🎙️ Episode #3

How Technical Founders Can Build Thriving and Fruitful Company Cultures in Remote Organizations

James Laws - Co-founder of Ninja Forms

Show Notes

James Laws is a non-technical co-founder of Ninja Forms, which has proven itself as one of the most successful WordPress form plugins on the market. In addition to this, he founded his company Saturday Drive as a single office business in 2014, and — in less than a decade — grew it into a multi-million dollar operation with 20+ team members distributed across the globe.

But James’s expertise stretches well beyond being a successful entrepreneur in the WordPress ecosystem. Over the past several years, his passion for teaching, public speaking, and workplace dynamics led him to create a weekly podcast, blog, and newsletter where he provides leadership advice to promote culture-building.

In this episode, we’ll dive into the practices James has used to create dynamic environments for businesses and their employees. But more specifically, we’re going to look at how technical founders and entrepreneurs with remote companies can create company culture that ensures their employees are empowered to perform at the very best of their abilities. 


Thanks to James for joining us and providing such valuable insights into remote culture building. Join us next week with Matt Medeiros to learn how entrepreneurs and SMBs can leverage podcasting for brand building and business growth.

plugin.fm is brought to you by Freemius, your all-in-one eCommerce partner for selling software, plugins, themes, and SaaS. If you enjoyed this episode, head over to plugin.fm to check out previous episodes.


Episode Contributors:

James Law — Guest

Patrick Rauland — Host

Vova Feldman — Content quality control

Scott Murcott — Content research and preparation

Zee Hazan — Audio and video quality control

Emiliano Pioli — Audio and video editing

Chapters and Episode Notes

00:00 – Intro

02:30 – Building Culture and Leadership: The Origin Story of Saturday Drive in the WordPress World

06:45 – Fostering a Positive Company Culture: Hiring, Leadership, and Business Growth

09:04 – The Impact of Your First Hire: Shaping Company Culture and Success

11:05 – When Should You Start Doing Internal Work to Define Your Company Culture and Values for Hiring?

13:33 – Empowering Your Team: Trusting Expertise and Building Safety Nets

21:12 – Nurturing a Strong Culture in a Distributed Company: Insights and Strategies

29:45 – Is Introversion a Challenge or Superpower for Founders in Building Culture?

33:24 – Identifying and Addressing Culture Misalignment in a Remote Environment

41:19 – Indicators of a Healthy Company Culture: Selflessness and Autopilot Ethos

44:01 – What Fosters Accountability and Psychological Safety in a Strong Culture?

49:30 – Managing Global Diversity in Distributed Companies: Conflict and Communication Strategies

55:30 – Discovering the True Essence of Business: The Power of People and Purpose

57:46 – Outro


James: I always look at culture as two things: it’s who we are, and it’s who we want to be. So when I hire, I’m looking for that somebody who will enhance who we are or will add to us something that we are not, but we strive to be.

Patrick: Hello everyone and welcome to the plugin.fm podcast, brought to you by Freemius. Every week, we sit down with innovative figures to discuss their contributions to WordPress and get a unique take on entrepreneurship, life, and everything in between. And while we’re at it, we uncover actionable practices and strategies that you can use to succeed in your own business journey.

My name is Patrick Rauland, and today I’m joined by entrepreneur and leadership and culture-building coach, podcaster, and blogger James Laws. James is a non-technical co-founder of Ninja Forms, one of the most popular WordPress form plugins out there. His company, Saturday Drive, started out as a single-office business in 2014 and is now a multi-million dollar globally distributed operation with more than 20 team members.

But James is more than a savvy business person. Over the past several years, he followed his passion for teaching, public speaking, and workplace dynamics, and created a weekly podcast, blog, and newsletter about transforming company cultures through effective leadership. He understands how founders can navigate the unique challenges faced by WordPress makers, and we’ll dive into those practices he’s used to create thriving and fruitful environments for their employees.

James, welcome to plugin.fm, and thanks for joining us.

James: Well, thank you, Patrick. I’m excited to be here, and I especially like the qualifier, the non-technical founder bit. That’s always a nice little touch. 

Patrick: You add so much more than the code, James. You are so much more than just a coder.

James: Well, in the early days, I wrote a little bit of code, and they’re still paying that technical debt off, you know, years later, decade later. 

Patrick: But it’s good to know a little bit about coding, right? So, good to know a little bit as to how hard it is and what things are easy and hard. But then, you definitely focus on other areas, 

James:  Absolutely.

Patrick: cool. So yeah, go ahead.

James: I was just gonna say, no, I think when, as a non-technical founder, having at least a foundational understanding of what is possible and the complexity that it takes to do certain things is super helpful when having conversations and trying to lead engineers. To say, “This is the vision, that’s what we want to build.” And so yeah, I’m not technical, but I’m dangerous enough to make all the engineers fear when I walk into a room.

Patrick: I love that. I love that, so I want to get started with it because we’ve talked to a lot of technical people who have built up their own businesses. They’re the lead programmers, they’re the people driving the project. But I want to talk about culture building and leadership with you. But before we get into that, how did Saturday Drive start out? How did you find a need, and what was your role in the initial company?

James: Sure. So, you know, I’ve told this story over the years. I’ve told this story so many times, I wonder how consistently I stick with it. Because, you know, after a decade or so, you start to, the details start to get a little fuzzy. But basically, my business partner and I, Kevin, were trying a lot of different things in business. We were experimenting. We did freelance web design, we did some print design stuff, mostly leaning on my design background. That’s where I kind of started in the space.

I was working for a regional credit union, and the CEO was on the board of Junior Achievement in our area, Chattanooga Junior Achievement. So if you’re not familiar with Junior Achievement, they offer, they go into schools, and they provide financial education for students, to think more responsibly about finance, about taking care of your bank, entrepreneurship, things like that.

