What 25 Years in the Marketing Business Has Taught Me

This year marks 25 years that I’ve been trekking around the marketing industry. A quarter of a century really sounds like a long run, and although I don’t feel I should be old enough to have that under my belt, unfortunately, I am.


Let’s set the stage: In the mid-90s I was halfway through my tenure at Western Kentucky University. Coolio’s Gansta’s Paradise was all over the radio, OJ Simpson was on trial, Thunder Gulch won the Kentucky Derby, and Jerry Garcia passed away. What a long strange trip…  Just look at that guy… he has no clue what’s ahead. Hell, he’s still a journalism major barely getting by. It was that second half of college, though, that planted the marketing seed. I declared marketing as a Minor, I took an International Marketing course one summer in Ireland, and even got to participate in focus groups and the process of creating an ad campaign for Ireland Tourism. Check out the rough director’s cut. This felt real. We helped make something that evoked emotion, even if I was only a tiny part of it, it lit a fire in me.




After school I did a longer stint at Camping World in Bowling Green, and Affinity Group based in Ventura, California. (great place to learn how to surf and gorge on tacos in your off time… by the way). Those jobs formed a base of knowledge and had me rubbing elbows with executives in larger organizations, building marketing plans, managing processes, and directing multi-million dollar budgets. It’s exactly what I needed at the time to sharpen the pencil of my skill set.


While in my cubicle(s) at those jobs and traveling between offices in Kentucky, Colorado, California, and other locales, I started to get restless. A few start-ups later, and I was out on my own. I sold two of those start-ups (both marketing-oriented businesses) for a song. But, they were far from being fully formed, and so  was I for that matter.


Next stop on the marketing journey was a bit of an undefined era. I was about to learn that, while I was hiding behind my corporate spreadsheets managing my team, marketing had changed – and so had I. Putting my 1 month notice in at my corporate job, I wrote a 50+ page instruction manual on how to do my job for the next in line, and said my goodbyes. I thought surely they’d call me every day to “pick my brain” on something only I knew about in the company… they did not. I learned pretty quickly that everyone is replaceable. And, just like that, I was on my own. I planned to take a full year off. My wife was gracious enough to give me the time to “find myself.” Within a week I had an offer to come consult part-time at a new start up. I’d had a “playbook” up until this point. Here, I was doing all the marketing from top to bottom; it was exciting. I was nervous, but didn’t show it. Alongside that gig I was doing some travel writing and flexing my journalistic muscles. And on top of all that, I was asked to run social media accounts (when it was a new thing) for a handful of smaller companies. I was fumbling with the new tech and marketing reality. But, no doubt, I was quickly getting busy again.

So much for the year off.


There is a sharp difference between working for someone and working for yourself. Firstly, there isn’t a person telling you when and where to be… instead, everyone does. You don’t have a single manager – all your clients are your manager. And secondly, there are no steady paychecks when you work for yourself – some weeks I did great, others I came up emptyhanded.


When I reference owning my own business, I don’t mean owning a franchise or being part of a larger company and owning your own branch – I mean really being on your own, solo… isolated. I was doing my own books, being the admin, the janitor, the sales lead, and the CEO all within the same hour – and having no experience doing any of it. I was flying the plane as I built it, and I didn’t have a pilot’s license.


I learned a lot in the years on my own. If a client needed a Google Ad, I didn’t say “I’m sorry, I don’t know how to do that.” I read up on it and learned – created an account and failed… until I didn’t. If I hadn’t built an affiliate network, I bought a book and some software and stayed up until 2 in the morning figuring it out. I called mentors and hired old friends. I built teams for each project and  learned how to pick the right ones. I was doing a lot of things, and doing them barely well enough… I knew that wasn’t fair to the clients, or to me. So, I pumped the brakes on the travel writing gig – it paid crap anyway. At least that’s what I told myself. No more 2 week stints island hopping in the South Pacific, no more paddling the Sea of Cortez with the sea lions, no more climbing Cotopaxi and learning Spanish in Ecuador… I needed focus. I needed to stay home and figure out how to be a good business owner. And, I knew for sure I couldn’t do it on my own.


After pairing up with the infamous Chad Webb, we were off and running with CrowdSouth. We were able to split the roles, which was a relief for me. He took on the things he was great at, and I did the same. We’ve learned a lot in these 9 years. Partnerships are tricky, but such a catalyst for growth.  Initially, we were everything to everyone – Bad Idea. Any good business owner knows that niching is the recipe for a quality product. Do fewer things. Do them well. And pair up with good partners who can handle the rest. At this point we focus on what we consider larger scale clients, we snap in as a marketing team or compliment their existing team. We focus on digital marketing – Social – Sites – Search. We are comfortable telling a client they are not right for us, and we are not right for them. We are getting better all the time. We run marketing campaigns in all 50 states, at least 4 countries, and manage more money in marketing budgets than I would ever have been comfortable with back when I was considering a marketing degree and listening to Coolio at the frat house.


I have no plans of slowing down. I want to give more back to my community – they made me who I am, right?! I do have plans to continue to focus more intently, however. To let go of some things. These 25 years have taught me that a marketer should always surround themselves with better marketers, specialists, and badasses. Dig in and learn it all. Find and hone in on what you are good at, and shed what you’re not.



Thank you to all my mentors and confidants over the years. I am one lucky human to have had that support and expertise in the marketing world that I’ve had access to. I’ve not been great at much, but I’ve been good enough at plenty of things, and that has opened the door far more times than I deserve.

Jason Heflin

By Jason Heflin

Jason Heflin is one of CrowdSouth’s owning Partners and brings years of marketing experience from his past lives as a corporate marketing manager, writer, and freelancer. He also plays the ukulele for fun, which is cool.

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