Episode 171

Learning, Leadership, and Entrepreneurship with Pippin Williamson of AffiliateWP

We discuss learning, leadership, and entrepreneurship with Pippin Williamson of Affiliate WP in this episode of LMScast. Chris Badgett of LifterLMS and Pippin talk about affiliate marketing for your product or service and what it takes to create a strong brand. Pippin shares his story from growing up surrounded by nature to entering the software development and WordPress space.

Pippin grew up with four siblings and his parents on an apple orchard in the middle of central Kansas, about 30 minutes from the nearest town. He had a very nature-oriented childhood and a technology-oriented family, so Pippin developed a love for the outdoors and a passion for software development.

Pippin has done a lot of interesting things as an entrepreneur in the WordPress space. He created many plugins for WordPress, including AffiliateWP, Easy Digital Downloads, Restrict Content Pro, Sugar Event Calendar, Love It Pro for WordPress, and many more.

Competition is the driver for creativity and progress. Chris and Pippin discuss competition and how niching down to a particular set of people with your product is key to its success. Pippin talks about how he builds products to serve a specific purpose, and how he would rather send customers to his competitors rather than make the platform do something that it was not meant to do, because those customers shouldn’t be using his platform in the first place.

Affiliate programs can be complicated to set up and run for your product or service. Chris and Pippin talk about the major pain points when setting up an affiliate program for your product, and how you can go about avoiding those obstacles.

Affiliates have a significant impact on your brand, so it is important to vet them carefully, lay out specific guidelines, and make sure they provide value to your brand and image with your customers.

‘Build it and they will come’ is a popular saying in content creation, but unless you have a really stellar brand or product, this is not going to be the case. It is important to educate your customers and affiliates on what your product or service is and how they can use it.

Entrepreneurs often suffer from overload with work, and it is important to constantly re-evaluate what is important to your business and your success. Often you will find projects in your business that are not enjoyable and that are not making you any money. When you find these resource wasters, you can cease working on those activities and repurpose the content you have. Chris and Pippin talk about this, and Pippin shares his thought processes behind shutting down products and services he has offered.

To learn more about Pippin Williamson head over to Pippin.com and PippinsPlugins.com. Also check out the AffiliateWP plugin available for WordPress.

You can subscribe to our newsletter for updates, developments, and future episodes of LMScast. Thank you for joining us.

EPISODE TRANSCRIPT

Chris Badgett: Hello, and welcome back to another episode of LMScast. My name is Chris Badgett from LifterLMS. I’m joined by a special guest, Pippin Williamson. Pippin is somebody I look up to in the WordPress space and as an entrepreneur. He’s done a lot of interesting things for WordPress, as an entrepreneur, as a product company, as a leader of teams, and just as an all around interesting guy. We’re both twins. There’s a fun fact for you out there. I want to start by just welcoming you to the show, Pippin, and ask you about your tagline, just on your side or your blog or whatever where it says, “A nature loving farm boy that found his way into the internet and technology.” I’m kind of a nature first guy technology then the technology thing happened, but how did that happen for you?
Pippin W.: Sure. Thanks for having me on. It’s a pleasure to be here. That comes from growing up. I come from a pretty large family. There were five siblings and then my parents. We grew up on an apple orchard in the middle of Central Kansas about 20 to 30 minutes from the nearest town. We grew up, really, unschooled. We were, pretty much, free to run around the property. We had about 100 acres of woods and prairie out there. Growing up, I grew up surrounded by nature, encouraged to go out and be outside all day. I prefer to be outside all day. I ran around barefoot most of the time.
We had very just nature-oriented childhood. That has become very much part of me. Being out in nature and being connected to the natural environment is really, really important to me, but at the same time, we had a very technologically-oriented family. My dad is a software developer. We had computers in the house. As long as I can remember, we were one of the first houses in the area to get high speed broadband. We’re probably one of the first to have a dial-up connection. Then we were the first to have a fiber connection. Even though we were very nature and outdoors oriented, having an apple orchard and a little bit of farm, we were still computer people. That naturally transitioned into me turning into a software developer as well. I gained love for programming pretty early on. Maybe around 10 or 12 years old when I started programming robotics.
