Being A Full-Time Creator And Podcaster And Asking For Help With Joe Casabona

Joe Casabona:

Thanks for having me Jennifer Bourn. I’m very excited to be here.

Jennifer Bourn:

Now, you have been podcasting for nine years — which I didn’t even know podcasting was a thing for nine years. You have courses and mentorship, all kinds of offerings, live streams, and things to help content creators do better work and create better content. You have three kids under the age of five, volunteer at your daughter’s school, and you’re often juggling work as a full-time dad along with everything else because your wife is a full-time ICU nurse.

I’m going to need some more details here. So first, I want to know what your path looked like going from client services to full-time content creator. What did that transition and journey look like?

Joe Casabona:

Yeah. I knew when my daughter was born, basically that I didn’t want my income tied to the number of hours I worked. So, we’re talking like March 2017. I decided I need to figure out a way to get out of explicit client work, which I know like if you do client work the right way, that’s not necessarily tied to hours either, but for all intents and purposes, it usually is.

I wanted to move into like products or subscriptions — something like that. So, I had a, uh, it was like kind of a bad plan, but I had a plan in place to sell more courses and to get more podcast sponsorships because I had launched my podcast about six months before my daughter was born.

My main podcast is doing the best. I had a previous one in 2012 that was not very good. So, I looked at: How can I create more recurring revenue? How can I sell more products? And then I left my full-time job in June of that year. So, I had a three-month-old at home and I thought, all right, well, now it’s sink or swim.

I need to make money or find another full-time job and so it was a long road. I think, uh, a conference that we both love CaboPress really helped with that because I learned at CaboPress that I really need to learn more about my audience before I offer a product to them.

I need to create more content to build my audience and create offerings for them. And here’s the better way to price subscription services and there’s the whole, productized service where you can spend fewer hours and do more high-impact stuff.

And so, it’s been a big learning experience, but now I feel like I have a good process in place. I have a very clear mission for what I want to do with all this content I create and how I can convert that just from time from content into like dollars to support my family.

Jennifer Bourn:

Content into dollars is the key here, right? There are a lot of people that create a lot of content that doesn’t ever convert over into dollars. What was the aha moment for you where you realized I’ve got to start doing something different and what was the first step you took to start monetizing the content you were creating?

Joe Casabona:

The thing that I knew I had to do differently was explicitly asking for money. This is something I hate doing. I’m a proud Italian New Yorker — New York, Italian — I’m like, if people want to give me money, they’ll give me money. But that’s generally not the case with sponsorship unless you are a huge content creator. That was definitely not the case in 2016. It is more the case today.

More brands are seeing the value in partnering with content creators or influencers as many of them are called. And so, the first time I got sponsored — my first episode of How I Built It — was sponsored and it’s because somebody reached out, they wanted a backlink and I said, look, I don’t really do backlinks, but for 99 bucks, I’ll promote this thing on my podcast and he was like, yeah, sure and it was that easy.

Then for the second episode, I spoke to our mutual friend, Rebecca Gill, she mentioned LearnDash and she encouraged me to reach out to Justin Ferriman and see if he wants to sponsor that episode because it was a good synergy. So, I did that and then I was like, dang.

So, I just started reaching out to my network after that. And so I think the important thing to have in place is a good network of people who trust the work you do. Because after that, I reached out to Nexcess and Liquid Web, and other hosting companies. Because I knew that in the WordPress space, they had deep pockets. So, they supported my work and so now I have a pretty well-oiled machine for getting sponsors.

Jennifer Bourn:

Well, I think it’s important that you didn’t just assume people in your network would say, no. There’s kind of this little bit of imposter syndrome that many of us have that we think they’re not going to say yes to this.

Joe Casabona:

Yeah.

Jennifer Bourn:

And so then you don’t even ask. So being able to reach out to that network and having the confidence to say, this is what I’m doing, do you want to be a part of it? That takes some bravery, right there.

Joe Casabona:

Yeah. And you know, this is the thing that my friends always told me when I was afraid to ask a girl out: What’s the worst thing she’ll say? No? And I’m like saying no is a demoralizing thing! But as I got older, I realized that no, it could be no for a bunch of reasons.

Jennifer Bourn:

And then you’re no worse off. You’re just where you started.

Joe Casabona:

Exactly. And the way I thought about it is I made a list of companies. because my podcast was WordPress-centric at first, I’m like what companies are sponsoring WordCamp US for five figures at least.

Jennifer Bourn:

Yeah.

