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In this episode, I speak with Kevin Chemidlin, a fellow podcaster and the brains behind Grow the Show. Kevin's journey from a successful corporate career to full-time podcasting is a story that resonates with anyone who's ever felt the pull towards entrepreneurship. His candid sharing of the highs and lows, including the tough decision to leave a stable job and the challenges of navigating the podcasting world, is both grounding and inspiring.

Kevin's transparency about the realities of growing a podcast and a business is refreshing. He doesn't shy away from discussing the setbacks he faced, including the impact of COVID-19 on his podcast Philly Who and the tough lessons learned from expanding his business too quickly. But it's not just about the struggles; Kevin also shares the strategies that led to his success, making this a must-listen for any podcaster looking to grow their show and turn their passion into a profitable venture.

Join us as we dive into the importance of community, the power of resilience, and the practical steps you can take to make your podcast thrive. Whether you're a seasoned podcaster or just starting out, Kevin's wisdom and experience are invaluable. So, if you're ready to take your podcast to the next level, tune in and let's grow your show together!

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Key Takeaways

00:00 Entrepreneurial Journey to Podcasting Success

11:22 Call Your Parents, Prioritize Building Systems

20:31 Podcast Growth and Monetization Insights

26:53 Sponsoring Podcasts and Overcoming Failure

32:52 Growing a Successful Podcast

40:02 Business Growth and Lessons Learned

45:57 Lessons Learned From Entrepreneurial Challenges

53:31 Podcast Growth and Connection Through Vulnerability

Tweetable Quotes

"I tried nine to five; didn't work for me. Despite Cigna's best efforts to give me everything I ever asked for, the whole time, I knew I wanted to be an entrepreneur. So I had all kinds of really weird side hustles throughout those four years."

"It's been full time, literally nothing but podcasting. It's been six years later, and I've only done podcasting. I was so excited for it and it got a little bit of buzz. People were talking about it a bit, and I was like, 'Ah, finally, I got my thing.'"

"You have to learn how to prioritize things that you really don't need to do today but make all the difference in the world to make the product better all the time. Learning how to think in systems has helped me with working with clients, working with people, working with employees, and made me a great dog trainer."

Resources Mentioned

SIGN UP FOR KEVIN’S COURSE: https://www.growtheshowlive.com/harry

X/Twitter - https://x.com/kevinchemidlin

Instagram - https://instagram.com/kevinchemidlin

LinkedIn - https://linkedin.com/in/kevinchemidlin

Podcast Junkies Website: podcastjunkies.com

Podcast Junkies YouTube: https://www.youtube.com/c/Podcastjunkies/

Podcast Junkies Facebook Group: https://www.facebook.com/groups/podcastjunkiesjunkies/

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Podcast Junkies LinkedIn: https://www.linkedin.com/company/podcastjunkies

The Podosphere: https://www.thepodosphere.com/

Podcast Index, Value4Value & NewPodcastApps: https://podcastindex.org/

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Mentioned in this episode:

Podcast Blueprint 101

So Kevin Schmidlin, host of Grow the Show. Thank you so much for joining me on Podcast Junkies.

Harry, honor to be here, man, so pumped I've been a longtime follower. It's so cool to be here on the show For the benefit of folks not watching on YouTube.

you've got a couple of seats back there, so is that your recording area back there and for you when you do live stuff?

Yeah, no, what's funny is, it's just my background for my remote stuff. So I've never actually done a live interview back here. I'm based in Miami these days, and so there's tons of folks around here that'd be great to interview. So I've been thinking maybe someday I should, you know, have some folks in, but not yet.

No, it's just been so long. Have you ever done an in-person?

interview. Oh yeah, so my first really, until COVID hit. I was exclusively in person. So in person. So I launched my first podcast in 2018. It was about my home city of Philadelphia. Like I said, I live in Miami now, but that was all completely in person, so I would interview successful Philadelphians. The first year I just had two Shure SM58s and I would just run around the city and interview them in conference rooms. Then, eventually, in 2019, I built a studio in Philadelphia.

It was called the Philly who Studio. Then COVID hit and that was that for a while. And I actually don't know if I've done an in-person interview since then, which is funny, because back then I was hardcore, I was like I will only do interviews in person. Right, like I was, like it's got because of the vibes right, you get to know somebody. Since then I would almost be intimidated to do an in person when it's been so long.

I think what I thought was interesting is that I was looking at your LinkedIn and you previously were working at Cigna and what I loved about the profile is normally people when they have like past positions there, you know, they talk about what their role was. You know I was like project manager, you know whatever it was, but yours was really brief.

And it basically said like I tried nine to five didn't work for me and that's about all you had there. So talk to me a little. An excellent professional development program and to this day, my best friends in life are the people that I met and worked with in that program and I have nothing but good things to say about Cigna, or at least the time that I worked there. It's been a long time, I don't know if it's changed. I know they've been through some mergers and stuff, but yeah, I mean the people were awesome. I got every role I ever wanted right. So, like in my tenure, I had three different roles. Every time I asked for one they gave it to me Like I just was. I was passable, right, but like I didn't care about it enough to get really good at it. I remember the people that I worked with would like stay, like they would go home and they would work more on code by choice, like it was not something that their bosses make.

They're like, I'm going to go home tonight and fiddle with this and figure this out and I would be like man, I just don't like that's awesome, but no way would I want to do that. And I also just like, like I said, the company was great, but just wasn't super jazzed up about writing like backend insurance batch software.

I was like this is okay, right. So, despite Sigma's best efforts to give me everything that I ever asked for, the whole time, I knew I wanted to be an entrepreneur. So I had all kinds of really weird side hustles throughout that four years. One of them was a music recording studio in my basement, but I was like I wound up just being too tired every night to do that. Well.

And then the next one was an app to help roommates split the rent and then something came out like, I think, splitwise came out and I was like oh man, I'm not going to be able to beat them. Then it was right around the Pokemon go era. A buddy of mine and I developed a app that was geolocated digital pinatas. So yeah, super wonky, we did well, we launched we got 500 users.