During college and late high school, I started transitioning into web development, building things online, which then eventually turned into business that I run today, but I still go back and try to remember the importance of being outside. Yesterday, for example, I decided I have enough for the internet and decided, “I’m going to spend the evening just splitting firewood and going back and having a goal of being completely sustainable on our own.” If I could be anywhere in the world, it would be outside in nature. Well, I’ll probably take my laptop with me.
Chris Badgett: Yeah. That’s awesome. Yeah, I really relate to that story. Just for those of you listening, unschooling, it’s actually a parenting style that I practice where our kids are homeschooled without a traditional curriculum and just lead what they’re interested in. We facilitate that as parents. It’s an emerging trend now, but it’s been around for a long time too. I’d like to get into a little bit with you, Pippin, about just that piece, how old are you right now?
Pippin W.: 28.
Chris Badgett: Pippin, some of the products he’s best known for in the WordPress space is AffiliateWP and then there’s a membership system called Restrict Content Pro and then Easy Digital Downloads. For those of you who are familiar with Lifter for sewing courses, it integrates with AffiliateWP. If you want to add an affiliate program, you can do that with Pippin’s product. We’ll get into that a little later, but before we get into the business and the technical stuff, what was it like as a … When did you start your first company? You’ve got between one and 200 WordPress plugins free and paid out there. You’re prolific. You started programming robotics at 10 years old or something like that, but how did the entrepreneurship start?
Pippin W.: That probably started maybe around when I was 14 to 15. My brother actually beat me to it. When we were about 14 and 15, I have an identical twin brother, he got, really, into 3D modeling and using an open source piece of software called, Blender 3D. He started creating a business around that before we ended high school. He was already doing that and making pretty good money for himself before we went to high school. With our inschooling experience, we were unschooled until high school and then we chose to go to public school. He did that. My dad was a freelance software developer. We had that just naturally in our family. I started it, basically, my freshman year of college where I went to the University of Kansas. I just started taking on freelance clients from building websites or anybody that would hire me. Eventually, that turned into building plugins for WordPress.
The first plugin I built, I threw it up on a website called codecanyon.net, which is a marketplace run by Envato. I sold a couple copies of it. That just got me started on building a whole lot more. I built another plugin and then I built another and I built another. I had a lot of time on my hands. I was really interested. I was having a lot of fun. I just kept building out. Eventually, it turned into a large enough revenue stream to be able to quit doing freelance work and move solely to building plugins, at which time, I really started looking into setting up as a real company as opposed to just an individual. That would have been 2012, 2013. Once I did that, then it started really growing and turning into an actual company where we have employees and other team members and things like that over the next couple of years. Where we are today, we have a team of 13 with a few contractors.
Chris Badgett: How did you pick your niches or your niche? Again, it looks like there’s a common eCommerce thread here.
Pippin W.: All of our three main products, which are all eCommerce based memberships, digital products, and affiliate marketing all started through solving my own problems, solving my own pain points. Originally, Restrict Content Pro is the first. I wanted to run a membership site. I was writing development tutorials, teaching people how to write plugins and I wanted to have a membership site to lock down access to the tutorials to paid subscribers. I didn’t like the membership plugins that I found, so I built my own. Eventually, I wanted to move the plugins I was selling off CodeCanyon. I didn’t like the options for selling plugins on my own site, so I built my own. I was then running a successful eCommerce store through my platforms. I wanted to run an affiliate program. I didn’t like the options. I built my own.
Chris Badgett: That’s really cool. Scratching your own itch. Were you, at all, intimidated by, let’s say, going up against an established leader and the WordPress eCommerce space like WooCommerce? When you did Easy Digital Downloads, you just went for it and it sounds like you were going to go for it anyways because you wanted to build a better mouse trap to solve your exact problems. Did you even care for a second about the competition?
