The Introvert’s Journey to Success Beyond Being a CEO

Matthew: The Introvert’s Edge Podcast was designed to create a dialogue around introversion. To stimulate a discussion around our disadvantages, how we overcome those disadvantages, and what we consider our introvert’s edge. Together we’re finally going to confront the stigma around introversion. Showing that we’re not second-class citizens, we’re just different, and we need to embrace that.

Introverted Leaders: Do You Really Want To Be In Charge?

Hello everyone and welcome back to The Introvert’s Edge. I’ve been speaking with Jason Cohen of WP Engine, who is the founder and CTO of a company that’s taking the world by storm in WordPress hosting. And he’s been sharing some amazing value about how he validated his idea and really tested with real people and wasn’t afraid to get told “no”. As a matter of fact, was happy to get told “no”, and a few ideas that saved him a lot of heartache.

But to that, now we’re going to really go into depth. I asked Jason to really think about some of the strategies that as he was growing this really successful enterprise that as an introvert perhaps he struggled with, and some of the strategies he used to overcome some of those hurdles and obviously obtain a successful outcome. And Jason, as a lot of introverts, love to prepare. So I’m going to really just turn it over to you, Jason. Thank you very much again for joining me on this episode. And look, I really appreciate you taking the time to really think about the strategies that you feel would really benefit introverts hoping to be the best business leaders of one kind or another. So I’d love it if you just share those so we make sure that we get all of those out, because that’s really what the introverts are watching the show for.

Jason: Yeah, well, I think the single overarching message I would say is, I feel like introverts tend to assume being introverted as bad and what they need to do is get over it or push through it or something. No one thinks they’re going to turn into an actual, genuine extrovert. No one thinks that, but you should try to be more extroverted because it’s better. And so to me the biggest message is, that is not true.

Matthew: Definitely. I couldn’t agree with you more.

Jason: It’s not true. So I would put it this way, because obviously introversion and extroversion is a dimension of a multidimensional thing of people’s skill sets, personalities, strengths, and weaknesses, whatever you want to say. It’s obviously one thing. So of all of these things, there’s something that’s true. And you can see it in diets. There’s diets, fads have been going on forever. There’s all different ones. There’s only carbs, there’s no carbs ones, it’s all fat, no fat, they’re everywhere.

What happens is some diets work for some people, that’s it. And some don’t and one person swears by it and then the person’s blah, blah, blah. And like, that’s how diets work. Maybe they’ll work, it depends on the person. And so that’s how advice is on the internet, whether it’s about introversion, whether it’s about other stuff, if you can always find someone that says, “Oh yeah, you gotta do X, X is very important.” And then someone else will say actually the opposite, “X is either not important or actually you should do the opposite of X. And let me prove it with this story of success with doing not X.” Yeah. And that is true of everything. Introversion, extroversion, dah, dah, dah. And so what that tells you is it’s not about introversion is bad or good, it’s about I need to understand who I am.

And then I need to find whether it’s techniques or advice or career paths or whatever which match me. Because there isn’t a right or wrong there, but there is a mismatch. There is such a thing as saying I’m going to be an event planner and introverted. That’s probably a mismatch because it’s hard to be both of those, but this doesn’t mean one’s bad or right. It just means that of the huge universe of stuff that is right for you, I mean of course 100% of all jobs are all career paths are all things, of course 100% is not right for you. That’s just silly. So the only question is which one is right. And not like, Oh, I’m bad because event planning isn’t one of them. Like, that doesn’t make any sense. Of course there’s all these people. And that’s why it’s great to have really valued diversity. This is part of why we value diversity because there’s all this different stuff and it all needs to be done. Someone needs to be a great event planner and someone needs to be great at diving into some weird bug for eight hours and emerging with a fix. We need both of those things and it’s going to take very different people to do it. Exactly, that’s why you need a whole bunch of people. That’s not why you want everyone to be switching around and doing all these things, that’s silly. The same way it would be strange to be a famously hard headed boss one day and a person speaking about flexibility the next.