We had a couple like business partners in Philly using it, but again like six months in I was like I don't know if I want to do a venture capital backed social media app about pinatas, so I stopped doing that Then I read 4-Hour Workweek and I was like, oh, I should do a physical product, like something that I can just make and sell. And, dude, I like I created a lockbox for people to have outside of their house, Cause in Philly it's a bunch of row homes and people's packages get stolen all the time.

So I created this lockbox where, like, the mailman can like put stuff in the box and he had the code. I spent like 20 grand on credit cards, working with like manufacturing company that had a branch in China and like trying to figure out how to do that. And then I got the prototype and I put it outside and the prototype got stolen.

That's bad for PR.

Yeah, I'm like, oh, this is no good. So after this, it was like the fourth or fifth like failed thing. And it's funny because the summer of 2017, I was like, okay, fifth like failed thing. And it's funny because the summer of 2017, I was like, okay, I'm going to just not have a side hustle for a while, like I had savings because I knew at some point I was going to take the leap and be an entrepreneur, so I was building up savings, but I'm like I'm going to spend a little bit. I'm going to just do a little bit of traveling over the summer. I've got tons of paid time off accrued and I did that. And during that time period, I started listening to podcasts, and it was in December of that year, 2017, I was listening specifically to an episode of how I Built this with Guy Raz, and it was about Warby Parker, the glasses company, which I didn't know until I heard the episode, but they were founded in Philly and that's what I'm trying to do. Oh my God.

I was electric.

Now I was super caffeinated and jacked up but like I was like this is so cool. And I was like I want to hear more story. I want to hear more Philly stories like this, like Philadelphia success stories, but in this way and let's like super cinematic storytelling, like NPR style way. So I was like, okay, I'm going to launch a podcast, but this is not going to be my side hustle, this is not going to be my thing. I'm just going to do this off to the side while I figure out what the real business is going to be. And six years later, I've only done podcasting.

The show had gotten maybe 400 downloads in total at that point because it was around for three weeks, which, by the way, I know now it's actually a pretty good show that has no audience and no background.

I didn't know it at the time but I was just so excited for it and it got a little bit of buzz, like people were talking about it a little bit, and I was like, ah, finally I got my thing. So I gave notice. My boss's boss was like. I told him hey, man, I'm done Two weeks. And he gave me a look and he was like okay, where are you going? No-transcript, and I'll never forget the look he gave me. He like kind of like, have you ever seen a puppy who hears a noise for the first time? They're like trying to turn their head and they're like what? And also, people were not being podcasters back then.

Nowadays we say full-time, but that was not a thing, right? So he was like, okay, that's awesome, super supportive dude, like again 10 out of 10. But he was like, all right, you have a home here. If you want it, like, just let me know, we've got a spot for you. And I mean, six months later I had my phone out and I was ready to call him back because I ran out of savings and like I had spent six months, just spent 40 hours a week on the podcast, tons of editing, tons just like grunt work, and I was flabbergasted as to why it wasn't growing because I kept publishing. I was being super consistent. You know I was back then.

Audiograms were the big thing because Instagram had just allowed you to post videos for the first time and six months later, like no growth, cranking out episodes, and I'm like what am I doing? Like I was just getting nothing out of it. No idea how to monetize, and so that was kind of the low point where I almost I don't like. I said I almost called him back, I went back to the job.

Yeah, that's interesting. So we'll pause there for a second because I want to. That's sort of like where we're going to pick up, but I just want to rewind the clock a the sense, from everything you were doing, the side hustles and obviously where you ended up now, there was a bit of entrepreneurial streak, either in you when you were younger or something that was inspiring you when you were growing up. So I'm curious if you think back growing up, pre-college days, is there something in you or in your DNA where you can look back now and say, oh yeah, I can kind of see where that's coming from in your DNA, where?

you can look back now and say, oh yeah, I can kind of see where that's coming from. Yeah, so it's totally in my DNA. Specifically, my grandfather, my father's father, was somebody who always had not necessarily entrepreneurial I mean, he did wind up in the end owning his own and he's still around, like I don't mean in the end, like he's still with us, but he wound up becoming a financial advisor and very much like had his own client base and everything like that. But he wasn't like. He's never owned a business as far as I know, but he always. He was an organizer, he was always like he.

Over the course of my dad's childhood he founded two separate softball leagues in different cities and was super active in his church and everything like that. So my parents always tell me that I have pop-ups, blood or whatever. You know I'm always because growing up up it was always that's what I like to do, like I was. It's funny my girlfriend and I are binge watching modern family right now and there's this character on modern family, this young kid named manny who's he's like 10 years old but he like talks like a 50 year old. That was me. I was manny. Like I didn't. I wasn't interested in playing video games and stuff. I was doing weird things like creating in sixth grade.

I had a pencil rental business, because kids were always bringing a pencil to class and that got shut down and I organized the wiffle ball league Like I was a commissioner of a self-organized wiffle ball league, like all these ridiculous things. In college, yes, I majored in computer science, but really I majored in acapella. So I co-founded an acapella group and grew that and that was when acapella was like really it was cool for like two years and that was when I was in college any videos of you on youtube all the way back.

Oh my gosh yeah, if you search gavin schmidlin.

Yeah, I mean probably on the second page or whatever like there's I mean one of those links we'll put in the show notes too yeah, for sure, yeah, we'll do but yeah, it's just always been a thread for me.

I've always had some sort of weird project that I get way more serious about than anybody should, and it's I mean. Now it's, I'm glad, but for a long time I was like, why can't I be normal?

Well, it's interesting because as my folks get older. They're both 80 now and they live in New York. I'm in Minnesota, so you know I don't get to see them as often. So I'm always conscious of like thinking back, of like the influence like my dad and my mom had on me growing up and also communicating that to them, because different generation, different time, not very emotive or communicative, and so sometimes I've done a lot of work on myself, like men's work, in the past couple of years, just kind of like realizing how important it is to have those conversations, because the moment they're gone you're going to wish you had like some time.

