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#307 Why chasing success won’t make you happy with Alex Sanfilippo

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What if everything you thought would bring happiness: money, accolades, and status, left you feeling empty? In this conversation with Alex Sanfilippo, we dive deep into the harsh reality of ambition, hustle culture, and the trap of constantly pursuing the next big thing. Alex opens up about hitting rock bottom after early success, how his ego shaped his relationships (and nearly destroyed them), and the hard lessons he learned about what truly matters.

We explore how meaningful connections, purpose, and service bring real fulfillment; things that money and status just can’t provide. Alex also shares his personal battle with impostor syndrome, how faith became a guiding force, and why courage is doing what scares you anyway. If you’ve ever felt overwhelmed by the pressure to achieve or wondered if there’s more to life than constant hustle, this episode is exactly what you need.

Ina Coveney
Welcome back to the podcast! I am here with Alex Sanfilippo.

Alex Sanfilippo
Thank you so much for having me here.

Ina Coveney
Thank you! It’s an honor to be here—super excited about this.

Ina Coveney
Welcome back to the podcast! I am here with Alex Sanfilippo.

Alex Sanfilippo
Thank you so much for having me here.

Ina Coveney
Thank you! It’s an honor to be here—super excited about this.

Alex Sanfilippo
I am very excited as well.

Ina Coveney
We need an icebreaker. Do you think we need one?

Alex Sanfilippo
I’m worried to say yes to anything with you, but sure—yes! One icebreaker. We’re too cold; let's break it. Let’s go. I’m a little nervous, though.

Ina Coveney
Okay, what’s your favorite TV show or podcast that you’re binging right now?

Alex Sanfilippo
Fun fact about me: I don't actually own a TV. But if I think back to shows I’ve really enjoyed, two stand out. *The Office* is one of them.

Ina Coveney
Of course, classic.

Alex Sanfilippo
Yeah, I worked in an office for 15 years, so it hit home for me. I could really relate to the characters—although I’m not going to tell you who I saw myself as.

Ina Coveney
Come on, spill it!

Alex Sanfilippo
Nope! Not telling. The other one is a YouTube show called *Video Game High School*.

Ina Coveney
I’ve heard of that!

Alex Sanfilippo
Yeah! It was made by Freddie Wong, who had a company called RocketJump. Now Freddie’s a podcaster, which is cool. The premise of the show is that all the classes in the high school are based on video games—math is rhythm gaming, the cool kids are FPS players, and you even have drift classes.

Ina Coveney
That sounds amazing! My kids would love that.

Alex Sanfilippo
They would! The whole thing was nerdy and fun. Honestly, if my school had been like that, I would’ve done way better academically.

Ina Coveney
I believe you! Okay, Alex, let’s talk about your work. You’ve created so many different tools for podcasters—tools to help them become better hosts, get amazing guests, and even make more money. Thousands of people have used your products. Does all of this feel like success to you?

Alex Sanfilippo
Yes and no. On paper, sure, everything is going great, and I’m very thankful. But, as an entrepreneur, I tend to always look ahead to the next thing. I hit one goal, and instead of celebrating, I immediately think, “What’s next?” It’s not necessarily a great trait—it can make it hard to appreciate where I am now.

Ina Coveney
I totally get that. So many entrepreneurs struggle with that constant forward-thinking mentality.

Alex Sanfilippo
Right. And the problem with that is we forget to celebrate where we are today. Even though everything looks successful from the outside, internally, I sometimes feel like I haven’t reached where I need to be yet.

Ina Coveney
It’s easy to lose sight of how far you’ve come when you’re constantly comparing yourself to others.

Alex Sanfilippo
Exactly. If I could talk to Alex from five years ago, he’d be like, “Dude, we’ve made it!” But here I am today thinking, “Yeah, I guess we have?” And that bothers me. But, at the same time, I think that ambition is part of what keeps a business moving forward.

Ina Coveney
That’s such a common feeling. The reason I ask about success is that so many people out there are struggling with imposter syndrome. What do you think sets you apart—someone who experiences imposter syndrome but keeps going—from someone who lets imposter syndrome stop them?

