How the School System MISERABLY Fails Aspiring Entrepreneurs

Let's Have This Conversation

October 26, 2020

“The man who chases many rabbits catches none.” In this episode of Let’s Have the Conversation, I share with Kevin McShann how I spent eight years spinning my wheels in a freezing basement office in rural Pennsylvania, only to discover that I had to ditch nine of the ten ideas I was trying to launch and focus on one of them. It was my ticket out of nearly a million in debt, and into the 7-figure Digital Nomad lifestyle. Today, my educational program Agency 2.0 teaches students to do the same thing (minus the debt).

I explain how the very definition of “work” is changing drastically. Remote work and entrepreneurship have gone mainstream, a development that stands to benefit disabled and historically disenfranchised demographics massively.

We also touch on:

  • How the school system fails aspiring entrepreneurs.
  • How the traditional “college/career/retirement” cycle is failing everyone.
  • How I was able to maintain his nomadic lifestyle even when the pandemic shut down air travel.

About the Show: Kevin McShann is the host of Let's Have This Conversation.

Full Transcript

Kevin McShan: A million dollars in debt and a high school dropout. This forecast may not seem like a recipe for success, but Dylan Ogline used this as his moment of influence and prosperity after scraping 10 business ideas and tired of working in freezing basement, Ogline focused exclusively on digital marketing and that decision is what made him a millionaire. Now, this Pennsylvania country kid, turned Florida Transplant is not on a mission to help other build profitable agencies and successful businesses. He joined me this week to discuss how he found his own secrets to success. I’m Kevin McShan, Let’s Have This Conversation.

Kevin McShan: Hey Dylan, if you’re ready I’ll welcome you to the show. We’re excited to learn all about how you help people build profitable digital agencies. So great to see you this morning and thanks so much for being here.

Dylan Ogline: Absolutely, Kevin. Thank you so much for having me.

Kevin McShan: Dylan, I know that your story began by growing up in a small country town in Pennsylvania and you had dreamed of started 10 businesses before you started focusing primarily of digital agencies. Can you tell me a little about your business journey and how you got to where you are today?

Dylan Ogline: Sure, sure. So, the dream wasn’t to start 10 different businesses and to be working on 10 different projects and bouncing all around. I didn’t realize it was mistake at the time, but where the mistake was is that I was continuously chasing trying to make something work. I was desperate, I spent eight years doing this. A long time I wasted continuously trying to start the new thing, chasing the shiny object, just to try to get something going.

That’s how I ended up having I think it was over 10 different projects going on. The truth was it wasn’t that I had 10 businesses that were going somewhere. I wasn’t an Elon Musk, who was building all these different businesses, I was getting nowhere with any of it because I was going in so many different directions. “The man who chases many rabbits catching none” and I was the epitome of that. I was in so many different directions absolutely going nowhere because I wasn’t putting my focus on at least one single thing.

Kevin McShan: You also said that you were a million dollars in debt. I’m wondering how you remained disciplined to sort of climb your way out of that.

Dylan Ogline: I don’t know how I remained disciplined, that’s a good question. I think it was simply the fact that failure wasn’t an option. I didn’t have something to fall back on, I had to make it work. Eventually, what kind of was key for me was having mentors and having people that I could bounce ideas off of. People that I like to say slapped me upside the head and said, “You’re an idiot for doing so many different things, that’s the big problem.” I also, around the time when I started to get things going, I also started to join masterminds and training programs, I wasn’t just by myself anymore. That really allowed me to--seeing other people who made it work kind of subconsciously was, “Okay, if these people can make it work, you can make it work as well.”

Like I said, at the time I joined a bunch of different training programs and masterminds and I was going through training. I was actually seeking advice. I had great mentors. And then I also was in a community where I could be like, “Okay, these other people followed this advice and they were able to get success.” All of those things hit at the right time for me and that, I think, is what gave me the push to get out of that hole.

Kevin McShan: Now, you also said that you work now with people to build profitable digital agencies and sort remove the guess work to do that. So, can you tell me about the work your doing and how you’re helping people find their digital identity through business?

Dylan Ogline: Absolutely. Before I had 10+ projects, now I have my digital agency, but that pretty much runs itself, I have a fantastic team in place. If I have to work two hours a week to keep that running, that’s putting it high. But I’m able to now put my focus, my time and my energy into something I’m extremely passionate about, which is my training program, Agency 2.0. And like you mentioned, that’s teaches people how to--the idea is that anybody can come into the program. You don’t have to be in the digital marketing space. You could be a soccer mom, you could be a high school dropout like me, or just somebody who just got out college or is in college, anything, with no experience in digital marketing, come into the program. I want to be able to teach you step by step everything you need to know and do to build a six-figure digital agency. That’s the program.