I saw someone produced a set of cards called Tales, talescom, and it's just a box with cards and you take the cards and you ask, like your folks like these questions, like what was your most memorable experience, like when you were six years old? And it's interesting because it's things that we need. And I think about this a lot because I talk all the time. We're podcasters, right, we're talking to people all the time. We're getting these in-depth conversations. I'm like I get deep with these folks that I meet for the first time and I'm like I need to like translate that back into like the real world, with the people that my siblings, my brothers, my sister, my family. I'm conscious of that all the time. So, as you were mentioning, that sort of came to mind and I was thinking about that.

Yeah, my mom recently said to me. She said you need to call me more, right? And I feel like everybody's mom says that. But she, as soon as she said it, she was like not for me. Like, of course, you know that I love talking with you and I'll literally talk to you every day. It's not me complaining that you never call me, it's me saying this is her talking. Both of my parents are gone. I would give literally anything to have one conversation with either of them. So she's like you need to call me now, because there will be a day where you can't. And I was like oh, yeah, for sure.

Yeah, oh, my God. So if there's a takeaway for the listener and the viewer as a result of this conversation, as soon as after this you listen to this podcast episode call your folks, please.

Yeah, yeah, if you're lucky enough to still have them with us.

In the little time that you spent in the corporate world you got to see. You know, obviously the benefit of there is having the structure and then the management structure whether you mentioned your boss's boss. But were there anyone else where you figured like you did learn some stuff there? That might that you think of now, or has that's been helpful for you?

Yeah. So it's funny because the first couple of years of entrepreneurship I was bummed that I had spent four years in corporate because I felt like I had wasted that time Right. And I also look, I looked around at other entrepreneurs that I started learning from who started really early and I was jealous, like that. There's these entrepreneurs who have already built seven figure plus businesses and they're like 26 or whatever no-transcript, like when you're developing software features, except for ones that are like fixes, like production issues that you need to fix right away. You have to learn how to prioritize things that you really don't need to do today but like it's all the difference in the world to make the product better all the time. So that was the first thing that I took away. But secondly, just learning how to think in systems, like when you write code, like, and it's actually helped me with working with clients, working with people, working with employees, and made me a great dog trainer is.

You know, when you write code and the code doesn't work, you can't blame the code, right, there's an issue with the code. You have to figure out what's wrong with your instructions, right, and in addition to that, when you're writing code that's meant to interact with each other, you have to get so good at thinking about systems. What is the input? What is the process right Like? What are the steps in order? What's all the information that's needed to do the task? What is the desired outputs? So, like now, I just see building a business and working with employees and building a team and all that stuff is literally writing software, essentially Only. Instead of writing code that a computer executes, it's writing process. It's writing words and processes and instructions that a bunch of people execute. So without that and also, by the way, I can code.

So like I can like write my own Zaps, and you know what I mean Like write my own software and stuff and I'm really technical so I can like if there's an issue with my CRM, I can fix it in 30 minutes. I don't need to like find someone and hire them like all that stuff. So at first I was super bummed, but nowadays I look back and you know just, I'm so grateful that I took those four years.

Yeah, especially having that discipline and a business owner and an entrepreneur. You do think about all the other functions that in the corporate world you take for granted, like there is an accounting team, there's a tax team, there's a marketing team, there's a sales team, there's a tech team.

You know there's a website team and you as the entrepreneur and obviously I'm into heading into like the ninth year of my podcast agency and just just realize as you grow and you start to develop partnerships with other companies and you got to get your tax strategy in order and like set up your companies correctly and pay on time and so many moving parts that you sort of have to learn. Like if you are serious about growing a company you have to. The front facing stuff is fun and I'm sure to people looking in from the outside, or maybe even some of your peers from the corporate world, they're probably like oh, that looks cool what you're doing, but like it's like that duck on the pond looking super cool and calm but underneath his feet are like going a million miles a minute.

Oh my gosh, a hundred percent. Yeah, I think about that when I see these TikToks of people like complaining that they had to work two hours in a day and I'm like you have no idea how much structure and like systems and how much building went into your ability to only work two hours a day. It's crazy.

So when you started the Philly podcast, did you have a structure in mind? Did you have some inspiration? Did you know what you were going to do in terms of like? Obviously you've got the tech gear, you've got the two mics, but then, like logistically, recording in person is always presents its own set of challenges. But how did you find that you were maturing, probably quickly, as a host, asking questions, reacting on the fly, because you've got the person right in front of you and you've got to make sure you're creating great content that's compelling to listen to and watch as well.

Yeah, I mean I was fortunate enough number one, like I never talked a lot at work, which is funny because I'm a podcaster and that's all I do now. But I noticed that, like whenever I asked a question in a meeting, almost every single time I asked it someone would say that's a good question. And you know, at first I was like that's kind of weird, like why do people always say that when I ask questions? I'm like, hey, you know, I'm like am I asking weird questions? But then with time I was like you know, maybe I don't know, maybe I should lean into that a little bit. So I took that forward and then with I mean I had the idea for the show in December. I didn't launch it until May, and so I really took three to four months and did a bunch of studying.

I was super into Tim Ferriss' show at the time still am probably more so then and you know he had some episodes and blog posts about what he had learned about the craft of interviewing. I had gotten in touch with a couple interviewers to ask advice like, including Guy Raz Cal Fussman's another one. I managed to pull him aside at a conference and ask him some questions. So that was the one thing like what I didn't know to look into and learn how to do before launching the podcast initially was learn how to do marketing and monetization and business.

