ANY business can be a “Lifestyle Business.” Here’s how …

Survive and Thrive

January 6, 2021

“The cost doesn’t necessarily matter—time matters more, results matter more, quality matters more.” In this episode of Survive and Thrive, John Meese declares 2021 the “Year of Harvest.” I guess that means we will reap what we sowed in 2020? I’m not sure, but I like it.

We also talk about Parkinson’s Law—work expands to fill the time you give it. If you don’t take charge of your time, others will take charge of it for you. People often scoff at the idea of a “lifestyle business,” but ultimately, all businesses—all work, even—are about the lifestyle that it affords. Don’t like your lifestyle? Change how you do business. It won’t change for you, but I have yet to find a niche where it isn’t possible.

We also discuss...

  • How to know if your prices are too low, and how to go about raising them.
  • How niching down allows you to command higher prices.
  • What first motivated me to go into business.
  • Why more and more people will become business owners—whether they like it or not.

About the Show: John Meese is the host of Survive and Thrive.

Full Transcript

John Meese: You are listening to Survive and Thrive. I’m your host, John Meese, and I want to help you navigate the path towards building a thriving business in any economy, including this one. With that in mind, I’ve asked some of the best and brightest minds in business to share their experience and insight with me, and with you. Without further ado, let’s dive right into today’s interview. Dylan, thank you so much for joining me today. How are you?

Dylan Ogline: I’m doing good, John, how about yourself?

John Meese: Well, I’m doing good. It’s a new year. I’ve actually declared this year, I use Notion, I have like a personal dashboard, when I login it’s like my goals and everything like that. And the first year I’ve gone full woo-woo, I put at the top, “2021, the year of harvest.” So I’ve just kind of put it out there.

Dylan Ogline: That’s good. I like that.

John Meese: Yeah. Yeah. So that’s for the year.

Dylan Ogline: Especially after the dumpster fire we just went through.

John Meese: Yeah, 2020 was definitely a year of a lot of other things. I haven’t actually determined what to call that one yet, so I’m just saying this is the year of harvest. We don’t need to talk about 2020.

Dylan Ogline: Yeah, let’s just forget that that happened, so, yeah.

John Meese: But let’s move forward. So, Dylan, like I said thank you so much for joining me today and I’m looking forward to digging in to learning more about your story and what insights we could take from this to share with other entrepreneurs. But before we do, I’d love to give you a moment just to share with us, Dylan, who are you and what gets you out of the bed in the morning?

Dylan Ogline: What gets me out of the bed in the morning. So, man, now it is I’ve reached a point in my career, which I’m only 31. So saying that word still makes me feel very uncomfortable. But I’ve been owning my own business for 17 years now, give or take? So but I’ve reached the point where I’ve kind of hit financial goals. And that probably really happened probably like two years ago, and I’ve been making this transition now to more of giving back. Which sounds so clichéd, and I hate saying that term too.

John Meese: I was going to say, do you have like a “live, laugh, love” poster over there somewhere?

Dylan Ogline: Yeah, it’s over there on the wall, absolutely. No, but it’s been exciting. So my main business is a digital marketing agency, and that, I mean it’s great, highly profitable, fantastic business. I love working with my clients. I love that business. But it gets to the certain point where helping somebody go from $500,000 a year in sales to a million a year in sales, like that’s awesome. That’s not changing somebody’s life. In the last, probably two years, I’ve been putting a lot of my focus into training and education. And working with people who are on the ground floor like they had a job, maybe they lost their job. Maybe they started their business and they’re doing say, $2,000 a month. Getting that person from $2,000 to say $8,000 changes everything.

John Meese: Dramatically.

Dylan Ogline: Exactly. So what’s been getting me out of bed is, as clichéd as it is, helping people. A drastic change for me over the past couple years, absolutely.

John Meese: Well, that’s good. Well, you passed the test. Well let’s talk a little bit about that. Because so you mentioned that you’re 31 and you’ve owned your own business for 17 years, which if my math is correct, that means you started this business in some form or fashion when you were just 14. Is that right?

Dylan Ogline: Not the business that I have now.

John Meese: Right.

Dylan Ogline: I started my very first business when I was 14 on, oddly, a wholesale cellphone business. Flipping them on eBay back when I was 14.

John Meese: Wow.

Dylan Ogline: And then between then and so now it’s a digital marketing agency. I really didn’t make that shift to that product or that service, excuse me, until like the end of 2016. So there was 12 years of bouncing around between all sorts of different things.