So once you realize, introversion isn’t bad, it’s a proclivity, it’s a direction. It’s a strength for certain things, and it’s a weakness for certain things. So I should design my life around doing things in which it’s a strength, not 100% because the world isn’t so binary. But generally speaking, the thrust of it should be.

Matthew: Definitely.

Introverted Managers: Do You Actually Want a Leadership Role?

Jason: So there’s lots of things like that. And certainly in CEOs or founders or both, you find a wide variety of introverts and extroverts. So clearly being CEO or being founder is not one of the things that being an introvert says you can or can’t do. But there probably are things that are consistent or inconsistent with that. And that is the key, to find the advice and the things that are consistent with that.

So for example a lot of introverts want small talk to have a business where they make the most money, but not the most employees. Perfect. So that means you want a small business with maximum profit. And there’s all kinds of things that can come from that, like what kinds of products work that way and which don’t.

So for example, something that requires a big call center is not going to fit. And again, that doesn’t mean your business is good or bad. That’s not the point. The point is you’re trying to make something that fits so it can’t require that. So maybe it’s a product that has no tech support, maybe zero tech support. Okay, well that turns into a certain kind of product. Don’t worry, Google doesn’t have to export either. It doesn’t stop you from doing all sorts of things. It’s just one of those things. And you can start putting up these restrictions; and I’m good at writing code, or I’m good at design, but not this, but, but, but, but okay, well then it needs to be a product where the thing you’re good at is important.

So for example I’m terrible at design, but my previous two companies absolutely did not need to be designed to be successful companies have beautiful design. In fact, our website was so hideous it had broken images like in the homepage, that’s how crappy it was. It made millions of dollars a year with broken images on the homepage. So clearly design was not important for that particular company. And again, that’s not trying to say design is or isn’t important at all, or it’s not saying any of that. It’s just saying, well, what kind of business works with the constraints that I have. So by being first of all, introspective and honest about these are my strengths, these are my proclivities and whatever. Okay. Well then those become constraints. What kind of business? What kind of product? What kind of market? What kind of customer should I be targeting? Also what advice should I actually listen to? There are books, there are bloggers, there’s people like you and me who tell people what to do.

All right, that’s fine. But again, with these constraints in mind, you can think, okay, well I’m going to find those few gurus or mentors or advice givers that match me. Not because the other ones are wrong or smarter. It’s not that they match me. If they match me, then maybe a lot of those techniques will be right for me. Perfect. So that’s my goal is to find the ones that match me.

So that’s just not just introversion, that’s just in general, that’s the idea. So then you can start asking, when is introversion good? So for example, one is you can go deep on something, on content, and that could be building a product, writing code, designing something, art, writing words like content, or going deep on a thing. Physics, you can go deep on physics. There’s a lot of things that can go deep on, that’s pretty broad. Because an extrovert derives energy from being with people and interacting. Whereas an introvert derives energy from not doing that, thus focusing on something that means you can focus and go deep. Amazing. So focus and go deep, that’s one thing.

Another thing is a person who is introverted, people can often tell. Oh, you’re nervous, you’re awkward, you’re this, you’re that, you’re not a natural storyteller, you don’t form friendships quickly, it’s often obvious to others. So someone who is deep on something, but is nervous and awkward, is often called like a geek or a dork or something like that. These are words we use for that, right? That is super endearing. The truth is, most people love that kind of crazy, a little awkward, but deep smart on a one topic person.

Matthew: I’m happy to be geeky.

Jason: If you think about characters in a movie that people like, a lot of times they’re that, actually. Sometimes it’s Han Solo. Okay, fine. That’s fine. But sometimes the geek thing works too, in a lot of ways. And so that’s actually a good thing. That’s an endearing quality to be nervous and awkward with people, but deep on something. So you can use that.