So, they were being kind of ripped off by this local web agency, and the CEO asked me to kind of step in and evaluate whether that was true. They had the feeling they were being ripped off, but they weren’t completely certain. So, they asked me to step in, and I sat in a meeting with the board of Junior Achievement and the web agency. They went through their line-by-line billing and what they were offering and stuff like that. Turns out, they were being less than honest. They weren’t fully onboard.

One of the major things that triggered me was that they were building forms for this customer. Junior Achievement needed a lot of different forms for different types of things. But they were basically charging them to build each form from scratch. Each form was a new thing. I was like, really? Once you’ve built the backend to handle the heavy lifting, that’s something you do once. You build that once, and then the rest is front-end stuff. You’re just going to connect it. So, I was like, I was a little, I was like, I feel like this pricing is off. And then, I was noticing some other areas.

So, I told him what I thought, they fired the web agency, and then my CEO asked me to take the project on for Junior Achievement. So, Kevin and I started working on it, and one of the first things we did was stay true to what we thought was true about forms and built a reusable kind of form builder for them. So, they could build whatever frontend they wanted, and the backend processing was already taken care of. And that’s kind of what got us into the form space.

Now, at that time, Gravity Forms already existed. There were a couple of other form builders that already existed. But we didn’t know WordPress, like we weren’t WordPress people. We weren’t in the community. I had no clue about this product. So, we built it, and we thought, I wonder if anyone else would use this tool on this web platform that seems to be up and coming and growing. Let’s try. And thus, Ninja Forms was born.

Patrick: Oh, that’s very cool. That’s, I think that’s like the classic origin story in the WordPress world. A client asks you to build a thing, and you’re like, “Why don’t we just build a general form builder rather than building the specific PHP code for this one client that’s very specific to them?” And then, it just gets so much easier. And I know I’ve done that.

And oh, and just for the listeners, you and I have worked together in the past. I built some Ninja extensions. So, I love that you have the classic WordPress origin story. It’s perfect.

James: It’s true.

Patrick: I love that. So, in the WordPress world, one thing I like about it is there are a lot of tiny companies, right? There are a lot of solopreneurs or small partnerships. You and Kevin’s company, if you do get so and when you start out, you may not need a whole lot of leadership culture teachings because it’s just you and maybe one other person. But if you’re successful, you know, you’ll have a couple of employees, maybe doing support, or maybe doing development, or maybe doing marketing. And if you keep having more growth, then you start growing to 10 or 20 people, like Saturday Drive. 

So, my question is, how do you prepare your business for that growth? And at what point do you think about culture and leadership in a company once your product is successful? When do you think about that?

James: Sure, well here’s the thing: like when it comes to culture, every company, whether you’re one person or 20 people or 100 people, you have a culture. Every organization has a culture because it has people that have something that they share in common, one way or the other, and those things may be toxic and those things may be very positive. But every organization has a culture, and you either let culture happen to you or you intentionally define the kind of culture you want to build. Both of those are options, and I wouldn’t say that there’s necessarily a right way or a wrong way. But what I would say is, every time you add a person to your team, they are going to change your culture in some way, shape, or form. So the question is, when I hire, does the person that I’m hiring going to add something that we want to add to our culture, or are they going to subtract something from our culture that we don’t want subtracted?

And so I think of it a little bit like when Kevin and I started, we were best friends. We got along. We were people-first individuals out of the gate. That’s just the way we were. So our culture became a very people-first organization by default because it’s who we were and it’s who we hired. We hired other people who were like us and had those same kinds of values. The danger, though, of course, is sometimes you’ll hire solely for say talent and ignore culture. And that person, who may be a great talent and they may be a superstar, but they do not share the things that you value, they will morph and alter your culture for the worse if you’re not careful.

So I’m not saying don’t hire rock stars and don’t hire people who are just amazing at what they do. Obviously, you want to find those people. But you have to also find people who fit the thing that you’re trying to become or the thing that you are, you know you want to not take away from that. So I, again, I always look at culture as two things: it’s who we are and it’s who we want to be. So when I hire, I’m looking for that somebody who will enhance who we are or will add to us something that we are not, but we strive to be.

Patrick: So I have two follow-ups to this. The first one that I’ve, I’ve just, it’s just general business advice I’ve heard, is that your first employee matters a lot because they’re sort of the first. They will model what other, all, you know, so if you’re a partnership, you have two co-founders. In your case, your first employee might matter a lot because then all the next employees look up to this person and kind of what worked for them will kind of apply to all the people behind them. Do you agree with that? Is that accurate, that the first employee is really important?

James: Yeah, I think that absolutely can be true. And, and you know, it isn’t always a zero-sum game. It’s not always, like you, you hired the right person and they absolutely exuded what you wanted, and every other employee kind of saw that. Or even the negative, it’s usually a mixed bag, right? It’s usually they shared some qualities that you wanted and some qualities that you don’t, and you have to navigate that and figure out as a team and as a company, what are we going to reinforce and what are we going to, you know, push away and reject as a part of our culture? And, so there’s a content negotiation going on. But yeah, that very first hire, can be very dramatic, especially when it’s like, you know, when you’re one person or even two people, right? You’re, when you hire somebody, you’re basically, that’s 50 or a third of your culture right there, right? Right. So it is a huge impact. When you’re 20 and you hire one person who maybe is just a little off, maybe doesn’t have that dramatic, like, ripping effect or the culture is strong enough to sustain the damage comes from a little bit. But I, even with that, I would say, be very careful because it’s the little things that destroy us. It’s not usually the big things. The big things are obvious. We get in the interview, somebody says something, you’re like, uh-uh, not our culture, we’re not bringing them in. But the ones with those little things that will needle away at your culture over time, those are things you have to be careful about.

Patrick: Wow, I love that. So the other follow-up here is, when do you do because I guess I, you have to do internal work on yourself to realize because like, I think like culture is invisible to yourself unless you really think about it. It’s like, what are my values, and what are the values of my co-founder, and then what are the values we’re looking for in a hire? Don’t you have to do some sort of like internal work before you make your… it feels like a lot of upfront work to make sure that your first hire is really good, or is it not that much work?

