Alex Sanfilippo: From Corporate Climber To Podcasting Trailblazer - His Incredible Journey Unveiled!

KATHLEEN: Hello everyone and welcome to the journey of an awakening spirit. This is Kathleen Flanagan, your host and we are streaming on the Bold Brave TV Network.

KATHLEEN: The purpose of the show is to help you realize that you are not alone. You are in control of your life. It does not matter what your lot in life is or where you came from. We have all felt pain, suffering, hurt, abandonment, loneliness, and hopelessness. This show helps you to take those dark moments and turn them around to create a whole new. You.

KATHLEEN: We were taught to be a certain way, act a certain way. Conform to the society being so socialized is not bad, but it can put constraints on us.

KATHLEEN: The guests I bring on the show are telling you their story of where they were and the obstacles they overcame to be where they are today. They are sharing the tools they use to recreate themselves and their life. Some of the guests are still in their process, beginning a new process, comfortable in their process or even reinventing themselves.

KATHLEEN: They are giving you tools that they use to gain insight into themselves to take control of their life and become the person they are today on podcast dot Kathleen M flanagan.com is a list of the guests that have been on the show with their contact information.

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KATHLEEN: I am a certified coach who can help you reach your dreams. I help you learn how to rely on and believe in your unlimited potential and power. I already know that you've experienced flashes of intuitive knowledge and big thinking that has wondering just how far could I fly?

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KATHLEEN: Alex Sanfilippo is the founder of Pod Match.com, a software that automatically matches podcast guests and hosts for interviews. Alex is also the host of the top rated podcast podcasting, Made Simple and a lead educator in the podcasting industry. Alex's sole focus is to serve independent podcast guests and hosts so they can grow their influence and revenue so they can better serve their listeners. Welcome, Alex Kathleen.

ALEX: Thank you so much for having me today. It's it's been a long time coming and you and I have been closely connected for a long time. So like really this is surreal and really an honor to be here today. Thank you.

KATHLEEN: Well, thank you so much for those kind words.

KATHLEEN: I will preface that when Alex started his podcast because this is how I got into the podcast industry actually is through you, Alex. When I started, I was thinking of doing podcasts and my business partner sent me a link because he received a link to be on Pod Match.

KATHLEEN: And that's when you just started. And I thought, oh, well, let me just look into this. I signed up did it because it was free at that time because you were, I think in the beta stage.

KATHLEEN: And as soon as I launched my questionnaire and profile, somebody reached out to me not five minutes later and said, I want you on my show.

KATHLEEN: And that was the beginning of this incredible journey of podcasting. I started out as guest because it was fun.

KATHLEEN: Ok?

KATHLEEN: And then it's something and then this show showed up and that's why I'm doing what I'm doing now with the show. So it's just been a natural evolution. But I think our listeners would love to know a little bit more about you and how you started and your journey of becoming an awakening spirit.

ALEX: Yeah, Kathleen, first off that, I'm so thankful to hear that. How cool. I love playing a small part in your journey and you've done just an incredible job. I feel like I maybe tell you that too much. I shouldn't. Right. That makes me a bad coach. I'm like, you're doing great all the time, but you really are doing a very good job.

ALEX: And, anyway, I digress but great job and thank you again for having me. My journey, I'd say really of awakening actually happened to be at an age I consider to be very young. So this has made me sound a little bit weird, but I was very self-aware as a 10 year old kid. And not, I could look back at that time.

ALEX: I'm like now and I'm like, was I really that self-aware but I guess I was and here's what I mean by that, I can remember being 10 years old and playing around with kids in the neighborhood and having just a, a great time, doing all the things, right? But I did have the realization that I wasn't the same as the other kids around me.

ALEX: And I say that from the sense of I was getting the worst grades out of everybody there, but I was also working really hard. So it's not like I was the kid who was like, I don't care about school, right? Like I was really trying to apply myself and I saw myself doing worse than the kids that were not applying themselves, right?

ALEX: And when it came to sports because we all played football, soccer, baseball, basketball, everything every afternoon. That was, it was, I grew up in the early nineties, so that's just what we did. Right. Parents said, go outside and don't come back till it gets dark. And, so for me, you laugh right? Times have changed, haven't they?

KATHLEEN: Sorry?

ALEX: You're good. It's so true. I'm sure everyone hears that last little bit. So I remember not being very good at any of those sports. Like I really struggled, but same thing I was trying really hard. And in the evenings we play video games because we also grew up in the nineties where n 64 was becoming a thing.

ALEX: So the Nintendo Device came out and I wasn't as good at that as the people around me and all three of my younger brothers were musicians and I just didn't, couldn't keep, it, couldn't keep a, couldn't clap on people. Let's put it that way. Right.

ALEX: And so, like I had this realization that, ok, I'm different than everybody here and it wasn't that I was down on myself. I just, for some reason, had the awareness that I hadn't found my thing yet. Does that make sense? Like at 10, I know that sounds a little bit maybe strange. But I'll never forget it.

ALEX: One day we were playing on the golf course across the street from our neighborhood because we were kids and all the parents said don't go on the golf course. So we'd run straight for the golf course every afternoon. So there we are on the golf course. And one day I was out there and I saw a golf ball just sitting in the middle of I guess it was the fairway, but there was no golfers.

ALEX: So I just picked it up and I was like looking at it and out of nowhere, a, a golfer comes by on a cart and he goes, hey, kid, what's that golf ball say on it? So, like I walked over to him and I was like Titleist pro V one and he goes, I'll give you $3 for it.

ALEX: And I was like, deal. So I gave him the ball, he gave me $3 and I immediately grabbed all the kids, I think we were playing football on the golf course. That day I grabbed them all. I was like, guys, that guy just gave me $3 for this one ball.

