WEBVTT 00:00:00.000 --> 00:00:03.080 Welcome to Milestone Moments, the show where 00:00:03.080 --> 00:00:05.960 we explore the journeys that lead to success. 00:00:06.599 --> 00:00:10.220 I'm Sheila Slick, your host and founder of Five 00:00:10.220 --> 00:00:13.859 Milestones. In every episode, we will bring you 00:00:13.859 --> 00:00:17.100 insights from the minds of entrepreneurs, leaders 00:00:17.100 --> 00:00:20.820 and experts who will share not just their expertise, 00:00:20.879 --> 00:00:24.120 but the milestone moments that have reshaped 00:00:24.120 --> 00:00:27.059 their journeys and led to significant achievements. 00:00:27.960 --> 00:00:30.359 So if you're looking for motivation, you're in 00:00:30.359 --> 00:00:33.560 the right place. Subscribe now and discover the 00:00:33.560 --> 00:00:40.380 milestones that mark the path to success. Welcome 00:00:40.380 --> 00:00:43.659 to another episode of Milestone Moments in Business 00:00:43.659 --> 00:00:46.979 and Leadership. I'm your host, Sheila Slick. 00:00:47.259 --> 00:00:51.100 And today I have a super special guest, Alex 00:00:51.100 --> 00:00:56.119 Sanfilippo. He's the founder of the most groundbreaking 00:00:56.119 --> 00:01:00.539 tool for podcasters and people looking to be 00:01:00.539 --> 00:01:04.060 guests on other people's shows. It's called Podmatch 00:01:04.060 --> 00:01:07.920 .com. And through Podmatch and his podcast titled 00:01:07.920 --> 00:01:11.340 Podcasting Made Simple, Alex helps independent 00:01:11.340 --> 00:01:15.269 podcasters grow their influence. and their revenue 00:01:15.269 --> 00:01:18.629 so they can better serve their listeners. He's 00:01:18.629 --> 00:01:22.030 also co -author of Unscripted Brilliance, the 00:01:22.030 --> 00:01:24.810 Podmatch Edition. Welcome to the show, Alex. 00:01:25.400 --> 00:01:27.019 Sheila, thank you so much for the kind words. 00:01:27.140 --> 00:01:29.239 It seriously means a ton. At the time of recording 00:01:29.239 --> 00:01:30.760 this, we just got back from a conference that 00:01:30.760 --> 00:01:32.780 we were both at together. And it's funny when 00:01:32.780 --> 00:01:34.640 I walked into a couple of different people's 00:01:34.640 --> 00:01:36.819 presentations and not knowing they were going 00:01:36.819 --> 00:01:38.219 to talk about PodMatch, but they did. And I heard 00:01:38.219 --> 00:01:40.319 it described as like a dating app, but connecting 00:01:40.319 --> 00:01:42.260 people for podcast interviews instead of dates 00:01:42.260 --> 00:01:44.299 and like the Airbnb of podcasting. And I was 00:01:44.299 --> 00:01:46.280 like, wow, it's pretty cool. It was really fun 00:01:46.280 --> 00:01:50.040 to be able to see people without them being told 00:01:50.040 --> 00:01:52.340 to or asked to, but sharing about their experience 00:01:52.340 --> 00:01:54.480 with the platform. It seriously has been a gift. 00:01:55.019 --> 00:01:56.620 Getting to, as you said, connect guests and hosts 00:01:56.620 --> 00:01:58.760 for interviews and build all the little tools 00:01:58.760 --> 00:02:00.280 inside of it that really just help streamline 00:02:00.280 --> 00:02:01.760 the whole process. It's the whole idea is just 00:02:01.760 --> 00:02:03.579 let's save each other's time so we can do what 00:02:03.579 --> 00:02:05.540 we're doing right now, which is actually record 00:02:05.540 --> 00:02:07.040 something that's added value to the people that 00:02:07.040 --> 00:02:09.000 get to hear it. I'm just excited about it. I'm 00:02:09.000 --> 00:02:10.379 really glad to be able to serve in this way. 00:02:10.539 --> 00:02:13.460 I want to go back a couple years, that first 00:02:13.460 --> 00:02:16.719 entrepreneurial journey and that tough first 00:02:16.719 --> 00:02:19.120 entrepreneurial lesson you learned at a very 00:02:19.120 --> 00:02:21.860 young age. Sure. I mean, this is going back more 00:02:21.860 --> 00:02:24.180 than a couple years or a few years at this point, 00:02:24.219 --> 00:02:26.199 Sheila. This is going back a long time. But when 00:02:26.199 --> 00:02:28.719 I was 10 years old, that's actually when I got 00:02:28.719 --> 00:02:31.139 my first taste of entrepreneurship. At that point 00:02:31.139 --> 00:02:33.560 in my life, I was kind of a different kid. I 00:02:33.560 --> 00:02:35.000 wasn't great at school, but also wasn't good 00:02:35.000 --> 00:02:36.719 at video games or sports. And it's kind of like 00:02:36.719 --> 00:02:38.659 you had to be good at one of those things. But 00:02:38.659 --> 00:02:40.599 I wasn't like... I didn't have like a complex. 