Welcome to the Grow My Podcast Show
May 16, 2023

60. Finding Growth in Entrepreneurship Challenges in Podcasting with Alex Sanfilippo

60. Finding Growth in Entrepreneurship Challenges in Podcasting with Alex Sanfilippo

Join my conversation with fellow podcasting software founder, and dear friend, Alex Sanfilippo for a candid discussion about the pressures, the stresses and the fulfillment that comes with building game changing software experiences to serve independent podcasters and change their lives.

If we feel stress, pressure, any of that, it's because we care. And that's a good thing.- Alex Sanfilippo  

Alex Sanfilippo, the mastermind behind Podmatch, and founder of PodPros, is passionate about making a difference in the podcasting world. Alex's focus on community-driven entrepreneurship and his willingness to share his experience and wisdom make him a go-to expert for podcasters seeking to expand their reach and impact.

 In this episode, you will be able to:

  • Master effective strategies to handle the pressures of entrepreneurship and maintain a healthy mindset.
  • Learn the power of community-driven entrepreneurship to achieve greater success and long-term growth.
  • Discover the significance of tracking key performance indicators whilst recognizing non-monetary accomplishments.


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My Co-Founders, Ash Clarke and Bona Rai, join me in this candid conversation about the launch of Version 2 of our AI-powered software, Capsho. We reflect on the overwhelming pressure from unexpected delays and share our key learnings from the experience of building and shipping a whole new product in under 8 weeks.

Building an Authentic Brand for your podcast with Mark Asquith

You will learn Mark’s unconventional audience attraction and growth strategy which he has honed over 10 years of podcasting himself and working with thousands of podcasters.

Resources mentioned in this episode 

💻 Try Capsho free for 2 episodes  here

Capsho is an AI-powered podcast marketing content writer that creates an episode title, description, podcast website content, social media captions, emails, blog posts, LinkedIn article and YouTube description AND curates a selection of quotes from your episode. All with a simple upload of your episode audio or video file.

🤝 You can connect with Alex  here

💬 Leave me a message  here

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Connect with Deirdre:  Instagram  | Facebook | YouTube | Twitter | LinkedIn


00:00:00 Many of you might know Alex SanFilippo, who is the founder of Podmatch. And if you don't, you should know him. Definitely go check out what he does over at Pod Pros. But he has become got in the last not even a year. He has become such a great friend and a mentor and a peer of mine.

00:00:18 And I was really funny. We were on this call, and he just asked me this one question, and I just started there just, like, spilling my guts out. And so I wanted to actually share that call with you that midway. I was like, oh, this is just going to become a podcast episode. So this is a completely unedited, uncensored conversation between two tech co founders, Alex and myself, about how we struggle with some of these things, about how entrepreneurship has been treating us.

00:00:52 And I hope that anyone listening to this, whether you're an entrepreneur in anything, an expert based business, like a coach, a consultant, service provider, especially with a podcast, that some of the messages and some of the things that we talk through here will help you. My name is Deirdre Shen. I'm the CEO and co founder of Capsho, and this is The Grow My Podcast show. So, Deirdre, how are you? And what I mean by that is I'm actually wondering how you are as a founder in the podcasting space.

00:01:20 Like, I'm just wondering how you're doing. Yeah, I think in this exact moment in time, Alex, I'm battling with really good things, and I'm always grateful for the really good things, but I can't help but have some of them more negative things, like get me down. So right now, for example, great thing is that we have a ton of subscribers, and the number of Captchovians that we have on Capsho is growing, which is amazing. The bad thing is that we have we're just constantly hitting server overload issues, errors, and it's a nightmare. And I think I take this stuff so personally because I want to be building the best thing ever for podcasters, and I feel like I'm letting everyone down, if that makes sense.

00:02:07 So that's how I'm feeling. Well, I like that you feel that way, because it shows that you care. That's how I am, too. And I imagine you lose sleep at night, and we can get into that in a second, but you're doing that because you care. If you didn't care, you'd be like, numbers are climbing.