Joe Casabona:

You’re sponsoring this one event that’s two days for five figures. I’m asking you for four figures for months and forever links on a website. And they’re like, well, yeah. Well, one the value prop is that it’s kind of hard to say no to it.

Jennifer Bourn:

That’s pro-level price anchoring.

So before we get any further, I want to go back and I want to hear a little bit about your family and work life. As entrepreneurs, as freelancers, we try to keep these things as separate as we can but let’s face it, it’s all a big mix mash. Like it’s all mixed up and it’s all blended together, especially when you’re a parent and you’re working at home full-time and your kids are home full-time.

I never sent my kids to daycare. I know your kids are with you as well. What does that look like? And how do you still get stuff done?

Joe Casabona:

It’s really hard. Thankfully, my, so my oldest is in school now.

Jennifer Bourn:

That’s a game-changer.

Joe Casabona:

That is a game-changer. My middle, my son, we do send him to daycare because after two years of the pandemic, we felt like he should get other interaction besides just us. And you can tell he flourished a lot since being there and getting that interaction. He said Yankees yesterday. I’m such a proud daddy.

Jennifer Bourn:

Oh, that makes Joe’s heart happy.

Joe Casabona:

Yes, yes, it does. Now. I need to get them to boo the… I don’t want to alienate anybody, but I’m going to get them to boo the Red Socks. And so right now, it’s just my youngest daughter, who’s four months old as we record this at home, and thankfully she took like a three-and-a-half-hour nap yesterday.

Jennifer Bourn:

Oh, that’s glorious.

Joe Casabona:

And, and the game you play here is you don’t expect that going into the day but when they do nap, act like they will. Right? Because otherwise, you’re like, well, I’m not going to start anything important because they’re not going to nap long. And then an hour in you’re like well, I could have gotten a bunch of things done now.

So, I don’t assume at the beginning of the day that she’s going to nap really well for me but when she goes down, I need to take advantage of that time.

Jennifer Bourn:

I love that. Just seizing the moment and maximizing it.

Joe Casabona:

Yes, and another important part of that is I try to wake up at like 5:00 or 5:30, hopefully before all of the children wake up. I make a cup of coffee and then I sit down with my planner, and I have the analog card system, so I’ll write down the things I want to get done on a card and that stays in my back pocket.

And my laptop is upstairs, and my desktop is downstairs and so when Abby goes down, I go, okay, here’s the first thing on the list. This is what I’m going to work on. I can do that up here if I need to, or I can, I’ll go downstairs if it’s like deeper work. So, I have the plan — as soon as she’s down, I know reasonably that she’s going to be… I’m not going to have to go up in like five minutes or whatever.

Jennifer Bourn:

Right. So, you have your main office, your main desk is downstairs, and then you’ve got your laptop. It sounds like you have a similar approach to work that I do. I have my office where, when I need to do some serious stuff, I am in here. But when I am doing more creative work, or writing, or things where I don’t need the giant monitor and all the fancy stuff, then I’m on my laptop and I can go wherever I need to go and work wherever I need to work.

Do you find that allows you to fit in — when some of those gaps in the schedule happen or some of those moments where your kids are really well occupied — and get something done that helps knock some of those to-do lists off during your day?

Joe Casabona:

Yeah, absolutely, especially again, because my daughter, Abby, loves the mat with like the dangly things, and she, I think more than any of my other children, just can lay there for like an hour just like staring and kicking. And so that laptop is like always at the ready.

On one side of our dining room table when we’re not eating, it’s the casita — the Lego version of casita from Encanto, which my oldest bought with her money that she earned from me swearing a lot, and on the other side is my laptop with a notebook open, just ready to go when LouLou is usually climbing on something and Theresa has her iPad and Abby’s on the mat and I’m like, perfect. I’ll do this now.

Jennifer Bourn:

That’s so great. I could not have existed when my kids were really little and I was working at home, without my laptop. We would move from room to room in the house, and I had different toys in each room. One was all the play food and the kitchen and the house stuff. And one was blocks and building stuff.

So, we would just rotate around and I’d bring my laptop with me and sit in there with them and we’d engage and interact, but work. Finding those little moments where they’re fully engrossed in an activity to sneak something in, sometimes that’s just what you got to do.

Joe Casabona:

Yeah, absolutely. When Abby’s taking her afternoon nap and both kids are home from school, I downloaded an app called Hue Sync and this app will pipe into your speakers and then blink the lights with the music.

And so, if I really want to get work done, and Abby is sleeping, I go, Hey kids, you want to have a dance party?” And we’ll go downstairs and I’ll put on like Kid Bopz or whatever, and the music will flash the lights and they’ll just like run around in circles, and I’m here doing stuff on my computer. And like, they’re happy. I’m happy.

