Welcome to Milestone Moments, the show where
we explore the journeys that lead to success.
I'm Sheila Slick, your host and founder of Five
Milestones. In every episode, we will bring you
insights from the minds of entrepreneurs, leaders
and experts who will share not just their expertise,
but the milestone moments that have reshaped
their journeys and led to significant achievements.
So if you're looking for motivation, you're in
the right place. Subscribe now and discover the
milestones that mark the path to success. Welcome
to another episode of Milestone Moments in Business
and Leadership. I'm your host, Sheila Slick.
And today I have a super special guest, Alex
Sanfilippo. He's the founder of the most groundbreaking
tool for podcasters and people looking to be
guests on other people's shows. It's called Podmatch
.com. And through Podmatch and his podcast titled
Podcasting Made Simple, Alex helps independent
podcasters grow their influence. and their revenue
so they can better serve their listeners. He's
also co -author of Unscripted Brilliance, the
Podmatch Edition. Welcome to the show, Alex.
Sheila, thank you so much for the kind words.
It seriously means a ton. At the time of recording
this, we just got back from a conference that
we were both at together. And it's funny when
I walked into a couple of different people's
presentations and not knowing they were going
to talk about PodMatch, but they did. And I heard
it described as like a dating app, but connecting
people for podcast interviews instead of dates
and like the Airbnb of podcasting. And I was
like, wow, it's pretty cool. It was really fun
to be able to see people without them being told
to or asked to, but sharing about their experience
with the platform. It seriously has been a gift.
Getting to, as you said, connect guests and hosts
for interviews and build all the little tools
inside of it that really just help streamline
the whole process. It's the whole idea is just
let's save each other's time so we can do what
we're doing right now, which is actually record
something that's added value to the people that
get to hear it. I'm just excited about it. I'm
really glad to be able to serve in this way.
I want to go back a couple years, that first
entrepreneurial journey and that tough first
entrepreneurial lesson you learned at a very
young age. Sure. I mean, this is going back more
than a couple years or a few years at this point,
Sheila. This is going back a long time. But when
I was 10 years old, that's actually when I got
my first taste of entrepreneurship. At that point
in my life, I was kind of a different kid. I
wasn't great at school, but also wasn't good
at video games or sports. And it's kind of like
you had to be good at one of those things. But
I wasn't like... I didn't have like a complex.
I just knew I wasn't, I hadn't found my thing
yet. And so one day I was outside playing on
the golf course across the street from our neighborhood
because all the parents said, go play anywhere
you want except from the golf course. So all
the kids ran to the golf course every day. And
so we were just out there playing and there happened
to be a golf ball sitting there, no golfers around.
So I picked it up knowing really nothing about
golf. A couple of minutes later, a golfer rode
by in a cart and said, hey kid, what does that
golf ball say on it? So I turned around and I
said, it says Titleist Pro V1. And he goes, I'll
give you $3 for it. Now listen, this is the 90s.
Like in the 90s, $3 was a lot of money, especially
for a kid. Like that was like light bulb. And
this was the first time in my life I feel like
something really clicked. So immediately I turned
to the other kids because they're like, you just
got $3, right? And I was like, here's what we're
going to do. We watch golfers hit these balls
in the water every day. We're going to fish them
out. We're going to clean them up on Saturday
morning. We're going to sell them right here.
And long story short, I kind of started my first
unofficial business. Never paid any taxes to
Uncle Sam. I was a cute 10 -year -old kid so
that I could get away with it for a little bit.
But that was my real introduction. to entrepreneurship
was just starting to sell things that creatively
that I guess I was finding that were just kind
of right there. And it seemed very obvious to
me. And I didn't know that had any leadership
potential as a 10 -year -old kid. I was bringing
a bunch of kids in the neighborhood together,
organizing them, making sure people showed up
on time, all that stuff. And it kind of gave
me, I guess, the entrepreneurial itch, like I
caught the bug for it, right? And I found my
thing. And that was my introduction to entrepreneurship.
I love that. Mine was cookies at around seven
years old and also had different life lessons.
So why did you end up transitioning to corporate?
Yeah, so I mean, my whole high school experience,
I did a bunch of little things like you can only
sell golf balls while you're cute. Once you're
not cute, golfers like give me that ball. I hit
in the lake yesterday. Right. So but I started
selling things on eBay, got good on computers.
So I did like even a little tech startup in the
when I was my late teen years in the real estate
space. And that kind of put me on the map as
an entrepreneur. Like that was a real business.
I was paying taxes with that one, right? Like
doing all that. And then the recession hit. 2006,
I was doing really well. 2007, 8, 9, like a lot
of this is history for people. I don't want to
revisit it myself even, right? But it was a bad
time. And everything I was doing was in the real
estate industry at that time. So I went from
really thriving and doing well to doing really,
really, really bad at that point. And I'll never
forget this. I actually called my dad. And I
was like, hey, I was like, I'm really struggling.
