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How Empowering Your People Leads to Company Success

Host Jon Penland, 

You can never scale your business if you keep being the bottleneck of your operations. Letting go of control is a common struggle most entrepreneurs face. Adii Pienaar, the founder of Cogsy, believes that the key to growing your business is to give your people space to thrive and learn. Discover more about how Adii promotes autonomy and accountability on his team, including how his company’s non-negotiable values guide its goals and operations.


44 minutes



Episode Summary

Mistakes are an inevitable part of business, and that’s the most common reason entrepreneurs are so scared to give up control and give their employees more freedom. 

But giving autonomy to your team members will make them more motivated to produce better results and share their best ideas. This, in turn, will help your company grow.

In this episode of the Reverse Engineered podcast, host Jon Penland welcomes Adii Pienaar, the founder of Cogsy. They chat about the importance of flexibility at work, why your company’s values are non-negotiable, and how to foster peer-to-peer accountability.

Key Insights:

  • Find trustworthy people in your team, and give them the space to grow. One of the most common struggles that entrepreneurs face is letting go of control over their business. But it’s essential to give your people autonomy and flexibility, if you want to see them thrive. Adii explains, “Beyond identifying who those individuals are, you have to give them the space to essentially create a feedback loop where you’re able to trust them because I think that’s the thing. I backed myself, so I trust myself, which is the mindset you’re in. So you have to find a way to trust someone else, and I don’t have to second guess them and think, ‘Oh, I can do this better.’ But to do that is a bit counter-intuitive; you have to give them the opportunity to show you, ‘Hey, this is what I can do. Hence, you can trust me and step away.'”
  • Your company’s values are non-negotiable. Every business should define its non-negotiable values. This will help employees stay on the right track. Adii says, “We’ve got a document called ‘The Vivid Vision.’ There’s a book by a gentleman named Cameron Herold by the same name. And the idea basically is that it’s a three-year plan with loads of color and context as to how you imagine your business, team, product, et cetera, to look like in three years. And a part of that is around the values — the way you think about the state of truth for you as a company and a team. And ultimately, those are the guardrails. It’s like if everyone in the team operates within those guardrails, then I don’t really care whether they zigged and zagged or walked in a straight line towards that outcome.”
  • Your work should be there to serve your life and not the other way around. If there’s one thing that Adii would like you to take from his book, it’s that your life shouldn’t revolve around your work. He explains,”I don’t like the idea of work to live or live to work. I think both of those feel very binary, firstly. Secondly, I also don’t like this idea of work-life balance. I think the idea of work-life balance proposes that you either work or you live. And I think work and our professional endeavors are just a single [part] of life. So what I tried to do within the book was to propose a different approach, where you can do these things in life — whether it’s work, some professional endeavor, or just other things — in a way that is profitable in the context of your whole life.”

Today’s Guest: Adii Pienaar, Founder of Cogsy

Prior to Cogsy, Adii was a 3x founder (WooCommerce, PublicBeta, and CM Commerce). He’s also the author of Life Profitability: The New Measure of Entrepreneurial Success.

Episode Highlights

Businesses could benefit from more sophisticated tools

“The reality is that most of the brands are stuck in spreadsheets, and a spreadsheet is a great tool for many different things. There is no way for us to completely get people out of spreadsheets, but that’s what Cogsy is trying to do. It’s trying to build an alternative to spreadsheets and, essentially, focusing on the things that make software really good.”

Financial stability allows you to take risks

“I did things that I would not recommend first-time founders do. For first-time founders, I always recommend do the customer development beforehand. Don’t believe that you can build it, and they will come. We’ve all heard that kind of cliche thrown out. With Cogsy, it was more a sense of understanding that there is a problem and then being able to say, ‘You know what? I’ve been successful enough to have diversified, at least my financial interests, which means that I can be slightly riskier.'”

Fostering peer-to-peer accountability is important

“The ability to learn is much more important, which again means, I think for me as a leader, how can I foster that peer-to-peer accountability where peers on the team could just have that feedback loop built in and say, ‘This is how we learn, this is how we do. We learn, and then we do, and then we learn, and then we do — and we just stay in that motion constantly, because that’s a resilient and robust system that doesn’t have a single point of failure, which is Adii being in the trenches and Adii being the bottleneck on all initiatives.”

The stair-step approach for entrepreneurs

“He describes it as a stair-step approach for entrepreneurs, and the idea there is that the easiest thing to start selling is perhaps an info product, some kind of part-time consulting, and then the next step up before building your SaaS business is a plugin or extension of some nature. And the reason for that is that you can build a smaller product; you don’t have to pull it all in compensating things.”


[00:00:00] Intro: This is Reverse Engineered. 

[00:00:04] Jon Penland: Hey everyone. My name is Jon Penland and Reverse Engineered is brought to you by Kinsta, a premium managed hosting provider. In today’s episode, I’m speaking with Adii Pienaar, founder of Cogsy. Adii, welcome to Reverse Engineered.

[00:00:16] Adii Pienaar: Yeah. Thanks for having me. 

[00:00:18] Jon Penland: Well, thank you for agreeing to hang out with us today and to get us started,

[00:00:22] can you introduce yourself to our listeners?