Jennifer Bourn:

That’s awesome. It’s a dance party in dad’s office.

Joe Casabona:

Which, I’ve earned the label coolest dad, my daughter: you are the coolest dad. Yes.

Jennifer Bourn:

Love it. Those are like such good moments. Sometimes we don’t feel like the cool parent.

Joe Casabona:

Oh man. I, most of the time I feel like I scold more than I don’t, but I know that’s just like the feeling.

Jennifer Bourn:

It is. Doing the hard job as the mom and the dad. As I understand it though, some days are more challenging than others. We set up our lives to support our best lives, but sometimes it just doesn’t work. And I know you shared some of that all came to a head in the middle of the pandemic.

Can you tell me what happened? What went down for you?

Joe Casabona:

Yeah. So, I’ll say earlier, I said, don’t expect that you’ll get the best-case scenario for naps, but it’s hard not to wish for that. In the height of the pandemic — let me tell you something about my wife and me — uh, we are apparently very good Catholics and we decided to bookend the pandemic with babies.

So, the day I got home from the last in-person WordCamp US, I woke up to my daughter slapping me in the face with a positive pregnancy test, which is just a great way to wake up when you took the red-eye.

Jennifer Bourn:

Oh my gosh.

Joe Casabona:

So, in November 2019 we find out we were pregnant with our second — we had been trying and Lou was born in July of 2020. So now we’re locked down. My wife is not working from home — she’s an ICU nurse. She is busier than ever.

We are a little bit fortunate that she was pregnant during the most unsure time of the pandemic. Because she was pregnant, she got no COVID patients and then she was on leave for the summer for that first summer spike. So we’re like a little bit lucky there. But yeah, when she went back to work, Theresa’s she wasn’t in school yet and it was so close. So at least I wasn’t doing virtual school. Like in hindsight, it’s easy to be thankful for stuff.

But it was really hard for me to manage because I was busier than ever, I was freaking out about money, and I’m trying to manage two kids, and Lou did not sleep as well as Abby does now. And there was one day where I — I don’t think I’ve ever had a real honest to goodness panic attack — but this was the closest.

So, it was like December and I just like, started shaking and I sat down. I’m going to get a little emotional. It’s fine. It’s fine. I’m Italian. I just like started rocking a little bit and my daughter — three years old at the time — brings me a towel and a water bottle and tells me it’s going to be okay. And I’m like, that’s not okay.

My daughter, at three, shouldn’t have to take care of me. So, I like signed up for Better Help the next day and I had my first session, like right before Christmas and we went until May or June of 2021. And in May of 2021, I found out two things that I thought, well, it’s great that therapy is ending now.

We found out about Abby, which was an unexpected pregnancy, and I also found out I had type two diabetes.

Jennifer Bourn:

Oh my God.

Joe Casabona:

It’s all coming together but shout-out to my therapist, Erica, she like specialized in toddler play and she helped me work through it. Just like having somebody… The first time I was like, “What do I say? So, are you going to ask me like how am I feeling or whatever and just like, talk about whatever you want to talk about?” She’s like, this is your time. And I was like, I don’t know if I’m going to have an hour’s worth of stuff.

I had an hour’s worth of stuff, obviously. And so, she gave me really good advice. I took really good notes, obviously, because I always take good notes. And it really helped. It helped me and my wife. So, she taught me kind of how to cope.

She taught me like, uh, there’s a scene from, she didn’t say it like this, but I relate everything back to the social, to pop culture. There is a meme — an episode of 30 Rock where Jack Donaghy is like trying not to get emotional and he’s just like crush it, crush it with your mind vice — and so now if I’m like getting like upset or something, I say, “Crush it with your mind vice,” which is not to ignore the feelings, but to cope with them in a better way.

Jennifer Bourn:

I think it’s really powerful that one, you’re able to share what you went through because they’re a lot of people that can relate to that pressure of when things all just feel like a lot. And sometimes we have those moments in front of our kids — and we’re only human, right. We can’t control when those things come on and when those things happen… but also that you thought right away, I need to talk to somebody.

There are a lot of people that struggle for a long time and don’t get the help that they need. But you reached out to Better Help, found a good fit, and stuck with that because that’s what you’d recognize. How did you decide that was your best next step?

Joe Casabona:

Yeah. I mean, I was very like, men don’t need therapy. Men don’t do this. Men don’t do that. But then like, you know, I have a family and the thing that replaced men don’t do this, men don’t do that, is men do and women, but I’m a man — men do what is best for their family.