Pippin W.: No, I didn’t, really. Obviously, we know it was there. We don’t pay attention to it, but we also realize, look, competition is good. Competition breeds creativity. Competition, as long as you’re not going out trying to sabotage each other, it breeds collaboration. Well, we just solve pain points that are not on their radar or that are not their focus. They just solve pain points on our work. It comes a nice ecosystem where I don’t want every customer that’s out there because we want to build a product that is built to serve specific purposes. If a customer comes to us and our body didn’t serve their purpose, they shouldn’t be using our platform. We would rather send them to a competitor that does solve their problem, then try to make our system work for them in a way it’s not mentioning.
Chris Badgett: Yeah. That’s a great way to talk about it. Easy Digital Downloads, even in the name of the business, you’re differentiating exactly what it’s for. It’s for downloads.
Pippin W.: Right.
Chris Badgett: It’s not for everything store.
Pippin W.: Right.
Chris Badgett: I want to get into the affiliate area a little bit. I do the same thing. I scratch my own itch. Lifter started as a reaction to me trying a lot of course, membership, solutions, and just wanting something different. We ended up charting our own path. Other people have found that useful that’s why we have a business today that’s growing and doing great. One of my very first site that I built on a WordPress LMS, I’m actually in a process, finally, of moving it over to LifterLMS. One of the things I can’t wait to get it over to Lifter for besides … there’s a lot of reasons, but one of it is-
Pippin W.: Eating your own dog food is good.
Chris Badgett: Yeah, it is good. The affiliate system I have attached to it, it doesn’t work as well as it should. It’s had issues. I’m going to be, very soon, picking up my own copy of AffiliateWP, relaunching the affiliate program. Affiliate has actually been a big part of that project in terms of, I don’t know, a portion of the revenue. In my experience, and I’ve also just seen a lot of sites and been around as agency of platforms and have an affiliate program, I’m curious, in your experience, what percentage of sales do you see coming through the affiliate channel? In my experience, I’ve seen between 10 and 40 percent. It just depends but where do you-
Pippin W.: It’s actually funny that you mentioned that because that’s one of the reporting metrics that we don’t have built out very well with AffiliateWP, but it’s one of our biggest needs. It’s one of the things that we’ve been looking at trying to get built out. We don’t want store owners to have to guesstimate. We’d much rather just give them a number that says, “33% of your sales come through the affiliate site. That’s what we would like to do.” It becomes a little bit challenging because we integrate with so many different platforms. Obviously, we integrate with LifterLMS, as you just mentioned, but then, EDD, WooCommerce, those are just a couple of the top ones, but we have almost 30 different integrations. Then you start building out like you want to build and do that for everybody. Anyway, we have, I believe the last number that we looked at is somewhere around 15 to 20%.
Chris Badgett: Cool. Yeah. That sounds about what I’d expect. What advice do you have, not necessarily, for software companies but in general, for people to recruit affiliates? What do you recommend?
Pippin W.: Well, I think the biggest point of failure we see in people implementing their affiliate programs is them installing the plugin, turning it on and just like letting it sit, assuming that it’s going to magically make them money. Well, it’s not a set and forget system. Yes, the system itself is set it and forget it in terms of doesn’t function, but you actually need to be proactive in encouraging people to join your affiliate program and actually, helping educate them on your product or do you have new items coming out, educate your affiliate based on that. I think that the biggest thing, and this is something that I will be perfectly honest with you, we have not done well at X, but we recognized it. We have been working a lot this year to actually improve this. You just need to communicate with your affiliates. You need to give them tips. You need to give them resources. You need to give them heads up.