ALEX: Let's find more of them and see if more golfers will buy from us and all the other guys, some of them older than me, like when I say older than me, they were 11 or 12, I was 10, right? And some of them were younger. But at that point I said they all were like, kind of like, well, how do we do that? And I was like, well, does anyone have a way to get them out of the lakes?

ALEX: Can you go do that? Ok. Does anyone here pretty good at cleaning stuff? If you are, we need to clean these things? There would be NASA in one of the lakes, there was all these different things that had to be done.

ALEX: And in that moment I can remember having a real time strategy get developed that I mentioned to everybody and everyone was on board to do it. And so that coming, that was like a Tuesday, I believe, I don't know how I remember that, but I remember it being early in the week a sell on Saturday and we knew we had time to do it.

ALEX: So we just went out and found as many as we could and we started selling them on Saturday. And so yes, I started selling used golf balls on a golf course. It was my first taste of entrepreneurship. But more importantly that it was the first time in my life, I felt like I was doing something that I was good at. Like that came naturally.

ALEX: That got me excited that people wanted to follow. When I said something, I could talk to an adult and I could negotiate with an adult because believe it or not, some of these guys were cheap and like, I'm not giving you $3 I give you two right? I had to be the guy 50 right, as a 10 year old.

ALEX: But the reality is, I kind of became comfortable with that stuff and learned to actually really flow in that. It was the first time in my life in church. I'm only 10. Right. But at 10 years old had the realization of, you know what this right here is my sweet spot.

ALEX: It's not sports, it's not music, it's not video games, it's not school, it's any of those things and not that any of those are bad. I still did all those throughout all of school, but I knew that my thing was gonna be something more in the leadership slash entrepreneurship type space. And that was really the first time that I had that awakening if you will.

KATHLEEN: Ok. That's a funny story.

KATHLEEN: 10 years old that's, I already knew I was different too, so I understand that part of being different, but I certainly didn't get what you got. You know, I just kind of went down a different path. But so when do you? Ok. So now that you know, that you are going to be an entrepreneur, but that's not where you started out. You ended up becoming a corporate jobber.

ALEX: I did, you know, and interestingly enough, you had a recent guest on that. I really enjoyed Walt Morgan. He came from the same industry as me, aerospace, totally different though. I have to give this preface here. I wasn't a skydiver astronaut or fighter pilot. I work behind a computer running like running parts manufacturing basically.

ALEX: And that's kind of like what I went into but like we came from the same background and by the way, I encourage anybody who's checking this out. If you've not heard Kathleen's conversation with Walt, you've got to go back and hear it. I wrote down the date so you can find it.

ALEX: It's April 9th 2024 talking about flying high to leading change. I mean, truly inspirational, transformative like Walt Morgan and Kathleen just had great synergy. So I encourage everyone, go back and please check that out. Hang here with us now. But if you're tuning in live, but I do encourage you to check that out.

ALEX: But, you're right, Kathleen, I started off with a corporate job and I should actually mention before that when I was in high school, I thought that entrepreneurship was gonna be what I wanted to do. And so I actually started working in the real estate industry a little bit. I was good on a computer when it came to business.

ALEX: So I actually helped develop some technology to do virtual tours of homes, which was a really cool thing. We were like the first people to ever do that. Now. It's very common. It's where you can kind of go to a website like let's use Zillow as an example and you can kind of drag the mouse around and look at the whole house, right?

ALEX: We were doing that tech in the early two thousands. So I was a high school kid doing that and I actually ran a company with three editors and four photographers and we were working on the MLS just developing these things for different realtors and different offices and stuff like that. Absolutely fell in love with that.

ALEX: I mean, if you think about it, I was I guess I was 16 and 17 when we got that started. So it had been like the early two thousands. We were, it was a fully remote company back then. We actually used AOL AOL instant Messenger. That's how we actually communicated because there wasn't any other tool.

ALEX: So we just had our own little private group and we just kind of went with that. But that was really what got me started in business before going corporate. But I think the important story here, Kathleen and share it is the transition between those two because they don't add up at all. Right. Like corporate guy, real estate entrepreneur.

KATHLEEN: Well, yeah, because you're an engineer.

ALEX: I worked with a team of engineers. I was never actually an engineer, an engineer. I worked directly with a team of engineers.

KATHLEEN: I should be really talented because they are really hard people to talk to, I mean, once you understand how to talk, once you know, their language, then they don't stop talking to you. But it takes a while to learn how to deal with that. So that's why I thought you were an engineer because you were always around engineers. Yeah.

ALEX: And that's actually been totally calm the whole way through. People have thought I was an engineer because I actually was managing teams of engineers and working directly alongside them. But I never actually had a certification myself.

ALEX: But before I can, that kind of go back the story that I think is gonna be really transformative. Like it was my transformation. When I turned 17, I got really excited about real estate. I wasn't the guy going to the houses to take the pictures, there was photographers doing that, but I was helping lead the editing team and the business side of it getting new business, all that stuff.

ALEX: And I can remember like seeing these houses, these pictures come through and I'd like call up the photographer and be like, hey, did they add that bathroom later? You think like that looked really cool? And then I was like seeing the MLS, I'm like, oh that did a lot for the value of the home. That's also very interesting, right?

ALEX: I'm actually seeing the increase of the value of the home because of this, the whole reason I'm sharing this is because I started getting really passionate about real estate. And I knew as a 17 year old kid when I turned 18, I was buying my first rental property. It was gonna be time I had the company to give me the income that I could use to be able to buy that investment property and get started.

ALEX: I'm gonna go ahead and tell you all the year this was 2006 is when I decided it was time to start investing. There we go. Kathleen remembers.

ALEX: So sure, the top of the market bought a property, got a renter in there still running my company as well.

