Shawn will be joining us for the Building a Membership Site session, which you can watch LIVE on March 29. He’ll be teaching us the lessons he’s learned from running a wildly successful membership site over the past 5 years and, in particular, the things he wished he had known before starting.

Where can we find you on the internet?

I’m nearly always “on” via Twitter @leftlane, but you can also find me on Facebook or Google+. And I blog infrequently at ShawnHesketh.com.

You can follow @WP101 on Twitter as well, in addition to its own Facebook and Google+ pages.

Oh, and I’m always open to helpful pull requests for the WP101 Plugin at: https://github.com/leftlane/wp101plugin

When and how did you get started with WordPress?

I started designing websites in 1994, using WYSIWYG apps like Adobe Pagemill. As my skills and the complexity of my clients’ sites increased, I migrated to more powerful apps like Adobe GoLive and Dreamweaver. But by the mid-2000s, clients began to request the ability to edit their own content, using their web browsers, and after attempting to learn several CMS systems, I was relieved to discover WordPress 2.3 in late 2007.

Compared to Joomla, Drupal, and Expression Engine, I found the WordPress UI to be super-intuitive, and thankfully, so did my clients. So I began recommending WordPress for nearly all my web design projects, and with very few exceptions, I’ve never looked back.

What resources do you turn to when you want to learn something new?

I think I learn about most WordPress resources via Twitter, and thanks to the many talented WordPress developers who are willing to share their discoveries and hacks, it’s a gold mine of learning. But I also subscribe to  Post Status, WP Tavern, and Torque, which is where I often hear about new WordPress products and services.

What is your favorite WordPress feature/aspect?

Honestly, the best “feature” of WordPress is actually the community itself. Like so many others, I turn to Google whenever I’m stumped, and I’m surprised how often I land on tutorials by the über-talented Carrie Dils, or Bill Erickson. I’m grateful for the help that’s readily shared by others within the WordPress community, and I’d be lost without their help!

But I think my favorite aspect of WordPress itself is simply its extensibility. I can’t remember the last project I worked on that didn’t make use of at least one Custom Post Type, and these days, there just isn’t much that you can’t build within WordPress.

What is one piece of advice you have for someone building a membership site?

Assuming you’ve already validated your idea for the membership site in the first place, my top piece of advice is to give careful consideration to the platform on which you will build your site. Will it be around for the long-haul? What payment gateway(s) does it support?

The most challenging thing we’re currently dealing with is migrating from older membership plugins that are no longer being actively developed, and the fact that we’re stuck with thousands of recurring subscription profiles in PayPal. Migrating to a new membership plugin now requires some tricky custom coding, since all those PayPal IPN notifications will break in the process, requiring us to re-invite all our members to re-subscribe on the new system. Don’t get stuck like we did!

Read everything my friend Chris Lema’s written about  membership sites and make an informed choice that will serve you and your members for years to come. I’m also blogging about the lessons I’ve learned along the way, in hopes of helping others avoid some of the mistakes I made along the way.

But even more important, never lose sight of the fact that it’s all about people. Whether you’re building a membership site around a hobby, shared interest, or how to build a successful online business, ensure that every piece of content you create and every single interaction with your members is helping you build long-lasting connections and relationships that will encourage, empower, and enable folks to accomplish their own goals. In the end, it’s all about them… not you!

What advice do you have for others looking to become WordPress experts?

In my experience, one of the best ways to become more proficient in WordPress is to start answering questions for others. Often, their questions will drive you to look for answers you might not otherwise have come across on your own. Whether it’s answering questions for your own clients, at your local WordPress Meetup group, or helping people in the  WordPress.org Support Forums, nothing else will stretch your own knowledge quicker!

You may not consider yourself an expert, but remember… wherever you are with regard to your own WordPress skills, there’s someone else who could benefit from you’ve learned.

What is one interesting non-WordPress-related fact about yourself?

If you follow me for any amount of time, you’ll quickly learn that I’m a bit of a cigar aficionado, and I’m always down for a nice cigar and a glass of Scotch with a late-night conversation. But many people don’t know that I’m also a huge sports car enthusiast, having raced a Mazda MX5 for years in our local sports car clubs. We also watch just about every Formula 1 or IndyCar race on TV, and we try to attend almost any race within a day’s drive. If it goes fast, I’m probably a fan!