Inspiring Trust as a Leader, Even When You’re Nervous

Or another example onstage, for example, some people conflate being on stage with being extroverted. That’s not true at all. Lights go on, you can’t see anything, you’re alone. You’re very alone on stage, actually. You want to run or just close shop. That’s a very lonely place, everyone’s looking at you. And so on. Nevertheless, you know I remember talking to someone once who was going on stage at Businesses Software, which is a big well-known conference and people like Seth Goden speak at it. And this person, I won’t say who it is, but they were nervous. They were throwing up the night before kind of nervous. So legitimately nervous. I said, “Listen, this is what you should do. You go on stage, and the first thing you say is, “I’m really nervous. I was throwing up all night”, say that.”

Matthew: Everybody would just naturally warm to him. It’s a way to readily inspire trust.

Jason: Of course. You think someone’s going to go, “Well, then you suck”? It’s really, that’s the reaction. Of course not. Of course everyone’s rooting for you. What kind of environment do you think this is? Everyone is rooting for you. When you’re vulnerable. When you say the truth and you’re vulnerable, that’s a magical moment. And suddenly you win the room. And then guess what? So then you’re awkward and you stumble over a word here and you lose your place there with the slides. Guess what the whole room thinks? “Oh, it’s okay. Hey, it’s fine. Just move on.” No, one’s worried about it. In fact, they’re encouraging. That’s what they’re doing. So maybe it’s a generally slow start, but you’ve just dispelled and won over the whole room. And not because you’re an extrovert, you just told the truth and we’re vulnerable. That’s all you did.

So as an introvert, you can just do this anytime. So you’re in an interaction, or at a party, or in a meeting, or whatever interaction it is that you don’t like that it’s hard. You’re repelled, repulsed. It’s hard to get the energy, et cetera, all those things that you would say. So what do you do? You use this technique. This is hard for me because I’m actually an introvert, so this is taking me a lot of energy just to sit here and look you in the eye right now, as weird as that sounds. Also, I’m the introverted CEO of this business. That’s crazy. That’s awesome. That’s a great way to start, like, boom.

Matthew: Yeah. Like, now I’m trying to help you get through it.

Jason: Now does that mean now I’m an extrovert? No. Does that mean it’s easy and I have all the energy in the world for it? No, it doesn’t. It’s not like you’re “solving”. And again, you shouldn’t ever think of it as solving the problem. What you’ve done though, is you’ve won over the other person, not by a trick but actually by the reverse, by being honest to them, a good reason. A real relationship reason by being honest and vulnerable. So it’s an easy technique, at least easy to say, maybe you have to get up the nerve to do it.

Matthew: We’re always worried about being vulnerable, though. And I think the biggest leap for me is when I realized that the more vulnerable I was, the more people respected me, wanted to work with me, and loved being involved in things that I was doing.

Jason: It’s a magic trick that works. And by the way, let’s suppose you run it. I say always, that’s a big word. All right, fine. So let’s say you run into the person and you tell them that, and they use it against you, or it’s bad. First of all, that’s kind of weird to think about, because most people wouldn’t do that. But okay, this is great because they just failed the test. You just never want anything to do with that person. And now you know that. Great, you’ve learned something. Don’t work with that person. They’re wrong, you are right. Run away, that’s fine. But how many people are going to do that? It’s rare.

Matthew: I couldn’t agree with you more on this. This is a really powerful conversation because when I first started doing public speaking, from stage, I have really poor reading speed. So when I put slides up and I have to go with slides, I’m always freaking out like I’m going to miss a word. And because I’m introverted, if I make a mistake, it freaks me out, so then I pause. So I started telling people that I have a really slow reading speed in my speech, and that I’m introverted. And as soon as I did that, everything changed. It’s like everybody’s facial expressions were relaxed. It wasn’t, “What’s this kid got to teach me”, it’s “Oh, this kid’s obviously really good if they’re going to get him to speak, even though he’s not a professional speaker and I’m really open to hearing it.” And I, all of a sudden, I stopped making mistakes because you’re less nervous. It was just empowering for me. So I think that’s incredible advice.