I'm like, do you know of any work that's available?
And my dad had a really big, he was a big name
in the aerospace industry. So he's very well
known, very high influence. And he's like, I
can get you an interview somewhere. Yeah. And
to this day, I'm very grateful. Like, I don't
know where I would have been without that, but
sure enough, I go to a company, I interview,
I get a part -time job. So I would go from like
a thriving entrepreneur, having fun, feeling
like I'm like in my calling to financially really
in a bad place to getting a part -time job at
an aerospace company. And I was a receiving clerk,
which was translation for, I took out the trash
and broke down boxes for people. And that's kind
of, that was my introduction to corporate. It
was one of those things that felt like a necessity.
Like I didn't want. Sheila, I didn't want to
leave being an entrepreneur, but I was really
like that really hurt. So I went from doing those
things as a kid in high school. Right. It felt
like success after success after success when
the stakes were really low. Right. And then my
first high stakes thing turned to this huge failure,
which, again, it was out of my control. It was
it was a recession. Right. But that scared me
enough to be like, OK, I'm just going to get
a job. And so I did 15 years in big corporate
working in an aerospace company. And by the way,
I never turned into an astronaut, skydiver, or
fighter pilot. So it was a parts manufacturing
company focused below the atmosphere. And that
being a job I really loved and learned a lot
from, but I just knew in my heart that was never
going to be my life's calling or something I
was going to stick with forever. So how did you
start podcasting? Or did you go to PodFest to
see if you wanted to be a podcaster? How did
that fit into the picture? So I still had like
all these entrepreneurial, I guess, feelings
while I had this corporate job, right? And I
learned the idea of having a side hustle. And
so for me, I got married in 2012. And at that
point was kind of when I was starting to feel
like, oh, I really want to get back into some
entrepreneurial stuff, but I don't want to. do
anything risky because last time I failed, right?
It was kind of my mindset. I was like this idea
of a side hustle where I can apply myself for
40 hours a week and a couple hours a day, I can
do something for myself. And so I started a whole
bunch of things, Sheila, like a whole bunch of
different things. Like I started blogging back
when, before it was like really podcasting. I
did some coaching, some speaking, like all these
different kinds of things. And then I found podcasting
and taught myself how to do it. It was just very
interesting. And I decided to just launch a show.
And so I launched a show. I'm not 2014 maybe
the years always get blurry, but something along
those lines is when I launched it It was just
kind of like a hobby thing on the side, but I
started realizing was actually getting some real
traction And so it made me decide to actually
to pivot and do a show that had a lot of intention
around it. And so it was 2017 or 2018. And I
launched a show that actually did very, very
well. In 2017, my kind of when that all was happening
is my first time I went to Podfest in Orlando,
which is a, for everyone listening who doesn't
know what it is, a big podcasting conference,
the one I referenced a little while ago that
we just came back from. I've been going every
year since 2017. Well, when I got there, that
was my first. real opportunity to be around podcasters.
Like I was one myself and it's funny back then
you were a dork for podcasting. People were like,
wow, that's super dorky, but your content's great.
Right? Like, but I was like, well, there's a
whole bunch of nerds that get together and talk
about podcasting. And I just fell in love with
the community of podcasting. Like I really did.
I went home and just like knew, like, I want
to keep on doing this podcasting thing. I've
now got a little community. I'm going to love
up my tools. My show that's starting to do well
is going to do really well now because I feel
more equipped and educated to be able to make
it actually work well. And that's, That's kind
of my introduction to getting into podcasting.
And this was all side hustle. I had a full -time
job the whole time I was doing this. A hobby.
And today you have paid hosts because you're
also helping people monetize their podcast over
$1 million. You've paid out, which I know is
your goal in 2025 because you were holding a
big celebratory poster up and we were all cheering
you on. Thank you. And so that's quite an accomplishment,
Alex. And you're changing people's lives, not
only by sharing your message, but you've built
way beyond Podmatch. You've built an entire ecosystem.
And I see you, you know, continuing to grow.
So what key piece of advice can you give to someone
that perhaps is still trying things out or perhaps
they feel I failed? How do I retry? Because you're
the perfect story of how someone can find success
after continuous trying or failures, if you were
calling them, which they're not because each
failure is just a lesson and it gets you to where
you need to be. I love the way you just said
that. Each failure is a lesson that's going to
teach you to get to where you need to be. I think
that's so well said. That's exactly what I had
to learn. So there's a gap here, right? 2017,
I launched a show that started doing really well.