[00:00:25] Adii Pienaar: Yeah, given the space that Kinsta’s in, I think most people might know me as one of the original co-founders of WooThemes and WooCommerce back in the day. And then you kind of a post WooCommerce for me, at least, I found another company called Conversio, which was an email marketing automation tool, specifically for e-commerce brands and also kind of my first proper SaaS rodeo. Not only sold that too, but I would also say kind of my, you know, kind of early kind of other company sweethearts and Campaign Monitor. I remember back in the day when building WooCommerce or Woo in general, I’m always looking up at Campaign Monitor and what they were doing. So, sold that to Campaign Monitor and in 2019, I spent a bit of time with them and I now work on Cogsy, which is an image optimization platform, again, for e-commerce brands. 

[00:01:12] So, I’ve really, at least professionally, over the years, I’ve stuck to something that I think I know well, right? I’ve become a bit of a one-trick pony in terms of ultimately building software for e-commerce businesses. 

[00:01:26] Jon Penland: Yeah. And I do want to get back to WooCommerce and WooThemes just a little bit, I know that’s a few years in the rear view, but as you mentioned, we do host WordPress and so certainly a lot of our listeners are going to be most familiar with your work from that angle. So, we’ll come back to that, but I want to start by talking about what it is you’re doing today at Cogsy.

[00:01:44] So, what is Cogsy? What is the core problem Cogsy is trying to solve? 

[00:01:50] Adii Pienaar: Yeah. So, we’re ultimately addressing supply chain challenges that retail brands have. I look at the challenges I have in tech or a software company and I feel very fortunate, right? It’s like the many, many, many challenges that brands have around kind of the shipping of goods, of that just sticks around that operations about that. That’s pretty kind of broadly stated in terms of kind of what we ultimately do. If you go to our website today, we essentially built ourselves being your extra head of operations.

[00:02:22] And the idea there is just that there are some things that software is really good at and software is really good at complicated math, doing it on a kind of consistent basis and then ultimately finding those leading indicators to give you the opportunity to act proactively versus reactively.

[00:02:39] And that’s when you’re trying to build and I think as simple kind of outcome there for, you know, anyone listening that hasn’t been in that position is we ultimately kind of one of the core metrics that we report back to our, our customers is a reduction in kind of out of stock days, right? Out of stock days for in-retail brands, directly relates to lost revenue.

[00:03:00] And by using the various tools that Cogsy’s built and you’re putting them into that kind of your proactive, consistent kind of motion really, should ultimately kind of reduce those stockout days overtime.  

[00:03:13] Jon Penland: Yeah. When I was looking at Cogsy, looking at your website, I was struck by the fact that my impression of Cogsy is that it is a fairly specialized product.

[00:03:26] It’s not a mass-market product. You’re looking for retailers who retail online, who retail, physical goods and so it’s a fairly specific niche. And that’s interesting for me to think about because as we’ll get into you, you d, your background was with WooCommerce, which is in my mind much broader, I think, than that very specific niche.

[00:03:57] And so, I’m curious about the circumstances that led you to imagine this product, right? Because I don’t view you as somebody with a background in physical products in this very specific niche, how did you come across this specific problem and say this is something you want to try and solve.

[00:04:15] Adii Pienaar: Yeah. So, that’s a good question. So, all those years ago, I essentially kind of majored in accounting at the university and it was literally a university that I built the first part that became Woo, eventually kind of evolved to WooCommerce, but, I think that kind of that accounting hat or that accounting persona has always been a part of this.

[00:04:38] And then what happened on is in the last couple of years, my wife kind of built and then sold an ecommerce brand of her own. I was always her technical and kind of financial copilot in the business, I was never operational, but I could at least see how hard it was for her and her team to essentially kind of really wield ‌the powers of the tools that were available to them, right? 

[00:05:02] And I think the interesting thing there is that’s what most people don’t know about me is part of my, kind of part of my initial kind of motivation for kind of working on Woo and then ultimately working with WooCommerce has always been this notion of can I take something that’s truly sophisticated and powerful and democratize it to accents extent that it’s accessible for a broader audience. Which is kind of what I think we did four Themes back in the day, where the kind of granddaddy is custom development and we ultimately made themes more sophisticated at a price point that was more accessible. And we ultimately did it for WooCommerce. And then to come back to kind of Cogsy and those experiences that I had, you know, being that copilot to my wife’s business is there’s a very kind of big gap of tools available, right?

[00:05:56] Yes, there are many of these kinds of very sophisticated enterprise-able tools available for the biggest brands, the reality is that most of the brands are stuck in spreadsheets. And a spreadsheet is it’s a great tool for many, many, many different things and there is no way for us to complete the, get people out of spreadsheets, but that’s what Cogsy is trying to do, right? 

[00:06:10] Adii Pienaar: It’s trying to build an alternative to the spreadsheets and essentially kind of you’re focusing on the things that makes software really good. So, one of the examples being in a spreadsheet, regardless whether you’re doing it for inventory data or something else, if your data gets outdate constantly or so, whereas if you had a specialized tool with connect data sources that keeps data kind of in sync, right? So, yeah without rambling there, but those were the kind of the common threads and at least how I got to the point where I was like this, this is a problem that’s big enough for me to, to tackle.

[00:06:51] And I have enough historic, just experience, whether from the WooCommerce or my accounting experience or my experience kind of being the copilot to my wife’s business, to ‌tackle this, even though I’ve never been an operator at a retail brand. 

[00:07:07] Jon Penland: Yeah, Andii, the onion I’m going to keep peeling out here for just one more question is did you encounter a retailer selling physical products who was running into this problem? Because there’s sort of this truism of building SaaS, which is don’t build a product and then go look for a solution, right? Or go look for a problem that it solves. 