00:02:40.699 --> 00:02:42.360 I just knew I wasn't, I hadn't found my thing 00:02:42.360 --> 00:02:45.199 yet. And so one day I was outside playing on 00:02:45.199 --> 00:02:46.599 the golf course across the street from our neighborhood 00:02:46.599 --> 00:02:48.759 because all the parents said, go play anywhere 00:02:48.759 --> 00:02:50.180 you want except from the golf course. So all 00:02:50.180 --> 00:02:51.860 the kids ran to the golf course every day. And 00:02:51.860 --> 00:02:53.280 so we were just out there playing and there happened 00:02:53.280 --> 00:02:54.740 to be a golf ball sitting there, no golfers around. 00:02:54.860 --> 00:02:56.800 So I picked it up knowing really nothing about 00:02:56.800 --> 00:02:59.879 golf. A couple of minutes later, a golfer rode 00:02:59.879 --> 00:03:01.740 by in a cart and said, hey kid, what does that 00:03:01.740 --> 00:03:03.840 golf ball say on it? So I turned around and I 00:03:03.840 --> 00:03:06.580 said, it says Titleist Pro V1. And he goes, I'll 00:03:06.580 --> 00:03:09.479 give you $3 for it. Now listen, this is the 90s. 00:03:09.479 --> 00:03:11.400 Like in the 90s, $3 was a lot of money, especially 00:03:11.400 --> 00:03:13.620 for a kid. Like that was like light bulb. And 00:03:13.620 --> 00:03:14.979 this was the first time in my life I feel like 00:03:14.979 --> 00:03:17.159 something really clicked. So immediately I turned 00:03:17.159 --> 00:03:18.280 to the other kids because they're like, you just 00:03:18.280 --> 00:03:21.039 got $3, right? And I was like, here's what we're 00:03:21.039 --> 00:03:22.919 going to do. We watch golfers hit these balls 00:03:22.919 --> 00:03:24.520 in the water every day. We're going to fish them 00:03:24.520 --> 00:03:25.699 out. We're going to clean them up on Saturday 00:03:25.699 --> 00:03:26.879 morning. We're going to sell them right here. 00:03:27.219 --> 00:03:29.560 And long story short, I kind of started my first 00:03:29.560 --> 00:03:31.939 unofficial business. Never paid any taxes to 00:03:31.939 --> 00:03:34.000 Uncle Sam. I was a cute 10 -year -old kid so 00:03:34.000 --> 00:03:35.439 that I could get away with it for a little bit. 00:03:35.740 --> 00:03:38.360 But that was my real introduction. to entrepreneurship 00:03:38.360 --> 00:03:42.240 was just starting to sell things that creatively 00:03:42.240 --> 00:03:43.860 that I guess I was finding that were just kind 00:03:43.860 --> 00:03:45.819 of right there. And it seemed very obvious to 00:03:45.819 --> 00:03:47.740 me. And I didn't know that had any leadership 00:03:47.740 --> 00:03:50.020 potential as a 10 -year -old kid. I was bringing 00:03:50.020 --> 00:03:51.340 a bunch of kids in the neighborhood together, 00:03:51.500 --> 00:03:53.120 organizing them, making sure people showed up 00:03:53.120 --> 00:03:55.939 on time, all that stuff. And it kind of gave 00:03:55.939 --> 00:03:58.439 me, I guess, the entrepreneurial itch, like I 00:03:58.439 --> 00:03:59.900 caught the bug for it, right? And I found my 00:03:59.900 --> 00:04:03.060 thing. And that was my introduction to entrepreneurship. 00:04:04.840 --> 00:04:07.819 I love that. Mine was cookies at around seven 00:04:07.819 --> 00:04:10.780 years old and also had different life lessons. 00:04:10.860 --> 00:04:14.060 So why did you end up transitioning to corporate? 00:04:14.900 --> 00:04:17.279 Yeah, so I mean, my whole high school experience, 00:04:17.399 --> 00:04:19.019 I did a bunch of little things like you can only 00:04:19.019 --> 00:04:20.459 sell golf balls while you're cute. Once you're 00:04:20.459 --> 00:04:22.300 not cute, golfers like give me that ball. I hit 00:04:22.300 --> 00:04:25.220 in the lake yesterday. Right. So but I started 00:04:25.220 --> 00:04:26.860 selling things on eBay, got good on computers. 00:04:26.879 --> 00:04:29.920 So I did like even a little tech startup in the 00:04:29.920 --> 00:04:32.480 when I was my late teen years in the real estate 00:04:32.480 --> 00:04:35.439 space. And that kind of put me on the map as 00:04:35.439 --> 00:04:37.000 an entrepreneur. Like that was a real business. 00:04:37.060 --> 00:04:38.600 I was paying taxes with that one, right? Like 00:04:38.600 --> 00:04:43.920 doing all that. And then the recession hit. 2006, 00:04:44.860 --> 00:04:47.399 I was doing really well. 2007, 8, 9, like a lot 00:04:47.399 --> 00:04:48.699 of this is history for people. I don't want to 00:04:48.699 --> 00:04:50.879 revisit it myself even, right? But it was a bad 00:04:50.879 --> 00:04:52.920 time. And everything I was doing was in the real 00:04:52.920 --> 00:04:54.620 estate industry at that time. So I went from 00:04:54.620 --> 00:04:57.120 really thriving and doing well to doing really, 00:04:57.220 --> 00:05:00.540 really, really bad at that point. And I'll never 00:05:00.540 --> 00:05:03.199 forget this. I actually called my dad. And I 00:05:03.199 --> 00:05:05.920 was like, hey, I was like, I'm really struggling. 