How to Grow a Business in a Digital First World According to Jason Hennessey

by / ⠀Startup Advice / April 28, 2021
How to Grow a Business in a Digital First World According to Jason Hennessey

Disruptive. Disorganized. Distracted. That’s what Jason Hennessey’s elementary teacher felt about the young pupil. In fact, he was so sure that a turnaround was in order that he sent a note to Hennessey’s mom. However, like most entrepreneurs, Hennessey’s impatience (and perhaps impudence) turned out to be his strength when he started to grow a business. 

By age 22, Hennessey was hardly the ne’er-do-well his elementary teacher might have predicted he would become. Instead, he was a bootstrapping CEO—and on his way to becoming an SEO expert, speaker, author, and executive. And he did it all by leaning into his passion for sniffing out opportunities and following them full steam. 

Today, Hennessey is internationally recognized for his adeptness at understanding and reverse-engineering algorithms to earn eyeballs and generate buzz. His self-taught knowledge has birthed both Hennessey Digital, a full-service digital marketing agency, and Hennessey Studios. Yet he keeps cutting his tech teeth in an effort to stay on top.

Because of his deep internet capabilities, Hennessey has developed a skill for winning in the digital age. If you’re trying to grow a startup or otherwise climb the entrepreneurial ladder, he has several key pieces of advice. They’re based on his mastery of launching (and selling) companies in a digital-first economy.

1. Get comfortable with any tech that makes you uncomfortable.

Telling people, “I don’t do tech,” or, “I don’t like social media” doesn’t fly. In fact, it can end up making entrepreneurship harder in many ways. Even if you don’t have a Facebook account or use Slack, you need to familiarize yourself with platforms and solutions. Otherwise, you won’t be speaking the same language as your employees, vendors, or customers.

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Hennessey had the advantage of coming of age as the internet was just taking hold. However, he has never allowed himself to sit back and relax. He remains vigilant about understanding technology, including products and sites he doesn’t anticipate using. Take a page from his desire to be a perpetual student of the digital world. Read everything you can and stay on top of the fast changes in online business and marketing. At the same time, don’t think you have to be always focused on technology to grow a business. Hennessey grew his first digital marketing company for a year without a website presence. However, he knew the value of sites… and has one now.

2. Make yourself an authority in a subject that excites you—then self-promote like crazy. 

To start and grow just any business won’t do. You need to find something you can be passionate about. After all, you’re going to spend long hours at work. Shouldn’t you love the topic area that’s going to permeate your days and nights? Hennessey believes strongly in getting 1% better daily, as well as following the 10,000-hour rule. (Not familiar? It’s from Malcolm Gladwell’s “Outliers,” which posits 10,000 hours is the bare minimum for topic mastery.)

As you start to amass more know-how about your chosen subject area, be sure to tell the world. Host a blog. Start a podcast. Offer to speak at in-person events or at webinars. Write guest articles for publications, or publish pieces on LinkedIn. Hire a ghostwriter to help put your thoughts into a solid book format. Make your expertise known in all the online and offline verticals you can. Digitization makes it easier than ever to put yourself “out there.” Build your chops with self-education and then leverage publicity avenues to cement your street cred.

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3. Hire talented people you can trust, and then get out of their way.

Hennessey didn’t get to be the head of a $10MM+ business that has charted the Inc. 5000 list twice by himself. He did it by hiring well and then leaving any micromanagement tendencies in the parking lot. By vetting candidates early and onboarding thoughtfully, he’s been able to keep a crew of more than 125 people engaged.

When you’re just beginning your journey as a founder, you might feel the temptation to make every decision. As soon as you bring one more person into the mix, you’ll need to delegate. So take your recruitment process seriously. Use the Internet to not only find superstars but to vet them. When one accepts an offer, provide mentorship and training, but let them make choices. You’ll have happier employees who rave on Glassdoor about your company, which will encourage more winners to apply for openings.

4. Know when it’s time to let your baby go.

Early in his career, Hennessey entered the entrepreneur ranks as the owner of a Las Vegas-based mobile DJ company. Over the years, he taught himself the skills he needed to win by using internet marketing focused on organic traffic through SEO and PPC. Eventually, he started another one. By the time he was 29, his companies were doing well… so he sold them and started over.

Understanding when to say goodbye to your startup, particularly your first, can be difficult. Is it better to wait until you have a mature product? Or does it make sense to look for a buyer when you’re still growing your business? Every company’s trajectory is different, and markets can have a lot to do with timing. Nevertheless, avoid holding on to your “baby” too tightly. If you have the heart and mind of a dreamer, you’re sure to launch more fireworks.

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5. Break the rules once in a while. (Or a lot.)

It’s okay to break some rules when you’re guiding your ship. It might even help you survive or become a differentiator. Hennessey constantly looks for ways to push the envelope of what’s “supposed” to happen in whatever industry he works. 

For instance, his agency doesn’t insist upon long-term contracts. He prefers to give clients the ability to engage in monthly contracts. This type of subscription-based thinking is highly unusual. Why does he do it? The move helps clients feel less locked in, which eases their minds. It also keeps his team hungry to do their best all the time because they’ve given clients an out.

Did a sports coach doubt that you’d make so much as a scratch on the world? Are friends dubious when you tell them your biggest goal is to pitch an idea to angel investors? Not having everyone’s support can be hard. It can also be motivating. Just ask a kid called Jason Hennessey, whose spunky attitude miffed a teacher—and sparked the seeds of entrepreneurial success. 

About The Author

Kimberly Zhang

Editor in Chief of Under30CEO. I have a passion for helping educate the next generation of leaders.


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