[00:07:33] You start with a problem and then you solve it. And, what’s a mystery to me is how, someone with a background that, from my perspective, it seems to be very software-focused, how did somebody with that background and even, it sounds like your wife had a software business that she sold. 

[00:07:52] How did you be, just have the visibility to see this problem? Where did it actually sort of come into your life so you said, “Oh, there’s a problem here that can be solved with software.”

[00:08:00] Adii Pienaar: Yeah. So, one question that in my wife’s business was a physical retail business. So, that’s where I got some of that. I actually think that the more interesting thing you’re doing is that I, at least for Cogsy and maybe to some extent Conversio, that was the predecessor here, for me at least, I did things that I would not recommend first-time founders do, right?

[00:08:19] First-time founders, I always recommend, do the customer development beforehand. Don’t believe that you can build it and they will come, right? We’ve all heard that cliche thrown out. With Cogsy, it was more a sense of understanding that there is a problem there and then being able to say, “You know what? I’ve been successful enough to have diversified, at least my financial interests, that I can be slightly riskier.” 

[00:08:50] And I think how that plays out is I’m very clear about the what game I’m playing, right?

[00:08:59] When I pitch my investors, I tell them I want to build the NetSuite killer. The NetSuite is a multibillion-dollar kind of business, right? So, for me, it is a moonshot thing. I don’t just want to build, and when I say this, I don’t mean that in a disparaging way to other bootstrapped or lifestyle founders, whatever kind of labels were, I’m fully on board with any of those.

[00:09:28] Adii Pienaar:  I’m just very clear about the game that I want to play, or I want to build a category of finding tools. So, I think there’s that risk, but coming back to how that plays out in the short term it essentially means I can build the first version of products and that becomes the line in the sand from which I kind of work and have those initial customer conversations. 

[00:09:49] So, I’m already being opinionated and I’m trying to push a kind of this project into a specific direction versus just being completely curious and saying, “Hey Jon, you are the ‌ideal customer that I would love to build for. Can you tell me about your problems?” And I keep my opinions out of that. That’s definitely a safer way to do it. It’s a more posh or conservative manner to do it, but I said, I’m really clear about that game, which is why I skipped that first part of doing extensive customer development.

[00:10:20] Typically lean startup methodology stuff. I skipped all of that, built the first version, and just kind of iterated from there. 

[00:10:27] Jon Penland: Yeah. And I do think your background there in entrepreneurship and your, as you mentioned, sort of financial stability outside of Cogsy, personal financial stability outside of Cogsy, are important sort of footnotes, you know, for listeners to be aware of, right?

[00:10:42] This is a moonshot approach, and that’s awesome. Adii’s at a specific circumstance that allows him to do that, allows him to take that sort of risky bet, so that’s awesome. I am curious because as you’ve described, you’ve been very intentional about what it is that you’re shooting for at Cogsy.

[00:11:02] And that leads me to ask what it is you actually do at Cogsy? Because I have to think you’ve been similarly selective in what you choose to actually spend your time on.

[00:11:13] Adii Pienaar: Yeah. So, I think that the biggest change, and I should know this because I drafted a tweet about this in the past week, I’ve not published yet, but in reflecting almost those step changes that I’ve made in terms of the kind of leader I am from Woo to Conversio to where I’m at today with Cogsy and my team. 

[00:11:33] So, with Woo, the way I see it is it was very much about – learning has been going and learning for the first time. I think I needed to learn lessons, that was the first rodeo. With Conversio, it really was about how can I take those learnings, and improve upon them, right?

[00:11:48] How can I stress this down? To what extent can I replicate them? Which things are universal and work and which were just very specific to Woo, for example? And with Cogsy, it almost comes full circle in the sense that I now want to use those lessons and I want to empower those individuals around me in terms, you should not use those lessons.

[00:12:09] I should not be the only one learning or applying those lessons anymore. So, I’m much more of a coach and a mentor today than I was previously. I think that’s been a big change for me and to your point, yes, that was very intentional. Conversio was a life-changing exit for me.

[00:12:28] It could have been, this is all I’m obviously speculating, right? It could have been bigger. How do I figure it out? How to get myself out of the trenches and hire really great people that could push me forward on certain things? So, concrete example there is, as a founder, I’m a generalist.

[00:12:49]  I can wear all the kind of different hats within, except for actually coding or writing code myself. But I’m also technical enough, for example to, I can scope out a project and I can understand, API kind of limitations, et cetera, right? So, I can wear most hats to some degree, but some things I’m better at.

[00:13:09] And with Conversio, marketing was a thing that I held on for too long and I couldn’t find that person that could come in and tell me to a point where I could trust and be confident that, “Hey, Adii, this is how we’re going to do marketing. This is how we’re gonna grow the business.” So, and how that then kind of plays out to where we’re at today is hence why we’ve raised the money we’ve raised.

[00:13:30] I’d like that it allows me to go hire those kind of more senior, more experienced individuals that I can surround myself with and they tell me what to do. I thought all I’m really doing is I’m always just kind of contextualizing that in terms of the bigger picture, right? I’m doing that and I’m being a coach and a mentor to them on a one-on-one basis.

[00:13:50] So,  that’s been a very intentional change and a progression from both from Woo to Conversio where that changed again to where I’m at today and how I can see my role, especially in that function of being a business and a team leader. 

