Podcast / Scale / Episode 20

The Art of Building Startups with WordPress VIP’s CTO, Brian Alvey

Headshot of Brian Alvey CTO of WordPress VIP , guest on episode 20 of scale

Pull up a chair and join us as we navigate the thrilling world of digital and online media with none other than Brian Alvey, the CTO of WordPress VIP. We take an extraordinary trek through Brian’s illustrious career, unpacking his groundbreaking work with heavyweights such as TMZ, Business Week, and TV Guide. You’ll get an insider’s look at WordPress VIP, understanding its design for large, high-traffic businesses, and how it provides an unsurpassed platform for companies reaching millions of customers.

About Brian Alvey

Brian Alvey is the Chief Technology Officer of WordPress VIP, the enterprise platform for larger businesses with high traffic and high volumes of content. He is an experienced figure in the digital and online media industry, with a career spanning over 25 years. Brian has worked with notable media brands such as TMZ, Business Week, and TV Guide, among others. He also built the first TV Guide website and contributed to the construction of Business Week’s initial online presence. 

As the CTO of WordPress VIP, Brian plays a pivotal role in scaling and managing the platform that powers some of the largest brands globally. His expertise lies in understanding the unique needs of large, high-traffic businesses and providing them with a robust platform that caters to their expansive customer base. 

Aside from his work with WordPress VIP, Brian has extensive experience building start-ups and media brands. His insights on growth, setting clear goals, the concept of iteration, and the importance of feedback have made him a valued figure in the industry. He also offers a deep understanding of lifestyle businesses, the pressures to scale, and the implications of taking on investors. 


0:00:01 – Stewart

Hi there and welcome to Scale. I am your host, Stewart Ritchie. I am the finder and CTO of Powered by Coffee, a web and software development agency working with media brands using open source to solve problems. Scale is a technology about how media is impacted by technology and, in return, how technology impacts media. Today, our guest that I am very excited to have is Brian Alvey, the CTO of WordPress VIP, but with a huge storied background in the history of digital media and online media, kind of almost since the inception. Brian, I am going to shut up and let you tell us a little bit about yourself. Tell us how you got here, your own history, for anyone who doesn’t know you, sure. 

0:00:54 – Brian

That’s very cool. You said storied history, which makes me feel good, right. 

0:00:59 – Stewart

I’ve been lucky. 

0:01:01 – Brian

I’ve been blessed, I mean from a career before the web and then from the web on, which is in 1895 on. I’ve been fortunate to only work with brands you’ve heard of, right. That’s a really good thing. A lot of people work with a lot of companies that nobody’s ever heard of and when you’re at dinner with your family a big reunion or something you have to explain what you do. It’s really easy when you say, oh, I build the software that TMZ and Gadget, netscape and all these different things run on, they’re like, oh, I’ve heard of those things where I built. 

So my career online, the web part, started in 1995 and I got to. I’d been working with Business Week, the magazine, not doing web stuff. They were on AOL but they weren’t on the web and I got to go next door and build the first TV guide website and people are like again, people are like, oh, I’ve heard of TV guide, right, so it’s so very lucky and that was fun. And I went back next door and said, business Week, we need to be on the web and they said, no, we don’t. And then that afternoon I got a call from somebody saying they needed to have a website. I was like okay. So then I built theirs right. 

So Business Week TV guide and then just a bunch of other brands you’ve heard of. So I soon after that, realized you could put a database behind a website. You could build software to power a website. You didn’t have to edit a website by hand. You could build tools for people to do that and then get into building CMSs. 

So I built a couple dozen content management systems over the years. Again, you know NetCAPE and Gadget TMZ all these brands you’ve heard of, very lucky. And then about a year and a half ago, so in 2023, so 2022, the beginning of that year joined yeah, it is, it’s a joint the WordPress company, automatic right. I joined their enterprise division, which is called WordPress VIP. So I’m helping run this platform. That, again, some of the largest brands on earth run on either the White House’s website or NBC and Al Jazeera and all these big, giant, cool media companies next to our all these things. So very big global brands that have a lot of traffic, that are at the biggest media companies or content marketers in the world. So that’s what I do CTO of that. 

0:02:56 – Stewart

Awesome. And then just for anyone who’s kind of like, maybe has like heard of WordPress VIP. Obviously almost everyone listening will have heard of WordPress. But what is WordPress? 

0:03:08 – Brian

VIP, yeah, so. So that’s a very good question. That because WordPress, of course, is the most popular content management system ever turns 20 this year, or just turned 20. So that’s an incredible feat, right, having built a couple dozen like dedicated CMSs for very specific brands, very specific businesses, very specific audiences, platforms, things like that, it’s very hard to build something that works for everyone, and WordPress did a very good job of that because of the plug in architecture, because it was open source, so they really built something that 43% of the web runs on. That’s half the web. They could probably power the other half, so that’s amazing. But but that’s that’s something for everybody. 

And I like to I like to say that sort of the rest of the company. We’re in the enterprise part. So for bigger companies, bigger brands, high traffic, high volume, high volume of content, big editorial teams right, these are the kinds of things we work with. The rest of them build all the other stuff. So the WordPress that you download and you could build a six page dentist website on, well, that’s that, that’s what WordPress does. That’s great. Well, we do the the part of it. That’s really for the biggest businesses. So, if you have a very large amount of content if you have, or it’s a very important website. Actually, I love the name of your podcast scale because, I. 