ALEX: And then this crazy recession hits.

ALEX: Now I own a rental property that I'm instantly really, really upside down with in this business that runs off a good real estate economy, right? That now I gave it to a partner. I didn't even, there was no money exchange. I just said, hey, if you still want to do this, go ahead. We went from doing 30 different tours a day to one or two a week if you can just think about the change in business.

ALEX: So I went from seven people working for me to zero overnight and then also no one doing anything. So the one person who stayed with me, I just I gave it to one of the guys, sorry, there was seven of them were six and then I gave it to the one I was just like, hey, if you want to run with this, go for it, maybe the economy will turn around at some point. But the reason I share that Kathleen is, I was defeated.

ALEX: I went from a very early win at 10 years old. Right. And then throughout high school, the things I didn't share is I love flipping stuff. That's when Ebay became a thing. I started flipping things on Ebay and it was just so fun. I was always profiting, always doing well.

ALEX: And then this thing happens and I go from being an 18 year old kid who is doing better than anyone I knew at that age. And I said it humbly, I'm not saying I had to be conceded at all to doing worse than anyone I've ever met in my life. Like just a full 180 and to kind of make matters worse at that point in my life. I developed a a bit of an ego just because again, things never went wrong after the age of 10, right?

ALEX: Like I found my lane and I was just doing well. And when I was 18, right after I bought that property, I remember I was sitting in a dental office and there was a magazine there, I believe it's Forbes that does like the 30 under 30 like top 30 under 30.

ALEX: And I like open that magazine I made it a goal in that moment saying, you know what I'm gonna be one of these 30 under 30 real estate is going to get me there. I'm gonna crush it. That's gonna become my identity. That's gonna be who Alex Sanfilippo is. Forbes. 30 under 30 just crushing in every single way. And, so I had all that ambition.

ALEX: The people I surrounded myself with were not great people and I don't mean to put them down at all. They were just really interested in hanging out with money, right? Even the girl I had in my life at that point was also very interested in the money that was involved, right? So all these things came to a screeching halt.

ALEX: So I believe at this point, what was that? 19 I guess is when is the whole economy really wrecked 19 year old kid? Just absolutely rock bottom in every way. The friends disappeared, the girl disappeared. My dream of becoming that top 30 under 30 disappeared all out the window. And now I'm, I have a broken ego and just all I can say is a puppy that had been beat.

ALEX: This is what I really felt like. Like that's kind of the way I walked around a little bit and I'd actually still this day, Kathleen consider that the low point of my life like that was absolutely the low of the low depression, anxiety, all that stuff hit and I didn't even really know what that was until it hit me one morning when I woke up.

ALEX: That was a tough time for sure.

KATHLEEN: We're gonna take a quick commercial break and we're gonna talk about the flip side of that of what transforms once you come, once we come back.

KATHLEEN: Welcome back, everyone to the journey of an awakening spirit. This is Kathleen Flanagan, your host and we have Alex Sanfilippo in the room with us and he just got done telling us about his bottom of the bottoms. And so I'm going to turn this back over to Alex to continue the story and how, what he did to turn all of his life around.

ALEX: Yeah. Thank you. I say it was the bottom. This next step might have been it for just a very short period. I guess this is like the end of the bottom. But I remember during that time when I basically had no work super in debt, I couldn't afford school anymore. I was just going to a community college here in town. Never got very good grades. So I knew community college is right for me.

ALEX: But I couldn't afford it and I'll never forget I called my dad and I was like Hey dad, I was like, real estate is like, just not gonna happen. And I've always had a lot of respect for my dad. By the way, he's an entrepreneur himself and he's done just really well.

ALEX: And I asked him like, hey, I know you work in the aviation, aerospace sector, like, how's that industry? And he's like, booming, he's like, we're fine because of the sector that we're in. I was like, do you know, anywhere that could get a job?

ALEX: And he's, I can get you an interview somewhere and he's like, but that's all I can get you. I was like, OK, I was, I'll take an interview. So no experience 19 years old. I show up at at company with a, I guess it was like a company controller or something like that was doing the interviews at that point.

ALEX: Head of hr or somebody who I didn't expect, but they sat down and looked at my resume which was pretty much nothing. I don't think I had the golf ball story on there, by the way, maybe I should laugh, but I don't think I included that there just wasn't much on there.

ALEX: And, he's like, well, we're, he saw my last name and I'm very thankful I got the opportunity. He's like, we've got a part time position available. It's a part time receiving clerk position when we got into it. What that basically meant was I was gonna be breaking down boxes and taking out the trash and I was like, you know what I can't eat.

ALEX: So if the job is open, I will do my best at that job. And again, like leaving, that was kind of like that was if there was a bottom, that was like kind of that moment. I was like, oh man, you know what?

ALEX: Ok. And it was in that, it was that flip right there that, ok, I just have to do this. Maybe it's temporary. I don't know. And, I started showing up. I mean, it was tough and again, I was still like that lacking ego type person.

ALEX: Well, anyway, around this time I got into that and it was about probably a year in to it and I still had that same position, but I had moved to full time and I was really thankful for that and, not everyone got full time. Apparently that's just not how it really worked there.

ALEX: But I was a guy who looked at trash cans that were always empty and trash cans are always full saying we need a bigger one here and we don't even need one here.

ALEX: And instead of us breaking down boxes in five different places in the business because of a giant building, let's have everyone have carts where we can bring it all to one central location and break them all down in this one spot. And that seems really small, but no one had done that before. So it made me stand out as the person who's going to get the full time job.

ALEX: And back then the term I'm about to use didn't exist, which it does now, but it's called an intrapreneur, which simply means an entrepreneur inside of an organization. And that really throughout my entire corporate time is really how it's kind of how I operated.