The fact that I couldn’t effectively, or I felt I was on a road to being unable to effectively, take care of my family, my children, that’s when I’m like, well, I need to do what a man would do and get help to effectively take care of my children. And it was really like — I mean, geez, my daughter showed what I feel is like an astronomical amount of empathy at three years old.

The fact that she did that helped. Because I was like, she should never feel like she has to take care of me, not at this age, maybe when I’m 70. Right? And she’s like, alright dad come on you’re walking into the street, come on. Better Help. I mean, speaking of podcast ads, they were everywhere for a while.

So, I was like, let me check it out. I did speak to my primary care doctor, and I was like do you guys cover therapy? And they’re like, well, it’s kind of a wash depending on if you need and what you need it for or whatever. I have good insurance, but this was way more convenient and like about the same as what I’d pay.

So, I did Better Help.

Again, they hooked me up with somebody who they’re like, there’s a questionnaire. What are you struggling with? What do you need most help with? And then they paired me with somebody who was just great.

Jennifer Bourn:

I love that you took action, not only for your own betterment and mental health, and to be able to show up as your best self, but also from the lens of wanting to show up better for those around you.

I have had those moments where I was crying and Natalie is her little toddler-self patting me on the face as I lay on the couch crying, she’s like it’s going to be. Okay, mommy. Those are some sobering moments where you realize I’ve got to change what I’m doing here.

So, the fact that you could recognize that and say, I realize I’m going down a road that might not be the best for myself or my family — and then be willing to do something about it and create that change for your family is really a testament to the commitment that you have to the people that you love and showing up as your best self. Because when things aren’t right at home, they trickle into our work. They affect everything. The ripple effects of those things are pretty phenomenal.

Joe Casabona:

Yeah, absolutely. And I mean, at this point I gotta give a shout out to my parents and my family. I’m not a guy who likes tattoos, but two of the four of us have a tattoo that says, I wish I could remember the Italian, but it says family comes first in Italian — so like Famiglia prima, something like that.

It’s something that was taught by my parents to us. My dad would leave our house at 5:30 in the morning to get work at 7:00 am so that he could be home by 4:00 or 4:30 so that he could attend all of our extracurricular activities.

Jennifer Bourn:

I love that. You do what you gotta do to show up for the people that you love — the people that you value.

Joe Casabona:

Yeah, exactly. So, that’s something I really internalized, you know, my family, this is why I started my business to be there for my family so that I have, I have a brood of children Now, and I want to be there for them.

Jennifer Bourn:

Now, you started your business for your family. You left a full-time job, went into self-employment, took that leap, and thought it was going to be maybe a little bit different than it ended up being. That road wasn’t quite as smooth as you hoped. How did that transition go? And what did you do to even some of that out and help get on that right path that you needed?

Joe Casabona:

So, when I left my full-time job, it was at a time when many agencies in the WordPress space were struggling a little bit. There was like a lull in the WordPress agency space and so our agency, like many agencies, was having some trouble with payroll and I had a side gig, and I was full of hubris. I don’t need this job. I’m helping. I am making enough money to support us, even though we’re missing payroll. Except that calculus was off because we still got those paychecks.

When I left, I thought I was making enough money from what I was already doing to support the family, when really, that side gig money was just gravy on top of full-time money.

So again, I tapped the network I had. Our friend, Shawn Hesketh, for example, needed some video work done and he really helped me at that point. And I lined up a bunch of sponsors. I just kept doing client work as I needed, but I tapped my network of people to be like, Hey, I’m out on my own. I have some availability now.

And that floated me until I actually got my head right. Which is like, you know, a little bit into the next year of, okay. Now I’m creating a predictable business model.

Jennifer Bourn:

I love reaching out to the people that you know, and saying, “Hey, do you have any work?” You were proactive about going after what you needed to create the business that you wanted and didn’t just sit back and wait — “Woe is me. I hope somebody hires me.” I think there are a lot of people that start freelancing and think the clients are just magically going to show up.

And in reality, we’ve got to go out and get that work. We’ve got to ask for the work and say, “Do you know anybody that’s hiring? Do you need anybody? Do you work with freelancers? Do you outsource things? Can I get on that list?” and you took that bull by the horns, so to speak, and went out and got that.

But you also realized you can’t be a one-man show. We can’t do everything, and I’ve gotten some help over the years. What kind of help do you have in your business now?