James: For most people, it’s not that much work because they don’t think about it at all, right? Let’s look, to be clear, like we don’t think about it because we just started a business. We wanted to build a product, and it’s growing, and now we’re like, “Oh, we need to bring another engineer in,” or “We need to bring in somebody to handle support,” or “We need to bring in a good marketer,” or whatever the case may be. And you bring that person in because you have a need in the product, business process system, not necessarily in the cultural system.

You know, we’re at a place now when we hire, yeah, we’re hiring for a position, but we’re also hiring for the culture. Like, culture is more important to us even than somebody having the experience to carry out the project. So somebody can have a lot of experience, but we know that culturally, that’s going to be, we’re going to take a hit. They’re not even an option. I don’t care how good they are, it doesn’t matter. Does not matter at all.

So I would say that as your, as you’re navigating that and you’re thinking about culture in general, it is a lot of work, but you don’t generally do it until you realize you needed to do it, right? It’s when you, when you start bringing people on, you realize, “Oh, we turned into something I wasn’t expecting us to be,” or “Happy accident, this is exactly what I wanted us to be. These values are my values, and we want us, we want to protect and continue to reinforce that.”

So most people don’t do that work upfront, but the work is not actually all that hard. It’s a little bit of self-reflection. It’s looking at your life and saying, “What do I value? Like, what is important to me?” And the truth is, sometimes there are certain values that you have that are core to you, and they’ve probably been core to you since you were young, and they’ll be core to you until you’re old. And then there are other values that are more malleable, and they change over time based on the stage of life and various things. And so those can change, and so you want to figure out, again, what are the core values, the things that you want to be true always? Yeah, and stick with you.

Patrick: Love that. So, listeners, just over a year ago, I was on James’s podcast, and I will drop a link for that in the show notes so you can, you can go ahead and listen to that. And I actually just, because this is a cool opportunity to follow up, I want to follow up on something we discussed there.

So, we discussed transitioning from doing your own thing to working under someone else’s leadership. And from the opposite side, if you’re the founder, you start hiring someone. Let’s say you hire an SEO expert. This person might know more than you do about SEO. How do you, you know, give them tasks that they have to do, give them projects that they have to do, and, you know, set some sort of reasonable timelines, but also listen to them in areas where you’re not as knowledgeable?

Right. I’m just thinking of, like, in SEO as an example, it’s like, maybe this thing that you think takes 10 minutes actually takes four hours because, you know, you really want to get it right, and then everything else builds off of that, and it’s worth the extra time. Like, how do you, I think as a business owner, you might say they’re wasting time if you don’t know the process. How do you trust those people, especially when it’s technical or specialized knowledge?

James: So first, if you’re hiring somebody to take over a specialized position, I hope they are smarter than you, right? Because that’s why you want to hire someone. You want to hire somebody who’s better than you at the thing. It’s probably something that’s not your superpower and it doesn’t give you energy. So you’re wanting to find somebody who is their superpower and it does give them energy, and then you want to set them loose on that thing.

The second part is, I’ll tell you a story. When I was a kid, I wanted to learn how to play the guitar, and my brother was an amazing guitar player. He was a virtuoso. He could just, he could just, he had an ear for music. So he could listen to, like, the Metallica solo on his favorite song, and then 15 minutes later, he’d have it memorized and could riff it out and play it like nothing. He was a genius musician.

So what I wanted to learn, why wouldn’t I go to my brother who was amazing? And so I went to my brother, and I said, “Can you show me how to play guitar?” And he was like, “Sure.” And so he starts teaching me things, but he had forgotten a really important principle: that when you start, you’re bad, and you’re not going to be good. And so he became very impatient with me when I couldn’t change chords as fast as he thought I should be able to change chords in this early stage.

When you hire somebody new to take a position, one of the things leaders fail at, at times, not always, but at times, one of the things that we fail at is forgetting the fact that we didn’t always be great at what we do either. And so being willing to sit there and say, “I don’t actually have all the answers, and if somebody else fails, I failed.” And I didn’t blow up the business, and I was the only one, and I was in charge, and I made the most important decisions, not just a project decision or a marketing campaign decision. I made the most important decisions. And I didn’t blow up the business.

So being willing to let your just release control and say, “I don’t have to have all the answers. In fact, I hired this person because I don’t have all the answers.” If they fail, that’s a part of the experience that I want them to have. And I liken it to this way. I’ve said this a number of times to different people. When you’re in stunts, you know that you do, like, a big fall off of a building, right? They have that big inflatable thing that you fall into, right? Well, when I started my business, I didn’t have an inflatable thing to fall onto. If I fell, it was just over. There’s no one to catch me. I had no cushion at the bottom, right? Because I was bootstrapping it. I didn’t have anything. But for the people that I hire, I am that safety net. I am that inflatable at the bottom of the building. So I tell them, “Climb to the top and jump and have a good time, and know I got you. Like, if it doesn’t work out exactly the way you thought it was, I got you. It’s all right.” That’s my job as a leader, to encourage them to take risks and make the big plays and let that happen, and reassure them that even when it doesn’t work out exactly the way they want, it’s not the end of the world. We learn, and we do it again. Get back up there and jump again.

So yeah, I think the biggest lesson is, you know, I’ll give up, give up the control. Remember that you weren’t great at everything when you started. You hired them because they are better than you. And let them fail. I failed. And if they succeed, even better.

Patrick: I love that point about you being 12 steps ahead of someone you hire, or 20 steps, or 100 steps in front of someone you hire. So, I like that you’re number one, remember that people are farther behind in their journey than you, and give them the ability to fail gracefully and not without damage. Very cool.

Let me just ask you one other follow-up there. How do you build those safety nets? I mean, it sounds like you just have a built-in growth mindset, James. Are there leaders who don’t have a built-in growth mindset?

