David Holloway | Charlie’s Interview - SFO Oct 2024 - Also attending in Dec 2024

Why don't we get started when we find out a little bit about what you did in the professional athlete space, and that way we can give a little bit of background about where you came from and what you did up until today?

Yeah, so in a nutshell, I got very lucky to be honest and to grow up in a world where I'm a third-generation pro athlete and a sixth-generation college graduate. So champions on both the academic side and the athletic side. My dad played for the New England Patriots, and my grandfather on my mother's side played for the Boston Bruins—the Big Bad Bruins. My dad played against the 85 Bears. So I was around all those sports champions. Growing up, I was born on game day. In fact, they have the game ball. It's still here. The old school ones with the paint on the front. But I was given that when I was born. I was born on game day; Patriots beat the same. So I figure I'm good luck.

Yeah. And, you know, that's the athletic side. On the academic side, there are three college presidents in my family. Currently, my uncle is the president of Rutgers. I'm a huge Scarlet Knights fan now—go RU! But I was born in that world with so many champions that helped shape me and made a huge impact, not just on their teams but far beyond that. The lessons they gave me—gifts—they always said, “It’s not fully complete unless it’s shared.” So part of my new mission now is to share that.

But my journey—when I first started off—you'd think, with this great family legacy, that I'd be a shoo-in. In fact, I got rejected by over 850 Division 1 colleges and over 10,000 scouts. A lot of rejection, you know? So I had to find my own way. Even with all the greats I grew up around—Bo Jackson and Bobby Orr and all these superstars who were around me my whole life—it was now my turn. Everybody was saying, “Who are you? You're not big enough. You're not fast enough. You're too small. You don't have your grandfather’s toughness. You don't have what it takes in sports. Maybe you should do the academic side.” So many champions there too, which wouldn't have been a bad move, but you know, something in me said, “I still want to do this.”

So I decided to walk on at the University of Maryland. I didn’t get a scholarship. It took me about a year and a half. When I first got there, I was getting laughed at because I was a triple-digit weight. I was one of the 336s. Adam Podlish and Alan Grantham were the other two 336s there. I couldn’t eat with the team at the new dining hall facility. You can’t if you’re a walk-on. So I had to run to get my food. There are so many other stories I could tell you. But I came in as a linebacker with a vision and a dream. Anyway, I weighed about 187 pounds—way too small to be a linebacker. You’ve got to be around 250, or you’re just going to get tossed around—which I did. So I got laughed at in the beginning.

Fast forward three years, following my vision and a lot of hard work. And in the middle of that, more getting laughed at, walked by like I wasn’t even there, I became one of the best in the country. And that didn’t happen by accident. That was by clear and proper design. And that’s part of what I share now as a motivational speaker. I have a book coming out soon, so I’m in that expert space, sharing my insights, wisdom, and some of the tactics I used to go from someone who was getting laughed at, couldn’t eat, all of the above, as a supreme underdog—to now, people are asking me how I did it. Later, I found out people were dropping out of school to come to the University of Maryland to try to duplicate what I had done. We were one of the best defenses in the country. We beat Florida State for the first time in school history. In the early 2000s, Maryland was doing pretty well—ACC championship, Orange Bowl, all these things.

But all that happened, and there’s a blueprint. And they always say greatness leaves clues. And a lot of those crumbs—not only did I follow from all the greats that came before me, but I left some there as well. Now, so many other walk-ons were able to get an opportunity. People who dropped out of their colleges to come to Maryland were now able to do it. I’m used to being behind the scenes; nobody knew who I was. And now, I’m out in front of thousands of cameras, people's stories, Washington Post—all these things. They’re asking me to share my story, my journey. It’s inspiring, all these great things. I was one of the guys in the locker room who was pretty quiet, didn’t say much. I said, “Hey, I’m going to show you, and I’m going to lead by action.” Not too many words in there.

But as I grew and matured as a leader, listening to people around me saying, “You’ve got to do it over and over again,” I thought, “Let me take this seriously. Let me study this. Let me figure out what other speakers I could learn from.” I went to boot camps and seminars—two or three days with some of the greatest speakers in the world who did TED Talks with millions of views—and learned the art of being on stage. I learned to use my body language, voice, tonality—all these different things that not only helped in my speaking career but in my overall life, helping me skill up. That added a lot of things.

So that’s where I’m at now. That’s the funnel into who I am, where I come from, what I stand for, and what value I want to bring to you, the listener, and everyone I come into contact with.