John Meese: So what initially drew you to entrepreneurship as a career? To use the word you used earlier.

Dylan Ogline: I was surrounded by business owners. My parents were business owners. At the time in my life, my girlfriend at the time, her dad was the president CEO of like the biggest business in the area. So I was highly influenced by him, he was a mentor for a very long time. I picked up Rich Dad Poor Dad by Robert Kiyosaki. All these things happen when I was like 13, 14 and I was starting to think about like well, what do I want to go to college for? And business kept popping up. I ended up not going to college, but it was yeah, just all these things hitting me at the right time, and that kind of lit the spark.

And in plain English, I didn’t want to be poor. I grew up in a middle income family and-- I've talked about this before-- literally my motivation was I wanted to be able to turn the heat on whenever I wanted. I didn’t want to freeze.

John Meese: Whenever you wanted. And you could pick the temperature, right? Not have to worry about it going above that dreaded-- every family that I know in the middle or lower class, I mean again, I grew up in a relatively poor family. It’s hard because like we live in this like first world country where it’s like yes, even if we’re poor or rich, okay great, like let’s set that aside for a second. Still, we were at the point, I remember there was like a degree where you were not to turn it above a certain level because you’d hear something about the heat bill for sure.

Dylan Ogline: Absolutely. Yeah. Yes, I grew up in Western Pennsylvania, so brutal winter, and just absolutely froze. That was what my motivation was. Wasn’t to buy some fancy car, or have some fancy watch, it was I just wanted to turn the heat on whenever I wanted.

John Meese: Well, do you have the heat on right now?

Dylan Ogline: Actually, the AC’s on, I’m in Florida so.

John Meese: Oh, okay.

Dylan Ogline: It’s a little different now.

John Meese: It’s a little different. Different problem. Yeah. Well, great, well thank you for sharing that. So I know you didn’t start with digital marketing, but now you’ve been leading a digital marketing agency for some time now. So what does that look like? Can you give us an inside look into kind of what your company and your services look like currently?

Dylan Ogline: Sure. So the business is called Ogline Digital. And we, just in plain English, our tagline would be that we offer direct response digital marketing management services. But to everybody else, it’s we simply manage our clients’ Google and Facebook ads, and sometimes YouTube. That’s all we’re doing. Which we only have a few clients, ranges depending on the seasons and whatnot, but typically under seven clients. We write the Facebook ad, as an example. We choose the pictures, we choose the targeting, things like that. I have systems in place for all that stuff, and then we drive the leads towards typically some kind of form or something on the client’s landing page. That’s basically what we do.

John Meese: Okay. Great. And that supports your lifestyle. I mean, is that your primary business the core focus of what you do then?

Dylan Ogline: Absolutely. So The 4-Hour Work Week by Tim Ferris was a huge impact on my life. So my goal when building the agency, it was really all about lifestyle for me. So I work at home, I do have a co-working membership, but especially with COVID I’m not using that.

John Meese: Hey, hey, I own a co-working space. So I’m like whoa, whoa, whoa.

Dylan Ogline: Oh really?

John Meese: Yeah, you need it, desperately, right?

Dylan Ogline: No, I still have the membership, and 100% yeah. Well, I go sometimes.

John Meese: No, I understand, I’ve seen it.

Dylan Ogline: Yeah. Yeah. So yeah, I built the company with lifestyle in mind. It wasn’t just let’s just generate revenue, it was I wanted to create it in a certain way. So I’ve never met any of my team members in person. They’re all throughout the world. A lot of them I never even talk to. I couldn’t even tell you all their names because I honestly forget them because I talk to them so rarely. That’s all by design. I designed the business in that way. And we really took a long time to get there.

John Meese: Sure.

Dylan Ogline: But it was by design.

John Meese: Well, let’s talk about that. I mean, let’s assume that there’s people listening right now to this interview who are thinking, “Man, well that sounds nice. Way to go Dylan. How do I get some of that?” And so maybe let’s talk about that for a minute in terms of how you navigated that path. And it’s 2021, it’s a new year and I think there’s a lot of entrepreneurs who are thinking the term lifestyle business has been used kind of pejoratively to describe kind of cuckoo side projects that people have.

