluate the landscape of what they're trying to accomplish and say, okay, in our sector of the pie, how can we make you the most successful?
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Right on.
A
And it's such a blessing, especially when we get to see the progress. We get to see things take off. I don't want to say that we, you know, we own the success.
B
Sure.
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We get to be a part of it. On.
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Which is super.
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It's just amazing.
B
So you run a creative agency, a marketing.
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Yep. And we're full service. We do everything cradle to grave. So we, we'll do the market, the overall, Overall marketing strategy. Then we'll come in, we'll evaluate the brand, we'll take a look at. Okay, if you don't have a brand, we can, we can build you one. If you do have a brand, what do you want it to say and what's the reality of what it says? And then how do we bridge that gap? Then everything that comes out of that, the website, the whether, maybe it's a SaaS product, whatever, the graphic design work, the. The branding work, whatever we do really comes out of the strategy that we've picked up at the beginning.
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Right on. Cradle to grave. That's awesome.
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It's crazy.
B
I'm surprised I've never heard that before. I got to steal that from you.
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Take it. Take it, man. Give me a buck every time you use it. Two bucks at this point.
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Two bucks at this point. Three bucks. I can keep going for my friend. Gosh, I got to, I got to ask you, man, like, for as someone that comes from the creative world, obviously in the marketing world, in. It's gotta be kind of tough to be running a creative agency. Everyone out there thinks they are a creative director.
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We do battle that a little bit. But when people see the portfolio of work that we've done, it really changes the landscape. And for example, I'm co owner of another. Of another company called Leveler. And when I first met the founder, Jeff Dehm, we kind of, he kind of came to us with this idea. The idea was so fire that I was like, I have to be a part of this in a bigger way than just doing it. But we, we did the brand work, which was interesting because he hated it at first. We did the brand work, we did the software development, we do all of the marketing. What was crazy is when he first came to us we were kind of, I don't want to say his third pick. I don't mean it like we were the redheaded stepchild. But he had gone to other agencies and because of the complexity of what he wanted done, they flat out told him no.
B
Right on.
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We took the challenge head on. And it has been a challenge. We've been doing it for three and a half years, but it's been incredible. We just launched the product a couple of months ago and we're already seeing success with it.
B
Cool. Are you, are you, how do you hire? How big is your team? Are you local or do you outsource to. To the, to our good old friends in the other side of the world?
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Okay, so this is a. I get this question a lot too. And I. One of the things that I'm super proud of is that everybody that we employ is 100% US based.
B
Hell yeah.
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If I can. And it's expensive, but worth it. It's worth it and it's. And I'll tell you why, if I can, I want them in our office. And the reason for that is because when I, when I first bought pdg, so give you the start of the story. I was in college. The owner, the founder of PDG was a professor of mine.
B
Right on.
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And one day I was going to move to Kansas City where we have our second office and try to start up there because I was always competing with the guy, always competing and always losing. And I finally got the guts one day to walk into his office and said, you know, hey, if you want to sell, I'm interested in buying. And he was kind of like, eh, nah, you know. And I was a 24 year old idiot at the time. I'm a 38 year old idiot now.
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I'm a 42 year old idiot.
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There we go, there we go. The next day, the next day I had an offer in my email. And so for the next year we spent going through it. And I really was focused that whole year on preparing myself for business. I had a little business in college just doing graphic work on the side. But this was the big leaks, right? Yeah. And I was like, numbers, numbers, numbers. And about six months into this business, I realized it had absolutely nothing to do with numbers. It was all people. Oh, thousand percent, thousand percent. That's why to kind of roll back to the beginning. That's why, you know, where our hiring process is so unique. We take between 90 and 120 days to hire everybody. It's got five external steps, 12 internal steps on you and we actually have our core principles and our operating principles and our core, our core beliefs are hanging on these two giant banners in our office. And it's not just something that we talk about. It's something that we actually live.
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And you got to feel it in the moment.
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You walk 100%. We talk about that process.
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It's like, what's your.