James: You know, it’s tough. I think I didn’t always have it when I first started. I needed to control everything because I felt like, one, I felt like I was smarter than everyone else. Let’s be honest, I mean, there’s a little hubris that comes with entrepreneurship. And so, there’s this little idea, there’s this little thing in the back of our brain that says, “I have this idea, I’m the only one who can carry it out, and I’m going to be successful doing it, and everyone just needs to take my lead,” right?

And I had that going into it. I remember having arguments online with people who are much smarter than me, and I was dead wrong. But I was new, and I didn’t know any better, and I had a lot to learn from that. So, there is this hubris and this little bit of this unstoppable mentality that entrepreneurs have when they go after it. And they need it because if they didn’t have it, they wouldn’t be entrepreneurs. It’s just hard to do anything without it.

And so, I wasn’t always in that growth mindset. I was, a lot of times, it’s my gut or nothing. Like, I know what we’re supposed to do, and I led that way in the early stages of the business for a very, very long time. Now, when I mentor other leaders in and out of the organization, and we have these conversations, and they’re like, “How do you let so and so just do what they do and let them go and not worry about it?” And I’m like, “Because it’s not important. Yes, business is important, and we want to be profitable, and blah blah blah, blah. But this one action, this one thing isn’t gonna make or break the business. Yeah, and so let’s learn from it and let’s have, let’s share that experience.”

I realize that my job is to walk alongside my team more than it is to walk in front of my team. We think of leadership a lot of times as, “I’m walking off,” right? And then there is a part of that, right? There’s a part of, “I’m out front, I’m gonna take the bullets, I’m gonna make sure that I protect my team.” There is a part of it that is that. But more times than not, it’s me walking beside my team, cheering them on, and just, yeah, just being a cheerleader. That’s one of our core values, and that’s because of that very reason.

Patrick: Well, let me know when you have a personal development workshop, James, because you seem to have grown a lot as an entrepreneur, and I don’t think we have time for this podcast, but that’s really inspiring. 

So, I do want to talk about culture in the WordPress world. In the WordPress world, I think one thing we’re almost remote by default. I mean, there are obviously lots of agencies that, you know, you start a business with a friend or a coworker or someone in the same city. But oftentimes, you’re working with people across state lines, across country lines, internationally, etc. And when you’re, and so I think working remotely is a challenge. And when you’re working on-site, employees can, you know, you can get together for drinks, you can have team-building days. You can, I actually remember one of my first jobs after college, my boss took the four of us and we went go-karting for two hours. So, just like, it was a very fun thing that you could do because we’re all on-site. He just said, “Hey, everyone, stop working today. We’re going go-karting.” Wow, okay. Like, you just can’t do that remotely, though, right? And so I was just talking with Vova, the CEO of Freemius, and they just met, basically. I think the entire team met at WordCamp Asia for the, I think, the first time. And he was saying that the impact on their team was incredible. How do you build a solid culture in a distributed company? Is the very long question?

James: Well, I have the unique experience of having done it both ways now. I’ve been distributed. Our company has been distributed since 2019, right before the pandemic. So, before the pandemic actually took off, we had already left the office. So, you would almost think that we knew it was coming, but it wasn’t that at all. So, we had just gone distributed. But before that, since 2014, we were, for five years, we were co-located in the same office. So, I have this kind of both sides, and I will say, I would never go back to a co-located office, having experienced the distributed, having experienced a distributed culture, never. But it is harder. No, I don’t think I would. And the reason is, it is harder. It is a lot harder. And I think what we lose, it’s not collaboration, it’s not passion or for the projects that we work on. It’s not a connection to the organization as a whole, but connection to one another is a lot harder in a distributed culture. And that is the thing that I’m constantly trying to figure out how to fix. And I can kind of reflect back to Vova, his opinion on having the retreat, his first-time retreat, and the impact that it had. We had our first one a year ago. We had our second one literally just last week, as of this recording. And the impact that bringing the whole team together has is amazing, right? But when you have it every single day, the effects of being in person actually start to wear off. Because what ends up happening is when you’re in the same office with each other day in, day out, yeah, you can go and get those after-business-hours drinks or have your party or play darts in the hallway or we did all those things, right? We had a ping-pong table, pool table, darts, drinking parties, for better or for worse. Like, we did all of those things when we were co-located. But you start to actually take each other for granted because you see each other every single day, and it’s just like, “Oh, that’s so-and-so, and that’s so-and-so, and they’ll always do this.” And there becomes a little bit of a familiar, almost an over-familiarity that sometimes, it’s a lot harder to kind of continue to build respect and hone respect for each other because you just get so familiar, and you become a little lazy in your interactions.

But there’s something about a distributed culture where you only ever really interact, mostly through text, that kind of protects a little bit of the over-familiarity. And so, there’s still a little bit of a standard of, “Hey, I want to present myself in a certain way, and I’m writing this out. People are going to be able to read this forever.” So, like, it’s not like I said it up off, you know, off-thing at the water cooler. But no, I wrote this thing in text, and it’s going to be memorialized in a conversation forever. So, I’m going to be more choosing of my words and be more thoughtful in how I communicate.

I think there are some things like that that are really helpful. Now, in order to develop a really strong distributed culture, and I don’t consider myself an expert on this by any means, but I have been doing it, and I would say our team feels, I believe anyway, if I were to bring my team across here, each one of them would say that we have a pretty strong culture, respect, and trust of one another. And so, the first part of that is trust. It’s a team sport. It’s a team effort. It’s not just a leadership thing, and it’s not just something that we should demand from our employees and not give as leaders of an organization. It’s a team sport. We do it. It’s back and forth, give and take. That’s a big part of it. And so, one of the things that we just, because it’s our core value of being people first, it’s just everything that we do is around making sure that we care about one another, that we’re taking that, we understand that when we work and we succeed, we succeed for those who work with me, whether that be on the other side of the ocean or in another state, that my success is their success, and their success is my success. And we just kind of have to cheer that on.

