185: From Shoebox to Success: Sammy Taggett's Inspirational Story of Visionary Leadership

To be a transcendent leader has always been a mystery to me. I remember when you first told me about your show, I thought about who's a transcendent leader and I think of the people like Richard Branson, Naveen Jain and Vishen. Some of these folks, I didn't understand where they get the power to push through so many things, employ so many people, and then execute so many different visions that they have. And I realize that they have a transcendent pull of a bigger vision that is guided by something way bigger than them.

Welcome to Transcendent Leadership. We bring together top leaders and experts to share their unfiltered truth about the journey to self actualization and the path to heart centered leadership. You'll hear raw lessons, learn ancient wisdom and practical steps to rise to your fullest potential. Now is the time to walk into this new paradigm of leadership. Let's transcend together.

Hello everyone and welcome back to Transcendent Leadership. Today's a very special day because we have a dear friend of mine, Sammy Taggett, here on the show today. Welcome, Sammy.

Thank you. What a place that we're in, right? What a perfect place to have our interview.

Oh, I couldn't think of a better place.

Wow.

Thank you so much for being here. Before we dive into so many things, I want to tell people a little bit about you and then I want you to tell them about you. I've met Sammy in San Diego and he is a dear friend of mine, but he's also an incredible artist, human being, podcast CEO and accidental CEO, which we'll get to in a moment of evolve podcasting. You hold so many different facets and hats of yourself and you also go by the name Shoebox Sammy. So I'd love for you to share a little bit about your backstory around around what that actually means and why you've adopted that name.

Well, thank you. It is funny when you hear back too, right? How many things you're doing, how many hats you're wearing, because you are similar, right? You wear a ton of hats. And then I accidentally fell into the CEO role as a dj. I was playing music for a lot of these incredible game changers around the world. Vision being one of them. JJ Virgin, Richard Branson, things of that nature. And what happened is I started listening to their podcast because all of them have podcasts. Had to be really upfront with them when they asked, like, how's our podcast? And I was like, yeah, your podcast is terrible. We should fix that. So that happened and then what that turned into was me becoming a CEO of a podcast production company, which was really cool. But prior to that, as a dj, what was really fun is I was always Sammy, just DJ Sammy. And that was fine for a while, but I. I'm adopted from the Philippines. And one of the things I always wanted to do was go back to the Philippines and kind of find my origin story and find out, you know, what orphanage I was from and just kind of the. The lay of my life. And so I went back seven years ago, and in this pilgrimage, I found out that I wasn't just adopted and I wasn't just kind of left at an orphanage. I was actually left in a shoebox in a dumpster. You know, it sounds really rough, but there's a lot more of that than we like to, you know, speak about, but it happens. And what's lucky is I was found by two police officers and brought to the orphanage. So I was saved. I got the golden ticket. And then later on, about a year and a half later, I was actually adopted by this incredible family in Colorado. So I got out of there. Fast forward to DJing for some of the most powerful people on the planet, and I realized that I have a bigger calling. You would call it transcendent in some ways. And I knew that I had something that I could do, something I wanted to give back. And so when I approached my friends and my colleagues about that, I said, I really want to go in and. And learn the art of educating kids better or getting kids an opportunity. I know there's teaching, there's mentorship, there's these ways, but I feel like there's even more ways to set kids free. So what I really wanted to do is just put these systems in place and instill these systems that would allow kids to. To free themselves, especially from my orphanage. And so they loved the idea. And then they called me Shoebox Moses because of Moses setting his people free. And the whole play on words happened. And all of a sudden, six, seven years later, people now call me Shoebox Moses as a performer, which I think is the most beautiful tribute to my mission. And I really have embraced that. That title. And it's just kind of fun because it keeps me grounded. And then we just had a little baby just five months ago, and it's incredible to see that now this legacy name for what I'm doing is going to be passed on to him, and then he'll know who I am because of what I'm trying to do. So it feels really good. And I. I love that we can have these conversations because it really helps me remember where I'm from. So thanks for asking.