If you’re going to have promotional sale coming up, give your affiliates a heads up, so that if they want to put out material to help advertise it, they can do that. Don’t say, “Hey, today, for the next three days, we’re doing a sale. Go ahead and let people know.” Great. Those affiliates, one of them was on vacation, one of them was already busy for two days. If you don’t give them a heads up, you’ve lost any traffic that they might have been able to give you. You need to communicate with them. I think that’s the biggest failing point that we see most of the time is people just not communicating … Well, to their existing affiliates but also communicating to new affiliates and actually reaching out to people an encouraging them to join. That’s probably the number one thing that I would recommend above anything else.
You can figure out what percentage of a commission you’d give affiliates. You can figure out how often you pay them. You can figure out all of those other stuff, but if you’re not communicating or you’re not practically reaching out to them, it’s not going to work to anybody.
Chris Badgett: Yeah. That’s a super good point. Also, once you have them, that’s one thing but going after them, if you build it, they will come and tell. You’ve got to go recruit. Go find somebody that has your audience that’s not a direct competitor.
Pippin W.: Just build it and they will come can work every now and then. If you have a super stellar brand or you have a super stellar product or something like that and you have a proven track record, but you … You might get a lot of people but you may not get through ones that you want. Keep in mind that one really good affiliate would probably worth dozens or hundreds of mediocre ones.
Chris Badgett: Yeah. I think, maybe, we can just give out three tips. I’ll do one while you think about it …
Pippin W.: That’s great.
Chris Badgett: … and then you can come up with two, but for one of my educations sites that I have an affiliate program for, one of the ways I get affiliates is, I’m in a very specific hyper focused niche. If you Google the niche name plus affiliate program, it’s the number one search result on Google. I wrote a blog post to introduce the affiliate programs specifically targeting, “Hey, this niche has an affiliate program. Here it is.” Basically, if you’re a publisher, a blogger, or you’re looking to monetize your site and you teach them this topic, for this one, it happens to be a sub niche of organic gardening called, permaculture, you’re going to find our affiliate program because there’s not that many out there affiliate programs for that niche per se. One tip is, just introduce it, write a bunch of content. Even just one nice blog post about it talking about your niche because there’s so many bloggers out there who write about that stuff looking to monetize their content.
Pippin W.: Yeah. I wrote a blog post and they first opened the affiliate program for Easy Digital Downloads. I wrote a blog post on my site, basically saying, “Hey, they feel the program is up. You’re welcome to come join.” We then, maybe six, nine months after that we closed it down. Now, we have since reopened it, but immediately after closing it out, I didn’t realize that that was actually getting a ton of traffic because I would get emails every single week like “Hey, I can’t join. What’s up? We’re going to join?” It’s like “Oh, I’m able to join, it works.” I think my tip would be, yes, you want to invite people to join because (1) how are people going to know about it if you don’t, but simultaneously, be careful with who you let in. Don’t just let anybody in just because I said, “Hey, I’ll help promote you.”
You wanted to make sure that you’re controlling your brand and your reputation. You don’t want to have a bunch of really subpar affiliates just dropping spammy links on a bunch of random sites that had no pride or value to you and potentially, actually, harm your brand even if it’s in a minor way. Moderate them, be thoughtful on who you do let in and why you let them in. At the same time, consider why are you turning somebody down. Is it just because you don’t like them and they didn’t give you good enough application? What is it? Just think about that. Don’t just assume that everybody that applies is going to be a good affiliate.
Chris Badgett: Yeah. You already gave another tip, which was, it’s better to have one really good affiliate than … If you’re going to just do a couple things, make sure people can easily find your affiliate program, invest and maintain the quality. There’s all kinds of shady affiliate activity out there and that’s going to hurt your brand. If you have limited time and resources, go for one really good affiliate. It’s better than 100 ones that aren’t falling.
Pippin W.: Absolutely. For each of our brands, we’ve got two or three top affiliates. They easily send three to 20 times as much traffic as anybody else. Not just traffic but actual conversions. It’s not that they converted it in actual sales.
