In the last episode of the year (and a bonus one, to boot), my friend Jeff Large interviews me as a follow up to the 100th episode. Jeff is a great interviewer and I really enjoyed the conversation we had – he even gets me to say, “trade secret…” I think you’ll like it too!

Show Notes


Intro: Hey, everybody. Welcome to a special episode of How I Built It. My 100th episode came out earlier this year, and my original plan for it was to have somebody interview me, turning the tables where they are the host and I’m the guest. Unfortunately, I couldn’t get something like that done in time, due to schedules and a bunch of things. But my friend Jeff Large recently reached out to me and asked if it was something I’d be interested in doing. Naturally, I said yes. He listened to the 100th episode and then asked me a bunch of follow up questions, digging into my history as a web worker, a podcaster and an educator. And of course, he asked me if I have any trade secrets, and it’s a good one that I  haven’t shared on this show before. If nothing else, be sure to listen to at least the trade secret part. That’s it. There’s no sponsors or anything like that in this episode. This is a bonus episode. And with that, I will turn it over to Jeff.

Jeff Large: Hello, Welcome to How I Built It. The show where we interview product owners and developers about how they built specific products from idea to execution. I am your honorary guest host and podcaster, Jeff Large. My guest today is someone you know and love if you’ve been listening to this show for any amount of time. He is a college professor, online course teacher, web developer of over 17 years, and the otherwise normal host of How I Built It, Joe Casabona. Joe, welcome to your show.

Joe Casabona: Thanks, Jeff. I’m happy to be here.

Jeff: This is funny. We jumped on– Just for context for the audience, we’re friends in real life, and we were talking on slack. I pitched the idea to him that to end the year we did an interview, and then you were just telling me that you wish you would have done this. Or, you wish you had reached out to me already for episode 100.

Joe: I had this grand vision of somebody interviewing me for episode 100, but then a lot of things happened and I was delayed, and I was like, “I don’t want to have to try to schedule somebody, and rush,” and stuff. So I did a scripted version of that. But I’m happy that we get to do this, because I would love to answer questions that people have about the show.

Jeff: 100%. Especially if you have listened to episode 100 already, I just listened to it and used it a little bit as a launching point. But we’re definitely going to get into, you and I were talking beforehand. I want to get into more of your actual business. The podcast is one side of it, and I  have a feeling that it’s a little more of the marketing piece as opposed to the actual moneymaking business parts of it itself. For you to be running this show for so long and to be interviewing so many amazing people, I assume that your listener base would like to know a little more detail than you  share on a regular basis about what’s really going on about your journey, about the stuff behind the scenes. That’s some of what I want to get into with you.

Joe: Awesome. That sounds great.

Jeff: All right. To begin with, this is something that I like to ask people on my own show. You’re responsible for multiple things, like I alluded to in the intro. How do you normally introduce yourself?

Joe: This has changed recently. I used to tell people, “I’m a front end developer that also teaches and podcasts,” but over the last few months people have asked me, “How come you’re not telling people that you’re a college professor? How come you’re not telling people that you created these accredited college courses?” Now I say, “I’m a college accredited professor who creates online courses, a front end developer and a podcaster.” That captures a little bit better my core competencies and the stuff I’m focusing on a lot more now.

Jeff: Do you feel–? One thing I was wondering about even that sort of branding. The word “College accredited,” has that made a difference? Does your audience, and the people in your target audience, do they get it? Because even for me, being in the education space, I had to double– You saying “I’m a college professor” registered, but “College accredited course creator and professor” threw me off a little bit. It almost felt too wordy.

Joe: It’s funny you mention that, because I was just talking to a coaching client that I got recently who  hired me because of my college background. She asked, “What do you mean by college accredited?” Perhaps in a future bio will remove that, and then just mention that I’ve developed middle-states accredited college courses. Because that’s what I mean, is that I have developed courses at the college level that have gone through the rigor of getting certified and accredited.

Jeff: Because that is a valid point. I don’t want to discredit it, I just felt the wording of it didn’t mean anything to me. I was like, “What does this mean?” That’s why I was curious. Because you do get set apart in the sense of– I don’t know. You and I have talked about this as well, this is a tangent for a second, but it seems like in some circles and in some aspects of the people online to be an expert all you have to do is say, “I’m an expert.” That’s frustrating for the people that actually know what they’re talking about, and for you to have these credentials where you have a master’s degree and you’ve been teaching at the collegiate level. It seems like to be able to convey that in some way is important.

Joe: Definitely. A lot of people, I have fallen into this myself too, “I do something and now I can teach it.” I built a single website with some WordPress plugin, therefore I am qualified to teach a course on it. I’ve tried to step back from that a little bit, but I do want to convey to people that I am a web developer. I’ve got all of these 10 years’ experience teaching college students and developing college courses, where people are learning a real tangible skill for their professional life.