The way I explain VIP to people is you build it, so you build your WordPress website. You build it, we scale it, so you bring us your craziest WordPress thing, that’s, that’s got the most tables or the most multi sites or the most something, and you’re having trouble scaling it yourself on Amazon or at some other company that has millions of customers. We have roughly 1000 customers, but they’re all giant brands. You’ve heard of doing really hard, really important things, so that that’s what WordPress VIP is. We are here to solve the enterprise things and to show you that WordPress actually can scale at the level of these giant companies that I mentioned. 

0:04:56 – Stewart


So one of the things we kind of come up against is like oh, wordpress can’t scale, wordpress can’t scale this and can’t scale that, and I’m like that some of the very biggest sites in the world are running, are running WordPress, and it’s a bit of a like message of people you’d be like X, y and Z media round has like 20 brands and 20 sites within those brands and they’re all running on probably one huge multi site instance and they’re doing more traffic in a day than your app that you’re worried about scaling has done in its entire existence. 

But anyway, we’re not here to talk about WordPress or particularly repressed VIP your own background. Haven’t been worked with so many media brands. Over time you have been through a lot and we have seen and one of the things we talked about before was how do you media brands start to grow and how do they iterate, and one of the things you brought up that I thought was really interesting was approaching them more like startups, like having a quick iteration cycle as they’re small, like just doing something and seeing what sticks. So I would love to like dive in, dive into that a bit more. 

0:06:00 – Brian

Now. So it’s funny because on podcasts you there, they’re always like a trip back in time. So so when I could talk about, like today, the thing, things as they are, where things are kind of at scale. But how do you get to scale? Yeah, and it always, it always starts with from nothing, right from zero to one before you get to 60, right, like you have. You have a long way to go. 

And when I was building startup, creating companies, I just I didn’t know a lot of the terms. I didn’t know what an entrepreneur was. I didn’t know that we were making a startup. I knew we were creating a company, I knew we were creating a business, but I didn’t know those terms, I didn’t know the rules. I was very, again, very lucky to have famous investors without really knowing what valuations were and what. All the stuff that the world has learned from the social network movie or from Shark Tank or from any of these things that kind of explain our. 

The sport that I’m in Startups is my sport, right, yeah, and and all throughout a lot of that it’s been media related, so publishing, so and so and so back to the how I got into the web. I was working with media brands, right, and TV guy, business week, things like that. We were, I was in one building next to another building and time life was the one after that. So all these brands were on the same stretch of blocks in New York City and people would just jump jobs between all of them, right? And so I had publishing in my blood. I had, you know, print publishing, magazine art I was a magazine art director for a while. I did a lot of desktop support, so so I’ve always approached things as In publishing and in media companies. 

Anyway, when you start one of those, you are very much like a startup. You you are, you know, struggling to get from zero to one. You’re struggling to get your first customer, then your 10th customer, they’re on your way to a thousandth or millions of customers, and so that the rules are all the same, that they are. If you’re trying to launch An app like uber or Yelp or something like that, or a magazine or a small, you know, some kind of brand, the local news brand, so it’s, it’s all the same rules, and you are Actually, tell you, an interesting thing. So so I co-created this website and gadget. 

It’s like a long time ago now 20, 20, almost 20 years ago and the first thing started. It was Peter Rojas. He was a journalist and he had created a site called gizmodo, so he actually basically invented gadget blogging, which was a very big thing for a long time. And you look at what those brands are now gizmodo and in gadget and they’re still around 20 years later and Like they’re, they’re, they’re huge and they have large teams and they’re very important, right, they make a lot of money, a lot of advertising revenue. But back when Peter was working on gizmodo, he worked. I think he worked on gizmodo for about a year and a half before we stole him away to create and gadget with him and my. My part in that was I built the software that it all ran on. I was always building these. These platforms are oftentimes that you open the names and the land, the designs for a lot of our websites, all these other things, but not that one that he came up with a name and his future wife Came up with a logo and all this up, which they still have the, the, the gadget logo, so so, but but they started. 

We started with nothing right, and it literally gizmodo was a one-person team. It was just Peter, so he wrote a bunch of blog posts every day for 18 months and his deal wasn’t very good. He didn’t own gizmodo, he was just working on it and he had created something very valuable and he wasn’t gonna get anything for it. So we stole him away. He created in gadget and it was very funny because on day one of in gadget, we didn’t have any traffic. Nobody came to the website like every one of these massive, massive brands was a nobody on day one and had to figure out ways to get attention, figure out ways to grow and and get from zero to something and I, one of them, were interesting. Stats with it took us, it took it so. 

So when Peter left, his old website had a lot of momentum, had a lot of traffic, and even if they never posted again, gizmodo would be a giant brand, like it had a lot of traffic. But then then they they stacked it up with more than one person. So now you have Peter on gadget as a one-person blogger trying to compete with his old blog, all his SEO Stuff that he’d done there, all that momentum, and now they have a two or three person team. So now he’s starting from from zero. We didn’t have any money. Right, we couldn’t have fun this thing and higher at fall person team, and so he. It took him a year to catch up to his old brands traffic. 