Chris Badgett: Yeah. If you’re new to affiliate marketing, there’s a concept called a super affiliate. What you want is a super affiliate, ideally or a couple of them or several of them. Well, let’s switch gears in the conversation a little bit to just your entrepreneurial side. I know some people look at you and they’re like “I want to make sure I’m supporting my kids if they want to become entrepreneurial.” What tips do you have for somebody looking to raise entrepreneurial kids or empower them to pursue that if they want to do that? What tips do you have about that?
Pippin W.: Looking back on it, one of the things that my parents did that really encouraged us … Well, first of all, it was just encouragement of, “You can do it if you want to.” That’s pretty important.
Chris Badgett: That’s enough.
Pippin W.: Yeah. Have it. It’s an option to pursue anything you want. Whether you succeed or fail, you have the option to pursue and do anything. Just being open and acknowledging that, yes, in the digital age, especially that we can even if we fail, we can try. I think that’s really important. Having a mentality that it’s okay to fail is good because … The Silicon Valley Model tends to celebrate failure and I think, maybe, too much, but at the same time, we need to recognize where did that come from and it’s acknowledging that it’s okay to fail. It’s better to try and fail but to not try at all. It doesn’t mean that it’s a celebration of a failure if you fail, but it’s still okay to do that. I think those are some of the big ones.
Honestly, everybody is in a different position but some people have a lot more flexibility to try and fail because they’re more financially stable than others or maybe they have whatever kind of resources is it that they have. What your resources are really going to determine whether how much flexibility you have, but overall, it’s I think more than anything. The mental mindset is really important of just saying, “Yes, I am going to try.”
Chris Badgett: Yeah. That’s good stuff. I think this is related to this in some ways. We breezed by it earlier that you had made somewhere between 100 and 200 plugins. You don’t have one product. You have three main products plus …
Pippin W.: Three main links to the table.
Chris Badgett: … you have started a brewery. Is that right?
Pippin W.: Working on it.
Chris Badgett: If someone call that prolific, how much of it that is personality? How much of that is just you as an entrepreneur? What’s going on with your prolificness?
Pippin W.: A lot of it is my personality. I’ve always-
Chris Badgett: You’re a doer.
Pippin W.: I’m very much a doer. I’ve always had a lot of projects going simultaneously. As a kid, in high school, in college, et cetera, I’ve always had lots of names going on. I think the freedom to be bored is an amazing gift. However, if you are bored, my question is why. Because if you’re bored, then obviously, you’re not doing enough. That’s the way that I’ve always looked at my own mentality. If I find myself sitting around and bored suddenly, and to me … In the evening, I can go to bed and watch Netflix for two hours. To me, that is very different than being bored and watching Netflix as a result of being bored. In my mind, if I’m bored, it’s because I don’t have enough to do. I have not been bored in 15 years at least. If I have open time, if I’m going to do something and whatever that is. When I was originally building the WordPress, it was well. If I have the time to be bored, I’m going to build another plugin or I’m going to enhance a plugin.
Right now, if I have the luxury of being bored, it’s because I’m going to take that time and I’m going to build something else. Right now, I’m building a brewery. At home, if I start building a project at home, whether it’s something in the workshop or I’m building a little wood shop right now, that is really just a mentality, I think. I think that is something that most business owners, especially those that have a bit more entrepreneurial spirit, probably are familiar with. Just this idea that you’re always doing something. You’re always pushing on something. Yes, there is a drive to succeed, there’s a drive to do more, but it’s also, it’s curiosity. I want to go explore new things and have fun doing it. If I decide that it’s not for me after a year, that’s fine. I had a lot of fun doing it. Hopefully, I don’t bankrupt myself doing it.
Chris Badgett: Yeah. That’s really good. I share that where actually I’m never bored. I can’t remember the last time I was bored. If I find myself alone with nothing to do or walking in the woods, not work, great, now, I have time to work on these problems in my head.
Pippin W.: Yeah. Absolutely.