So, there are a few things you can do. Obviously, retreats are awesome, right? Getting together for a week is awesome. We go away from every retreat wishing it was longer. Yeah, we don’t do it longer because if we did, then people would be wishing it was over because you can go too long, right? So, a short, good one-week retreat is awesome. It’s energizing. People get connected. They get rejuvenated. They get reaffirmed that they are a part of this team. It builds connection and it builds relationships. And then, when they go back, they carry that with them as a fire as they communicate with these same people. They remember the conversation that they had over drinks late at night before bed, and they go, “Man, that’s a good person, and I really appreciate that they listened to me as I talk through my personal stuff.” And so, you build those connections.

I think, you know, there’s more that you can do. You can do that through calls online. You can do that with different kinds of team-building events. You can do that with small little meetups. It doesn’t have to be a whole company. Maybe bring a department together and let them, you know, go on a trip, go to a conference, and meet up. WordCamps in the WordPress community are a great place. We used to do that a lot. So, there’s a lot of different ways of building that community, but it really comes to finding ways. And every culture is different, so it depends on your culture. Our culture is people first, you know, being a positive force, being a cheerleader, embracing fun as much as often as we can, and making whatever we touch better. Like, those are our core values and our main components. And so, for us, that’s constantly reinforcing positivity, trust, and respect.

Patrick: So, your answer there just made me think of two things. One was an experience I had. I was working at Woo Themes at the time, and there was this person who recently joined the team, and whenever I said a thing, they’d be like, “That’s a bad idea,” and I was like, “Ah, they’re so rude.” And then I met them in person, like two or three months later, at their company retreat, and they were actually one of the smartest people that I’ve worked with, and they were just very blunt. And eventually, I think you learn how to read someone’s texts. You hear their voice when you know them. You hear their voice, and it’s not, “That’s a bad idea,” it’s like, “Well, that’s a bad idea.” It’s a little bit softer once you know that person’s voice and how they speak and also what they’re like in person. So, I think number one, that’s a huge thing, is just you definitely prevent miscommunications. Right? Like, you hear that person’s voice, and it’s always softer and less mean than you think it is.

The second thing you reminded me of is that I love my family, but I feel like I really enjoy my family more when I see them once to twice a year. Like, I look forward to it, to my family every day. I’m like, “Oh, they do this thing and annoy me.” So, is that the right comparison with working in the office every day? If things people do are annoying or frustrating, and you don’t take them, you don’t appreciate them? But then, you know, when you see them twice a year for vacations, you’re like, “Oh, I can’t wait to see, you know, my extended family.” Is it like that?

James: I think that’s a fair assessment. When you’re with them every day, it’s a pet peeve. When you see them twice a year, it’s a cute little quirk, yes, right? Like your tolerance level for those things is a lot greater when you don’t have to experience them every single moment of the day. And so, yeah, I think that is a pretty fair assessment on that. 

Patrick: Cool, I love that. All right, so moving on, I had a question about the culture of WordPress. Lots of people in the WordPress space and just online, maybe programmers, they’re probably slightly more introverted than extroverted. My question for you is, if you are an introvert and you’re a founder of a company, do you think that’s a challenge that is key to overcome, or is it a strength that you can use to build your culture in a more introverted way?

James: Yes, and so a little secret, and most people don’t know this out of the gate like they don’t notice it when they talk to me, they’ve seen me speak at WordCamps or conferences, they’ll see me at after parties, and I can get in the middle of the crowd and have a good conversation with a group of people, and I’m not shy about it. And yeah, I am an introvert. I don’t get energy from any of those things. Those things sap my energy. Matter of fact, after this podcast recording, I’ll probably take a 20-minute nap just to recover from this conversation. So, I’m a bit of an introvert. Right? I can understand that it is both a superpower and a challenge, and I think you should look at it both ways. In some ways, it’s a challenge to overcome because, one, we don’t want to just always be limited by the things that are true about us, and so we should always look to get ourselves outside of our comfort zone. I’ve learned to be comfortable public speaking even as an introvert. I have learned to be able to get in front of my team and cast a vision and communicate ideas in front of my team and find comfort in that. You can do that while being an introvert. Those are still things possible. You just have to learn how to communicate, read books on speaking, listen to people talk about communication, and you can hone those skills and strengthen what might be considered a weakness for you. But on the flip side, if you are an introvert, you also don’t have to be the face, even if you are a founder. You don’t have to be the face, right?

You can team up with people, so this would be my suggestion, right? Maybe you’re somebody who’s like, “Man, I hate getting in front of my team and having to cast a vision or put forth an idea.” Well, do you have any communicators or marketers on your team? Pull them in one-on-one, right, and have a conversation with them and help them spread your message. Have them come up with the ideas and how to do that in a way that maybe doesn’t require you to get in front of their face. Or try recording a video where no one else has to watch it. You just record a video, so it’s like, “I’m not in front of anyone, I’m recording a video,” and I can edit it down to where it’s perfect and says exactly what I wanted it to say, and then just distribute the video. You don’t have to, like, there are ways to get around the fear of being in front of people and talking in front of people, or even just the drain of energy, the energy drain of doing it. So, there are a lot of different ways that you can approach this. I think it can be a challenge. I think it also can be a superpower. It all depends on how you want to approach it.

Patrick: Yeah, that reminds me of—I’m sure being an introvert has some incredible superpowers as well as some challenges. Just like there are pros and cons to that, yeah, I think figure out how to make it work for you. Cool. 

James: Yeah, I think that’s really what it comes down to—making it work for you. Not every introvert is the same, you know, so some introverts can get in front of a public and speak, right, and some can’t, and that’s okay. You just have to find out where you’re strong and where you’re weak, and yeah, lean into your strengths. Don’t shy away from your weaknesses. Always strengthen, but you’re gonna get more results by leaning into your strengths.

Patrick: Love that! So, I’m gonna quote you here, and I think this is from your site, maybe from the podcast. It was, “Most organizational issues stem from misaligned culture, not individuals.” So, my question for you is, what points to a misaligned culture, especially in a remote environment, and how do you remedy it? How do you know your culture is misaligned?

