Living Your Legacy

How a College Student Bought His Professor’s Business

20 min
Jun 10, 2026about 1 month ago
Listen to Episode
Summary

Andrew Olson, CEO of PDG Plus Creative, shares his journey from college student to creative agency owner after buying his professor's business. He discusses building a full-service creative agency focused on branding and marketing strategy for small to mid-sized businesses, emphasizing company culture and people-first hiring practices over technical skills.

Insights
  • Successful business ownership is fundamentally about people and culture, not just numbers and financial metrics
  • A rigorous, extended hiring process (90-120 days) with multiple interview stages creates better cultural fit and dramatically reduces turnover
  • Full-service creative agencies differentiate by understanding client strategy and landscape before executing design, not just delivering design assets
  • Military discipline and leadership principles directly translate to building high-performing teams in creative industries
  • Keeping teams US-based and in-office, despite higher costs, creates better collaboration and cultural cohesion than distributed remote models
Trends
Creative agencies shifting from execution-focused to strategy-first service modelsEmphasis on company culture and values as primary hiring criteria over technical skills aloneSmall to mid-sized businesses becoming preferred clients for creative agencies due to higher engagement and partnership potentialIn-office team models gaining renewed emphasis in creative industries for collaboration and culture buildingCreative professionals leveraging military and leadership experience to build disciplined, high-performing teamsFull-service agency model consolidating multiple capabilities (strategy, branding, design, development, marketing) under one roofExtended discovery and hiring processes becoming competitive advantage for talent retentionStorytelling and strategic narrative becoming more valued than design tools and software capabilities
Topics
Creative Agency Business ModelsFull-Service Marketing StrategyCompany Culture and Hiring PracticesBranding and Brand StrategySmall to Mid-Sized Business MarketingLeadership and Team BuildingMilitary Leadership Principles in BusinessDesign and Creative DirectionClient Discovery and StrategyEntrepreneurship and Business OwnershipTalent Retention and Turnover ReductionIn-Office vs Remote Team ModelsBusiness Acquisition and TransitionSaaS Product Development and MarketingCreative Industry Challenges
Companies
PDG Plus Creative
Full-service creative agency founded by Andrew Olson's professor; Olson purchased the business as a college student
Leveller
Co-owned by Andrew Olson; SaaS product company for which PDG Plus Creative provides branding, software development, a...
Canva
Design software tool discussed as example of technology that supplements but doesn't replace expert creative work and...
People
Andrew Olson
Creative entrepreneur and branding strategist who bought his professor's business while in college and built it into ...
Ray Gutierrez
Podcast host conducting interview with Andrew Olson about his business journey and creative agency leadership
Jeff Deem
Co-founder of Leveller SaaS product; client and business partner of Andrew Olson at PDG Plus Creative
Senior Drill Sergeant Huff
Andrew Olson's drill sergeant at Fort Jackson during military boot camp; influential leadership figure in his early c...
Quotes
"About six months into this business, I realized it had absolutely nothing to do with numbers. It was all people."
Andrew OlsonEarly in episode
"We come in and we really evaluate the landscape of what they're trying to accomplish and say, OK, in our sector of the pie, how can we make you the most successful?"
Andrew OlsonMid-episode
"At PDG, they tell stories and they use words when they have to."
Andrew Olson (quoting a client)Mid-episode
"Every entrepreneur wakes up and the world spins because we get up and push it with our feet."
Andrew OlsonLate episode
"I don't just get to go to work. I get to run to work."