Jeff: That’s a big deal. To run down your background then, because I want to focus a little bit more on how you built the business that you have today, and this year. But to give context for the listener, if this is someone new or maybe they don’t know, I’m going to run down and feel free to correct or clarify anything that I’m saying. You have your degree in information technology, and a master’s in software engineering. You originally got into web development when you were 15, for your church you built your first $200 website. You have been teaching college level courses since 2007, so a little over 10 years now, and you spent a significant amount of time working for Crowd Favorite building enterprise level websites. This means big sites for important people, is what that comes down to. It wasn’t until, it looks like last year, June of 2017 that you left Crowd Favorite in order to pursue your own projects. Is that a good snapshot?

Joe: Absolutely. As you mentioned, I’ve been freelancing since I was 15. But the whole full time business with real stakes, let’s say. Because after college I freelanced a little bit before getting a job at my alma mater. But I have a family, and rent, and bills and stuff now. That I’ve been doing full time since June 2017.

Jeff: OK. That is a big difference. Is there anything–? I don’t want to spend a ton of time here, but what do you feel were a few, three at the most, top takeaways from that period of time? From the time that you got your feet wet, you got into web development, started teaching, and you were working for this big company. What were a couple of things that you were able to– The wisdom that you were able to take with you from that experience as you started your own thing?

Joe: That’s a great question. The first bit of advice is something I got from Mr. Joe Rizzi. He owned the deli that I worked for. I am a stereotypical New York Italian, so of course I worked for a deli.

Jeff: Is your accent going to come out in the story?

Joe: It might, a little bit. We’ll see. I’ll try to keep it to a low burn. When I first started making websites, I was charging $10 an hour. And I told him this, and he said, “Joey. Do you do good work?” And I said, “Yeah.” He goes, “Why are you only charging $10?” And I’m like, “Because I don’t think people are willing to pay that much more.” And he said, “If people see your prices are too low, then they won’t go with you. They won’t think that you have good quality.” That was the first time I raised my rate to $25 an hour. That advice, and basically all of our conversations, I would always stay and clean up on Saturdays and he would give me business advice. But that was my first big takeaway is that price communicates value, and that people don’t just want to– Real people don’t just want to go for the lowest price. They want to go for the price that will deliver the most value for them. That was  one of my first big lessons. The second big lesson I got is something I was told when I was about 21 or 22, and didn’t realize until I was about 30. Because you don’t know anything in your early 20s. That was from a family friend who said, “Look, Joe. I know that you want to start your own business, and that’s great and everything, but when you get out of college you should go work for a company in the same line of work that you do. You can network, you can learn those processes. You can get real world experience. Then when you go out on your own you’ve built up this network of people who then you can tap into.” And I thought, “I don’t need to follow that advice. I know what I’m talking about. I’m in my early 20s, I know everything.” Then when I was about 30, working for Crowd Favorite, and seeing all of the things that I didn’t know. I thought, “Man that was advice that I wish that I took.” Those were two lessons I learned in my teens and early 20s that helped shape my business, and the third bit of advice came towards the end of my time at Crowd Favorite. Maybe right after I left Crowd Favorite. That was that your messaging needs to be right. To expand on that, all of my client work has been word of mouth since I was 15. My first paying gig was my first gig because my church said, “We’ll pay you.” I didn’t even make websites, they were just like, “Will you make us a website?” And I said, “No.” And they said, “We’ll pay you.” And I was like, “OK.” So I never learned the lesson of the hard fought client, or at least not really. That is something that I’ve learned over the last two years is that people who don’t know me, I need to gain their trust first before they’re willing to give me any money, because my cheapest courses are $20-24 bucks and if they don’t trust me, they’re not going to hand over that $20 bucks. Those are maybe the three best lessons that I’ve learned over the last 17 years.

Jeff: That’s fantastic. For context, if you don’t mind sharing, how old are you?

Joe: I’m 33.

Jeff: OK. Cool. That gives us a little bit more of a timeline. So, that moment. Tell me about the moment that you knew you needed to leave Crowd Favorite.

Joe: This is something that I remember in a haze of not remembering much, because it was a couple of months after my daughter was born. She was our first. She still is our first, and I was doing a lot of things. First of all, Crowd Favorite generously gave me one month paid family leave. That’s not something that you see everywhere, especially for the guy. My friend who just had a kid said he had one day. That is insane. But that’s grandstanding. So, I had a month off where I got to spend time with my family and I got to work on my own projects, and I liked that. Then about two days before I came back, about a week before I came back, somebody put a meeting on my calendar for before I was supposed to come back and I was like, “I’m still on family leave,” and she’s like, “Can you just–?” And I said, “No.” Then when I got back, everyone was like, “We’re real glad you’re back.” And I’m  like, “That’s not a great sign.” I got handed these four projects, I had just got a promotion and I got handed four projects that needed some love, to put it nicely. So I had a newborn, I had my side business which was these courses and the podcast, and then I was doing the agency life. I was working until 2:00, 3:00, 4:00 in the morning just to get up at 7:00 or 8:00 and do it again, if I didn’t get up with the baby at all. I know that GaryVee endorses that lifestyle but I don’t. I thought, “All right. I either need to give up my side hustle, spend less time with my family, or quit my full time job and pursue this full time.” I had some conversations with some friends, and I thought, “I can do this.” I gave my notice in May and I left in June.

