“Digital consulting was really kind of like the wild, wild West. There wasn’t a whole lot of resources online that talked about it, and the ones that did, you didn’t necessarily know if you could trust what you were reading. There was no college curriculum that was offering these types of courses.”

It’s hard to believe now that such a statement could be true. After all, search engine optimization turns the cogs in the machine of our modern everyday functioning. We need the internet. And we need one of the most basic elements of building websites.

However, this wasn’t the case for Jason Hennessey back in the early 2000’s. It all started when he invested a good 5,000 dollars in the development of a wedding directory website. He was generally satisfied with the outcome, but noticed an issue: there wasn’t enough traffic on the website. A plea was brought up to his website developer, but to no avail – the man was, unfortunately, not well-versed with the idea of digital consulting since the subject was, at the time, unpopular. It was this stone on the road that pushed him down another path, one where he had to get his hands dirty in the murky, unfamiliar waters of digital consulting.

And he had to do it himself.

At the time, there weren’t college courses on search engine optimization. Online articles and resources on the subject were scarce. So, Hennessey resorted to the traditional, time-tested solution by which many successful entrepreneurs fervently swear: he bought a book. It was Aaron Wall’s book titled, quite literally, ‘SEO Book’. He read it once. And then one more time. Hennessey clung onto this book and currently deems it his ‘SEO Bible’.

He didn’t truly know what he was doing at first. He would practice on his own, but then eventually find that some things have broken under his own hands. That was when he would go back to his well-loved book to troubleshoot the issue until practice made perfect.

“I’m very compulsive,” Jason admits sheepishly. “When I start to get interested in something, I’m, like, a 150% in on it. When I started to practice digital consulting and started to get results, my curiosity began to lead me down different paths.”

One book led to another, and then another, which subsequently led him to read up on various digital-consulting-related articles online. This sent him down a rabbit hole – he would build relationships with like-minded people who were experienced in the digital consulting world, lie in bed at night skimming through the latest online trends, and followed digital consulting giants on social media in order to get a hold of even the smallest crumbs of information he could absorb. Hennessey didn’t need too much forced discipline in order to maintain this practice of teaching himself. He believes that, if a person is passionate in a certain subject, nothing much else should be able to get in their way.

“I guess, when a student is ready to learn, a teacher will appear – and my teacher came in the form of many different mediums.”

It was this passion which fueled the fact that there was never a moment when he felt he wasn’t doing enough by learning on his own. He dedicated most of his free time researching, learning, practicing and tinkering with websites. He never once had the idea that he was being lazy, or that he wasn’t a go-getter. Like any person in love with an idea, he knew this was something towards which he was ready to dedicate a huge portion of his blood, sweat and tears. 

Some may doubt the idea of a complete novice picking something up on their own and making something substantial out of it. This is where the idea of mandatorily pursuing a traditional college course applies. Of course, this method does work.

But Jason Hennessey’s growth in the online world stands as testament to the fact that self-learning is possible. He doesn’t discredit the experience of college courses – rather, he comments, “For me, I think that colleges are set up to teach you how to learn, not necessarily what to learn. You can only get so much from college. It’s what happens once you kind of get out of college or once you leave class – are you genuinely interested in what you are learning?” A genuine interest would spark a whole fire: if one were interested in a specific topic, they would start to pay more attention to their classes. Eventually, that wouldn’t be enough. More knowledge has to be obtained: further research must be done. An individual who has fallen in love with a subject or idea would start to read more, to watch videos on a certain topic, to network with other individuals who, too, have fallen in love with the same subject. Hennessey wraps this notion up with a neat bow by saying: “Your whole world starts to become catered to the subject you’re interested in, whether it’s medicine or technology [and so on]…It comes to where your heart is.”

All his persistence paid off two decades later, when he is now the proud owner of iloveseo.com. His experience and knowledge is constantly relied upon by various professionals and aspiring digital-consulting-enthusiasts. Hennessey is also frequently invited as a guest speaker at various digital consulting forums and conferences worldwide. His hard work and commitment to success has produced his own digital marketing firm, Hennessey Digital, which has earned a place on the Inc. 5000 fastest-growing privately-held companies for 3 consecutive years. 

One of his more prominent principles in life is that one should never be the smartest person in the room. There is always somebody out there from whom so much knowledge and wisdom can be obtained.

When asked which advice he would give his younger self or other young entrepreneurs in the technology industry, Hennessey perfectly articulates: “You’re going to make a lot of mistakes. And that’s okay. You want to fail forward, and you want to be 1% better than you were from the day before. Just 1%. Live and learn.”

There is an old saying that, if a forty-year-old man still views the world in the same manner as he did when he was twenty, he has just wasted twenty years of his life. Indeed, this principle based on the trial-and-error method holds true in the life of any aspiring entrepreneur – or essentially anybody who has found their passion in anything. Hennessey’s story is proof that there is only one simple thing a person should do if they want to pursue a passion: learn. Learn, no matter how many mistakes are made.

As Hennessey says: “Fail forward.”