[00:14:05] Jon Penland: Yeah. So, one of the things that I think whether someone is a founder or just a relatively high-level leader in a growing company, is that they have to master the VR of getting themselves out of the day to day, as you said, or I think “Out of the trenches” was the phrase you used.

[00:14:26] I’m just curious to ask, in general terms, what has been your approach to getting yourselves, so to speak, out of the trenches? I know at Cogsy I think you may have designed it from the beginning, so perhaps looking back a little bit further to some of those lessons learned at Woo or at Conversio, right?

[00:14:45] What are some of the things that somebody who’s listening to us today, or, you know, myself as a leader at a growing company, what are some of the strategies or approaches I can use to identify ways to get myself more out of the trenches?

[00:15:00] Adii Pienaar: Yeah. I think, actually, the only one that really comes to mind as a prominent thing, Jon, and it’s the example I use here as the universal kind of recommendation, to really find those truly talented individuals on your team that are aligned with your culture, values, mission, right?

[00:15:19] So, high alignment there and they have really shown anything in the realm of their ability to take initiative or responsibility, the thirst for learning some kind of aspirational, ambitious quality, and then really backing them. And saying, “Hey, what happens if I just step away from this a bit and see how they write?” Right?

[00:15:42] And I think how this kind of played out the more recent example is, so my now co-founder in Cogsy, he was my first engineering hire with Conversio. You can see when other individuals in the team start listening to people, right? That’s normally a good sign, “Hey, here’s a potential leader.” He was affectionately known as Papa Bear on our team. There was something that kind of the team, it happened organically. It wasn’t, it wasn’t the Adii thing that designated him, you know, with those kinds of role and we didn’t have a kind of very strict hierarchy within Conversio titles and whatnot, within Conversio and with Titles either. 

[00:16:26] But it was a case over time of saying, “Here’s an individual, can I give them some room to grow into and see whether they take up the responsibility?” And that was the case.

[00:16:35] He ultimately became that, on the technical side, became the trusted confidant for me, where I could go away, be offline for a whole week, and know that there might be other times of the pop-up that no one in the team handles, you know, would be able to handle. But if the servers went down or someone got stuck on kind of a pushing a new feature to production, Stefano would be that person that could solve that, right?

[00:17:00] But at some stage I said, beyond identifying who those individuals are, you have to give them the space to essentially create a feedback loop where you’re able to trust them. Because I think that’s the thing, founders are so, I know this is true for me. I backed myself, so I trust myself, that’s the mindset you’re in. 

[00:17:25] So, you have to find a way of how do I trust someone else and I don’t have to second guess them and think, “Ooh, I can do this better.” Right? To do that, it’s a bit counter-intuitive, yes, you have to give them the opportunity to show you, “Hey, this is what I can do, hence you can trust me and step away.” 

[00:17:41] Jon Penland: Yeah. And one of the things that I feel like I am learning right now is when you do step away that you need to go ahead and anticipate that they’re going to do things differently and, and not judge the merits of their work based on the fact that it’s different, but to give it time to actually produce some outcomes.

[00:18:05] Because I think, for me, when I hand off a task or back away and let someone take something on, if they don’t do it exactly the way that I was doing it or would do it, I can have this internal reaction of, “Oh, this isn’t working.” Right? I can have this immediate sort of gut reaction of, “I don’t know if this was a good idea. Maybe they’re not going to be able to handle this.”

[00:18:31] And then, and then they’ll do it differently. And it’s essential, I think this is what you were speaking to when you said you have to give it time to develop that feedback loop, where you have to, you have to let go long enough to see the results of their work.

[00:18:49] You have to let it go, while you can immediately pull it back if it doesn’t go exactly the way you were expecting. 

[00:18:54] Adii Pienaar: Exactly. Right? Because if you take being a farmer in a business. You’re ultimately giving yourself, an indefinite timeline to make mistakes and figure things out. So, why should that not be true for someone else on your team, that’s stepping into a similar emotion of being the leader for a project or an initiative or an objective and outcome that you’re trying to reach. 

[00:19:18] So, I think that it doesn’t help if it gives someone space and if after a week they make a “mistake”. Air quotes for those listening, make a mistake and you immediately pull it back, right?

[00:19:29] I think, that’s a sure way of never being able to step out of, kind of the trenches. I think that the motion that I got, I think I only understood this much later in my junior conversion as well, but you have to flip it from almost being directive. And giving someone, “Here’s exactly what I need to do,” to emotion where you’re keeping you, we’re holding them accountable, right?

[00:19:56] So, we often speak about the way we think about accountability within, within Cogsy today is very much like, I don’t mind someone making a mistake, that’s not a problem. What is a problem is if you don’t put up your hand afterwards a, and say, “Hey, I screwed up here. This was a mistake or this was subpar” and b, “What did we learn from this,” right? 

[00:20:16] Because there’s either, and sometimes the learning is just like, “Hey, we experimented with this marketing campaign and it doesn’t work,” right? And that’s a kind of almost the end of the line learning and that’s fine, but then you retrace your steps from there and say, “Okay, based on that, this is what we’re going to kind of try next,” right? 

[00:20:32] And then, then the motion is creative. Other times it’s like, “Ooh, this didn’t work out, but here’s a kind of almost a slight pivot or a slight tweak that we can make to rectify this,” right? But those kind of the ability to learn, I think is much, much, much more important, which, then again, means I think for, for me as a leader, how do I foster that peer-to-peer accountability?

