This month we hopped onto the Tour Bus with Dennis Shiao, a long-time influential content marketer, today known for his regular columns for CMSWire, The Content Marketing Institute and his previous work at DNN Software.

Aside from grabbing the opportunity to pick his content marketing brain, he’s recently joined the gig economy and gone freelance, a move a lot of Rockstar marketers are considering and we wondered how this tour was working out. Ian Truscott asks the questions.


Hi Dennis, tell us about your current gig

I love my current gig as an independent marketing consultant. Aside from occasional face-to-face meetings in client offices, I work remotely and set my own hours. I love the freedom! Also, I’m excited and energized by the variety of projects I get to work on, as well as the different industries my clients are in.

I might curate healthcare content in the morning, learn about advancements in artificial intelligence in the afternoon and write copy about robotic process automation in the evening. I’ve done assorted marketing roles over the past 10+ years; as a consultant, I take on the roles I love to do the most: content marketing, product marketing and social media marketing.

You describe yourself as an “accidental freelancer” – how did that come about?

Aside from a short stint during the dot-com bust, I’ve been a full-time employee my entire career. Last year, I was laid off from a full-time role and began the process of looking for a new job. I loved what I was doing (e.g., content marketing for a B2B software company), so I was looking for a similar role.

A new role was slow to surface.

In the meantime, I had taken on small freelance projects to bridge the gap (with income) and keep me busy. If I could land some more work and bill clients the equivalent of a 40-hour week, then I’d stop looking for a full-time position.

I was able to pick up a few more clients and haven’t looked back. Sometimes, accidents are meant to happen.

What advice would you give to anyone else making that jump? Whether accidental or otherwise?

If possible, try things out while you have a full-time job. It’s similar to aspiring entrepreneurs, who build and prototype new products at night and on weekends. When they’re ready to make the leap, they leave their jobs to dedicate their time and energy on their new start-up.

Of course, this should be done in a way that doesn’t compromise your job performance or productivity and is not competitive to your employer’s business. Similar to the aspiring entrepreneurs, getting some experience under your belt can help you decide the right time to make the leap.

Also, know that you’re quite similar to the entrepreneurs. The difference is that the product you’re selling is … YOU!

Any bumps in the road so far?

As with anything in life, there are trade-offs.

Fortunately, I’m now on my wife’s health coverage. Otherwise, I’d need to pay for health insurance. Also, on holidays and vacations, I don’t get paid unless I work. That’s taken a little adjusting to.

In a full-time role, I was paid a fixed amount, whether I was swamped or not busy. In freelancing, those “up and down” periods translate directly into an EKG-shaped income chart. I’ve been fortunate that the ups and downs tend to balance out.

One week, I’ll feel a little down because I’ve had less to work on. And then suddenly, on a Friday afternoon, I’ll hear from three clients who have new projects for me. So I know that the following week will more than offset the current week.

It’s all good, just new things to get used to.

Having followed you for a few years, I think of you as a content marketer, from your work at DNN Corp and your writing for the Content Marketing Institute – what got you into content marketing?

It starts in high school, with a football video game on the IBM PC. It was an X’s and O’s game — meaning, there literally were X’s and O’s as players on the screen. The offense would call a play, the defense would call a play and the computer would show the play unfold.

I had three friends come over to play. We got to the point where we’d have a tournament. Like a journalist, I suppose, I’d write up the tournament summary (with commentary, of course!), print it out, then share copies with my friends.

That led to writing sports columns for the high school newspaper. Once, I covered an evaluation of our school (by the state), which became the front page story of the paper.

In my first job out of college, we’d play wallyball (e.g., volleyball played on a racquetball court) and I’d write up game summaries (sprinkling in a little humor) and email them to the entire office. Colleagues would reply, “You missed your calling as a sportswriter!”

I ended up getting a bachelor’s degree in computer science, but you can see how the writer inside me was trying to climb out from an early age. About 10 years ago, I started formally doing content marketing and it felt so natural.

You share a lot of great advice on content marketing, what’s top of the charts for you?

It’s been said that the social media algorithms know more about you than your family. Great content marketing starts with understanding your audience better than they understand themselves. That starts with immersion (e.g., spend time with them, with a strong preference on face-to-face time) and adds on empathy.

It’s only from that depth of understanding that good content marketing can flow.

With empathy, I don’t mean an understanding of why they need your product. Instead, you need to understand their wants, needs, desires and fears. Learn about their hobbies, their favorite shows, their favorite websites. Get as close to them as you would a significant other.

It’s only from that depth of understanding that good content marketing can flow.

And what marketing tune sucks? What would you chuck into our portal to hell – The Rockstar CMO Swimming Pool?

Lately, I’ve taken an interest in the art and craft of email newsletters. I signed up to personal newsletters, as well as those from B2B brands. And oh boy, the latter. I can’t yet name a B2B brand who’s newsletter I admire.

Most come out a few times per month and are a re-hash of content the brand recently published (e.g., read our blog post, view this on-demand webinar, download this eBook). It’s 100% “me focused” and has zero empathy for the subscriber.

Off the top of my head, I can’t think of a single issue of a B2B email newsletter that linked to a piece of content that’s not their own.

What’s next for Dennis – where do you think this tour bus is going?

Micro-level: I love freelancing and can see myself doing it for the foreseeable future.

Macro-level: I want to apply my marketing skills towards a project or undertaking that makes the world a better place. That’s a rather broad statement and I plan to whittle that down to something specific. It’ll probably be something related to serving the less fortunate and making their lives better.

If you’re reading this and have ideas or want to collaborate, I’d love to hear from you!


Dennis is an independent marketing consultant who works with brands on content marketing, product messaging, and social media marketing. Formerly, Dennis led the content marketing function at DNN Software. Dennis curates an email newsletter called Content Corner and publishes marketing-related content on Medium.

You can also catch Dennis at this years CMWorld as he will be hosting a breakout session. Or join the crowd following him on Twitter: @dshiao.

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