You Deserve to Feel Fulfilled at Work

And I want to swap though to another topic, because one of the really impressive things that I noted about you when I saw you speak at Small Business Festival, you’re a person that built a business from the ground up. You got it to a sizable number of staff. I mean, 50 to 70 people is no small feat. And then you moved into the CTO role. And a lot of people would say, well, maybe it’s because he was an introvert that he picked that role. And then other people would say, well, perhaps he should have pushed through to become the CEO of his own company. This was a real logical decision. It had nothing to do with introversion, but I think a lot of people would let their own experience with introversion play a part in making that decision. So I’d love for you to share how you made that call and why it was so important, the way you made that decision.

Jason: Well, everybody deserves to be fulfilled at work. That’s just something we should want for everybody. Right? We should strive for it. And if you’re a CEO or a founder, shouldn’t you want that for all your employees? But it also includes yourself. And so what does that mean? So generally it means that you are in a position of strength. Sure, you’re growing and growing means you’re not good at it yet, that’s what growth is. Maybe there’s a historic financial storm or a housing market crash in the distance or something like that to deal with too. But fundamentally starting in a place of strength and enjoying the work, more or less, you can’t enjoy every day but there’s enjoyable, fulfilling parts and the company needs it. This is a role that the customer company desperately needs because it drives important things. So the intersection of that is where people don’t burn out and they’re excited to be there, it’s fulfilling, it’s all the good things. So I’m a great CEO and the company is small, like under 50 people, under 80 people, something in that comfort zone. If only introversion ruled the day, then 50 would be too many.

Matthew: Definitely. Twenty would be too many.

Jason: So this is not just an introversion thing. Although an introvert may say, I don’t want to. But rather the job description of the CEO does morph with the scale of the business. And so around that size you could argue with the breaking point, it probably depends on the company, but somewhere in that 50 to 80 zone things change. You start to have departments where there wasn’t, you start to have “real executives”, by which I mean people that have the experience to build out and evolve and improve whole departments. Not just while I was great at Adwords, so I could tell someone else how to be good at Adwords so I’m a manager. That’s not saying we have to have a strategy around brand, around marketing.

How does that evolve over the next several years? How do we go from having 5 people in marketing to 50? Or how do we evolve from having 12 really smart people in engineering who can pretty much just communicate by themselves and get things done, and a hundred people, each of whom have different goals. They’re trying to hit and need to focus on those goals, because it’s so hard that you have to do that. You can’t just be touching everything, it’s too much stuff, you have to focus in and be better at it. You need specialists. How does that evolve? How do you organize those different things? How do they communicate? It’s just, it goes on and on. And that’s just a fragment of what it means to be a leader of an executive over a department.

So for example, those folks which would be harmful early on because they need people to work with or become required to not have chaos. And there’s companies that have tried to get away with not having that, and they’ve all failed. Hypocrisy, but it failed. The Blue Teal Organization, that failed. Medium tried it, it failed. You know, actually it has tended to fail. So I’m not saying that the typical bureaucracy is good either. And I do like the idea of innovating in the field of how many humans can work together to a common goal is a great idea. But fundamentally, this seems like it’s pretty important so far anyway.

So hiring and managing that team, each of which is obviously much more expert and experienced than you are in that area. How do you even interview for that then? How do you hold them to account so forth? How do you push the right amount and not too much?

Jason: In our case, we also had a board of directors because we did take funding after two years. We were bootstrapped for a while, but then we decided to change course and take money. So we had a board, and as the company again grows, the board generally evolves and gets to be more complex and be doing more things like think about compensation, thinking about auditing. Like there’s just stuff that just gets complicated. So either look at all that and say, I’m not even listing all the bullet points, these are just examples of bullet points that emerge as you start to scale that don’t exist and shouldn’t exist early on. It’d be a distraction. So either look at that kind of stuff and go, gosh, that sounds great. Do you think about organizing board members? No. I want to think about product strategy and technical architecture, and maybe even talk to customers. Even if you’re introverted, you may still enjoy at times in the right context, talking to a customer.