Andrew OlsonLate episode
Full Transcript
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. Andrew Olson is a creative entrepreneur, branding strategist and the CEO of PDG plus 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. Our 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, OK, in our sector of the pie, how can we make you the most successful? It's fans, the world like a super high is called into the eldest. 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. The impossible. Oh, that is sensational. Open Chicago with the lead. You said Paul is the fastest man on the planet. You can live your dream. 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 we can stick him back into the interview session is Andrew Olson, today's operation CEO. Andrew, welcome to the show. What's up, Ray? How you doing? Fantastic. Thank you for asking Andrew. What are we going to learn today about you, Andrew Olson? What do you want to know? That's a big question. Select all of the above and go. Right. Seriously, where do you want to start? Dude, literally, where do you begin? What's getting you out of bed every day, every morning? That's my favorite thing to talk about. I can probably go on a soapbox about this, but we we really get to work with my favorite types of people to work with are like the small to mid-sized businesses. Oh, hell yeah. Because those are the guys that actually write the check. Yes. 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. Sure. 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. Yes, sir. 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, OK, in our sector of the pie, how can we make you the most successful? Right on. 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 we own the success. Sure. We get to be a part of it, which is super. It's just amazing. So you run a creative agency, a marketing agency. Yeah, we're full service. We do everything cradle to grave. So we will do the market, the overall marketing strategy, then we'll come in. We'll evaluate the brand. We'll take a look at, OK, 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? Right on. And then how do we bridge that gap? Then everything that comes out of that, the website, the whether maybe it's a SAS product, whatever the graphic design work, the branding work, whatever we do really comes out of the strategy that we've picked up at the beginning. Right on. Creative to grave. That's awesome. It's crazy. I'm surprised I never heard that before. I got to steal that from you. Take it. Take it, man. I just give you a buck every time you use it. I definitely will. Two bucks at this point. Two bucks at this point. Creative to grave, three bucks. I can keep going for my friend. Gosh, I got to ask you, man, like for someone that comes from the creative world, obviously in the marketing world, it's got to be kind of tough to be running a creative agency. Everyone out there thinks they are creative director. We do battle that a little bit. But when people see the portfolio of work that we've done, it really changes a landscape. And for example, I'm I'm co-owner of another of another company called Leveller. And when I first met the founder, Jeff Deem, 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, 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. Cool. Are you are you? How do you hire? How big is your team? Are you local or do you outsource to to our good old friends in the other side of the world? OK, so this is 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 percent US based. Hell, yeah. 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. Right on. 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, nah, you know, and I was a 24 year old idiot at the time. I'm a 38 year old idiot now. I'm a 42 year old idiot. 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. Look at you go. I had a little business in college just doing graphic work on the side. But this was the big leaks, right? 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, 1000 percent. 1000 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. 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. Nice. And it's not just something that we talk about. It's something that we actually live. And you got to feel it when you walk 100 percent. You talk about that. That's like, what's your? Dun dun dun. Right. Like, what's your lead voice? Exactly. 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, you have to pin together. Yep. 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 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. Wow. So if I can hire locally, I do. I do have a couple of team members that are out of state, but they're all American. Awesome. Are you actively recruiting? Do you, how do you keep it fresh? And when do you burn down the Canva offices? I never, ever, ever turned down an interview because in the first, the first interview called the drive by 30 minutes long, we don't even talk about the job. Yeah, you never do. You just and I take them out of the office. So we'll go get a beer. Yeah. You'd be surprised. A lot of folks will comprehend what you're trying to do there. They're like, huh? Well, it's crazy. It's the thing. Creative agency. It's a whole different. Yeah. If you're surprised that things people tell me. Oh, for sure. They don't look at me as a boss when we're sitting in a booth or a bar, you know. So you asked me another question. When we're going to burn down the Canva offices. Yeah. Like how much of your funk is the guff is Canva at this point? I know five, 10 years ago was it was all it was all hands on. It was all Photoshop and design. I get it. What you're you're speaking to speaking to the choir. Well, I guess I should ask you when you're free to hold a torch. But in all reality, how do you join them at this point? Because it's like really, we do utilize some tools like that. For the most part, because of the projects, the types of projects that we work on, we still do a lot of the hardcore creator stuff. You have to. Yeah, which is what you're charging. You're right. Your clients are charging for your charging your clients for the experience, for the fact that you've lived 33 held where you for 38 now, 38 years. That's a lot of experience. Ain't no Canva software, a 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. So it is. And I've got I've got it. 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 into who? Yeah, right? Absolutely. That's where our expertise comes in. Right on. 