But in that year you’re doing everything you can to figure out ways to get attention, to figure out ways to get ahead, and so I think the only way that you survive those things and and keep your sanity is to set goals. In a year I would like to be this big. What are the steps that it will take to get there? Great, and if you beat those goals, we usually make new goals, right. If you then sell the thing for a lot of money, you still have to figure out ways to motivate yourself and get to the next level. But the rules for growing a media brand, the rules for growing a startup, any kind of business, are basically the same. It’s how do you get from zero to one and then, once you do get to to there, how do you keep motivating yourself to go to two, to five, to sixty? 

0:10:49 – Stewart

Absolutely so. Then it sounds very much like to kind of come back to like the start of thing. There’s two words I feel like they’re thrown around a lot, kind of like the minimum viable product, like what is your minimum viable? Media brand and Spoiler. That’s not really a technology problem. That feels like that’s a content problem of like I’m making the right things to talk to the right audience and finding the right schedules for that. But then also the other one is more your product market fit of like product. Is the content? Is that fitting with what people are trying to get to? Is that kind of when you’re kind of coming to this for yeah, no that. 

0:11:24 – Brian

So those rule definitely apply. And and thinking back again, as you get to do on a podcast and looking back at yours we’re looking back in time, right Time travel thing we’re doing right now. Yeah, product market fit is interesting because it’s it’s so poorly defined or it’s so impossible to define and what people basically say is You’ll know it when you feel it right. And the feeling of product market fit is Is that you’re no longer having to go and push your thing onto people put you’re, no longer You’ll ring their doorbell, try to get their attention, like they’re coming to you. And it’s funny because in, if you don’t, if you don’t, if your business doesn’t sell something at some point, then it’s just a hobby, it’s not actually a business, right? So at some point you have to sell. 

And in the media business, you need to sell advertising, you to sell sponsorship events, whatever it is you’re doing, and the way that the best kind of sales is order taking. It’s where people are running towards you and throwing money at you and you’re just writing down great, I’ll slot you in for this many ads for this quarter or whatever. The hard part is when nobody cares about you and you’re trying to Beg them just to okay, I’ll discount it. Okay, please, please, I’ll give you pay for one month. I’ll give you three. Right, that’s a bad position to be in, but that’s where everybody starts, right, you’re a nobody and nobody cares about you, until you’re somebody and everybody’s throwing money at you. So. 

So we went through that with engadget. I remember how, at some point, it got to a point where it felt like, oh, we were doing more, more order taking, and the world was like for two years the world was like, oh, we don’t care about blogs. And all of a sudden, aol was like we really care about blogs, can we buy your company? And then advertisers were like we need to take Ford. The car company was like we have ten million dollars it’s been an advertising, but we want to put two of it on blogs. I’m like, okay. And so things got easier when you, when you got to certain point but getting there is a lot of work. 

0:13:08 – Stewart

Absolutely. I wonder how much then, hindsight in these things plays in. Kazenki said I forgotten the Genstein that started Gizmodo, so he was there for about 18 months. 

0:13:19 – Brian

Yeah, peter Rojas. He was a great. He’s still a super smart guy. Now he’s an investor. He’s a super smart journalist. 

0:13:25 – Stewart

Well, he was definitely a head of the trend on that one very much. So I mean, like when Peter Rojas was starting Gizmodo, it took him 18 months, two years, to kind of get it to the point where he’s pulling him over, and he managed to take that knowledge that he had applied and built it up so that in gadget could walk where Gizmodo had run and kind of caught up within a year to the SEO thing. So there’s a certain amount of them like I’m learning this. I’m learning this. It’s never just like I’m done. I’ve picked up information here that is going to like help me get to that snowball, to like build out that next, that next piece. 

0:14:00 – Brian

Yeah, there’s definitely a learning thing. And, well, it’s a funny thing too, because we built that company and then we sold it in like two years. It was really quick. We only had one investor, mark Cuban. So back to Shark Tank. Right, it was way before Shark Tank, but we were small and then we didn’t acquire it. It was cool. So the? 

But right after we did that, I had famous web design friends who were like, oh, I’m going to make a blog network now, because that was what I did to make a bunch of money, and so they wanted to do the same thing. But but even two, three, four years later, all the rules about SEO, all the rules about having a network of sites all linking to each other, and all the the cool things that we happened to do we were there before AdSense existed, google AdSense and and by the time, two years later, we were actually. So when Google went public, they had to do their S1 filing, where they explained to the world hey, we’re a search engine company, we’re really small right now, but we think we’re building something big and we don’t make any money, but we do have this cute little thing called AdSense and we think it’s going to be big, right. Of course it’s a joke. Looking back, it’s gigantic. It’ll hold the whole world. The whole world runs on it how the web makes money. But at the time they only had sort of two examples of people using AdSense that were worth anything, and I forget the other one. But one was me and Jason. It was our blog company, right, and so we were in Google’s S1 filing and it said, yeah, these two, these two dopes from Brooklyn, I have built this network of websites and they put our code on their websites and we show ads and they’re actually on track in in in one year to make a million dollars on, to make a million dollars a year on AdSense, and then they can afford to pay their employees and take salaries themselves. So they’re building a business based on this cool software we have. So we were fortunate to be part of that. But but all those rules for what we did in those two years, two years later, they didn’t matter. 