Jeff: How far after then, if you left in June and you gave your notice. From the time that you gave your notice, how far after since when you went back? You went back, there was a period of time, then you gave me your notice. How long was that timeframe?

Joe: Good question. My daughter was born on March 6th of 2017. I had a month off, so I came back on April 6th or April 7th. Something like that.

Jeff: It was within a month, then, of coming back.

Joe: I realized pretty quickly. Because that whole month I was like, “This is so nice. I’m working on my own stuff. It’s making some money. I’m doing really well.” To be totally frank, this was at a time where a lot of WordPress agencies were having trouble getting work, so some paychecks were delayed. I thought, “I’m not suffering at all because I’m bringing in enough money from my side work.” Then when we got to a point where it was like, “Finish this project or payment will be delayed again.” I was like, “I would just work for myself if I had to do that. Like, I’m working for a company so I don’t have to worry about that.” And again, this was not a strictly Crowd Favorite thing. This was something that was common among a lot of WordPress agencies at that time. I knew pretty quickly that I either had to work myself to the bone at this job, this agency job, and lose time with my family. Or, see if I could make my own lifestyle business and spend time with my family and make enough money to support the family as well.

Jeff: What was it like to submit that notice? How about that?

Joe: It was a little– It was tough in some regard. But I was also, I was also already unhappy. So I knew I had to give the notice soon if I didn’t want to end up completely resenting Crowd Favorite, because I wouldn’t be where I am today without Crowd Favorite. The skills that I developed and the network that I developed while at Crowd Favorite has done wonders for me since then, and I didn’t want to end up resenting the company. So I spoke to the then CTO, he still is the CTO, and I aired my grievances a little bit. I said, “Look. Agency life was great when I was a single man. I didn’t mind staying up super late to do work. I didn’t have much of anything else going on. But if I missed my daughter’s first steps because I had to work late, that’s not something I’m OK with.” And he was so cool about it. He was like, “There’s no convincing you. We’re going to miss you and I wish you all the luck in the world.” I’m still friends with everybody at the company. There was no bad blood there. But they were cool and super understanding, and I think that I happily got out before I was mad about it.

Jeff: OK. Overall it sounds like it was a pretty– I don’t want to say it was easy. It sounds like it was  understandable, and an OK decision to make.

Joe: Of course I had conversations with my wife, going out and starting your own business with a three month old is not desirable. Especially because my wife was still on maternity leave and FMLA only covers so much. We’re going to be only my income for a while in this brand new business, and she was  fully supportive. Because she saw how much doing all three was wearing on me.

Jeff: That’s absolutely tough. I look back at even my own experience and having to turn in that letter, and having a family that depends on you. At the time we were a single income family and we had– I don’t know what your situation was like, but we had about six months’ worth of savings. My wife and I were  running the stoic philosophy of, “OK. What’s worst case scenario? I have to go back to work in six months if I get no jobs whatsoever. All right, let’s do it.” Did you have some money in the bank, or did you have any much of a runway at that time?

Joe: We had about the same. Granted, that was also money we were saving for a house. So I was reluctant to have to pull from that. But I said, “Look. The money we have in our savings will get us through December. If I completely fail at this, worst case scenario, I’ll get a job.”

Jeff: Definitely scary. I wanted to dig into it because I know other people, I’m sure there’s listeners that you have, like you’re listening right now and you might be debating this. It’s definitely a big jump and it’s a scary jump, and sometimes you hear about the more romanticized version. When it’s like, “I was making more money in my side hustle than I was at my job. So I knew. Forget you people, I’m doing the side hustle.” But when in reality most of us are like, “Well. Here we go.”

Joe: I was definitely helping make ends meet with my side hustle, but it was definitely better as a side hustle than as a full time job at that point. Because any money on top of my salary and my wife’s salary was great. That was extra money. But then it was like, “This is the only money we’re making for a little bit.” I had a better first year than most, but I’ve also been doing this for a decade and a half, in some capacity. I have a big network. I’m an outgoing guy and everybody I meet, I talk to and I know their story. You asked me at Podcast Movement, “Do you consider yourself a connector?” And I didn’t, but now I do. I like connecting people. I like knowing people, and I do good work. That’s  helped me do more than just start from scratch or ground zero. I’ve had a better first full year than many, and I’ve been able to support my family, and my wife is not saying “You need to find a job, a real job.” But it is a grind. There are some slow months where you’re like, “Am I doing the right thing?” Just keep that in mind if you’re going to start your own business.

Jeff: For sure. In that vein then, you leave. How did you know what the first thing to work on was?