00:05:06.000 --> 00:05:07.500 I'm like, do you know of any work that's available? 00:05:07.980 --> 00:05:10.560 And my dad had a really big, he was a big name 00:05:10.560 --> 00:05:12.300 in the aerospace industry. So he's very well 00:05:12.300 --> 00:05:14.819 known, very high influence. And he's like, I 00:05:14.819 --> 00:05:16.939 can get you an interview somewhere. Yeah. And 00:05:16.939 --> 00:05:18.839 to this day, I'm very grateful. Like, I don't 00:05:18.839 --> 00:05:20.100 know where I would have been without that, but 00:05:20.100 --> 00:05:21.939 sure enough, I go to a company, I interview, 00:05:22.040 --> 00:05:24.300 I get a part -time job. So I would go from like 00:05:24.300 --> 00:05:26.480 a thriving entrepreneur, having fun, feeling 00:05:26.480 --> 00:05:29.300 like I'm like in my calling to financially really 00:05:29.300 --> 00:05:31.680 in a bad place to getting a part -time job at 00:05:31.680 --> 00:05:34.519 an aerospace company. And I was a receiving clerk, 00:05:34.560 --> 00:05:36.399 which was translation for, I took out the trash 00:05:36.399 --> 00:05:38.680 and broke down boxes for people. And that's kind 00:05:38.680 --> 00:05:41.399 of, that was my introduction to corporate. It 00:05:41.399 --> 00:05:42.699 was one of those things that felt like a necessity. 00:05:42.819 --> 00:05:45.379 Like I didn't want. Sheila, I didn't want to 00:05:45.379 --> 00:05:47.959 leave being an entrepreneur, but I was really 00:05:47.959 --> 00:05:50.379 like that really hurt. So I went from doing those 00:05:50.379 --> 00:05:52.860 things as a kid in high school. Right. It felt 00:05:52.860 --> 00:05:54.779 like success after success after success when 00:05:54.779 --> 00:05:56.639 the stakes were really low. Right. And then my 00:05:56.639 --> 00:05:59.240 first high stakes thing turned to this huge failure, 00:05:59.360 --> 00:06:01.079 which, again, it was out of my control. It was 00:06:01.079 --> 00:06:03.519 it was a recession. Right. But that scared me 00:06:03.519 --> 00:06:04.959 enough to be like, OK, I'm just going to get 00:06:04.959 --> 00:06:08.040 a job. And so I did 15 years in big corporate 00:06:08.040 --> 00:06:10.600 working in an aerospace company. And by the way, 00:06:10.660 --> 00:06:12.720 I never turned into an astronaut, skydiver, or 00:06:12.720 --> 00:06:14.600 fighter pilot. So it was a parts manufacturing 00:06:14.600 --> 00:06:16.579 company focused below the atmosphere. And that 00:06:16.579 --> 00:06:18.379 being a job I really loved and learned a lot 00:06:18.379 --> 00:06:21.439 from, but I just knew in my heart that was never 00:06:21.439 --> 00:06:22.980 going to be my life's calling or something I 00:06:22.980 --> 00:06:25.560 was going to stick with forever. So how did you 00:06:25.560 --> 00:06:28.720 start podcasting? Or did you go to PodFest to 00:06:28.720 --> 00:06:31.639 see if you wanted to be a podcaster? How did 00:06:31.639 --> 00:06:35.600 that fit into the picture? So I still had like 00:06:35.600 --> 00:06:38.339 all these entrepreneurial, I guess, feelings 00:06:38.339 --> 00:06:40.639 while I had this corporate job, right? And I 00:06:40.639 --> 00:06:42.379 learned the idea of having a side hustle. And 00:06:42.379 --> 00:06:45.199 so for me, I got married in 2012. And at that 00:06:45.199 --> 00:06:46.639 point was kind of when I was starting to feel 00:06:46.639 --> 00:06:49.199 like, oh, I really want to get back into some 00:06:49.199 --> 00:06:51.350 entrepreneurial stuff, but I don't want to. do 00:06:51.350 --> 00:06:53.430 anything risky because last time I failed, right? 00:06:53.529 --> 00:06:55.050 It was kind of my mindset. I was like this idea 00:06:55.050 --> 00:06:57.209 of a side hustle where I can apply myself for 00:06:57.209 --> 00:06:59.910 40 hours a week and a couple hours a day, I can 00:06:59.910 --> 00:07:02.189 do something for myself. And so I started a whole 00:07:02.189 --> 00:07:03.850 bunch of things, Sheila, like a whole bunch of 00:07:03.850 --> 00:07:05.870 different things. Like I started blogging back 00:07:05.870 --> 00:07:08.209 when, before it was like really podcasting. I 00:07:08.209 --> 00:07:10.290 did some coaching, some speaking, like all these 00:07:10.290 --> 00:07:12.990 different kinds of things. And then I found podcasting 00:07:12.990 --> 00:07:15.430 and taught myself how to do it. It was just very 00:07:15.430 --> 00:07:18.730 interesting. And I decided to just