Alex Sanfilippo
Honestly, I think I’m pretty good at not comparing my current situation to others. Like, I look at you, Ina, and I know you’ve been doing this longer than I have. That’s why you’re ahead. And I’m okay with that.

Ina Coveney
That’s a healthy way to look at it.

Alex Sanfilippo
Thanks! I also use a Chrome extension called News Feed Eradicator, which hides my social feeds. It keeps me from comparing myself to others because, let’s be real, social media can be a breeding ground for imposter syndrome.

Ina Coveney
That’s such a smart strategy.

Alex Sanfilippo
It really helps. My struggles are more internal, though. A lot of it comes from my upbringing—my dad was always chasing more as an entrepreneur. That drive became part of who I am, and good coaching has definitely helped me manage it.

Ina Coveney
It’s interesting because I talk to a lot of entrepreneurs who follow people they admire, but deep down, they know they’re not aligned with those people’s values.

Alex Sanfilippo
Yeah, I’ve met entrepreneurs who remind me of my younger self, and honestly, it makes me sad. Back then, I had lots of people around me, but the friendships were shallow. When things fell apart, so did those relationships.

Ina Coveney
That must have been hard.

Alex Sanfilippo
It was. The turning point came during the 2008 real estate crash. I had been doing really well financially, but when the market collapsed, everything fell apart—my business, my relationships, even my sense of self.

Ina Coveney
What did that experience teach you?

Alex Sanfilippo
It taught me that the things I thought mattered—money, status, and material things—don’t actually bring happiness. What really matters are meaningful relationships and living a life aligned with your values.

Ina Coveney
Thank you for being so open about your journey. I believe that having a sense of spirituality can be really important for entrepreneurs.

Alex Sanfilippo
I agree. For me, faith in Jesus gave me the courage to keep going when things got tough. Whatever someone’s spiritual path looks like, having something bigger than yourself to believe in is essential.

Ina Coveney
It makes all the difference, doesn’t it? When you’re connected to something bigger, the fear starts to fade.

Alex Sanfilippo
Exactly. It’s not about building a business just for the sake of it—it’s about serving others.

Ina Coveney
What advice would you give to someone who feels paralyzed by fear right now?

Alex Sanfilippo
Take yourself out of the equation. Focus on who you’re serving. When you realize that someone else’s well-being depends on what you do, it gives you the courage to act.

Ina Coveney
That’s such powerful advice. Thank you, Alex. Can you tell everyone where they can follow you and learn more about Podmatch?

Alex Sanfilippo
Of course! You can find everything at podmatch.com/free. That’ll connect you with my world. And if you message me, it’ll either be me or my wife, Alicia, responding—no assistants here!

Ina Coveney
Thank you so much for being here, Alex. You are the best!

Alex Sanfilippo
Thank you again, Ina. It’s been an honor.

Alex Sanfilippo
I am very excited as well.

Ina Coveney
We need an icebreaker. Do you think we need one?

Alex Sanfilippo
I’m worried to say yes to anything with you, but sure—yes! One icebreaker. We’re too cold; let's break it. Let’s go. I’m a little nervous, though.

Ina Coveney
Okay, what’s your favorite TV show or podcast that you’re binging right now?

Alex Sanfilippo
Fun fact about me: I don't actually own a TV. But if I think back to shows I’ve really enjoyed, two stand out. *The Office* is one of them.

Ina Coveney
Of course, classic.

Alex Sanfilippo
Yeah, I worked in an office for 15 years, so it hit home for me. I could really relate to the characters—although I’m not going to tell you who I saw myself as.

Ina Coveney
Come on, spill it!

Alex Sanfilippo
Nope! Not telling. The other one is a YouTube show called *Video Game High School*.

Ina Coveney
I’ve heard of that!

Alex Sanfilippo
Yeah! It was made by Freddie Wong, who had a company called RocketJump. Now Freddie’s a podcaster, which is cool. The premise of the show is that all the classes in the high school are based on video games—math is rhythm gaming, the cool kids are FPS players, and you even have drift classes.

Ina Coveney
That sounds amazing! My kids would love that.

Alex Sanfilippo
They would! The whole thing was nerdy and fun. Honestly, if my school had been like that, I would’ve done way better academically.