A lot of the people who worked with us on that blog company went off to start new things. They tried to start Engage at 2.0, or they tried to start AutoBlog 2.0 or whatever the next thing was, or I had friends that would just be sitting with me and straight faced over dinner they would say I’m building up a blog network but it’s all about pets. They’ll be cat blogs and dog blogs and all this other stuff. And I’m just looking at them like this is a horrible idea, it’s going to go nowhere. It’s what worked for me. Is it going to work for you? There’s a book of what got you here, won’t get you there, and in just two or three years all the rules change. 

So you think of that transition of creating Gizmodo and then creating Engage it. We were lucky that it happened in sort of like a one year or two year window, but you wait five years and all the rules have changed. So everything you’ve learned goes out the window. You’re constantly learning and I like to think that that everybody’s a beginner at some point. So all these companies we’re talking about who are starting a media brand, starting from zero, starting from being small One, they have a year or two where they get to be completely unfamous. Nobody knows them, so they can change a lot. I mean, there are a lot of stories that the original TMZ was not the TMZ that it is today. They got to do a lot of stuff before they were famous and change a lot and iterate to get to the thing that finally did get product market fit, that did resonate with the whole planet, that did break news that they were the number one site on earth that day. 

But and I also think about, at one point we were taking publishing tools to brands. A few years ago and six or eight years ago all brands wanted to be publishers, right? So if you’re Pepsi, you’re not a soda company, you’re a publisher. Because Red Bull, the publisher, they’re a media. Everybody’s a media company, right? Ibm, mcdonald’s, the raw media companies, right? Harvard is a media company, sure, right. Whatever I mean, they do have a book, but everybody’s doing that. And if you, and if you’re doing that, you could be a hundred year old company like IBM and you’re a, you’re a zero year old publisher, you’re a zero year old media company. So everybody’s a beginner at some point. Some people get to do it with a lot of money in the bank and tens of thousands of employees, and some people do it with nobody, sitting around at home on a laptop and start from zero. So it’s a back to the startup thing, startup rules. 

0:17:52 – Stewart

Applied it all Absolutely. So let me, let’s look at that then. So if you were, if you were starting today you media brand, or you’re already a small media brand, so you’ve got like some level of traction. You’re getting that buys and pays you some months. I, what would? How do you think those people move the needle? Today, in a world where we’re looking more and more increasing distrust of what people are reading online, the social platforms that were used to build the kind of intermediary Media brands for your buzz feeds and your vices and things like that those networks kind of slowly shutting down what’s? What are good things you think for aspiring brand owners to be looking at today to try and start getting that little bit of traction? What do you think? 

0:18:41 – Brian

So that’s a very broad question, I’m afraid no, no it is, but it’s a fair one, right, like the what, what, the, what the market looked like when Buzzfeed launched 10 years ago, or whatever it was, is completely different than it is today. Right, and sometimes you have a window to do a certain, a certain kind of thing. You have a 3, 4, 5 year window and then pass that and it nobody may care about the thing that you’re doing. Right, that that you and the plan that you start with. They talk about this too, that, no, no business plan survives. First, contact with customer right. 

Yeah, everybody’s a plane, right, you go, you go and you, you meet a customer and then it all changes. So so you can have plans those don’t matter. I actually tell you, thinking before about talking with these brands. 

You talk about MVP you asked me about that before and answer so MVP is an interesting concept just because it means minimum viable product, get something out the door. And I can tell you that if you launch something, if you actually get something out the door and get an audience and get feedback from them, you’ve now beat 99% of the people who sit around saying I have the perfect idea for a brand. If you have the best name, it’s gonna look like this and it’s got this very retro feel, it’s very edgy and the content is like and you do, you have this thing in your brain that you’re describing. There’s a really good book by Rick Rubin who produces they would produce like the Beastie Boys albums, and he’s worked with a bunch of different like rap stars, metal stars, just, and and it’s all about creativity and he talks a lot about just get the thing out the door. Take, take the thing in the moment. Don’t spend 10 years working on your album, spend one, spend six months, just get it out the door. And he makes a really good case that when you’re being creative One, you have to. If you don’t get this thing you’re working on out, then you don’t have room for the universe to give you that next thing right, like, until you have this baby, you can’t make another baby. It literally is like you can’t do it. So get the thing out the door. 

So I look at this this sort of MVP thing and I think, if you ship something at all, you’re now better than 99% of the people who sit around a coffee shop talking about the amazing idea they have and they’re never gonna ship it. So that’s step one. Yeah, then once you get it out there, you have to iterate, you have to get the feedback, you have to make it better and grow. But it’s it’s again like all the rules go back to start up, rules like growing a business and learning. So then you think of okay, how would I build it? You asked the out of it build a media brand. So how would I build a blog network today? Well, first off, you wouldn’t build a blog network. 

Some people think, oh, the new version of that is a whole bunch of Twitter accounts or the Gary Vaynerchuk’s company gallery media. They have a bunch of Instagram sites, right, so they kind of have a modern magazine network, the same way that Condé Nast or Hearst or Penske, which owns Rolling Stone and all these other things and runs on WordPress VIP, all these great titles, variety and stuff those Magazine, those magazine companies with 30, 40 brands, or what we built, what we based our blog company on. We’ll have a brand on that will have one site that talks about cars, one that talks about gadgets, one that talks about parenting and babies and stuff one on luxury things. So all of those things. Today, if you’re, if you’re, gallery media, you think, oh, I just have to go to Instagram and get like Instagram comm slash drinks, instagram car comm slash cars and they have all those things. So they basically have this really interesting magazine network that has no magazines and has a very small team doing things and they run an interesting business. 