And so for me, those things are not an area of interest or expertise. So then I’m exactly the wrong person to do that because I’ll not like it and burn out. Anyway, you’re not doing a good job, the company needs somebody to do a good job at that. So I’m condensing four months of figuring things out and struggling. And there’s other frameworks I could give you to work on exactly how do I know this and how do I design? Who do I hire? What should I be doing if not this? I could share more about how I arrived at the details, but in general that is just a life thing. That should be true of people, and if you’re a manager anywhere like that, that’s great leaders but also what you should want for your folks so that they’re energized and working hard, but loving it. Both. Not working hard because you’re flogging them, but working hard because they love it. Oh, that’s perfect, everyone wins.

What’s the Point of Starting a Business?

Matthew: Definitely. Definitely. I think that’s really important for people to know. Because a lot of people talk about, well, I want to create a successful enterprise and then I want to get out of it as quickly. And it’s, I don’t want to be the fight, so I want to get out of that. You really stayed in your business until you felt that you weren’t the right person to be in that position and then stepped away. But it was a logical process based on what would add value to the company. And I think that’s really important for people to know. And WP Engine, I think the team does an amazing service and everything they do just works so well. And you just have a lot of time now, getting to come and do interviews like this and speaking on stage and things like that, where you still push yourself to do those sorts of things. But you also get to work in a business in a way you want to work in the business. And I think that’s really important as well.

Jason: Well, what is the point of starting a business?

Matthew: It’s to create a lifestyle that you enjoy.

Jason: So if you hate going to work, then you haven’t done that. As long as you hate going to work and you resent it or you don’t like it or drains you. You might as well do that at a place where you can actually get away with a lot less work and get a nice paycheck. Like, what’s the point? So yeah, the point is to build in some sense of that kind a life that’s more designed around you, which again, can be just any number of things. It’s part of the goodness of it. But so you kind of have to where you sort of owe it to yourself. Like if you’re going to do all this nonsense and put all this time and energy into it and take all this risk and everything, how in the hell are you going to do that and then arrive after five years of toil resenting what you do. It happens constantly, by the way. It’s not even crazy, it’s the most common outcome.

Matthew: Because people kind of feel like they owe it to themselves, or they deserve to be in that role. Do you think that’s what keeps people?

Jason: No. I think what happens is you spend all your time, again, just trying to build the company and trying not to die. Just trying to get that next subscriber and the advertiser, and sell the product, sell the service, the hours, whatever it is. You’re just trying to make a dang living. And that takes a long time. Companies take a long time to build, and then the problems change. And so you then have the other problems and you don’t take a step back and say, do I like any of this? And by the way, most of the stuff is pain. And it should be. In other words, let’s say you’re in a band. Bands are cool, right? But being in a band is 95% crap. We’re practicing, we’re lugging, we’re traveling, it’s boring. We’re not getting paid enough. Like 95%, maybe more percent of your time is shit, but it’s worth it for that five minutes. That 5% of the time it’s onstage, that’s absolutely unmatchable by any other experience. So it’s worth it.

So that’s not uncommon in life that it’s 95% work, 5% amazing. So startups are, and that’s okay. But man, a lot of people, you’re in the 95% and you know that. And so by the time you look back after five years, even if you’re successful in the kinds of metrics like revenue or better yet profits that you’re taking home, these kinds of metrics of like, wow, I’ve had a business, it’s a real business. I’m making good money, better than I could make if I had a regular job. I’m in command, which is fun. You know, I have the ego to that, and all these other things you want out of it. So you’ve done it. Which by the way, super rare. Okay. Let’s suppose you got it. But if you’re still in that 95% zone, then that means, I guess, except most of your life is spent doing something you don’t like. What the hell is that?

Matthew: What did you do it for?

Jason: What did you do it for? But it’s also tricky and emotionally difficult to then deal with it. So for example you go, “Okay, I’ll leave. I’ll sell the business, too.”