But the reality is that everyone’s in business and everyone’s in work for a lifestyle. Now it may be that your lifestyle is that you want to build some multi-billion dollar company and you want to then sell that for boo koos of money and go hang out on an island. And maybe that you want to automate your business, see how the cash flow machine. It may be that you just want to break free from your day job and you want to be your own boss, or that you want to work directly with a handful of clients. Whatever that is, lifestyle’s at the core of business, I mean it’s like it’s the core of work, period.

So with that in mind, I’d love to know just thinking about the people listening to this right now who are perhaps a little jealous, let’s just acknowledge that emotion of what you’re experiencing, Dylan. What would you share or encourage people to prioritize to pursue the lifestyle that they wanted through their business?

Dylan Ogline: Sure. And I liked how you talked about even if you’re a contractor working for a couple different people, you don’t have any team members, it’s all you. You’re a business owner. If you’re, say, a graphic’s designer and working for five different companies, or you’re a writer and you’re working for five different companies, you’re a business owner and you need to realize that, you need to think of that. And I would argue that, especially with COVID, we prior to COVID the definition of work has been changing. So more and more people are less likely to be employees and more likely to be kind of contractors and it’s been making that shift.

And so for first is recognizing that you are a business owner whether you like it or not or whether you consider yourself to be one or not. And the second is if you are having that feeling of jealousy or something like that, realize that you set the rules for your business. So if you’re sitting there, you’re like, “Oh, I want to be able to post-COVID travel around the world.” Like travel was a huge important part of my life, so I built my business in such a way that I could travel. So I’ve traveled all over the world while running my business. If that’s something where you’re sitting there and you’re like, “Oh, I’m jealous of that, I want that kind of lifestyle,” you need to realize that it’s your responsibility to build your business-- again, whether or not you think you have a business or not-- it is your responsibility to build your business in such a way that gives you the lifestyle that you want.

And if you’re sitting there thinking, “Oh it can’t be done.” I have yet to meet anybody that was like, “Nope, it’s not possible with your particular business.” There’s a lot of people who need to make shifts, make changes, but it can be done with absolutely anything and you just need to put in the work and decide what kind of lifestyle that you want. And I would argue that is the most important thing. And where you went with it where maybe you want a billion dollar business. If that’s truly what you want, then build that. But if you want some kind of cash flow thing that allows you to quit your day job, then build that, and build it on purpose that way. Just being conscious of it is I think the most important thing.

John Meese: Yeah, no, I think that’s powerful. And it’s so much of life work, entrepreneurship, business, all those things. It’s easy to fall under the trap of just kind of reacting to what’s there, maybe you have a job that turns into a contract and you’re like, “Oh, all of a sudden I’m a contractor. Okay. I guess I’m a freelancer now.” Maybe you take on one other client. Like it’s easy to kind of just go with the flow. There is a way to build a business of some kind, but it’s going with the flow. But if you’re not careful, you could end up building the business that you didn’t want in the first place. And so I think it’s so important, as you just described it Dylan, of just getting clear on where you’re going with this, I mean what’s the goal here? What’s the end game?

Dylan Ogline: There is an incredible book. I don’t know who the author is. There’s a book called Essentialism by whoever.

John Meese: Yeah, by Greg McKeown. Yeah, yeah.

Dylan Ogline: Yeah, incredible, incredible book. If you haven’t read it, go buy it now.

John Meese: I second that. I agree with that. Yeah.

Dylan Ogline: It’s been a while since I’ve read it, but he talks about how I think specifically with time where like if you don’t decide how your time is set up, or what projects, or what you were working on, other people will decide. So if you’re sitting there and you’re like, “It’s not possible for me. I can’t build my business this way. I can’t do things this way.” It’s because you gave up the ability to make those decisions. Somebody is making the decision and you just need to restructure things so that you have the ability to make the decision. And most importantly, when you get that ability, actually make the decision to focus on what you want and the lifestyle that you want. It’s up to you.

John Meese: Hey there, it’s me, John. Just talking to you. I know that you are a busy entrepreneur with an endless to-do list. You don’t need another tactic or another gimmick to try. You need focus and you need results. You are not content to just survive with your business. You want to thrive and I want the same thing for you. That is why I have created a complementary business assessment that gives you a numerical score for how well your business is currently doing based on the fundamental ingredients to long term business success.

Once you know your score, you can hyper focus your tactical efforts on improving your marketing, sales, or financial systems so you can watch your score and your bank account grow. Visit to claim your free assessment today.

