Why the Cart Belongs Before the Horse

Dylan Ogline firmly believes this kind of mentorship can mint successful entrepreneurs

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Most aspiring entrepreneurs have it entirely backwards. Digital nomad Dylan Ogline is here to set them straight.


Dylan Ogline is here on a mission of mercy. He has a kind demeanor, at least compared to Alec Baldwin in Glengarry Glen Ross. But he will look right at you with those kind blue eyes, and then push you out of the nest with both hands and expect you to fly.

“I tell my students to move fast, break things—to fail fast and fail early when there’s little on the line,” he said. “I want them to sell their product or service before they have even built the product or service.”

If that sounds unethical, remember that it happens all the time up the echelons of business—mavericks sell angel investors on ideas that don’t exist in the real world yet. If the idea is good enough, those AIs write huge checks.

Back on Planet Earth, where Dylan’s students in his training program Agency 2.0 often find themselves, it becomes a little simpler—pitch your product to your ideal prospect, before you build the product. If they pull out their credit card, you know you have a winner.

Think of how much time you would save by putting that cart before the horse—no time wasted building a website or funnel, shooting sales videos, designing business cards, setting up Amazon FBA, prototyping and building social media assets … for a product that, after six to twenty-four months of development, no one will even pull out their credit card for.

In a tech-obsessed ecosystem of wannabe entrepreneurs, Dylan’s approach is refreshingly old-school. Ogline Digital, the seven-figure digital services agency he build his laptop lifestyle around, is typical of the Millenial ideal—a lean, mean, and scrappy business with low overhead that he can conduct from his home in Orlando, or from a hotel terrace in Thailand.

But his roots are in old-school business. His father and older brother—Boomer and Gen X respectively—owned brick-and-mortar businesses. They sometimes scoff at the digital-nomad baby of the family, who can’t bring himself to build a “real business.”

They should be more proud of him. Dylan’s approach to business revolves around people more than processes, a traditional approach. Yes, he advocates for keeping it lean, but he’s more concerned about solving peoples’ problems than building the perfect funnel, learning some sort of SEO kung fu, or chasing shiny objects like Bitcoin or TikTok.

He discovered his first unique value proposition for Ogline Digital by hitting it off with his plumber and inviting him out for a beer. Over that beer, the plumber revealed deep pain points that Dylan could design a direct-response digital marketing solution for, and then pitch it to other plumbers.

Agency 2.0 came about because people Dylan came across in his daily life kept asking him how he did it, and if he could help them do it to. He would have gladly given away his advice and mentorship for free to a select roster of protoges, but he discovered what coaches since time immemorial have discovered—people don’t value free advice, so they don’t act on it. But charge them for mentorship, and they tend to act.

Dylan firmly believes this kind of mentorship can mint successful entrepreneurs, because it did for him. But it requires a fundamental flippin of the script—doing things differently than the nine out of ten hopefuls whose businesses fail within a year.

“As much as I push the message,” Dylan said, “I still catch my students tinkering on their websites, designing their business cards, sketching outlines of the final product … anything to procrastinate going out and getting the cash register to ring.”

“I’m telling you though,” he said, “once that cash register rings, you have to deliver the product. It’s the best motivator in the world, because if you don’t produce a great product, you have to give the money back!”