We Discuss The Future of Podcasting & WordPress With Matt Medeiros

Matt Medeiros is a well-known and member of the WordPress community and has been producing one of the longest and respected podcasts ( The Matt Report ) about WordPress and online entrepreneurship. Matt about 9 months ago joins Castos as “Director of Podcaster Success.”

We also going to be asking him about his new role and also his thoughts about Podcasting in general. We will be asking him questions connected to his latest Mat Report podcast interviews which has done over the past six months and what does he see as some of the most important themes and patterns that he has observed during these interviews?

Also, what does he really thinks of how the Gutenberg project and how it has been managed by Matt Mullenweg?

Plus also when will WordPress do its IPO.

This Week Show’s Sponsors

Castos: https://castos.com/

Convesio: https://convesio.com/

LaunchFlows: https://launchflows.com/

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Jonathan: Welcome back folks to WP-Tonic show it’s episode 601. We’ve got a great special guest for the show and a friend of the show we’ve got Matt Medeiros joining us, the director of Podcaster Success at Castos. and a well-loved and respected podcaster himself with the Matt Report. I’ve also got my co-host, Steven. Steven, would you like to quickly introduce yourself to the listeners and viewers?

Steven: Yeah, my name’s Steven Sauder from zipfish.io. We make WordPress fast by optimizing the code that runs WordPress and the code that runs on the server.

Jonathan: Matt, would you like to quickly introduce yourself?

Matt: Sure I’m Matt Medeiros director of Podcaster Success at Castos, avid WordPress podcast or occasional product maker, a marketing person, and a business person.

Jonathan: The main areas we’re going to be covering in this podcast. Can we ask you Matt about this move to Castos? About his plugin easy support videos. What have been some of the trends and memorable things that he’s noticed in this most recent podcast from the Matt report? I’ve chosen four of my favorite. We’re going to discuss that. Then probably in the bonus content, we’re going to be discussing WordPress in general. You know, the leadership is automatically going to go public soon. A lot of WordPress stuff in the bonus content. Before getting the main part of the interview, I just want to do my spot forecasters, who are my main sponsor, and I’m very thankful that they chose me to be one of their long-term sponsorships. I moved to Castos. I just really loved it.

One of the really great things I love about it is the simplicity of the interface, yet it’s still really easy to use. What I mean by that is simple interface sometimes is not that easy to use. When it comes to Castos it is really easy to use. It’s such great value and they really helped me to move from my previous podcasting host. If that sounds interesting, it should for yourself or for clients, you really should look at podcasting to help you promote your business. Go over to Castos, have a look at what they could offer and I suggest you sign up. Hopefully, that was okay.

I’ve got the timer on. I’ll put it in the show [inaudible 03:13] you’ve been with Castos for about about 18 months, but you’re saying they actually being seen. I thought it was a bright move. I was really happy for you. How’s it been going in it? Has it been a bit of a surprise? Has it gone the way you thought it would go, Matt?

Matt: Jonathan you know this as much as anybody, I’ve been a podcaster for, nearly a decade now. I thought I knew everything about podcasting. I thought I knew about all the software, all the web hosts, all the podcast hosts that are out there, how people use podcasting. That was a huge surprise to just learn how big the industry actually is, how not so dissimilar it is from WordPress. Like, the cool kids at the cool lunch table in the WordPress world is here in podcasting 10X, because sometimes we’re talking about celebrities. That was just all really interesting to me.

I really love the role it’s a reason why I made the transition is because it’s a perfect fit for like, what I love to do, which is podcasting content creation, sales, product, marketing. It’s all of this stuff balled up into a day job. It feels great. I’ve been happy so far.

Jonathan: Yeah. I’m really delighted for you. When I heard the move, I thought, my God, what a perfect job for Matt. It’s the kind of dream job really Matt, podcasting, WordPress, all kind of big stuff together, like it was made for you.

Matt: Yeah. That was one of the things that Craig the founder of Castos, when he reached out to me, he kind of said that in not those exact words, but almost those exact words like I have a role I’ve made for you. I would love for you to come along for it. I was like, this is cool. This is great.