So is that where what you do? Or if You’re building on someone else’s platform, is that a terrible idea, right? The good thing about building on someone else’s platform itching yourself to Facebook or to Twitter when it was young or whatever a tick-tock is you get a lot of exposure. Right, you do, you get a lot of exposure. But the bad thing is they can change the rules and everything goes away. So I think there’s a case for Building something on your own, but the rules for how you get attention today are not the same as they were three years ago. It’s certainly not what they were 20 years ago. It’s just, you just have to be really, really good at today’s rules. I and that’s that’s a skill A constantly adapting. How do you get something going for 20 years like WordPress, or 20 years like in gadget is pretty magical, because a lot of these things don’t survive you talk about vice and Buzzfeed and all their challenges. 

They’re only 10, 10 years old or whatever they are, and they’re, they’re struggling. 

0:22:47 – Stewart

Cool, absolutely. But I think then the next I suppose jump on from that is the not being afraid to change what you’re doing and not being afraid to iterate. Just because you have gone down A route does not mean that you are then precluded from another route. Thinking kind of more recently around to say business model ways, like time had no paywall for a long time, then there was a paywall and it’s had a paywall for 10 years or so and now that paywall has come back down as they try to give more exposure to the content or whatever, give more space for ads, I feel like that’s an important thing to you. Like people get stuck in, like this is how we monetize and this is the model, rather than the ability to change and move and Migrate, so not getting tied to the platform either, like YouTube, right, so that makes sense? 

0:23:35 – Brian

Yeah, it does make sense. So why do you think people are resistant to change? Why do you think if, if I don’t have a paywall and I add one, 10 years later I’ve got a paywall and now I’m thinking, gosh, I want to take the paywall away what do you think is the thing that stops people from doing that at time that are working on this? 

0:23:54 – Stewart

I think that there are a lot of people with entrenched interests that I mean I don’t know what 10 year of someone at time is to be like, who decided that goes up. So they don’t want to like admit that they were wrong, necessarily at the time. But you know, I don’t know. I think they could be like right. Well, actually we tried this, let’s try something else and see if it sticks. Like. I’m not saying it’s bad, they took a time. I think it’s like interesting. One of our customers, right. So like. 

0:24:21 – Brian

Mark Benioff, who’s created Salesforce, is one of my parent company’s biggest investors and we power and sale. The Salesforce website runs on our platform but also time. He went and bought time personally because he has a lot of money and he cares about the brand. So he bought them and I’ve only been here a year and a half and in that time time time time they went from one CEO to another, so there’s not a lot of sort of tenure for the employees that are there, right? So that does factor into it. Right, somebody comes in. They’ve only been there a year or two and everybody who comes in wants to flip the switches. Right, we have a decentralized sales team. Wait, that’s a terrible idea. Let’s centralize it all. And they just flip switches. The next person comes in and decentralizes that. That must be the problem. 

But anyway, when you’re doing that, the hesitation for something like that is the sort of fear of embarrassment. We made a promise to the world that our content is so important that it’s worth paying for, and now we have to go out and tell the world hey, we changed our mind and people get into this. They just get stuck in fear, right, and they’re worried about what people are going to think what people are going to say that promise that they made and they’re going back on it. And the dumb thing is people don’t remember any of this. Who cares? Like, how much brain power or time do I have in my life to think about what Time magazine did or didn’t do for a payroll? Like nobody cares. Media journalists care. But my God, if you work in media, don’t read media journalists, because it’s just a very, it’s a little echo chamber. It’s going to drive you nuts. 

So you can make lots of changes. When, if you’re a mediumcom and you’re on your seventh or eighth business model, okay, people remember that you, you’re like a roller coaster, you keep changing things. Maybe it feels like you don’t know what you’re doing, but if you’re, if you’re time, like you still have the room to experiment, and if you can defend why you’re making a change, then you’re good. But people are going to remember two weeks later, two years later, like, just do it. Also, people will hesitate because they think, well, I can’t try this other thing because I just don’t have enough people or enough resources or enough ways. Whatever, if it’s important, try it. You don’t have to back to the minimum viable product, right. You don’t have to do a $2 million project to do that, do a two week project to do that or two months project to do that. Any, any good business should be built to be making experiments all the time. And if you’re built to make experiments all the time, to go ship. 

And we have a phrase or a phrase I learned from my parsley team. So parsley is the company analytics company they’re about a third of my product team is parsley and the other two thirds runs that WordPress platform, the enterprise WordPress platform. They have a phrase ship to learn. So like we can work on something for two years, it doesn’t matter, but if we don’t get it out the door and get feedback on it, we really haven’t done anything. So you don’t, you don’t go learn things so you can ship. You ship to learn, get it in front of products, get the in front of your product in front of customers, get feedback on it. Ship to learn. And a lot of people just just get in their own heads about this perfect thing they have or they’ve got to wait too long. And I’m I say this because I’ve been guilty of this for years and years and years and decades Right Like I’m that person who will overplan, sketch, think, worry, whatever. But the times I’ve been successful, at the times like this, got something out the door. Yeah. 

