In this rapid‑fire interview, Professor Pete Alexander sits down with Dylan Ogline, founder of Ogline Digital—a direct‑response digital marketing agency—and creator of the Agency 2.0 education program that teaches aspiring entrepreneurs how to launch their own agencies. Dylan shares what makes him smile (helping people build and quit their jobs through his training), the two "chapters" he believes every company should read—empathy for team members and focusing on the critical few services—and advice for leaders navigating economic downturns, emphasizing that recessions can act as a reset that clears inefficiencies. He stresses the importance of hiring people smarter than yourself and empowering them with credit and flexibility. Dylan recommends Tim Ferriss and Sam Ovens as fellow business leaders worth inviting to the podcast. He recounts his first paid work shoveling snow and mowing lawns, extracting a lesson about pricing based on perceived value and the power of premium positioning. The episode closes with Dylan’s contact details (website and social media).
Chapters
This is Professor Pete Alexander with the Winning at Business and Life podcast, where business leaders share their insights. It is 6 questions in 7 minutes because successful business leaders are busy and rarely have more time to spare. So let's get to it. Question number 1: In a few sentences, please tell me who you are and what you do.
Alright, let's do it. Well, Pete, thanks so much for having me. My name is Dylan Ogline. So in a few sentences, I own— I'm the founder of Ogline Digital. We're a direct response digital marketing agency. And I also own an education company where I have a training program called Agency 2.0, where I teach people how to start their own digital marketing agency.
Dylan, it's great to have you on the show. Question number 2: What is something that makes you smile and/or laugh about working in your industry?
Uh, smile or laugh, uh, so I'll go with the education business, uh, with that, uh, which has really been a focus of mine over the last, say, 2 years, helping people, uh, helping people start their own businesses or, you know, quit their job or something, and, or, or maybe they had an agency and, you know, they're able to grow it enough to where they can quit their job or have the lifestyle that they want. Uh, that's been extremely rewarding. So I, I will say that, that puts a smile on my face. I'll go with that one.
I love it. And I can hear that passion in your voice. So it's really great. Question number 3, I have a fictitious book with all the answers for business.
I love that you actually have it.
Exactly. What chapter would you think most companies should read?
Can I go? I could do 2 here, right? Okay, sure. Okay. All right. I'm going to do 2. So pre-show I was thinking about this because I had a recent event with a client of mine, and this is for my agency. So the chapter would be empathy. Basically, just when I'm talking empathy, I'm talking about empathy for your team, for your employees. A lot of business leaders lose lose track of that and they just think that they're, you know, cogs in the wheel. And, but just remembering that, you know, your team, that those are real people. And if you slim down your, your staff, you're impacting somebody's life. So, so empathy for, for your team. You also probably need empathy for your customers as well. But, but in my particular sense, and My particular chapter in the book would be empathy for your team members, your employees. The other one would be focusing on the essential, the critical few tasks, services, offerings, focusing on this critical few and letting go of the trivial many. That would be my answer there.
I love it. Both of them are pretty impactful, definitely. So thank you for sharing those. Question number 4. Other than the generic work harder, have a great attitude, and care for customers, what advice or insight would you give to other business leaders?
I would go back to answer 3. I think that, that's a really good one. Right now, I also think my advice, because COVID going on, economic downturn to a certain degree, Realize that when we're going through bad times, typically it ends up being a good thing, almost a reset, clearing the slush out of your business, clearing the inefficiencies out. So, I think realizing that things aren't as bad as they are and that they eventually will will get better. I would say that, and I'm going to use two here as well. My second would be bring on people that are— bring on people that are smarter than you. You don't want to be egotistical and be afraid of people that are smarter or know how to do— run the business better than you do. You know, if you're the leader, you shouldn't be the smartest person in the room. So bring on team members that are smarter or better equipped to do the jobs than you are.
I love that second one as well, because, you know, there's been so many times in my career where I have worked with leaders who were afraid of having people that seemed like they were smarter because they, oh my gosh, they're going to take my job or something. And to me as a leader, I've always felt like I want to have the good people below me because my job as a leader is to help cultivate them and promote them, whether it's promoting them within the organization that we're in or getting them a job outside to help them with their career. And, you know, if you take that attitude, you're gonna get some good quality work from those people. But if you hold them down because you're worried about them trying to show you up or something, it's just, it's a real negative. Would you agree?
100%, absolutely. You should empower the people on your team, give them the flexibility to shine, give them credit, when they do something right, like shouts to the whole team, like so-and-so did a great job. It cannot enough be, enough cannot be said for just how important that is. And just bring on people that are smarter than you. If you are holding a meeting, whether it's Zoom or an actual in-person meeting, if you get the impression that like you're the smartest person and you're the leader, You made some wrong choices. You need to hire some different people. You should not be the smartest person in that meeting.
Oh, it's totally true.
100% of the time.
It is so true. I could think about, oh, easily dozens if not hundreds of times I've thought that same thing in a meeting.
You don't want to be the smartest.
Exactly.
That's not a good idea.
Question number 5: What other business leader like yourself would you like to acknowledge and invite to be on my podcast?
Uh, so, so going into this, uh, I'm gonna go with two.
I don't—
I know one, one's really big, and that's Tim Ferriss. Uh, you know, everybody, everybody knows Tim Ferriss, uh, but I don't think he's, he's gonna be a guest on pretty much anybody's podcast. The other would be, uh, Sam Ovens. Uh, uh, Sam has been an incredible teacher for me. I've learned a ton from him. I don't think he does podcasts, unfortunately, but if you could get him, I think he would be an absolutely— he's great on video. He's one of the smartest people I know. So yeah, Sam Ovens, absolutely.
Perfect. Well, I'm going to reach out to both of them and let's see what happens. So I appreciate those recommendations. And our final question, question number 6, please tell me about your first job.
Oh yeah, yeah, we were talking about this, uh, pre-show. Uh, so my first actual, like, job— I was an employee, and I think it's the only one I've ever actually had where I was an employee, uh, was I ran the cotton candy stand at a local racetrack. But there's, there's no real lessons there. Before that though, the actual first thing I did to make money was, uh, shoveling sidewalks and driveways in the winters in Pennsylvania, or mowing grass, which is not exciting. But the lesson that can be taken away from that is pricing based on value, which I didn't, I didn't realize this until I recently had a conversation about my first foray into capitalism. But realizing like, people were willing to pay me effectively $10 to $15 an hour to, you know, mow their grass or shovel their sidewalk, which is a lot of money back then. And they were willing to pay me that much because I was like this cute little kid, you know, hustling, trying to make some spending money to buy like PlayStation games or whatever. So, you know, how you appear actually matters into the marketplace. So that is my lesson and takeaway from the first job.
I love it. Great story too, because it sounds like because you were doing this shoveling the snow and mowing the grass, you even knew how to make sure that you had work throughout the whole seasons.
Oh, absolutely. Yeah. It started with the shoveling and then like, you know, summer came and I was like, I was broke. So I was like, well, what can I do now? And they couldn't say no to me. I mean, I was like 11 or 10 or something like that. So of course they had to say yes. And I charged a premium price, baby. I mean, that was the premium. Premium solution in the marketplace. So I charged, I charged appropriately.
I love it. Great story. So Dylan, thank you so much for being on the show. How can people find you?
Sure thing. My website's DylanO'Brien.com, and you can also find me on the LinkedIn, Facebooks, the Instagrams @DylanO'Brien.
Perfect. This is Professor Pete Alexander with the Winning at Business and Life podcast. Thanks for listening.