launch a show. 00:07:18.769 --> 00:07:22.199 And so I launched a show. I'm not 2014 maybe 00:07:22.199 --> 00:07:24.220 the years always get blurry, but something along 00:07:24.220 --> 00:07:26.120 those lines is when I launched it It was just 00:07:26.120 --> 00:07:28.160 kind of like a hobby thing on the side, but I 00:07:28.160 --> 00:07:29.899 started realizing was actually getting some real 00:07:29.899 --> 00:07:32.389 traction And so it made me decide to actually 00:07:32.389 --> 00:07:35.250 to pivot and do a show that had a lot of intention 00:07:35.250 --> 00:07:39.170 around it. And so it was 2017 or 2018. And I 00:07:39.170 --> 00:07:40.750 launched a show that actually did very, very 00:07:40.750 --> 00:07:43.829 well. In 2017, my kind of when that all was happening 00:07:43.829 --> 00:07:45.569 is my first time I went to Podfest in Orlando, 00:07:45.769 --> 00:07:47.209 which is a, for everyone listening who doesn't 00:07:47.209 --> 00:07:48.490 know what it is, a big podcasting conference, 00:07:48.589 --> 00:07:49.810 the one I referenced a little while ago that 00:07:49.810 --> 00:07:51.589 we just came back from. I've been going every 00:07:51.589 --> 00:07:54.569 year since 2017. Well, when I got there, that 00:07:54.569 --> 00:07:58.060 was my first. real opportunity to be around podcasters. 00:07:58.379 --> 00:08:00.560 Like I was one myself and it's funny back then 00:08:00.560 --> 00:08:02.019 you were a dork for podcasting. People were like, 00:08:02.060 --> 00:08:03.620 wow, that's super dorky, but your content's great. 00:08:03.720 --> 00:08:05.139 Right? Like, but I was like, well, there's a 00:08:05.139 --> 00:08:06.600 whole bunch of nerds that get together and talk 00:08:06.600 --> 00:08:09.060 about podcasting. And I just fell in love with 00:08:09.060 --> 00:08:11.139 the community of podcasting. Like I really did. 00:08:11.379 --> 00:08:13.220 I went home and just like knew, like, I want 00:08:13.220 --> 00:08:15.139 to keep on doing this podcasting thing. I've 00:08:15.139 --> 00:08:16.800 now got a little community. I'm going to love 00:08:16.800 --> 00:08:18.639 up my tools. My show that's starting to do well 00:08:18.639 --> 00:08:20.019 is going to do really well now because I feel 00:08:20.019 --> 00:08:22.740 more equipped and educated to be able to make 00:08:22.740 --> 00:08:25.910 it actually work well. And that's, That's kind 00:08:25.910 --> 00:08:27.490 of my introduction to getting into podcasting. 00:08:27.509 --> 00:08:29.089 And this was all side hustle. I had a full -time 00:08:29.089 --> 00:08:32.309 job the whole time I was doing this. A hobby. 00:08:32.889 --> 00:08:38.110 And today you have paid hosts because you're 00:08:38.110 --> 00:08:41.429 also helping people monetize their podcast over 00:08:41.429 --> 00:08:44.990 $1 million. You've paid out, which I know is 00:08:44.990 --> 00:08:47.909 your goal in 2025 because you were holding a 00:08:47.909 --> 00:08:52.129 big celebratory poster up and we were all cheering 00:08:52.129 --> 00:08:55.690 you on. Thank you. And so that's quite an accomplishment, 00:08:55.850 --> 00:08:59.870 Alex. And you're changing people's lives, not 00:08:59.870 --> 00:09:02.330 only by sharing your message, but you've built 00:09:02.330 --> 00:09:06.409 way beyond Podmatch. You've built an entire ecosystem. 00:09:06.929 --> 00:09:09.970 And I see you, you know, continuing to grow. 00:09:10.049 --> 00:09:14.110 So what key piece of advice can you give to someone 00:09:14.110 --> 00:09:18.070 that perhaps is still trying things out or perhaps 00:09:18.070 --> 00:09:22.259 they feel I failed? How do I retry? Because you're 00:09:22.259 --> 00:09:26.340 the perfect story of how someone can find success 00:09:26.340 --> 00:09:30.679 after continuous trying or failures, if you were 00:09:30.679 --> 00:09:32.960 calling them, which they're not because each 00:09:32.960 --> 00:09:35.580 failure is just a lesson and it gets you to where 00:09:35.580 --> 00:09:38.460 you need to be. I love the way you just said 00:09:38.460 --> 00:09:41.919 that. Each failure is a lesson that's going to 00:09:41.919 --> 00:09:43.559 teach you to get to where you need to be. I think 00:09:43.559 --> 00:09:46.379 that's so well said. That's exactly what I had 00:09:46.379 --> 00:09:48.620 to learn. So there's a gap here, right? 