Chris Badgett: I don’t experience boredom either. That’s an interesting way to-
Pippin W.: I don’t think any successful business owner entrepreneur experiences boredom. They’ve experienced boredom. Absolutely. I can remember when I was bored last, but I remember changing that and say, “I’m not going to be bored again. I’m not trying to be bored.” I don’t know. Maybe there’s just a different wiring in brains that … I don’t know what it is but-
Chris Badgett: Well, related to this being prolific, sometimes you shut things down. Recently, I was actually on the WP Tonic Panel podcast. One of the articles discussed was your recent article about closing your membership. I know you recently put your podcast applied filters on pause. What’s going on with those two projects? What’s your approach to maintaining focus? What’s your reasoning behind all this?
Pippin W.: There’s two things that I think are the main reason behind shutting some products down, at least for the ones that we’ve shut down recently. We’ll talk about the podcast and the memberships on plugins.com. One of them is simply, are we still having five billion? It’s a little bit of a luxury to be able to say, but I think if we’re not having fun doing it, why are we doing it? Obviously, that doesn’t always apply. There’s things that I do everyday that I don’t enjoy, but I do them because they’re necessary. If we look at something and say, “Does disabling industry [inaudible 26:11] to work on this? Does it permit any way?” If the answer is “no” and we’re not adjoining it, then why are we doing it?
The podcast, I really loved doing it, but eventually, we got over the honeymoon phase of that podcast and it started to become a little bit more mature. It was not a focus for us. It wasn’t primary focus. We decided, “Let’s pause it indefinitely.” If we want to come back to what we can, and then the memberships on Pippin’s plugins. As I mentioned earlier, that was a membership that I launched back in 2012. That is what built Restrict Content Pro, which is now one of our primary products was, I want to draw in membership so I pulled the plug and do it. I’m in that since 2012. There was a couple reasons for shutting it down; (1) I was simply not able to produce content for anyone. There was a large catalog of content that was provided to members. It wasn’t getting updated anymore. I could not justify continuing to accept payments from people if I was not going to be producing new content.
I held on to the hope that I could produce new content for a long time and kept it going, trying to get back in the producing content and eventually just decided, it’s just not going to happen because it’s not a priority or X, Y, and Z. It is not going to significantly hurt us, financially, to disable it. The best thing that I can do is to discontinue it because (1) I no longer have this battle inside of whether it’s okay to take people’s money but I’ll produce you with content, get rid of that problem and (2) relive the burden of knowing that I’m failing it, taking care of these memories. At the same time, I can do a good thing by taking all of the content that was blocked behind the membership and just open it up. There’s no reason we can do that. All of it comes down to getting better at saying no and choosing where our time is going to be spent where our focus is put. I decided that the membership and the podcast were two things that I needed to say no to because they were not, in terms of the value that I was getting from them personally, they took more even just being there than I was getting out of them.
Chris Badgett: Yeah. That’s really good stuff there. Let me ask you, also, about leadership. A lot of the course creators and membership people out there may be a one person show, a lot of them are, just like you and I were when we first started freelancing or whatever, charging or building our first products. You build a team. How big is Sam Hill’s development now?
Pippin W.: We have 13 full-time team members as well as a couple of contractors.
Chris Badgett: What were the challenges for you in transitioning to a leader? I think I’d also might be an inspiration to younger people starting businesses.
Pippin W.: Probably the biggest challenge I have is just delegation. Coming from a one man shop and coming from the doer attitude of I can do whatever I want. I can-
Chris Badgett: Get it done.
Pippin W.: Yeah. I’ll jump in. I have no problem being on the front line. It was a natural challenge for me to let go of doing certain things and delegating those out. A lot of our initial team members that came on either did complementary work to me. For example, the first people that I brought on were there to help with customer support, but I was still doing customer support. I didn’t replace myself. I just added on because I couldn’t handle all of it. I was still doing just as much as they were. Next was development. I hired a couple developers. I was doing just as much development as they were. That expanded out. More developers, more support. It took, at least, a couple of years before I had truly offloaded tasks that’s why I stopped doing it.