Jonathan: Right. It’s fantastic. Over to my right hand Steven.

Steven: What does somebody do? What does the day-to-day look like for a podcast success? It sounds like one of those like great titles that are just, I was listening to a podcast recently and somebody had the title of like director of tequila or something. That sounds like a fun job, but I feel like you definitely sound like you have one of those fun jobs too. I was just like it’s full of, I don’t know, like going on people’s podcasts and talking and meeting interesting people, what does that look like?

Matt: Yeah. There’s dynamic stuff and there’s static stuff. The static stuff is as a customer success person. When you’re wearing that hat, in a traditional software customer success role, it’s helping people understand how to use the software, obviously how to be successful with the software, are meeting the goals that the software is actually being built to use. It’s a little bit of that, but the interface of podcast hosting, once you learn it once there’s not many moving parts. It’s not like we’re rolling out like Asana or Base Camp where it’s like, hey, new feature, new way to do things, new workflows all the time. The podcaster part of that success is what it takes to actually be a podcaster.

Like if somebody who’s just starting out and they have a million questions, 90% of them are all asking about the hardware, which is pointless in the success of podcasting and creating content. But that’s where a lot of people start. It’s creating content, it’s doing live streams. We do two weekly zoom meetings or town halls. That’s like the static part of it like these are the things I have to do to help people become successful. Then the dynamic part is, guest appearing on podcasts. I also run the YouTube channel there. Just pumping out as much YouTube content I can, in the form of tutorials, in the form of industry stuff around podcasting.

Then hosting the audience podcast, which is Castos’ podcasts. That dynamic part, as you both know, like when you’re creating content, sometimes it takes you an hour. Sometimes you waste two days and delete everything. I’m working on a new onboarding video right now for the plugin. I’m in that creator mode where I’m like, I’m eight hours into editing like this one-minute clip. I hate this thing right now. I could just delete it, which is what I did largely before I was paid to be a content creator, that’s what I would do to my own stuff.

You waste time, you delete it, you throw it out, you start over again. That’s the life of an artist, I guess.

Steven: Do you feel like there are one or two things that make a podcast successful? Like if someone was going to start a podcast, what is the primary things that one focused on to be successful in that space? Or is it just vary so drastically between podcasts and podcasts, the audience that you’re going after?

Matt: Yeah. I mean, first and foremost as a host, if you’re about to host your own podcast, you want to focus on, am I serving and providing value to the audience, which is the obvious answer, but that means that there’s work involved there. Everyone says, yeah, you provide value to the audience and the work isn’t even really creating the content. It’s actually talking to the audience and finding ways to connect with them. I mean, you literally have to message people, ask people to give you feedback, DM them, get in a Facebook group, get in a live chat and really get that feedback to make sure that people are super happy.

The second is your own satisfaction with the podcast. Are you doing this? Is it feeling good? Because I think a lot of people start out and like episodes one through 10, super excited. I’m interviewing people. This is great. I’m making cover art. People are sharing my episodes and all that stuff. Then you run out of people after episode 10 to talk to, and you’re like, well, what do I do now? Then it becomes a chore.

Then you got people knocking on your door, wanting to be on your podcast and like all this stuff that becomes the burden or the work. You gotta make sure that the content that you’re after is satisfying to you. Are you getting your opinions out? Are you getting your thoughts out? Is it resonating with the audience and does it feel good to you? Then there’s like the other success that you can measure and optimize for money, views, shares, like all that stuff it’s going to come later and it’s always going to change. That target’s always going to move, but that internal creator you have to be satisfied with that first. You have to have a good following, whether it’s a following of 10 people or 10,000 people like you want to build that tribe.

Steven: Are there any metrics around, like how long a podcast has to exist before it becomes successful? Because like it’s small business. Everybody’s like, oh three years. Like most businesses fail within three years. If you make it past that point, you have a much larger chance of succeeding over the long term. You know, it’s funny because somebody asked me that same exact question yesterday and it’s going to change for every podcast. But here’s the thing. It’s like planting a flag in the ground. When you say you’re going to do a podcast, the only thing you have to do to convince other people that you are a successful podcaster is to not give up.