2017, 00:09:48.919 --> 00:09:50.879 I launched a show that started doing really well. 00:09:51.019 --> 00:09:52.759 I started going to PodFest, had my full -time 00:09:52.759 --> 00:09:56.059 job. In 2020, I made the decision that I wanted 00:09:56.059 --> 00:09:58.480 to go full -time with podcasting. And I didn't 00:09:58.480 --> 00:10:00.080 just quit my job and like, all right, I'm a full 00:10:00.080 --> 00:10:02.419 -time podcaster. There was no real path to do 00:10:02.419 --> 00:10:05.039 that. And so being able to now pay podcasters 00:10:05.039 --> 00:10:06.840 over a million dollars, which I'm so grateful, 00:10:06.919 --> 00:10:08.600 like still pinch myself thinking about being 00:10:08.600 --> 00:10:10.519 able to do that. That didn't happen by accident. 00:10:11.100 --> 00:10:13.480 And I'll share that story and hopefully something 00:10:13.480 --> 00:10:15.440 that's really tactful for a listener today to 00:10:15.440 --> 00:10:17.679 be able to hear and implement. But what I decided 00:10:17.679 --> 00:10:20.440 to do is I went to PodFest again in 2020, knowing 00:10:20.440 --> 00:10:22.419 this is a room full of the people that I say 00:10:22.419 --> 00:10:25.019 I want to serve. They helped me get started. 00:10:25.100 --> 00:10:26.460 They helped me really find this area of passion. 00:10:26.559 --> 00:10:28.700 I believe this is where I want to go from corporate. 00:10:29.899 --> 00:10:31.659 I was on stage with about 2000 people. There 00:10:31.659 --> 00:10:33.980 was right before the world shut down. So there 00:10:33.980 --> 00:10:35.679 was 2000 of us in a room and I was finishing 00:10:35.679 --> 00:10:38.340 my talk from stage. I just said, hey, if anyone 00:10:38.340 --> 00:10:39.659 would just give me two minutes of your time, 00:10:39.779 --> 00:10:41.679 I'd love to give you a hug, meet you real quick. 00:10:41.720 --> 00:10:43.659 And I have just one question I want to ask. And 00:10:43.659 --> 00:10:45.539 to my surprise, hundreds of people lined up. 00:10:45.759 --> 00:10:47.940 And I was really grateful for that. I had pen 00:10:47.940 --> 00:10:50.860 and paper in hand. And I had one very key question. 00:10:51.320 --> 00:10:52.759 What is it that you're struggling with right 00:10:52.759 --> 00:10:56.169 now in podcasting? And the thing is, to kind 00:10:56.169 --> 00:10:58.450 of frame this whole thing, everyone kept on answering 00:10:58.450 --> 00:11:00.169 it and kept on telling me things. And I wrote 00:11:00.169 --> 00:11:02.629 down what I heard. And I heard 100 times the 00:11:02.629 --> 00:11:04.409 same thing, which is, Alex, I'm having trouble 00:11:04.409 --> 00:11:07.009 finding the right guest for my show. Or I can 00:11:07.009 --> 00:11:08.309 find people who want to be a guest on my show, 00:11:08.330 --> 00:11:10.690 but never the most ideal person. Or it takes 00:11:10.690 --> 00:11:13.090 too long to do this whole thing to book a guest. 00:11:13.429 --> 00:11:15.049 And I was like, that's the problem I want to 00:11:15.049 --> 00:11:16.950 solve. And what I learned during these years 00:11:16.950 --> 00:11:18.950 is just a four -step framework for entrepreneurship. 00:11:19.210 --> 00:11:21.570 One, find your area of passion. For me, as we've 00:11:21.570 --> 00:11:22.830 been talking about, like it was podcasting. I 00:11:22.830 --> 00:11:24.289 want to be in it. And then I started going to 00:11:24.289 --> 00:11:26.009 the events. Number two, that's step two, is to 00:11:26.009 --> 00:11:28.570 get into the community. So I found my passion. 00:11:28.690 --> 00:11:30.250 I got into the community. The next thing is to 00:11:30.250 --> 00:11:31.850 discover the problem they're struggling with. 00:11:32.490 --> 00:11:34.330 That's what they described, you know, putting 00:11:34.330 --> 00:11:36.250 a guest and host together. And the last thing 00:11:36.250 --> 00:11:38.629 is to offer the fastest possible solution. And 00:11:38.629 --> 00:11:40.629 so what I did that day, I went back at the end 00:11:40.629 --> 00:11:43.009 of my talk, came back to Jacksonville. So this 00:11:43.009 --> 00:11:44.929 is Orlando. I drove up to Jacksonville and just 00:11:44.929 --> 00:11:46.629 started whiteboarding it out and just said, if 00:11:46.629 --> 00:11:48.950 this were easy, what would this look like? Not 00:11:48.950 --> 00:11:50.470 if it were complicated, if it were difficult, 00:11:50.690 --> 00:11:52.230 any of that stuff. And I said, okay, if it were 00:11:52.230 --> 00:11:53.610 easy, what would it look like? And also, how 00:11:53.610 --> 00:11:55.570 do I not reinvent the wheel? So I thought about 00:11:55.570 --> 00:11:57.230 it. I'm like, oh, well, dating apps do it really 00:11:57.230 --> 00:11:59.610 well. Airbnb. These companies already match people 00:11:59.610 --> 00:12:01.889 together. They make that right connection. I'm 00:12:01.889 --> 00:12:03.690 like, that's what I want to be able to do is 00:12:03.690 --> 00:12:07.190 that. And so started