00:02:25 Sometimes doesn't work, but whatever, we'll get there. No, it actually bothers you that sometimes things like servers go down or lag. Here's the thing. Hold on. Like a side rant here, and I'm sorry, I'll turn it back.

00:02:37 This is not why we're here. But I got to give this side rant, you're literally paving the future of the Internet. Like AI is the future of the Internet. Servers don't know what to do with that yet. Let's just be real the tech of what you're building versus what's available is outpacing it it's like when YouTube got started, like, streaming video was a new thing, and it didn't work on half the computers.

00:02:56 Right. It was one of those things the Internet had to catch up with what was being created, the innovation. So you're at the forefront of that, so you're driving things forward for people like me. My software runs more smooth on servers in the future because I'm not forcing things to get better, but you're actually paving the future. So I know it probably sucks and it's probably scary, and because you care about people so much that you serve, it bothers you.

00:03:20 But at the same time, I think that a lot more people probably understand that you are actually paving the future for all of us. And that's the requirement of it, like, it's disrupting. Right. So there's some friction that's going to happen. Does that make sense?

00:03:33 I don't mean to take that too deep, but that's my very first thought when you said that. Yeah, and I appreciate that because I actually wanted to ask you, what has your experience been, especially when you first started? Because I think the thing that I lose sight of sometimes is I see, and this happens to a lot of entrepreneurs, I believe, is we all have that goal that we want to get to, or we see the person in the future that we're like, yes, that's who we want to be. And we think that we can be them now, or we can be that now, or our business will be that now. And it's just I'm finding that's definitely not true for us, no matter how much I will it into existence.

00:04:09 So I'd love to hear from you. Even when you first started, compared to where you guys are now, what did that look like? Yeah, first off, I lost a lot more sleep than I do now. Not that I don't lose sleep still, because I do, but when we first started, we grew faster than my wildest expectations, and I am very thankful for that because I'm like, an overly ambitious entrepreneur when it comes to like, oh, yeah, we'll be here in no time. And it's like, Dude, that's a five year plan.

00:04:33 You said one month. That's kind of like I've brought it in a little bit, but initially, my wildest dreams, we outpaced by, like, ten X. Wow. And we had major server issues. We didn't build the platform.

00:04:46 We built it to test this idea. And overnight it went from testing the idea to being massive. And yeah, it caused all kinds of problems. We were getting emails today, hey, this isn't working, this isn't working. And in my head, I thought every single person was reaching out, was angry.

00:04:59 Like, that's just where it was. I'm like, they're so mad, they're so angry. What I didn't realize until I started getting on calls with these individuals is they weren't actually mad at me. They just cared, and they wanted me to know. But they said, hey, listen, what you're doing doesn't exist.

00:05:12 You're paving a better future for podcasters to find guests and vice versa. And so, of course, there's some people that just you know how it is. Some people are just if you're already an angry person, you're just going to spread that anger through everything, right? But you to let that roll off as much as you can. I mean, we're human, so it is going to hurt no matter what, right?

00:05:29 But at the end of the day, when I start getting these calls, people are like, hey, I believe in you. I'm in your corner. It hasn't worked in two weeks, and I'm paying you, right? And so for me, it was a lot of lost sleep. Honestly, I lost hair because of it.

00:05:43 It was really because I cared. I'm still, to this day, not like a super driven by money entrepreneur, which I know makes me kind of strange in the space, but in general, I just care to deliver the promise I made for people that I care about. And so, yeah, early on, it was a ton of lost sleep. It was a ton of stress and pressure of me feeling like, man, am I really making a difference? Am I really going to drive this thing forward?

00:06:05 And we grew really fast, and now I feel like we have a crumbling foundation. What do I do if it doesn't work? And now all these people just don't have a solution anymore, and they're back to square one, where they were before I started. All these things came up, and I guess the best piece of advice I was given Deirdre that I still hold on to today was somebody used the example of us being an entrepreneur and our businesses being like a caterpillar that's turning into a butterfly. And so they gave this real life story that they experienced where they said that their kid found a cocoon outside, and they decided, all kids like, wow, I found it.