I spent all of my time learning how to do interviewing then. So then, by the time I did and I did a couple of practice interviews with some buddies, just like asking them questions about their life and stuff which, by the way, in the same vein of what you're saying, like asking your friends these like deep questions about their life story you I was like I didn't know that dude, I had no idea you lived in Argentina for three years. What men?

don't talk about that stuff and so like that was really that craft is really. That had all of my focus out of the gate, and I would later learn that I needed to focus on marketing and business and sales and all these things to monetize and turn it into a business. But that's literally like a full-time member. I got rid of my job so all I had to do was prepare for an interview, wake up, do the interview, focus on crushing it and asking great questions and then go home and edit it. That's all I did. Don't recommend it. I don't recommend it. Right Made no money. Right Like it was a very privileged position to do that.

But yeah, that's, I mean, kind of lucked out. That happened to be that I was able to go all in on it for like six months and really get good at it.

You mentioned that the show had a decent following in terms of like people in the local community, because obviously that's the challenge with the show about Philly it's likely going to be attracting and interesting only people that are interested in what's happening in and around Philly and specifically in and around Philly with the business world or the focus of the people you're speaking to. So this is something that a lot of podcasters have to deal with this idea of like do I continue my show right, when is the time? And so, with the Philly show, when was the writing on the wall for you where you realized that it might be time to sunset or it might be time to move into something else? What was it about that timing or where you were with the show that was forcing you into making that decision?

Yeah. So it was six months after leaving the job was out of cash, out of savings, starting to go into credit card debts Again super ill-advised. Out of cash, out of savings, starting to go into credit card debts Again super ill-advised. I don't recommend it to anybody. And honestly, at that point all logical signs said sunset the show. You've been doing this for six months. It's not growing at all and I think a lot of newer podcasters feel that way. And that's what goes into Podfade where you're like all right, I've tried this for six months, it's clearly not working, quote unquote.

But I had made such a big stink to everybody in my life about the fact that I was this cool podcasting entrepreneur now that I just couldn't handle. I couldn't handle it. I couldn't handle the thought of calling the boss back and going backwards, or at least what it felt like going backwards, even though it would have made complete financial sense to go get the job, get out of debt and start over. So what I did at that moment was I stopped publishing the show, put it on pause. I was like I'm not going to quit entirely, but I could stop publishing episodes to nobody for a few weeks. Right Break the, which is hard because it's pounded into our head as creators to not to never miss a week.

Be consistent, be consistent be consistent, be consistent, Right. But at that point I was like, okay, I've been consistent. Like, clearly, consistency alone is not. There's something else that I'm missing here. So I put the show on pause. I said, hey, everybody, I'm taking a break to the like 200 people that were listening and didn't get the job back. I was like I can borrow some more money and some more time. And just like I was like what are these other podcasters doing? Like there's clearly other shows that have figured this out, so what are they doing? What am I missing here?

And I took a weekend and listened to every single show on the Apple 100 charts. I just like walked around Philly. I walked like 18 miles over the weekend and just didn't listen to every single full episode. But like, what are the interests sound like, how are these monetized? Who are their sponsors? And took some courses, read a bunch of books. I was like I'm going back into study mode, Like I did before I launched the show. I studied interviewing. Now I want to study growth, like marketing. Like what, what am I missing? And so I learned a ton in that six week period and I was like, okay, there's something different here. Like I'm missing a bunch of pieces brought the show back, and then that's where the Philly show actually started to work. Within a year after bringing the show back, it had gotten 100,000 downloads total, which for a local show is pretty good, and I had managed to generate about 120K in revenue through sponsorships, live events, merch sales, Patreon you name it like tons of different monetization metric streams. And then COVID hit.

But that year 2019 was awesome, so that's good. Another inflection point. So let's now look at that. So you're listening to all these shows, you're taking copious notes and so if you could boil down whether that's three things, five things, whatever it comes to, the main things that you realize, oh, this is the differentiator, this is what I need to change in my show. What were those things? The key drivers? You know we don't have to get into the super specifics, because obviously there were some thing that the levers that needed to be moved that you didn't have, and you obviously felt that, in your capacity, that you could change those for your show. And so what were those?

Yeah, there's three main insights that I got right, that I've carried everything since then. The first is the understanding that with audio podcasting, if you build it, nothing will happen. I spent six months. All I did was work on my podcast and edit and make a great product, and it was. It's an amazing show. I still have people reaching out who are like this is one of the best audio like histories I've ever heard, for one person. So I'll say it was really good and so at that point I was like there's got to be.

I think I've maximized how good this show is. So I don't think that it's not growing because it's not good. So while quality is, again, it's table stakes. Like, consistency and quality are table stakes. They are the minimum, they are a requirement. You can't grow without them. But those two things alone is not enough. That was number one. Number two was so number one was basically I have to go make people find out that this show exists. It's not enough to just hit publish. So that was the first insight. The second insight was I don't go make people no-transcript realize was that I was emulating podcasters who also had no downloads, because I love the podcast community. Everybody's super helpful, but there's a lot of people who don't have a huge audience and are sharing their strategies with people and saying this is what I do. Right, it's like, but you can't see that they don't have any audience.

It's not like a YouTube channel where you'll be like I'm not going to listen to that guy.

He's got 200 subscribers, it's like, oh well, this is what this podcaster told me to do. He's been podcasting for six years, so I should probably listen to him. What you don't know is that he got yourself. You grow your show by participating elsewhere. So that's participating in online groups not promoting, but participating in the group, participating in live events, participating on social media right. So it's not like listen, listen, listen. It's hey, look at this post. Right, participating in trends, like putting out useful social media posts. So that's. The second thing is don't promote, participate. And the third thing is I was always asking myself how do I monetize? How do I monetize? How do I monetize? That's really a horrible question, because at what point is your show monetized? What does that even mean? Right, like, and most people answer when I ask, hey, when is your show monetized? They say, well, when I get paid. Right, that's cool, I'm down. I want you to get paid too. But here's my question.

