Dylan Ogline was on the brink of failure, relentless drive kept him going

On the volcanic plains of Iceland, one seven figure millennial entrepreneur reflects on his multi-year journey to overnight success.

  (photo credit: Dylan Ogline)
(photo credit: Dylan Ogline)

I met Dylan Ogline in a hot spring in Iceland. Like me, he had been chomping at the bit during the COVID-19 lockdowns and was ready to hit the road. 

He had spent a few months in Europe shortly before nearly every country closed its borders. His business, Ogline Digital, was cruising on seven figures of revenue from just a few high ticket client relationships. 

Having conditioned his lifestyle to facilitate a prodigious travel schedule, cooling his heels at home in Orlando just didn’t suit him anymore. Pandora had opened the box, and Dylan was ready to hit the road as soon as the passport stamps came out again.

“I came to see the volcano,” Ogline said. “In the winter I’ll probably be back to Iceland to try and catch the Northern Lights.”

Yes, it’s a cool place. The eruption he’s talking about began March 19, 2021, about 25 miles west of the capital city of Reykjavik. You could walk absurdly close to it and still be safe. I saw it. It was awesome. It continued until December 21, making it the country’s longest eruption in 50 years.

That’s how Iceland measures volcanoes. It’s some of the newest land in the world, having first burst from the north Atlantic a paltry 20 million years ago. Sitting right on the fault line between the North American and Eurasian tectonic plates, both volcanoes and hot springs arise from near-constant volcanic activity. If you missed this eruption, don’t worry — another one will probably happen in your lifetime.

The constant lava flows have crafted Iceland into an unearthly moonscape of wild rock structures and eerie moonscapes. It’s like taking American Airlines to a different planet.

Like most island destinations, it’s not cheap either. Basic goods and services need to be flown in. It’s not Thailand or Colombia — consumer prices are almost 39% higher than in the United States, not the cheapest country to begin with. 

In other words, no one in that hot spring is broke. And they always had a story. Dylan’s began when he started his first business at the age of 14.

  (credit: Dylan Ogline) (credit: Dylan Ogline)

Getting an Early Start

Considering he grew up in rural Pennsylvania, a stone’s throw from Canada, where the lakes freeze all the way to the bottom in the winter, Dylan waited a long time to get interested in hockey. He fell in love with the sport at ten years old and harbored lofty dreams of becoming the next Scotty Bowman (greatest hockey coach of all time for those not in the know) … but he had a problem.

“I wanted to be the best,” Dylan said. “I’m competitive like that — I always want to be the best in whatever I do. But when I got into hockey, I discovered that I was playing against kids who had gotten their first pairs of skates as soon as they learned to walk.” 

“They had literally been on the ice since they were two or three years old. Some of them had picked up their first hockey sticks before they were out of diapers. And they had trained hard ever since. They were light years ahead of me.”

These boys had such a head start on Dylan that he knew it would be nearly impossible to catch up. Even if he practically killed himself training, they would always be several steps ahead of him. 

While fretting over his future as a professional hockey coach, a chance literary encounter changed the course of his life — his older brother left a copy of Robert Kiyosaki’s Rich Dad, Poor Dad lying around where Dylan could find it.

“I’ve had many mentors throughout my life,” Dylan said. “Mentorship is so important. You’ve gotta have someone whose example you can follow. But I fully believe that you can find mentors in books. In-person mentors are great, but if you don’t have that, the writers of great books can be your mentors, even if you never met them. I haven’t met Robert Kiyosaki — yet — but he’s definitely one of my mentors.”

Dylan devoured the book from cover to cover. He resonated with its message that even high-earning employees tended to fall into an impoverished mindset of debt and overconsumption — that the rich buy assets while the poor buy liabilities, regardless of their income bracket. He also resonated with Kiyosaki’s message that the road to wealth passed through entrepreneurship.

“Both my father and my brother were business owners,” Dylan said. “That’s why my brother had Rich Dad, Poor Dad in the first place. But I was the baby of the family, so they didn’t really talk to me about it.”

But by waking up to the economic principles of Rich Dad, Poor Dad at an early age, Dylan discovered an opportunity.

“Like the kids who started playing hockey while they were in diapers, I had a huge head start,” Dylan said. “If I started down the entrepreneurship road now, in my early teens when I discovered it, I would have a massive head start on other entrepreneurs, who didn’t get started until business school or after college or whenever.”