You could have zero listeners. You could have zero audiences, but the mere fact that at least the people in our space, in the tech space, and people who are savvy to podcasting, many of them know what the investment and what the challenge is to do a podcast. What I found is the mere fact that you continue to do a podcast, people will recognize you and say, she’s putting in the work he’s putting in the work. They know that you’re doing it and that you haven’t given up. There’s like this cognitive whatever. There’s this weight. They know it. They know that you’re doing it. They might not listen to every episode, which is what obviously I’ve found over the course of eight years in the WordPress space, it’s a trend, it’s a wave. People come in, people come out, new people, old people leave, people, come back. But not giving up. People still say, oh, he’s the guy that does a WordPress podcast.

Even in my local market, when I have a local podcast that I do for where I live south of Boston, southcoast.fm, it was like two weeks of me doing that podcast when it launched back in 2018, people who were already like in my local co-working spaces. When we were going to business events and stuff like that, they were like, oh, he’s the guy doing that podcast. You probably haven’t even listened yet. But there’s just the mere fact. So long as you don’t give up, it could be 10 episodes or 100 episodes. It doesn’t matter. I think that there’s a weight to the fact that people know you’re doing it.

Jonathan: Let’s talk about your new plugin, and then we probably go for our break. It’s called easy support videos. It’s for the backend, it’s for their admin, much easier to explain what it does a conductor. Is that one of the things you’ve learned [inaudible 13:01] and you were very generous giving me a lifetime license for that and it’s still going, but is that one of the things you’d learn from your experiences with the conductor? It’s gotta be easy to explain.

Matt: When I started the agency back intend of 2007, going into 2008, I was like every other WordPress agency. Well, not every, but almost every. Hey, this client’s stuff pretty tough. Let’s do this product thing, which looks so easy and everyone’s printing money. Let’s go after that. We went the route of WordPress themes. We were fairly successful with that. Then we got into the conductor, like seeing what we were doing with themes and then inevitably saying, wow, we should get into this plugin game too.

We’re building a version of conductor and to shorten this story, what I learned really quick, well, not really quick. What took me a lot of pain and money and time to realize was, it was too far ahead of its time. Jonathan, I know you had experienced with the conductor. Maybe some people listening have had it as well. We were trying to do what Gutenberg is doing these days, a block, move it around, and display content. Like the stuff that Gutenberg is doing in an obvious way today. We’ll have a query block inside of full site editing soon. That’s what the conductor was.

I was trying to shoehorn that into what everyone was saying was the future of WordPress at that time, which was the customizer. We’re all going to the customizer. I like turned to my team and I’m like, we’re going to the customizer. Let’s build this thing. We had a plugin called note where if you were in the customizer, just like you see with Gutenberg today like if you’re in a Gutenberg editor and you just hover over the places, you can put a block, you see a line that lights up with a little dot on it.

Like we built that, the plugin’s still in the repo. I should probably expire it. I don’t really know how to at this point, but you could do that same UI. Like we had built that in the customizer and I know there’s a lot of product owners out there who have been way too early to market. This is the same feeling. Anyone who’s launched something too early knows exactly what I feel. Back then I was like, well we’re going to the moon. When I first launched conductor, we sold $5,000 of licenses in a day.

I literally remember being on that YouTube live stream that I was announcing it and already thinking to myself, like, what color Porsche am I going to get? I just made $5,000 in an hour selling this product. I’ve hit it. It slowly tailed off. It did fairly well, making a few thousand bucks a month at its prime, but it was never enough for us to quit agency work and build a product. It was too complicated. It was too early and it was too much support. All of that is to say I realized over time that an ambitious product or a product with a lot of bells and whistles, there’s a lot of overhead there that many of us forget to take account for.

The more simplistic a product is, the more aha moments you can give somebody with less code, the better chances you’ll have. We had launched easy support videos. I think like three years ago in the WordPress repo. People were just using it, sending us messages. I love this thing. This is great. I’d love to be able to embed more videos or put videos on like a custom play. Speaking of advanced custom fields, I put it on my custom post types page to teach my customers how to use custom fields right inside of WordPress, so they don’t have to email me or call me or message me.