00:06:41 I want to see it turn into a butterfly. So they brought it inside, put it in a jar or whatever, and then the day happened when it started its transformation, for lack of better term, obviously, I don't know nature, but whatever happens to make that caterpillar turn into a butterfly, right? That time came up, and so the kids watching it, but the parent that I was talking to said it looked so painful, and this thing just struggled its way through. And finally they opened the jar and helped it get out. And what ended up happening was that that butterfly actually wasn't able to fly as a result.

00:07:10 And when they started looking at it and finding out why, there must have been something wrong with it. No, actually, in order to develop the muscles needed to actually fly and to truly become a butterfly, it has to go through all that stress and pressure or it will never be able to fully develop into what it needs to be. And that person told me, he's like, Alex, that is you and that is your business. You have to go through some of these struggles and people are going to have to see you go through that in order for you to come out the other side. Something that can actually truly serve them to the highest capacity.

00:07:36 Indeed. I don't know if that helps you at all, but I still hold on to that story. And remember that. Because here I am, years later. And I wish I could tell you that all that sleepless nights go away and the pressure or the stress of feeling like you're not delivering I wish I could tell that goes away, but it doesn't.

00:07:51 We just have to get better and remember the vision of why we're doing this to serve people. And if we feel stress, pressure, any of that, it's because we care. And that's a good thing. It means we haven't lost sight of our true vision to serve others. As an entrepreneur, I'm probably rambling here a little bit.

00:08:06 I don't mean to, but that's where I'm at and that's helped me a bit. If I can just, again, be fully transparent with you. Yeah, that's super helpful. And I'm actually like tearing up a little. I think it's like hitting I think we're just running so hard right now.

00:08:21 It's like issue after issue after issue. And I feel so bad for our captivians because they're caught up in this. They've been the best, the best community, and they don't deserve to not have something that works amazingly. But it is useful, I think, to know that and hopefully to know that we're not alone in this journey. To know that, yeah, in a way, it's not my capture, it's not Bonners or Ashes or whoever.

00:08:50 It's actually like, everyone. This is something that belongs to everyone. And I think that's also the mindset shift. And when you talk about the struggles and stuff, it's so easy to get into my own head about it, to be like, well, it's absolutely my fault, which I do take extreme accountability of, but also I should be leaning on others to actually help capture, come out of the cocoon and be a beautiful butterfly. Yeah, I think you put a lot of pressure on yourself, right?

00:09:22 100%. Yeah, me too. And at the end of the day, we both believe you and I are very similar as entrepreneurs. We are a community driven entrepreneur. Neither of us got in this to say, I'm going to buy a Ferrari and my house on the beach and I'm going to be rich and famous.

00:09:38 And that's never been either of our ideas behind this. We didn't get into it for that reason. And although most people that get into entrepreneurship, that's the underlying thing that they all want, right? We got in this because we believe in the vehicle that we're creating, that it's going to truly serve a community that in turn is going to leverage that to serve the world. Like you and I are the same with that.

00:09:59 And what you said was so beautiful. It's not just yours. It's this community that, again, is going out and ultimately making the world a better place by serving. And I'm preaching to the converted here, which happens to be myself. I put too much pressure on myself every single day.

00:10:14 And I have multiple times a day, I literally have it written down. I'm holding it right now, this journal, to stop and take some deep breaths, because I know that relieves stress and lowers your blood pressure, and I have to do that, and I'm, like, a super stressed guy, but I just put all the pressure back on myself. When in reality, there's a whole community that feels not maybe not equal buy in, but they feel some sense of buy in, and they will forgive us along the way. Because together we're paving what we think is a better future. And again, I'm preaching to myself when I say it because I need to hear it.

00:10:45 I need to take those deep breaths every single day because it's tough being in this seat because, again, you feel like, well, I'm at the helm of this ship. There might be 100 of us on it, but at the end of the day, if we run a ground or head around direction, that is on me. And that is true to an extent, but remembering that everyone on there is willing to take a shift, more or less, right, to do something along the way should relieve us a little bit, I like to think. Well, definitely, Alex, I'm in your corner, right? I'll take a shift for you for sure now, whether or not we'll be able to maneuver around the iceberg.