[00:20:57] Where peers can just, on the team, could just kind of have that feedback loop built in and say, “This is how we, this is how we learn,” right? “This is how we do it. We learn and then we do and then we learn and when we do,” and we just stay in that promotion constantly because that’s a resilient, robust system that doesn’t have a single point of failure, which is Adii being in the trenches and Adii being a bottleneck on all initiatives.

[00:21:21] Jon Penland: Yeah. I love that idea of accountability as opposed to necessarily being singularly focused on results. It’s, “Hey, if something goes wrong, do you take responsibility for the fact that something went wrong, and do you learn from it?” And then that being a better measure than pure measure of, “Was it successful?”

[00:21:39] Right? I love that. That’s a great idea. 

[00:21:41] Adii Pienaar: And, I mean I’ll add a little more color there, Jon, because I, okay, this is the things that I’m very passionate about, that’s why, so I think at least for the Cogsy, on most of the things that we work on, we don’t direct anyone in terms of what needs to happen. I think we speak in terms of, this is the outcome that we’re trying to get to, right? 

[00:22:00] And the only non-negotiables there are our values. We got a document, it’s called the Vivid Vision. There’s a book by a gentleman named Cameron Herold, by the same name and idea basically is that it’s a three-year plan with loads of color and context as to kind of how you imagine your business, team, product, et cetera, to look like in three years’ time. 

[00:22:24] And part of that is around kind of the values, the way you think that the state of truth for you as a, you know, company and a team. And ultimately those are, that’s the guard rails. That’s if everyone on the team operates within those guard rails, then I don’t really care whether they zigged and zagged or walked in a straight line towards that outcome, right? 

[00:22:42] I don’t care whether they wore shoes or walked barefoot. That doesn’t matter. Those were not important ‌points. And I think the reason why I’m so passionate about that is I understand that there are many, many, many people in this world that kind of don’t want to be an entrepreneur and don’t necessarily want to have that the fulfillment of the reward from, it comes with complete autonomy.

[00:23:13] But I bet that most people have some inkling of that. And they want for some parts of their kind of work, they want input, they want influence, right? They want to matter. They want to be heard. And I think, hence why I think the broader, you can kind of draw those guardrails and still have them kind of clear these are the clear boundaries.

[00:23:33] That gives someone a lot of space to be creative and do their best work be their best selves at work and do their best work. 

[00:23:42] Jon Penland: Yeah. The way we try to express that idea is we talk about treating our team members like adults. We talk about not micromanaging and allowing our team members to tell us how would they, how they should be doing their work.

[00:23:57] That’s how we sort of express a similar value. I don’t think we fleshed it out quite as robustly as you did in your answer, I feel like I’m might make this might be good to be highly recommended listening for a bunch of our team members, we follow the same sort of idea, which is that we want our team members to have as much autonomy and flexibility as we can give them, because we think that we think that actually produces better results in the long run. 

[00:24:15] Yes. Produces happier team members who bring, who produce better results because they bring their best ideas forward. They’re not just ticking the boxes that we’ve lined out in front of them.

[00:24:32] Adii Pienaar: Exactly. Because otherwise it’s like, if you do that, then I think you create an echo chamber of very homogenous ideas where if it’s only the top leadership setting direction constantly and how things are done, it’s not a very diverse kind of conversation that’s happening, right? 

[00:24:48] You can definitely build a great business that way. I just think they can build a better business by involving more smart people, bringing their unique ideas and perspectives to the conversations. 

[00:25:04] Jon Penland: Yeah. One of the things that I find happening quite a bit and I hope this comes across right, but one of the things I find happening quite a bit in my own teams is, is somebody will come to me and I manage just for example, I manage legal IT and HR primarily, those are primarily the areas I’m involved in and they might say, “Hey, there’s this new app that I want to start using. What do I need to do?” And, “I don’t know.” Right? You need to go “Oh, we have an IT manager, Eric, and he knows how to do this for sure. 

[00:25:37] You need to go talk to Eric ’cause I don’t, I don’t even know.” I know that there is a process and that’s what I care about. I care that there is a process and that Eric has defined a process and written it down.

[00:25:46] But I don’t actually know what that process is. Whenever I need to use a new app, I’m going to go find that process and follow it. Yeah. 

[00:25:55] Adii Pienaar: Yeah. I think, and then we can step off this because otherwise I’d think about this for hours, but I think that the reason why that works is that empowers an individual, right?

[00:26:06] If you illuminate, “Here’s the resources. Here’s the kind of, here’s the things you can do,” they’re empowered. Which is a very solid foundation for anyone to then go out and do their kind of best work.(Empowerment is a very solid foundation)

[00:26:20] Jon Penland: Yeah, absolutely. Yeah. So, we do need to move on to other topics and I do want to, I do want to talk about your background at WooThemes because, like I said, you know, as a company that does a lot of business and the WordPress space, our listeners are definitely going to be most familiar with you from that background.

[00:26:38] So, uh, just in brief, can you tell us about WooThemes and the process? I think most people are going to best know you for your involvement with WooCommerce. So, the founding of WooThemes and then the eventual launch of WooCommerce, can you give us the cliff notes version of that process? 

[00:26:53] Adii Pienaar: Yeah. So, all the way back in 2006, 2007 is when I think that the concept of premium themes kind of popped up. And premium on that stage was really just our way of saying because there was, the free themes already existed and premium was our we could have just said Paid Themes, but no marketer would ever like that. 