No, I think that’s a great story. A lot of times, I feel like a lot of stories go like this: "Alright, this is the one thing I had—I only had sports, I had nothing else to fall back on. I didn’t have any family, or you had some family that you could fall back on, or let's say you had the academic side that perhaps you could fall back on." But for you, what was it that made you able to stay on the path? I mean, I know we talk about visualization practices and mental mindsets, but as much as you were a walk-on, many people in your same shoes could have just walked right off. They could have decided, “You know what? I don’t get to eat with the team. I just can’t do this. I’m not going to be able to put on the pounds or stay in the mental mindset that you need to stay on the field.” So what was it that you did to stick to it? What made you not choose the easier route?

So much easier, I mean, at 18 years old, you're getting tossed around on the field, not getting the practice. I was on the second team, so I couldn’t even get into practice some days. I don’t know if you’ve ever been in Arizona or Miami, but the hottest I’ve ever been is sitting in full equipment, just watching practice for like an hour and a half. That’s back-to-back doubles. So it was miserable. Everybody asks, “Did you think about quitting? Taking the easy route?” Hell yeah, I did. I thought about it the second day. I looked up, didn’t get into practice, then had to watch the film of practice. I didn’t see anything I did except stand there and bake. I was like, “Man, this sucks. Why am I here?”

And I found, you know, I reverse-engineered it. When people asked me why and how, I was like, “You know, let me really give people some takeaways they can use in whatever situation they’re in.” I go all the way back to the foundation. I used to stay up late at night, like most kids, and just dream. I’d block time and take my journal. I’d just write down exactly what I wanted to do. I didn’t get the scholarships everyone else got, but I was lucky enough to choose where I wanted to try this. I got really detailed. When I visited the University of Maryland, I had a feeling. I was like, “This is the place I’m going to be.”

That foundational piece—going back with pen and pad, writing down exactly where you want to go. Yes, that’s part of a vision. But I do trainings on this. I do half- and full-day trainings. There were actually five steps to properly crafting a vision. I share the five steps that I used. The first one I just shared with you—simple: take a pen and pad. One thing I’ve learned as I’ve matured as a speaker, trainer, and executive coach: you’ve got to distill a lot of wisdom and give it to people in easy, actionable steps. So I took my five steps and said, “If you follow these five, you’ll have a properly crafted vision that will pull you forward in life, to get you past all those obstacles.”

If I didn’t have a promised-land vision of something greater that got me excited, why was I doing all this stuff? Why was I getting up and working out early before the team? Why keep getting laughed at every day when you’re in college? Is this supposed to be your golden days, your best four years? One of the best experiences of people's lives? For me, it was misery, man. People said that stuff, but I kept working on my vision. And that’s what got me through. You don’t have to be a genius to know that, when you have a strong enough vision, it pulls you forward. The obstacles, in the beginning, felt like mountains. But the more I worked on my vision, the more I visualized it, the smaller those obstacles became. And I was able to step over them.

So, yeah, that's the vision part. When I first walked up to those obstacles, I’d say, “I'm going to make this happen. Not only am I going to play here, but I’m going to be one of the greatest to ever do it.” And I wouldn’t even blink.

That's the power of having a strong vision. It's the foundation that holds everything together. When the storms of life come, when people come with their doubts and their negativity, a strong vision will keep you moving. You know, I knew from the beginning: “I’m going to the top. If you want to compete against me, you’d better have a sharper vision, because I’m not stopping.”

How do you block out other people's opinions—coaches, players, sports newscasters—all those different perspectives that can affect your vision of where you want to go?

I think the root of that is how you fit into someone else’s vision of you. If you read *The Top Five

'Cause, like I said in the beginning, I was getting laughed at a lot. And when you're an athlete, it sucks to get laughed at. I was getting laughed at almost daily. I was getting embarrassed all the time. It was not fun. This was in... You know, this is pretty much rock bottom when you're not—when you're a bench warmer in practice. That's hard to get lower than that. So here I was, and all this criticism and negativity, and people walking right by me and using me as a... You know, a tackling dummy or all these other ways that, you know, this guy doesn't even really matter. Let's give him a triple digit, because who cares?

In those moments, then I share this with people and you get hate. When you get other people's opinions, you get things that, you know, sting sometimes. A lot of people tell you to forget about it or ignore the haters, which doesn't work. It didn't work for me. You can't ignore some of those things. You know, we're all human. We have emotions. And all the personal development, reading, everything I do, I'm still a human at the end of the day. There are still things that are going to bother me. Now, the time that I get over it is way shorter now, and it's done much more gracefully. But what I'll tell you is this, and here's what you do: It's a simple technique called "throw in the bag," and I invite you to try this.

