RS022: Changing Lives, One Plugin at a Time with Pippin Williamson

Rogue Startups
Rogue Startups
RS022: Changing Lives, One Plugin at a Time with Pippin Williamson

Welcome to Episode 22 of the Rogue Startups Podcast.  Today Dave and I are excited to catch up with Pippin Williamson.  Pippin is the founder of and creator of Easy Digital Downloads, Restrict Content Pro, and AffiliateWP, to name a few.  In the world of WordPress Pippin is a giant.

In the episode we dig into a lot of the aspects of developing plugins for WordPress.  Open source platforms like WordPress come with a lot of interesting dynamics that don’t exist with either single download software tools or SAAS apps.  This can be a huge advantage, as the pool of contributors is enormous in the case of WP, but it also creates the need to accommodate a wider range of use cases, backwards compatibility, and install instances.

Pippin digs into how their support system is all based in HelpScout (until SupportVine comes out!).  HelpScout is almost entirely email based, which allows for easily assigning, tagging, creating analytics around support issues, and even doing support on mobile devices.

Pippin is also just getting into the world of live chat support, which could be a real advantage in the turnaround time for customers, and taking a percentage of tickets out of the queue instead of clogging up the main support channels with easy wins.  Live chat may actually turn into an avenue to bridge the gap with warm leads that might have some final questions before making purchasing decisions.  If that’s the case then it’s an easy decision to keep the live chat going.

PippinsPlugins was the place where Pippin originally started writing tutorials and doing screencasts several years ago.  At this point it is a fun side project where he can share his new ideas, lessons, and best practices for other WordPress developers.  One advantage of having such a large body of work and devoted following is that if needed, or if he wanted, Pippin knows he could turn this website into a full time job and allow it to be his primary source of income.

One of the challenges of being an entrepreneur and a solo founder is the constant demand on your time and attention.  There are no weeks off, extravagant vacations, and mental breaks from the work.  As we develop as entrepreneurs, making the time to create that balance in our lives becomes paramount.

Pippin’s team has grown organically, almost entirely from unpaid contributors who eventually made themselves known to the projects, and eventually coming on to the team as full time employees.  One of these has a particularly inspiring story.  If you’re wondering if you have what it takes to succeed in this business, go read that story.  You won’t regret it, I assure you.

We wrap up by discussing some of the business modeling in WordPress based businesses.  Each of Pippin’s products are sold under different structures, and he suggests first taking a look at your product and your business and think about how customers would want to buy those products.  Don’t just model your business and pricing structure after other popular products out there.  It may not be the best for you.

Pippin is the cohost of the ApplyFilters Podcast with Brad Touesnard.  If you’re looking to learn more about building a business centered around the world of WordPress solutions, check it out.  It’s a great listen.

If you’d like to check out more about Pippin and his products, head over to or hit him up on Twitter @PippinsPlugins

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