James: Well, so being a people-first culture, right, the quote comes from the fact that we are a people-first organization at Saturday Drive at the core. And so what we have to, what the trap people can fall into, is when something doesn’t go the way they want or if a person isn’t acting the way you think they’re supposed to act, it’s really easy to think the person is the problem. And because we’re people first, we like to step back and say, “No, no, let’s look around the edges. Maybe there’s something in our culture that we’ve reinforced. Maybe there’s a lack of clarity. Maybe there is a lack of trust. Maybe something has broken down in communication. Maybe there are some unspoken expectations on either side that are poisoning the relationship.” And so we like to look around the edges a little bit and not immediately go, “People are the problem.”

In most cases, you know, I’m not saying it’s not true, there are… There are exceptions to every rule, but in most cases, people are adults and just want to do their best work and want to be seen as doing their best work. And when that’s not happening, it’s not necessarily because the person doesn’t want to. And so I don’t think there’s a person, it’s not necessary. Now, there may be a personal people alignment in that person not in the right role in the organization, that may be true, but that still, to me, is a culture problem. Because I can move you into a different role if I’m keeping you in a role that’s unhealthy for you and you can’t shine in, that’s a culture problem. That’s not a person problem. So I kind of look at it that way.

Here, here’s the way I think you know, every again every culture is different, so it really does, a little bit, depend on what the particular organizational culture is to determine when it is out of alignment. But I can give you an example in our organization. In our organization, we know that there is a culture problem when someone jumps to the negative conclusion every time, huh? ‘Cause we’ve tried to establish a culture of respect and trust first. And so, the assumption being a cheerleader and being positive, there’s a nature of assuming the best out of the first as the default until, you know, it’s kind of like innocent until proven guilty. I don’t assume you meant the nasty thing until I’ve dug a little deeper with respect and care, and you’ve proven to me that you meant the nasty, ugly thing.

So, if somebody is immediately saying, thinking something happens in the organization or a decision is made by a leader, or whatever, and someone immediately goes to the negative worst possible, you know, ah, they don’t, you know, they don’t believe in, you know, giving empowering the team members, or they don’t, blah blah, or they just want to make everything has to be their decision, or whatever the case may be, when that starts to happen, we’ve got a culture problem. Something’s happened and that may be, that could be an individual problem, but it’s probably, it could be that individual cultural problem, right? That they are not the right person in our culture and we had a culture misalignment. We hired somebody who does not share our people-first or be a cheerleader, our embrace fun, our make it better values. And so, I don’t, I don’t even though it may be an individual person who doesn’t share our values or our culture, I don’t necessarily still see that as a people problem. That’s a culture problem, and that may be that a person is in the wrong culture, right? We have added somebody to the wrong culture. But it’s not necessarily, I don’t, I don’t necessarily begrudge a person for having that view. I don’t know what their life has, where they came from, what kind of reasons they have, distrust, and all those things, like they may have valid reasons for all those things, but that’s not the right thing for our culture.

Patrick: So, let me ask you about shaping culture because I, you know, how do you coach the person or work with a person to see[]if they fit your culture, and then how do you go, “Man, we tried X, Y, and Z, they’re just not the right fit.” Is that a fair question?

James: Yeah, no, I think it’s a fair question. You know, and I will say for us, we’ve been to the extreme. So, we extend a lot of grace and a lot of time, maybe even to our detriment at times because we’re people first. So, we really try hard to go the extra mile to give everyone, any person, any individual all the grace and support they need to get there because we understand that we all go through different things in our lives and there are different seasons that cause us to act the way that we act.

I think in the end, it comes down to just being transparent and honest and giving that feedback. You know, it actually, in a way, comes back to the introverted question. A lot of times when we think of extroverted, introverted, we think extroverted is this idea that we think that leadership has to be big, boisterous, talking and shaping the business by talking to the crowd. Real leadership generally happens one-on-one, and an introvert shines really well there. And so, one-on-one, you have that conversation, and you can start to shape your culture by shaping individuals and finding common ground with those people.

So, if there is a person in your organization that feels like there’s a culture misalignment with that individual, I think that one-on-one conversation, really getting into, not usually about the work, it’s about the person. It’s like, “Hey, why did you come to this conclusion? Why do you feel this way? What have we done to not instill trust? Or what has happened to you in the past that you’ve brought baggage with you into this organization that’s causing you not to trust? And how do we deal with that? How do we navigate that?” Because that’s not, it’s not, we’re not gonna get anywhere if we have that, again, trust is a team effort. And so, part of leading somebody who lacks trust is putting yourself out there first and giving that trust to that person so that they can see it demonstrated. And you can kind of make yourself a little vulnerable and say, “Listen, we can work this out, but we gotta, there’s gonna be give and take, and we gotta figure out what’s going on.”

Now, there are times that that’s not possible for, for whatever reason and then in times, you have to cut ties and that’s this way. But you still, even in those situations, you try to do it in such a way that instills trust, that says, “Hey, this is respect.” We’re not gonna, you know, we always do long severances and things like that, so that people have a long runway to make transitions or whatever the case may be, because even if there’s a cultural misalignment, we’re still people first. And even a person who doesn’t think that we want the best for them, we want to give them the best opportunity.

Patrick: That’s, I’ll just give you, I will give you a little compliment here,it seems like you treat people incredibly well, even when they’re leaving your company, and I think that deserves some kudos. So mini congrats halfway through the episode.

James: I appreciate that. I don’t, I don’t know who everyone who has ever left our organization would agree with, but I certainly know we tried. We may have fallen short at times, but we have always tried.

Patrick: That’s awesome. So let me ask you the flip side, how do you know you have a healthy culture? I mean, if there is such a thing as healthy, I don’t know how you define healthy, but how do you know you have that? 