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Right.
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Like what's your lead voice? Exactly.
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And we talk about this during the interview process. And again, here's, here's my, my philosophy when it comes to hiring. The reason that we take so long to hire is it's kind of like dating. Right. Not only are we interviewing them, but they're kind of interviewing us. And I don't know if you have to cut this out, but it's kind of like if you've got a bunch of thoroughbred horses and a bunch of asses pen together.
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Yep.
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Right. You, if you have that finish line two feet from the gate, you fling it open, everybody's going to cross. If you put that, that finish line five miles from the gate, only the thoroughbreds are going to make it to the end. So we really value the people that we bring on. And our turnover is almost nothing.
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Wow.
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So if I can hire locally, I do. I do have a couple of team members that are out of state.
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Sure.
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But they're all American.
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Awesome. Do. Are you actively recruiting? Do you. How do you keep it fresh? And when do you burn down the Canva offices?
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I never, ever, ever turn down an interview because the. In the first, the first interview called the drive by. 30 minutes long. We don't even talk about the job.
B
Yeah. You never do.
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You and I take them out of the office. So we'll go get a beer. You'd be surprised.
B
A lot of folks don't comprehend what you're trying to do there.
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They're like, huh? And what's crazy is the things.
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Creative age, it's a whole different ball.
A
Yeah. And you're going to be surprised the things people tell me.
B
Oh, for sure.
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They don't look at me as a boss when we're sitting at a booth or a bar, you know. So you asked me another question. When we're going to burn down the Canva offices.
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Yeah. Like how much of your funk is the guff is Canva at this point? I know five, 10 years ago was it was.
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It was. It was all hands on.
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It was all Photoshop indesign. I get it. You're. You're speaking to, you're speaking to the choir.
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Well, I guess I Should ask you when you're free to hold a torch, but in all reality, how do you
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join them at this point?
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Because it's like, really, we do utilize some tools like that, but for the most part, because of the projects and the types of projects that we work on, we still do a lot of the hardcore creative stuff.
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You have to.
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Yeah.
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Which is what you're charging. Right. Your clients are charging for. You're charging your clients for the experience, for the fact that you've lived. 33. How old were you?
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I'm 38 now.
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38 years. That's a lot of experience. Ain't no Canva software nerd that designed it understands what that is. Sure, you've got a piece of software that can do all these cool things and optimize your workflows, but you really need that intuition, which is priceless.
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So it is. And it. I've got, I've got so many, like, fun little sayings that I, that I use. And what's interesting is not all of them have been said by me. You know, if they say a picture is worth a thousand words, you got to finish that sentence. What's it saying? To who? Yeah, right. That's where you. That's where our expertise comes in.
B
Right on.
A
And then another. He's a client, but also a dear friend of mine also said to me, he said this to a client in front of me and it almost dropped my jaw. But he said, you know, at pdg, they, they tell stories and they use words when they have to.
B
Right on.
A
I love that.
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Oh, for sure.
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It's such a succinct way of saying, in a little nutshell, exactly what we do.
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For sure. That's why I always, like always, like, take pride in going. Well, there's videographers that shoot weddings and quinceaneras, but then there's cinematographers that are filming a moment.
A
Exactly.
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And experience and understand lighting fundamentals, temperature, rooms, frequencies, and when to call action, when not to. Because they quite know that the frequency of energy ain't quite there yet. Wait for it and call it. Now capture the moment. And cut.
A
I always love the, the behind the scenes stuff. When you hear an actor talking about how a director like got them into that moment.
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Yeah, yeah.
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It's always. I'm always intrigued by that because I'm like, wow, there's so much more than just, okay, go say these lines.
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No, it's way more than that.
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So much.
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Yeah. Imagine waking up at three in the morning to have your call time be at 4 to sit in a room with makeup for 4 hours and then deliver 2 lines. Got paid an astronomical amount of money. But you, your job is to say those three lines right on cue. Because you have about $50,000 worth of production a minute to say that goddamn line exactly. Better say it under three takes or you're fired.