ALEX: And so anyway, I was still just kind of going through the motions. I definitely kind of walked around with a defeated mindset and sure, I now had income coming in. I had a full time job. It was all fine, I suppose to the world standard.

ALEX: But I just remember like still hurting, I'd go home alone. Feeling alone, I think I had roommates at the time, but still just like feeling alone, that was always there something was missing and I'll never forget it. This was like the absolute biggest change my life in a positive way. I shared the negative way, right? This was the positive way. I got the mail and I expect it to be full of bills, right?

ALEX: Because that's usually what comes in. But there was actually a flyer for a young adults ministry for church and I was like, oh, I looked at the address and I was like, I could walk there. This is like two blocks that way, you know, like I recognize like same zip code, basically the same address. I was like, maybe I'll go to that.

ALEX: I left it sitting on my counter for three weeks because in my head I said if they find out how bad I failed, these people are gonna judge me and make fun of me because I feel like that's all I've ever seen in my adult life is people judging me, making fun of me and leaving me because I didn't amount to anything. And I didn't even know I had that mindset, Kathleen.

ALEX: Like I didn't know that was a struggle until there was an opportunity in front of me to go meet people. And I was like, no. And finally I did what I guess I do wanna share this because I think it's helpful for people to hear. But it took courage and what courage means is being afraid then doing what you have to do anyway. Courage means being afraid and doing what you have to do anyway for me, I took courage.

ALEX: I decided, you know what, I'm gonna go find this place down the street and I'm gonna go, I'm gonna go this week and I walked in by myself. I just walked in super nervous and I was never like a social anxiety type guy. I've always gotten along with people I did think, but I was just worried that they were gonna realize that I'm a fraud and that's how I felt. And I walked in there and everyone was super kind.

ALEX: But on top of that, once the service got started, this is like we were, they were just talking about Jesus and I heard about Jesus growing up, but I never really had a relationship and they just kind of had an invitation to start a relationship with Jesus. And I was, well, if Jesus is, if God is who they say he is, he already knows that I'm a fraud, a failure, a loser.

ALEX: And if for some reason, there's someone, some being a higher power crazy enough to be ok with that, I'll give it a shot and I can't even explain what happened, but something shifted inside of me to realize that there was something different. And like if there was an awakening spirit moment, that's what it was for me.

ALEX: I left there, came back the next week, started making friends shared transparently because I just got more courage. Right? And no one cared that I hadn't made it. No one cared that I was breaking down boxes and taking out trash for people. Right? Like no one that didn't bother a single person there. They still wanted to hang out. They still want to spend time with me.

ALEX: On top of that, I started having this relationship with God that I can't describe it, but it changed everything about me and going back to that corporate job, after this changed my circumstance didn't change, but my mindset did. And much like again, going back to Walt your prior guest who mentioned enjoying his time in corporate.

ALEX: I enjoyed my time in corporate. From then on out, I actually ended up doing a 15 year career in total and I just work my way up every single year. It felt like I was working my way up and I wasn't making that the goal. I just started showing up for more than myself. I started showing up because I'm like, you know what I feel that God wants me to do the best I can every single day.

ALEX: And that's the one person who gave me a shot. So I'm just gonna apply myself every single day. I'm gonna work like, I'm working for Jesus and to love people. Well, because that's what I was experiencing in my life. So I love the people. Well, as I started getting into management and I ended up like we talked about earlier, leading even a team of engineers.

ALEX: We had an engineering division, sales division. I end up leading actually five divisions in the company. When left, I was kind of as high as you could go, I was reporting directly to CEO was on the C suite and that was kind of like the whole journey if you will.

ALEX: But it was like, and I'm fast forwarding like there was ups and downs, of course, in business when the company is doing well when it's not right, especially when you kind of work your way up. But all in all it ended up being a really beautiful experience for me. Thoroughly enjoyed it. And it was all going back to that moment when I felt that that relationship with God began.

KATHLEEN: There's no doubt when you bring God in your life, your life changes because you realize that you're still loved no matter what you think of yourself or what people say about you.

KATHLEEN: Because I remember there was this one event, it was, it was in the, I think.

ALEX: No, you're muted, you're muted.

KATHLEEN: Sorry, I don't know what's going on with this today, but I was, I was very suicidal in 87. And people, I mean, I would tell people I was suicidal because, there was just so many things that were happening in my life and I couldn't get through it. And what did I do?

KATHLEEN: I went in, I remember going because I'm a Catholic recovering and I went into church and they were singing Amazing Grace and I sat there and I sobbed through that whole song of, oh my God. Do you and I'm like, do you get this? Do you get, do you get this?

KATHLEEN: It was like that was how I felt because I had felt that song for the first time in my life because everything, all those words in that song were talking to me and that's when I everything flipped for me then too. It was, I found a hope to keep moving forward instead of ending, wanting to end my life and whatever that looked like at that point, it was enough.

KATHLEEN: So I understand fully when you bring a higher being into your life, whatever that is, you want to call it. When you do that, there is life changes. So I know that something had to happen when you were in the corporate world that brought you into the Pod Match world.

ALEX: Yeah.

ALEX: Thank you for sharing by the way like that, that hope as you said, like what a beautiful thing. I mean, it's believing what we can't see, right is hope and a lot I think the best things in my life and it seems like yours as well are things we couldn't see. And I think Kathleen, you do a really beautiful job of describing those things.

ALEX: I'm a work in progress on that, but that's something I really personally admire about you is you can describe them in a way that causes other people to say, wow, I need that, right? Maybe people are like, what is this Guy talking about. Anyway, that's just a beautiful thing that you have. You have a gift to do so. Thank you for that. By the way, you're welcome.