Matthew: But it’s your baby.

Jason: It’s your baby. Well, I’ll sell it, then I’ll get a big lump of money. Great, perfect. Now you’re not doing all the stuff you hate. You can do anything you want and you have money, super successful. But what’s the most common emotion after someone sells successfully?
Matthew: What am I even doing with my life?
Jason: It’s depression. And there was a study about this that Columbia business school did. And it’s specifically postpartum depression. It’s the kind of depression that women often get after having a kid, directly after having a kid, that sort of depression.

Matthew: That’s horrific. Which would lead to perhaps spending or poor behavior, it can lead to a number of things.

Jason: A number of things, including, well I guess I have to start another one just to get back.

Matthew: Back to doing the 95% slog, alone time instead of just stepping into a role that you do enjoy.

Jason: See, this is a bad situation. Even when you got money in the bank and all this other good stuff. And then that money in the bank scenario, that’s the 1 out of 20, 1 out of 50 scenario. The most likely thing is all the toil and not the good stuff at the end as well. Oh no. So that tells us that we have to be solving for the weeks that we are living now. This is what we have to be solving for. And that doesn’t mean we’re happy every day, every second. Of course that’s not what that means. We should be asking the question, what puts me in that place where I’m deriving energy instead of expending it. And what kind of business might that be and is that still happening. And does that change? Have I changed? Has the business changed, et cetera? So you have to keep asking that question. And you can’t just solve it, that’s not the case. But if you’re not asking it and trying to wind your way to it, then of course by chance you will not hit that right sweet spot. That is not how that works.

Jason’s Introvert’s Edge

Matthew: Look, I think that’s great advice because it’s about making those logical choices, that real evaluation to make sure that you’re happy now and you’re setting yourself up for happiness in the future. I think that’s amazingly important. Jason, you’ve given so much value today, I really do appreciate it. I have to ask you one last question because I ask all my great introverted guests, what do you consider of all the skill sets that you have in your abilities, what do you consider your introvert’s edge?

Jason: I think I would go back to the fact that the obsessed genuinely expert introvert, that’s awkward in these other ways where it has these other characteristics, is successful and can be as endearing, And you can interact with the world in that manner. And because you’re the expert in the area, or because you’re obsessed with the area, you can do great things. Where people who are not as devoted or won’t put in the time or are more interested in what things look like or the relationships, than they are in focusing on this thing. They don’t tend to be the ones that have the incredible physics discovery or the genuinely brand new product thing or whatever. They’re not the ones who do it.

So I think the edge is, in a funny way, the freedom to not need to be out there messing about with other people that’s not obsessing about a thing and not creating a thing. That’s a weakness, you could say. A perspective, it’s a weakness. So the edge is, while you feel terrible if you’re not doing all this stuff, I’m spending all that time and focus and energy doubling down into this, into some area that I’m going to be among the best in the world in. And here’s the worst part, the fact that I’m bad at all that, they love it. It’s endearing. So I get to have this, and they still love me. I don’t need to be able to be good at that. No one cares if I’m good at that or not, actually. Because it’s endearing to be that geek.

Matthew: Just because you’re honest about it.

Jason: Because you’re honest about it and you are good at something, you have worked at something. I mean, presumably you’ve worked at something, right. Something like that. So I didn’t even need to be good at that. At the end of the day, I get the love and the whatever anyway, because they like exactly this kind of geek that does that. So hahaha, I get all of it. That’s the edge.

There’s a reason why you are where you are today, mate. I’ve really enjoyed sharing this time with you, mate. Thank you so much for giving so much value to all the introverted listeners out there today.

And thank you everyone for joining us for another episode of The Introvert’s Edge. Again, if you’ve enjoyed this episode please subscribe, post a review, share it with your introverted buddies on social media so that they too can start benefiting from this value. So they can start becoming more successful as introverts in their business and in their lives. Thank you again for joining us, and I look forward to seeing you in the next one.