Ep. 13-Zachary Babcock: Underdog Empowerment "From Prison to Passive Income"

In this episode of the You Winning Life podcast, host Jason Wasser interviews Zachary Babcock, the founder of the Underdog Empowerment podcast. Zachary shares his personal transformation from a troubled youth who lost his father, fell into crime, and spent multiple years in prison to becoming a successful podcaster and entrepreneur. He explains how a decisive moment in jail sparked his commitment to change, the struggles he faced after release—including failed network‑marketing stints and a period of financial desperation— and how he eventually launched the Underdog Empowerment podcast, which quickly rose into the top‑200 iTunes rankings. The conversation pivots to practical guidance for aspiring podcasters: the importance of authenticity over hype, the “4 W’s” framework (what the podcast is about, who it serves, why it matters, and how to present it), and the necessity of mastering a skill through a three‑phase mastery model (novice, practitioner, master) complemented by mentorship. Zachary also recounts a misaligned partnership with a lead‑generation program, his decision to quit it on principle, and how that honesty deepened audience trust. He emphasizes that genuine value, clear positioning, and consistent delivery turn a podcast into a powerful networking engine, citing collaborations with high‑profile entrepreneurs like Andy Frisella, Gary Vaynerchuk, and John Lee Dumas. The episode closes with Zachary directing listeners to underdogempowerment.com and reflecting on the phoenix metaphor of rising from ashes, reinforcing the theme of underdog empowerment.
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This is the You Winning Life podcast, your number one source for mastering a positive existence. Each episode, we'll be interviewing exceptional people, giving you empowering insights and guiding you to extraordinary outcomes. Learn from specialists in the worlds of integrative and natural wellness, spirituality, psychology, and entrepreneurship so you too can be winning life. Now here's your host, licensed marriage and family therapist, certified neuro-emotional technique practitioner, trainer and certified entrepreneur coach, Jason Wasser.
All right, welcome back to the You Winning Life podcast. I'm here with a really, really incredible guest. From convicted felon to host of a highly rated podcast, Underdog Empowerment. His mission is helping other underdog entrepreneurs get and keep attention while taking them to the next level. Really would like to welcome Zachary Babcock to the show today. Thanks, Zach. What's going on over there?
What's going on, Jason? Thanks for having me, man.
Oh, it's an absolute pleasure. So I know one of the things that I absolutely completely love about your story reminds me of the concept of the mythical figure, the phoenix. And I'm sure you've been— that's been brought to your attention before, but if not, you know, what's the first thing that comes to your mind about that concept and that idea when it comes to your journey in your life?
You know, that's really the first time it has been brought. That's pretty cool though. Are you— so like how I know about that, a little bit of the mythical creature. Like, the only thing is I heard that song by Fall Out Boy, uh, you know, uh, something where he's like, it's about rising up, basically. Yeah, the whole concept.
Yeah, it's rising up from the dashes, right? The ashes. It's this thing that, right, it's a, it's kind of a bird that, that meets its demise, and then from its own ashes it rises up again, but a better, stronger, more powerful version. And it's this constant reincarnation, uh, along its own path and journey.
I shouldn't have named my podcast Underdog Empowerment. I should have called it The Phoenix.
That's the next project we can collaborate on together.
Yeah.
So, tell us a little bit because the idea of this, the odds that are stacked against us, and I know one of the things that you focus on, right, using that word underdog and empowerment is something that's very consistent in your messaging. So, talk to me about how that fits for you, what you're trying to do with that in your own personal life, and how you're trying to share that mission and message with other people.
Yeah, man, absolutely, dude. I'll keep this story as short as possible. We all have long stories, but, uh, yeah, man, I, um, you know, I, I made a bunch of poor choices growing up. Uh, I always wanted to fit in with the crowd. We all do to an extent because we're social creatures, you know, I get it. But I took it overboard. And, um, anytime that wasn't accepted or something, it would really get to me. And this, I guess, stems from not having a father figure. He died when I was 7. And so, by the time I was 19, I landed myself in prison. I did over 4 years flat the first time. I learned a lot, a lot of hard lessons in there and I got out for 2 years and then, I went back just 20 days before my twin sons were born. And Jason, that was the straw that broke the camel's back. I was done. It was enough was enough. And I made a decision right there in that jail cell before I even landed in prison. That I was going to turn my life around and make it happen some way, somehow. I didn't know how but had strong reasons why I was going to do it. And, you know, long story short, I got out, couldn't find a job anywhere. I did network marketing for about 2 years, but it just wasn't my thing. It wasn't my passion. And I started despising how I was taught to network with people and build my company. And so I moved on from that and got into coaching, struggled for over a year and a half. Then, it was literally like, it was like to the breaking point like, "Oh my God, how am I going to feed my family?" It was rough. And then, I remember I would always try to collaborate with other entrepreneurs and other people and, you know, do JVs or figure out ways to, you know, help each other out. Nobody ever wanted anything to do with me. I was just some ex-convict turned entrepreneur afterthought that nobody gave the time of day to. And so, out of that frustration, out of that pain, out of that anger, out of everybody counting me out, I decided to create the Underdog Empowerment Podcast. And we became a top 200 rated podcast in the first week. And then the next week, I was interviewing Billy Genius Marketing on my show. And it's just been everybody that's came on ever since. It's just been a constant spiral of upwards momentum. But it's crazy to think about the week before, nobody wanted anything to do with me. And then right afterwards, you know, this— the podcast really changed the game for me and kind of got me really rolling and really dialed into what I'm doing now.