That’s how we built easy support videos. You can just embed videos inside of WordPress admin in a gallery page or on individual screens inside of WordPress. A little video pops up that you make as a consultant and it’s better to support. It’s easier to support. It’s a little bit of like, branding, a little bit of white glove. The customer feels a little bit more attached to you. We’re testing it out, seeing how it’s going. We have a lot of great feedback, but it’s low support people get it. There’s not a lot of development support to it either. Conductor was an absolute nightmare, supporting themes, integrations, all this stuff, and forget to explain what the WordPress query is to people, average customers, not even a chance.

Jonathan: Well, just to wrap up before we go for a break, Matt. It’s a difficult one, isn’t it? I look at Elementor. I think in your own podcast, you said that they were up to seven [inaudible 17:46] Do you go try and be an element. On reflection, I think to reduce the risks in some ways it’s better to go in with a product that’s a bit better than the competition, but the competition of sowing the seeds, but then it’s the marketing challenges.

Matt: Yeah. Launching a product in any space is difficult. It doesn’t matter if you’re selling ice cream down the street or if you’re selling WordPress plugins it’s very difficult to get product-market fit, to get awareness, and just to get all of the cylinders firing. A lot of it, as you said, is going to come down to sales and marketing messaging positioning. You know, and as a non-developer, the conductor was just too difficult or any codebase or any complicated product is going to be too difficult to support and build out while trying to do all this other stuff. It’s just a super-fine balance unless you have a boatload of money, and you can just keep throwing it at it.

But, we were trying to do the organic bootstrapped balancing act, and I feel like over the course of our themes and our conductor plugin, which was six, seven years, something like that. Collectively, we probably made a quarter of a million bucks in digital sales over six or seven years. There are people who print a quarter million bucks a month, with an element. There are people who print that kind of money monthly.

Jonathan: It’s not bad though is it?

Matt: It’s still was just never enough to like what you’re investing in, what you’re doing. It’s better than absolutely nothing. I feel like there’s some success in that, or at least that’s what I try to tell myself for reinforcement.

Jonathan: We’re going for a break, when we come back we’ll delve in a bit more about the latest Matt Report episodes. We were discussing where WordPress is and we’ve got a ton of stuff to discuss. We’ll be back in a few moments.

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Jonathan: Coming back. I’m under a little bit of pressure, the grandfather of WordPress podcasting with us. Matt, such a great guy. I remember when I first started podcasts, and my crazy cohost Bill, crazy Bill, who’s still a friend actually, but is bonkers as ever.

Steven: He’s on a horseback somewhere with six-shooters, just running around.

Jonathan: You agreed to come on the show. It was really bad. But I think you were my third or fourth interview and you just agreed to come on. I’m always very appreciative of you agree to do that, Matt, because you definitely didn’t need to do it. Before we go into the next question, I want to tell you about a webinar I’m doing with Spencer forum. You all know Spence’s on my round table show. This is our final webinar of a series of three that we’ve been doing that about his product LaunchFlows and also about how to combine it with a group of key plugins.

You can build for your clients or for yourself, really something comparable to click funnel about a fifth of the cost of something like click funnel. It’s gonna be amazing. Webinar’s going to be about an hour or less. You’ll be at the end of it around about the 40-minute mark, you’ll be able to ask us questions or ask Spencer questions. When are we doing this? We’re doing this on Friday the 11th at 10: 30 a.m. Pacific standard time. In all the episodes I’m all over the website. There is a link to the webinar. You go over to a page on LaunchFlows website. You just give your name and email. He just uses it to remind you a day or before the webinar date is coming up and you’ll be able to join us and ask questions. Should be a blast.