KATHLEEN: Well, we're gonna take a quick commercial break because I just got noticed that we have one minute. So I wanna get you to have an uninterrupted story. So we'll be right back.

KATHLEEN: Welcome back, everyone to the journey of an awakening spirit. This is Kathleen Flanagan, your host. We are streaming on the Bold Brave TV Network and I have Alex Sanfilippo in the room with us today and he was just getting ready to tell us the next stage of his life.

ALEX: Yeah. So just sharing that like I had that 15 year career, right? And people still this day are like you left that, that seems like a really good gig. And it really was I had a moment though that I realized it was time to time to exit, time to leave. And it actually came at, I believe it was year 13 in the business.

ALEX: And so it was 2018 at that time, it was my 13th year there. The company actually went public and I was on the team to help it go public that's eventually kind of propelled me into the c suite level was getting acquired by a multibillion dollar Canadian aerospace company. And so it was like a huge, huge thing. Like it was really cool to be part of.

ALEX: And I'll never forget it though. This was about six months after we finished the whole thing. It was not a year process. So I guess it started from year 12, ended in year 13. And so now I'm on my 13th year, about six months in, I was overseeing five divisions of the company and one of them had, we just did so well, like in a single quarter, we did what we hadn't done in years.

ALEX: It was a full 10% margin increase to our bottom line. And again, we're now billions of dollars getting flowed through. So in my head, Kathleen, I walked down to my CEO S office and I kicked his door in holding my scotch and my cigar. I wasn't really, but my head, that's what was happening, right?

ALEX: Because it was a proud moment, realistically, what I did is I knocked on his door and said, excuse me, sir, can I have a moment? That's probably what really happened. But I sat down and, I was like, hi, his name is Paul. I was like, hey, Paul, did you see the report?

ALEX: And he goes, yeah, I saw it and I could hear in his voice, he wasn't excited about it. So I kind of like lean forward because I expected him to instantly praise me and maybe I went in there for that reason. I don't know. But I lean forward. I'm like, you realize like we saved that extra margin.

ALEX: We didn't lose that. He goes, no, I know I saw it and I just put my hands and I was like, well, everything, ok? And he goes, no, everything's not, ok. He's like, we didn't tell the shareholders that we're gonna do that. He's like, we didn't tell the board, you're gonna do something big like that.

ALEX: He's like, they're really mad. He's like, they could have been selling at much higher rates if you would have told them we're doing something so drastic there and he just told me he's like, hey, just if you're gonna do something like that again, like we gotta have a plan, we got to talk about it.

ALEX: I was like, all right, I'm sorry, like I didn't know I'm new to this and he goes, I understand. And so it's fine. That was it. I closed his door and I was walking back to my office, which is really just a few doors away from his. But Kathleen, it's the first time in that building that I felt like that walk took 10 minutes there.

ALEX: Hadn't been a day there where I felt was like, oh, just another day. But this was the first time I was like, wow, this is a long walk. And in that walk, I was just processing all this. And by the time I got to my desk, which again was just a few seconds.

ALEX: I had made the decision that, you know what, this isn't gonna be for me anymore. And what I now realize is that was, is I lost the opportunity to be an intrapreneur. So again, an entrepreneur operating inside of an organization, I was now required and expected to follow the status quo and to work off a sheet and a group of people's expectations and not to exceed or go below that at all.

ALEX: And here's the thing like I'm not saying that to be mean about the company, like they're still doing really well and that's how big corporations eventually go and they, run that way and it can kind of just be a cash machine, I suppose, right? I knew that's not what I wanted. And so at that moment, I knew that was just gonna be it.

ALEX: And so at that point, I tried a bunch of side hustles because I would go back to 10 years old now, right? I'm like, you know what, as a 10 year old, I was good at this, which means I'm still gonna be great at it. And the reality is when I started trying all these little side hustles that because just to be very clear here, I applied myself to the last day I was there.

ALEX: Like, I never started slacking. Like the company still got 100% of Alex Sanfilippo. That's what they paid for. That's what they got. But when the extra time I had, I started just trying little things, Kathleen, nothing worked.

ALEX: And I got really insecure again in my life, which hadn't happened since I had that awakening with God, right? Since I found Jesus, like I hadn't had that moment, but I was like, maybe I'm just supposed to not challenge the status quo because apparently I don't get this entrepreneurship thing anymore. Like things aren't connecting and working.

ALEX: And before this, I only had one failure in real estate and everything else I did worked. So what's going on here? And I got some advice. Someone's like, well, you need a coach. I was like, that's a great idea. And I was like, I think I'm gonna do that. And I met with somebody who I would consider a coach and said, what you really need to do is start a podcast and get free coaching from a bunch of people.

ALEX: And I was like, what? So the idea was I started a podcast to learn how to become an entrepreneur. So leaving a 9 to 5 job to become a full time entrepreneur, I talked to people who had successfully done that to learn what they did and how they did it and make it valuable for others.

ALEX: Because again, I lived a life of service at this point which I decided ever since I found Jesus, right? Like serve and love people is one of my top things. And so, I started learning from these entrepreneurs and this was a true side hustle and I'll never forget this. This is like eight weeks into it. Actually, Kathleen, the CEO of my company came into my office.

ALEX: He goes, Alex. It's like I've been listening to your podcast. I was like, oh, like I'm in trouble, you know, like I'm in trouble and he goes, man, this is really good. He goes, you've got something here. Keep on doing that. I was like, oh OK. Thank you. Right. So I just kept it going.

ALEX: And if I fast forward a full year and a half into this podcasting journey, Kathleen. But what I realized about entrepreneurship is that I maybe did have it wrong. But I learned kind of the four steps and I'll share those really quick because it's not really what we're talking about here today, but I'll share very briefly. Step one is find an area of passion.