That's incredible. What do you think it is that really allowed people out there to stop seeing the old story and to start seeing you as who you are in present day?
Really, I really feel like it was more of less talk and just doing, because I would always— I used to be the guy that was like, hey, I'm gonna do this, or I'm gonna do that, and talk about my goals all the time. And which, it's cool to put it out there and or whatnot, but I don't really do that hardly ever anymore. It's really just showing. I show more than I tell. And I think that's when people started seeing the results like, "Darn, you know, look at these interviewing Billy Jean and he's got Andy Frisella and like so on and like dang, he's helping all these other people launch a podcast." That's when it's really started setting in like, "Okay, you know, he's for real now." Yeah, and I think that in this world today of these new young entrepreneurs, there's a lot of that big talk.
And no backing up the process with an actual substantial substance and product. So, in your, right, your experience now, you're helping other entrepreneurs find their voice, you're helping them build podcasts and actually get a brand. What's the one thing that you would instruct someone who's really trying to identify their passion and their voice when it comes to being able to put that out there so they actually have something to represent and stand behind?
Yeah, man, absolutely. I'm glad you asked that. So that's, uh, the main, like, the most important piece of anybody that I work with to help them launch their podcast. Like, yeah, it's cool to learn all the ninja hacks of, you know, guaranteeing you get on the top 200 rated on iTunes, or interviewing celebrities, or, uh, directly monetizing your podcast, making $1,000 or more per month, or directly growing by 1,000 new downloads each and every month. All that stuff is cool and it's great and that's exciting, But the most important piece to all that, because none of that's sustainable and you won't be able to reach on that if you don't have what I call the 4 W's dialed in. And what that is, is a really short, very short and condensed version of this because this could take about 5 minutes by itself just to dial it in. But I'm going to really shorten it up for you. But it really is, what is your podcast about? Be able to communicate that in one sentence or fewer. It's just like good communication. You can relate it to baseball. A bad throw in baseball costs you a run or two or could potentially cost you the game. Same thing with what it is your podcast about. When you're communicating that in your show description, people land on you through a keyword on iTunes. iTunes is the third largest search engine in the world next to Google and YouTube. They land on you and they like your podcast artwork. That's the first thing they see. So if they don't know you, then the next thing they're gonna do is they're gonna read your show description before they even give you a chance to check you out. And if you don't communicate what it is that your podcast is about in that show description very clearly, then they're going to keep on moving. Just like when people land on your website and you heard of the term bounce rate where people leave right away. They immediately form that opinion of you and if it doesn't resonate, they keep going. So hit on the what. What is it that your podcast is? Know exactly what it is. Next, you got to know who it is that you're talking to. You know, obviously, if you don't have an audience, you're speaking into a microphone full of air. So get clear on exactly who it is that your podcast is for. In my example, Underdog Empowerment is for underdog entrepreneurs, people that have all the odds stacked against them, everybody counting them out, even laughing at them, but they don't care. They're committed to doing whatever it takes to win and to level up. That's who I serve. So you might be, you might be in e-commerce. I'm just going to give a hypothetical situation. And in e-commerce, it's just like in business, you got to create that customer avatar. Same in podcasting, but in e-commerce, You might have multiple audiences. You might have an audience that likes expensive pens or expensive phone cases or t-shirts, and you don't necessarily have to be the face of the business. You could just run ads and make money. It's similar in podcasting except for you are the face, you're the voice of the podcast, and people are tuning in because of you.
They want—
they don't necessarily have to like you, but they're tuning in because they want to hear your thoughts, perspectives, and views on things. So it's— and, and the best way to do that then is to just be yourself and speak to who you were yesterday and not act further along than what you really are. And it's perfectly fine to say, "Hey, I don't have all the answers, but I'm sticking my neck out on the line every single day and I'm bringing you a lot of people that do have a lot of the answers that we're looking for right here on this podcast." So, that's really important to do that, you know, and I do that online too.