Joe: Luckily, I had that lined up before I even gave my notice. I spoke to my friend [Sean Hesscath] from WP101 and I laid it all out on the line. I’m like, “Sean. I don’t know what to do. This job is killing me, I’m doing too much. I’m sleep deprived because of the baby. I want to go out on my own but I don’t know where to start.” And he said, “How much money would you need to get started?” And I gave him a number, and he said, “I think I can give you that much in work.” Right after I left we got started on  collaborative courses that I did for WP101. That meant a lot to me because I was able to make the income I needed while also working on my branding, working on the podcast, LiquidWeb has also generously sponsored this show for a few seasons, and their full season sponsorship hit the July after I left. So, Sean and LiquidWeb floated me through the end of the year and that gave me enough runway to understand what I needed to do with my business.

Jeff: Interesting. OK. Do you feel like you would have been able to–? That’s hypothetical.

Joe: I don’t think so. But that goes back to the network that I built. I’ve known Sean and Chris Lema from LiquidWeb since PressNomics 2 in 2014, and I’ve maintained that relationship. They know the quality of the work I do and they trust that, and I deliver for them. It seemed like luck at the time, like we hit at the right time. But those were relationships, and also they’re both insanely generous, don’t get me wrong. But they’re running businesses too, and they have families to support. Those were relationships that I cultivated over three years or so, that I’ve been able to work with them and partner with them, luckily still today.

Jeff: That’s going to be a common thread that’ll come back up, because it’s even something I just had– I jumped on a call with a friend of mine who’s acted as advisor here and there, and I haven’t talked to him in a year and a half but I had a question come up that I knew he was the key person for. I emailed him and I was like, “Can we chat?” Even some of the advice that he gave me was just building those more long term relationships. It’s not even– It’s weird because on one hand you know you’re going to benefit from it, but at the same time that’s not why you’re doing it. You’re doing it because they’re cool people and you want to be part of that group, you want to be part of that network because you know there’s things that you can contribute and you know there’s things that you’re going to gain. Hopefully it’s the rising tide philosophy, where everybody is going to benefit from being able to rub shoulders with one another.

Joe: Definitely. Again, I was on a coaching call before this and it’s a little bit weird sometimes,   taking someone’s money for them to ask me questions. It is a service and I’m saving them time, but she said, “The best relationships are win-win. I’m getting a lot from you, you’re getting a lot from me. We shouldn’t feel bad about benefiting.” I agree. If you are doing it for the wrong reason it’s super obvious, like I used to run a meetup group in Scranton and this guy came to the meetup group. He just looked smarmy. He went over and shook everybody’s hand, gave everybody his card, and then left. Like, you’re not there for the community. You’re there to try to piggy back off of and make money off of these people you just met? People see right through that. Even if they don’t realize it, they’re like “Something’s off about this dude. He’s not somebody I want to work with.” But if you’re genuine and you want to help, then people see that too.

Jeff: Be a good human.

Joe: Yeah, be a good human.

Jeff: So much of life comes back to, “Be a good human.” That’s awesome. So, I want to fast forward now. We had this, you were able to float that first year and start to get your legs underneath you with it. When do you feel like you had your first major breakthrough of something– I don’t want to discredit what you gave us, having Sean come in and having LiquidWeb come in and help in certain ways. Not that you didn’t earn it, but there’s a reciprocity there. What was the first project or the first thing that you came across where you were like, “This is my doing and it’s working.” ?

Joe: That’s a great question, because you’re absolutely right. Even as recent as over the summer, I was like, “I don’t know if I actually know what I’m doing.” But the first big hit for that was I did some work with WordPress VIP in January-February. They reached out because of the courses for Gutenberg that Zack and I did, and they liked it, and we were first to market. Sure. But they knew that we were good educators and they wanted to bring us on to create educational content for their clients. And I thought, “This is great. Automattic and WordPress VIP are reaching out to us for the work that we did,” but also at the price that we gave them, they said, “That’s above our budget but we definitely know what you’re worth. We understand what you’re worth, so can we just cut some stuff to get it within the right budget?” That was so much better than just saying, “I can’t afford you,” which is what a lot of freelancers hear. “Can you do it for less?” No. The way that they handled it was they were like, “We understand the quality of the work that you’re giving us, and this could be a win-win for both of us.” And right there I was like, “This is going to be a good year.” It happened in January and it made me feel good about the rest of the year, and I’m pretty optimistic as we end 2018 moving into 2019 that I’ve learned enough to continue that trend and finding the right people to work with.

Jeff: That’s fantastic. That’s great news, and even as a freelancer. If you’re a freelancer listening to this, don’t discount. Remove aspects of the project if that’s what you have to do. Sometimes you won’t get a prospect or a client that’s as gracious to understand, and they’ll just say, “Can we take 10% off the top?” Then unfortunately, especially when you’re in a tight spot or if you can be in a tight spot, you’re like “Sure.” Where it’s like, “No. I’m not going to do that. But what we can do is these two parts aren’t necessary, so let’s go ahead and remove those. That’ll get it into the price that you want. Will that work?”