developing. And fast forward 00:12:07.190 --> 00:12:08.950 six months, or sorry, three months, actually 00:12:08.950 --> 00:12:10.870 launched. And then six months after that is when 00:12:10.870 --> 00:12:13.590 I left my corporate job. And that's always a 00:12:13.590 --> 00:12:15.970 risk. It's always scary to leave a job like that. 00:12:16.029 --> 00:12:19.149 But my advice is this. Take courage because courage 00:12:19.149 --> 00:12:21.350 means being afraid than doing what you have to 00:12:21.350 --> 00:12:24.049 do anyway. If you think that there's something 00:12:24.049 --> 00:12:26.149 on the other side of what you're doing, take 00:12:26.149 --> 00:12:28.190 a calculated risk. Really think about it. Don't 00:12:28.190 --> 00:12:29.509 just say, oh, it's fun. I'm passionate. It's 00:12:29.509 --> 00:12:31.610 going to work. No, no. Make a roadmap. Really 00:12:31.610 --> 00:12:33.909 think about it. And then what you do is you sacrifice 00:12:33.909 --> 00:12:36.009 the good. For me, it was a great corporate job 00:12:36.009 --> 00:12:37.950 after 15 years for the sake of the potential 00:12:37.950 --> 00:12:41.769 great. Podmatch had no, there was no guarantee 00:12:41.769 --> 00:12:43.919 it was going to make it, right? But it could 00:12:43.919 --> 00:12:45.779 be great because I was like, one day we could 00:12:45.779 --> 00:12:48.299 pay podcasters a million dollars back through 00:12:48.299 --> 00:12:50.220 commissions because they're on the platform. 00:12:50.620 --> 00:12:53.100 That could be great. And there's real potential 00:12:53.100 --> 00:12:55.039 in making this happen. So for me, once again, 00:12:55.120 --> 00:12:58.059 it just took courage. I was afraid. I love my 00:12:58.059 --> 00:12:59.620 corporate job at that point. I cried on my last 00:12:59.620 --> 00:13:01.279 day when I was leaving. It was so sad to leave 00:13:01.279 --> 00:13:03.899 after 15 years. But it was something, again, 00:13:04.000 --> 00:13:06.519 I think I just knew that I knew that I knew I 00:13:06.519 --> 00:13:08.220 had to go back to entrepreneurship and I had 00:13:08.220 --> 00:13:09.860 to take this risk because there might have been 00:13:09.860 --> 00:13:11.860 something great on the other side. And here I 00:13:11.860 --> 00:13:14.929 am years later. saying it was completely worth 00:13:14.929 --> 00:13:16.830 it. I would make that same decision 10 out of 00:13:16.830 --> 00:13:19.730 10 times. Part of me will always miss that corporate 00:13:19.730 --> 00:13:21.730 life, but I think I'm doing what I was made to 00:13:21.730 --> 00:13:23.529 do right now. And I think that that's a risk 00:13:23.529 --> 00:13:26.909 that's worth taking. Beautifully said and kudos 00:13:26.909 --> 00:13:30.210 to you. So there are many people out there that 00:13:30.210 --> 00:13:34.490 right now perhaps fear AI. What roadblocks or 00:13:34.490 --> 00:13:38.029 obstacles did you have to overcome in order to 00:13:38.029 --> 00:13:40.809 be able to do such a great platform from the 00:13:40.809 --> 00:13:44.080 software perspective? Yeah. So, I mean, I brought 00:13:44.080 --> 00:13:46.679 in a co -founder from day one. So it's me, my 00:13:46.679 --> 00:13:48.379 wife and our business partner, Jesse. And we 00:13:48.379 --> 00:13:51.519 just evenly split the company, had the legal 00:13:51.519 --> 00:13:53.840 team that we contracted kind of draft that up. 00:13:53.860 --> 00:13:56.360 And he's a developer. But from day one, we realized 00:13:56.360 --> 00:13:57.980 that like AI was going to be the way to go. And 00:13:57.980 --> 00:13:59.720 this was, again, 2020. So before it was really 00:13:59.720 --> 00:14:01.559 mainstream, we just said, hey, we're going to 00:14:01.559 --> 00:14:04.019 start leveraging this AI thing. The thing for 00:14:04.019 --> 00:14:05.080 somebody who's like, oh, I'm kind of like that 00:14:05.080 --> 00:14:06.519 makes me nervous, makes me scared and stuff like 00:14:06.519 --> 00:14:09.470 that. You can turn any digital enemy into an 00:14:09.470 --> 00:14:12.389 ally pretty quick if you understand what it can 00:14:12.389 --> 00:14:15.509 do for you. So a lot of people are really scared 00:14:15.509 --> 00:14:16.889 of AI because like, oh, it's probably gonna take 00:14:16.889 --> 00:14:18.509 my job. It's like, well, how can it elevate your 00:14:18.509 --> 00:14:20.549 job instead of take it, right? It might be able 00:14:20.549 --> 00:14:22.350 to take what you're doing today, but how can 00:14:22.350 --> 00:14:24.830 you now leverage it to elevate what you're able 00:14:24.830 --> 00:14:27.990 to do, what you're able to deliver? And for us, 00:14:28.009 --> 