ALEX: Step two is to get into the community where you're passionate. Step three is to find a simple problem that people in that community are struggling with or suffering with. And then the fourth thing is to offer a simple fastest solution to whatever that problem is. And that's what I learned. And I'm way simplifying it from some of the most brilliant minds I've ever met in my life.

ALEX: But the reality is that's what it came down to. And what I realized in that moment through being a podcaster for, I believe, a year and a half at that point is that I loved podcasting. That was my area of passion. So I was in the community at that point as well. I was actually speaking at the different events and one time I got off stage, this was actually, January 2020.

ALEX: So just before the whole world shuts down, I was speaking on stage, there's about 2000 people there. And when I got off stage, I made a point to have pen and paper in my hand and I was gonna ask anyone who would talk to me what it is that they were struggling with to see if I could find a common problem.

ALEX: I heard a lot of things, but I did write down 100 times that people said I'm having trouble finding guests or simplifying the process of connecting with guests or working on my administration when it comes to guest host matching, right? Like all that stuff. And that's where the idea for my company. Pod Match came from and for anyone who's like, ok, what's this Pod Match thing?

ALEX: I'll share it very briefly. Pod Match is a service that connects podcast guests and podcast host together for interviews. It works very similar to a dating app, but instead of connecting for dates, it connects them for podcast interviews so they can have a conversation like Kathleen and I are right now and that was what I learned.

ALEX: The problem was and that was the solution, decided that I decided to offer. And man, that was fun. Like what a fun thing to like get into because it was a total 180. And I went from like working on engineers to now working around software people which they actually have very similar minds. So it translated very well for me.

ALEX: But yeah, that was what ultimately, at this point, I was actually doing both things that I'm sharing, but this is ultimately what led me to full time entrepreneurship.

ALEX: Oh, you're muted.

KATHLEEN: Ok. Mercury is retrograde. Ok. So it's having some fun with me today.

KATHLEEN: I have to tell you when I got into Pod Match or podcasting. That was the one thing is finding we are the host because it was amazing how many, even though there were a lot of podcast shows out there, not everybody was doing them because they never go down, they always stay up.

KATHLEEN: So that became a real challenge. So when, and my business partner knew that I was really interested and wanting to do podcasting. So when he found, when you sent the link to him, he sent it to me and it was like, oh my God, because it was one company that I went to.

ALEX: No, you muted again.

KATHLEEN: I have no idea. I'm not even near my mouse. I'm not gonna touch anything. I'll just sit on my hands.

KATHLEEN: Anyways, but they were out of England and they were doing something similar, but I got nothing. I got absolutely nothing out of it. And then you come along, this little beaming, shiny, shiny light comes along and you and you actually responded to an email which blew me away that it was the owner of the company because how many CEO S answer emails?

KATHLEEN: Very few. So that was surprising. And we just had this instant connection and this whole show and I'm booked out a year right now. I'm in March. I can't believe I'm in March and it's all because of this show. It's because of you. I haven't searched for one person.

KATHLEEN: They all keep coming to me and I love it because it's like I don't have to go out to the struggle of looking for people because sometimes it's hard to find people as a host if you're not connected either. So, I mean, what a beautiful gift that you gave the world to connect people and then your team is just friendly. They're nice. They're loving, they're supportive.

KATHLEEN: I mean, I've never been in a community like yours because I've been in other groups and organizations and I've never felt what I feel with you guys. So this is a plug for Pod Match people because it really is, if there's something you want to do, this is really the place to go and, you know, it's, it's really inexpensive too.

KATHLEEN: I mean, there's, I know there's different tiers, but it's a very inexpensive place. And you know, thank you for bringing this genius out to the world because I think that's the one thing is people do listen. I mean, my partner listens to podcasts all the time, all the time.

KATHLEEN: He's always on a podcast and I listen to more, I try to listen to more of my time is I spend more time trying to get the show up and doing and being ready for the next guest because I want to give my guest every opportunity to be presented, to be seen to come to here and all of that because that's my job as a host, in my opinion, is to make you shine because of the gift you are bringing to the world.

KATHLEEN: That's all I have to say. So that's a plug for you.

ALEX: Thank you for the kind words like means so much. And ever since the first time I can still remember the first time we actually had a face to face call and it was early on for me and I still this day appreciate those moments because I was full time aerospace still and then doing this part time, it was like just really cool to meet people.

ALEX: I'm like, wow, this is actually helping people. And again, I just appreciate your kind words.

ALEX: And if it's helpful, I can share the transition of leaving full time to becoming that full time entrepreneur if that's helpful as well to go there.

KATHLEEN: Yeah, go for it.

ALEX: Cool. Ok.

ALEX: So 2020 it was actually, yeah, I had the idea officially like wrote it down on white boards. It was a little slow, but it took me a little bit. But on March 10th, 2020 officially had the Pod Match idea called up a friend of mine who was a developer and we just signed 50/50 documentation paperwork and just got started.

ALEX: So we like legally buttoned up like in one day and just went for it. We put $5000 in the account and just said, let's go and see what we can do here on June 15th 2020 is when we launched and kind of just hit the ground running like it was that time in the world where like timing was perfect because people that previously had big stages, right?

ALEX: I'm talking like big like actual public speakers that are full time public speakers now had no job and a lot of them were just posting everywhere on social media. Like, does anyone want me to speak virtually? Like, I don't want money. I just want to stay fresh. I just wanna serve. Right. I want to add value.

ALEX: Which was a cool time to see people wanting to help one another and somebody I don't know who it was, but a big name, public speaker just posted, just found this Pod Match thing and posted it and it absolutely went viral. I told my co-founder, Jesse, the developer, he's like, how many people do you expect to have using it by the end of July?