Joe: I’m a big proponent of setting up Phase Two. “We’ll do this now. This is what we need to launch. This is our MVP. Then when you’re ready and you have the budget, we can do these in phase two.” You’re guaranteeing yourself more work, you’re working within the client’s budget, and hopefully you’re forming a good relationship around the first project that they want to come back to you for more. In college I used to fix computers, and for a long time I did it for free. I would go visit my friend   and then her whole floor would come over and say, “My computer’s not working. Can you help me?” I was like, “I’m going to start charging.” And I started charging some insanely low price, like $5-10 flat. Like, “Give me $5 and I’ll fix your computer.” Most of them took less than a half hour. I could do it pretty quickly, but nobody really wanted to pay that because we’re all poor college students and they would rather frankly go and spend the money on booze. Somebody very snarkily said to me, “So how’s that charging $5 for fixing computers? Are you getting a lot of money?” And I’m like, “No. But I have a lot more time on my hands to work on things that people actually see the value in.” So, definitely don’t discount that. Work with people who value your work because those are better relationships.

Jeff: 100%. To fast forward now, to roundabout back to the beginning. You’re doing some freelance work, you’re creating your own courses, you have the podcast and you generate some income from that with your sponsorships. How do you see this? How’s your time breaking down? Think of it in terms of  percentages. How much time percentage-wise in your day, like your work day, do you dedicate to those different things?

Joe: I dedicate 60-70% of my time to my courses. And that’s an umbrella term, that’s an umbrella percentage for planning and recording, learning the thing that I’m teaching. If I’m creating a custom course for somebody, and then the marketing stuff. Getting the marketing message right. Building the landing page and communicating the problem I’m trying to solve and not just what you get. 60-70% of my time goes to that. Thanks to a bunch of automations and hiring the right people, podcasting probably takes up about 15-20% of my time. It’s mostly just the interview now. Again, that’s thanks to automations. I touched on this in episode 100, but I’m going to work on a blog series about this too. The rest of the time, which if I do my math correctly, leaves me with 15-20% or maybe 20-30%, that’s hired work. Custom courses that I develop and custom video trainings that I develop for people who own product. Coaching, I’ve been doing more of that lately. Maybe 33 is the magical age where people feel you know enough to help them now, or what. But I’ve gotten a lot more organic traffic to my coaching services lately, and that’s going to be a big part of my 2019. This one-on-one teaching style that I really like.

Jeff: All right. That’s cool. I don’t need to know the actual numbers, but do your finances reflect the same percentages in terms of your income?

Joe: No. My courses make the least amount of money right now. And that’s because of some lessons that I’ve learned this year. My courses would be– Let’s take the my podcasting one. Build a Podcast Website with WordPress. Nobody cares about that. That would be like somebody saying, “Learn how to build a car with steel,” or something like that.

Jeff: “Learn how to draw with a pencil.”

Joe: Exactly. Nobody cares about the tool that you’re using. People care about the problem that you’re trying to solve. People are buying a solution. I’ve pivoted a lot of my copy in the last few months to reflect that. So now, it’s “You have a podcast. How do you get it into the ears of people? You need a good website.” “But I don’t want to hire a developer.” “Don’t you worry, my course will show you how to launch your podcast in three days.” “Three days? That’s not that much time. Great.” That’s the problem that’s being solved. I’m optimistic. First of all, from 2017 to 2018 my course income quadrupled. Don’t assume I’m making a million dollars off my courses, assume I made shockingly little off my courses in 2017 and I’ve gotten much more in 2018. I’m hoping to double or triple that again in 2019, maybe even more. Because I’m working on a couple of in-person-ish coaching courses to supplement my pre-recorded stuff. But the short answer is, no. My courses make the least amount of money but they take the most amount of time.

Jeff: But you’re looking at it, what I’m hearing though is that your business plan is for that to change. For the courses to be able to take more of the– Provide the bulk of your income.

Joe: Exactly. I want to teach people the things that I’ve learned over the last 17 years. I want to help them. If you can imagine a freelancer takes one of my courses, maybe the Beaver Builder course. They take it they like it, now they want to go to the next level. Now I can do one-on-one coaching with them. I want to fast track the site builder or the freelancers career to accomplish in two years, maybe, what I accomplished in 10 years.

Jeff: That’s cool. Is that built into your–? This is a side question. Is that built into your funnel, then? Do you have hopes or intent of people to go through your courses, and then they all of a sudden have this opportunity to get personally coached by you?

Joe: Again, that’s a change that I’m making. My 2018 was the year of understanding the people on my list and in my funnels, because in 2017 I used MailChimp and up until recently MailChimp didn’t allow for any of that. So I got ConvertKit. I’ve had ConvertKit for a little bit over a year. I’ve tagged everybody appropriately, I know what my audience looks like now, so the two weeks between Christmas and  before Christmas and right after New Year’s, I’m going to spend some of that time working on my funnels and getting my messaging right. Making the next steps explicitly clear. “You haven’t bought a course from me, here’s some free resources. Do you like these resources? Maybe look at this course, because this will really help you.” “You’ve finished the course. Congratulations! What questions do you have? Maybe let’s schedule a call, 15 minutes, and we can talk about it more.” “How can I get you to the next level?” That sort of stuff.

