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CEOWORLD magazine - Latest - CEO Spotlight - CEO Spotlight: 5 Things I Learned from Dylan Ogline

CEO Spotlight

CEO Spotlight: 5 Things I Learned from Dylan Ogline

Hitting seven figures before he hit 30, this guy has ideas worth listening to. I’ve been doing contract work for Dylan Ogline for years now. I’ve been up to my elbows in his content that whole time, and I think it’s fair to say that I will never be the same.

The 32-year-old founder of Ogline Digital and Agency 2.0 is passionate about what he does, and he has a knack for expressing tried-and-true business principles in terms that are not only layman-friendly but actionable. Imagine taking what works for Nike and applying it to your solopreneur agency.

I find myself applying principles I learned from him in my own business practices, even parroting some of his truisms to my own clients to make myself sound smarter. So maybe writing this is an exercise in attribution … or maybe just absolution. If you know me, do business with me, or have heard me say these things as if I came up with them, the jig is up — I got them from Dylan.

So without further ado, here are five things I learned from Dylan Ogline that changed the way I do business.

  1. Have Your End Goal in Mind When You Start
    “If you want to travel the world while working, don’t start a landscaping business,” Dylan said. It sounds obvious, but it’s amazing how many people neglect this simple principle. What do you most want out of life? If the answer is “a lot of money,” maybe a landscaping business (or any other sort of idea) will get you there.

    But why make all that money? What do you want to do with it? If your only goal is to make money, you will never be satisfied. There is always more money to make, and always someone who has more money. It’s just another kind of rat race.

    “Build my business” is a similarly open-ended goal — and therefore a worthless goal. Your business could always be bigger. But there could be an end-point to your growth if you have an actual endpoint in mind.

    This could be the freedom to travel the world (which means no brick-and-mortar in most cases). It could mean more time to spend with your kids, or to pay for their education, or to build a legacy to pass on to them. It could be to retire your parents, do more volunteer work, or make a difference in the community and even the world.

    If you have an end goal in mind, you are more likely to get there — because you know why you’re working so hard to get there. This will also force you to start and build a business that will allow for the goal.

  2. Don’t Diversify — Focus
    “I never wanted to be a full-service digital agency,” Dylan said, “and I never wanted to be the guy for everyone. I wanted to stick with what works, what I know best, and to do it for the people I could help the most.”

    This is the essence of Ogline Digital, Dylan’s seven-figure agency. It only does one thing, and does it very well — digital marketing management, i.e. social and search ads.

    Plenty of digital agencies also do web design, SEO, content marketing, and a whole slew of other services. Colleagues have told him that he is leaving money on the table by not diversifying.

    Dylan isn’t having it. He believes in focus, not diversification. Even if your goal is to offer more than one service, start with one and become amazing at it. You may discover it’s all you need.

    You may even discover that you don’t even need to diversify your client base. Dylan is a big advocate of “niching down” — picking a micro-targeted client base and learning to solve problems they barely even know they have.

    Why try to sell digital marketing services to everyone when you could sell digital marketing services to “plumbing and heating companies in Pennsylvania?” One of those demographics is much cheaper (and easier) to market to. Plus you’ll sound like a godsend to them.

  3. Sell Your Product Before You Make It
    “There’s only one way to know if someone will buy your product,” Dylan says, “and that’s if they actually pull out their credit card and pay for it. So why wait until your product is done? See if they’ll pay now.”

    It sounds crazy. Sell something before you have even built it? Why not see if they’re interested in a bridge you have to sell over in one of the Five Boroughs?

    But Dylan points out that companies do this all the time — pre-selling new product releases, pre-selling copies of books and tickets to movies, pre-selling whole semesters of college courses before the professor has even prepared the syllabus.

    If someone pays you for a product you haven’t even built yet, they must really want it. Tell them it will be ready in 30 days, or they get their money back. Not only have you proven your concept, but you will have extra incentive to get it done in time. After all, you don’t want to give the money back.

    Ultimately, this principle is to save entrepreneurs from wasting months or even years developing products that no one actually wants to buy.

  4. Don’t Be Afraid to Fire Your Clients
    “It’s hard to say ‘no’ to money when you have none,” Dylan said. “But the sooner you build the habit, the better.”
    I can think of numerous clients I hung onto for dear life, despite the fact that I hated the work and the people. It was money. How could I turn it down?

    Here’s the thing, though — if you have product-market fit, there will always be more customers. It’s up to you whether you want to remain handcuffed to a problem client.

    For Dylan, firing clients is part of the “80/20 rule.” He figures that 80% of his revenue will come from 20% of his clients, while 80% of his problems will come from a different 20% of his clients. So if a client is one of the big headaches and not one of the big revenue-drivers, why keep him around? Firing that client frees up space to get a high-volume client who doesn’t suck.

    Ogline Digital hit seven figures as fast as it did because Dylan honed his client roster down to a “dream team” of a handful of clients. That’s some 80/20 magic right there.

  5. Happiness Trumps Growth
    “When I was broke, I dreamed of making six figures,” Dylan said. “When I hit six figures, I wanted to make seven figures. When I hit seven figures, I started to think ‘What’s the point?’”

    In other words, you can only buy so many cars and Rolexes before it gets old. (Dylan doesn’t drive a Lambo and prefers an Apple Watch.)

    The default business ethic of the last 200 years, at least in the US, is growth at any cost. Bigger is never big enough. Dylan’s father and brother had that same ethic, and he watched it drive his father to multiple heart attacks.

    For Dylan, it’s all a balance — work, physical health, mental health, passion projects, emotional growth, spiritual growth. He specifically designed his business to make him free. Growth-at-any-cost is just another set of handcuffs.

    Dylan just got back from a volcano-viewing trip to Iceland, eager to spend time with his dogs in sunny Orlando. Now he’s developing a training program to teach struggling entrepreneurs how to follow in his footsteps. If that’s not a happy guy, then I don’t know what is.

Good entrepreneurs borrow ideas from other entrepreneurs. Great entrepreneurs steal from them outright. If Dylan happens to see this, I’m confident that he will see my imitation for what it is — the most sincere form of flattery.


Have you read?

Best CEOs In the World Of 2022.
TOP Citizenship by Investment Programs, 2022.
Top Residence by Investment Programs, 2022.
Global Passport Ranking, 2022.
The World’s Richest People (Top 100 Billionaires, 2022).
Jamie Dimon: The World’s Most Powerful Banker.


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CEOWORLD magazine - Latest - CEO Spotlight - CEO Spotlight: 5 Things I Learned from Dylan Ogline
Sophie Ireland
Sophie is currently serving as a Senior Economist at CEOWORLD magazine's Global Unit. She started her career as a Young Professional at CEOWORLD magazine in 2010 and has since worked as an economist in three different regions, namely Latin America and the Caribbean, Africa, East Asia, and the Pacific. Her research interests primarily revolve around the topics of economic growth, labor policy, migration, inequality, and demographics. In her current role, she is responsible for monitoring macroeconomic conditions and working on subjects related to macroeconomics, fiscal policy, international trade, and finance. Prior to this, she worked with multiple local and global financial institutions, gaining extensive experience in the fields of economic research and financial analysis.


Follow her on Twitter, Facebook, Instagram, or connect on LinkedIn. Email her at sophie@ceoworld.biz.