Who's?

paying you. And then they usually say my sponsors. I'm like, okay, cool, but who's paying them? And that's when they kind of like look up a little bit and they're like, huh, and they're like, well, I guess my listeners. And I'm like, ah, so the third piece, when I asked myself how do I monetize Difficult question to answer what I learned was your audience is monetized. When your listeners buy something, it's either something that you sell them or something that somebody else sells them, aka your sponsors, because your sponsors are just prepaying for your listeners to buy their stuff right, right, exactly so.

if your listeners don't buy their stuff, they're not going to keep compensating you, right, because nothing happened, right. So it's kind of this shift of I want to get paid to do this which doesn't serve you or didn't serve me anyway, and I shifted to be like, okay, what can I get my listeners to buy that I get a cut of in some way. And then it was like I could sell merch, I could throw an event and sell tickets. I can get some sponsors and make sure that they go buy In Philly for a local show. It can actually be easier getting sponsors.

Sure, sure, yeah, it's shops and lawyers and stuff right I can make sure my listeners use them.

Cheesesteaks and other stuff.

Yeah, exactly right, go to this place for your cheesesteaks. And then they all flock there and I'm like, great, I've got a happy sponsor right. So that was the third insight is just monet. So monetization doesn't mean you get paid to create. It means your audience buys something that you influence them to buy and you get a cut of that purchase.

So how did you start piecing it together? And I love kind of digging into the weeds a little bit on that third piece.

And so I'm wondering if you came across that hurdle as well. Oh, totally, what I figured out was, in order for a sponsor to sponsor my podcast, they need to be sold on two things they need to be sold on sponsoring podcasts and they need to be sold on sponsoring my podcast.

two separate things right. So what I figured out was, if I try to go to a company that doesn't know me and has never sponsored a podcast, you're in for a tough battle. You may be able to get them to do a test or something like that, and early on I would be like let me just sponsor, like they would be like. There were a couple of banks that I reached out to in Philadelphia Banks are not local.

Right, and I tried that and a couple of those panned out. But eventually, through trial and error, I was like I figured out the people, the companies that actually sponsored me. Either were listeners already at the show, like business owners who listen to my podcast. They were people who just knew me. So, like my friends, my biggest sponsor, my friend's dad, owns a restaurant chain in Philly Boom. He was like, hey, my buddy's got a podcast, you should sponsor it. Right, easy. And then the third one was finding companies that sponsor other podcasts where they can just throw mine on top Right.

They already have a process, they're already sold on it. So that was the like I got to find. First, find people who know me, like personal network and listeners. Especially Listeners is like ask your like, hey, it's like when you drive by a billboard and it's like sponsor, here, do the same thing on your show.

Or it's like, hey, if you want to sponsor my podcast, right, you'll to listeners who have companies, and then once you exhaust that, or once I exhaust that, I say, okay, what companies are on other spots sponsoring other shows? Let's get past the Squarespace's and the Casper mattresses, of course, but, like, let's see if we can find other, like other shows that my listeners listen to. Who's sponsoring those shows? And then usually that's enough, right, usually. And then, of course, you also sometimes get inbound sponsorships where people like companies reach out to you and it's like, okay, great, that's a way easier conversation to have. But I don't know if I've ever closed a sponsorship deal on a company that had never sponsored a podcast before and had no idea who.

I was. It's so important because it's this concept of like, building on the relationships. You've already got a relationship with your listeners and, in the case of some sponsors that you were working for, you know, through connections with your friends, they're vouching for you, they're vouching for you, they're vouching for your character, they're vouching, if they know you're a hard worker so they, by extension, they trust making this referral that you're going to. You're going to bust your ass to get everything, do everything you can. And I have a mantra with this show it's treat your guests like gold. And then when I started my second show it's, it became treat your sponsors like gold because you have to over deliver for them. Because, especially if they're dipping their toe in the sponsorship waters, we're spokespersons for the podcast industry.

At that point, you know.

And if they're like, oh, I tried to put that podcast thing and it just didn't work out, and it's like, oh, you're souring them now I'm like potentially thinking about this as something in the future.

So every time we land a sponsor like, I'll go on my linkedin and I'll say thanks to xyz company for sponsoring the show like and they see that cause I tag them and they realize well, this is more than I would get if I was just dropping an ad and like a weekly circular or just kind of. I don't know if they do radio ads anymore, but it's like these things that they don't have the capacity to do the above and beyond, because they're dealing with you directly as a person, not another like agency. That just is like looking for numbers. So I really love that you said that, because it's really like you're building that relationship and, as you know and you probably experienced, it's so much easier to renew a sponsor than to like go back in and just go through the grind of getting a sponsor again for the first time and starting that conversation all over again.

Right, and that's what I teach a lot of the podcasters that I interact with on a regular basis. I'm like look like the deal isn't won, like the job isn't done, when the sponsorship money hits right, when you sign the deal, like that's the beginning, not the end. Right, because? People are like yay, I got a sponsor, I'm getting paid.

Great, I can go back to podcasting.

It's like no, no, no, no, no. The work just begins if you want to keep making money right, because and that's a lot those who have worked with smaller podcasters or podcasters that have less experience before they've experienced where they sponsor a show and they literally never hear back from the podcast ever again, like, yeah, the ad goes, the ad airs, but they never. The podcaster doesn't reach out to see did you get any customers? Like, did this achieve the goals that you had when you paid me for it? Or something like you said, like seeing expressing thanks publicly that the sponsor supported the show. They just kind of, you know, take the money and run, which is a bummer because they're not probably not usually being malicious. Like again they're thinking, yay, I got paid to make the podcast right when it's like no, no, no, that's not what this is. You are getting paid to bring that sponsor customers and they're going to expect you to try to get your audience to buy their stuff, yeah for sure.