Jeff: That’s so big. Understanding the audience and understanding who you’re talking to, it’s some of the lessons even that I’ve been going over lately. They come more from a marketing space and more from a  really good copywriting space, of stuff that I’ve learned from say Joanna Wiebe from Copy Hackers or other people that are in her group. Where instead of just waking up and being like, “I got an idea,” and then writing about it. Or, “I need to sell this thing. Let me talk about it in the way that I’m going to talk about it.” Spend time understanding who you’re talking to, what their pain points are, the actual language– The verbatim phrases and words that they’re using to describe these issues, and then incorporate that into what you are doing. Care deeply about them. Care deeply about the people you’re already working with even more, and then secondary, start caring about that target audience or  the people that you’re going after. Really understand their world because there is a certain amount of, some people refer to it as the curse of knowledge, or things like that. Where you’ve been in a space for a while and you just forget. You forget what it’s like to learn, you forget what the problems are, because you’re just beyond that. It’s not really even a hierarchical thing, it’s just you’re better because you’ve done it longer. You have to almost look at it like a kid or look at it how like a child would.

Joe: Absolutely. I realized that teaching in the classroom. My time teaching in the classroom has been insanely valuable to me, because one day I was like, “I’m going to set all my students up on They should all know this.” I talked about your personal brand, and what that means in the 2010s. I said, “OK. Here’s WordPress. Here’s a post and here’s a page.” I went through the stock description that I gave, because I assume everybody knows what a post and a page is, and one of my students raised her hand and said “I have no idea what you just said. What you said makes no sense to me.” And I said, “Yes. Let’s step back.” Then I brought up BuzzFeed and I said, “Here’s a post. It’s an article. Here is a page, you’ve probably never gone to the BuzzFeed about page because it’s irrelevant content to you, but this is a page that never changes. Your articles, see how they’re all listed in a certain way, and categorized and stuff like that?” Then it made a lot more sense to them. “Talk to your customers, have phone calls,” that has come up in conversations I’ve had a lot this year. Don’t just email them and say, “What’s your biggest problem?” Actually have phone calls with them and have conversations, and write down the terms they use, because that should be your marketing copy. Because now you’re speaking the language of your target audience and they’re going to know that you understand their problem.

Jeff: Do you consider yourself a specialist?

Joe: I don’t call myself a specialist, but I specialize in certain things. I’ve been working with WordPress for 14 years. I’ve been working with WordPress almost as long as WordPress has been around. So, am I a WordPress specialist? I guess so. I’ve been teaching for 10 years. Can I show people how to teach, or can I at least show them my teaching method? Yeah, I guess so. I don’t call myself that, but I wouldn’t– If somebody categorized me that way I wouldn’t say they were wrong.

Jeff: One question that I had come up with another person who I was telling that I was going to interview you, is they were curious on how you do your pricing. Actually, let me pause. Will you answer that with what you learned from Cabo?

Joe: Yes.

Jeff: All right. Let me ask a different question. Let’s hit the brakes on that one. I know you’ve done some different things this year, and that’s what leads me into the Cabo thing. You’ve done some different things this year that you’ve shared, just in some of our personal conversations, that have really made a big difference in your business. CaboPress seems to be one of those events that’s helped you on a personal and a professional journey. First of all, for somebody that doesn’t know, what’s the two sentence pitch on what CaboPress is?

Joe: CaboPress is a conference for business people, and it used to be specifically around the WordPress space. But it’s– Let me rewind, actually. Because I don’t think I’m doing CaboPress justice when I say that. CaboPress is like a hyper-targeted networking event. The attendees are curated, the hosts are curated. And yes there are sessions in the morning, but the big value comes from the conversations that you have outside or during those sessions, because even the sessions are supposed to be conversations. You can think of it as a four day hallway track in paradise.

Jeff: I love it. OK. All right. So, that’s what CaboPress is. You can learn more– I’ll just plug it right now, we’re not getting paid for this or anything, I just know it’s cool. if you want to learn more. So, how many years have you attended so far?

Joe: This past year was my second.

Jeff: OK, the second time. Is it worth focusing any time on year one, or is it better just for us to talk about year two?

Joe: Year one was insanely valuable to me, and we already talked about it. Year one is where I decided I was going to use ConvertKit to understand my audience.

Jeff: OK.

Joe: CaboPress is what convinced me that I need to do that.

Jeff: Who convinced you? Was it a group of people, or a specific conversation that you remember?