So Dylan set off to found his first business. It was a decent success … for a while. He was 14 years old. 

Flipping Phones in Pennsylvania

There was a time before the iPhone. In that misty past of the Long Long Ago, the best mobile phones — precursors to what became the SmartPhone — came from Europe. They weren’t that common in America.

If you wanted one, you had to look for an unusual source — like eBay. If you were lucky, you could find one of those fancy European-made phones for maybe $500+ and domestic shipping within the States … say, from Pennsylvania. You pressed “Buy It Now” … and somewhere in Amish country, there was 14-year-old Dylan Ogline, pulling an unopened phone out of a carton and packaging it for shipment and delivery.

He had tracked down a wholesale dealer of these phones, communicated all through email, and negotiated an importation deal with them. They had no idea they were dealing with a teenager. Dylan imported cases of brand-new phones to his parents’ house, buying them in bulk and then he flipped them on eBay for one or two hundred dollars in profit each.

“I was in the black a couple thousand dollars a month,” Dylan said. “At 14 years old, it was all the money in the world to me.”

Business was so good, in fact, that he began to wonder why he was wasting time at high school.

“I began to lobby my parents to let me quit school,” he said. “They weren’t having it. They wanted me to finish high school. So I started pushing for them to let me finish high school using a homeschool program online, which at the time was a totally radical idea. School online? You gotta be kidding me! The books were a few hundred dollars. I was dangerous — I was 14-years-old and cash-rich!”

“They could see how well the business was going, and finally I got them to agree to it. So I transferred to the online school. I never cracked into one of the books. A few months later I formally dropped out.”

Just like that, Dylan’s formal education was over in the 10th grade. 

But who cared? He was making bank importing European cell phones and flipping them on eBay. What could possibly go wrong?

Then, disaster.

“Back then, you needed a merchant account to sell on eBay,” Dylan said. “I had opened one, but they sent me some forms to fill out after revenue started to pick up. It asked for my birthday, and naively I told the truth.” 

“Once they found out that I was underage, they shut down my merchant account. I had no way to collect on my eBay sales. It effectively killed my phone business.”

It was a setback, no doubt about it … but after that first taste of success, how could the future not be bright? Dylan set off to find his next opportunity.

  (credit: Dylan Ogline) (credit: Dylan Ogline)

Amish Romance Novels

Flash forward about a decade — Dylan was in his mid-20s, nearly $1 million in debt, and literally crying in his car.

“I was trying to get out from under a real estate investment, but the deal had fallen through,” Dylan said. “One thing after another was going wrong, I thought I was going to end up in bankruptcy. It was an overwhelming feeling of despair.”

After getting booted out of the cell phone business, Dylan’s subsequent ventures hadn’t lived up to that early promise. Web design wasn’t really going anywhere. His real estate investments underperformed. His attempt to create a better job-posting website went nowhere. A lyrics website never launched. He bought various “start-your-own-business” training programs off of ads. Perhaps the most esoteric of all of them was a program on how to become a micro-niche Kindle eBook publisher on Amazon.

“For a short time, I was the biggest kindle publisher of Amish-themed romance novels on Amazon,” Dylan said. “What a feather for any entrepreneur’s cap. My Pennsylvania roots finally paid off.”

But it wasn’t always funny. To cover the debt service on his loans, he sold digital services, freelance. “I was desperate for money, so I would take any job,” Dylan said. “Need a website? I’m your guy! Need a logo? I’m your guy! Need a PowerPoint presentation? I got you fam! I learned a lot and built up a lot of competencies, but it was a grind. I felt like I was running to stand still. Working a hundred hours was just a warm up for the week.”

The Self-Employed Blues

Dylan was impaled on the wrong horn of Kiyosaki’s Rich Dad/Poor Dad dichotomy. If you haven’t read the book, here’s a crash course on Kiyosaki’s “Cashflow Quadrant.” All forms of income fall into one of four categories:

E — Employment

S — Self-Employment 

B — Business

I — Investment

Basically the book teaches, poor people live in the “E” and “S” quadrants, rich people in the “B” and “I” quadrants. 

While a self-employed person might superficially seem like a “business owner,” you are really only making “B” money if the income is produced by a system that doesn’t require your direct involvement. 

Self-employed people essentially own a job. No boss is telling them to report to work … but if they don’t report to work of their own volition, the money stops.