00:11:22 Maybe I shouldn't have used that example too soon. No, but thank you. That's a good reminder, actually, of how to keep things in perspective and what's actually important. Now, do you want to make this, like, about me? I know I did.

00:11:38 I just did, because everyone and I think we're just going to turn this into a podcast episode as well. But, like, what would your advice because everyone listening to this is an entrepreneur in some aspect. They may not be a tech co founder or founder, but they're an entrepreneur in some way. So if we step back and we kind of go in these moments of extreme doubt and extreme pressure and just feeling like we're never going to it feels like we can't get out of this and that we are. Impacting the people that we are here to serve and that we want to be making the lives that we want to be making better in some way.

00:12:17 And I know that you shared some really great stories and some things, but do you have like, I don't know, a mantra? Do you have something that you go to all the time that helps you through these moments? And then do you have even a story of when you've been in this and when you come out of it and almost the community rallying around you because of that? I don't know. I totally put you on the spot.

00:12:38 I don't know if you have any of those. No, I do. Well, first off, having your own little network around you is super important. A lot of my closest friends literally probably don't know what I do. They're like, I think he does something on radio or something on the internet, right?

00:12:53 And that's okay. I'm fine with that. So having something that pulls you away from it is super healthy. But also for me, having something inside of my space, we're part of the same mastermind together. We're into the same masterminds.

00:13:06 And because of that, it just helps, you know, you're not alone. And that is so important. Beyond those two things, which I think we all need, my team and I, it's weird. And you know this. If you get one bad remark or email or someone reaches out, it doesn't matter if you had 100 people say something nice that day, all that you can think about is the one negative.

00:13:27 And if there's one thing I could change about me as a person, I wish it could flip if ten people said one mean things about me, but there was one nice I'd love to more be that way. I immediately go back to Dumb and Dumber, where he goes, so you're saying there's a chance if anyone remembers that. Right, there's no chance. But you're saying there's like one if it was 1 million, there's still that little chance. I would like to be that optimistic about it.

00:13:50 So what me and the team have done is whenever we're feeling down, we have an internal slack channel. That's what we use for our internal, like, just quick communication, which everyone's pretty familiar with, right? We have something called our happy news channel. And when somebody says something that is just like, oh, this was so freaking nice, we just posted in there. And so for me, sometimes when I get down, I literally go to that channel, I'll just get caught up on it and it's like, nicest remark after nicest remark, and some person just was being really mean, right?

00:14:16 And anyway, so that helps out a lot. But if I could think of a specific story and then I'll share what keeps me going, right? Like what keeps me moving, the specific story would be I talked to somebody, this was probably a year ago, and they just felt like totally lost in their business from a lead perspective. And so they were a podcast guest and a podcast host and they were actually really talented, what they do, but they were awful at sales and marketing. Just terrible.

00:14:41 I'm not trying to be rude. Like if they heard this, they'd be like, yes, that's me. But they turned it around. And the way they actually did that was through the vehicle of podcasting. And so this person talked about feeling depressed, stressed when we had our conversation, like, just like, I just felt like I was going to fail and was for sure going to happen.

00:14:56 And then somebody random in a Facebook group mentioned, hey, I just found this thing called Podmatch. And this person said, I joined as a guest, as a host. And like a year later, they literally came out of a terrible situation into now, like, thriving more than they ever had in business. Now, that wasn't us. We were just the vehicle to get them there.

00:15:14 It was their expertise that obviously made that happen. But like, hearing that, I was like, man, this person and their family's life was completely changed because of the vehicle that we gave them to get there. And so that leads to what actually keeps me going every day. I try not to look at the up and down times of servers and the MRR. Even so monthly reoccurring revenue, like looking at that spike and drop and be like, why are ten people leaving today?