ALEX: And so again, we launched on June 15th and I was like, OK, a month and a half, I was like, I expect maybe a couple of 100 maybe 200 because I had 100 people on my list that wrote down their name earlier that year. So I was gonna invite 100. So I was, hopefully they'll all bring one person with them.

ALEX: It was I think June 25th and Jesse calls me. He goes, dude, I was like, yeah, he goes 1000 people joined while we're sleeping. I was like, oh, that's so cool. He goes, no, we didn't build the infrastructure for this dude. He's like, I'm not gonna sleep for weeks now to try to keep up. He's like, everything's breaking. I was like, oh, I didn't know how software worked.

ALEX: I was like, the tolerance isn't set high enough. He goes, stop thinking like an engineer. He's like, it's different. But yes. And, so we had that conversation and, our 1st 1000 people came within just a couple of weeks and I'm still this day, very thankful for that. And that's not when I left.

ALEX: I actually could have not that we're bringing enough in financially, but like, I could see the writing on the wall that would happen. But, something kept me at my job and, I just kept on staying my co-founder who had a really big, I mean, much bigger corporate job than I did. He was working government stuff, as a database builder and that's always a lot to talk about.

ALEX: He quit his job way before I did. And I was like, what are you doing, man? He goes, dude, the writing's on the wall. This is serving people. This is what we wanna do. Let's do it. And I remember talking to my wife and I was like, sorry, not talking to my wife, Alecia.

ALEX: And she's been the most amazing support to me forever. But I was thinking if I told her I want to quit my full time job, this was gonna be the first time she wasn't supportive. Like I just like I was like, oh, Kathleen, I was nervous. Let's put it that way.

ALEX: And finally this was.

KATHLEEN: And, you know, women, well, don't you?

ALEX: Maybe, but not as well as I thought because I sat down, I was like, I think I need to leave my corporate job. Alecia.

ALEX: And, she goes, wow.

ALEX: And,, here it was, I expect her to be, like, no way. That's our stability, like no chance. And, she goes, you know, I trust you completely. She's if that's what you feel we're supposed to do, she goes, let's make it happen.

ALEX: Is there something I can do to help? At that point? She instantly came on and started working with the business. She was working with another organization and just like, came on with us full time right there and was like, let's get you out of your job ASAP.

ALEX: And I told her I was still super nervous. I called my dad and I was like, dad, I think I'm gonna get it out of aerospace. You got me into it 15 years ago. I think I'm gonna get out of here. What do you think? He's like, it's the best time ever to do it. He's like, you have a great idea. I think you should run with it. My dad's a straight shooter. Right?

ALEX: And I was like, all right, I'm gonna do it and I was still nervous and I went back to the words that I shared earlier, which is courage means being afraid than doing what you have to do. Anyway, I was super nervous, super scared. And at that point, I remember I walked into my CEO S office and told him I'd be leaving and he goes, man, you know, I've been following you since you started your podcast.

ALEX: He goes, I knew that this was gonna happen. He's like, it was just a matter of time and he's like, how long can you give me? And so we negotiated, I ended up giving him 90 days. So I ended off the the year 2020 with them and helping move everything along. And I'll say this my last year in corporate was by far my best year.

ALEX: Every year I did, I did well, I worked my way up my last year. I can say I accomplished in one year what I did not think was possible. We finished two years of road map projects, all of my division. So the top five divisions in the entire company were all mine and my CEO right before I'm leaving. He's like, hey man, he's like, you're sure you want to leave, right?

ALEX: He's like, cause I can't give you a big bonus during COVID year. He's like, but next year you have a huge bonus coming. He's like, you've outperformed in every way. And, I was like, now I gotta go. He's like, I knew it wasn't about the money for you. He's like, you've always been like that and he shook my hand and that was it.

ALEX: And I walked out of that building, December 7th 2020 cried on my way out the door, looked back at the building knowing I'd probably never walked back in that place. I spent 15 years there, right? Like most days, 10 hours, sometimes 12. And that was the day when I got home. I was like, this is my office now, I guess, right, this extra room in our house is gonna become my office.

ALEX: And from then on made a devotion to say, you know what, I'm not gonna help build another big corporation. Again, not that there's anything wrong with that. I just knew I wanted something that really serves people and lets people feel loved and we build a platform that allows them to go out and do the same.

ALEX: And I believe that podcasting this day, an interview on a podcast is one of those beautiful things that somebody can listen to because you really are hearing such raw, authentic journeys. Like again today, I had the honor and privilege of getting to listen to your podcast. This one, the journey of an awakening spirit and man inspiring.

ALEX: I felt better after I listened to it and I'm like, that's the beauty of podcasting and it's just such a drain. We'll do it full time. And that is my journey from employee to entrepreneur. And it's really been a beautiful thing. And I feel that as an awakening spirit myself, I'm still very early in a new journey for me, like really early. But I'm optimistic and really excited about where it's going.

KATHLEEN: And the other thing too, Alex is that you trusted, that was the thing. I mean, I believe in divine timing and everything that you talked about and how you let into it is all divine timing and when that nudge comes in your little brain and our little ego says, oh, I don't think so, but that little nudge is a little stronger and you're having that little personal interior battle.

KATHLEEN: It's the ego. Some people, a lot of people allow the ego to run. But those that really know that really have that connection where they really are aware of their connection. I think they trust that quiet, still voice in their head.

KATHLEEN: And that's why Alecia was probably extremely supportive is because she probably had the same thing going on in her own mind with because how can you sit there and say, well, I need to stay in my corporate job because I can make 6-7 figures here. But you've got this like I have 1000 people and, overnight, the writing was on the wall.