And so having success with the show. I'm sure you're super pumped. Everything's working out well. You figured out what works, what doesn't. You've got revenue coming in. Obviously, then COVID comes. So talk to me about a couple of things, kevin. I'm curious about this idea of resiliency, and as an entrepreneur, we have to be comfortable with failure, and it's something that I've learned the hard way. And it's just this idea of, like the first couple of times, that sucker punch or the gut punch or whatever you want to call it. It's just really like humbling and disappointing and saddening and just like, damn, I did all this work and now look what the universe would have ever thrown in my way or in my path. But what I've come to realize over the years is just this idea of just getting up quicker. Failure is just like that didn't work, like what's next now? And so talk to me a little bit about, internally, what's happening for you at that moment. And then what's the pivot you made?

Yeah. So on failure, I think, like the thing about the COVID whatever you want to call it, you know what I mean the shutdown or because a lot of people's lives pivoted when that happened want to call it you know what I mean the shutdown, or because a lot of people's lives pivoted when that happened, I actually didn't really view that as a failure because it was out of my control.

And so for COVID, it was like I said it was. I mean, it sucked. At that point, I had an in-person studio that I had built out and invested tons in and it was awesome and like, of course, everybody canceled their scheduled interviews because, first of all, they're supposed to be in person but, second of all, they were leading their organizations through crisis. So it was a weird time to do a, you know, a looking back.

But I would. I think, like everybody else, I was just kind of at home like all right, well, this is weird, but everybody else is going through it no-transcript of them and to ask what, how are things like? What do you need help with? And they were all asking me what I do with Philly who, and so that's kind of what dovetailed into Grow the Show. But, like I said, it really wasn't that existential failure on my end personally and it comes for all of us. So it did eventually come for me. But I'm grateful that COVID happened, because I love doing Grow the Show and I was also a little burnt out on Philly at that point.

So it actually came at a good time and there was a little bit of a sense of relief.

So talk to me about the idea and the inspiration for Grow the Show then, and what were you looking to do and maybe what other shows you were inspired by, maybe. What were you looking to do and maybe what other shows you were inspired by, maybe what were you looking to do different and how that's grown since then.

Yeah, yeah. So Grow. The Show actually launched as a program, not as a podcast at first and it was the idea was I spent a couple weeks just getting on Zooms with podcasters to help them out. And what's funny is at the time I thought that I almost like forgot the lessons that I had learned and I thought that what every podcaster needed to do was learn how to make a better show, learn how to be a better interviewer, Because, like I said before, quality is hugely important.

You've got to have a good show. And so I was talking to a mentor of mine and I was like, hey, I think I'm going to launch a business or a podcast about how to teach podcasters how to be better interviewers, because if we can just all make better shows, they'll grow more. And I remember he was like, okay, that's a cool idea, but do me a favor, before you buy the domain, before you spend six months building a course and everything like that, go talk to 30 podcasters and don't ask them if they need help with interviewing, ask them what they need help with.

I said, okay, fine, whatever, I'll humor you. And so I did that and I got on 30 calls with podcasters and every single one of them.

I just I'm struggling with growth and I don't know how to monetize Every single one of them. All of them big shows, little shows, corporate shows, independent shows, all of them. So I was like, oh, they're doing the same thing that I did. I'm like, oh, they're struggling with the same thing that I struggled with, which is they're putting out a show and they don't realize that marketing a show and monetizing a show is a skill to be learned. So with that, I was like, oh, let me start helping them.

I started helping a bunch, just kind of off the side of my desk, and with time I was like I think this could be something big. I think I could create a business that helps podcasters grow. So I remember I was thinking about kind of noodling around with this idea a little bit, and I was taking a shower one day after working out in my basement gym because it was still locked down, and I was like grow the show, grow the show. That rhymes, oh my God. I jumped out of the shower, went to my computer, see if the domain was available and it was. So I launched it as a coaching program and I had just been exposed to the online world of coaching programs and I was like, wow, I could do this for podcasting and launched it. We've got three clients right away and didn't launch the Grow the Show podcast until October of that year, so six months later. That solved a huge problem, because after three of my friends bought from me, I didn't understand sales.

I didn't understand nurturing there's so many more lessons to learn.

So I spent three months getting on discovery calls with literally 150 people.

None of them bought because I just didn't understand sales. I was just this random guy.

I would talk to them for 15 minutes and then ask if they would buy a $3,000 program. They're like what Pound sand? So then I launched the Grow the Show podcast and that is where the inflection point really happened. Once I applied my expertise in creating a great show and shared that and said hey, everybody listened to this and they're like. Oh wow, this is good. I want to hear more.

Obviously imagine the. The lessons learned about interviewing from Philly show helped a lot with Grow the Show.

Oh, a hundred percent. And I launched the Grow the Show podcast, very much like the Philly show where it was very heavily edited. It was like NPR style. It was like scored, like telling stories and stuff. With time and with iteration what I learned was that people just wanted the tactics. They really weren't as interested in the grandiose storytelling of the background of the person that I brought on right. So different show. So I learned that through getting listener feedback. But it was what I would really learn was that the interviewing helped. Interview Like this is just asking somebody about their life Like that's it.

And if the stuff that it tells me indicates that they might want or need what I have, I'll tell them about it. And I was like whoa. So yet another experience that in the end like wound up being super valuable later for business that I never could have guessed.

How did the conversations go, or how did they change, from the time you started Grow the Show to where it is now the conversation you're having on Grow the Show with folks.

On Grow the Show. Yeah, so I mean, what I learned was I was originally in the original version of the podcast. The first half of the episode would be almost like a mini Philly who, like a mini storytelling of the entrepreneur's background. Because I would bring them on because either they had a successful show or they were an expert in a piece of growing a show, like it might be someone who's really good at landing sponsors or whatever. So I would have them on and I would like the first half would be like a 15 to 30 minute like audio oral history of their background and how they got to where they are, and then the second half they'd be sharing tactics.

What's different now is that I pretty much only ask about background when it directly relates to the tactics they're about to share on the show. Because what I learned is that the listener really does not care what college they went to or you know what I mean. They're just not interested in their first initial business. That has nothing to do with this one. They just want to know. But it is helpful if the guest is sharing like a trial or tribulation that eventually translated into the lesson or how they learned or earned the tactics they're about to share, because a lot of times the listener hears themselves in that moment.