00:15:38 Right? I try to look at that stuff instead. Each of the little products that we have, I do my best to look at. What is the ideal outcome for somebody who's using this. Going back to that example, that person whose life had changed, that happened through podcast bookings on Podmatch specifically.

00:15:51 So I think of that one, what I look at is the total number of podcast interviews that have happened and episodes have been released as a result. When that number is climbing, I can look at that. I say, you know what, despite all the other crap that might be happening alongside, if that number is climbing someone's life, like, this person I just talked about is being changed and being influenced in a positive way. And so I have to just hold on to that. And so for each of the products, I have a non monetary metric that is my primary tracking mechanism.

00:16:18 So, like, podcast. SOP it's how many episodes have been completed by podcast hosts? And on Pod Lottery, how many reviews have been left on podcast? Not even how many have been won? How many have been actually left on other podcasts?

00:16:29 Oh wow, we've helped 10,000 podcasters get additional reviews on their podcast. That's amazing, right? Like, those are the different things that I have to go to. And I think that the more we pull away the actual business of it and look at the end result that we desire someone to have, the better it keeps our mindset and the healthier it makes us as people saying, you know, what we're helping somebody do what they've signed up to do in the first place. I can sleep well at night knowing that I went on a mini rant there.

00:16:53 I hope that was helpful. Very helpful. I mean, A, I'm going to start that slack channel happy moments. I'm totally going to do that. And yeah, I think it's just even when you say that, I feel like when I take that step back, because this is the funny thing that happens, right?

00:17:09 Whenever we start a business, we always have that in mind. It's like, yes, I'm going to help this particular person do this particular thing, and it's such a great outcome. But then the more that the business goes on and you lose sight of that a lot of times, I think, because you get buried in the metrics and you get buried in all the things that people tell you that you need to be tracking, and that the important. And I think it kind of feels like the pressure is released a little bit because it's like, as long as we can stay core to what it is that we had set out to do and the people that we help, we set out to serve, then these are hiccups. And it sucks that these hiccups are happening still, but it's a moment in time.

00:17:49 We will get past this. And I think that's what we need to be constantly looking at, for sure. This reminds me, going back to the community side of it and stuff, people are nicer than you, and I think often, because again, we get that one person in that both our businesses, thankfully, have grown a lot, but we have enough that every day you probably hear something negative. It just happens now, but it's still only 1%. When you have ten people using your software, 1%, they're only going to reach out once a quarter, once a month, so it doesn't feel like much, right?

00:18:17 But then when it grows, that 1% turns into up to multiple times per day. And you're like, I'm not doing a good job anymore. But the end of the day, that's not the true community that you've built. And I love this story. There was a really big company.

00:18:30 I don't want them to like anyway, I'll just leave them nameless, right, that I had subscribed their email, and they had a really unfortunate typo in one of their emails that went out to hundreds of thousands of people that I was like, OOH, I happened to talk to their CEO not long afterwards. He goes, you know what? He goes, Weirdly enough, he goes, that was the email we got the most positive feedback from. And people saying, you all do such a great job, and responding in a positive way because they showed the human element of not being perfect. And they did apologize, like, we're so sorry, we didn't mean about to go out.

00:18:57 And people were like, wow, that was really cool. Everything you do is so polished and perfect all the time. It was just cool to see that you're like me and make mistakes. And so I think for you and me, we have to also release the pressure of having I don't think either of us have this I've never gotten this vibe from you of we've got it all together and most entrepreneurs, they want to look like, I've got this thing dialed in. It's perfect.

00:19:17 You're never going to find a problem with it. But if we just straight up say whoops totally made a mistake, right, like, didn't mean to do that, but hey, we're all in this together. Let's try something else. And as long as we can bring people back together again, the 1% we just got up the outlier, that's rude. Mean, we just got to push them aside in our minds, right, and stick with the 99 that are saying, yeah, we're in this together, that was maybe not our best decision as a group, but let's keep on going, right, and just own it.

