Today in Business, Size Isn’t Everything

Opposed to the “growth at any cost” ethic of yesteryear, laptop entrepreneur Dylan Ogline represents a new, “lifestyle-first” approach to business.

It’s a loaded question in the business world, among other places. Sometimes it’s an unspoken rule, other times it’s spoken quite overtly — never stop scaling. Never stop growing. There’s never enough revenue, never too many employees, never too big and imposing of an office. You only stop growing when you die of a heart attack (probably at age 59).

To Dylan Ogline, 32, founder of seven-figure marketing agency Ogline Digital, this represents old-order thinking — even magical thinking, to be challenged at every turn. 

“How many business ‘gurus’ have we heard say ‘If you’re not growing, you’re dying’?” Ogline said when we caught up to him on a spiritual walkabout through the epic volcanic moonscapes of Iceland. “Well, I don’t feel like I’m dying.”

“I’m always learning,” he added, “so I can offer clients the cutting edge of digital marketing best practices and continue to deliver results. And as long as I do that, I will always have happy clients. But why do I want to get bigger? I’ve got better things to do.”

For Dylan, those “better things” include travel, raising his dogs, volunteer work, ice hockey, and mentoring other aspiring entrepreneurs through his coaching program, Agency 2.0.

Deciding When to Stop Growing

It started with a conscious decision. “When Ogline Digital grew to seven figures, I took stock,” he said. “My first goal was six figures. When we blew past that in less than six months, my next goal was seven figures. We blew past that in two years, maybe three. What next? Eight figures? Nine?” 

“As the agency owner, I no longer worry about money in my personal life,” he continued. “I can afford just about everything I might care to buy. So why am I doing this, if not to live free? If I chase growth for the sake of growth, then I’m a slave to that growth imperative and no longer free.”

Ogline didn’t have to look far for object lessons of this effect. His father, as well as his brother ten years his senior, were both entrepreneurs. They believed in growth at any cost — offices, armies of employees, 80-hour workweeks, donut lunches, expanding waistlines, all in pursuit of more more more. 

He has watched them pay the price, too — multiple heart attacks for his father, and he fears the same fate for his brother.

“They still don’t think I have a ‘real business,’” Ogline said ruefully. “But I was pretty clear in my mind that I didn’t want to follow the path they were on. It just looked miserable.”

A “Lifestyle First” Approach to Business

In prioritizing happiness and personal fulfillment over dominance and zero-sum competition, Ogline represents a New Guard of entrepreneurs. He runs a lean, remote team of twelve who know their job and diligently do it, only contacting him if there’s an emergency. Despite being based in Orlando, his office is his laptop, and his workday doesn’t change no matter if he finds himself in Iceland or Asia.

It’s hard not to notice that this is a kinder, gentler approach to business. “I’m not trying to dominate my niche and become the ‘Xerox’ or the ‘Kleenex’ of my sphere, where my brand name is literally synonymous with the product to the exclusion of everyone else. I just don’t have the patience, or the need for that kind of dominance.”

“Instead of trying to squeeze people out, through Agency 2.0 I’m actually inviting people in,” he continued. “I know this space, and believe me — we’re nowhere close to the saturation point for digital marketing agencies. I could mentor thousands and thousands of students who go on to start successful digital agencies and still not scratch the surface of the demand.”

LA Weekly