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Dylan Ogline: “Things do not need to be perfect”

It’s ok to take an evening off. Or better yet a whole day. Contrary to the popular belief amongst those just starting their business, the world will not collapse if you get that extra hour of much needed sleep. The global economy will not come to a grinding halt if you take a breather. Oh […]

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It’s ok to take an evening off. Or better yet a whole day. Contrary to the popular belief amongst those just starting their business, the world will not collapse if you get that extra hour of much needed sleep. The global economy will not come to a grinding halt if you take a breather. Oh and best part? You will actually get better at what you are doing. Trust me and try it out.


As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Dylan Ogline.

Dylan Ogline is the founder of Ogline Digital, a digital marketing firm that provides direct response marketing solutions. Dylan believes that anybody can start and build their own digital agency, creating a life with more freedom, purpose and meaning. Dylan also offers training programs that are designed to take the guesswork out of building an agency and remove all of the unknowns that stop so many people from starting their own business, all in just six weeks. Visit him online on Facebook @dylanogline or on Instagram @dylanogline.


Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

Back when I was 15 or 16, I either read about it or somehow picked up the concept that digital marketing allows you to put services or products in the hands of people who don’t even know they are looking for them. It simply fascinated me. Also, marketing, done right, literally allows a business to purchase growth. It’s no longer an unknown where more sales can come from, you can basically just buy growth. That also blew me away.

Can you tell us a story about the hard times that you faced when you first started your journey?

It was hard getting over my fear of making people angry by saying “no”. I wanted to do everything for everybody, so I offered every service. I wanted to reply to every single email as fast as possible, so I was that annoying person with push notifications on my phone for email. I wanted to be available 24/7 to my team and customers, so I took calls on holidays or in the middle of the night. It took me a painfully long time to learn the power of saying “no”.

Where did you get the drive to continue even though things were so hard?

I’m from rural Pennsylvania and I come from a very blue collar, hard working, nobody-is-going-to-hand-it-to-you town. Work ethic was something that was taught to me at a young age. Nothing comes to you free, you have to work for everything.

My family was middle-class. So when I started my own business, it wasn’t because I wanted to have a Lamborghini and a few Rolexes. Those were not the things that drove me. What drove me was that I didn’t want to be poor. I didn’t want to worry about how I’m going to pay the water bill or the electric bill. I grew up in an older house with what felt like zero insulation. I remember freezing at night in the middle of winter because it was an old house. It was expensive to heat, and my parents, justifiably so, didn’t want to spend the money. All I cared about was heat!

So, how are things going today? How did grit and resilience lead to your eventual success?

As cliche as it sounds, I live my dream life. I never thought I would get here. But through all the long painful nights, and failing time and time again, things finally started to click. It’s very true that you simply can’t give up. Never give up. It may take you 5 years, or 10, or 50 but just keep going.

I now have a great business that is thriving more and more each year. I have an amazing team in place that allows me to have nearly total time freedom. I’m healthier and more well rested than ever. And before the pandemic, I could travel pretty much whenever I wanted for however long I wanted. So I guess things have gone downhill in that area but I’m certainly blessed that my biggest complaint is that I can’t travel outside the country right now.

Recently, I’ve been putting nearly all my focus into my training program. It’s far and away the most fulfilling work I have done. Oh and the best part? I can turn the heat on whenever I like!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I think it’s important to note that when you are actually in the middle of the mistake, it’s never funny. But luckily when you look back you can have a few laughs. For me this isn’t so much as funny but more like a face palm where I look at myself and think “how could I be so dumb”.

I signed up for this program that essentially taught you how to start a small Kindle publishing company. “Publishing company” is making it sound a lot more fancy than what it was. The basic premise was researching various Kindle categories looking for niche keywords and then hiring writers to throw together quick 2,000 word ebooks on those keywords. You got your covers designed and boom, you’ve got a Kindle ready ebook to sell. Then you can run ads to the books to drive them up in the rankings.

Well, I decided to test a few niches to see what would stick and what could get results. Publishing maybe five ebooks in five different categories. And the winning niche? The winner was Amish romance stories. I ran with it. I spent the next 6 months and about $30k hiring several authors on Upwork and publishing nearly 200 Amish romance stories on Kindle and pushing ads to them.

As you can likely guess, it didn’t exactly take off. Although I did eventually make my money back and at least break even. I am proud to say though that for at least a short period of time I was undoubtedly the #1 Amish romance publisher on Kindle.