00:19:42 And for me, ever since seeing that email that was years ago, I have multiple times apologized for small updates that didn't ship as proper as they should, right. They actually caused problems or typos I've had or things that just didn't work. And along the way I've just been fully transparent with it. And I'm telling you what, people have appreciated that more than better software, weirdly enough, right. They would rather just be like, yeah, Alex is another one of us than, oh, yeah, everything he does is perfect.

00:20:08 I'm not saying you're off the hook for not trying to perform at an excellence, a level of excellence. Right. I'm not saying that we need to always do that, but at the end of the day, we are human. We're not AI like you build. So if we do something that's not perfect, it's okay.

00:20:21 And I think as long as we are open about that, to me that's alleviated a lot of stress. Again, not all of it. I'm on this journey with you, but that has helped a lot knowing, you know what, these people are actually my friends and they care. I love that. I feel like this would be the perfect moment to be like if you're an entrepreneur struggling with these issues, here's the hotline.

00:20:42 I don't have one. Support and help. 1800 entrepreneur. And people are like, I don't know how to spell it because I don't know how to spell it. So no one's going to call that number anyway.

00:20:49 We can say it exists. 1800 entrepreneur. Call it every day. No, but definitely reach out. Reach out to me.

00:20:54 Reach out to Alex. We are here for you. Honestly, that's what we do day in and day out. So. Thank you, Alex.

00:21:01 This just kind of turned from a chat into a podcast episode. Unexpected, but here we are. I'm fine with that. And I don't know, is there anything that any call to action you would like to make? Call that this was literally just supposed to be a conversation of two co founders of companies venting about where we're at?

00:21:19 No, I don't have a call to action, but I think that just at the same point, everything we do has got to come from a place of service that's got to be our mindset. And at the end of the day, serving isn't always pretty. And I'll give an example that I'm going to steal from Seth Godin, one of his books, he talked about this. He talked about shipping creative work, and it was called The Practice. And the idea is, hey, just ship what you have.

00:21:39 Get it out there. Get your creative work in the world. Don't wait for perfection. And he uses really great example, and I'll make this really brief here, but he talked about this being my first day. I'll just put myself in the story.

00:21:49 My first day is a lifeguard of the beach, right? And so I sit there, I get to my quick training. I'm sitting there. I'm obviously nervous. It's my first day out there, and then my person who's training me walks away and they go to their own station, right?

00:21:58 And then, of course, someone in the water is drowning. My reaction, if we're just looking at how people treat the world of entrepreneurship, is to immediately divert and say, well, hold on a minute, I know you're drowning, but let me go get this guy who's been doing this for five years. He's way more equipped than I am. Hold on. Hold your breath as long as you can.

00:22:15 Don't die. Right? I'll go get him and I'll be right back. In real life, Deirdre, that would never happen. What you're going to do is, as ugly as it may look, you are going to go out there and you're going to do everything you can to save that person's life, even if he means breaking their arm by mistake, right?

00:22:28 You're going to get out there and you're going to do it. And so for all of us creators, whether you're a podcast or some sort of software founder, at the end of the day, if you don't send something, if you don't publish something, if you don't release something, it doesn't actually serve anybody. It only serves somebody once you've released it. And you know what? It may be ugly, it may not be your best work within the day.

00:22:47 Sitting in your head, sitting in a draft folder is not actually going to serve anybody. So it's in your best interest to get it out there, do your best, and then focus on continuous improvement as you go. So no call to action, but maybe some final words of wisdom, if you can call it that. But I just want to share that, because I think that that would be really valuable for. Many of us to hear, even as podcasters, 100%.

00:23:07 Even for me, that Was like, yeah, there's no courage, there's no accolades. You get nothing when you don't Put yourself out there with all the messiness and the things that go wrong and all of the yeah, you just have to be in it. You have to be in it. That's be the man or woman in the arena. Yeah.

00:23:27 Awesome. Great podcast episode. I love it.

Alex SanfilippoProfile Photo

Alex Sanfilippo

Alex Sanfilippo is an entrepreneur who is the CEO and founder of PodPros, a software company focused specifically on the podcasting industry. He is also a podcast host of the top-rated podcast called Podcasting Made Simple and a lead educator.