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Interview with the Co-Founder of WP Courseware and S3 Media Maestro, Ben Arellano

Updated on December 3, 2020

10 Min Read

This is a great honor for us today! We have invited Ben to our interview series and got the chance to ask him a few interesting questions.

He is the Co-Founder of Fly Plugins, the company behind WP Courseware and S3 Media Maestro. Other than that, he is a WordPress pro, course creator, YouTuber, and most importantly a great entrepreneur.

Cloudways: Thank you for joining us today, Ben! Let’s start with the introductions. How did you start your professional career?

Ben: I graduated in 2002 with a B.A. in business with a specialty in computer systems. It was sort of like an M.I.S. or I.T. degree. I graduated just after the 911 tragedy and the economy was on a downturn which made the job market a bit scarce. The best I could do was find a desktop support job at a local mining company. Eventually, I worked my way up and became proficient at software automation. By 2012 I was a Desktop Engineer at a local municipality, but it was around 2009 that I began to have entrepreneurial desires.

Over the course of the next 3 years, I tried various side hustles like web development, web hosting, and even affiliate marketing. I had the privilege of meeting Nate Johnson who is now my business partner. We met in an online forum that was associated with an online course teaching people how to do affiliate marketing by building niche websites. We hit it off rather quickly, sharing ideas and secrets.

We ended up connecting with two other individuals and we began to have weekly mastermind meetings. Eventually, all four of us decided to start a business teaching others how to make money online. We spent hundreds of hours developing a video course showing people in a step-by-step process on how to earn money online. The one thing we didn’t consider was that we were relying ONLY on teaching people how to gain ranking with Google via SEO. The problem with that is that Google is ever changing, it’s a moving target. The other problem was that we were teaching others how to rank by using blog networks, creating short articles linking back to your niche site. We even taught people how to take those short articles and rephrase them so they could basically use the same article to which Google wouldn’t be able to tell the difference.

Many would say that these were blackhat methods for ranking a website, and they would be correct in saying so. We launched our course, but low and behold, Google made some major changes to the ranking algorithm that basically cut our legs from under us. Google was on to these black hat methods. There were thousands of websites that were making money hand over fist with affiliate marketing that literally got deranked overnight. This also meant that the course we spent so much time on was irrelevant and outdated. We learned a few lessons from that experience, however, the experience wasn’t a complete waste.

Cloudways: You are the Co-founder of Fly Plugins, we would love to know the story behind this and how you ended up creating WP Courseware and S3 Media Maestro? 

Ben: When we created the online course teaching others how to make money online I was heavily involved in building the website. At that time, there was no solution to create an online course with WordPress. We basically created a dashboard page with a bunch of buttons that linked to categories which we called modules. Then the posts within the categories were the lessons/units. Basically, we sort of hacked a course together with native WordPress functionality, however, it was far from an online course. As I already mentioned we failed in that endeavor.

However, Nate and I stayed in constant communication and we thought that making a WordPress plugin to deliver an online course might have some promise. Afterall, there were premium plugins like WishList Member that seemed to be popular and in demand. In fact we had paid for a WishList Member for the website that we’d built because we wanted the online course behind a membership wall. We decided to pitch in some money and hire a developer to build out a WordPress plugin. We’d created a project scope and sent an NDA to a developer in the U.K. WP Courseware was born. Our developer even developed a licensing plugin so that we could sell the plugin with a license and deliver updates through the native WordPress update function. We launched WP Courseware in September of 2012.

When we’d developed our online course, one of the things that we were worried about was the possibility that people could directly link to our videos or even worse post the URL to the videos in forums. We wanted a way to protect the videos from internet thieves. We’d looked into many different solutions, but there was nothing available for WordPress. That idea stuck with us and gave us the idea for S3 Media Maestro. S3 Media Maestro works hand in hand with AWS to create expiring URLs to prevent hotlinking directly to the video, audio, or downloadable content. We launched S3 Media Maestro in early 2013.

Cloudways: WP Courseware has a significant market share. What makes it unique and what features give it a competitive edge?