Compare that to Jeff Bezos. He could never show up to work again, but the structure he built Amazon into — 780,000 employees, 40% market share, and 1.9 million active independent sellers paying Bezos a cut of every sale — will keep putting money into his pocket from now until the end of time. That’s “B” income.

Learning to Drill for Oil

Dylan managed to avoid bankruptcy and foreclosure that time around, but he had felt the branch creak. He was ready to hear what an old mentor had to say when he called him randomly one night.

“This guy had mentored me from time to time over the years,” Dylan said. “I was actually pretty upset to hear from him because I didn’t want to admit to him how lost I was.”

The mentor asked Dylan how everything was going. So Dylan lied and said it was going great. The mentor saw right through him and asked how it was really going.

Dylan broke down and told him all of it — the debt, the failed business, the weeping breakdown in the car.

The mentor laughed — not to be cruel, but because he had been there before. The story no one wants to talk about in these “rags-to-riches” success stories is that every one of them runs into that dark night of the soul. The S&P 500 is populated entirely by superman and superwoman who at one point broke down weeping in their cars.

When he regained control, the mentor gave Dylan the idea that changed his life and set him on the path to create Ogline Digital — “Dylan, you need to stop trying to build an airline and start digging for oil.”

“‘Thanks for the fortune cookie,’ that’s what I thought,” Dylan said, laughing.

But the cryptic advice was just what he needed to hear. Entrepreneurs know that building an airline is an impossible business venture. Billionaire tycoons go bankrupt wading into those shark-infested waters.

Meanwhile, almost anyone can get rich drilling for oil. You don’t have to be the best oil-driller in the world … All you have to do is start digging and be sorta OK at it.

“This guy was telling me to simplify,” Dylan said, “to identify the highest-margin business I had going for me, the one where even if I wasn’t the best in the world, I could still make money at it.”

“The kid in me, still on the hockey rink, didn’t like that,” he said. “I always want to be the best. But at the time, my office was in the basement of my house, which froze like a meat locker in the winter. My desk chair was a five-gallon Lowes bucket. I wanted to be the best, but I was ready to settle for getting out of that damned basement.”

Dylan took his mentor’s advice and took a pitiless look at the business ventures he had up and running. A few of them were making money, but one of them was overperforming — digital marketing management, one of the digital services he had been offering on a freelance basis.

“I wasn’t a pro at digital marketing at the time,” Dylan said, “but I knew more than a complete beginner. I had run campaigns on Google and Facebook for my own business startups … I had clients who asked about it and as always, I said yes, I figured I could make some pocket change by running campaigns for other people.” 

“I had been fascinated with it ever since Google ads first debuted,” he continued. “I was amazed that Google had invented a way for companies to basically buy ‘growth.’ I wasn’t an expert, but I could at least move the needle.” 

But Dylan noticed something peculiar and promising about his digital marketing services — when a campaign worked out, clients were eager to double down on those campaigns, to throw more money at it. Why wouldn't they? Thanks to Dylan’s effort, they were making more money than they spent.

What if, instead of a flat fee, Dylan charged a percentage of the ad spend? Then, if they doubled down, Dylan’s revenue would double as well. Ditto if they tripled, quadrupled, or 10x’ed down.

More importantly, it was becoming clear that he could outsource or even hire team members affordably to execute some of the nuts and bolts of his successful campaigns. There was a “B” hiding in here. Digital marketing management was starting to look like drilling for oil.

Volcanic Rise

Relaxing in a volcanic hot spring, Dylan Ogline reflects on how far he has come. It isn’t flipping cell phones on eBay, but Ogline Digital does 7 figures a year with a remote skeleton team and affords its 32-year-old founder the freedom to live life on his own terms.

Like a volcano, he burned hot at the starting line, but like a volcanic island, he incubated under water for years before finally bursting through to the surface.

“If I knew how long and painful the road was going to be, I might have done it differently,” Dylan said. “Part of me is glad though. I’ve been so incredibly blessed in my life. I’ll be honest, when I felt like I was going to be nothing but a failure, when things were really tough, it sure was tough to see that! But from here, it all seems worth it and the struggle was a blessing in disguise. I’m glad I started early, that's for sure!”

One door closes, another one opens; that’s the lesson here. It was very true for Dylan Ogline. He kept going when everything looked like it was falling apart. There is a takeaway for all of us in that. No matter what, keep going and keep pressing on. And don’t build an airline.

This article was written in cooperation with Gwen McDaniel