0:27:25 – Stewart

Don is the? Was it good as the enemy of Don, or something? Yeah, oh yeah, exactly. 

0:27:31 – Brian

Perfect is the enemy of something good. Yeah, anyway, we’ll look it up. 

0:27:36 – Stewart

We’ll find it, we’ll put it into notes. But that’s so interesting because then that comes back to kind of the core, like fundamentals of kind of startup culture and how startups approach this kind of work. A certain amount of agility here of like cool, have an idea, build a thing, ship it. Did that work, did that not work it, or it and in some cases doesn’t have to be technology, that can be like here’s an idea for a piece of content. If we make a really big, long piece, doing some expose, a kind of stuff, like like dabble in some investigative journalism, when traditionally you’ve been more of like off, set blocks, I like is that going to resonate with your audience? But the only way to find out is to kind of do it, see how that worked out and then decide again to try. And if you want to try that on, is that kind of where, where you’re coming out with this? 

0:28:22 – Brian

So, so, so no, it wasn’t exactly what I was thinking, but you’re sure you’re answered that you’re in. You’re answered better than mine, which is, if you just think about the content part, right, you’re creating content, you’re, you’re putting that out there. So forget about the business, forget about the brand, Forget about the logo and the colors and all this stuff. People, people do that. I’m a very slow blogger. It takes me a long time to come up with a headline, like I stress and obsess about all these things and what I write, and the company I’m at has a big writing culture. We we actually don’t use email. We have an internal blogging platform, and so you, instead of having things in email where, if I leave this company 10 years later, you can’t find the things that I wrote, right, they’re kind of gone we do these things on a blogging platform so you can search anything. So when I joined, I actually got to go use their search for their internal blogging platform and see all the times that I was mentioned or companies or products that I built were mentioned. So it was a really weird thing Finding all these times when very specific people said a whole lot of stuff about me. Oh, Brian’s changing his business. We should swoop in and steal his customers, like all these really interesting things that a business would say, and they are able to go back in time and see that. So the big writing culture and I’m a terrible writer, but I’m a person who builds platforms for writers and as someone like that, you can also get in your own head that like, okay, so I’m going to write the best thing, but first I have to build the right CMS, because it’s the authoring interface, and then, wait, wait, there’s a new database that came out. Oh, there’s this new way to use JavaScript and there’s this thing that you can do. Ah, this framework is not that good. I’m going to pick another framework. And now you’ve just spent months trying to build the software so that you can then write the story Instead of just writing the story. 

Make a notepad, write it on paper, go to Google Docs whatever word I don’t care Like just go write, and people will spend a lot of time not doing that. I am a terrible writer. I obsess over those things. I can’t just write. It doesn’t come easily to me. So it’s funny that I work in media and publishing, but I’m usually building tools to help people get 20 stories a day out, or 200 stories or 2000 stories a day out. And that’s a good place for me, because if I had to actually write any of those stories, you’d get one a month from me, which is terrible. I’d be starving if I had to write for a living. But it’s the same deal. You just get it. You have to get it out the door, get it to people. And then here’s the funny thing If you do something dumb or you say like I’m going to be reviewing horror movies and then later on you change and you say, okay, I’m no longer doing that, I’m reviewing all kinds of movies because I want to have a bigger business, your early audience is always going to say why did you abandon horror movies? 

That’s the only reason I like you. Yes, but I have an audience of three people. I want an audience of 3 million or 300 million people. So you worry about what that original core audience and not realizing it’s. You’re still at zero. You haven’t left zero yet. You can experiment for years and years and years to get to something good and people get hung up on those first hundred subscribers or whatever. Like hundred subscribers is nothing. Thousand subscribers is nothing. A million subscribers on YouTube is nothing you can change. You can branch out, you can do something new. In fact, if you don’t, you’re going to fail Absolutely. 

0:31:20 – Stewart

You have to keep changing and iterating to get where you want to be. But I think that also like to me that’s an interesting question of like the scale of these works, like what is kind of, what is the ideal scale of these things? Because I feel like I’m personally more attracted to like niche publications and I’m like, oh, they cover this one thing like really well. So your horror movie example of like, yeah, cool, I want to like know what these people like work at and like what they think and I resonate perhaps more with their view. 

And there’ll be another like, say, a video game site where I’m like, yeah, I resonate with, like this small group of people, but obviously those aren’t like huge businesses but they get enough traffic to do what they want to do, whereas you then have these groups that go broader and broader and broader, to the point where they lose their voice and they lose as much of the reason anyone was paying attention to them other than they have a brand that represents, and I don’t know where the right slot in that is, and obviously they’ll vary per person and per company. But are we letting? Are these brands getting too big? Like there are so too many moving parts, too much overhead between the product, the content and the readers, or I don’t know where I’m going with that, it’s just interesting. 

0:32:37 – Brian

No, I get your question. So your question is actually about scale, right? So great name for a podcast, right, so it’s about scale and there’s a very, there’s a derogatory term in startups in Silicon Valley right. 

My sport, which is a lifestyle business. So you, there are two kinds of businesses you can have. You can have one. And so when, when Jason and I set out to make that blog network back in 2003, we were we were not thinking of it as like a lottery ticket, we’re going to buy mansions or whatever like this thing we were thinking of we literally sat down at a New York Knicks basketball game and we talked about 20 different ideas we could do. And then we thought about this one. We said it sounds a little bit like about dot com. Back back then it was called the mining company or maybe they were already about to come. They just been bought by the New York Times for like four hundred million dollars. 