Yeah, thank you for sharing that. I know that I got immediately emotional, even though I've heard this story now a few times. And I know our audience is, is really going to feel that too. And it really speaks to the testament of a transcendent leader. Going beyond limitations, going beyond self, and really seeing the totality and the full vision of like, what else is possible and like, where do I come from and how do I give back? And so I'm curious. You know, many leaders want to take their pain and put it into their purpose, right? That's like a fun thing to say, but how is that actually done? I'm curious. How did you actually take that pain that you went through and moved it into something that fueled fire within you to want to give back and, and now to be a father and to see that come full circle for you, in what ways has that really inspired you?

Wow, what a really good question. I think for me, how I moved that pain, it was out of necessity to keep up with what I was given the opportunity to do, which was perform and to kind of lean into new career paths. So I was always a dj, but once I started moving just past being a dj, I had a film company a while back. I had all these little things I was interested in. And with the advancement of technology right now, I was collapsing that 10,000 hour, you know, standard. I was becoming proficient enough to make a living as a film producer, as a dj, as a talent scout of all these things. And so I think from sheer drive that I had, I had all these things coming up and I didn't realize, like I was hitting the ceiling on being able to go past a six figure mark. I was hitting these ceilings on being able to manage people as city to ceiling on how to manage my relationships. And so the part that I pushed through all that, it wasn't even imposter syndrome. I was literally breaking my systems, I was breaking relationships, I was destroying infrastructure around me because I didn't cure the wound of the past. I didn't forgive myself for the past. I didn't forgive my biological mom's situation for the past. And so what I pushed through, I think, and how I use that fuel was through forgiveness. And I had to forgive myself to really light the fire on how to get through that. I learned some tools. A lot of it was meditation. A lot of it was just some of the stuff I learned at Mindvalley, which is where we're at right now, which was rapid transformational therapy with Marissa Piers. Some of these tools that I just didn't know existed. And so I used some of that to get through it. And it meant the world to me. To answer that question. It just, it opened up the world for me, and it meant changing the paradigm for everything I was doing. It was crazy.

Yeah. It seems like in some ways what I'm hearing from you is that you realize that you were given a gift, you were given a chance, and to really want to give that back because of the opportunity that you had a hundred percent. And you just, you started to describe this really beautiful recipe of meditation and these tools. Can you speak a little bit to faith? What part of that role has led in your life?

Yeah, you know, interesting enough, faith has come and gone for me in my life. A lot of times I find that at the bottom of situations or even the bottom of a bottle, or where we at in my space as a. As a performer. And I was a bartender for like 10 years, and that faith thing left a lot of times, but then I would find it at the rock bottom. Funny enough, you flip that paradigm. When I found ultimate success in certain spaces of my life, which I.

Big shows, I played at a venue in Colorado called Red Rocks a couple times, and that was, for me, a very pinnacle moment. At that point, I found faith again being like, wow, thank you for this opportunity. Instead of just being like, hey, help me out. I found myself being very thankful and full of gratitude for the opportunity I had. And I was noticing that it kept flipping back and forth. And so I wanted to do was adopt a practice of faith that would bring it there consistently. And so what I think is I found and what role faith has played in my life right now is that it's been very consistent, even though I haven't been. And so it's really shown me that it's this long marathon we're on right now while it's in a short blink, but for us, sometimes it's this marathon, but the peace, the faith. And I have a faith in God and I have a faith in Jesus that for me, that hasn't really gone anywhere. And so it's helped me become a much better father, a much better partner, and ultimately a better servant for the people around me so that I can be a better CEO and be the best version of myself. So faith to me right now in this chapter of life has become a very, very easy thing to step into because I've seen it from the bottom and the top. And so I think I've found like the consistency of it, which has been really fun.

Yeah. Like creating your own practice. Right. And it's not faith from a religious context. It's like openness to something greater. Would you say that creating your own sense of what that means to you really helped you anchor into it more?