Joe: It was the knock on effect. The first the first talk of the day, of the week, was Chris talking about understanding your user’s lanes. Or, user lanes, and understanding who your audience is so you can better talk to them. He mentioned ConvertKit and Drip and a couple of other ones. Then I was talking to other attendees later, [Erin Flynn] specifically, and she was telling me how she loves ConvertKit. So she gave me her affiliate link, I was like, “Do you have a link?” And she said, “Yeah.” And I signed up right there in the pool.

Jeff: The things we can do with technology. Year two, how did year two make a difference?

Joe: Chris looked at Joe Casabona and where his business is, and what he learned in year one, and then said “How can we improve it in year two?” Because in year two we talked about personalization. This is airing at the end of 2018, and I’ve heard more than once, 2019 will be the year of personalization. We’ve been talking about getting the message down. Getting your messaging right for your target audience. I now know who my audience is and I need to talk to them in the way that they want to be talked to. Part of that was, “Who cares if you’re using WordPress for this course? That’s not the problem they’re trying to solve. Maybe they even have a predisposition against WordPress. So, don’t tell them you’re using WordPress. Just tell them you’re going to help them launch their podcast in three days. That’s the thing that they want to know.” There was that, then there was the messaging around my identity. I was talking to a guy, Justin Wise, he’s like “What are your problems? What are your big problems? Tell me about yourself.” And I was like, “I make online courses. I was a developer, I taught at the University of Scranton and I was moving, and I wanted to keep teaching.” He goes, “You’re a college professor.” And I’m like, “Yeah.” He’s like, “Does it say that anywhere? In your bio, on your website, anywhere?” And I’m like, “Nope.” He goes, “Why aren’t you telling people that?” I’m like, “I don’t know.” So there was that, and then there’s the question about pricing. I was pricing my courses at between $20-50. Multiple times I was told, “Why are you charging so little? If you charge $300, $400 for a course you’re still charging 10% of what a developer would pay to set up a website for them. You are saving them time, you are saving them money. You’re delivering this amount of value, right?” “Yes.” You’re again going back to the very first lesson I learned in business, that my prices needed to communicate the value that I was providing to the student.

Jeff: I was going to say, I worked at this deli in New York, and I remember distinctly this guy was like “Jeff. You prices.”

Joe: It’s so interesting, because all of the lessons– Have you ever heard of the phenomenon that you say in one room you need to remember something, but then as soon as you walk through the doorway you forget it. This is  apparently a phenomenon that happens where, because you are changing contexts, you forget the things that you were just thinking about. I feel like that happened in business for me. I moved from a client services business to a product business, and then promptly forgot all of the important lessons I learned in the client services business. Like, “Charge the right price. Build the relationship first.” Stuff like that. So it was interesting re-learning those lessons in a much shorter timeframe.

Jeff: I know of the phenomenon of your wife telling you something for years, and then some other business friend of yours mentions the exact same thing  and you listen. Then your wife tells you about how she’s been telling you for years. I know that phenomenon.

Joe: Yes.

Jeff: I’ve had a lot of that happen. My wife is just awesome. She will see something way before me, and for whatever reason, I just don’t hear or act, whatever it is. Then it’s like, four months later and the same people telling me this stuff all the time, and then I’m like “I had this great idea!” And she’s  like, “I told you that idea four months ago.” It’s the best. It’s become a trolling joke at this point. What about otherwise this year, have you had any other what you felt– I don’t want to blow up the Cabo realizations too much, but have you had any other life changing moments or conversations or conferences that you went to that you walked away from and knew, “My business will be better because of this.”

Joe: CaboPress is the one that drives home this fact, because again, Chris curates everything. The audience, the hosts. He knows what people are looking for and what is being taught. But that said, Podcast Movement this year was also insanely valuable for me, because I got to see– I’ve told you this before privately, maybe I’ve said it publicly. People at Podcast Movement were way more interested in the fact that I was a developer than the fact that I was a podcaster. Because everybody at Podcast Movement is a podcaster or an aspiring podcaster, but very few people are web developers and fewer people were WordPress developers. Just getting that perspective of, “I had such a hard time with my website. What would you recommend to fix it?” Somebody said, he is a current coaching client of mine, at the conference he said “I will gladly pay you hourly to show me how to do specific things with my website.” And he is doing that. He followed up on that, and that was monumentally helpful in figuring out exactly who Joe Casabona is in a post-developer life. If that makes sense. That’s weirder than I normally word things, but it makes sense.

Jeff: I heard CaboPress did some good things for you, it sounds like Podcast Movement– You and I attended together and were able to hang out there. That was able to give you some insight. Going back to the target audience, if you want to service the podcast community that would be one really natural way for you to do it and give you some insight there. Do you feel like–? Have you had– What are some other ways that you try to improve or to learn? Conferences are one of them. Is there anything else that is stand-out to you this week? Conversations, books, online courses–?