If there's a moment where you just feel the hate coming or you feel someone diss you, you feel off your game, whether that's personal life, work life, it doesn't matter—something's really bothering you, I invite you to take that moment. Remember it. What people... almost take a screenshot, a snapshot of that moment. But I want you to take that and visualize taking it, putting it in a bag, tying it shut. And you're gonna move that to the side. So you're almost, you're feeling it for a moment, and then we're gonna say, "Okay, this is happening. All these feelings, I'm gonna take that, store it for later."

So, because if you don't, you're going to waste energy that you need to get to where you want to go. You're going to waste energy the day. There's so many energy vampires out there that this is something that you have to do for your own sanity and protection. Sometimes I know everybody listening can relate to that. So, what I did in those moments was okay, take that moment, feelings I feel, I'm not going to ignore the tension or the anger that's building up. I'm gonna save that for when I need it.

And when I would go work out, when I didn't feel like doing it that day, whenever I needed that little energy boost or even a rocket boost, if I was doing well, I said, "Man, I'm going to that bag and opening it. I'm remembering all the feelings, everything that was said, what the person was wearing, the look on their... and refuel that energy." And that's going to give me that fuel, that dark energy to keep going, even when I don't feel like it. Even when everybody else is quitting. Even when it's hard.

Because it's going to get hard. It's going to get tough. But when you can use your energy, your power, when you need it, man, that gives you such a competitive advantage and someone else that is letting everybody else shoot them with their arrows, the hate, and now they're leaking. And you know, it's your energy, it's your power, it's your motivation, your positive feelings about who you are in the day. They're letting everybody else shoot them and let it, you know, drip out. I'm telling you to take those arrows, put them in a bag, save it for when you need it. And man, that'll give you energy at any point.

Now, do those... does that bag start having less and less effect, and you have to fill it with new ones? Or how do you use that bag? With, you know, the way social media is and everybody else having their opinion today, that bag can fill up real quick.

That is true. That's true. And the important thing is, you know, yes, this is a blueprint outline of how I used it. I tell people to take that and add to it, add your pieces to it. Don't be like... you see so many people every day, "Oh, this is the new style. Let me do this." Or "This is what this group does and I want to be part of that, so let me dress like this, get these shoes, get this water bottle," all these things that people are just copying each other over and over again, which is fine, I get that. But always add a little flavor of your own to that.

So, you know, you're more of an individual, you're a little more free thinker. You're a little bit, you know, you're not following all the time, that you're always adding in some little bit of your leadership into that. So that technique, throwing the bag, use that as a foundation, but add little pieces to it. What do you want to put in there? How much, you know, is there a point where it's getting too much and you gotta let it out? What are some of the healthy ways you like doing it?

I've always advised to do it, you know, working out in some kind of way, because how can you skill up? No matter what profession you're in, you work on your health and energy, you know, protecting your energy. It doesn't matter what age you are, you know. But again, we're only given one body. We get one shot. It's up to us to protect it, to preserve it, to continue as you get older, to take care of it, to do the rehabs, to do the strengthening so you have more energy. So you can enjoy more of this thing we call life.

No, I like it. I like it. Well, let's do this. What's like, what's a one million dollar lesson or what's like the most costly financial mistake that you've personally made? And you can just give a general one, or if you want to give a very practical specific example, but for any professional athletes that are out there, like, what's a million dollar lesson that you learned, perhaps the hard way, or financial mistake that you're like, "Man, I wish I didn't make this, but don't make the same mistake?"

• Yeah, they all come down to the same thing. And that's just, I reached a point in life or my profession or financially where... I'll give you two things. One is when I got to a point where I feel like I made it, that was a danger zone for me. That was a million dollar mistake in those areas because now I have no vision of, you know, what I want to head to next.

And it's nice, yeah, when you reach the top of a mountain to celebrate, to eat the food, enjoy the riches that are up there, you don't want to be there too long. The first time I got there, I was there for way too long. And I started to decline. Those are moments in life that I can't get back. The moments where I wasn't on my A game, where I wasn't taking care of myself the best way, or I wasn't doing the research, I wasn't learning, I wasn't serving people around me the best way I could, I wasn't paying attention to a lot of the foundational pieces that got me to that point.

And what I always tell people is when you're out for self-mastery, when you're about to make it to that next vision or when you're there, you immediately start crafting a vision for another future. And if you don't, you're gonna make a lot of mistakes. You're gonna live in a place where I call the land of mediocrity. I give this analogy. I said, you're on the field of life, the court, the ice, your office, whatever it is professionally, whether you want to relate it to your family life, you're on the field of life, that field. And it's your job to go out there, some of the best of you are, become the best, share the best, give the best, and live and lead the best quality of life you can. That includes having great foundations.