That's amazing because it sounds exactly like, from my perspective as a therapist and a coach, right, bringing out the that inner voice that everybody, you know, I'm finding over and over again. So many of my clients, so many of my colleagues have that imposter syndrome, that fear of like, what do I really know? Wham, if they find out that I don't know it all. And you and I both know this, and the listeners should know this, that we're not expected to know it all. We're just supposed to know a little bit more in the area that they're turning to us for help in, right?
Amen, dude. Absolutely. It's so critical, dude. And that's like you kind of going back piggybacking what you're saying before, you know, where this day and age there's so many people that are a lot of talk and no show. It's true. I mean, look at it. Look at the internet, man. It's so— I get disgusted. And I say this because I did it myself and I learned from this the hard way. And hopefully, you don't have to do this. And when you act further along than what you really are, and especially if you're promising something that you can't deliver, you look like a a douchebag and a scumbag and a parasite. And here's the deal, man. It's, it's, it's gonna hurt you more in the long run. What I did, man, is when I launched the podcast, when I was, uh, trying to figure out this, the service that I could provide to people, yeah, I teamed up with a guy named Brett and Lee. And Brett had this awesome program for lead gen, customer acquisition, customer acquisition, and, uh, scaling a business. And this program had over 1,000 successful graduates and did over $20 million in revenues total. And so I was like, man, wow, this is an awesome program.
It works.
And so we repurposed it and we're bringing it to my audience with me being the face of it. And we're bringing people through this program. However, at the time, I was flat broke. And so it was backwards. I was trying to achieve what we're teaching by teaching it. And so it was just, it wasn't cool and it just didn't resonate with my values and my integrity. And over time, I finally pulled the plug on it. And on December of 2018, on Christmas Day, I made a post and I said, I called myself out on it. I was like, hey dude, look, I'm doing this. Yeah, it's a proven program, but still I feel like an imposter. I shouldn't be doing this. I'm quitting. We're not doing this no more. I'm going back to the drawing board. I'm gonna figure something else out. And that was hard to do, but it was one of the best things to do. And it built a really strong relationship with my audience. They're like, "Wow, this is a real dude," you know? And so—
And that's where the authenticity comes through, right? When you're listening to someone like Andy Frisella or Gary Vaynerchuk, right? There's people out there that they bring their authenticity. And I think that's the vein that people like you and I are trying to bring to the table. You know, one of my biggest frustrations as a business owner is that I'm providing a direct service, and truly those of us who have a brick— whether you're brick and mortar, whether you're digital-based like you are, and you're providing product that goes back out on the internet, you actually have a business. But I'm sure you can agree with me that how many people out there call themselves entrepreneurs? They don't have a business, they're just repackaging or selling a product from somebody else's company. That doesn't, in my mind, that doesn't make you an entrepreneur. It makes you entrepreneurial. But it doesn't make you an entrepreneur. And I'm wondering what your thoughts are on that.
I mean, I agree with you, bro. And I used to be that entrepreneurial person. I started off in network marketing and then, just, I mean, even if you're just doing information product, it's still like, you know, come on, man. It's like, there's a lot more, you gotta be a lot more adapt to business if you're doing a brick and mortar. You gotta have some really, some major skills to make that happen. Like with mine, like, so I do a lot of information as far as like, you know, showing people how to launch a podcast and monetize it and grow it, all that good stuff. But I also have a production agency where we actually have a service we offer where we produce your podcast for you so you're not stuck spending all this time producing it yourself. And so you can actually focus on marketing and growing your own business in the process. So it's like twofold. So yeah, I agree with you 100%, man. Like, find something that you can deliver that's tangible and like a service or product and, you know, just go with it, man.
Yeah, completely, completely in alignment with that one. So as we wrap up, I kind of have this question. It's my on one foot question, right? So if you can teach everybody out there just one thing, and this is the only thing that they can ever get from you, right? That one bit of data. That you hope will change their life? What would that be?
