Joe Casabona, Podcast Liftoff

[00:00:55] Sanjay Parekh: Joe Casabona started his career almost 20 years ago as a freelance web developer. As time went on, Joe realized his true passion: helping people grow their podcasts into five-figure businesses. He started Podcast Liftoff in 2017 and has since been helping his clients transform their podcast from a hobby to a revenue-generating machine. Today, I’ll talk with Joe about how he started his business, how he sets boundaries between his work life and personal life, and some of his recommendations for tools and systems that he uses at Podcast Liftoff. 

So, Joe we’re talking about your podcast business on a podcast — pretty meta. I feel like I’m in Inception. Welcome to the show!

[00:01:37] Joe Casabona: Sanjay, thanks so much for having me. I'm really excited to talk about this, and this is like where I'm all the time, right? Like I have a podcast called The Profitable Podcaster, the Profitable Podcaster Podcast, where we talk about profitable podcasts.

[00:01:51] Sanjay Parekh: That's quite a tongue twister, I must say. But, before we get to the Profitable Podcast, that you're going to do or have done many times, tell us a little bit about your background. Give us a couple minutes on kind of you and where you came from and how you got to where you are now.

[00:02:07] Joe Casabona: Yeah, I tell people that the way I got here, because I have my master's in software engineering. Some of the first things that people say to me is, you're so personable, how are you also like a software guy? And it's because of this: I got into web development at 14 when my church was like Joe, we need a website. You’re good with computers, can you help us? And I was like, no. And they're like, we'll pay you. And I'm like, yes. So, I was doing websites. I loved it. It let me work my technical and creative brain, like my science brain, my art brain.

At the same time, I had been doing drama club since like second grade. So, I loved entertaining, I loved being in front of people. That transitioned as I got older — because you don't really do school plays like when you're out of college — into public speaking and teaching. I got to teach in the classroom for my alma mater at the University of Scranton. And when I got married in 2016, my wife got a job away from Scranton and so we moved downstate, and I wasn't teaching in the classroom anymore. And so I decided, you know what? I'm going to do two things. I'm going to create online courses because I love teaching and I'm going to start this podcast so I can get to talk to people. Because as a self-employed, or a remote worker, at the time, I wasn't self-employed. As a remote worker, I don't get to see a lot of people. I'm moving farther and farther away from where I live and my friends and my family. And so, this allows me to entertain and be the extroverted entertainer that I am. And in 2017, about three months after my daughter was born, I decided to leave my full-time job and start a business for real, with no safety net or school or my parents' insurance or anything like that. And so that's the nutshell of how I got from dude making websites to professional podcaster.

[00:04:03] Sanjay Parekh: So, would you consider young dude making websites your first entrepreneurial venture, or did you have something before then?

[00:04:13] Joe Casabona: It's funny you asked that because I would always describe myself as a less handsome Zack Morris. I was always trying to figure out ways to make money. I would try to turn a profit at our yard sales. And the first thing. It's probably long enough that I could talk about this. The first thing I did to make money was, aside from fixing people's computers, was make mix CDs for my schoolmates. I was one of the first people in the school with both a cable modem and a CD burner. And so, they would give me a list of songs. We had a, oh, this was even before we had a cable modem. We had a separate line though, a separate phone line. So, I would leave the computer on all night using one of those apps that you're not allowed to use to download music.

[00:05:02] Sanjay Parekh: I had a feeling we were going to get into an admission of wrongdoing, but we're going to skip over that.

[00:05:09] Joe Casabona: This was all education, this was all educational use, is what it was.

[00:05:13] Sanjay Parekh: It was fair use. Totally fair use.

[00:05:15] Joe Casabona: Exactly. And it, yeah, it was all public domain songs. And I would guarantee two-day delivery on these CDs. So, I'd basically say, hey, just the CD is three bucks. If you want the CD with the case, and like some artwork, it's five bucks. And if you have a CD that you want me to fully recreate with the actual artwork and things like that, it's 10 bucks. And I was doing like 60 to 100 bucks a week that way. It was great.

[00:05:46] Sanjay Parekh: Solid. For our listeners, in case you don't know who Zach Morris is, you clearly haven't watched Saved by the Bell. So, I just wanted to give that shout out. Saved by the Bell — classic TV show. Every episode is fantastic. And you can go watch that and understand who Zack Morris is.

[00:06:04] Joe Casabona: Yeah. And he would rent out his school parking lot. Like I was like realistic with my moneymaking aspirations.

