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Living Your Legacy

How a College Student Bought His Professor’s Business

10 Jun 2026

Transcription

Transcript generated automatically by AI and may contain errors.

Chapter 1: Why did Andrew Oleson decide to buy his professor's business?

0.031 - 20.014 Andrew Oleson

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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19.994 - 38.883 Andrew Oleson

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. We're full service. We do everything cradle to grave.

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38.903 - 51.802 Andrew Oleson

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?

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54.506 - 58.451 Unknown

It spans the globe like a super high school internet.

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Chapter 2: What lesson shifted Andrew's focus from numbers to people?

60.554 - 63.979 Andrew Oleson

Today, Apple is going to reinvent the fun.

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63.999 - 72.872 Unknown

It's not over until I win. The Living Your Legacy podcast. For those who live to leave a legacy.

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76.711 - 91.027 Unknown

Welcome back to another episode of the Living Your Legacy podcast.

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91.207 - 109.078 Ray Gutierrez

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 his interview session, is Andrew Olson, today's operations 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?

109.098 - 117.816 Ray Gutierrez

What do you want to know? That's a big question. Select all of the above and go. Seriously, where do you want to start? Dude, literally, where do you begin?

117.896 - 137.571 Andrew Oleson

What's getting you out of bed every day, every morning? That's my favorite thing to talk about. I could probably go on a soapbox about this, but... 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 much more invested. They can be.

137.591 - 152.454 Andrew Oleson

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 don't just kind of do a design or do a logo or do a brand or whatever.

152.914 - 173.204 Andrew Oleson

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? 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 own the success, but we get to be a part of it, which is super. It's just amazing.

Chapter 3: What challenges did Andrew face when launching a new product?

715.71 - 732.619 Ray Gutierrez

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 service and how have you merged your service as a vet with your day-to-day war on business?

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732.819 - 748.106 Andrew Oleson

That's a good way to look at it. So 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, which makes all the difference.

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748.126 - 750.93 Ray Gutierrez

I'm just nodding and smiling, man. 17 going for it? Hell yeah.

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750.99 - 775.625 Andrew Oleson

And it makes all the difference when you've got a group of guys that are in it 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. 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 behemoth.

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776.286 - 779.09 Andrew Oleson

Oh, my God. When he came in the room, air moved away.

779.17 - 779.51 Unknown

Oh, sure.

779.53 - 792.906 Andrew Oleson

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 insignias and all that, which got me into more trouble than I think it was worth.

792.886 - 810.813 Andrew Oleson

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 insignia, I remember we're in the bay floor, it's a Sunday, and we're just cleaning. It's just stay away from us day.

811.734 - 824.881 Andrew Oleson

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. Yeah. 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. No. He just goes, Olsen.

Chapter 4: How does Andrew's hiring process create a high-performance culture?

1064.561 - 1073.093 Ray Gutierrez

Yeah. You're preaching to the choir here because every single time we have these studios, but these studios are really designed to foster folks like you to hear your stories.

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1073.193 - 1073.373 Unknown

Yeah.

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1073.754 - 1083.708 Ray Gutierrez

Gosh, I'm so lucky that Rudy just said sayonara. I'm like, all right, I'll start podcasting. I'll get the joy. I'll get the joy of interviewing folks like you. Kofi gets the joy of interviewing you now, man.

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1083.728 - 1087.914 Andrew Oleson

Yeah, we'll see about that. He almost kicked me out of my first two questions. Were that terrible?

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1088.074 - 1089.961 Ray Gutierrez

Oh. Oh, gosh. No, I was not, sir.

Chapter 5: How does Andrew ensure a strong company culture?

1090.081 - 1100.318 Ray Gutierrez

You're rocking it, man. Don't, don't, don't. All right, Bubba. We're going to wrap this up. Sweet. How can folks learn more about you and find out more about?

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1100.585 - 1118.213 Andrew Oleson

So obviously we've got a website, pdgcreative.com. You can follow us on social media. I love, love, love talking about the work that we do. So honestly, if they just give me a call, my advice is about worth what you pay for it. And the first call is always free. Oh, dude.

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1118.233 - 1119.094 Ray Gutierrez

The discovery call?

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1119.174 - 1120.096 Andrew Oleson

The discovery call.

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1120.376 - 1127.908 Ray Gutierrez

Yeah. I'm going to take you up on that, Andrew, because 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?

1127.888 - 1134.397 Andrew Oleson

Cause you'd be surprised. I know we got to wrap it up, but like getting a different perspective helps to shape that so well.

1134.597 - 1151.78 Ray Gutierrez

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'd like some, some new fresh eyes on this. Let's do it.

1152.16 - 1154.824 Ray Gutierrez

Andrew, a pleasure. Just making sure that is your name.

1154.872 - 1161.679 Andrew Oleson

Olesen or is it Olsen? The E is silent. We're Scandinavian, so we put both the E and the O in there just to throw people off.

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