Joe Casabona:

I Just want to reinforce one point really quick, and that is that I had this network already and I provided value to these people. Right. I wasn’t just tapping them for work. I think that’s probably if you take one thing away from this conversation, it’s the importance of building a good network of relationships with people because that’s what has helped me the most. And that’s, long-term too — I just had my best month income-wise and I didn’t do any outreach for it. It was just people who had a budget for creators.

They had known me in the space for a long time and they’re like, we want to support creators like you. It’s a little bit of a long game, but it pays really good dividends.

So anyway… In the pandemic, when I knew I was dropping down to part-time, I thought, well, I need to find some people to help keep the wheels on this thing. Uh, and so one of my earliest hires even pre-pandemic was a podcast editor.

I realized that editing was my least favorite part of podcasting and then he did it for just like something that seemed impossibly low to me because it’s something that took me like a solid two hours, but I’m sure it doesn’t take him nearly that long.

And so, yeah, he’s still my editor and we have a good process in place between the automation I have set up in the emails he gets and things like that. And he edits all of my podcasts except for one, which I just record into Descript and release. Then, I also hired a video editor because much like podcast editing, video editing is the longest part of the process.

So, if I can make the content and send that off to somebody, I can do something else in the meantime. Now he actually edits my own courses, my YouTube videos, and any client video work, you know, sometimes client video work will come like courses for hire sort of thing.

Then, I finally hired, oh a transcriber, and a VA. I just gave her a raise. She’s in the Philippines and I feel guilty about the amount I pay her versus the amount of value she provides for me. Generally, a VA in the Philippines require a little bit more handholding in the beginning, and that’s why they’re generally lower than hiring a US-based assistant or whatever. There are cultural and language barriers. And so, what I’ve been doing is recording videos, having her transcribe them, and then write out the steps.

And we have a handbook now. And so, I gave her a 50% raise, which is, really good for her. And also, helps alleviate some of the guilt I have because she is basically publishing all of my content for me — all of my How I Built It episodes she publishes. Usually, the WP Review episodes are a little more timely, so I’ll do those, but then she’ll go in and transcribe them.

She gathers the show notes for these things, which I’ll generally check because they’re like really vague notes. And I just assigned a couple of maybe bigger tasks to her. One is using Descript to create videos out of WP Review to go to YouTube because YouTube has announced that they want to be in on podcasting more. So, if your podcast isn’t on YouTube, get it on YouTube.

She has been instrumental in helping me with a lot of things. Basically, once I record an episode of my podcast, I don’t really touch it anymore. She creates the graphics, my editor edits them, my transcriber transcribes them, and then she uploads them.

Jennifer Bourn:

That’s amazing. So, I know people are wondering, because this is a hard thing for everybody, How did you find the right people? What did that process look like?

Joe Casabona:

My video editor was the easiest one. He came through a referral. A friend of mine, a woman named Brittany Blues, an editor at Treehouse — a bunch of them got laid off and she came recommended to me and she couldn’t take me on. So, she recommended a colleague of hers. And so, I was like, yep. You edit for Treehouse. So, I give him pretty minimal instructions and he just goes and cleans it up. The podcast editor: I went through a couple before landing on Joel. But I found all of them on Fiverr.

He’s been with me for years at this point. And then the VA was the hardest one because I didn’t really know what I was doing.

Jennifer Bourn:

Virtual Assistants — finding the right one and a good fit… It is so hard.

Joe Casabona:

And you know, it’s about managing expectations. My first few tasks for my VA were kind of nebulous — do research, find things — and those are not good tasks for the type of VA I hired. There’s a website where you can find VAs in the Philippines and I put out a job posting and I got like 800 responses. And Honor’s stood out because the first line was like, dear Joe, I hope you hire me so that my mom could stop asking me what I do for a living.

Jennifer Bourn:

Oh, my gosh!

Joe Casabona:

I picked the top five and then I did like a test assignment with them, and Honor did hers pretty well, and then there were a few in the middle. I had a VA specialist basically on my podcast and I was like, so how do I do this? And he gave me the advice to record the video and stuff like that. And since then, it’s been really smooth sailing.

I check in with her every six months. I’m like, “How’s it going? Can I do anything for you?” Which she really appreciates. I don’t know if that’s an uncommon thing. I want to make sure she’s happy because she saves me dozens of hours a week.

Jennifer Bourn:

That’s so fantastic. So, you’ve been podcasting for nine years. There are a lot of people that start a podcast and barely last past what — 6, 8, 10 episodes?

Joe Casabona:

Yeah. A 75%. Don’t make it to eight episodes.

Jennifer Bourn:

75%.