[00:27:19] But I think there were, there were a couple of us and one of the gentleman’s names is completely blanking on me now, but it was myself and Brian Gardner who’s now with WP Engine after working on StudioPress and a couple of other things over the years.

[00:27:27] And we started off with about the same time, just as freelancers, right? And I had a popular blog at the time. I had a bunch of free themes and I just built this first product and I started selling it, it to school, the Original Premium News Theme. That was the name. And it was just this premise of your work percent I think had shown an early kind of inkling that it wasn’t just a blogging platform, it could be a CMS, a complete CMS and it was very magazine-like websites, content and websites size became very, very popular at the time and that’s what it was.

[00:28:00] And through that, I connected with Magnus and Mark that eventually became co-founders within Woo, and we officially kind of shifted things off my personal website and decided on kind of Woo as a brand and this is where I think mid-2008. 

[00:28:20] And then the three of us really just had a lot of fun learning. I think it was a fascinating journey, this is not a humble brag, but the business grew so well that we skipped over so many of the ‌learnings that one should probably have within a business, right? 

[00:28:31]Then we ultimately had to be much later on have to kind of try and fix them, much harder if you think through something like team culture, it’s much, much harder to do this later on than being intentional about it and just kind of doing it at the beginning because old habits die hard.

[00:28:51] But then through that, we eventually kind of really stumbled into this and again, just falling our customers. I think for anyone that thinks back to Woo, but kind of back in the day, I think the thing that we were most part about was I think the brand was perky. I think we were really good at building product, but our customer support was, was absolutely excellent.

[00:29:11] And it was really kind of our ability to live very, very close to our customers that taught us or showed us that what customers started wanting was they want, they were bought buying these, at that stage, the top-selling category for themes was what we called business websites, which is just a simple kind of, you know, kind of brochure-like website.

[00:29:30] And they kept telling us, “Hey guys, we would love to add a shopping cart to this. Can you help with this?” And we looked around and we couldn’t see something in the, in the ecosystem that we’d liked, meaning, um, and our criteria wasn’t functionally could this allow someone to sell? I think WPE commerce at the time and whether it still exists was the predominant payer and there was a plugin called Shopp, with two Ps, but neither of them would have allowed us to build really great looking themes, which was what we had built our reputation on.

[00:29:50] And we ultimately embarked on this kind of process of, uh, trying to build it ourselves and got close to getting a core contributor from WordPress, working with us, that didn’t work out, try to build it internally, we weren’t technically strong enough. 

[00:30:18] And then we really stumbled onto Mike Jolly and Jay Koster, who, you know, we’re working on Jigger Shop, which was a competitor at the time and ultimately came the fork for WooCommerce. So, and there’s so many stories that I think that kind of the last thought that I’ll share there is along the way, we made so many assumptions, Jon, about how we would build WooCommerce and the model, right?

[00:30:38] The initial model for us was we would monetize it by selling themes, ecommerce themes. And Jay and Mike came in and we adopted this kind of extension-led model and app-store like model from them, which completely changed the business, right? And then within a year after launching WooCommerce, WooCommerce-related revenue became 90% of our business.

[00:30:57] So, a lot of that was not planned, but it was really just us staying in that discovery phase and seeing where it took us. It was a rabbit hole and, you know, today, today WooCommerce is what it is, why it’s, but I think we would definitely be overplaying our hands if we said, we were these strategic masterminds and we have absolutely everything figured out.

[00:31:20] Jon Penland: Yeah. So, so, if I could, if I could paraphrase a little bit, it sounds like themes where your primary business and you had clients who were going, “We want to add a shopping cart to these themes that you’re making for us” and there was nothing on the market and you were like, “All right, well, let’s, let’s build a plugin so that we can keep selling themes that have a shopping cart” and within a year, it was like, “All right, the themes don’t matter so much anymore.” 

[00:31:45] “The shopping cart is the business here,” right? How quickly did you, and, and for, you know, perspective or background your, I didn’t really come into the WordPress space until 2014, 2015 and so by the time I showed up WooCommerce was, everybody knew WooCommerce in the WordPress space.

[00:32:01] It was the standard if you wanted to set up an ecommerce site. So, what was that process of deciding, “Hey, we’re going to, we’re going to shut down the theme side of the business and focus on, um, ecommerce focus on BlueCommerce?” 

[00:32:15] Adii Pienaar: It was a very natural process, right? But I think at that stage, you see a very far source, horse in your business and you’re like, “Well, we should totally place more bets around that horse fights.”

[00:32:25] And we actually tried, we didn’t actually shut down the themes either, Jon, we just siphoned off some resources from themes and we actually, we thought about, we tried our hand at building other plugins, actually. And the way we scaled WooCommerce was by using third-party developers, right? That’s, could build very specific add-ons or extensions to the platform.

[00:32:45] So, it was very kind of distributed, I’m going to say workforce, but distributed for us to help us solve for all of those kinds of edge cases and the needs that merchants around the world and different industries, you know, kind of needed from us. And it wasn’t until, I think, I would say two, two and a half years into the business where we actually looked at that and like, “Well, we should have just focused on that.”

[00:33:08] We should have probably shut down themes and we should not have built these other kind of plugins. If WooCommerce wasn’t as big, like, they would have been material businesses in their own, right? But there were so tiny relative to what WooCommerce was doing, that we should’ve just focused on that.