James: For us, I’ll tell you the key indicator for me in Saturday Drive is when people go out of their way to help someone else in the organization without the instruction of leaders. Anyone in the company sits down and says, “We’ve got this project, so-and-so is having a problem with this. Hey, you know, Andy, can you help them with that?” And Andy’s like, “Sure, I can.” Right? Like, because a leader said that this was a problem. But when team members self-identify problems that other team members are struggling with and then go out of their way outside of their ownership or their responsibility to help someone else achieve whatever it is that they’re trying to achieve, that’s always a really good sign that our culture is firing on all cylinders. So that’s one of the things that I look for and I’m always the most encouraged about.

Patrick: That’s really cool, okay. So, I like that interpretation of culture, if a problem comes up and someone already started working on it before being assigned by their manager, that would mean that the value is communicated, they understand it, and they’re acting without being instructed. That’s a good indicator?

James: Yeah, I think that’s a valid thing when you have put an ethos into your organization and that ethos operates without you having to pull strings and puppet master that ethos. Yeah, I think that’s when you can tell you have a really good culture. It is self-operating. It doesn’t require you to, it doesn’t mean you don’t nurture it and don’t continue to encourage it and all this stuff, but you’re, again, you’re playing more the role of a cheerleader than you are an orchestrator. Like, orchestrators have to go in and tell people, “You go here and you do this and you do that.” But when you get to operate as a cheerleader, like, “Thank you for doing that, and I saw you do that thing, and I really appreciate when this team did this thing for this team,” and those things are happening, like, that’s when you know you’ve got something really good, and you’ve got people who care about people. Like, they, it’s beyond just the job. It’s beyond like, “I got a job, I’m getting paid for it, so I gotta do it.” The people are going outside of their comfort zone or they’re going outside of the responsibility to live the ethos, almost on autopilot. That’s a pretty good indication you’ve got a strong and healthy culture.

Patrick: Love that. 

James: That can work in the opposite too, though, right? Sure, people are absolutely doing the negative things on autopilot. That’s probably also another good indicator you have a poor culture.

Patrick: Love that. So how do you hold yourself accountable to maintaining and building culture? Do you set aside two hours on a Monday morning? How do you hold yourself accountable? 

James: So there’s a couple of things that I would say we do. One, we get a lot of feedback from the team. So we do ENPS surveys, we do quarterly checkups where we get information. 

Patrick: PS service? 

James: ENPS, oh, that’s a fair question. So most people in the product space are familiar with NPS, right? Net Promoter Score. And ENPS is just employing that Promoter Score. So if a Net Promoter Score for a product is, “How likely are you to recommend this product to another individual?” That’s usually the question you would ask to score that. The question we add that we ask for an NPS is, “How likely are you to recommend somebody else come work for our company, basically come work alongside you? How likely are you to recommend that?” And so we do that survey. We do what we call fitness checkups. We do fitness, you know, fulfillment surveys to see how fulfilled individuals are. We do a lot of feedback to hear from the team how they’re feeling about the work that they’re doing. And the key element here, especially from a leadership perspective, is taking that feedback, acting on that feedback. But what’s the core principle underneath that is being open to critique and criticism, building a culture as a leader? If you want to be accountable, you have to have a culture where your team feels not just comfortable, but almost expected to challenge and critique and criticize when things aren’t going the way you said the ethos is supposed to go. So I love it when a team member says, “Hey, we did this thing, and that didn’t feel very people first.” Okay, right? Like, we need to listen to that. So there’s this idea of being able to be humble and approachable and creating and establishing the first key part of the culture, which is open to criticism, open to critique, and almost making it a mandate that it’s everyone’s responsibility to protect the culture. I think that, to me, the chief issue is that I need to, in order for me to be accountable, my team has to be able to question when I don’t do things that fall in line with what we said is what we do. 

Patrick: Yeah, so there’s this concept that I read about, and it was called psychological safety, which is basically, do you feel comfortable giving feedback to your boss, negative feedback? Obviously, positive feedback is fine, you know, and I’ve definitely worked at places in the past where there’s, it’s one of those things where there’s like unsaid rules or there’s, you really have to do this thing even if it’s against what the company says that they’re for, right? This is not people first, but we’re a people-first company, but this action is not. So, I think what, so like, I think you want to have a workplace where everyone feels like they can bring up miscommunications, challenges, or critiques with their manager, obviously not to the point of always criticizing the manager, but you want to make sure that healthy communication is there and people feel safe to bring up conflict. I think that’s a good way to know that you’re maintaining it.

James: Yeah, I think that’s a good way that you create accountability and you know that you have an accountable cultural community, a cultural organization, right? Is that when people know they are not only allowed to talk to their managers about things that aren’t working out, but are actually right. I’ll give you a funny example, it’s not a super serious one, but it is a pretty good example. Our number one core value is people first. We were sending out a package to everyone on the team. It was just a gift package of a lot of different things. And somewhere in operationally, we had somebody had made the decision that because one of our people was overseas and it was actually a real challenge to get it through customs, and it was more expensive to ship it, that we would just give them the money, the value of the package, right? Not a bad thing, it was meant out of a pure heart, like we want to make sure this person gets the value of it. But one of the people came to me and said, “I didn’t feel good about this because the part of this package is to feel connected, like we are a part of something together. And just getting money for this package, when we do stuff like that all the time, to just get the money, doesn’t feel like it’s on equal billing or equal footing with the rest of the team who’s getting this package that has all this stuff in it and it’s really nice.” So they came to me and said, “Yeah, I don’t feel good about it.” I’m like, “You’re right, I agree with you. Let’s make sure we never do that again and let’s fix that.” So it’s kind of a silly example, but it is an example of like, “Hey, we did this thing. It was even out of good intent. There was never any malice, but it wasn’t our value. It wasn’t what we said we believe in as an organization and how we care for our people. We need to be better.” And so we have strived to be better ever since.

Patrick: I think that’s a great example, James. I love that people have that psychological safety. You’re always working on the culture. Every time you talk with someone, there’s an opportunity for a little bit of feedback here and there throughout your day, throughout your week. So I love that.