I started going to PodFest, had my full -time
job. In 2020, I made the decision that I wanted
to go full -time with podcasting. And I didn't
just quit my job and like, all right, I'm a full
-time podcaster. There was no real path to do
that. And so being able to now pay podcasters
over a million dollars, which I'm so grateful,
like still pinch myself thinking about being
able to do that. That didn't happen by accident.
And I'll share that story and hopefully something
that's really tactful for a listener today to
be able to hear and implement. But what I decided
to do is I went to PodFest again in 2020, knowing
this is a room full of the people that I say
I want to serve. They helped me get started.
They helped me really find this area of passion.
I believe this is where I want to go from corporate.
I was on stage with about 2000 people. There
was right before the world shut down. So there
was 2000 of us in a room and I was finishing
my talk from stage. I just said, hey, if anyone
would just give me two minutes of your time,
I'd love to give you a hug, meet you real quick.
And I have just one question I want to ask. And
to my surprise, hundreds of people lined up.
And I was really grateful for that. I had pen
and paper in hand. And I had one very key question.
What is it that you're struggling with right
now in podcasting? And the thing is, to kind
of frame this whole thing, everyone kept on answering
it and kept on telling me things. And I wrote
down what I heard. And I heard 100 times the
same thing, which is, Alex, I'm having trouble
finding the right guest for my show. Or I can
find people who want to be a guest on my show,
but never the most ideal person. Or it takes
too long to do this whole thing to book a guest.
And I was like, that's the problem I want to
solve. And what I learned during these years
is just a four -step framework for entrepreneurship.
One, find your area of passion. For me, as we've
been talking about, like it was podcasting. I
want to be in it. And then I started going to
the events. Number two, that's step two, is to
get into the community. So I found my passion.
I got into the community. The next thing is to
discover the problem they're struggling with.
That's what they described, you know, putting
a guest and host together. And the last thing
is to offer the fastest possible solution. And
so what I did that day, I went back at the end
of my talk, came back to Jacksonville. So this
is Orlando. I drove up to Jacksonville and just
started whiteboarding it out and just said, if
this were easy, what would this look like? Not
if it were complicated, if it were difficult,
any of that stuff. And I said, okay, if it were
easy, what would it look like? And also, how
do I not reinvent the wheel? So I thought about
it. I'm like, oh, well, dating apps do it really
well. Airbnb. These companies already match people
together. They make that right connection. I'm
like, that's what I want to be able to do is
that. And so started developing. And fast forward
six months, or sorry, three months, actually
launched. And then six months after that is when
I left my corporate job. And that's always a
risk. It's always scary to leave a job like that.
But my advice is this. Take courage because courage
means being afraid than doing what you have to
do anyway. If you think that there's something
on the other side of what you're doing, take
a calculated risk. Really think about it. Don't
just say, oh, it's fun. I'm passionate. It's
going to work. No, no. Make a roadmap. Really
think about it. And then what you do is you sacrifice
the good. For me, it was a great corporate job
after 15 years for the sake of the potential
great. Podmatch had no, there was no guarantee
it was going to make it, right? But it could
be great because I was like, one day we could
pay podcasters a million dollars back through
commissions because they're on the platform.
That could be great. And there's real potential
in making this happen. So for me, once again,
it just took courage. I was afraid. I love my
corporate job at that point. I cried on my last
day when I was leaving. It was so sad to leave
after 15 years. But it was something, again,
I think I just knew that I knew that I knew I
had to go back to entrepreneurship and I had
to take this risk because there might have been
something great on the other side. And here I
am years later. saying it was completely worth
it. I would make that same decision 10 out of
10 times. Part of me will always miss that corporate
life, but I think I'm doing what I was made to
do right now. And I think that that's a risk
that's worth taking. Beautifully said and kudos
to you. So there are many people out there that
right now perhaps fear AI. What roadblocks or
obstacles did you have to overcome in order to
be able to do such a great platform from the
software perspective? Yeah. So, I mean, I brought
in a co -founder from day one. So it's me, my
wife and our business partner, Jesse. And we
just evenly split the company, had the legal
team that we contracted kind of draft that up.
And he's a developer. But from day one, we realized
that like AI was going to be the way to go. And
this was, again, 2020. So before it was really
mainstream, we just said, hey, we're going to
start leveraging this AI thing. The thing for
somebody who's like, oh, I'm kind of like that
makes me nervous, makes me scared and stuff like
that. You can turn any digital enemy into an
ally pretty quick if you understand what it can
do for you. So a lot of people are really scared
of AI because like, oh, it's probably gonna take
my job. It's like, well, how can it elevate your
job instead of take it, right? It might be able
to take what you're doing today, but how can
you now leverage it to elevate what you're able
to do, what you're able to deliver? And for us,
we just knew like, we're gonna use AI, not because
it's ever gonna replace what we do. but it will
elevate what we're able to do. Like it'll take
our limits and take them even further, stretch
it to a new level. And especially in 2020, like
not a lot of people were doing anything with
AI at that point. So we just. Learn to harness
it from day one. And I'll tell you what, people's
minds were blown. They're like, you mean there's
an AI that matched me and this person together?