I love this question, bro. So, what I have, it's one thing but there's like 3 phases to it. And it's like, it combines— so, you have to do this. This is the only way I feel like— if I could go back and tell myself this when I was just starting out as entrepreneur, this is what I would tell myself. It would be, first and foremost, you can't act further along than what you really are. And— The reason why is because you're going to hurt your reputation and it's not going to line up with your character if you have a good character, for one. And also, it's going to hinder you because when you act further along than what you really are, just like with the underdog mentality where it's like some underdogs are thinking like, oh, they're counting me out. I'm going to prove them wrong. I am better than what they say I am. But you're not. You're not better than what they say you are. You are what they say you are because that's the reason why you're underdog in the first place. So you got to realize where you're at so you know that you can and get better from there. And then the second piece of it is to do the work, man. And what I mean by that is to actually master a skill. Everybody wants to take all these shortcuts and stuff. And I know this ain't the sexy answer, but this is the real thing. Anybody that's achieved anything of significance, they became a master at it. And so there's 3 phases to that. You begin— when you enter an industry, you're from the outside looking in. You know nothing about it. You don't know how the social dynamics work. You don't know none of the rules. You don't know the skills. You suck. All this stuff. And then you move to the second phase where you started practicing and learning these skills and developing. Now you know how everything operates. And so you become a practitioner at that point. You begin to try out your ideas and learning them. And then you finally move to the third phase, usually after 10,000 hours or more of honing the skill so much that you develop the skill to a point where you've mastered it, where you've internalized it, where you no longer have to think about it, where you can begin to manipulate, bend, and break, and make new rules and the process. And that's when you truly master something. That's when you have something of value to offer to the marketplace. And then finally, to tie all that in together, to speed track all of that, find somebody that— this is the nugget. Like, I know of no faster— I use the word shortcut. There's no shortcuts. You're still going to have to do the work. But no faster shortcut, no faster way to streamline this than to find somebody that already has what you want. And become a student of theirs. Whether you have to give them money, whether you barter services, or whether you connect them with someone in your network that would be very valuable to them. Whatever it is that you got to do, find a way to give them value in order to become their student. And that's the fastest way I know to really level up in any, anything, any career, any place in life.
You're so spot on. Last night I was listening to a Gary Vee and he was talking about, right, no one who's become successful did it easily. I mean, there are people who like got super lucky with an investment or maybe got in early on Bitcoin, but they still took a major risk in doing that, and taking that risk for a lot of people isn't easy. But when you just talked about that 10,000 hours, that Malcolm Gladwell research, right? Me as a therapist, I graduated 2005 from graduate school. Just to get licensed from the time we started graduate school till the time after we had our postgraduate internship hours, we had 2,000 hours alone of clinical hours just to get licensed. And between now and then, you know, I do about 1,000 sessions, client sessions a year, 45, 60, 90-minute sessions. So, and I've been practicing right now for over 10 years. So, that's 10,000 hours plus. And you have these people out there, you know, wake up tomorrow and like, "I want to be a coach," and they open up a business and they start advertising. It's really scary out there. The risks that people are taking with other people's lives and people that are taking with themselves by not doing their due diligence to see what are these people offering and what's their real background. Because, right, my field, the barrier to entry is a state license and a graduate degree and a minimum of supervision and case consultation and ethics. But you have people out there who literally wake up tomorrow and say, "I want to be a coach," and open up a business. You're really, really spot on of who is out there that's actually mastering their craft. And there's a lot of smoke and mirrors. And I think the beautiful thing about what you're doing is you're helping people break through the smoke and mirrors, and helping them realize that it is a process to be successful, to really be winning life. And I really think that it's a beautiful thing that you're honing in on that. And that's why I really like this idea of the Phoenix, right, going back to the beginning, for you, where you're helping people recraft that as the way you crafted yours. Own life and your own story.
Amen, bro. Appreciate that. Amen.
Well, for those out there who for the first time are hearing you, where can they track you down and get in touch with you?
Yeah, man. Dude, I'm really passionate about the podcast as well. If you guys enjoyed this interview, man, come check it out. It's Underdog Empowerment. You can check it out literally on any podcast platform that you listen to, that you're listening to this one right now. To make it easy for you, just go to underdogempowerment.com and right there on the front page, I got all the different platforms, iTunes, Spotify, Google Play, Stitcher, whichever one you prefer. Hope to see you over there and thank you, Jason Wasser.
My pleasure. And thanks for hanging out. And the beautiful thing is that you just had two major interviews, right? With some big players in the entrepreneur world. So, if you just wanna mention that quickly.
Yeah, man. It's crazy. Like I mentioned before, nobody wanted to collaborate with me and now, it's consistently like a couple times a month, we're flying out to each other. Either go see Andy Frisilla or Brad Lee or Ryan Stewman or Casey Adams, John Lee Dumas, you name it. Just, it's crazy how much doors the podcast was able to help me unlock as far as networking and being able to build those relationships with some good people, man.
Cool.
That's awesome. Well, I look forward to hearing much more of your successes as we continue, both of us along this journey. And for anybody out there that has any questions, obviously feel free to reach out to either one of us., and, uh, we look forward to catching you on the next episode. Thanks again, Zach, for checking in and hanging out with us.
Thank you, my man. Can't wait to do it again.
Looking forward.
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