James: 100%.

Patrick: Cool. So one more question about distributed companies. So they’re, you know, so distributed companies are different nationalities, different cultures, different beliefs, different time zones, different social cues. There’s a lot, like, you know, I think people in California and Texas are very different from each other. Imagine, you know, the rest of the world, right? How do founders manage that global conflict and miscommunication? How do you? Because that’s a lot.

James: Yeah, I wish I had like this really great answer for that because I just feel like I haven’t experienced a problem there yet, and I don’t know if that’s because of the nature of trust and respect that we’ve developed as a team, or we just haven’t butt up against it yet, and I don’t know. I mean, having been doing this for a long time, you would think we would have butt up against it, but we just haven’t. What I will say, there’s a few things that I can say to this. A long time ago, we had our PTO policy we used, and we were all co-located. We had a calendar just like a bank would have a holiday calendar, right? These are the days we take off for holidays and blah blah blah. And then we started to realize we had some people who didn’t observe the same holidays, and so we started making some concessions and changes there. And then you start realizing, wait, when you start going distributed, you have people from other cultures whose days that are important to them are very different than the days that are important to us in the States. So how do we handle that? So we actually moved to a big generic PTO policy of, I think, it’s now six weeks. So everybody gets six weeks of PTO, but we don’t have holidays. Take whatever day you want off. I don’t care what it is, whatever day is important to you and it’s an honor to you, and you can talk about it if you want to and let people know. You don’t have to, though. You can do whatever you want to do. So some of it is just giving people autonomy to live the best version of their lives in the culture with which they live that’s respectful to them and letting them do that. So we don’t, I don’t care if people work nine to five or two in the morning till whenever. I don’t care. I’m not looking for eight hours a day.

We have objectives that we’re trying to meet, and we’re looking to meet those objectives. And I don’t care if it takes you two hours or 20 hours. You know, actually, I do care if it takes you 20 hours because I don’t want you burning out. But, so you know, we’re pretty mindful and we’re pretty autonomous. Now, we’re privileged. Not every company can do that. Like, it depends on, you know, if you work in a manufacturing job or you have a restaurant, right? You can’t be that flexible.

We are very fortunate that we can give every team member 100% autonomy. That means they work when they want to work, when it’s best for them to work. They work around what’s important to them and they fit that into their schedule. Um, but a lot of it is just coming down to saying, “Hey, we’re all different. Uh, we have different perspectives. And if you, if somebody says something culturally that you think is off, you have a right to question it. But we ask you to question it in kindness first because I don’t know every culture. I’ll be honest. Right? Like, I am a 47-year-old CIS white male. Right? I have been brought up in a certain conditioned life. I’m ignorant of a lot.

Now, not the nice part about it is, I think everyone in our company starts to recognize we’re all ignorant on something. Right? Somebody’s culture, somebody’s ideal, somebody’s religion, somebody’s whatever. We’re all ignorant about something. So the idea is, since we know everybody’s ignorant, when somebody says something, you don’t assume it’s malice. So it’s ignorance, and ignorance isn’t mean always. Ignorance is just ignorance. So somebody says something, we call it out. We say, “Hey, usually I try to say, do that privately first.” Right? Because you don’t embarrass people if somebody doesn’t know that they said something that was bad. And then you call it out and they feel really stupid, like, “Oh my gosh.” Like, try first privately. If it doesn’t work, then you can, you move up channels. There are ways of handling and communicating. But I think most of it is just respect, assume the best, recognize that we’re all different, we’re all ignorant, we all have blind spots.

Patrick: Love that! So, you’ve had a long journey already. Um, what is the most surprising thing you’ve learned about yourself, as a business person, and how can it help someone who also wants to be a business person someday? 

James: I think there’s a level of discovering who you are that’s really important in business. And when I got started, I thought it was about solving the product problem, um, having an idea. I thought I was an idea guy, and I do, and I am an idea person. Like, I have lots of ideas, and I can’t, and I, I can paint a picture and cast a vision, and that is one of my strengths, that’s part of who I am. But the part that I really care about, and I didn’t discover, um, when you think about books like “The E-Myth,” like “The E-Myth Revisited,” where it talks about, like, one day you started out doing a thing that you love doing, and then you realized somewhere you became an administrator, a business person, and you’re no longer doing the thing you love, you’re managing people, and you feel miserable because of it, because that’s not the thing you started out to do, right? What I discovered about me was when that flips, when that switch kind of flipped, and I realized I’m no longer doing the thing I set out to do that I thought I loved, I’m managing people, I turned out it was people that I actually loved in the first place. And so it wasn’t about the product. I almost don’t care about the product. Like, there are products that I have, and they’re interesting to me, and they’re, I like solving problems and tackling puzzles. But it’s the people who use the products and the people who help me build the products that are really important. And that was a part of my kind of self-awareness journey, that I can be pretty happy building almost anything as long as I’m doing it with people who have mutual respect for each other and doing it for people who I’m solving a real need for. And so, that perhaps was maybe the biggest surprise to me, is that at the end of the day, products, business, whatever, I just want to serve people with people.

Patrick: Well, that is a perfect note to end this on. Thank you, James, for so much for being on plugin.fm. 

James: Well, thanks for having me. It’s been a lot of fun, and hopefully, I can do it again sometime. 

Patrick: Awesome! On plugin.fm, we sit down with exceptional product entrepreneurs and business owners who share their unique stories, as well as actionable tips and strategies based on their own first-hand experience. If you enjoyed this episode, head over to plugin.fm to check out our previous episodes. plugin.fm is brought to you by Freemius, your all-in-one e-commerce partner for selling software plugins, themes, and software as a service. If you’re struggling to grow your plugin revenue, send a note to [email protected] to get free advice from the Freemius monetization experts. My name is Patrick Rauland, and have a great day, entrepreneurs! Bye.

Thank you.

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