Ina Coveney: Hello, Alex! I am so happy!

Alex Sanfilippo: Hey, Ina! It’s great to be here. How are you doing today?

Ina Coveney: You know, I'm doing fantastic. I'm honored to be here as someone who listens to your show. This is like a dream come true to actually be here with you right now. So thank you for having me.

Alex Sanfilippo: That’s like the tallest compliment. I'm like, “You listen to my little show?”

Ina Coveney: You guys, listen. Alex is the authority in podcasting. So that is a really high compliment coming from you. Why don’t you tell everyone what you do and who you help right now?

Alex Sanfilippo: Sure! So what I do is, I run a series of projects in the podcasting space to help podcast guests and hosts go further. We might get into some of those today. But ultimately, what I’m here to do in this industry is help independent podcasters get their voices heard and elevated. Because when more podcasts are released, the world becomes a better place. That’s what I’m about.

Ina Coveney: But you didn’t start out in podcasting. It’s hard for anybody our age to have started there, right? I started back in 2012. When was your first podcast?

Alex Sanfilippo: I think you’ve got me beat. I believe mine was in 2014 or 2015. I don’t remember the exact year. It was terrible, by the way—that podcast has disappeared from the internet.

Ina Coveney: Okay, so let’s go back a bit because none of us really started out in podcasting. It’s something we kind of found. But before we get there, I’d love to hear a little bit about you. Like, little Alex. Where were you born? Where did you grow up?

Alex Sanfilippo: Yeah, I had a really fun childhood. I’m so thankful for that. First off, shout out to my parents, who gave me an amazing life. They built that foundation for me. So thank you, Mom and Dad—if you’re checking this out. I don’t think they know how to listen to a podcast, but that’s okay. I appreciate them.

Ina Coveney: So, where did you grow up?

Alex Sanfilippo: I grew up in Jacksonville, Florida, and that’s actually still where I live today. When I was young, my family wasn’t well-off. We lived in a one-bedroom apartment, and there were five of us crammed in there. But my dad, who was an entrepreneur and business owner, really built up his business. Eventually, we moved into a nice neighborhood with lots of kids. My childhood was spent just hanging out in the neighborhood, riding bikes, and having fun. It was an absolute blast.

Ina Coveney: So, you make it through school, and how do you decide what you want to do with your life? You graduate high school, and then what?

Alex Sanfilippo: Well, before high school, when I was 10, I started a little business. Have I ever told you that story?

Ina Coveney: No! But I think I’ve heard bits of it. Please tell us.

Alex Sanfilippo: When I was 10, just being a curious kid, I noticed that golfers in our neighborhood golf course would lose balls near the cart paths. One day, a golfer asked me what brand a ball was, and when I told him, he said, “I’ll give you $3 for it.” As a 10-year-old in the 90s, $3 was a lot. I could rent a movie at Blockbuster with that!
After that moment, my brother and I decided to start collecting golf balls from all the lakes around the course and sell them to golfers. We figured out the best times to approach golfers—when they’d lost enough balls to question if they’d make it through the game. It felt like my first big win as a kid.

Ina Coveney: That’s incredible! But then, real estate comes into your life. Is that before you graduate high school? How did that happen?

Alex Sanfilippo: Funny story. One of my dad’s friends was into technology and real estate. My dad told him, “Alex is pretty smart with computers,” so I ended up working in a technology startup for creating virtual tours of homes. This was long before things like Zillow had that feature. We were pioneering that tech. I had three editors and four photographers working for me, and I loved it. That experience taught me about managing a team and working remotely, which was unheard of back then.
By the time I was 18, I was ready to invest in real estate. I’d seen so much of it and was fascinated by its potential to build wealth.

Ina Coveney: And then 2008 happened. Hashtag 2008. What happened?