The lesson there for me was to not focus on low margin businesses. Plus, if you are learning from someone, realize that you likely won’t be the best of the best. The program was taught by this guy who was making 5–6k/month. That was my goal but he was the best of the best. The odds are you won’t be the best but you can very likely be average. So in that industry by being average you end up making $500/month. I learned that if I wanted to make $5–10k/month I should aim for something where the best are making $50–100k/month. So if I end up being average I can still hit my goal.

What do you think makes your company stand out? Can you share a story?

My agency is not full service. We do have customers come to us and they ask if we can do other things for them. Nope. We only do digital marketing management. This allows us to be extremely good at what we are doing. We don’t do everything for everybody. We only do one thing for a few select verticals.

As far as my training program goes, I teach something that I actually did and that I am actively still doing. I’m not teaching theory. I’m teaching how to step-by-step build an agency, just like the one I currently own and run.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

The marketing industry is at its core, a creative field. I’ve never seen anyone be truly creative and write great copy or design an amazing ad when they were exhausted. By taking care of yourself; physically mentally and emotionally — you will become much better at what you do.

Drink some water. Get a good amount of sleep. Mediate a bit. Go for a walk. Spend time with friends and family. These things don’t make you weak. They make you way better at what you do best.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

This is a great question. I completely agree. Nobody is self made, we all have help. I’ve been so lucky to have incredible teachers and mentors along the way as well as amazing authors and books I happened to stumble upon.

I’ll mention two that stick out. Tim Ferriss and the 4-Hour Workweek had a massive impact on my life. His teaching that you should focus on the 80/20 most important things was huge for me. Not to mention inspiring me to focus on both financial freedom AND time freedom.

Another is Sam Ovens. He taught me the system and tools to build a consulting business that has allowed me to focus on my passion for mentoring new entrepreneurs.

How have you used your success to bring goodness to the world?

I’ve always had a passion for coaching others. So I would say I hope to bring goodness to the world through mentoring new entrepreneurs. That’s now my #1 focus.

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

In no particular order, my wishlist would be:

  1. Things do not need to be perfect. It’s actually better for them to not be perfect. Time is what matters more than anything. So try things in rapid fire. The only way to figure out what will work is to try them. Launch that new product. Offer that new service. Try that new ad. Until you figure out something that actually works, try and try fast.
  2. Figure out product market fit as quickly as possible. You cannot create a desire or need in the marketplace, you can only tap in to what already exists. The fastest way to figure this out is to see if your ideal client is willing to pay for it. They may tell you they want it but until they actually pay you for it, you can’t know for sure. The easy solution is to start selling your product or service before you even have it built.
  3. Focus on high profit margin businesses. Don’t waste your time building a business that is really tough to make a good profit in. If your goal is $100k a year, don’t get into a business model where the best make $100k. Get into a business where the best make $1M. So if you end up being just sort of good, but not the best, you still can hit your goal.
  4. Say no. The only way to do more is to do less. You cannot be the best at everything. You can not do everything for everybody. This WILL make people mad. They will get angry with you. But if you want to be the best at anything, you will need to start by being the best at one thing.
  5. It’s ok to take an evening off. Or better yet a whole day. Contrary to the popular belief amongst those just starting their business, the world will not collapse if you get that extra hour of much needed sleep. The global economy will not come to a grinding halt if you take a breather. Oh and best part? You will actually get better at what you are doing. Trust me and try it out.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I believe that the meaning of life is to take your “luck” and push it as far as you possibly can, then figure out how to spread that luck around as much as you can. Maybe you can only impact one person. Maybe you can impact billions. Maybe you donate money. Maybe you fund a school. Maybe you become a teacher. Maybe you write a book. The whole giving back thing IS the meaning of life.

I look at my life and I understand just how ridiculously lucky I am. Sure I have worked hard and maybe I have a small amount of natural talent here and there. But I am lucky. Or blessed. Whatever you want to call it. For all the million things that went wrong, I consider it chance that I learned the lessons I did along the way so I could make a few things go right. That I happened upon certain mentors or teachers. That I picked up certain books along the way. That was all luck.

So the movement I would want to inspire is for people to have a bit more gratitude for the things they have in their life. Don’t feel so self-important and realize you aren’t self-made. Hopefully it would inspire them to make the lives of others better in whatever way they possibly can.

How can our readers follow you on social media?

They connect with me on Instagram @DylanOgline, Facebook @DylanOgline, and LinkedIn @DylanOgline

This was very inspiring. Thank you so much for joining us!

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