Joe: I try to consume all of those and don’t consume enough of any of them, except for conversations. I love having conversations. Part of the reason I started this podcast is because I was having conversations and I thought, “This would be good public conversation.” Longtime listeners will know that I’ll say specifically during the interview, “This is for me and hopefully it’s helpful for other people too.” I am learning from my guests while creating this content, and I love that because it’s natural and the audience, the listeners, get to hear my surprise and delight in learning something new in the moment. But this show has been valuable for me in that aspect too, but I try to read a lot. I try to take online courses, I’ve been trying to be better about that because I offer them. So now I  treat it as I’m learning a new skill, but also I’m getting ideas for how to improve my own.

Jeff: 100%. It’s so funny. I’m going to go back to another story of my wife and I, we just went down to South Carolina to visit some family for Thanksgiving. That was right around the time of this recording. What you just said in terms of how you see things and how you watch on one hand, you’re   just watching it however anyone else would. Just for the sheer entertainment value or for the knowledge you’re gaining. But then there’s also this element for me, also being a podcaster and for creating content, and especially I’m really interested in the public speaking side of things. I’ll watch people for not only what they’re saying but how they’re saying it, and how they go about their execution and if they did a good job in that sense. We were both at the hotel laying on the bed, and my wife turned on a video from Vice and they were talking about the living situation in China. There was something about it, within the first few moments of the music they were using I knew, “This is some awesome documentary piece.” I rolled over and quickly started watching with her, and then she knew that I was–  She’s like, “Did you even like it. Did you even like the content, or did you just think it was a cool story?” And I’m like, “Yes. It was both.” Having a handle on both of those things, that’s a cool point.

Joe: Absolutely. Since Podcast Movement, there was good advice there. But then I started listening to some well-known podcasters, and again, longtime listeners will notice that I started introing the episodes instead of just going right into the music and the sponsors. That was something I picked up from Pat Flynn, and advice that was given during one of the talks that both you and I attended. The one where radio people critique podcasters. They said, “You have 30 or 60 seconds to hook a listener–“

Jeff: And you spend like 30 of it with intro music.

Joe: Exactly. There were some real changes that went through the show after Podcast Movement and those conversations, and then listening to podcasts from people that I met at Podcast Movement.

Jeff: That’s great. That’s good. As we start to wind out our time, I’m going to spin back to you the question that you ask everybody else. What is a one trade secret that you have for our listener? And I do not want you to share the same one that you did with the podcasting stuff. Like, specifically for these things you’re doing now, for the goals that you’re shooting for, what is one trade secret you’re comfortable sharing?

Joe: Trade secret…

Jeff: Should have saw this coming, man.

Joe: I know. I definitely should have. That’s also my favorite part of the interview, when people do the whole, “Trade secret…” and really think about it. You’ll have to refresh my memory, I don’t remember what I gave as the trade secret in episode 100.

Jeff: I disagreed with you, to be honest. You said, “Everybody should podcast. You should start a podcast  now. It’s time consuming but it’s not hard.” I was like, “I don’t know about that one,” but–

Joe: I probably should have picked my wording. Because it’s not a learned– Well, it is a learned skill. It’s not a–

Jeff: Starting a podcast isn’t hard. Running a good podcast is incredibly hard.

Joe: That’s exactly right. That’s exactly what it is. So, based on the stuff that we’ve talked about today. The trade secret, the thing that has helped me the most in the last 17 years of business, then starting my own and getting that running start. Build your network. I know that it’s hard to start a conversation sometimes, I think it’s hard to start a conversation sometimes too. I always open with a joke. I make some crack and then we start talking, I start talking to somebody. But that has been hugely helpful. I met Sean and Chris and a group of people at PressNomics because they were smoking cigars and I just walked over and I said, “Mind if I join you?” And then we started talking. Or, the same thing, if you go to an after party at a bar. “Mind if I join you?” You don’t have to drink, you don’t have to smoke. It’s just a way to meet new people and build that network, and provide value for that network. Don’t be a leech. Make it a symbiotic relationship. That’s the most important thing that’s helped me, and that is my trade secret.

Jeff: Cool. I’ll take it. All right, you have been listening to How I Built It. If you want to listen to more episodes about how entrepreneurs built the products and services that they’ve come across, you can listen in at Also, I’ll plug myself a little bit. I’ve been your host. My name is Jeff Large, and if you enjoyed this interview I invite you to come on over to my podcast. I interview a lot of people in the same fashion that I did Joe on this episode, and it’s like you said earlier, the amount of knowledge and things that you’re able to glean from these people is tremendous. The podcast just becomes an avenue to share really amazing conversations.

Outro: Thanks so much to Jeff for doing that. That was a lot of fun. I thoroughly enjoyed having the tables turned a little bit, and getting to tell a bit more of my story. Jeff is an excellent interviewer of course, and it’s always a pleasure to talk to him. In the show notes for this episode I will link to his stuff, his podcast bytes and the interview that I did with him earlier this year so you can go ahead and listen to his story as well. That’s it for this episode, and this year. Thanks so much for making 2018 the best year for the podcast yet, and I will see you in 2019. Until then, get out there and build something.

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