Kevin McShan: I’m curious to know your thoughts on the way people that go to school now are taught digital marketing or business administration and the like. I’m just curious to get your thoughts on the presentation of that and whether you think the education system getting it right and where you think they make stand for improvement.

Dylan Ogline: Sure. I’m going to answer that in a different way here. I believe that work as we know it is drastically changing. You go back 20, 30 years ago--go back 20 years, it was harder for people to start their own business. Working at home was like: How do you work at home? How do you not have an office? How do you not go to the office? And now it is so easy for anybody to start their own business. A lot of the times it’s better for business to work at home, they’re not wasting their time commuting, they can do really focused work. All of those things are changing the nature of work as we know it.

That’s been going on for years, technology is getting better, the cost of starting a business get lower and lower, that all has been happening for years. Now with COVID, that kind of just cracked it up to a 10, where now everybody is working at home. That stigma of starting your own business or working from home, that stigma’s gone now. Where I think education is going wrong in our school systems and whatnot, is we’re still stuck in that pattern of you go to school, you go through high school, then they mostly encourage you to go to college. Then you go get a job and you work a job for 30 years and then you retire. I think that’s done. I think that world is done.

There are so many different things that we’re not teaching people--how to start their own businesses. And it’s not started a digital agency or anything like that, it’s I think a lot of people are going to be independent contractors, they could be writers. And they’re bouncing around from working with different companies because they can now. Now it’s--I just randomly made up a writer--you say you’re a writer, before you had to go to an office and one at one company or whatever, now you can work for 10 different companies throughout the company. Working full-time from home anywhere in the United States or anywhere in the World. Does that answer your question in a roundabout way?

Kevin McShan: Sure it does. My next question, just building on that, I’m not sure if you were aware of this, but October is National Disability Employment Awareness Month. So my next question has to do with asking you, how do you think digital agency and technology can spur the hiring of people with disabilities?

Dylan Ogline: That’s a great question. I believe that this change that we’re going through and the definition of work, and how people work, and working from home, I think it’s going to benefit everybody. But I think it’s going to disproportionately, in a good way, benefit those with disabilities, minorities, women, so many barriers to entry are now being lowered or the glass is being shattered. Think if you have a disability and you wanted to be a writer and you had to go into the office, that’s just more challenging, whereas now, you can work at home and the technology is there. Everybody is doing Zoom calls, the technology is there, the stigma from working from home is gone. I think we’re moving in a fantastic director with the changing definition, the changing way we work.

Like I said, for those with disabilities, minorities, women, all of those barriers to entry are now either gone or significantly lower for everybody. But like I said, I think it really benefits those with disabilities.

Kevin McShan: Dylan, I know that when you’re not working, you love to travel. So, my final question for you is, what have you been filling that gap with during the pandemic and what do you like to do for fun?

Dylan Ogline: Well, for fun I like to play hockey, like you said, travel, spend time with my girlfriend and my dogs. During the pandemic I have been out of the country in over a year. The end of last year I decided I wanted to see more of my own country, so I bought a motorhome and I was traveling around the country doing that. But, since the pandemic has hit, I’ve only taken two or three short trips in the United States. Obviously, that’s impacted everybody when it comes to travel. I’m really itching to get out there, but we’ve got to be safe and right now is not a safe time to travel, everybody’s got to wear a mask and whatnot.

Yeah, so right now, no that the pandemic’s going on, like I said, I hang out with my girlfriend, I can’t play hockey right now because the rink is closed still. Hanging out with my girlfriend, cycling around, do some hiking, anything we can do out in nature to kind of get out of the house, doing that. Trying to make due, but listen, it’s the definition of first world problems and there are certainly worse things that can be happening. I’m lucky that the worst part of the pandemic for me, is that I can’t travel. So it could be worse, could be much worse.

Kevin McShan: It could be. I want to thank you for your time this morning and allowing me to virtually travel to the Sunshine State again. I want to thank you for time and for being here this morning. I really enjoyed the conversation and want to thank you for your time this morning.

Dylan Ogline: Absolutely Kevin, thank you so much for having me.