[00:33:26] But then you get into that challenge, which essentially is, I think we had on themes where which is, once you build something and especially within the WordPress community, people expect support, right? You’ve got them stuck on the product and it’s very hard to take that away and deprecate things.

[00:33:41] Jon Penland: Yeah. And, and there are security considerations as well. Something comes up and all of a sudden, you know, there’s a security issue that wasn’t, you weren’t aware of in the past, and that has to be addressed and you can’t leave those users who are using that theme you developed six years ago.

[00:33:55] You can’t leave ’cause you still got a thousand sites out there using it, right? 

[00:33:59] Adii Pienaar: Exactly, right. Then there was also before we eventually changed, I think just before I stepped down as CEO towards the end there, we changed our licensing. I think we started limiting it to a year, right? But before that was the exact challenge that we had, is if someone paid these pages 70 bucks for a theme and seven years later, they still want to bombard you with support questions and they expect a kind of an hour, no more than an hour as good turnaround time on response.

[00:34:28] Jon Penland: Yeah. That’s absolutely tricky to manage. I am struck, I’ve never really thought about the extensions element or the ad-ons element in the WooCommerce space and about, you know, where the ecommerce plugin market was at that time, but I’m struck that you probably actually froze some potential competitors out of the space by making WooCommerce something they could build on instead of them having to build something from scratch, right? And I’m curious if you’ve ever thought about that. I mean, was this a happy accident or was this a strategic choice, right? That you froze out some competition in that way?

[00:35:05] Adii Pienaar: It’s totally happy accident because, I agree with you, I think that that’s probably true, right?

[00:35:12] I was chatting to someone yesterday that’s now on a summer’s base to Cogsy, but the individuals who had, his first start building an extension business for WooCommerce, and I used the example of the SkyVerge team. This SkyVerge team had a really great exit and they did so exclusively based off, no, not exclusively, but on the back of kind of building new commerce exchanges, and I, I have no doubts that they probably had at least a similar kind of, know the technical ability that we had with WooCommerce and they could have built WooCommerce alternative fights, but it was compelling enough for them to rather bold with us than against us, right? Which is always a fascinating kind of phenomenon in the open-source ecosystem.

[00:36:00] So, that makes sense. In hindsight, I cannot claim being the strategic mastermind and having the foresight to plan things out like that all those years ago. 

[00:36:11] Jon Penland: Right. Well, and as a developer, who is an entrepreneur, if you are sitting there looking at the space and you go, “I have a path to potentially having access to millions of WooCommerce users that I can sell this $4-a-month extension to,” that’s a much faster path to revenue than building a new product.

[00:36:30] And so, it becomes compelling, very compelling for other entrepreneurs in the space to build on top of what you build, as opposed to building a competitor. Definitely a much more viable path for them because they have sort of this, this predefined customer base that they can, that they can try and tap into. 

[00:36:47] Adii Pienaar: Totally, a content creator for, for this approach, a buddy of mine, Rob Walling, who is now a founder of TinySeed, also a founder of couple of other companies, but he describes it as a stair-step approach for kind of entrepreneurs. And the idea there is that the easiest thing to start selling is perhaps an info product, some kind of your prioritize consulting.

[00:37:08] And then the next step up before building your own kind of your SaaS business is a plugin or extension of some nature. And the reason for that is like,”Hey, you can build a smaller product. You don’t have to build all-in compensating thing,” you can in the case of WooCommerce, you could build geography support for kind of German stores. And so, a very small niche, so you can build a smaller project, but the marketing and distribution, the go-to-market strategy, is also much easier. You’re not building a thing and you have to figure out your own customer acquisition channels.

[00:37:41] You can piggyback off of the captive audience that the underlying platform already has. So, it’s just easier as you cut your teeth as an, as an entrepreneur, it’s just easier building in an existing ecosystem on an existing platform versus something completely from scratch. 

[00:38:00] Jon Penland: So, we’ve talked about kind of two big areas in your journey as an entrepreneur. We talked about Cogsy and we’ve talked about WooThemes and WooCommerce. The third and sort of final stone that I want to touch on in this conversation is a book that you published last year. So, last year, 2021, you published a book called “Life Profitability” and I wanted to give you the opportunity to kind of explain what that is to our listeners.

[00:38:24] So, what’s the central premise of that book? 

[00:38:27] Adii Pienaar: Yeah, I think that there’s really one idea that I want any reader to take out of it is that our work or our businesses, right? If you’re, if you’re entrepreneur should be there to serve our lives and not the other way around. And I think just breaking that down,

[00:38:45] I, I don’t like the idea of – we work to live or live to work. I think both of those feel very binary, firstly. Secondly, I also don’t like this idea of work-life balance. I think the idea of work-life balance proposes that you either work or you live and I think work and our professional kind of endeavors is just a single part of life.

[00:39:08] So, what I try to do within the book was propose a different approach where you can do these things in life, whether it’s work, whether it’s some kind of professional endeavor, or just other things in a way that is profitable in the context of your whole life. And for me, it’s regional – it’s been a case of being really aware of what those important things are in my life, right? 

[00:39:31] I think in the same way that you would construct a financial investment portfolio, I have a concept of a life portfolio and I know that, for me, at least, there are concrete things. My family needs to be in there and my health needs to be in there, my business needs to be in there, ambition wise.

[00:39:47] But I also need kind of the space and the time to learn that needs to be in there. It’s a softer or more qualitative kind of thing, but I need, I know that if I’m going to stagnate in terms of my personal development for too long, I am probably not a happy Adii, right? I’m not being the best version of myself.