A
Exactly. And go.
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And go. Brad Pitfall in the blank. Whoever you are, who's ever gonna sell the movie? We're all waiting. You did it. Good. Now let's move on.
A
And you sucked at it. Do it again.
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And do it again.
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Yeah, yeah.
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And not do it again. Because we've. Yeah, it's. It is quite the art. And that's why I enjoy folks that kind of get the. The. The. The theatrics of the theater of the production. Because at the end of the day, it's really just theater for the client.
A
Right.
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The. And the director's chair, which I'm sure we've all been there. And it's really just like, why is that happening? Why am I paying for that? And the director is speaking to. It's a whole symbiotic unit, which is why I love facts of folks that run their own creative agencies. Because that is what it is. It's agency first and then creative. Because we're all working together to hurry up and wait for the moment. There is capture.
A
And what you. So what you just captured is we get to see this every day. Sometimes we're sitting around our conference table and we'll have the client there and we're working on a marketing strategy. And one of my favorite moments is that pensive moment when they're sitting there going, what's the answer to this?
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Yeah.
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How do we fix this problem? That's where we get to come in and really kind of save the day.
B
Yeah, yeah, yeah.
A
You know, and sometimes they'll have input, and we never shy away from input because ideas only get stronger when they're challenged.
B
Absolutely. Good for you, man. That is a great way of looking at it. And a lot of folks need to hear that. So Operation CEO, Talk to me through your. Your. Your service. And how have you merged your service as a vet with your day to day war on. On business?
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It's a good way to look at it. So I. I joined the military when I was 17. My parents signed a waiver so that I could go. Went to boot camp at Fort Jackson, South Carolina. Missed that place. We had a lot of fun there. I had a really good group of guys that I went through with. You're Just picturing.
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I'm just nodding and smiling, man. Seventeen going for it. Hell yeah.
A
And it makes all the difference when you've. Guys are like in the, in it to play the game at boot camp. When you've got the, the suckers, it just drags everybody down.
B
Yeah.
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No, Never forget, my drill sergeant was drill sergeant Senior Drill Sergeant Huff. He ran the entire cycle. So not only did he run a bunch of other platoons, but he ran ours. And that guy was just this big seven foot black bikini. Oh, my God. When he came, when he came in the room air moved away.
B
Oh.
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I mean, he just displaced everything.
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Amazing.
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So went from since I was I already an assignment to a unit, so I was able to wear all of my, all of my insignias and all that, which got me into more trouble than I think it was worth. I'll never forget one time, it was pretty close to the last month we were there. And because I'm wearing all my name tapes and all of that stuff and my, my insignia, I remember that. We're. We're in the bay floor, it's a Sunday, and we're just cleaning. We're just. It's just stay away from us day. And one of the drill sergeants in the drill sergeant area, he kind of opens the door and he peeks his head out and you're like, oh, God, don't pick me. I wasn't in the back. I wasn't in the front. I was in the middle, so I was safe.
B
Yeah.
A
No, no, no. He just goes, olsen. So I walk in there, I go into the room, they're drinking beer, watching football, having pizza, you know, and he just goes, parade rest. So I'm standing there, parade rest. And it was like I was just a painting on the wall at that point. He comes up and he's taking all my crap off. Goes and sits down and they start playing darts with me. They just started throwing stuff, trying to get it to stick. I stood there for probably three hours.
B
Yep.
A
While they were just, you know, BS and telling stories or whatever. Super fond memory of boot camp for that.
B
Yeah, but you're being challenged, you're being tested.
A
Super fun. I mean, I got to see a different side of them too. But at the same time, like I said, I was not there. I wasn't painting on the wall. Yeah. Several years later, got the call, went to Iraq for my first tour. And we were kind of stationed all over the place. We started in the south, which was pretty tame. I think the most we ever had to suffer was Some SAF every now and some small arms fire every now and again. Rocket fire, mortars maybe. And then we kind of traveled back and forth. I was on a QRF team there, a quick response force team. And then also I was kind of part of a convoy protection team. We would go back and forth between on Nazareh and Baghdad in that area. Back and forth.