Oh yeah, absolutely. And. And just seeing how life has shaped what it is for me because it's different for everybody. Your relationship with your faith is always a totally unique piece of anyone's life. So. Yeah. And it's definitely morphed. And I'm sure it'll morph again, like probably.

Are you gonna evolve?

Totally. Yeah.

Well, let's speak to for a couple minutes too. With the different hats that you wear, how is it that you take the lessons that you've learned in becoming a leader and really amplifying your leadership now? How do you manage leadership in your home? How does that show up in your relationship? And now being a father, the biggest.

Thing it does is it allows me a lot of grace to totally fuck up. Cause I'm like, I'm not perfect. So it gives me the ability to just be honest and graceful with myself, knowing that I'm not gonna get it right. Like I didn't know a 5 month old shouldn't be eating chicken wings. Who knows that stuff? Right. So I am graceful with myself. And that is rooted in a beautiful faith. And then there's also that idea that even though myself and my partner's name is Ray, we go the wrong way all the time with each other, but yet we have so much grace for each other. And that also comes from that deep rooted part of our faith journey. And it's not just in God, but it's just our faith in each other, faith in life.

Right. Like how this is happening right now, this beautiful orchestration of just everything that's happening. It's like life is happening through you in some ways. So it's faith that everything's working out. It doesn't need to be. Faith in, you know, God, although that would be a beautiful practice, doesn't need to be that. But it sounds like you're finding your flow in all of that.

Totally. And it's helping me just like to have these conversations with other people. I think what's nice about your show, what I love about transcendent leadership, there is a certain way to practice being a leader. And to be a transcendent leader has always been a mystery to me. I remember when you first told me about your Show I thought about who's a transcendent leader, and I think of the people like Richard Branson, Naveen Jain and Vishen. Some of these folks, I didn't understand where they get the power to push through so many things, employ so many people, and then execute so many different visions that they have. And I realize that they have a transcendent pull of a bigger vision that is guided by something way bigger than them.

Yeah. And in some ways, too, it's the unsexy things that people don't talk about in leadership. Like forgiveness, like you were just saying, like the ability to fuck up, like make mistakes and all that being really important in that. And so I'm curious for you, when it comes to leadership, what do you think is one of the qualities that people don't talk about enough?

Oh, with a leader, I think the quality that they don't talk about enough with leaders is their compassion. The idea that they have to be compassionate first with themselves, like give themselves a little.

Such a prerequisite.

Right, Prerequisite. I think most of the people I know, especially the people in my peer group, they are very compassionate on themselves now if they've gone to the next level and then they're very typically very good with the group around them because they know it's not on them. It's a team that builds this stuff.

How do you define compassion? Like, how does that show up for you?

That's always shown up for me. With humor and laughter. Like fun.

You're so good at that.

Yeah. My team, they. I think they love, hate me a lot of times because they're like, what are you doing? I'm like, it's so fun to do this. And they're like, stop doing that. Don't push those buttons. I think of how compassionate you are with a child. Right. Like, when they do these things, you're like, oh. And I think of myself as a constant child. Like, what's this button do? What does this do? What's this do?

Actually reminds me, somebody asked me here at a fest, how do you navigate difficult conversations with people when they're projecting something onto you? And that's one of the practices that I do, is I look at people as a child and it really drops me immediately into my heart. And I like, I'm really able to meet them where they're at in that moment with the defenses, the survival strategies, whatever it is. So I think compassion is a really underrated aspect of being a really good leader, especially this new paradigm of leadership, transcendent leadership. Really coming from that beautiful heart space.

I love the question. Thanks for asking that too because it is an interesting one to think about. Like what does make a good transcendent leader? And compassion is definitely a huge part of it.

What's really alive for your life and leadership? If you're willing to be a little bit vulnerable, where's an area that you're kind of coming up against friction or being challenged?

I love how you say alive like so where am I jacking things up?

Where are you messing things up right now?