And we were like, oh, what if we could build a network of websites, each run by, which is now like what Reddit has or now what all of these other things have? But back in the day it was, there’ll be one one on dogs, there’ll be one on one topic on the HTML, that we one topic on cars, whatever it is. And so he and I sat there and calculated what would it take for the two of us to be able to make? I don’t know. Two hundred thousand dollars a year, like that would be rich. If we could make two hundred thousand dollars a year, we’d be fantastic. So what would it take to put together? And we thought it would be like 200 sites and it turned out the answer was like 35. 

0:33:55 – Stewart

It’s trying to find. That line comes down to that lifestyle business problem of like oh, do you want to have a as a publisher? Like, have a small focus, lifestyle business effectively where you know your audience is dedicated. They like the resume really strongly with you and your like small editorial teams point of view versus the huge brands out there that seem to struggle and seem to feel a lot more frequently because it goes back to the investor thing. 

0:34:25 – Brian

Yeah, so. So when we were doing that, we were actually planning out a lifestyle business, right? If we had talked to investors, they would have said, oh, this is cute, but I’m not interested because this is a good lifestyle business. The two founders will make some money and your people will be happy. You’ll be blogging, you’ll be writing my horror movies or whatever the thing is we’re talking about, right, but it’s never going to be big. It’s not worth it to me because investors have investors themselves, limited partners, who put in a bunch of money, so much wealthier companies or much wealthier people or wealthier companies who give them money to go invest in they have to. So they don’t think you’re going 100 X or 1000 X your business that they don’t care. If you’re going to 3 X, that may be great for you as a founder to make a couple million bucks or tens of millions of dollars, but it doesn’t move the needle for them on that. So you’re a lifestyle business. So that’s the derogatory term, and we set out to make a lifestyle business and I would say we succeeded in that. We may do one a little bit further than that, but we didn’t make something that big investors would have been thrilled with. And that’s when you talk about Buzzfeed and Vice and all these companies. They are. They could have been something interesting, but when you take on all that funding, you know the one company that’s done it the best is Vox. So Jim Bankoff with Vox and Polygon and Espionation and the Verge and all those things he worked today. Well, we were there. He was actually one of the people who bought our company and he looked at our model and he said, oh, this is really cool. You can launch new sites on new topics in a weekend. Put a small team together and go conquer and and and and steal, add money away from bigger companies. This is great, let’s do that. And he went off and did it, but he did it in such a big way and he raised a lot of money, but he’s been able to navigate that and keep going and have a sustainable business. It’s really hard. 

So if you look at the two kinds of businesses the lifestyle ones that never and it really does come down to do, you take outside funding. Because once you take outside funding, you’ve made a commitment to the people who gave you the money that you’re going to give them back 10 times that money, or double, or something that at some point you’re going to sell your business. So lifestyle businesses are ones where you don’t sell them. You’ll work on a thing for 40 years and and it’s it’s feels like a hobby, but maybe it makes money, maybe it’s fun, some events you do or something, but the once you take investor money, whether you’re a startup or a media company you’ve now agreed that at some point you’re going to sell your business, no matter how much you love it, no matter how much you don’t have another idea in you, and you’re going to regret selling your business because the only, only good idea you ever had is the only space you care about. Right, if you sell your horror movie website, you really love horror movies. You still want to write about horror movies. Now you want to start a second horror movie website and compete with the one you made. That’s, that’s a terrible way to live. 

So, those businesses that are the lifestyle ones versus the ones that have this pressure to scale in the scaling group, you only hear about the successes, really, when you hear about the failures too. But you, the reason you think that that’s a good way to go is because, oh, so-and-so built this thing and then they sold it and they got a mansion or they got a boat or whatever. I don’t know how they got to put their kids through college. That’s neat, but that’s not the norm. That’s like one, two, three percent if you’re lucky. So you look at the buzz feeds and the vices and all these. There’s a bunch of other ones all from that era that are struggling. They took on a lot of money. They have a lot of pressure. They were really good at doing a thing for that year or that, that window of three to five years, but now it’s 10, 15, 20 years later and there’s a lot of pressure on them and Investors don’t. Investors don’t like something that goes on for that long. They’re each of their funds has a 10-year window after 10 years. Like. 

I had a conversation with a investor one time where we were the last thing, last thing. They invested in their first fund and it had been a bunch of years and they and they sat in there, it sat me down. They’re like look, a couple of the companies from that fund have gotten really big and exited and give us our money, made us a lot of money. All the rest of those companies, except you, had the decency to go out of business. I was like what you’re upset that I’m like making money. No, I had a lifestyle business. We were making a couple million bucks a year with a big team. We were growing but we weren’t doing what they wanted and they either want you to get really big quickly or just shut it down so they don’t have to think about you anymore, like yeah, that’s very hurtful to tell you yeah that I hate your business that I’ve invested in. 

I’d like you to shut it down because it bugs me to have to think about you. Yeah, that’s it. Like I like my business, I’m making money. 