Ben: With WP Courseware, we had an opportunity that many people look for which is being first to market with a product. There were no L.M.S. solutions for WordPress at the time of launch. We didn’t plan that, in fact, we weren’t even sure if WP Courseware would be successful. It’s always a risk when you are first to market, but the potential benefit is being first to market. WP Courseware was launched as a WSO on the Warrior Forum for $20. We were ecstatic that we even had one sale.

The first two years we focused on our customers that would communicate to us via our support desk. We listened to the issues and even had the privilege of receiving feature requests. Nate and I took all profits and dumped it back into development. We were putting out new features every one to two months. This gave us momentum.

Another thing that gave us good momentum was creating integrations with other plugins. We quickly integrated with three membership plugins and a couple of ecommerce plugins. This opened the door for solopreneurs, entrepreneurs, and internet marketers looking to build and sell online courses.

Aside from that, we’ve just been steady with adding new features and providing excellent customer support. I feel that our customers give us so much value because of the feedback and feature requests. We LOVE our customers!

Cloudways: You’ve been in the LMS industry for more than 8 years. What was the most significant challenge you’ve ever faced and how you’ve overcome it?

Ben: There have been many challenges for Nate and myself. First off we’ve never owned and operated a WordPress plugin business. We had to figure out how to distribute, license, and support a plugin. Since neither one of us are coders, we had to quickly learn the basics of PHP, HTML, and CSS. In the beginning, support was the biggest challenge. Since we are bootstrapped we have done everything from product design, product distribution, marketing, and support. As time went on marketing became a huge hurdle. In all transparency, it’s likely still our biggest weakness.

However, the biggest challenge we faced was in 2014 when we were at a breaking point. We had initially launched both plugins with lifetime licenses. What that means is those customers would receive updates and support for the lifetime of the product. This obviously isn’t sustainable from a business standpoint. We had to quickly pivot into a subscription model. However, this meant that our home grown licensing system would need an overhaul as well. This was a HUGE project, but we knew we had to get it done.

Around that time we’d connected with Pippin Williamson from Easy Digital Downloads. It turned out that he was in the process of developing a recurring plugin extension for Easy Digital Downloads and it was also compatible with the Software Licensing plugin. We were very intrigued because this meant we just needed to purchase 2 plugins that would allow us to change our entire business model. This also meant that we had to migrate and grandfather in the customers that had purchased the lifetime license.

Pippin and his team were instrumental in helping us make the change. It took a couple months to get all the bugs ironed out, but we learned more that we’d ever wanted to learn about PayPal and subscription transactions. We were finally in a subscription model and we knew that one year later we’d begin to reap the benefits. It’s likely the most pivotal point in our business because the recurring income allows us to continue in development, support, and even dabble in new products.

Cloudways: I have noticed you have created a lot of content on YouTube. How do you juggle multiple roles and businesses without getting overwhelmed?

Ben: That’s a great question! Nate and I are very much complimentary business partners. He is good with numbers and writing content. He handles most of the business side of things along with putting out some amazing content on our blog as well as social media. On the flipside, I handle a lot of the product development, testing, support, and documentation. We do have support staff that handles about 90% of the issues, however, if there are actual bugs they get escalated to me. Sometimes I can fix them, but if not we forward to our development team. Having a support staff and development team are the heart of the business, and without them, both Nate and I wouldn’t have time for things like YouTube videos, social media posts, and blog posts.

Cloudways: Most of the entrepreneurs are avid book readers. Which books you would recommend to our readers, and why?

Ben: I love Tim Farris’s 4 hour work week. It’s one of the first books I read on my journey as an entrepreneur. There are still quite a bit of relevant topics in that book. Plus I have a background in automation, so working efficiently is very important to me. I also like Atomic Habits by James clear, Miracle Morning by Hal Elrod, and Essentialism by Greg McKeown. All these books are somewhat related talking about building good habits, doing more with less, and working efficiently.

Cloudways: The large segment of the web hosting industry revolves around WordPress. What type of hosting do you think is the best for WordPress course creators? What are your thoughts on managed WordPress hosting?