00:14:30.169 we just knew like, we're gonna use AI, not because 00:14:30.169 --> 00:14:32.139 it's ever gonna replace what we do. but it will 00:14:32.139 --> 00:14:34.100 elevate what we're able to do. Like it'll take 00:14:34.100 --> 00:14:36.139 our limits and take them even further, stretch 00:14:36.139 --> 00:14:38.580 it to a new level. And especially in 2020, like 00:14:38.580 --> 00:14:40.019 not a lot of people were doing anything with 00:14:40.019 --> 00:14:42.320 AI at that point. So we just. Learn to harness 00:14:42.320 --> 00:14:44.580 it from day one. And I'll tell you what, people's 00:14:44.580 --> 00:14:45.960 minds were blown. They're like, you mean there's 00:14:45.960 --> 00:14:47.639 an AI that matched me and this person together? 00:14:47.960 --> 00:14:50.639 I was like, yeah, there is. You know, like that's 00:14:50.639 --> 00:14:52.860 how it works. Like that's the beauty of it. Now 00:14:52.860 --> 00:14:54.139 we don't have to have someone behind the scenes 00:14:54.139 --> 00:14:56.179 doing it or going through a hundred different 00:14:56.179 --> 00:14:58.120 options to find one good one. Like that's not 00:14:58.120 --> 00:14:59.940 a thing anymore. We don't have to do it. If we 00:14:59.940 --> 00:15:01.139 were just said, oh, AI is probably gonna be able 00:15:01.139 --> 00:15:03.500 to do this without us one day, then we probably 00:15:03.500 --> 00:15:05.340 would have missed our opportunity. And so I think 00:15:05.340 --> 00:15:07.299 for everybody, no matter what you do, there is 00:15:07.299 --> 00:15:09.460 a huge opportunity to leverage it in a really 00:15:09.460 --> 00:15:12.299 big way. Think of it as an extension of you as 00:15:12.299 --> 00:15:14.879 an ally, not a potential enemy or threat. Think 00:15:14.879 --> 00:15:17.019 about what it can do to elevate who you are. 00:15:18.019 --> 00:15:20.580 I love that. And I would also add, don't lose 00:15:20.580 --> 00:15:22.940 the human touch. Because one of the things that 00:15:22.940 --> 00:15:27.559 I absolutely love about your team and your platform 00:15:27.559 --> 00:15:32.059 is you always answer as human. You're very active. 00:15:32.120 --> 00:15:35.799 You connect not only with your users, right, 00:15:35.860 --> 00:15:39.059 the hosts and the guests. And so you're actively. 00:15:40.269 --> 00:15:43.330 involved in the community. It's not I'm getting 00:15:43.330 --> 00:15:46.409 answered by a chatbot. It's there's a human behind 00:15:46.409 --> 00:15:49.450 the AI and you do a wonderful job at that. Thank 00:15:49.450 --> 00:15:51.309 you for, you know, I just I have to add something 00:15:51.309 --> 00:15:53.350 because that is to me so, so important. What 00:15:53.350 --> 00:15:55.330 we've learned to do is we automate things with 00:15:55.330 --> 00:15:58.909 AI that don't have a human to human contact point. 00:15:59.169 --> 00:16:01.190 Example, at one point in my podcasting career, 00:16:01.230 --> 00:16:04.110 I was writing transcripts. I don't write transcripts 00:16:04.110 --> 00:16:05.710 anymore. But I'll tell you, if you send me an 00:16:05.710 --> 00:16:07.309 email, you are not going to get an AI response. 00:16:07.490 --> 00:16:10.399 That will be me. If it says Alex Sanfilippo on 00:16:10.399 --> 00:16:11.919 the signature, it is actually me writing up. 00:16:11.980 --> 00:16:15.200 Not a VA, not an EA, not an AI. And I believe 00:16:15.200 --> 00:16:17.720 in that. I wanted to free up my time to elevate 00:16:17.720 --> 00:16:20.000 the human experience within what we do. So AI 00:16:20.000 --> 00:16:21.179 is doing all the stuff in the background that 00:16:21.179 --> 00:16:23.059 has no human -to -human interaction, right? I 00:16:23.059 --> 00:16:24.600 love that you brought that up, Sheila. I think 00:16:24.600 --> 00:16:27.419 that that might be the most important piece of 00:16:27.419 --> 00:16:29.240 AI is the fact that it should elevate humanity, 00:16:29.460 --> 00:16:32.879 not take it from us. Oh, you got a new tagline 00:16:32.879 --> 00:16:37.379 too now. Thank you. So for someone that is tuning 00:16:37.379 --> 00:16:41.059 in that perhaps has never considered podcasting 00:16:41.059 --> 00:16:44.620 or perhaps wants to just try, you know, podcasting, 00:16:44.620 --> 00:16:48.639 what advice would you give them? The first thing 00:16:48.639 --> 00:16:50.179 I tell anybody who's thinking about getting into 00:16:50.179 --> 00:16:52.279 space, whether you're a host or a guest, is to 00:16:52.279 --> 00:16:54.980 ask yourself a question. Why do I want to do 00:16:54.980 --> 00:16:57.850 this? Listen, I know it's trendy. Podcasting 00:16:57.850 --> 00:17:00.370 is like going like crazy right now. And I'm really 00:17:00.370 --> 00:17:02.429 grateful to be part of that. But it doesn't mean 00:17:02.429 --> 00:17:04.309 that everyone needs to do it. And if you look 00:17:04.309 --> 00:17:06.069 at the data in podcasting, the amount of people 00:17:06.069 --> 00:17:08.210 that fail and quit on both sides of the microphone 00:17:08.210 --> 00:17:10.369 would blow your mind. I mean, the amount of people 00:17:10.369 --> 00:17:11.990 that make it to eight episodes as a guest or 00:17:11.990 --> 00:17:15.049 as a host is less than 40%. And so before you 00:17:15.049 --> 00:17:16.369 say, yeah, I want to do this. It sounds great. 