Yeah, no, I think that’s a really powerful concept, and that book by the way, one of my core values is do less better, which comes straight from Essentialism. So you picked a good reference for sure. But within Essentialism, Greg McKeown I think in that context talks about a couple things that you’re referring to. One of those is Parkinson’s Law, which states that work expanse to fill the time allotted for it. Which means that like if you set up, and you’re like, “All right, I’ve got to write a blog post or I’ve got to draft an instruction manual for some process that I’m going to delegate to somebody. I’m going to give myself 20 minutes.” Well, guess how long it’s going to take you to do it: 20 minutes. Give yourself 90 minutes, give yourself two hours, that’s how long it’s going to take.

Dylan Ogline: Taking 90 minutes.

John Meese: It’s going to take 90 minutes, it’s going to take two hours. And that’s Parkinson’s Law, which is that work expanse to fill the time allotted for it. And the second thing, a concept that I think is powerful that you shared, is jut that someone is making a decision about your time. Now the question is, is it you, or is it someone else? And one of the most egregious offenders on that level, I would say, is email. So many people check their email first thing in the morning.

Dylan Ogline: And nonstop.

John Meese: And nonstop, that’s true. And what email is, is email is an open door. Anyone can request anything of you. And if you let your email in-flow direct your workflow, well then you’re just going to be prioritizing other people’s priorities the whole time.

Dylan Ogline: And you’re also reactive.

John Meese: Yes.

Dylan Ogline: You want to be proactive with your work to the best of your ability. And there are certain things that fires that can pop up that you need to put out to a certain degree. But a lot of that stuff is just setting rules, and with those fires, if you can write a manual or something like you mentioned so that people you have in place can manage things-- if this then this, if this happens, do this-- I mean those are just like simple ideas right there. But the people that I talk to the biggest thing is they just simply need to recognize that this is my responsibility and I have the choice. That is the most critical thing.

Like email, personally, this is just a simple rule that comes off the top of my head. If somebody emails me something, it’s not getting responded to for at least 24 hours. Even if I’m in the middle of answering all my emails right now, something comes in, I will purposely snooze it until tomorrow. I have just like some Gmail that I don’t know if it’s an add-on or something in Gmail, but I’ll just snooze it until tomorrow. And I do this so that it trains other people to not think, “Oh, I can email Dylan, he’s going to email me right back.”

If they are doing that all the time, then the next thing they’re going to be calling you and being like, “Hey, Dylan, I didn’t hear from you. What’s going on? Is everything okay because you didn’t get back to me within 15 minutes.” If that’s happening to you, I’d hate to tell you, but it’s your fault.

John Meese: Yeah. You can set expectations. And people always come with their own preconceived expectations. Like I had a client recently who this didn’t come up in our internal conversations before we started working together, but then it became clear right away. They have an ASAP culture. Where everything is like literally like a meeting would just appear on your calendar in 15 minutes. Like they didn’t send you a message, they were like, “We’re meeting,” and it would just appear in your calendar, and you’re like, “What?” No, I’ve got other things going on.”

So in that case, at first I got a little frustrated. But then I paused and I was like, “No, this is on me.” And so I came back and I drafted a little message in Slack to their team just to say, “Hey, I am so excited to be working together. And I just want to share a couple of suggestions on some of the ways that we can work together that’s going to maximize our time and our ability to focus on high leverage things.” And it was those kinds of things. It was like, “I’m going to protect some time each week for pop-up meetings on my calendar, which you’ll have shared, so you know like if you just need to book something quick, it could happen during those windows. Otherwise, please reach out to my assistant and she can coordinate a time.”

Like it was just me just communicating. And even when I sent that message, even though I know this, I’ve done this a hundred times, I still when I sent that message just like anybody else out there who’s cringing a little bit, is thinking like, “Oh, they’re going to get so mad though. They’re going to fire me. They’re going to lose the bid”

Dylan Ogline: They’re fired, yup.

John Meese: “I’m going to lose the gig, I’m going to lose the money.” But no, they just responded with a thumbs up emoji. And then like somebody else from the leadership team on that company like commented in the thread on Slack, and tagged other people, and was like, “Hey, make sure you listen to John on this.” We do have control. We do have influence. And with email, same, I’ve noticed that over because I, just like you, I built a habit that I don’t generally respond to something same day. What I do, because I know that my most productive hours are in the morning, is I don’t check my email until noon. And so I do actually have an assistant who will go in there, and she filters my inbox for me. So first of all, I don’t see anything until it goes through her. So 80% of my email, I don’t actually need to see it. It’s like a notification or…

Dylan Ogline: Meaningless stuff.