Right. So now it's. I'm really only asking my guest about their background If I know that their background is where my listener is now, so that my listener can be like, oh, that's where I'm at and they have what I want, so I should listen to what they have to say. So that's really the only time that I go into background now, and sometimes I just don't even do it or I just say like, hey, this person is an expert at this. I'm having them on because this, that's the other thing.

Let's get to it and people love it, people appreciate that. And then I want to get into something you teased out there because I'd be remiss if I didn't ask. So let's talk about the big elephant in the room, like the moment. For you, that was the bigger failure than, obviously, closing down Philly Show.

Yeah. So the Philly Show, it went on pause when COVID hit and really like indefinitely started doing Grow the Show and I just didn't bring Philly who back. Like I just did, grow the Show started working. I was like I want to do this. There was a brief moment in 2021 where I just wanted to bring it back and I was like I miss doing it. So I brought it back and was trying to do both shows Grow the Show and Philly who. And then, within like four weeks, I was like no way like this cannot be done.

The Show is two years old and it is growing very fast. The program was growing so fast we were getting 20 new clients a week and it's a high ticket program, and so my business was doing more than six figures a month. And the mistake that I made like I had a banner month in June of 22. And the analogy that I use is like I had, let's say, I just squat 150 at the gym, like, ah, I hit 150 pounds. Basically, in business terms, I said, let me see if I could do 500.

So all in one month I completely revamped the product. So it went from a group coaching program to Grow the Show Accelerator, which was my flagship offer. It went from a group coaching program to one-on-one coaching. So I added one-on-one coaches. I added asynchronous Slack support, which didn't exist before. I added an in-house production, so when you join the program we handle all of your production audio video, show notes, clips, all that stuff. So I built an in-house production agency to just be included with this offer. I hired a setting team for the first time. I had never had appointment setters before and I also hired an operations person for the first time. Basically on the same day I had all the employees start on the same day.

And what I didn't understand was you want to kind of slowly, slowly, like software iterate, like something that I did when I was a software developer. You change one little thing and then you update it, and then you change one little thing and you do a software update. Well, I instead went for like a complete version update, right Like from 2.0 to 3.0, without doing any testing, and I found myself virtually overnight, from having three direct reports to 10. Immense complexity. I raised the price a little bit, but also I did this big public price raise because I was like, hey, grow the show. 3.0 is here, so get in now, because the price is going to go up. You pay the old price, you get the new thing. That cleared up my pipeline. So everyone that was on the fence- was now gone.

So all in one month, all this new complexity, a bunch of new employees in roles that I had never managed before. I'd never owned a production agency at that scale. What's funny is that the production agency actually is the part that went the best, because I hired two people to build it and they did a fantastic job. But another mistake that I made was I just said it's included for the three months of the program and it's unlimited Big mistake. There was no parameters and what I didn't get was that a lot of people were joining the program and they would get their three months of included production, but their business was not yet at a place where they could afford to continue after the three months, so they were all canceling. So three months after I launched this agency, we had 50 full production clients and none of them renewed.

So I just had this production agency with, I think, six to eight employees and freelancers and it wasn't generating any revenue because, like I said, I just made a bunch of mistakes. Because I made all these mistakes that I now, through tons of reflection, looking back, did that wrong, did that wrong all in one month. So it started to really come to a head in October of 22, where I had to lay off the whole production agency. I actually divested it to one of the guys who built it. I said look, let me out of your contract. Take the clients, take the employees, take the systems, take it all. Just take it off my plate, because it's so much else going on, and so they did, and that agency is still crushing it.

I took a lot of pride in being the cool boss and like I'm not, laying anybody off and really like I should have laid folks off earlier.

I like I kept them on for too long because I just really didn't want to lay them off, right? I didn't. I wanted to be a good boss, I don't want to fire these people because of my own mistakes, and yet it just made things worse by delaying the inevitable. Still friends with all of them, I think I'm pretty sure we're all still on good terms, but it kicked me back into solopreneur mode.

The good news is I was able to spend last year slow down like just because I literally just took a step back. It was just me. I shrank my client base to where I could handle it myself and really I kind of just chilled for a minute. I was like, let me just service these folks and put out some episodes and take a breath. And that's what I've done. And so now I'm back for round two, but going back to the lesson that you shared.

I mean that lesson, just like I was in the dumps man, like I was in rough shape, like man, I guess I couldn't handle it. I guess I had hit seven figures, but I guess that I just got past what I'm capable of, right, and maybe I'm just not a seven figure entrepreneur and all these like doubts and all that stuff. And then you get into, like you find it difficult to start taking action. So for a while I kind of just got paralyzed because I was scared to make another mistake again. And to your point now I'm like okay, next time something like that happens, let's not take a year to get back up. It's exactly what you said before.

It's like learn how to get up faster.

Well, thank you for sharing that and being so open and vulnerable, because I know these are not easy, because the challenge and I think what's happening I think that this service that we're seeing is that folks see things from the outside and it's just like with anything that's social media Instagram, facebook, whatever you want to call it the allure of being a seven figure entrepreneur.

It's not the seven figures that matters, it's what you take home and put in your bank and the profit, right, and no one talks about that.

You know there's seven figure entrepreneurs that are taking home like a thousand bucks a month because that's all they have left after they spent and paid their teams and paid all their marketing budgets, and so I think it's more important to talk about this and so that people understand like the real stuff that's going on behind the scenes and also as entrepreneurs itself, or anyone who's looking to move down that path, to not feel like it's kind of like I got to do what other people are doing or I got to do what other people say they're doing, cause that's really what we're trying to do, like we're trying to do like mimic something and it's not the reality. It's not what's happening and you know, as I was just getting cold sweats hearing some of the parts of that story, especially around the agency, and just like managing 50 clients and we don't have that many in our agency, and then even with the ones we have, we've had ups and downs and just imagine 50 different clients with 50 different requests and personalities and stuff like that.

