The #1 Business Secret I Learned from Shoveling Snow at Age 11

Winning at Business and Life

January 6, 2021

“If you’re the leader, you shouldn’t be the smartest person in the room.” On the rapid-fire podcast Winning and Business In Life, Professor Pete Alexander peppers me with seven pointed questions in seven minutes! We talk about the importance of focusing on a few critical tasks while letting go of the trivial many.

We also talk about the importance of empathy—not just for the client or customer, but also for your team. If you empower your team to do their job, praising their accomplishments, grooming them for promotion without worrying whether they’ll take your job … that’s when you get great work out of them.

We also talk about … 

  • Why lean times can be good for businesses in the long run.
  • What makes me smile the most in my entrepreneurial life.
  • What business leaders I think Professor Pete should interview next.

About the Show: Professor Pete Alexander is the host of the Winning at Business and Life.

Full Transcript

Professor Pete Alexander: 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 One: In a few sentences, please tell me who you are and what you do.

Dylan Ogline: All right, let's do it. Well, Pete thanks so much for having me, my name is Dylan Ogline. In a few sentences, I am the founder of Ogline Digital. We're a Direct Response Digital Marketing Agency. 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.

Professor Pete Alexander: Dylan it's great to have you on the show.

Question Number Two: What is something that makes you smile and/or laugh about working in your industry?

Dylan Ogline: I'll go with the education business. With that, that's really been a focus of mine over the last, say two years, helping people start their own businesses or quit their job or something. Or maybe they had an agency and they're able to grow it enough to where they can quit their job or have the lifestyle that they want. That's been extremely rewarding, so I will say that puts a smile on my face, I'll go with that one.

Professor Pete Alexander: I love it and I can hear the passion in voice, so it's really great.

Question Number Three: I have a fictitious book with all of the answers for business.

Dylan Ogline: I love that you actually have it.

Professor Pete Alexander: Exactly. What chapters would you think most companies should read?

Dylan Ogline: I can do two here, right?

Professor Pete Alexander: Sure.

Dylan Ogline: All right, I'm going to do two. Pre-show I was thinking about this because I had a recent event with a client of mine, this was for my agency. The chapter would be empathy. Basically, when I'm talking empathy, I'm talking about empathy for your team, for employees. A lot of business leaders lose track of that and they just think that they're cogs in the wheel. But just remember that your team, those are real people. And if you slim down your staff, you're impacting somebody's life. So, empathy for your team. You also probably need empathy for your customers as well, but in 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 those critical few and letting go of the trivial many. That would be my answer there.

Professor Pete Alexander: I love it. Both of them are pretty impactful, definitely, so thank you for sharing those.

Question Number Four: Other than the generic work harder, have a create attitude and care for customers, what advice or insight would you give to other business leaders?

Dylan Ogline: I would go back to answer three, I think that's a really good one. Right now, I also think my advice, with COVID going on, economic downturn to a certain degree, realize that when we're going to through bad times, typically it ends up being a good thing. Almost a resent, clearing the slush out of your business, clearing the inefficiencies out. I think realizing that things aren't as bad as they are and that they eventually will get better.

I'm going to say that and I'm going to use two here as well. My second would be bring on people that are smarter than you. You don't want to be egotistical and be afraid of people who are smarter or know how to run the business better than you do. 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.

Professor Pete Alexander: I love that second one as well, because there's been so many times in my career where I have worked with leaders who were afraid of having people who seemed like they were smarter because they said, "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. If you take that attitude you're going to get some good quality work from those people. But if you hold them down because you're worried about them trying you up or something, it's a real negative. Would you agree?

Dylan Ogline: One hundred percent. 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." 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 you're the smartest person and you're the leader, you made some wrong choices and you need to hire some different people. You should not be the smartest person in that meeting.

Professor Pete Alexander: Oh, it's totally true.

Dylan Ogline: One hundred percent of the time.

Professor Pete Alexander: It is so true. I can think about easily dozens, if not hundreds of times I've thought that same thing in a meeting.

Dylan Ogline: You don't want to be the smartest.

Professor Pete Alexander: Exactly.

Dylan Ogline: That's not a good idea.

Professor Pete Alexander: Question Number Five: What other business leader like yourself would you like to acknowledge and invite to be on my Podcast?

Dylan Ogline: Going into this, I'm going to with two. I know one's really big and that's Tim Ferris. But I don't think he's going to be a guest on pretty much anybody's podcast. The other one would be Sam Ovens. 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.

Professor Pete Alexander: Perfect. Well, I'm going to reach out to both of them and let's see what happens. I appreciate those recommendations. Our final question, Question Number Six: Please tell me about your first job.

Dylan Ogline: Oh yeah, we were talking about this pre-show. My first actual job, I was an employee and I think it's the only one I've actually had where I was an employee, was I ran the cotton candy stand at a local racetrack. There are no real lessons there. Before that though, the actual first thing that I did to make money was 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 realize this until I recently had a conversation about my first foray into capitalism.

Realizing that people were willing to pay be effectively $10 to $15 an hour to 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 this cute little kid, hustling, trying to make some spending money to buy PlayStation games or whatever. How you appear actually matters to the marketplace. That is my lesson and takeaway from the first job.

Professor Pete Alexander: I love it. Great story too. It sounds like because you were shoveling the snow and mowing the grass, you even knew how to make sure you had work throughout the whole seasons.

Dylan Ogline: Oh absolutely. Yeah. It started with the shoveling and then summer came, and I was broke. So, I was like, "Well, what can I do now?" And they couldn't say no to me I was like 11 or 10 or something like that, so of course they had to say yes. I charged a premium price baby, I mean I was the premium solution in the marketplace, so I charged appropriately.

Professor Pete Alexander: I love it. Great story. Dylan thank you so much for being on the show. How can people find you?

Dylan Ogline: Sure thing. My website is and you can also find me on LinkedIn, Facebook, Instagram @Dylanogline.

Professor Pete Alexander: Perfect. This is Professor Pete Alexander with the Winning at Business and Life Podcast, thanks for listening.