[00:40:07] So, it really just there’s around firstly building a clarity around what that looks like and then trying to set up, create some space in your life and then set up your life in such a way that you can nourish every single aspect of those things you identified in that life portfolio of yours. 

[00:40:25] Jon Penland: Yeah.

[00:40:26] So, is this idea of a life portfolio, the idea that the things that are in your life need to contribute to sort of a healthy and a whole life, where did that, where did you learn that idea? Where did you develop that concept? Is that something you’ve always, you know, since you were 17 years old, you were just this, you know, sage 17-year-old, or is this something that you developed at a later stage in your life, this idea? 

[00:40:51] Adii Pienaar: Yeah. So, definitely later stage, I think they’re going to be the, almost the kind of precursors to this, it’s definitely kind of having failed miserably at some of those things in my personal life, right? Whether it’s being a good partner to my wife or, you know, being a good dad to our kids, or just being a crappy leader within the teams that I’ve built.

[00:41:12] So, all of those things are probably the precursor. So, I felt the pain. But then very organically, Jon, what happened was within my team a conversion, we’re probably about halfway through the journey, we stumbled onto this language, which was, we are a life-and-family-first team and the idea was just rooted in, how can we just structure work to at least honor that beyond work there is more meaning? 

[00:41:38] And I think what we said is we want to do challenging, stimulating fun work, but we have to acknowledge the most meaningful experiences that we can have as individuals outside of work. So, I eat with our families or go on vacation or whatever it was. I mean, it probably is a very unique perspective.

[00:41:57] So, and we’d start doing small things within our team, which is, if someone is on holiday, we will not ping them. We will not even tempt them to kind of come back to work unless they are the only person that can put out this fire, right? So, it became those small little disciplines, but the philosophy around this was what can we do as a team, a collective, as a company, that will honor that unique individual to have that kind of your life-and-family-first experience whilst working our team.

[00:42:27] Jon Penland: Yeah. What prompted you to write the book? Because I imagine you could have developed these ideas. You could have applied them to your own life. You could have applied them to the businesses that you’re building, but you then opted to, you know, as a software entrepreneur, somebody who’s been focused in that space to go in a different direction and, uh, write a book.

[00:42:45] I mean, I can go on Amazon and buy the paperback, right? To write a physical product, what prompted you to take that extra step and try and put this idea out into the world, in the form of a book. 

[00:42:56] Adii Pienaar: Yeah, mostly legacy. I think that’s the most predominant part or primary motivation for me was, was legacy and specifically not less so about the public and more so about how at that stage, I only had the two boys and we were fortunate to add a little girl to the mix very recently, but at that stage, you were really like, “What breadcrumbs can I leave behind for my boys that if something were to happen to me today and they were still young and they didn’t fully grasp who their dad was that they could actually pick up an actual artifact and maybe learn a little bit about the more kind of nuanced parts of it if they wanted to?”

[00:43:33] So, it is very, I think it’s very self-indulgent, right? I would never position that I’m doing them a favor and it was all around me why they get there. There’s a kind of that, you know, somewhere on Maslow’s hierarchy, the need to be relevant. 

[00:43:57] And I think, I would hope that if something happened to me today, that’s kind of years down the line, my boys would want to, my kids would want to learn more about their dad, right? That’s the kind of, that’s the very personal hope. So, and I think a book to that extent, is a great way of trying to accomplish that.

[00:44:15] So, that pretty much is, I would say, you know, 67% of the concentration was that and then there are other things, but that was definitely kind of the most personal, most prominent motivation. 

[00:44:27] Jon Penland: Yeah. Yeah. Well, Adii, as we sort of wrap our conversation towards a conclusion here, I do have a couple of wrap-up questions that I like to ask all of our guests.

[00:44:37] So, the first is, is there a resource that you think our listeners would find a lot of value? And it could be a book, could be a, you know, a blog, really anything. Is there something that you consume that you would like to recommend? “Hey, go check this out.”

[00:44:50] Adii Pienaar: Yeah. So, I recommended book and the book’s name is Siddhartha by an author called Hermann Hesse. And it’s just a book about a journey and I think that there is, yes, it’s been an inspirational book for me and I, I think that the key is the the takeaways are not what is promised on the cover and this is a fascinating read for anyone that’s on the journey.  

[00:45:14] Jon Penland: Okay. Awesome. Well, we’ll make sure and get a link to that in the show notes or listeners can check that out.

[00:45:19] And then last question for you today is where can our listeners go to find out more about Cogsy or to connect with you?

[00:45:25] Adii Pienaar: Yeah. So, the best place to connect with me is probably on Twitter, where I’m @Adii. So, Adii double i, everything is linked up there. You can also find Cogsy from there, otherwise, Cogsy is just a, C O G S

[00:45:42] Jon Penland: Well, Adii, thank you so much for taking an hour out of your day to hang out with us here at Reverse Engineered today. We’ve really appreciated having you on the show today. 

[00:45:49] Adii Pienaar: No, thanks for having me, Jon. 

[00:45:52] Jon Penland: And thank you to our listeners. That’s all for today’s podcast. You can access the episode show notes at 

[00:45:59] That’s K I N S T If you enjoyed this episode, don’t forget to subscribe to Reverse Engineered and leave us a review on Apple Podcasts or the platform you’re listening on right now. See you next time. 

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