00:17:16.430 --> 00:17:18.710 I get it. It sounds great. It sounds cool. But 00:17:18.710 --> 00:17:21.670 before that. Ask yourself internally, why do 00:17:21.670 --> 00:17:23.430 I actually want to do this? What is the purpose 00:17:23.430 --> 00:17:26.089 of it? If it's just to try something new, great. 00:17:26.210 --> 00:17:28.269 You can just know you might be one of those, 00:17:28.289 --> 00:17:30.269 like the stereotype, right? You might fit into 00:17:30.269 --> 00:17:33.829 that ratio there of the 60 % of people failing 00:17:33.829 --> 00:17:35.190 before they hit eight episodes, right? But if 00:17:35.190 --> 00:17:36.569 you're like, you know what? I have a message 00:17:36.569 --> 00:17:39.150 I want to get the world and develop that. Really 00:17:39.150 --> 00:17:40.869 think through it well. It doesn't need to be 00:17:40.869 --> 00:17:43.089 perfect before you launch a show or start being 00:17:43.089 --> 00:17:45.369 a guest on a podcast, but really, really know 00:17:45.369 --> 00:17:48.190 what you want. The next thing I'll share is know 00:17:48.190 --> 00:17:50.000 who you're going to speak to. Again, whether 00:17:50.000 --> 00:17:51.599 you're a guest or a host, you're speaking to 00:17:51.599 --> 00:17:54.160 a listener. So in that context of why you're 00:17:54.160 --> 00:17:55.420 launching in the first place, think about who 00:17:55.420 --> 00:17:56.920 is this going to help? Who is it going to serve? 00:17:57.200 --> 00:17:58.759 Who's going to make a laugh? Who's it going to 00:17:58.759 --> 00:18:01.339 inform? Who's it going to inspire? Think about 00:18:01.339 --> 00:18:03.440 these things really well. I think that when you 00:18:03.440 --> 00:18:05.039 have these two things right, there's no wrong 00:18:05.039 --> 00:18:07.059 way to podcast. There's no rules beyond that 00:18:07.059 --> 00:18:08.980 in my mind. If you can get these two things right 00:18:08.980 --> 00:18:11.819 from the start. I love that. I think everyone 00:18:11.819 --> 00:18:16.220 has a story. And stories can change lives. And 00:18:16.220 --> 00:18:19.180 so if you're looking to get into podcasting, 00:18:19.180 --> 00:18:22.240 I also suggest looking in a pod match if you're 00:18:22.240 --> 00:18:25.039 going to have guests, because it'll make your 00:18:25.039 --> 00:18:29.000 life a lot easier booking, scheduling, and keeping 00:18:29.000 --> 00:18:32.799 track, not just finding those guests. Yeah, thank 00:18:32.799 --> 00:18:34.019 you for that. I really appreciate you mentioning 00:18:34.019 --> 00:18:37.619 pod match. Well, I thank you so much for your 00:18:37.619 --> 00:18:39.920 time today and for joining me. Yeah, thank you, 00:18:39.940 --> 00:18:41.819 Sheila. This is a great show. I really love what 00:18:41.819 --> 00:18:42.960 you're doing with this. I've been a listener 00:18:42.960 --> 00:18:45.279 myself, and I've learned some things here as 00:18:45.279 --> 00:18:47.779 well, specifically from Paul Eric Pape, maybe. 00:18:47.839 --> 00:18:50.019 I can't remember his last name, but an incredible 00:18:50.019 --> 00:18:52.180 speaker. I learned about giving myself some micro 00:18:52.180 --> 00:18:53.799 rewards. I encourage everybody, like, go back 00:18:53.799 --> 00:18:55.339 and listen to past episodes of this show. If 00:18:55.339 --> 00:18:56.819 you're just now joining for this one with me, 00:18:56.980 --> 00:18:58.920 there's some really great stuff here. So seriously, 00:18:59.000 --> 00:19:00.160 just thank you for what you're doing for having 00:19:00.160 --> 00:19:02.740 me today. Oh, thank you. Do you know where I 00:19:02.740 --> 00:19:06.240 found that guest? I'm about to have a guest now, 00:19:06.339 --> 00:19:09.369 but I didn't know before you said that. Pod match. 00:19:09.750 --> 00:19:13.230 Very cool. Very cool. Thank you so much. Well, 00:19:13.309 --> 00:19:16.309 thank you all for joining us on another episode 00:19:16.309 --> 00:19:18.609 of Milestone Moments in Business and Leadership.