Interview with master content creator Lee Jackson #wp20

Lee Jackson is a content creator, speaker and event organiser, responsible for the awesome trailblazer.fm podcast for web agencies, the WordPress agency conference ‘Agency Transformation Live‘, his own agency called ‘Event Engine‘ and much more WordPress-related goodness.

He’s also one of the nicest guys you’ll meet.

Lee was kind enough to answer some questions about his experiences with WordPress, along with some really useful tips and advice for aspiring content creators.

Can you tell me a bit about your history with WordPress and how you got started with it?

I had been experimenting with many CMS platforms over the years, including Typo3, Drupal, Mambo, Dixit and b2/cafelog (which was forked and became WordPress).

Dixit stuck for a while as I created company sites with pages etc, and I would use a blogging platform for my personal projects.

Not long after WordPress appeared I installed it and to be honest it was a battle between Drupal and WordPress then for a few years as I tried to figure which one I was going to settle on.

It was only really when I was testing the Alpha and BETA of WordPress 3.0 that I finally embraced it for our agency full time.

I had been playing with the multisite plugin for WordPress 2.X but realised with 3.0 it was going to be baked in. I also realised that post types would completely revolutionise how I organise content for clients.

This quickly birthed our first product in the events space whilst 3.0 was still in BETA. Once 3.0 was released, we were ready to start selling our custom CMS in the events industry.

Drupal and all the others were now history. I was hooked.

Why do you think WordPress has become the dominant tool for building and managing websites?

From the beginning it has had a simple user interface which makes it easy to adopt, and the community that has grown around it has been solid.

Everyone is open to sharing their experiences, and will help each other out. You feel confident that if you don’t know the answer, someone will, and they will be willing to help.

I don’t know any other community like that!

What is Trailblazer.fm and what inspired you to launch it?

WordPress was the first reason I started the podcast. We called it WP Innovator and we focused at first on WordPress itself. We looked at plugins, and interviewed plugin creators.

But it became apparent that whilst WordPress was an awesome tool, the core community listening were freelancers and agency owners that wanted to grow their businesses.

So it didn’t take long for us to start interviewing our peers, and discovering how they built their agencies, what worked and what didn’t. The podcast has grown from there, and we still do honour WordPress regularly which was our springboard.

For example last year we released 13 episodes for Halloween entitled, WordPress tools to try before you die! 

Is there anything you’d do differently based on what you’ve learned since launch?

Tell myself it’s OK to slow down, and not release so much content. I got carried away thinking I had to keep maintaining a heavy content schedule in order to remain relevant and grow the audience.

Was there ever a ‘eureka’ moment when you realised the podcast was really taking off?

Probably when I launched my paid membership programme and we had a huge take up. However, I eventually had to close that down because I continued to over deliver on content and hit burnout.

This was a sign that taking off is great BUT, slow and steady wins the race. Year’s later we’re still going, I release episodes seasonally and take regular time off, and yet the podcast can still fill a room of legends when we run an event.

How do you approach content ideation and creation for Trailblazer.fm and what kind of content do you think resonates the most with your audience?

I run an agency called Event Engine. So I create content based on my days. What have I experienced? What have I learned? What am I battling? Sometimes I hit an issue in my agency I can’t solve, so I will bring on a guest to the podcast to help us solve it. 

Essentially, the podcast is a reflection of my daily struggles and successes, therefore if I’m experiencing it, I am sure others are.

Of course since the brand has grown, we now get many emails asking for particular topics to be covered and I do try and cover as much as possible.

How do you see Trailblazer.fm evolving in the future?

I am slowly adding video to what I do, and would like to develop my skills in presenting as I find a new audience on YouTube. It’s a LOT harder than podcast audio, so I’ve had quite a few failures along the way. But going to keep trying 🙂

It can be intimidating trying to enter a well established community like WordPress. What advice would you give to anyone who wants to launch a newsletter/blog/podcast/community/event etc. about WordPress?

We all learn from different people. There are folks in the WordPress industry that listen to me, and just don’t get me.

That’s awesome because they find someone else to listen to, or to connect with.

Frankly there are not enough folks out there doing this, we need more podcasts, YouTube channels, blogs etc.

People learn from people, and they learn from people the resonate with. YOU might be that person they resonate with, so get started :).

What are your thoughts on the future of WordPress, and how do you see the platform evolving over the next few years?

I see it being a framework to springboard more and more microsass products. Gutenberg, love it or hate it, has introduced many of us to a new way of working and developing and I am very excited to see where all this will lead.

I do worry about the politicisation of WordPress, and the hate that polarised folks sling at each other.

However I think that the day to day users, designers and developers will have the most influence on the direction it takes.