[00:06:11] Sanjay Parekh: The principal, was it Bell?

[00:06:16] Joe Casabona: Mr. Belding.

[00:06:16] Sanjay Parekh: Mr. Belding. Belding. He let him get away with a lot of things. I don't think my principals would've let me get away with a lot of those things that were moneymaking ventures.

[00:06:24] Joe Casabona: Yeah, for sure. Absolutely. I was like a goodie two-shoes. Despite that story I just told, I was like a strait-laced person, and so my teachers liked me and let me get away with stuff that way. But I was never a troublemaker like he was.

[00:06:39] Sanjay Parekh: Did you have any entrepreneurs in the family that you were able to watch as you were doing some of these things or was this kind of really on your own?

[00:06:47] Joe Casabona: It was pretty much on my own. My dad, I guess he's a baby boomer. He was born in 1952, and so he was very much like, a get a job. Stay at that job forever and ever. Have a pension. That said, he was very supportive of me. And so, the first entrepreneur in my life that I really liked, that really took me under his wing was Mr. Rizzi, Mr. Joe Rizzi. He owned the deli I worked at. I'm a New York Italian, so of course I'm like a giant stereotype. And every Saturday he would basically talk to me about how to run a business and that's how I learned like a lot of my really early lessons.

[00:07:30] Sanjay Parekh: Yeah. So, I got to ask, what's the one lesson top of mind from Mr. Izzy that really stands out to you?

[00:07:38] Joe Casabona: If you don't charge enough, people will think you do bad work. So, he was like, how much do you charge for websites? And I'm like, $10 an hour. He's like, no. He's like, you charge $25 an hour. And I'm like why? He's like because if you charge too little, then people won't think you do good work. Do you do good work? I'm like, yeah, I do great work. He's like, that $10 an hour doesn't tell me that. So that was like the first time I was like, dang. It's not just like a race to the bottom, like your price kind of dictates the perception of your product or service.

[00:08:12] Sanjay Parekh: Yeah. That signaling, I think that's one of the challenges for a lot of entrepreneurs, is that signaling of price and what it tells the customer. And we always fall into this trap of, but I just want the customers to come and so I'll make it cheap so they'll come. It still doesn't fix it. There, there's a classic story of, I think it was turquoise being sold at a Native American store and it was discounted, and it wouldn't sell, and then they increased the price and everything sold because it kind of implied that, oh, this was very valuable.

[00:08:45] Joe Casabona: Oh, why is this one more expensive? Yeah, and it's like a lesson you constantly learn, right? Like when we were buying our house, there was this house that looked beautiful from the outside. But it was about 30% less than all the other houses we were looking at.

[00:09:01] Sanjay Parekh: Uh huh.

[00:09:01] Joe Casabona: And I was like, what's wrong with it? What is? And it was like a fixer upper, but you couldn't tell from the outside. It was only on the inside. But my first instinct wasn't, ooh, a cheap house, let's go for it. It was like what's wrong with this house? That it's so much cheaper than everything else.

[00:09:17] Sanjay Parekh: It could have been, they were just desperate to get out of it. But you’ve got to figure out what the issue is.

[00:09:22] Joe Casabona: Yeah. And this was before the pandemic. So, this was like, not when people were like paying like straight cash, like 30% more than it was worth just to get it, right?

[00:09:34] Sanjay Parekh: Yeah. Yeah. It has been definitely nuts in that area. Let's think about how you manage all of this stuff now that you're doing your own business. And the stress of it, right? Like one of the challenges for a lot of entrepreneurs is that, honestly, you can work all the time. So how do you balance that with your business and the stress of all of it?

[00:09:58] Joe Casabona: Yeah, it's really tough because when I was like single and had no other obligations, I would just work all the time. I would tell people I'm so lucky that what I do professionally is also the thing I like to do as a hobby. And so, since then though, I have three small children. Like six, two and one. I have a wife who's a nurse and so we’ve got to make sure that we see each other. So, what I do is, I try very hard to do this. It doesn't always work but I have a few focus modes on my phone that turns off email and certain calls and things like, at a certain time, it blocks certain apps. In the office, I have a list of things I want to get done each day. If I don't get those things done, I don't keep working until the list is done. I have what I call a shutdown routine, and so I open up a page in my journal for the day and I just write down what I call all the open threads. And so, it lets me brain dump all the things that I didn't get done that day. That way I'm not thinking about them later. The third thing, and this has been the most effective, is my daughter will say, daddy, you're on your phone a lot. And then I give it to her and then she hides it. That kind of forces me to be present. And I understand that not everybody has a kid or has a kid who's as forward as my daughter is. I wonder where she gets that from. But that — having kids — has really helped determine boundaries and borders.