John Meese: It’s meaningless stuff, yeah, most of it. So she takes care of all that. And then around noon or shortly thereafter I check my inbox and I just see what I need to see. What’s already been filtered for me. But secondarily, just because of that built-in system, that means that most people are hearing back roughly 24 hours after they sent the email. Unless you send an email in the morning, and then it gets through the filter, that’s fine.

And so I don’t have like an autorespond on my email that says like, “By the way, I’m not going to respond right away.” But people in my life that I work with on a regular basis, they’ve picked up on it. And so I mean literally yesterday, I wouldn’t have seen it, but there was a church service yesterday evening, and I’m involved and volunteer at some things with my church. And so the choir director had sent an email, and then he sent me a text, right? He sent me a text.

Dylan Ogline: Because he probably knew. He’s like, “John’s not going to see this.”

John Meese: He knew! He knew I wouldn’t see it and so he sent me a text. He was like, “Hey, just want to make sure you get a chance, if you can, check the email I sent you before tonight that’d be helpful.” Great. Easy peasy. Done. In the past, I would always feel like I had to respond to everything all the time, and that created some issues. And so, obviously, email is getting me a little riled up. But Cal Newport is writing a book right now, it’s not out yet, but I’m very curious to read it. But he’s writing a book, I think it’s available for pre-order, called “A World Without Email.” And he’s reimagining work because so much of everything we do is based around the product.

Dylan Ogline: Around the email and stuff. One thing I would mention, for those who are cringing when we were talking about setting these rules and thinking, “Oh, that client might fire me.” I think this all plays into that whole making the shift with the changing definition of work where more and more people are going to be business owners-- whether they like it or not-- they're going to have multiple companies or organizations that they work with.

So when you’re thinking, “This person might fire me.” Realize that that’s not the end of the world. And I like to say that I fire bad clients. They don’t fire me, I fire them. And at the end of the day, when you make this shift, what you’ll start to see is like those clients that are like demanding your attention or sending you pop-up meetings that are in 15 minutes, they’re probably impacting your quality of work.

John Meese: Definitely. Definitely.

Dylan Ogline: Especially if you have some kind of creative work. Like for us, we’re writing ads, or something like that. Or if you’re a writer, I mean hands down, this is something that impacts you. If you fire these bad clients, contrary to popular belief, it might actually make you better at what you’re doing so that then you can charge more and your clients get better results. So just realize it’s not the end of the world, and it’s actually probably a good thing. It’s all about quality and you need to make that mindset shift where recognizing that these are good things. And you will have the pain clients who are like, “Oh, no, that’s unacceptable. You need to be available 24/7.” Like whatever, dude, get out of here. I’m not wasting my time. The world does not revolve around you. And I can’t deliver good quality work if you’re interrupting me every 15 minutes.

John Meese: Right. Well, let’s talk about that. Because you mentioned one of the byproducts of setting those boundaries is your ability to raise your rates. And I know that’s somewhere, again, we’re talking about cringing, that’s somewhere where I know a lot of people get stuck. And myself included, I mean I’ve read all the books, and gone through the training programs, and I know all about doubling, or tripling, or quadrupling your rates, or 10xing your rates. And still, I found because I’ve heard this from other people but I found this myself. Because I’ve 10xed my income over the past five years in my business.

And at each point, there seems to be an imaginary line I come to. It’s like my stupid number. Where you come to a point, and it’s like the biggest number you could ever imagine charging someone without feeling like a complete failure. And now I look at the number that I charge now, and I look back at what I charged two years ago, three years ago, and I just can’t believe it. But I know now I have my own stupid number that I can’t pass. Like my current roadblock and I will overcome it.

Dylan Ogline: Yeah.

John Meese: But I know that’s one of the things that you talk about is showing your value to be able to raise your prices. So can you provide any advice or tips about kind of what that looks like for someone in my position, for every entrepreneur? Whether they’re a business owner or selling a product that may be underpriced or a consultant selling a service that’s underpriced. How do you recommend approaching that?

Dylan Ogline: Sure. So really, it comes down to what is the problem that you’re solving? And all these things they play together. It’s like a snowball effect. They all feed off of each other. So one of the things I like to talk about is niching down your solution. Everybody talks about niching down. But I’m like take it even further. So if you’re like, “Oh, I’m going to target this particular industry.” Like go even further, like as far a niche as you possibly can, and try to solve as niched of a problem as you possibly can. And the more niched down the problem is, the better you are going to be at solving it, and then you can get better at defining the problem.