Joe Casabona:

Yeah.

Jennifer Bourn:

Wow. Okay. I’m recording my very first few. I’m just getting started. Nine years in, what’s the secret to sticking with it so long?

Joe Casabona:

Back to your content. I think That’s the most important thing. like I just said, right? Once I’m done recording, I don’t touch it and that’s because I’m not recording the day before I need to publish. I now have interviews, um, ready to go until June because I have two days where I record — today happens to be one of them.

Once I record, I write up the summary and the top takeaways, right after, like, I get a text message, it’s like do the post-interview summary. And then I put it all in a folder. I ship it off to my editor. I have Air Table managing who’s the sponsors. He knows which ones to put in. He knows how to make it members only ready. If there are any edit points, I point them out. If I really want a good episode, he does like this advanced editing and I’m like, do the advanced editing for this one.

But yeah, once I drop a folder in the Needs Editing Dropbox folder, he gets an email. Then he uploads it to the Needs Transcribing folder and my transcriber gets an email. And then when it’s back in the fully edited folder, AirTable, automatically updates. And my VA gets an email telling her to add it to WordPress.

Jennifer Bourn:

That’s some serious, serious automation right there.

Joe Casabona:

Yes. It all stems from the first thing I said: batch your content. Before you launch a podcast is the best time to do it. You can record 10 episodes. If you release weekly, that’s two and a half months. Here’s the second thing: it doesn’t need to be weekly. You hear podcasts, you think weekly. Some of the best podcasts I know that I listen to are monthly.

So, it’s just about providing value and managing expectations. When I first launched How I Built It, I was like, I think it’s going to be fortnightly. And then I had like 20 or 25 interviews — like everybody said yes to interviewing and I was flummoxed. Chris Coyer said yes.

People who definitely didn’t need to say yes — they didn’t need my non-existent podcast to promote their stuff. But they were just generous with their time. You were one of my early guests, And so everybody I asked said yes and I was like, all right, maybe I’ll do like three out of four weeks. And then I moved it to weekly because I just had the back catalog but get the back catalog first.

Jennifer Bourn:

That is such a great tip because too, there are going to be unexpected things that show up. There are going to be times you’re on vacation. There are going to be times you get sick. Having that backlog ensures consistency. Even if the proverbial poo hits the fan.

Joe Casabona:

Yeah. And let me tell you it happens. I’ve been doing this for nine years. I have a really good process in place. It still happened to me because I reserve like one in six episodes, maybe for something more timely. That’s just me. It’s like a 15-minute episode. This helps you really establish authority with your audience.

And I got sick for like two weeks. And so if you find the last solo episode, I sound terrible, and it’s because I didn’t have it. Right. It’s the only episode in like a two-month span that I didn’t have ready to go.

After that I was like, I need timely episodes and I also need like some canned solo episodes. So, then I recorded a couple that are less timely but still solo tips how to make money podcasting, or whatever.

But yeah. The process kind of fell down because a lot of things happened in the last couple of months, you know, my wife went to work and we had a death in the family, and then like, just a lot of stuff happened. It’s fine if you miss a week. I still got it done. It was late, but you know what? Life happens sometimes. That’s the other thing.

Jennifer Bourn:

I say embrace imperfection. It is what it is. Sometimes something’s got to give and you just give yourself grace.

Joe Casabona:

Yeah, exactly.

Jennifer Bourn:

So, in addition to your podcast, you have the Creator Crew, which is a membership program, and people in Creator Crew get access to your courses, behind-the-scenes insights on how you create, workshops, extra episodes of your podcast How I Built It. Where did the idea come from?

Joe Casabona:

So, my first kind of online course website was called WP in one month. Terrible name for a lot of reasons. First of all, I locked myself into WordPress. Second of all, I tied myself to some weird one-month timeframe. So, I knew I needed to change the name. I didn’t want to be tied to WordPress.

So I picked creator courses, which I was very proud of. I love that name. And then I had a bunch of courses that I sold a-la-carte and I also had the membership. Then I interviewed John Warrillow. He wrote Built To Sell, and he convinced me through the course of the interview, that maybe I should get rid of a-la-carte courses.

So, for Black Friday, I said last time you can get a-la-carte courses. Also, you can get a pretty steep discount on the membership. Guess what happened? No one bought the a-la-carte courses. It was only membership. So, I was like, perfect! At the same time, I knew I wanted to launch a membership for my podcast that gave people ad-free extended episodes. So, I had two memberships going.