[00:11:41] Sanjay Parekh: And so, when she takes your phone to hide it, I'm assuming you don't know where it is, like you close your eyes and she runs and does it somewhere. Is that the deal?

[00:11:50] Joe Casabona: Yeah, and she's not the best hider. She usually puts on the same part of the bookshelf but it throws a switch in my brain that I'm on my phone so much that my daughter has noticed. And so, then it's less out of sight, out of mind, and more okay, I need to be present. I'm on my phone now. It's not in arm's reach at least. So, I'm going to be present here and right now because, I also have my Apple Watch, so if I get a crucial text message or whatever, I'm going to see it, but I'm not going to be checking my email for the millionth time, hoping that I sold that one more course or whatever.

[00:12:37] Sanjay Parekh: Right. Right. Are there other kind of boundaries that you think about in terms of work and the rest of life that are sacred to you and how do you enforce those boundaries?

[00:12:48] Joe Casabona: Yeah. For a long time, I would say I'm only doing work in my office. So, like I have a laptop, but I'm not working at the dining room table. Or whatever. When the pandemic happened, I got pretty sick of my office pretty quickly. But as far as figuring out those boundaries, I try to get out of the house and work a little bit, but I think the thing that, honestly, the thing that works the most for me, I should say, that when it comes to boundaries with external facing potential clients and contacts, I don't answer their emails right away. Some of those, like old time, like kind of older rules, I don't answer their emails in the evening. That's just something that I ingrained in myself over time. And then again, like when my kids are home and I got everything I need to get done and I had a full day. That's the other thing, if I leave in the middle of the day to spend time with my family, just knock off work because I can do that. Or like my daughter's in the school Christmas pageant. And I leave work to watch that, then I'll work in the evening a little bit. But if I get a full day, I leave all of my work stuff in the basement and then, it's again, it's like that physical boundary. If I want to do work on my laptop, I have to go downstairs. In front of all my children and my wife, and like essentially announce, hey, I'm going to ignore you and get my laptop. So that has been the biggest driver for me. But as somebody who's been self-employed for, since 14, some of the things that people struggle with, like working late into the night or all hours, phone calls and emails, that's stuff that I kicked pretty early on, like in college. I just knew at some point that was really important, to draw that boundary.

[00:15:00] Adam Walker: Support for this podcast comes from Hiscox committed to helping small businesses protect their dreams since 1901. Quotes and information on customized insurance for specific risks are available at Hiscox.com. Hiscox, the business insurance experts.

[00:15:21] Sanjay Parekh: Let's talk about one of the things, I think that's an issue for a lot of entrepreneurs, is do you have fears? I'm assuming you do, about what you're doing and what are they and how do you deal with them?

[00:15:38] Joe Casabona: Yeah, speaking frankly as we record this, I had one of the worst three-month runs of my professional career at the end of 2022. Where a lot of my money at that time of the year comes from sponsorships and everybody just set their budget like super late. And so, I wasn't making the money I expected to make. That compounded with the pivot that I did in May of that year, where I was only focusing on podcasting and I freaked out like pretty hard, because now I have real stakes. I have children, and my wife works, but we have a mortgage. Our mortgage obviously went up in that time too, because super weird how no mortgage company can properly calculate taxes. And when I have those fears, the biggest thing that helps me is my wife. She's so supportive. She's like, you've done this before. You're there, you're fine. And I think about how every entrepreneur goes through these things.

We like to focus on always the good. Just like I would say this all the time, early on in my podcasts, we always look at the Olympic gold medalist as if they're always standing on the podium. But for 10 years before that, there was like blood, sweat, and tears and failure and their body breaking down. So, every entrepreneur goes through this and weathering that storm and understanding that this is just part of being in business and having the right support system and tent poles in place and being willing to make the changes you need to make to get back on track. That's how I overcome my fear. I'm very much a ‘I have to fix the problem right now’ kind of guy. And so, when something happens, I always go, how can I fix this? What's the best way for me to do it?

[00:17:48] Sanjay Parekh: The challenge right there I think you've honed in on is that, we so much as a society will only talk about the time when you're on the medal stand, getting the gold medal, right? Nobody was writing stories about the 10 years beforehand of, oh, Simone Biles was at practice today and she failed again. Or whatever. But, pay attention because in eight years she might get the gold medal. There's no story because it's not interesting at that point. It's only interesting at the gold medal part.