KATHLEEN: I mean, you could go far, surpass whatever a corporate job could ever do and you have the freedom to be able to do the things that you want to do instead of working within the constraints of what corporations demand of you. Because I've watched Pod Match evolve to pod pros, to the community that you have.

KATHLEEN: The training that you have. All these different things that you have developed within. It is just been a godsend for me because it's made my life so much easier, especially when you're doing a podcast show and you've got all these working components and that workflow you gave us is like, thank you, Alex.

KATHLEEN: I am forever grateful for that workflow because sometimes I think I did it and I go back like I forgot to do this, you know, and you're just, and it's like that little startle because you think you have it in your brain all the time. No, no, it's not always in your brain.

ALEX: It happens to me every day. So I feel a lot better hearing. You see that I kind of live by that list, right? There's a lot that goes on. Don't you think a lot of people that aren't, that are just even just listeners? I'm not like, oh, you're just a listener. That's great. That's what makes what we do worth it. But a lot of people don't realize the work that you put into this, Kathleen.

ALEX: Now, I might be the first step because I just listen to it like there's a whole team behind this. There's a whole system to make this work and it's not just me and Kathleen show up, hit record and then it's done like this is 10% of the work maybe, right? This is for this to go like you have to be fully here. And anyway, so thank you for the work that you put into this. It's incredible.

ALEX: Yeah.

KATHLEEN: Well, you're welcome. Welcome. So what is one piece of advice that you would offer our audience to help them move in a different direction to achieve their dreams or become a better person?

ALEX: So I'm a really type a personality. I love steps and actionable application, all that stuff, right? Keeping it practical. So I'm gonna give you, I'm gonna give five steps if that's OK. And I think that these things flow really well together for me and forgive me because I know that's not the norm of what's shared here.

ALEX: But the first thing I want to share number step one is to get real with yourself. I found the best way to do that is take pen and paper and be alone, go somewhere that inspires you for me. I live in Jacksonville, Florida, very near the ocean, sitting on the ocean with pen and paper. No digital device is where I can get real and slow down and stop and just figure out who is Alex Sanfilippo.

ALEX: And where is he going? And why is he going there? Right. Like I literally think of myself in third person. I just write down what comes to mind. So step one stop, get real with yourself right after that. Step two, I'd say get help. Like when you start doing that, think of the people in your life that can be a guide.

ALEX: And I'm actually gonna recommend Kathleen right now, like in high level transformation coach. If you've been listening to Kathleen for a while and you've not reached out like I'd say it's your time to do that. Step one, right? Go get a pen and paper. Think about where you're going when you know that you have a starting point with Kathleen basically be like, hey, here's where I am, but here's where I think.

ALEX: What do you think? Right. And, like working with somebody like that will make you go exponentially further than you're ever gonna go on your own. If there's one thing I wish I could have done, I have been at 10 years old to get a coach, let's put it that way. So, maybe a little young that was mom.

ALEX: So that's step one and step two. And step three is to commit to small daily actions.

ALEX: I find so many of us myself included. I wanna see exponential change every single day. It was something I actually heard James Clear talk about atomic habits is his book. And I was like, man, this guy is just like blown up. He must crush it every single day and he openly admits that he doesn't. He's like, I just want to be 1% better than I was yesterday.

ALEX: I'm like 1% better than yesterday. Like, that's hard to quantify, but also that's like, not a lot, right. But the reality is if you can just say today, I'm just gonna be a little bit better than I was yesterday. I'm gonna love a little bit better than I did yesterday. I'm gonna serve a little bit better. I'm gonna take care of myself a little bit better than I did the other day.

ALEX: If you can commit to that slow and steady wins the race and a lot of people going back to my own business people were like, how does Pod Match do so well, we just do a little bit every day to take better care of the people that we were taking care of yesterday and it seems to pay off over time. So that step three is commit to those small daily actions. Number four is to start helping somebody else.

ALEX: All of us feel like we're not far along to help somebody. But the reality is you can serve, you can help somebody. You can be the person that might be able to change their lives and you don't even know it. And so just commit to start helping somebody every single day, just say, you know what, I'm just gonna find one person to help to serve today.

ALEX: And the last thing I wanna say is just be, this is the fifth thing is to be patient with yourself. We're not trying to be perfect. The the reality is like perfection is just maybe a pipe dream. You're never really gonna get there, right?

ALEX: But the the thing is we can just be patient with ourselves and be ok when we have those down days and we have those up days, celebrate those wins with the people we love and care about. Mountain peaks and valleys there's a lot of those in our lives and in our journey. And if we can just say you want to be patient with me, not gonna be too hard on myself.

ALEX: I'm gonna find a way to just awaken every single day and go on this journey. I find that to be a beautiful thing. So that's kind of my thought and I know it's a little different than what normally is shared here, Kathleen. But thank you for giving me the opportunity to say all that.

KATHLEEN: Well, every bit of it is true and that's how I live my life is what you just did. I do that myself because I do need to do that. And when I don't know what to do, I just sit with a pen and paper and say, OK, I'm open to receive and I just allow it to come in.

KATHLEEN: I don't force it. I allow it, but I want to thank you so much Alex for coming on the show. This was so much fun. You're such a, you're a comedian. You are so funny how you tell stories.

ALEX: I never heard that before, but thank you.

KATHLEEN: No, you just made me laugh. I mean, you're just such a funny storyteller. So again, I want to thank you so much for being on the show today with us.

ALEX: Kathleen. Thank you for having me. What an honor.

KATHLEEN: You're welcome. And I just want to say thank you everyone. If you enjoyed the show today, please feel free to like and subscribe to the show. And also if you found value, please send this off to your friends and family because I think they might get a lot of good fun insight out of the show.

KATHLEEN: And, that, concludes our show for today. I look forward to seeing all of you next week and from my heart to yours. I hope you all have a fabulous week.