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. Right on. I love that. Oh, for sure. It's such a succinct way of saying in a little nutshell exactly what we do. For sure. That's why I always like always like take pride in going, well, there's videographers that shoot weddings and kinsengeras, but then there's cinematographers that are filming a moment 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 and quite there yet wait for it and call it now, capture the moment and cut. I always love the behind the scenes stuff. When you hear an actor talking about how a director like got them into that moment. Yeah. Yeah. It's always always intrigued by that because I'm like, wow, there's so much more than just, OK, go say these lines. No, it's way more than that. So much. Yeah. I imagine waking up at three in the morning to have your call time be at four to sit in a room with makeup for four hours and then deliver two lines, get 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. Exactly. And go. And go, Brad Pitt, let the blank, whoever you are, whosoever is going to solve the movie. We're all ready. You did it. Good. Now let's move on. And you shut that it. Do it again and do it again. Yeah. And now do it again because we've yeah, 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, right? The client sitting there in 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 I I love facts of folks that run their own creative agencies because that is what it is. It's is agency first and then creative because we're all working together to hurry up and wait for the moment. There is a good capture. And what you so what you just captured is we get to see this every day. Sometimes we'll be 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 and they're going, what's the answer to this? How do we fix this problem? That's where we get to come in and really kind of save the day. And sometimes they'll have input and we never shy away from input because ideas only get stronger when they're challenged. 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? 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. You're just making them smiling, man. Seventeen going for it. Hell yeah. And it makes all the difference when you've got a group of guys that are like in in that to play the game at boot camp. When you've got the suckers, it just drags everybody down. Never forget my drill sergeant was drill sergeant, senior drill sergeant Huff, he ran the entire cycle. Right. Not only did he run a bunch of other platoons, but he ran ours. And that guy was just this big seven foot black. Oh, my God. When he came when he came in the room, air moved away. Oh, I mean, he just displaced everything. Amazing. So went from since I was I already had 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 in my my insignia. I remember that we're at the 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 was in the front. I was in the middle. So safe. Yeah. No. Now he just goes, Olson. 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 taken 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. Well, they were just, you know, BS and telling stories or whatever. Super fun memory of boot camp for that. Yeah, but you're being challenged. You're being tested. 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 was a painting on the wall. Yeah. Several years later, I 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 saff 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 Anasariya and Baghdad in that area back and forth. Well, so my MOS, my military occupation specialty was field artillery. I was first to 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, your MOS second. But my MOS qualification school was super fun because I actually got to fire rockets and stuff. Nice. So that was legit. Nice. Gosh. How do you transition back to to being a civilian? You don't. You don't. You don't like you're using all these amazing terms and like, wow, humans. You just being so this sounds so boring. Well, you know, what's crazy? I remember so when I was getting ready for this, I was pulling all these pictures out, right, which I don't have very many. We just didn't have time to snap photos. 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. Yeah. 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. We're like, some guy was like, I want all of that way over there blown up repeatedly. I mean, that you just you just hold the butterflies down. I think with the phone phone phone phone phone. Oh, dude. 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? Probably because of marketing. I'm a really good bullshitter. Nice. Yeah. No, I'm teasing. No, sir, that's PR, not marketing. Right. Right. Yeah. Yeah, that's true. I think what's really fun about being an entrepreneur is every morning, I 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. Hell, yeah. You know what I mean? I think you spend more time with the people you work with and the people you live with. Absolutely. 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. Yes, sir. I get to live that. Yes, sir. Yeah. You know, you're preaching to the choir here because every every single time we have these studios, but these studios are really designed to foster folks like you to hear your stories. Yeah. Gosh, I'm so lucky that that Rudy just said, Sirenar. I'm like, I'll start podcasting. I get the joy. I'll get the joy of interviewing folks like you. Kofi gets the joy of interviewing you now, man. Yeah, we'll see about that. He almost kicked me out of my first two questions. Were that terrible? Oh, gosh, no, I was not. Sir, you're rocking it, man. Don't don't don't. All right, Baba, we're going to wrap this up. Sweet. How can folks learn and how can folks learn more about you and find out more about? So obviously we've got a website, PDGcreative.com. You can follow us on social media. I love I love, love, love talking about the work that we do. So honestly, if they just gave me a call, I my advice is about worth what you pay for it. And the first call is always free. Oh, dude, so the Discovery call, the Discovery call. 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. I'm like, what's your take on it? Because you'd be surprised. I know we got to wrap it up. But like getting a different perspective helps to shape that so 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. And I like some some new fresh eyes on this. Let's do it. Andrew, a pleasure. Just making sure that is your name. All the center is at Olson Olson. The E is silent. We're Scandinavian. So we put we put both the E and the O in there just to throw people. You use Scandinavians and you this gorgeous eyes. Thank you. Thank you. Scandinavian thing. It is. Tell the ladies that too. 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 fudious things. Let's wrap this up before I start crying again. Yeah, right. This is Andrew Olson and I am Ray Gutierrez and we are Inside Success.