How Jason Hennessey Harnessed the Spontaneity To Grow His Business

·4-min read

Spontaneity. It fuels disruptive thinking and allows businesses to gain traction, even in highly competitive industries. It’s also an advantage for companies that need to reconfigure their brands post-covid, according to McKinsey and Company. Yet being spontaneous isn’t everyone’s cup of tea, even when they know it’ll be advantageous.

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Some leaders find it difficult to move fast, break things, and move on. For them, a world without consistency is a world without stability. However, stability isn’t all it’s cracked up to be. Sometimes, instability provides the fuel to spark innovation and break new ground.

Breaking Rules to Rule an Industry

Take the unlikely success of Jason Hennessey.

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He’s the CEO of an eight-figure digital marketing company today, but his fortunes were hardly set in stone. As a kid growing up on the east coast, his family battled relentless financial insecurity and healthcare stress. Like so many other plucky entrepreneurs, the rockiness of his upbringing fostered spirit and drive. In fact, it was the uncertainty of the future that caused him to embrace spontaneity and take risks.

“I grew up the son of a single parent who experienced serious medical problems when I was young,” Hennessey explains. “It was an everyday battle to push through day after day. But each morning brought a sense of accomplishment—and opportunity. Thanks to a supportive family, I saw that where you are today isn’t where you could be tomorrow. At the same time, I realized early that if I was going to win in life, I was going to have to lean into spontaneous actions backed by intuition. In other words, I would have to think differently than everyone else.”

A Different Way of Seeing the World—and SEO

For Hennessey, “different” thinking meant seeing barriers as possibilities.

After moving to the west coast, he launched a Las Vegas wedding DJ company. Barely allowing himself a shoestring salary, he put the bulk of his earnings back into the startup. When he realized buying ads in standard print publications wasn’t netting him leads, he went online.

It was the time of Y2K, a perfect moment to explore SEO to the fullest. So he became a self-educated student of all things digital. “Learning is really the key to mastering anything,” says Hennessey. “Skateboarding. Crafting handmade furniture. Crushing the SEO game. Anything. Spend 10,000 hours getting an education and experience, and you’re bound to become an expert.”

After devouring lessons and books on the up-and-coming virtual marketing scene, he cracked the algorithm code. Some might suggest he even broke it, sending a wealth of prospects into his DJ business pipeline. The company grew and morphed into a bigger entity with wider reaches and services. He sold it at 29 for a tidy profit, which he immediately invested in his next venture, a digital marketing agency.

His approach was novel from the start.

True to his unique, instinctive, and unorthodox approach to life and work, he eschewed traditional business planning techniques. For one, his agency didn’t have a website until much farther into its lifespan. “It sounds crazy that a digitally based organization wouldn’t start with a robust site,” he admits.

“Here’s the truth, though: Not having any kind of web presence didn’t hold us back. We grew fast over the first year, making eight figures without the need for a dedicated site for the company. It was backwards thinking, definitely. And it helped us differentiate and focus on getting clients seen rather than publishing our own content.”

Another example of Hennessey’s relentless pursuit of the unexpected was his insistence on short-term contracts. To this day, his team operates on month-to-month agreements. Though this subscription-style model might sound dicey or unpredictable, it’s resulted in a 97% retention rate. As he explains, “I’ve always believed that if you’re doing your job, you don’t need to control your clients. They’ll stay because they appreciate that you’re the ‘real thing,’ not because you’ve put them on a leash.”

To be sure, not all entrepreneurs have Hennessey’s natural penchant to zig when others zag. That’s okay. All can learn from his example if they’re interested in disrupting an industry, particularly after 2020’s economic and marketplace uncertainty.

After all, if an inexperienced young business owner could rank number one on Google for “wedding favors,” anything’s achievable. All it takes is a willingness to let go of the status quo—and embrace the power of a little spontaneity.