And whenever you can define the problem better than the person who has the person can themselves, they will automatically assume that you have the solution. I mean that’s just marketing. But when you start to do that, it feeds off of itself where the client will start to see the value not necessarily your time. Again, this is so broad. Let me just ask, what is your business? What do you do? Because I could probably define it better for folks if I can give an example, other than myself. I can give a great example with myself, but what’s your business, let me ask you that.

John Meese: Yeah, so my business specifically?

Dylan Ogline: Yes. The one where you 10xed your price you said.

John Meese: Well, so yes, I have three businesses, which is part of my own neurotic problem that I created for myself. But one of those businesses through-- I'm trying to think which one would be better to focus on. But like Notable Themes is a great example that I loved to focus on, actually. So with Notable Themes it’s actually a software company. And we sell, in the past it’s like WordPress themes and plug-ins. But we’re really hyperfocused now on this flagship product we’re rolling out called Notable Press. And it is technically a WordPress theme, but it is essentially like a website builder for creators to publish your blog, podcast and YouTube content on a website that has a dynamic homepage, that kind of feels more engaging than like a static homepage kind of like the reason why we refresh-- well, I don’t-- but the reason why people refresh their Facebook feed over and over again is because it’s like fresh and exciting. And so being able to take that kind of energy to your website.

So we sell the software itself, we also have a productize service that goes with that that we sell now, called Notable Prestige. Where we’ll work with you, my business partner and I, he’s the designer and the developer, and I’m the marketing guy. And so we’ll help you create a personalized marketing playbook combined with like a brand and logo kind of like brand identity playbook. And combine that with actually building out your website on Notable Press.

So that’s a new service. We just launched that and I know we’re underpricing it right now, but Notable Prestige includes the personalized marketing playbook, it includes your brand identity-- you get your brand identity kit-- and it also includes your website built out on Notable Press for you, and it’s $5,000. So that’s an example of like for that business, for Notable Themes, that’s the highest price listed service that we have other than kind of one-off customized projects.

Dylan Ogline: Did you say like if you have like a podcast or something you would use that? Who’s your ideal client?

John Meese: Content creators in a broad sense, but for this specific business, for this specific product category we’re focusing on content creators who have an established audience. The software itself beginners should use it, that’s awesome. But for this service, these are more like someone who’s already got a podcast, they’ve already got a YouTube channel, they may have a couple hundred thousand subscribers. And then what we’re showing them is you can actually take all of that content, build your own audience outside of YouTube, monetize that. I mean potentially we’re talking about if this is your first time building out your own content engine outside of a platform like YouTube, you may be adding $10,000, $20,000, $30,000, or $100,000 in revenue to your business right away. Depending on the size of your audience and how engaged they are.

Dylan Ogline: Gotcha. So this is actually a pretty good example.

John Meese: Great.

Dylan Ogline: Because content creators, so most people when they’re starting their business, they’re starting their service, they’re creating their product. They’re thinking content creators, they want to create some product or service that services everybody, okay? But recognize that there is only-- and this is repeatable in nearly every industry-- there's only a small percentage of the industry that is looking to really spend money on something. Like you want to look for where is the sweet spot of like high profitability there. And that might only be 5% of the market, 3% of the market, okay?

Whereas most people are thinking, “I want a service that 100% of the market is going to be interested in.” And the truth is, is that there is no service or product that 100% of the market wants. An example I’ve used before is like cars, okay? You could create a free car. Like literally a free vehicle that will sit out there, they deliver it for free. There is still a certain percentage of the market that has absolutely no interest in that. There is still a certain percentage of the market that is willing to spend $300,000, $400,000, $500,000 on a vehicle because they want absolute perfection. Or they want to be unique, or they want this, or that, okay? This is where you can get price trapped where you’re thinking, “Oh, the cheap solution.” Okay, well, I just gave you an example where even if you had a free vehicle, not everybody would want it.

John Meese: Right, well, can you think why they wouldn’t want it? Because I’m thinking of somebody as myself and I’m just curious what you would say.

Dylan Ogline: Why not everybody would want the free solution?

John Meese: Yeah. Like the car.

