After Multiple Failures, I Now Run A $1.2M/Year Digital Agency

Published: April 7th, 2022
Dylan Ogline
Founder, Ogline Digital
Ogline Digital
from Orlando, FL, USA
started January 2017
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Hello! Who are you and what business did you start?

Hey! My name is Dylan Ogline and I am the founder of Ogline Digital. I run a digital marketing agency that is focused on helping companies scale and grow with proven direct response marketing strategies.

We are not a full-service agency. We only offer one service, digital marketing management.

We typically work with small to medium size businesses doing $100k to $5mil in annual revenue. Our clients come to us wanting to scale and grow rapidly and we help them get a system in place (and manage that system) so they can buy the growth that they want.

In a nutshell, we manage a marketing system for our clients that allows them to profitably buy customers.

The company was born out of many previous failures. When I was a teenager I started doing web design, mostly on the side. I continued to do this in my early 20s to just make ends meet from time to time.

Eventually, a handful of clients started to ask about Facebook and Google ads. I offered it to them but just like the web design, mostly as a side thing for extra cash. I was way too focused on all these other useless business projects that never went anywhere.

After bouncing around from one failed idea to another I eventually focused on just one service, digital marketing management. I don’t even say one business because it wasn’t even called Ogline Digital at the time!

I was so committed to keeping things lean and scrappy that it was just this service by me as a freelancer. Within a few months, I was on pace for 6 figures in a year (an insurmountable amount at the time). A year or two after that our annual revenue was over $1million off 10 or so clients. This year we finally passed 20 clients.

Apart from this, I also own Agency 2.0, an education program where I teach how to start and grow a hyper profitable lean digital marketing agency. But my main focus since last year has been on Ogline Digital. Its continued growth has required my near full attention.



What's your backstory and how did you come up with the idea?

I was born and raised in Somerset, a small farming town in rural Pennsylvania. Growing up, I hated it. There are so few opportunities, it’s very economically depressing. And everyone seemed very discouraging.

Looking back now I am so thankful and feel deeply blessed to have been raised there. Sure, there were many negatives but the people are just good. The type that would give you the shirt off their backs, that taught me to give back and to truly care about people. Also, the hardest working people you will meet hands down, so I credit my work ethic with where I am from as well.

Myself, my brother, and father are all high school dropouts. Education wasn’t much of a priority in my family. Now, I love to learn and I’m always taking classes and courses. I’m also an avid reader. No clue where I got those traits from!

Growing up I loved playing hockey. I knew I was far from Wayne Gretzky but I ended up having incredible coaches in the process who made a huge impact on my life. My goal for a while was to someday be a college hockey coach.

However, I started to realize that the odds were stacked against me. I was 14 or so at the time and I came to see that all the many players (very much) better than me all seemed to have started at a younger age.

My first real business mentor was my high school girlfriend's father. I quickly latched on to him and became incredibly close. Influenced by him and some books I happened upon, I decided that my best chance to do anything in my life was to get an early start in business just like the players who got an early start playing hockey.

I had no clue what this would look like but I just knew the general direction. I ended up dropping out of school in 10th grade to focus on my first endeavor, selling the early “smart” phones on eBay that I imported from Europe.

Fast forward a decade or so and I was nowhere but down. Nearly a $1mil in debt and numerous worthless business projects I was working 100 hours a week on. I ended up on a call with a long-term mentor who essentially told me to scrap the non-essential and focus on the highest profit margin opportunity. That ended up being digital marketing management.

The biggest challenge for me was resisting the temptation to try and make things perfect. I had to push myself to just go out and get clients even though the service wasn’t perfect.

At the time, I had offered the service as a freelancer for a few clients and kept that mostly unchanged, very scrappy, and simple. I focused as much as I possibly could on that one thing and within just a few months I was at 6 figures. A year or two later and it was 7 figures. Eventually, it became a little bit more organized and professional than Ogline Digital.

Take us through the process of designing, prototyping, and manufacturing your first product.

I started digital marketing when I was 14 or so driving traffic to my listings on eBay. At the very beginning of Google Ads. Back when you could get clicks for a couple of cents each! Facebook ads weren't even a thing yet. I was fascinated by it but didn’t truly realize how powerful it could be.

During the decade in my early 20s and late teens, I failed at one thing after another. Web design and agency work was something I did to help pay the bills.

Eventually, clients started to ask if we did Facebook or Google ads. “Well of course we do!” was the only proper answer.

I’m a perfectionist by nature so when I decided to cut everything and just focus on one main business I was tempted to build a full-scale agency. But by the urging of my mentor, I kept things ridiculously simple. Lean, mean, and scrappy I like to say.