Who are all trying to just like get as much out of their free trial as possible, because they know they're not, it was brutal.

What I'll say, though, is like I think I still like, because I got that. Like while this was happening, I was like, man, this is something that I know, it like people should know about, but at the same time, like when you sell a coaching business, it's kind of hard to be like, hey, everyone, I'm like really struggling right now and I really don't know what I'm doing, and but you should hire me to coach you.

So, like I found this place where I was like I would love to share this and I absolutely plan to share it, absolutely Get it out there so that other people because it was true, like I look around at social media and content and I'm like I'm the only, I'm clearly the only one who's ever made a mistake, but that's obviously not true but still, I wasn't ready to share it publicly because I didn't want to alienate my current clients and be like hey, you know this company you just bought this thing from, it's just imploded.

And I also didn't want to. I needed to sell more clients on coaching and I'm a damn good podcast growth coach and I'm a pretty good business coach too. So the clients that I've worked with over the past year, one-on-one, have gotten incredible results. So I was like, let me just keep this. So I was debating whether to share it, but here's the key, here's what I learned I didn't share it publicly, and I probably until now, and I knew that I'm doing a few podcast guest appearances, so that I knew that it was going to happen, I know.

And if you've heard past episodes, you know at some point I get into it folks.

Right. I was like I have a feeling that it's going to be this one, but I'll just wrap it up by saying the mistake that I made was that I didn't tell anybody in my life. I told my girlfriend knew. That was it. And that was probably the biggest mistake that I made total, including all of the business mistakes, because it wasn't until like eight months into this ordeal that I actually started talking with other entrepreneurs and sharing with them what happened, and every single one of them was like oh yeah, yeah, we're doing horrible this year. Or like, oh yeah. I remember when I did and I'm like wait a minute.

I didn't know that and sure enough literally everybody's had issues like this. So it wasn't until I started having a small inner circle of other entrepreneurs that are at a similar level, who were talking me through it, helping me through it, sharing their war stories. That was when things started to turn around. So that was. The mistake that I made was that I didn't tell anybody.

I don't know if I would have shared it publicly but either way, that was a huge thing.

Well, I mean it's kind of connected to this idea of imposter syndrome and people like feeling like I'm not as good enough with that person, but also there's a flip side or something related to that, where people feel like I can't admit failure because and it shows that and I think to your point you discovered is that we've all been there and we're doing a disservice by not communicating that, by pretending that we've got everything under control and everything's going to be working out for us, and so I appreciate you being again, like I said, sharing that story, being vulnerable and letting people know that it's not all rosy, especially for people. That may be where you were years ago, trying to get through this entrepreneurial thing or at an inflection point where they want to grow the thing and just anything we can share that are lessons learned. I hope there's a trend now I've been seeing it with a couple of folks that I follow just to be more real and to share like the stuff that we don't see on the posts, on the reels, on the stories, like to share the stuff that's really happening. We're all human beings and we're all like doing the best we can and sometimes we feel like the pressure to perform at a level that's not reasonable, that's you know it's not realistic.

And people are getting burned out, people are having mental health issues, and to not be able to communicate what's going on at a very important time in your life and just being able to share with one person I mean, I've been there. I know what it's like. You wake up, you can't go to sleep and you wake up and all you can think about from the moment your eyes open is like your business, or in like what's going wrong or how to fix something. Or you got to, you're checking your email, like the first thing you grab in the morning is your phone, and it's not healthy.

It's not healthy you know, and so I appreciate you, kevin.

But you know, obviously, you know you definitely have had success. You've demonstrated success with the show, with your both your shows, with the program, with the coaching. I do want to give you a couple some time here, cause you do have a summit coming up that I want you to let more folks know about and we'll make sure we accelerate the production of this episode to get it out in time for folks. So you want to take a little bit of time to let the listener and the viewer know what you're working on.

Yeah, so, despite the fact that, I ran into some huge issues last year. What's been true the whole time is that I know how to grow shows. I know how to grow a podcast. That part is unchanged, and so what I'm really and what's also cool is that when the business fell apart, it gave me the opportunity to really be like okay, how am I going to rebuild this in a way that works even better and that is a better product, a better business? It's very hard to do when you've got 10 employees and things are going crazy.

It's hard to make things really, really focused on how to make a great product. So for the past four months, I've been developing a brand new product and a brand new event, and so I'm going to be doing the first one on April 1st through the 5th. It's called Grow the Show Live. It's my first remote summit. One thing that I've learned is that immersion is the best way to learn. It's my favorite way to learn is where you can really dive deep with something.

Awesome. Thank you so much, kevin. Interesting to get feedback from people that have heard the show, found out about the show. Obviously from a branding perspective. You know the show has been around. I'm heading into year 10 next month, so it's pretty wild to think about. But I'm really grateful for these conversations because they allow me to really see what's happening in the podcast community and share those stories and over the years I mean it feels like the episodes are becoming more like podcast therapy for folks because we're just kind of sharing.

Then it was my idea in the beginning I said a little bit of acting back in the day, so I was inspired by Inside the Actor's Studio and it's like you get an hour with an actor. You get to peek behind the scenes and I think to your point, like we get to peek behind the microphone of these podcasters and I push people to be vulnerable, because I know it's what people resonate with and can connect with, because we're at a human level. We can see Kevin's website, we can see Kevin's programs, we can listen to his podcast, but to hear him and for you to be vulnerable and share what's really happening, that's when the real human connection happens and it's what we need more of in this world. So I appreciate you for coming on and for sharing your story with our listeners.

Yeah, thanks for the therapy session. I'll send you my billing address.

Sounds good, so anywhere else you want to send folks. We've got that link growtheshowlivecom forward slash, Harry, yeah.

Yeah, well, if you don't want to do the live event, you could just. There's two things. Number one I've got an email course. It's called the 12 days of podcast growth. 12 days of podcast growth.