This was a bad idea for a lot of reasons. I was managing two different infrastructures. There were people who wanted access to both and now they were maintaining two different accounts. I’m using Circle for the community. And so that allowed a single sign-on through WordPress with CreatorCourses.com, but now with How I Built It.

So, I was like, you know what, it’s all going into one membership called the Creator Crew. And it’s Lite and Pro where Lite I have billed it as if you just need inspiration. If you just need a little idea generation sign up for Creator Crew Lite. It’s $50 bucks a year, you get ad-free extended episodes of this podcast plus live stream archives. That is less than $5 a month. And I kid you not, I just paid $7 for a latte, like a single that I didn’t even finish. Could’ve gotten two months almost to the Creator Crew. Yeah.

And then for Pro, you get access to all of the courses, as well as workshops. These are planned workshops. I don’t like talking about things I’m planning, but I’m basically playing that by ear with what my members want to learn.

But right now, you get access to all of the courses for launching a podcast and monetizing a podcast. That’ll also give you a discount on any future products, like a cohort-based course or anything like that. So, you know, at first, I thought the paid workshops were going to be open to the public and I would charge like $50 bucks for a paid workshop.

I don’t think my audience is that big or primed yet. So instead, I’ll do free webinars for the public and the members will get access to the replays and then workshops for the memberships. And I’d like to do those quarterly, but don’t hold me to that.

Jennifer Bourn:

I like the premise of a free workshop for the public but members get the replay — a benefit for the members in your program.

Your membership is such a steal because the value in there is so amazing. It’s kind of similar… I’ve been moving some of my Content Camp things around and changing the way I do it. Individual Content Camps: $297 for a three-day workshop, or you can do all three of them for $600 bucks. It’s like getting a whole content camp for free.

No one buys the individual events. Every single person that has bought Content Camp this year has bought the three-pack bundle because it’s such a deal. And then with Content Creators Club, my every other week live copyediting and content strategy consulting, they all get Content Camp included. That makes such a huge difference to reward those loyal members of your community.

The people that are in Creator Crew that get those workshops and get that replay and get access to all of those things. They’re more invested. Do you find those people end up seeing better results?

Joe Casabona:

Yeah, absolutely. And, you know, they are also more involved and more visible in the community. They take advantage of my office hours, which are only available to members. And I’ve had a couple of my members book, some office hours with me and then get their first podcast sponsor as a result of it.

So, it’s really great. So, with the webinars, make the replay available for 24 hours for people who are sleeping when it actually happens. But the webinar replay for members only is what I like to call a low effort, high reward for members.

It’s content I’ve already made that now is there so it’s high value for them and I didn’t have to do anything extra to give that to them. So, it’s a win-win.

Jennifer Bourn:

That’s so amazing. So, I’ve got a few questions for you. First, what other can’t live without tool or trick have you discovered that you cannot live without?

Joe Casabona:

I’m gonna say a tool that has a lot of tricks on it, which is my Stream Deck. I’m a huge fan of my Stream Deck. You can find it on the homepage at Casabona.org — it’s one of my popular posts. But my Stream Deck gives me shortcuts for a bunch of things.

I press a button and my podcast workspace is set up where Riverside opens up on one side, Garage Band, and then my show notes. Do not disturb mode automatically goes on for my recording, the light turns on upstairs — one push of a button.

I have another one that is just a pencil and I press it and it runs my, “I have an idea” Apple shortcut so I can just quickly log something. Time trackers. Air Table bases. Before we started recording, I pressed the button on my Stream Deck and my lights turned purple because that’s like, on-brand for me.

The Stream Deck saves me so much time. It’s like a physical manifestation of Text Expander, which is another thing I love.

Jennifer Bourn:

One click of a button and everything’s set up for exactly the job you need to do. That’s pretty phenomenal.

Joe Casabona:

Yeah, absolutely. I’m workshopping an idea. Keyword research tells me this might not do too well, but if I search for the right things… It will be called Stream Deck Academy on YouTube.

Jennifer Bourn:

I would take that. I have one and I haven’t set it up. I think I need to hire Joe to fly to my house. So, what do you do to ensure that you stay in a positive headspace and have a great day?

Joe Casabona:

Ooh, that’s a really good question. I think it’s something I don’t do, uh, that I need to be better at and what I need to not do. And this is advice that Erica gave to me over a year ago, or maybe two years ago now…

I can’t wake up expecting that I’ll get anything done before I go to work. When I do that, it sets me up for failure because my daughter is a baby and she’s going to wake up when she’s hungry and I can’t really fault her because two nights ago she slept for nine hours straight.

Jennifer Bourn:

Oh my gosh!