Today, I do very little of the development. Up until about a month ago, I still get a lot of the support. Now, I’m working on stepping out of the support site as well. My main challenge has always been delegate. I think some people might ask if it has to do with trust. I know that I can do the job well. Do I trust someone else to do the job? Well, it’s not that. I’ve never had a problem with trust, the only people that I hire or people that I trust 100% anyway. Look, if I can’t trust you with the keys to the business, why are you here? If I can’t trust you, then you shouldn’t be here. It has nothing to do with trust.
Okay. Let me give you a very specific example. I recently delegated or worked with one of my team members to take over handling fraud cases and charge disputes and things like that. We’ll have sales come through, they’ll either get disputed as fraud or somebody disputes it as, “I didn’t like it” or whatever. I have always handled those myself. I’ll go to Strife. I’m going to work on any of the disputes. I recently assigned that over to one of my team members to take over, but I’d get an email every time a dispute pops up. I inherently just dive in and start doing it. I’m like, “Whoa, wait a minute. No. Stop. I was supposed to give this over here. He is supposed to handle that. I shouldn’t do that.” I just naturally do things. I, now, have to tell myself, “No. Stop. Hold on. Somebody else is going to do it. You don’t need to do it.” That’s been an interesting transition for me.
I think this last year, the last 365 days, was when I really started to recognize the effects of that because I actually have a lot of days this last spring and summer bored in my office. Now, I say bored because it’s what I recognize is, I was sitting there trying to … I’m used to having a big long to do as if, “Here’s what I’m going to work, here’s what I’m working on today.” I started, at times, when I realized that I had nothing explicitly assigned to my to do list for that day. I’m like “I have to figure out what to do. What am I going to do? All of the stuff that I was going to work on is now taken care of.” It has been a great opportunity because then, in the same way that boredom encourage is a breeder of creativity, all of a sudden, now, I realized, “Oh, I’ve got three hours. I’m here until five o’clock before I go home. I’ve got, at least, three hours to do something. What am I going to do? Where can I just put my time?” Getting used to that has been an interesting aspect of leadership that I had not anticipated.
Chris Badgett: Yeah. That’s super interesting. I call this …
Pippin W.: I keep telling my-
Chris Badgett: … slow down to move fast. Before you jump on that fraud dispute charge back thing, you’ve got to slow down. Once you empower your team, your company starts moving faster, which then frees your capacity.
Pippin W.: Right. Absolutely. Well, that’s precisely what has happened. It took a little while to recognize that as I keep telling my team like “I hired myself out of a job.” Now, I make it a new job for myself.
Chris Badgett: Yeah. That’s really cool. Just as a side question on team, I come across this where I’ll create a job description or I’ll pull out an isolated thing like you’re talking about fraud and disputes and whatever and move that over to somebody else, how much do you focus on the job description versus the person? If you know a great person and maybe they don’t fit into the box of whatever the job title is perfectly but they have the skillsets, how do you do that because I’m sure you have a diversity?
Pippin W.: We just don’t do it.
Chris Badgett: No job title? Is that what you mean?
Pippin W.: We have no job titles.
Chris Badgett: Okay.
Pippin W.: We don’t have titles. We don’t have job descriptions. We started to think about that a little bit more this year as we’ve grown. We’re starting to get to the point where it’s a little bit more important to actually have titles for people, not to give them a role but to explain what they do to new people. For example, we brought on a new person, brought on a couple of new people to this last six months, but one of them that came on was coming in from a very different work experience was not super involved and the WordPress world was not involved with development. When she came on, it so then became important to explain, what does Chris do, what does Andrew do. Like, sure you can ask me or you can ask them but if you want to go and read about on, let’s say, your first day, you want to know who all your co-workers are even though we’re remote and you’re talking it in in slack, also, it is important to have a description of what everybody does. That was interesting. That was not something I had considered.