B
Wow.
A
So my MOS, my military occupation, specialty was field artillery. I was first 147 field artillery and didn't get to do it. Everybody knocks doors. You know, that's your, that's your job first. They always tell you that. Infantry first. They're MOS second. But my MOS qualification school was super fun because I actually got to fire rockets and stuff.
B
Nice.
A
So that was legit.
B
Nice. Gosh. How do you transition back to, to being a civilian?
A
You don't.
B
You don't. I'm like, like you're using all these amazing terms and like, wow, humans being so. It sounds so boring.
A
Well, you know what's crazy? I remember. So when I was getting ready for this, I was pulling all these pictures out, right?
B
Sure.
A
Which I don't have very many. We just didn't have time to snap photos. I. I know that sounds odd. I did have a camera. I didn't have a camera phone, but didn't get. We just didn't. I was always. Because I was always on deck. I was a gunner. So we just didn't have time to do all that stuff. But I remember looking at the pictures, I had six weapons assigned to me. Probably. I'm not. I don't know how much all that stuff is worth, but I had an M2, a 50 caliber machine gun. Mine, my responsibility. My regular M4. I had a grenade launcher on the bottom of my M4. I had a Beretta. I had a Mark 19, which is a chain link grenade launcher. We used to joke around where like some guy was like, I want all of that way over there blown up. Repeatedly. I mean, that thing, you just, you just hold the butterflies down. I think we did.
B
Oh, Jude. Oh, God, the base. So, gosh, what is your day to day now? What is. What is. Why are you here? Why do you think you've been chosen to tell your story for Operation CEO?
A
Probably because of marketing. I'm a really good bullshitter.
B
Nice.
A
Yeah. No, I'm teasing.
B
No, sir, that's pr, not marketing.
A
Right, right. Yeah, yeah, that's true. I think what's really fun about being an entrepreneur is every morning, this is how I feel. And whether it's true or not is could be argued, but I feel like every entrepreneur wakes up and the world spins because we get up and push it with our feet. You know what I mean? We get up and we spin it, you know? And that's what drives me every day. And really, my team is what drives me. I have such an incredible team. I don't just get to go to work. I get to run to work.
B
Hell, yeah.
A
You know what I mean? I think you spend more time with the people you work with and the people you live with.
B
Absolutely.
A
And so having, again, it goes back to that culture. Having that culture of people is incredible. And the clients we get to work with again, every day, it feels like there's just these tiny explosions of success.
B
Yes.
A
And I get to live that.
B
Yes, sir. Yeah, you're preaching to the choir here. Because every. Every single time we. We have these studios, but these studios are really designed to foster folks like you to hear your stories.
A
Yeah.
B
Gosh, I'm so lucky that. That Rudy just said sayonara. I'm like, all right, I'll start podcasting. I get the joy. I'll get the joy of. Of interviewing folks like you. Kofi gets the joy of interviewing you now, man.
A
Yeah, we'll see about that. He almost kicked me out of my. My first two question.
B
Oh, gosh. No, it was not, sir. You're rocking it, man. Don't, don't, don't. All right, bubba, we're going to wrap this up.
A
Sweet.
B
How can folks learn? And how can folks learn more about you and find out more about.
A
So obviously, we've got a website, pdg, creative.com youm can follow us on social media. I love. I love, love, love talking about the work that we do. So honestly, if they just give me a call, I. My. My advice is about worth what you pay for it. And the first call is always free.
B
Oh, dude. So discovery call.
A
The discovery call.
B
Yeah, I'm going to take you up on that, Andrew, because I'm. I'm a creative director myself, but I've always wanted to just, like, hand it off to someone else and, like, what's your take on it?
A
Because you'd be surprised. I know we got to wrap it up, but, like, getting a different perspective helps to shape that, so.