I think there is a level of leadership that visionaries have that we have to understand that there is a formula to having things work inside of a team. And sometimes when we have a vision and we want to do something that's astronomical. Like my vision is to be the producer of a thousand of the most game changing conversations on the planet while at the same time providing jobs for kids out of the orphanage and at the same time reinventing what it means to have a binge worthy show so that you have the ability to speak to millions of people, make a whole business with your podcast or and the show should turn into a show, not just a podcast. And then employ some of the least of these and give kids an opportunity to have a career inside the creative space that our editors are teaching them. So a lot of times our team's like, why don't you just focus on the first 50 people? And so you have to adhere to the speed of what your team can do and you gotta make sure that you communicate with them as beautifully as possible. And so my edges is learning to communicate with my team, like my vision and then find where we are stuck and what we can do to come up together. Because all ships rise with the tide. And if the captain's like, yo, I'm surfing this big old tsunami. And they're like, we're in a dinghy right now. What are you doing? Then it's not going to work. So I think that's my biggest hang up right now is just like making sure everything is handled by the team and me getting out of the way.

Really staying in your zone of genius, right? And really holding that in some ways. I think a lot of leaders, especially really visionary ones, they see where they're going. And so sometimes people don't see it fully yet. And so enrolling the people to come with you as well as holding that vision, but being exactly where you're at and just letting you walk and like take those steps in that process is going to be really helpful and I know myself as well. People ask me, like, what is your weakness? And in some ways, it's. I hold people to their potential and I see the vision. And so sometimes when we're not there yet, as a leader or even with myself, there's like this underlying judgment or these expectations not being met because the vision is so big and daunting. It's like, because you're not there, you know you want to be there. And when you feel it and you hold it, it becomes challenging.

I think, as visionaries and a lot of people have this, that you see the vision of what you can be, and then you see where you're at, and you don't know the steps inside the gap. It just gets so frustrating because you're like, oh, they did that. How come we can't do that? We have the same tech, we have the same time in the day, we have the same amount of people. So, yeah, that's some of the. Some of the frustration that I run into.

And in some ways, that's where the faith comes in, right? The faith in the process, the faith in the journey and yourself, that you're exactly where you need to be and everything's happening perfectly. So, you know, as we begin to wrap up here, I'd love to know from you, what are you learning in this season? So that's what's alive for you? Like, what are maybe some practical things that you're learning about leadership that you can offer to the audience?

The biggest thing I'm learning right now in leadership is that you don't have to take as much time as it used to be. There is so much technology and there's so many things that you can do right now to circumnavigate the time and bend it. There's so many places you can learn things. Like, we just had a big discussion on AI. Like, I talk about it all the time. It has the ability to turn not only yourself into, like, Neo from the Matrix in a way, but there's so many ways that you can get and acquiesce knowledge faster than ever possible. And then with the ability to access the information and the brilliance of so many world changers on the planet, especially through podcasts, you can really bend the amount of time it takes to be a leader that is better than you were last week, every week, you should be improving. And that can be an exponential improvement if you can crack that code. Right? Because I see you, I see how fast you've grown as a leader in the last few months. Right? And that's all stuff that we used to have to read our books on. We used to have to listen to a lecture or seek that stuff out. Now you can walk with your phone and listen to Vishen. You can listen to Naveen. You can. You can almost reach out and touch those people. Like you feel like you know them. I mean, that's what's incredible. And that's, to me, is what I think is the best thing about what I'm stepping into now. We can bend that time.

Basically. Adopt AI is that you're saying adopt AI. Well, one of the last questions I want to ask you is, in your own words, how would you define transcendent leadership?

I think that would be a combination of faith, compassion, and fun. And embodying those three aspects into everyday walks of your leadership. Faith, compassion, and fun, I think would be my three things. I can't believe I made that that succinct, but that's what's coming through.

I love that. And I love the emphasis on walking. There's seasons you might be running and there's seasons you might be jogging. There's some seasons you're walking or crawling, but as long as you're moving, that's what's important.

Yeah, totally.

Beautiful. Cher, thank you so much for being here. Sammy, it's been a pleasure to have this conversation. Waiting to have it. So it's good that it got to happen in person. And I appreciate you, brother.

Perfect. Thanks for having me.