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How A Spontaneous Mindset Helped Jason Hennessey Grow His Startup and How It Can Help You, Too

Data drives the world. It informs business directions. It provides a wealth of education to budding entrepreneurs. 

 

But could data points be the key to making your childhood dreams of owning a sports car a reality? Not necessarily. Even if you’ve built a professional career around data, like serial entrepreneur Jason Hennessey has done.

A self-professed data junkie with a penchant for facts-heavy SEO, Hennessey’s launched and sold multiple startups. Each company he founded used data to the max. Yet he’s relied just as much on gut instincts as figures and analytics in his professional dealings. In fact, he credits spontaneity as a major factor in all decision-making.

When and Why Practical Spontaneity Edges out Statistical Analysis

Of course, defining spontaneity in a corporate sense is critical. In everyday life, spontaneity can present itself in irrational ways: A shy person joins Toastmasters on a whim. Two people meet during the day and get married that night. That’s spontaneity, but not the type of practical spontaneity that has guided Hennessey.

Practical spontaneity is a different beast than erratic, unexpected spontaneity. Rather than being completely off-the-wall, it’s buoyed by instinct. That is, the mind uses inputs to choose specific courses of action. From an outsider’s view, the actions may seem sudden. However, to the spontaneous individual, they make perfect sense given historical information.

Take Hennessey’s first major company, a mobile DJ service targeting people, event planners, and corporations within the Las Vegas region. As opportunities to partner with other entities arose, he thoughtfully jumped into business relationships. These were spontaneous moves because they happened quickly. Nevertheless, they were strategically focused—and they netted Hennessey the ability to grow his brand and profit margins.

Tips to Harness Practical Spontaneity in Any Startup Situation

Maybe you’re not someone who naturally leans toward spontaneity in any form, practical or not. That’s okay. You can develop the ability to be spontaneous when it matters most. In fact, you may find that you leverage practical spontaneity more often than you would have imagined. 

Below are a few ways to incorporate spontaneity into your entrepreneurial dealings. 

1. Learn to trust your natural instincts.

You’re presented with a list of facts, but you’re not convinced. Why? The answer could be those nagging thoughts in your head. Are they just idle worries? Or could they be warnings?

Everyone’s born with survival instincts. As a business founder, you’ll want to figure out when to listen to your gut. For instance, after Hennessey sold his first two businesses, he was asked to speak about SEO to lawyers. The speaking engagement led him to dive into the legal industry as a marketing guru.

Though Hennessey lacked any kind of law-related background, he slid into the niche. Data might have suggested he hold back. Yet his instincts told him that he could make the transition based on his skill sets and personality. The gamble—which wasn’t truly a gamble at all—paid off and moved his career into another realm.

2. Put the cart before the horse sometimes.

As the old saying goes, you shouldn’t put the cart before the horse. Yet if you wait until everything’s perfect, you might miss out on opportunities. Consequently, you may occasionally want to do things backwards with the hope that everything will fall into place.

Today, Hennessey’s the CEO of Hennessey Digital. The digital marketing company focuses on SEO, and employs more than 125 team members. Hennessey Digital brings in more than eight figures annually. Nevertheless, the organization was launched without one key ingredient: a website.

What could possibly have led Hennessey to even consider making such a bold move? Again, it was practical spontaneity. He felt he had enough of a client base to start up without a major web presence. He was right. To be sure, the company has a robust site and digital collateral now. But putting the cart before the horse certainly worked well enough in the short term. If Hennessey had held off, he might have found himself in a different situation today.

3. Stop thinking that you have to do things a certain way.

When spontaneity becomes more comfortable, you’ll notice that you see life with fresh eyes. Specifically, you’ll begin to notice that there are many routes to get to each destination. Sure, some routes are more challenging than others. But where there’s a will…

Hennessey grew up under difficult circumstances. His family experienced financial insecurity. Yet he never saw just one avenue before him. Rather, he searched for creative methods to move forward and get what he wanted. In other words, he was open to being spontaneous, such as joining the military right out of high school.

Diving into a military occupation opened doors for Hennessey and allowed him to attend college. Though he didn’t go into the military without scrutiny, he made the leap based on instinct and faith. Again, his willingness to make his own path turned out to be ingenious.

As an entrepreneur, you need to develop plenty of abilities. Just don’t overlook the importance of leveraging practical spontaneity. Yes, study your data. But listen to your gut, heart, and mind just as intently.

Author : Holly Hutton

Born in the Big Easy and raised in the Sunshine State, Holly has spent the last five years brunching in the Big Apple and bantering with Big Ben. As a wandering writer, techy-in-training, and avid alliterator, Holly has written everything from educational policy and political news briefs to web content and travel blogs. She is thrilled to be a part of the KS team and working with a community of smart, savvy, entrepreneurs on all things startup!

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