I was like, yeah, there is. You know, like that's
how it works. Like that's the beauty of it. Now
we don't have to have someone behind the scenes
doing it or going through a hundred different
options to find one good one. Like that's not
a thing anymore. We don't have to do it. If we
were just said, oh, AI is probably gonna be able
to do this without us one day, then we probably
would have missed our opportunity. And so I think
for everybody, no matter what you do, there is
a huge opportunity to leverage it in a really
big way. Think of it as an extension of you as
an ally, not a potential enemy or threat. Think
about what it can do to elevate who you are.
I love that. And I would also add, don't lose
the human touch. Because one of the things that
I absolutely love about your team and your platform
is you always answer as human. You're very active.
You connect not only with your users, right,
the hosts and the guests. And so you're actively.
involved in the community. It's not I'm getting
answered by a chatbot. It's there's a human behind
the AI and you do a wonderful job at that. Thank
you for, you know, I just I have to add something
because that is to me so, so important. What
we've learned to do is we automate things with
AI that don't have a human to human contact point.
Example, at one point in my podcasting career,
I was writing transcripts. I don't write transcripts
anymore. But I'll tell you, if you send me an
email, you are not going to get an AI response.
That will be me. If it says Alex Sanfilippo on
the signature, it is actually me writing up.
Not a VA, not an EA, not an AI. And I believe
in that. I wanted to free up my time to elevate
the human experience within what we do. So AI
is doing all the stuff in the background that
has no human -to -human interaction, right? I
love that you brought that up, Sheila. I think
that that might be the most important piece of
AI is the fact that it should elevate humanity,
not take it from us. Oh, you got a new tagline
too now. Thank you. So for someone that is tuning
in that perhaps has never considered podcasting
or perhaps wants to just try, you know, podcasting,
what advice would you give them? The first thing
I tell anybody who's thinking about getting into
space, whether you're a host or a guest, is to
ask yourself a question. Why do I want to do
this? Listen, I know it's trendy. Podcasting
is like going like crazy right now. And I'm really
grateful to be part of that. But it doesn't mean
that everyone needs to do it. And if you look
at the data in podcasting, the amount of people
that fail and quit on both sides of the microphone
would blow your mind. I mean, the amount of people
that make it to eight episodes as a guest or
as a host is less than 40%. And so before you
say, yeah, I want to do this. It sounds great.
I get it. It sounds great. It sounds cool. But
before that. Ask yourself internally, why do
I actually want to do this? What is the purpose
of it? If it's just to try something new, great.
You can just know you might be one of those,
like the stereotype, right? You might fit into
that ratio there of the 60 % of people failing
before they hit eight episodes, right? But if
you're like, you know what? I have a message
I want to get the world and develop that. Really
think through it well. It doesn't need to be
perfect before you launch a show or start being
a guest on a podcast, but really, really know
what you want. The next thing I'll share is know
who you're going to speak to. Again, whether
you're a guest or a host, you're speaking to
a listener. So in that context of why you're
launching in the first place, think about who
is this going to help? Who is it going to serve?
Who's going to make a laugh? Who's it going to
inform? Who's it going to inspire? Think about
these things really well. I think that when you
have these two things right, there's no wrong
way to podcast. There's no rules beyond that
in my mind. If you can get these two things right
from the start. I love that. I think everyone
has a story. And stories can change lives. And
so if you're looking to get into podcasting,
I also suggest looking in a pod match if you're
going to have guests, because it'll make your
life a lot easier booking, scheduling, and keeping
track, not just finding those guests. Yeah, thank
you for that. I really appreciate you mentioning
pod match. Well, I thank you so much for your
time today and for joining me. Yeah, thank you,
Sheila. This is a great show. I really love what
you're doing with this. I've been a listener
myself, and I've learned some things here as
well, specifically from Paul Eric Pape, maybe.
I can't remember his last name, but an incredible
speaker. I learned about giving myself some micro
rewards. I encourage everybody, like, go back
and listen to past episodes of this show. If
you're just now joining for this one with me,
there's some really great stuff here. So seriously,
just thank you for what you're doing for having
me today. Oh, thank you. Do you know where I
found that guest? I'm about to have a guest now,
but I didn't know before you said that. Pod match.
Very cool. Very cool. Thank you so much. Well,
thank you all for joining us on another episode
of Milestone Moments in Business and Leadership.