The Matt report. I think, some of the things like say I think a couple of the topics that seemed to come through it was headless WordPress and restless API. I think some of the shows that stuck in my memory recently was defining the chief operating officer that was with Lisa Wilson. I thought that was an excellent episode. WP crafts, Q L, Jason Bailey. I had to listen to that about three times. Talk about rich in content. Wow. Really fantastic guy and really knows his stuff. If you really want to get some understanding about it. I just loved it because he really showed some of the reasons why I still get excited about WordPress, because all these possibilities are an air map.

Another one knife, knife, [inaudible 25:27] and Paul Lacey. I know who Paul he’s coming on the round table show. He’s a great guy. I really thought that was interesting. You know, how do you build a podcast? How do you monetize it? obviously name for now is the public face of not WP Tavern, the podcast WordPress Tavern. Good luck to him. I think the last one, I’m a bit biased. Because if you’re Brian Jackson and Brian’s a friend of mine and he regularly comes on the round table show. I personally think Brian is one of the brightest people in WordPress. He’s so unassuming, but he’s a bit of a monster. What do you think about some of the podcasts I’ve chosen? Are they some of the ones that stick in your mind as well?

Matt: Well, I’ve noticed that you didn’t really choose any of the no code, low code episodes that I did. There’s a ton of WordPress podcasts that are out there. At the top of the show, we were talking about what makes a show successful. I say part of that is satisfying yourself as a content creator. What I’m trying to do is like, I’ve seen what WordPress has done, or obviously as a user for the last 12, 15 years. Then as a podcast host over the last eight to nine, and I’ve seen what people have done in terms of like excitement, like what has really made people excited about WordPress, and back in the day, it was just the mere fact that there were all these themes that you could quickly install.

Then the rise and fall of like theme forest, and like code canyon and like what people were doing with it. Then page builders came along like that same excitement. Really it is all boiling down to enabling and empowering somebody to build something without any real coding development. Let’s be honest here. I think the content that still does the best in the WordPress ecosystem is developer-focused because that’s how many people, like, if you look at any top like WordPress news site, it’s the ones that you always get the most votes is like, I dunno what a tab space, your functions, PHP files. Why? This is what’s winning. It’s okay. That’s fine. Then there are the end-user tutorials because I have the plugin to a YouTube channel, which I’ve sorely neglected since I started Castos, because I’m so busy.

But that kind of how to use something is is super popular. The business, the marketing, even like the community-focused content, unless it’s coming from.org is not, you just don’t …

[crosstalk 28:15]

Jonathan: I know what you’re going to say because I think that’s the stuff you really interested in, and that’s the stuff I’m really interested in as well, but it’s not the most popular, is it right?

Matt: Like you look at WordPress on a global scale and as big as popular as it is on the internet, there’s only like 1% of people who actually care about it. The majority of that tiny fraction are largely developers. Then there’s like the business people in it. Then that shrinks even more. This doesn’t really answer your question, like what my favorite shows are, but what I’ve been trying to do is look at what and how and why WordPress was so exciting for a lot of people. Then look at other markets like no code and say, look how excited people are to use this platform called Bubble.

They’re building businesses, just like people were with WordPress, it’s powerful software. It’s empowering them to do things that they can’t really do nor have the time to do or the money to do just like page builders and even like theming, WordPress was ACF Genesis and all this stuff and all of that same thing. I am foolishly trying to combine the two worlds because I think there can be crossover I think that there’s an agency or a WordPress freelancer out there, who stops looking at WordPress as like the entry-level solution and be like, you know what, this takes time, planning, money, management, support. We’re going to elevate WordPress up here.

Maybe somebody coming in who doesn’t have a budget and I need to do this fast. Let me go to web-flow, let me bring web-flow into my toolkit or another piece of software. Or they want to get into like app development. We’re looking at WordPress as the hammer and let’s go after all the nails with WordPress. Well maybe if you’re going to build a traditional web app for somebody, maybe WordPress isn’t the answer. It’s Bubble. Then I’m also doing SaaS, software as a service. People like Brian Castle and, a bunch of other folks who there is WordPress crossover there, cause a lot of people to use WordPress as a springboard to SaaS or your traditional SaaS, but just trying to cover all the bases these days, with the Maryport to try to broaden, the awareness.

Jonathan: That’s what I’ve been trying to do. I’m not sure how successful I’d be.