Alex Sanfilippo: Leading up to 2008, I’d built up this identity of being a successful entrepreneur. I was making good money, had a cool car, and was living the life I thought I wanted. But I also developed a bit of an entitled mindset, and my relationships became shallow and centered around money and status. Then, when the crash hit, it was like a rug was pulled out from under me. Overnight, I went from being one of the most well-off young adults I knew to being the most in debt.

Ina Coveney: I can’t even imagine what that was like. It sounds devastating. What helped you get through that?

Alex Sanfilippo: I was at my lowest. One day, I got a flyer in the mail for a young adults’ church service. It took me three weeks to work up the courage to go because I felt so ashamed of who I had become. But when I finally went, the people there loved me for who I was. That’s when I experienced a moment of clarity and faith. It changed everything for me. From that point forward, I decided to live a life of love and service, inspired by Jesus’s example.

Ina Coveney: Wow, Alex. That’s such a powerful story. Thank you for sharing that. It’s incredible how those moments can transform us.

Alex Sanfilippo: Thank you, Ina. It was a pivotal moment in my life, and I’m grateful for it.

Ina Coveney: So you’re working in aerospace for 15 years, rising through the ranks, and then you start to feel like it’s time to leave. What triggered that?

Alex Sanfilippo: There was a moment when one of my divisions saved 10.5% on the bottom line for the quarter. I was so excited! I thought, “This is huge.” I imagined walking into the CEO’s office and saying, “Did you see the numbers we just pulled off?”
When I told him, his response was, “Yeah, I saw it.” He didn’t even look excited. I leaned in, saying, “But we saved tenfold! We worked so hard to achieve this.” And he replied, “No, no, I know. It’s good. But the shareholders aren’t happy.”
I was stunned. I asked, “Why not?” He explained, “You didn’t tell them we were going to do that. If we’d communicated this earlier, we could’ve been selling stocks at a higher level. Now, it’s just a bonus for the people already involved. Don’t do that again. Let’s maintain the status quo and grow at the pace we’ve set with our shareholders.”
I walked out of that office, and although my office wasn’t far, it felt like I was walking for an hour. In my head, I kept thinking, “It’s time to go.”

Ina Coveney: Help me understand where podcasting came in. Did you start podcasting while you were still working, or was it after you left? And when you left, did you already know what you were going to do next?

Alex Sanfilippo: I tried a bunch of side hustles, but nothing stuck. Somewhere in there, I started a podcast. I wanted to talk to people who had successfully left their 9-to-5 jobs to pursue entrepreneurship full-time and figure out how they did it.
I positioned the conversations in a way that benefited the listener but also became free coaching for me to learn how to do what they did. Looking back, it was a smart move, but at the time, I was just trying to learn and grow.

Ina Coveney: So when you left your job, did you already have something solid lined up? Or did you just quit and think, “I’ll figure it out”?

Alex Sanfilippo: By the time I quit, I had PodMatch as a side hustle. Three weeks after it launched, it became clear that if I didn’t devote myself full-time to it, it wouldn’t grow the way it needed to.
But quitting wasn’t easy. It was one of the scariest conversations I’ve ever had, second only to asking my in-laws if I could marry their daughter. I had to talk to my wife, Alicia, about leaving my cushy job that made our lives simple and secure.

Ina Coveney: Let’s get into PodMatch. When did it officially launch?

Alex Sanfilippo: PodMatch officially launched in 2020, right after the world shut down. Timing was key, and honestly, that was completely out of my control.
I made a single post on LinkedIn announcing it. That post drove 38,000 people to the website overnight. For someone with a small following like mine, that was huge.
One well-known public speaker joined the platform, and he posted about it, saying, “Thank God I found this platform now that I’ve lost all my speaking gigs. I charge $100,000 for one-hour presentations, and now I can go on podcasts for free.”
That post brought in tons of podcasters and other speakers. Within three weeks, we had thousands of users, and we hadn’t spent a dime on ads.

Ina Coveney: That’s insane! Some people might think, “Okay, stabilize this and maybe sell it to a bigger company.” But what was your approach as PodMatch grew?