[00:18:21] Joe Casabona: And then after the fact, right? Have you seen, I'm a huge Yankee fan. Have you seen The Captain, the documentary series, The Captain?

[00:18:28] Sanjay Parekh: I have not.

[00:18:28] Joe Casabona: Okay. So, Derek Jeter, one of the most celebrated athletes of all time, I would say. Then maybe that's my bias showing, but they did a six-part documentary on him, so maybe not. But in the first episode, they talk about how most scouts are like, this guy's going nowhere. Nobody was writing about Derek Jeter, about this kid not going anywhere. But it's an interesting story now because of how successful he was. So, it's important when you're in it to think about, I can get through this. Other people have gotten through this, other people have faced bigger adversity than me. I can get through this.

[00:19:15] Sanjay Parekh: Thinking about the adversity, looking at now you've gone through a tough time, thinking about like your current year and the next year coming out of that, what makes you nervous? About what's happening next?

[00:19:28] Joe Casabona: I think, and I knew this for a while and it never really hit me because again, like November every year, it's like a bunch of brands want to sign on for a year sponsorship until November, December, it was always great for me. And set me up for basically the next year. But in the back of my mind, I was like, you're relying too much on other people's ad budgets, right? And so, this year a fear, and the thing that's driving me, is I want to be less reliant on that, and I want to sell my product specifically, right? That's the most scalable thing I have, and I want to be able to sell more of that.

That was part of the whole simplifying my offerings and pivoting back in May because if I'm selling too many things, right? Like you don't want to go to like a mechanic, who's also a dentist, who's also a computer repair person who also like, makes falafel or whatever, right? Just watched Batman Begins. So, falafel's, like, in my head. You're going to be like, which one of those can you actually do? I don't want to be that person. I want to be the person who says, oh, Joe eats, sleeps, and breathes podcasts. He can help me with my podcast.

[00:20:48] Sanjay Parekh: Diversification of revenue is probably one of those things that you've touched on there. Is probably one of the most important things too for entrepreneurs to be able to be successful and survive through everything. And we see a lot of times, entrepreneurs have too much revenue from too few clients or even one client and something, and it can be fine. As long as nothing happens, but the minute something happens, it can be disastrous. Have you thought about that in terms of how you get your revenue and do you look at where you're getting revenue from and who's the biggest percentage, and how do you deal with that?

[00:21:25] Joe Casabona: Yeah, for sure. And that's definitely a mistake like freelancers make, right? Oh, like 70% of my income comes from this one client. You're basically their employee then, and they could fire you at any time, right? And you don't get severance. I think that a lot of people, when they hear, diversify your income, they think I need new products, or I need more products, or I need more offerings. That's a mistake I made for a long time. That's why I did so many things. I was like, oh, these are all income streams. I'm doing it the right way. But now what I've realized is I have one core offering and what my friend Chris Lema calls the product ladder, right?

I have different products, different income coming from different places. And so right now the lion’s share of my income comes from two places: LinkedIn Learning and the courses I do for them and the royalties I get from those courses; and sponsorships. And I made a tough decision in September or October that I was going to stop doing LinkedIn learning courses because I was doing almost one a month, which is more than you're supposed to do, right, as a contract instructor. And they were taking up a lot of time that I wasn't spending on my own business. And so, I've basically, aside from royalties, I've cut off that part of my income, and now I'm signing a few brand deals as we record this.

So, everything that got delayed in the last quarter is finally coming in this quarter. But what I'm thinking about is, okay, in my podcast offerings, how can I go through the journey with my customer? So how can I meet them where they're ready to get something from me? So, I have the $39 thing, right? Oh, hey, this is just going to get you off the ground a little bit. I have the $399 thing. Oh, hey, this is going to give you a more self-paced, but like all the information, everything I've ever learned as a podcaster is here. The coaching program, hey, let me hold your hand through some of this stuff. And I have that Done for You program, which is don't even worry about it. I'll do this for you. I'll let you know when it's done. Here you go. And so those are the things that I thought about last year coming into this year. It's not about having a bunch of different products or it's not about having a bunch of different businesses. It's about where can I meet people in my niche at different parts of their journey?