Dylan Ogline: Well, like the car, because there’s a certain percentage of the market that money isn’t a factor. It’s not the money. They have a problem that they want to solve or they want something. So their problem might be that they just want absolute perfection. They want the very best, okay? Or they want to be unique. That’s not necessarily a problem, but they want to be different, they want to stand out. So they’re willing to spend-- and again, money is not a factor-- they're willing to spend $400,000. They have a Ferrari because they want everybody to look at them.

John Meese: And if I could add another on the flip side, or maybe not the flip side but the other side of the spectrum, I’m thinking with the car example. A car might be free, but that doesn’t include gas, oil changes, maintenance, knowing how to drive, right? I mean there’s like on the other side of the spectrum there’s a lot of people who wouldn’t know what to do with a free car.

Dylan Ogline: Yeah. And it can go in many different directions. So like with the content creators. So I’m sure probably somebody could hack together all of these different services to get essentially what you’re offering, right? And maybe it’s a third of the cost. But to a certain percentage of the market, maybe 3%, maybe 5% of the market. The cost doesn’t necessarily matter. Time matters more. Or results matter more. Or quality matters more. And they’re willing to spend the money to get the highest quality or the time matters more. And realizing whatever your unique selling point is, the more unique it gets, the higher you can charge a price for.

So it can be quality, it can be time, it can be uniqueness. Those are just three categories that come to mind. And the better you get with that, the more niched down you can get, the faster your service, or the more unique your service, or the higher quality of your service, the higher you can raise your rates. Did that answer the question?

John Meese: Yeah.

Dylan Ogline: It took a lot longer than I expected, but I think that summarizes it.

John Meese: No, I think that’s good, that’s helpful. I’m just trying to think I want to make sure we’re sharing this in such a way that’s helpful to the audience. So I’m just trying to think in their shoes. How do you raise your prices? In other words, do you have like a gut check, or a framework, or some advice on do you raise your prices 10% at a time, 50% at a time, do you double them? I mean how do you tell when you’re overpricing something? Is it kind of the flip side of that? How do you know when you’re overvaluing your services?

Dylan Ogline: So I think taking an analytical approach to it can get very complicated. That’s almost like big business approach. Really analyzing the market and trying to figure out, that’s like airlines trying to squeeze the little bit more in pricing, right? Whereas the truth is for most business owners, most entrepreneurs, if you’re a writer-- let's use that as an example again-- say you’re writing for five different companies. Once you reach capacity, you are working 40 hours a week writing. Just raise your rates until that capacity starts to go down a little bit.

So it might be double your rates. And you kind of have to judge the market. So it might be doubling your prices. It might be 5xing your prices. Which is more difficult if you’re doing that with existing clients.

John Meese: Oh for sure. Sure. With existing clients it’s very difficult.

Dylan Ogline: Yeah, it’s a lot harder.

John Meese: Almost impossible. Not quite, but yeah.

Dylan Ogline: Yeah. But with my current business, we charge a 10% of whatever the client’s ad spend is. So there really isn’t any. Because the more they see they spend. But before I’ve done like web design and stuff like that before. I would just go to people and be like, “Hey, starting January 1st, our rates are going to $50 an hour, whatever. We’re going to honor any projects that have already started or whatever, we’re going to respect that. If this works for you, please let us know. If it doesn’t work for you, just let us know, and we got some maybe referrals, and we can pass you as a client on to other people.”

I mean most people respect that. Again, it is a lot more uncomfortable rather than just bringing on new clients and being like, “Hey, now we charge $100 an hour.” We realize it can be done, it absolutely can be done with existing clients.

John Meese: Those are great examples. Yeah. Well good, that’s helpful. Well, Dylan, I appreciate your time and I thank you for sharing your experience and your story with us today. I appreciated that. I know it’s going to be helpful, so where we can go to learn more about you and what you’re up to on the worldwide web?

Dylan Ogline: Sure. My website’s simply You can also find me on the Facebooks and the Instagrams, et cetera. Just @dylanogline.

John Meese: Great. Perfect. All right, thank you, Dylan. Keep up the good work.

Dylan Ogline: Absolutely. Thanks, man.

John Meese: Thank you for taking the time to invest in yourself by listening to this interview. Please subscribe to be notified about future episodes, and you can find more about today’s guest and the resources we discussed, at Did you know that I wrote a book based on the insights from these interviews? It’s true. You can learn more and get a copy for yourself by visiting I’m John Meese on a mission to eradicate generational poverty and I fully believe that entrepreneurs like you are the key to that success. Keep up the good work.