Alex Sanfilippo: My approach was to focus on serving our members, not users. I wanted to build a community, not just software. We’ve never run ads. Our growth has been entirely organic because we focus on serving the people who trust us.

Ina Coveney: You also launched PodLottery recently, which is free. Can you tell us about that and your meeting with Apple?

Alex Sanfilippo: PodLottery is a fun app that helps podcasters grow their reviews. Essentially, you leave reviews for other podcasts, and in return, you get entered into a lottery where others will review your podcast.
To make it work, I needed Apple’s buy-in. So, I went to an event in LA where I knew Apple engineers would be. I pitched the idea to a senior engineer, and at first, he wasn’t even making eye contact. But when I explained it, he turned to me and said, “That’s a really good idea.”
Within 20 minutes, I had access to everything I needed, including APIs to validate reviews and listens.

Let me continue with the rest!
Continuing from where we left off:

Ina Coveney: That’s incredible. What advice would you give to someone who struggles with confidence and feels like no one will listen to them?

Alex Sanfilippo: Courage means being afraid and doing what you have to do anyway. You don’t need to be at the top to help others; you just need to be one step ahead. Focus on helping one person take a step forward today.
Here’s something else I’ve learned: I was homeschooled all the way through school because I was dyslexic as a kid and struggled to read. I didn’t start reading well until I was 12. Even now, I have a specific way I write things because of how my brain works.
If I’m ever asked to write on a whiteboard in front of people, I’ll freeze. I’ve memorized everything I say when I speak on stage because I’m terrified of reading something aloud. These challenges never fully go away, but I’ve learned to focus on the value I can bring to someone else.
When I left my job, I was scared. Even on my last day, I kept asking myself, “What if I fail again? What if this doesn’t work?” Those doubts are normal. But I remind myself of two key things.
First, all I have to do is help someone take one step forward. It’s like climbing a mountain together. If I’m just one step ahead, I can reach out and pull someone up. I don’t have to be at the top shouting directions.
Second, I hold on to this belief: Courage isn’t the absence of fear; it’s being afraid and doing what you need to do anyway. If I can take one step forward with courage, I know it can make a difference for someone else.

Ina Coveney: That’s such powerful advice, Alex. What’s the biggest misconception people have about you as a successful entrepreneur?

Alex Sanfilippo: The biggest misconception is that I’m an overnight success. People see PodMatch and think everything I touch turns to gold.
But here’s the truth: I’ve failed countless times. Even before PodMatch, I spent years podcasting and trying side hustles that didn’t stick. When we launched PodMatch, I had already spent two years learning and experimenting. Success is about showing up consistently, learning from failures, and building over time.

Ina Coveney: For all the online coaches listening who are trying to grow profitable businesses, what’s one thing they should do today?

Alex Sanfilippo: Here’s what I want you to do in the next 24 hours.
Grab a piece of paper and a pen. Turn off all your tech. Write down why you’re doing what you do. What’s the big picture? Who are you serving? Get granular.
Then, write down the single most important thing you can do today to move the needle forward. Don’t focus on your to-do list or admin tasks—identify the one action that makes the biggest impact. Then go do it.

Ina Coveney: I love that. I think I’m going to do that today!

Alex Sanfilippo: That’s awesome, Ina!

Ina Coveney: Alex, you are the man. I love every time we get to talk, and I’m so happy to have been able to share your story on this podcast. Can you please tell everyone where they can find you and how to get started with PodMatch?

Alex Sanfilippo: Thank you, Ina. This has been a blast. PodMatch is at podmatch.com.
I also put together a free resource for anyone interested in podcasting. It’s five quick wins that you can read in less than five minutes—no email required. You can find it at podpros.com/win.

Ina Coveney: Thank you, Alex. You’ve been amazing.

Alex Sanfilippo: Thank you, Ina. You’re incredible. I’m so grateful for this opportunity.