Ina Coveney
I believe you! Okay, Alex, let’s talk about your work. You’ve created so many different tools for podcasters—tools to help them become better hosts, get amazing guests, and even make more money. Thousands of people have used your products. Does all of this feel like success to you?

Alex Sanfilippo
Yes and no. On paper, sure, everything is going great, and I’m very thankful. But, as an entrepreneur, I tend to always look ahead to the next thing. I hit one goal, and instead of celebrating, I immediately think, “What’s next?” It’s not necessarily a great trait—it can make it hard to appreciate where I am now.

Ina Coveney
I totally get that. So many entrepreneurs struggle with that constant forward-thinking mentality.

Alex Sanfilippo
Right. And the problem with that is we forget to celebrate where we are today. Even though everything looks successful from the outside, internally, I sometimes feel like I haven’t reached where I need to be yet.

Ina Coveney
It’s easy to lose sight of how far you’ve come when you’re constantly comparing yourself to others.

Alex Sanfilippo
Exactly. If I could talk to Alex from five years ago, he’d be like, “Dude, we’ve made it!” But here I am today thinking, “Yeah, I guess we have?” And that bothers me. But, at the same time, I think that ambition is part of what keeps a business moving forward.

Ina Coveney
That’s such a common feeling. The reason I ask about success is that so many people out there are struggling with imposter syndrome. What do you think sets you apart—someone who experiences imposter syndrome but keeps going—from someone who lets imposter syndrome stop them?

Alex Sanfilippo
Honestly, I think I’m pretty good at not comparing my current situation to others. Like, I look at you, Ina, and I know you’ve been doing this longer than I have. That’s why you’re ahead. And I’m okay with that.

Ina Coveney
That’s a healthy way to look at it.

Alex Sanfilippo
Thanks! I also use a Chrome extension called News Feed Eradicator, which hides my social feeds. It keeps me from comparing myself to others because, let’s be real, social media can be a breeding ground for imposter syndrome.

Ina Coveney
That’s such a smart strategy.

Alex Sanfilippo
It really helps. My struggles are more internal, though. A lot of it comes from my upbringing—my dad was always chasing more as an entrepreneur. That drive became part of who I am, and good coaching has definitely helped me manage it.

Ina Coveney
It’s interesting because I talk to a lot of entrepreneurs who follow people they admire, but deep down, they know they’re not aligned with those people’s values.

Alex Sanfilippo
Yeah, I’ve met entrepreneurs who remind me of my younger self, and honestly, it makes me sad. Back then, I had lots of people around me, but the friendships were shallow. When things fell apart, so did those relationships.

Ina Coveney
That must have been hard.

Alex Sanfilippo
It was. The turning point came during the 2008 real estate crash. I had been doing really well financially, but when the market collapsed, everything fell apart—my business, my relationships, even my sense of self.

Ina Coveney
What did that experience teach you?

Alex Sanfilippo
It taught me that the things I thought mattered—money, status, and material things—don’t actually bring happiness. What really matters are meaningful relationships and living a life aligned with your values.

Ina Coveney
Thank you for being so open about your journey. I believe that having a sense of spirituality can be really important for entrepreneurs.

Alex Sanfilippo
I agree. For me, faith in Jesus gave me the courage to keep going when things got tough. Whatever someone’s spiritual path looks like, having something bigger than yourself to believe in is essential.

Ina Coveney
It makes all the difference, doesn’t it? When you’re connected to something bigger, the fear starts to fade.

Alex Sanfilippo
Exactly. It’s not about building a business just for the sake of it—it’s about serving others.

Ina Coveney
What advice would you give to someone who feels paralyzed by fear right now?

Alex Sanfilippo
Take yourself out of the equation. Focus on who you’re serving. When you realize that someone else’s well-being depends on what you do, it gives you the courage to act.

Ina Coveney
That’s such powerful advice. Thank you, Alex. Can you tell everyone where they can follow you and learn more about Podmatch?

Alex Sanfilippo
Of course! You can find everything at podmatch.com/free. That’ll connect you with my world. And if you message me, it’ll either be me or my wife, Alicia, responding—no assistants here!

Ina Coveney
Thank you so much for being here, Alex. You are the best!

Alex Sanfilippo
Thank you again, Ina. It’s been an honor.

Let the BINGE begin

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