Even now, I try to ruthlessly cut things and just focus on the most important thing that would help our clients grow. No fancy new platforms. No new-age tools. Just being world-class at one thing.

Describe the process of launching the business.

The biggest challenge for me was resisting the temptation to try and make things perfect. Given my numerous failures in the past, I had to push myself to just go out and get clients even though the service wasn’t perfect (it still isn’t and never will be!).

Do NOT spend months or years building your product or service only to find out that nobody wants it

I was at a point though where I was definitely between a rock and a hard place. There’s this saying I always remind myself of… “it comes down to if you are comfortable where you are at, or ready to make a change”.

I was very uncomfortable, to say the least so I just went all in. A simple landing page. One service. No logo. There wasn’t even the Ogline Digital name yet. Lean and very scrappy.

The first step was simply reaching out to all previous clients that I had worked with. I think that landed me 2-3 very quickly and it gave me enough cash to try two more things, Google ads and lumpy direct mail.

I kept things ultra-targeted toward businesses I knew I could help (those interested in lead generation). Google turned out to be the winner and to this day it’s mostly what we use to get clients, I’m just a lot more selective now on who to accept!

Within a few months I was on pace for 6-figures and within about 2 years was on pace for 7-figures.

Since launch, what has worked to attract and retain customers?

Well, as a digital marketing agency, we wouldn’t be good at our service if we didn’t have this dialed in ourselves.

This is a very simple part of our business. Most clients come from Google Ads. We use Facebook for retargeting and also a very little amount of cold outreach as Google is so effective.

Retention hasn’t been a problem due to the nature of our business. Clients view us as a partner in their growth. We manage their ability to scale. We remove the question of how they can get more customers by putting in place a profitable marketing system. They just have to manage the delivery of their product or service.

All billing is month-to-month but thankfully, our relationships have mostly been long-term.

Last year we also added Upwork to the mix. This was actually to test out some strategies for my program Agency 2.0 as many students worry about spending on any kind of paid strategy, especially in the beginning. While Upwork does have a small cost to it, it’s much less than Google or Facebook.

How are you doing today and what does the future look like?

Things are running like a well-oiled machine right now. Our team is up to 12 now. I try to keep even that ultra simple. I’m trying to build the system so there are silos of roles. Account managers (a client’s main contact) who work with a designer, copywriter, and media buyer. That’s it. No fancy titles or management structure. It’s all about being able to scale fast and remove complexity.

I’m happy, the team is happy, customers are happy and things are growing.

It’s tough to say where the future is going to go. I have a lot of ideas but given my past mistakes, I’m careful not to go in too many directions.

If I had to say for the next 5 years I would like to grow to $5-10million in annual revenue but do it in such a way that it’s more about my team than me. Right now, we are lean and very profitable, but I still feel sometimes like it's just a dialed-in freelance operation, I even have one client that pays to my personal PayPal just because I’ve been too lazy to convert them to Stripe!

I teach my students to build a lean, mean and scrappy operation that’s focused on delivering incredible results. That’s what I did with Ogline Digital, but I think it’s reached the point where I need to take things up a notch.

Not for me but the team. Full-time salary with benefits. Maybe employee-shareholders. Equity partnerships with clients so there is something big being built.

I think it's time to give back to the people that have helped me build the company and take it to where it stands now: a success.

I look at a lot of businesses today and they just feel like they are there to only make money. Of course, a business has to make money. Without it, your company will eventually cease to exist. But I hear stories from those older than me about companies they worked for and how they worked at the same job for 30 years.

That just sounds insane today! Maybe it has something to do with the culture though. People are just viewed as equipment these days, at best assets but not as actual people. When the truth is that the people ARE the business. I’m getting almost philosophical here but I guess for me I think about building a company and culture and environment that it’s not just a job where you make good money but it also makes your life better.

Through starting the business, have you learned anything particularly helpful or advantageous?

I have failed so many times, way more than I have succeeded. But looking back, the sad truth is there were a lot of projects/businesses that I worked on that just never got anywhere. This was mostly because I was so focused on being perfect. Everything had to be just right before I could ever launch or approach potential customers.

I mentioned before that I got the advice to focus on something that was a high margin. I believe something that goes together with “high margin” is being the best or only solution in the marketplace.

You have three options in business:

1) be the first - this is tough as there is such a thing as being too early.

2) be the cheapest - this is just dumb, It’s a race to the bottom.

3) be the best or the only - customers love you, are glad to pay a lot and you end up happier… aim here.

Lastly, you don’t need to know everything to go somewhere, just the general direction.

What matters more than anything is moving, fast.