Matt: I think this is what everyone, has to do. For me, new branding constantly likes always evolving the brand. I try not to leave it stagnant. I launched the WP minute podcast and that’s for me to be like, look, this will 100% be WordPress all the time. Like this it’s the WP minute, so you’re not going to cover anything else. That’s to keep people connected to WordPress. That’s my strategy through 2021.

Jonathan: I felt, the interview with Lisa Wilson, as she came across, she was so honest with you about all the balls that she’s juggling. You too, like three years ago, it sounded like they were having a tough time competing with adobe. That’s died down. I got the impression what she was saying that’s died down a bit, but adobe really gunning for them, and some of the other larger agencies like Tune-up. I was hearing that they, because of that they were pitching for other jobs that they normally wouldn’t.

That was having consequences for the tiered two WordPress agencies because the bigger agencies were encroaching. It was tumbling downwards really. But I think that’s plateaued to some extent. Do you think I’m right about that, Matt?

Matt: Yeah. I mean, when you’re the size of a web dev or the size of a 10 up it is a competitive scene. It is no doubt about it. I’ve known Lisa and Brad for a long time. Obviously consider them, close friends. We talk often. She’s super smart. I think there’s again, like when we talk about like products, people think, oh, you’re just like I did, launch a product, buy a Porsche, right. That’s what everyone does. Then you realize that there’s so much other overhead that goes into this stuff, the same thing with agency life. Like if you really truly want to scale an agency to that size there’s stuff you have to think about.

A chief operating officer is certainly one of them and it’s somebody who oversees the operations of everything. You have to have somebody as sharp and as experienced as Lisa to understand sales, marketing development, branding, messaging, client services, support like hiring HR. It’s a massive role, COO and it’s a tough game when it’s that competitive. Another episode that just came to mind, I’m gonna forget the guy’s name, but if you just search on my site Barrel Agency, like roll a barrel down a hill, Barrel Agency. He uses WordPress, but they’re a New York-based agency. It’s a small issue shop.

I want to say maybe like maybe 20, 25 people. But that was a fantastic episode as well. By far, one of my favorite episodes was years ago with a good friend of mine, Jose Kabelur. He worked for Razorfish, which was a massive agency, many years ago. It was just a fantastic conversation. He did something called the Skool. He was talking about selling six-figure contracts to customers because that’s what he was doing at Razorfish. I mean, that six figures was just entry-level right. For a lot of those people. This is when I was a young podcaster, content creator. The title was how to charge your clients a hundred thousand dollars per project. I guess back then my SEO was good.

In like a couple of weeks, anyone searching for him to hire him as a creative director was finding my podcast episode with him. He was like, hey man, can you change that title? Because people are reaching out to me to do work. They think I’m going to screw them by just simply charging them a hundred thousand dollars. He’s like, could you change that title? I’m like, yeah, no problem. That also a fantastic episode. He’s a great guy.

Jonathan: Yeah, that’s Great. Well, we’re going to wrap up the podcast, the show, but Matt’s agreed to stay on for our bonus content. In the bonus content, I’m going to let Steven have a question. We’re going to be discussing how WordPress in general is doing automatically. There’s just a lot of stuff. I’m going to give some of my opinions so I can kill myself. It should be great. Join us and you’ll be able to watch the bonus and the whole interview on the WP-Tonic, YouTube channel. Steven, what’s the best way for people to get hold of you, Steven?

Steven: Head over is to zipfish.io run a speed test, see how much faster your website can be.

Jonathan: Yeah. Steven’s really helped with the WP-Tonic website. Made it more of a speed machine, not a Lego. Thank you for that great team. Matt, what’s the best way for people to find out more about you and what you are up to Matt?

Matt: Day job, castos.com. If you want to start a podcast Matt Report. If you’re interested in my podcast, but everything I do is crafted by matt.com. It’s absolutely everything I do.

Jonathan: That’s great. Remember, you’d want to listen to the bonus content, go over to the YouTube channel. We’ll see you next week. Thanks for listening. We’ll see you soon folks.

 

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