[00:24:00] Sanjay Parekh: Yeah. Interesting. I love it. I love it. Okay, let's move to something that I think hopefully the listeners have been waiting for. I've definitely been waiting for it. What do you have in terms of recommendations for, first, technology apps or systems that you've implemented to help you manage your business? And then the second part of that is, what do you have for recommendations for somebody that's wanting to start their podcast in terms of technology apps or systems? So, let's start with the business first.

[00:24:27] Joe Casabona: Yeah. My toxic trait is automating things that probably don't need to be automated. That said, I think that automation has been such a crucial part of me being able to stay as just me, as my only full-time employee. I have a couple of contractors. So Zapier or Make. If you're going to have more than five automations, look at Make, because it's 90% cheaper than Zapier. Those things, connecting one thing to another, making things happen automatically, so I don't have to think about it. That more than anything has helped me become a profitable business and a profitable podcaster.

Like my guest flow for podcasting. Somebody signs up for a Calendly link. They get all the communication automatically. It gets added to my episode system automatically, it gets added to my show notes automatically, me and the guest chat. I add those the recordings to Dropbox, and then I never see the episode again until it's live. Because between automation and my editor and my VA, I don't have to, anymore. I have those systems in place. So, make.com, formerly Integromat, Make is a terrible name for Googling. And a brilliant name for what you actually do. But make.com has been so big for me. The other thing that's been big for me is Airtable. I use Craft as my notes app, and that's technically my second brain, but Airtable is like my business's brain, I guess. All of my planning, all of my organization, all of my bunch of numbers I run are all in Airtable. And I know Notion’s like the new hotness, but like Airtable is just Airtable's been there for me. I love it.

[00:26:23] Sanjay Parekh: Okay. What about on the podcasting side? A tool or a system or something that somebody should implement if they're going to try to launch a podcast.

[00:26:31] Joe Casabona: Yeah. If you want to launch a podcast today, right? Because it's time consuming. We both know this. I think a mini podcast is the way to go. So that's like a solo show, 20 minutes or less. That's going to be easier for most people to start. And so, if you're going to do that, Descript is what you need, right? Because you can record in Descript. It's got really easy tools for improving your audio if you don't know how to edit. And then when you do edit, it's like editing a Word doc or a Google doc Word doc. You delete text and that audio is deleted, and then you publish directly to your audio host. So, Descript is like a one-stop shop for everything. And then you have the benefit of getting these auto-generated transcripts, which those are better than no transcripts. And so, you have the whole package right in this one app.

[00:27:21] Sanjay Parekh: I love it. I love it. Okay, last question. What would you tell somebody that's thinking about either launching a side hustle or taking their side hustle into a full-time gig like you've done?

[00:27:37] Joe Casabona: My network saved me. When I left my full-time job. Two things were true. I had a new family to support, and I was full of hubris because my old job was having trouble paying us on time. And the thing that made me leave was being told by the project manager, hey, if you want to get paid on time, you have to work this weekend to finish this project. And I was like, that's not the social contract that we had. But even outside of that, I didn't feel the crunch of getting paid late because my side hustle was bringing in money. What I didn't realize was side hustle money is not full-time gig money, because eventually I'd get that payment and it was usually within two weeks. And so, my network saved me because I was like, I panicked. I was like, I have no money. And apparently like the money I was making is not enough to support my family. I reached out to a few people. I landed a big sponsor, and I landed a contract gig with a friend making educational videos. If you're going to go out on your own, know how much you need to make before you go out on your own, make sure you have some money in the bank and build a network of people in your niche who you can work with, because that, I cannot express my gratitude enough for them. My business would not exist without my network and the podcast.

[00:29:10] Sanjay Parekh: I love it. That is great. Great advice. Listen, Joe, where can our listeners find and connect with you?

[00:29:16] Joe Casabona: You know what? I have some resources set up for you for like my podcast planners and things like that. If you go to podcastliftoff.com/sidehustle, all one word you will get more information about where you can find me. You can join my mailing list and you can get some free resources over there.

[00:29:36] Sanjay Parekh: That's awesome. Thanks so much, Joe, for coming on the show.

[00:29:39] Joe Casabona: My pleasure, Sanjay. Thanks for having me.

[00:29:42] Sanjay Parekh: Thank you for listening to this week's episode of the Side Hustle to Small Business Podcast, powered by Hiscox. To learn more about how Hiscox can help protect your small business through intelligent insurance solutions, visit hiscox.com. And if you have a story you want to hear on this podcast, please visit www.hiscox.com/shareyourstory. I'm your host Sanjay Parekh. You can find me on Twitter @sanjay or on my website at www.sanjayparekh.com.