Another critical thing is mentorship. Most people think of mentorship as someone much older but it doesn’t have to be that way. Simply being able to talk to those who are ahead of you, either in your industry or just business overall. In my case, I have tried to associate with other agency owners that are 10, 15, or even 100X more successful than me. This changes your perspective so that success almost feels like an expectation rather than an unlikely event. If I run into a problem it can feel like it’s impossible, but if I can point to 3 or 4 other people who have beaten that problem it changes my mindset to know that it’s possible.

In my experience almost every good business leader is willing to be a mentor, even on a small scale. So if you meet someone or read about someone who is ahead of you, ask them to coffee and just say they inspire you and you have some questions. Or just ask if they would be willing to jump on a call. Be open and transparent, a good leader will respect someone who is humble and asks for help.

What platform/tools do you use for your business?

This is going to bring out the fanboy in me.

These are in no order:

  • For sending quick videos, Loom. This is priceless. You can bust out a 3 min video and save sending a 20 min email.

  • For booking anything, Calendly. I am on a personal quest to end emails back and forth about scheduling something. I despise that. Anyone can set up a free Calendly and if I want to schedule something with you just send me the link. Solving this one thing will take us 90% of the way to world peace, prove me wrong.

  • For quick graphic design, Canva.

  • For landing pages, Unbounce. ClickFunnels for those building something a bit more than lead capture.

  • For advanced Facebook nerds, Qwaya.

  • For email marketing, I love MailChimp. They just have cool branding and I dig it.

  • For an online course, I love Kajabi. They are best positioned to change online education over the next 10 years.

Lastly, a personal one. For founders out there, realize you need to take your health seriously. Get an Oura ring. Aim for 90+ readiness and the world will be yours.

What have been the most influential books, podcasts, or other resources?

The Bible, The 4-Hour Workweek, and Rich Dad Poor Dad.

For entrepreneurs, I think Rich Dad Poor Dad is mission-critical to read. A lot of people are just really bad at how they think about money and money management in general. Your startup going big and making you a millionaire won’t solve your problems if you have a poor mindset (read the book and you’ll know what I mean). What I would suggest is to read this book, period.

The only podcast I consume from time to time would be the Tim Ferriss Show. Mostly just for the fitness and health-related episodes.

On this subject matter, I do believe a mistake that some folks make is bouncing around from one person to the other. Looking for the best “guru” or the best “system”. At a certain point, you need to just pick one system and take ruthless action. You don’t need to watch another YouTube video.

Just build.

Advice for other entrepreneurs who want to get started or are just starting out?

The first thing would be to make sure that your product or service solves an actual problem in the marketplace. Are people struggling with something and do you have the solution? Is the problem keeping them up at night?

A sure-fire way to know it's perfect is if you are solving your problem. Scratching your itch. If you are constantly wondering “how come nobody has figured out how to do X?”... you are on the right track.

Next is to get someone to pay you for your idea. Don’t just ask someone “hey would you be interested in such and such product or service?” because people will lie to you just to be nice. Get them to give you a payment. You want them to hand over the Amex because they are so excited that someone can solve their problem.

Do NOT spend months or years building your product or service only to find out that nobody wants it. Maybe you need to build out a prototype or a single webpage to get the point across but don’t build out the “perfect” full version (note: it won’t be perfect, I guarantee it).

Lastly, get the absolute minimum solution to market ASAP. This can go together with the second point of getting actual payments. If you tell someone that you will deliver the product by X date and they pay a deposit or in full that will light the fire in you to get things launched. It will also push you to strip out all of the unnecessary.

The perfect example to drive this concept home is with an online course or training program. Perhaps you aren’t building something like that or maybe your product is physical but this just hammers home the concept.

I see so many people who have an idea for a course - and it's a solid idea! But then they spend 6 months, 12 months, even 2 years in one example only to find out that nobody is willing to pay for it.

That the product-market fit is just not there. It would be better to create, say, 3-4 versions of a landing page with various concept angles for your course and then run Google or Facebook ads to those landing pages. Spend a couple of hundred dollars to see what has the higher opt-in rate. Get opt-ins for strategy calls. Speak to people. Are they willing to make a deposit?

I know people that were 100% certain a course was the answer, only to find out that people weren’t interested. But they were interested in a done-for-you service. So they pivoted and now they have a successful business.

Had they spent two years building out the course they might have been disgusted and given up once they found out nobody wanted the course. Instead, they were able to pivot at an early stage and find success.

Are you looking to hire for certain positions right now?

Right now we are hiring account managers. You don’t need to know Facebook or Google ads or even marketing in general. We will teach you our way of doing marketing.

You can always keep an eye on our website for any hiring but just reach out if you are reading this and interested.

Where can we go to learn more?