As we grow, we start to recognize the importance of those kinds of things for more. An example of an idea is that all of the original crew, which is four to five people, they came on after I sent them a Twitter DM and said, “Hey, want to come to work? Awesome. See you tomorrow.” Things have to formalize a little bit more as we get bigger. That’s been a little bit of challenge. When it comes to job descriptions, we don’t really do job descriptions unless we’re doing a job posting, which has only happened once or twice. Most of the people that we have have joined us organically, but everybody that we bring on is, it’s made known that they have the flexibility to do anything they want to the company. We will bring them on for a specific role or for a specific job and sure, we could get that a job description, but they have the flexibility to move within the company.
If they come in doing customer support and recognize that they really enjoy a different aspect of this thing, they have the freedom to move over there and make themselves the most valuable as they can where their skills can be put to the most use. If that means that they move from customer support to marketing or they move from customer support development, that’s great because honestly, if you’re better in that, that you are customer support, I don’t want you to be customer support anymore. Of course, I want you to, but it would be silly to not recognize where the most value is. We don’t get people set titles or job descriptions because … just because you know how to write code doesn’t mean that is your job. Your job is where you are the most valuable to the company. One of our developers is a really good data analyst. He does a lot with Google analytics, but we don’t put Google analytics at the job description. We don’t just say you’re a developer either because it becomes limited.
Chris Badgett: I love that. That’s Twittable there. Your jobs is where you contribute the most value to the company. That’s a great word of a credit. I do need to ask you one more question before we wrap up as being a leader in the WordPress community. What is your advice for end users and WordPress companies to navigate the transition with Gutenberg that’s coming? I know that’s kind of a big question, but what is … People are just trying to figure out the future and deal with change. What’s your take on this whole thing?
Pippin W.: Well, I have a bunch of different opinions on it. For end users, I think, for anybody that is actually that’s familiar with following it as an end user, be patient. Can I say something bluntly?
Chris Badgett: Sure. Yeah.
Pippin W.: Shit’s going to break.
Chris Badgett: Yeah.
Pippin W.: Shit is going to break everywhere. This is not because the core team is building something unreliable. It’s not because plugin developers build things. It’s just that there is a ton of moving parts. If we look at the overall WordPress ecosystem, there is WordPress core, there’s always plugins, there’s all these themes, there’s always platforms built on top of it. The possibility of everything just working perfectly together out of the box is just not going to happen. I would love to say let’s keep the reality, but it’s not. As Gutenberg comes around, things are going to be able to rough. Be patient. I think in the end, it will work out well and it will be beneficial to everybody once the rough edges get smoothed out.
As a product creator, one of the challenges, and so we don’t know what it’s going to look like in the end. It’s a little hard for us to prepare for it at the moment. Sure, there’s rough ideas and we could participate in development discussions. We can participate in testing, et cetera, but we’re not really sure what the final picture is going to be. We can’t tell you, “This is the way that Easy Digital Download is going to be with Gutenberg” because we don’t know. We won’t know for a while. For end users, you need to be patient but let us obviously tell people feedback, tell product creators feedback. If you have things that you rely on, plugins, themes, et cetera, let them know but yeah, be patient with them. Yeah, I hope that it works out really, really well. I think we’re going to have an interesting next year.
Chris Badgett: Yeah. In all that, there’s a leadership opportunity, there’s new businesses that can be born on the back of this change and helping people adapt or it can draw a line in the sand of, “That was then, this is now.” Any software, a major release when 2.0, 3.0, 4.0 typically has major changes like this. It’s a natural process.
Pippin W.: Yeah. Absolutely.
Chris Badgett: Awesome. Well, I want to thank you for coming on the show. Thank you for everything that you do. If you’re …
Pippin W.: It’s been my pleasure, Chris.
Chris Badgett: … listening to this or watching the video, I’d encourage you to check out especially AffiliateWP. If you want to add an affiliate program to your courses, your memberships, and then just check out all the other stuff that Pippin is up to. You can find him at pippin.com as well. Yeah, thanks so much for coming on the show. We really appreciate it. I enjoyed this conversation immensely.
Pippin W.: My pleasure.

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