I’m having funds, yeah so there’s a really there’s a big wall, and that wall is Did I take investment money or not? And that dictates how you’re going to do, and it’s very hard to scale something and be that 1% of the ones that are Scaling and exit and make the investors happy, and then, once you do, you sold your favorite thing you ever built and now you’re miserable. So that’s, that’s a terrible thing. So, anyway, it’s good to have a lifestyle business. It’s great if you can do that, right. But everybody who does that is like they want to go to the next level. Now I want to get a TV show. Now. I want to get on to such and such. Now I want to serious XM show. You always have that. Now I want to publish a book about horror movies right, you always have that next thing you want to do. As long as it fits in, that’s great. But some of those things that you you kind of a you know rush to go do aren’t healthy for you. 

0:39:19 – Stewart

Absolutely. First off, let’s go to that investor said that he I’d be very upset. Someone said that to me, so I’m sorry I was. 

0:39:26 – Brian

I was really upset in a moment two weeks later I was like I’m the biggest investor in this business. He doesn’t like this. There must be a reason and we ended up pivoting and doing something really cool. But it was very hurtful that day and it kind of broke my brain like, yeah, he was really upset that we were making whatever six million bucks a year and on a small team, but we weren’t doing what he wanted us to do. That’s funny. 

0:39:46 – Stewart

He’s just for those kind of like groups that are interested in kind of like getting up and getting started. To recap, I suppose, is that kind of a purchase, kind of Is the startup model? Get something launched rather than sitting on it forever and ever. And you’re already ahead of 95. 90% of people are there. Try things, see what sticks, try different kinds of content, try different kinds of business models, learn to kill your darlings. Just because you had a paywall doesn’t mean you need to have it going forward, and just because you didn’t have a paywall doesn’t mean there shouldn’t be one in the future. Seems like donation or any other model. And finally, be kind of clear on what it is you want as you go you do. You want to have a lifestyle business that’s fun and interesting and engaging for you personally, or is it something that you want to scale and take, take on to to everything else and grow beyond your kind of small teams? Is that about kind of it’s a great list. 

0:40:40 – Brian

If you list it out in bullet points and you hand it to somebody who’s sitting in a coffee shop Thinking about the thing that they want to build, they will read that list and go, yeah, that’s a good list, that makes sense. And they will still not ever ship anything Because once you ship it, it’s no longer the perfect thing in your head. That Rick Ruben book. He talks about the demo that you make for a song versus the actual song you make and he says demos are. They’re actually really bad for you Because when you listen to it you’re like it’s got to be like this and your drummer is not doing it Right and the bass part doesn’t sound right and I have this, this, I have this thing in my head for the strings and like nobody can quite get that. That’s that version, that’s in your head, the perfect demo version in your head. 

Out into the real world it’s very hard to do and one of the ways to do it Like hide the demo, don’t listen to it again. Just go. Just go make the thing you’re gonna make. So you can give that list you just made to somebody in a coffee shop and they’ll nod their head and they still won’t ship and they’ll never learn and they’ll stay at zero. It’s, it’s a. It’s a hard thing. 

There’s a something I was just reading about. It’s like the five second rule, where you like you, you just like when you have to do something really hard that you don’t want to do, you just like Countdown from like five, four, three and like going off a diving board, and you just do it. You just take the steps and go, and so this five second rule things really interesting. You don’t need to read the book Because it’s literally in the title. It’s the five second rule. But you, you just get, you just got to do it, you’ve got to start and you can hand that list you just made to somebody in the coffee shop and they will still sit there and a month later they haven’t shipped and that’s the 99%. 

0:42:07 – Stewart

There’s a really interesting like quarrel, a lot with podcasts where, like, everyone has an idea for a podcast. 

0:42:13 – Brian

If you get the first one out, you’re already like ahead of yes, 50% of people have ever had a waiting on the perfect theme song or the right software. 

0:42:21 – Stewart

Right like again, you can wait a long time to start and if you, if you get to like three episodes, you have shipped more Episodes than 95% of the podcast listed in the iTunes directory. If you make it to 10, you’re in like the top 99.5, something weird. Like that’s just yeah, I’m building that momentum, but awesome. 

0:42:42 – Brian

And then and you’re still at zero you’re still a nobody, and you can still do everything. I’m an experiment. 

0:42:47 – Stewart

You’re trying, you’re absolutely trying. Every so, Brian, thank you so much for your time today. I really appreciate it. I know you’ve got lots to do. If somebody wants to find it more about you kind of what you’ve been up to WordPress VIP work where can they go? Where can they look? 

0:43:02 – Brian

Yeah, we’re WordPress VIP. I think it’s WP VIP calm, but Brian alley calm. I blog there twice a year. Yeah, so so, Brian Ali, that this is on Twitter. All the other places but Twitter and LinkedIn, those are probably, but Brian Ali calm. 

0:43:15 – Stewart

Yeah, Brian Ali, calm, awesome. Thank you so much again for your time. Thank you everyone for listening. I hope you’ve enjoyed the episode. If you have, please be sure to. And you’re not already subscribed, please be sure to subscribe. Leave us a review on iTunes, google Play, wherever you get your podcasts, and share it with a friend If you think there’s something here that would be useful for them, and we will speak to you shortly, in a couple of weeks. Thank you very much, you. 

If you have any questions or need help with Word Press VIP, you can contact Brian or the Word Press VIP team using the following methods:

• Website: https://brianalvey.com

• Website: https://wpvip.com

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hosted by Stewart Ritchie

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