B
Well, yeah, that would be really. That would be a learning experience for me to be like, I really just want to enjoy these other things, and I want to release my grip on what this thing is. And I really feel like with. Especially with your background and our bond. I'm like, I think you, you'll understand what I'm trying to achieve some. Some new fresh eyes on this.
A
Let's do it.
B
Andrew, a pleasure. Just making sure that. Is your name Olison or is it Olsen?
A
Olsen. The E is silent. We're Scandinavian. So we put. We put both the E and the O in there just to throw people.
B
You mean you Scandinavians and you. This gorgeous eyes.
A
Thank you.
B
That's a Scandinavian thing.
A
It is.
B
Oh, yeah.
A
Tell the ladies that too.
B
Yeah, no, don't do that because I. One of my ladies was Scandinavian with the creepy cool eyes that you do Now I'm getting all sorts of PDS thing. Let's wrap this up up before I start crying again.
A
Yeah, right.
B
This is Andrew Oleson and I am Ray Gutierrez. And we are inside. Success.
Episode: How a College Student Bought His Professor’s Business
Host: Ray Gutierrez (for Rudy Mawer)
Guest: Andrew Olsen, CEO of PDG Creative
Date: June 10, 2026
This episode explores the remarkable journey of Andrew Olsen, who transitioned from being a college student to the CEO of a creative agency he bought from his own professor. Andrew discusses the realities of running a full-service creative agency, touches on his military background, and shares candid insights about hiring, company culture, and the challenges of building a legacy. The conversation is relaxed, candid, and peppered with memorable stories and actionable wisdom for entrepreneurs and creative leaders.
"I finally got the guts one day to walk into his office and said, if you want to sell, I'm interested in buying." (00:00, Andrew Olsen)
"About six months into this business, I realized it had absolutely nothing to do with numbers. It was all people." (05:46, Andrew Olsen)
Approach & Philosophy:
"We come in and we really evaluate the landscape of what they're trying to accomplish and say, okay, in our sector of the pie, how can we make you the most successful?" (02:27, Andrew Olsen)
Hiring and Team Building:
"It's kind of like dating...If you have that finish line five miles from the gate, only the thoroughbreds are going to make it to the end." (07:17, Andrew Olsen)
"You're charging your clients for the experience, for the fact that you've lived...You really need that intuition, which is priceless." (08:54, Ray Gutierrez)
"At PDG, they tell stories and they use words when they have to." (09:28, Andrew Olsen)
"Ideas only get stronger when they're challenged." (11:55, Ray Gutierrez)
Service Background:
"My MOS qualification school was super fun because I actually got to fire rockets and stuff." (15:28, Andrew Olsen)
Transition to Civilian Life:
"Every entrepreneur wakes up and the world spins because we get up and push it with our feet." (16:57, Andrew Olsen)
On the Reality of Entrepreneurship:
"I realized it had absolutely nothing to do with numbers. It was all people."
(05:46, Andrew Olsen)
On Hiring Philosophy:
"If you have that finish line five miles from the gate, only the thoroughbreds are going to make it to the end."
(07:17, Andrew Olsen)
On Creativity vs. Tools:
"At PDG, they tell stories and they use words when they have to."
(09:28, client of Andrew Olsen, as related by Andrew)
On Agency Life:
"It's agency first and then creative. Because we're all working together to hurry up and wait for the moment. There is capture."
(11:07, Ray Gutierrez)
On Motivation:
"I have such an incredible team. I don't just get to go to work. I get to run to work."
(17:27, Andrew Olsen)
Andrew Olsen’s journey from student to owner, veteran to creative leader, is rich with lessons in initiative, resilience, and the value of human connection. Listeners interested in Andrew’s work or PDG Creative can visit pdgcreative.com or reach out for a (free) discovery call, as Andrew encourages open dialogue and new perspectives.
Episode Takeaway:
Business is ultimately about people, story, and the willingness to embrace both challenge and collaboration—a message powerfully delivered through Andrew Olsen’s lived experience and candid storytelling.