Joe Casabona:

Yeah, she’s like look, I know I’m the youngest, I’m just going to vie for favorite child.

So, this morning I woke up at 5:30 am. I was like, I’m going to wake up early, I’m going to go to my office, and I’m going to have quiet time. And Abby slept from around 6:45 pm to like 1:00 am really good, and then 1:30 to 6:00 am and you can’t get mad at that, but I was mad at that.

When Erin brought her down this morning, I was like, ah, but as I’m feeding her — she’s lucky she’s very cute because then you put me back in a good mood. The thing, um, that I need to do for me at this point is not have a super high expectation because my schedule in the morning is not mine.

The thing I do to put myself in a good mood in the afternoon, especially now it’s getting nice out, is I’ll go for a walk and I’ll smoke a cigar. Going on a walk gets me out of the house. I’ve got my AirPods in noise canceling, um I can think about whatever or nothing, and then I’ll usually sit in the backyard and finish it — and my kids generally will not come near me, they know not to come near me when I’m smoking. If they do, I put the cigar out, I’m not smoking in front of my kids. That’s very important to me.

Then, I’m like energized from like four to six and I get good work done at that time.

Jennifer Bourn:

Oh, that’s awesome.

One last piece of advice you have for people who are creating content and may be stuck. Maybe in a little bit of a funk. Maybe trying to find that inspiration. What would you say?

Joe Casabona:

Look for stories everywhere. Some of my favorite pieces of content came from me taking my kids to Rita’s. The first time I had a, I’ll say a high school-aged girl, um, I had two kids in tow, Lou wasn’t walking yet so I was carrying him. Rita’s is situated in the middle of a parking lot. I ordered three Italian Ices — people around here call it Water Ice — that’s incorrect. She handed them to me all separately. No lids. And I was like, I’ve got children in my hands.

The next week I went, and it was a woman who was my age, maybe a little bit older, definitely had kids because I ordered three Italian Ices again and they came in a secured bag with lids. So, it was as easy as possible for me to carry. So, I took that experience, and I wrote understanding your customers is how you sell more products. And I told that story: one didn’t understand my plight, one definitely did. And that left a good feeling with me.

Uh, the same thing: we had two plumbers come in one day or in one week. One guy said to my wife with two kids screaming, “Well, you can go to Home Depot and get a new faucet and I’ll install it. I’ll just wait here.” And I’m like, so you’re going to hang out in our house while my wife takes two kids to a Home Depot. The other guy who came was like, “Yeah, I’ve got three different faucets. Pick out your favorite I’ll install it here. We’ll be done in a half-hour.” Guess which one we went with.

Jennifer Bourn:

I think I can guess.

Joe Casabona:

Yeah. I wrote about being prepared and again, understanding your customer’s needs. So, look for those stories in your own life experiences and tie them back to things you’re working on. That’s advice that Don Hahn gave me.

Jennifer Bourn:

Well, it’s such great advice because stories are so powerful. That’s how you connect with people and that’s really the thing that grabs their attention.

Joe Casabona:

Right. I’m sure there are people who read that they’re like, “Yeah. I totally get trying to make dinner for kids, and then a guy giving you something to do, even though you’re trying to hire him to do the thing.” So, like, yeah. It definitely connects with people.

Jennifer Bourn:

That’s so good. I think that’s a fantastic note to end on Joe. Where can people connect with you online if they need more Joe in their lives?

Joe Casabona:

You can find me over at Casabona.org. That’s the path that will take you wherever you want to find my podcast or my Crew, the blog posts I mentioned — it’s all going to be on the newly redesigned Casabona.org.

Jennifer Bourn:

Thanks for joining me and for sharing your journey of seeking satisfaction, Joe, this was a pleasure. There are so many gold nuggets here that I know I’m going to go back and re-listen to. this as well. And I know that many folks are going to do the same.

Joe Casabona:

Thanks so much. This was great.

Jennifer Bourn:

If you enjoyed this episode of seeking satisfaction, subscribe for new show updates at Jenniferbourn.com/seeking-satisfaction/ and please leave a review on your favorite podcasting platform.

If you would like to hear more from Joe, and not only learn his CALM Framework for being a content creator but also get some tips on using Zapier for automation, check out the Seeking Satisfaction, Extra Minutes Membership.

Members receive extra minutes from podcast guests like Joe that provide valuable training to do business better. You can find the details about the Extra Minutes Membership and Joe’s bonus training in the show notes.

Until next time, may you live inspired, embrace imperfection, seek satisfaction, and have a fabulous day.

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