Ben: I think managed WordPress solutions are great. These platforms are engineered and optimized specifically for WordPress and the support staff is WordPress savvy which makes for a good overall experience. I think one of the greatest features typically offered is a staging site. Most managed solutions also offer backup and caching. Most of my past clients have been businesses or churches and therefore I typically recommend managed WordPress solutions. It just makes sense that these companies won’t have much to worry about other than the content of their site. There are many of the, what I like to call “coffee hosting companies” that I see people drawn toward. In other words hosting companies that charge what you’d normally pay for a cup of coffee which is essentially shared hosting. Obviously these individuals are only looking at the price tag because they likely don’t have a lot of startup money. But my response to these individuals is  that a website is an investment and therefore you want to treat it as such which means they shouldn’t skimp on hosting. It’s basically a piece of real estate on the internet. Most hosting companies will market 99% up time and a bunch of fancy, shiny features, however, the most important thing to look at is speed and you simply won’t get that on shared hosting. The number of websites that the “coffee cup hosting” companies place on one server is ridiculous causing slow load times. Many of the managed hosting companies have a good balance of sites per server, and more importantly, use caching to help with speed.

I feel that WordPress course creators would be a perfect fit for managed hosting because of all the WordPress specific features. Since managed hosting takes care of many maintenance tasks and website management type duties, it really allows the end user to focus on their content which is essentially their business.

Cloudways: What are the tips and techniques you would suggest to WordPress beginners? Can you also recommend your favorite themes and plugins?

Ben: The WordPress community is an awesome community full of experts and people who have built dozens of websites with WordPress. There are many blogs like WP Beginner or YouTube channels like WPLearningLab that have great tutorials for beginners. I know things are a sort of abnormal at this time with the current pandemic, however, WordPress meetup groups are an awesome place to go to learn about WordPress and network with other developers or business owners. WordCamps are always a great way to learn and network as well. I know in my state of Arizona we have a pretty big WordPress community with Meetup groups and Slack channels which really keeps you plugged into the community. My advice is to jump in head first. I think you will find that most WordPressers are pretty easy to get along with and not judgemental when it comes to WordPress rookies.

As far as favorite themes and plugins are concerned, there are quite a few that I like to use. It really depends on the application. Custom built themes are really the way to go because you build what you need and you won’t get all the overhead functionality that consumes bandwidth and sacrifices speed. However, there is another side to that coin. Some people either can’t afford to build custom or if they can afford it, they likely can’t afford to have someone on retainer to keep it maintained. In those instances, I will likely recommend building a site with a page builder like BeaverBuilder or Elementor. You can train someone how to maintain a site, add new pages, and customize the headers and footers.

When it comes to plugins there are a lot of freemium plugins that are really great. For ecommerce sites, you have both WooCommerce and Easy Digital Downloads. Ninja Forms is a great free option for creating forms. UpdraftPlus WordPress Backup Plugin is also a free plugin that will backup your WordPress website. For security you have Sucuri and WordFence, both of these are free. GiveWP is a great option for accepting donations and it’s also free. Obviously, the freemium plugins all have limited functionality in hopes of upselling you to a premium version. However, most of these plugins will cover your needs without having to upgrade to a premium version.

For premium plugins, I highly recommend WP Courseware for creating and selling online courses. Of course, I am a little biased. There are some really great options for membership plugins, MemberPress, Restrict Content Pro, and WishList Member are among my favorites. S3 Media Maestro is a great option for protecting and serving up fast video hosted on AWS S3.

Cloudways: Who would you like to be featured next in our interview series?

Ben: I would love to see Nate featured in the next series. Nate is a great friend and business partner. People find it pretty interesting that we started a business together having never physically met. In fact, it wasn’t until about 2 years into our business that we finally met. We work well together, and our talents compliment each other and I’m very thankful for Nate.

Cloudways: Would you like to share an image of your workstation for our readers? That would be all! Thank you once again, Ben.

Ben: Thank you for allowing me to share a little bit about Fly Plugins with your readers.

ben arellano workstation

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Sajjad Shahid

Sajjad is an Ecommerce Community Manager at Cloudways. He loves helping out Ecommerce store owners, merchants and marketers in establishing their businesses and startups. Sajjad enjoys playing table tennis and cricket over the weekend.

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