The life's not knocking you, pinballing you all over the place. So when you're there, you have a vision, you're on top of your A game, you're kicking ass, taking names, you're making wise decisions, you're connecting with the right people. You're not ignoring your health. You're not ignoring your positive relationships because that can easily get burned when you're heading up those mountains of greatness or success or excellence. You're on the field of life and you're playing full out.

And you don't have a vision of greatness. Life hands you a ticket to go sit in the stands and watch. And in those stands, it's very, very comfortable. And it's very deceiving. Oh, you're here. You made it. Congratulations. Let me pull up a chair. What do you want to eat? What do you want for, you know, the five-course meals? What do you want to drink with that? Can I get you a pillow? You know, are your nails done? You know, all the things that, you know, are in your comfort zone.

And man, you don't have a vision for a bigger future. You made it, and now you're just sitting kind of coasting. Somewhere deep inside, man, you feel like something's off. And you feel like, man, I just, I don't have that juicier energy in the morning. I'm doing all these great things. Everybody thinks, you know, Anyway, gave you the foundational piece. When I was there in Arizona, I had made it. And I was like, is this it? And one of my mentors got lucky enough to be around, and it brought me back into reading again, learning again.

And it's something that I would leave with everybody: I said, you should always have a learn list. You should be reading, you should be studying, you should be around other people that are going to challenge you in some kind of way to help get you better.

One of the biggest regrets I had was throughout college and most of my NFL career, I had stopped reading on things that I was interested in. I was so focused on who I was and my identity as a football player, which one of my good friends, Sean Stevenson, who was a trained therapist and a speaker, from whom I learned the art of speaking and storytelling, shared with me that, "Hey, you're not an athlete. That's not your identity. You are much more than that. That's just part of what you do."

And I was like, "Man, it was a breakthrough for me." It sounds very simple, but a lot of times the breakthroughs happen when you become aware of something that you were never even aware of before. I wasn’t aware of it—that I had lost touch, lost connection, all these things, these hobbies that I enjoyed.

So, through my mentor's advice of reading and continuing to learn, I started learning a second language. I started picking up hobbies that I always wanted to do—playing the piano, doing all these different things that allowed me to have a more enriched life that I had stopped doing.

So, there's one piece of advice I want to give everybody out there: continue to build your learn lists, whether that's for your profession or one of your hobbies. Never stop learning. You know, my mentor put me on all these readings and seminars and stuff. He always still said, named Joe Polish, who founded the Genius Network out in Arizona. Yeah, great guy. He says, "Education is never out for the pros."

And even though you graduate, it doesn't matter. Education is never out. I am never going to stop learning, finding new ways to enjoy life, finding new ways to sharpen my intellect, because that's what I was taught. And when you do that and you skill up, you know, like they say, the analogy of the water—the tide comes in that lifts all boats. That's part of what happens: it lifts you and all the people that are connected to you.

Again, I just got very, very lucky to be put in the position where I was around these foundationally excellent people who thought bigger than just their profession, who wanted to continue to have a bigger impact no matter what their achievements were in the past. They wanted to make their future even better. So, I was lucky to be around all these great people, and again, I don’t take that for granted. I understand that I was lucky to be put in this position where I was able to be around amazing people.

Yeah, part of who I am is, you know, I'm always curious to learn, so I was always drawn to that. But one of the things they taught me, like I said in the beginning, was that the great gifts are not fully complete unless they're shared. What good does it do if you have all this knowledge and wisdom and expertise if you're not sharing it with those who are coming up behind you and those around you?

And the last thing I'll say on that is this: we all have a sports analogy here in our arenas—our family, friends, and relationships. We have arenas, and at the top, there’s banners flying high, of people you wouldn’t be here if it weren’t for them. A lot of giants came before us that we stand on the shoulders of. The spotlights are there in our arenas alike. And man, when you're up there, you want to shine as bright as you can.

One of the ways to do that is to share your best and highest practices. And that’s what led me into what I do now as a trainer, motivational speaker, and executive coach—to share these great lessons that allowed me and so many other people in my family to rise to that 1% and then to get to the top of the 1% of the 1%.

Education is a way out of so many things. So, continuing to learn, to continue to have a "to learn" list. You know, at the beginning of the year, everybody's talking about New Year's resolutions. What’s on your “what to learn” list for the month, for the year, for the quarter, whatever it is, that's the key.

• I love it.

Well, David, thank you so much for being a part of the show today. I can’t wait till I actually meet you in person, have you up on stage at our event, and I just appreciate the time that you took for myself and then also for our audience.

Absolutely. I enjoy what I do now. I'm never going to retire from it. I'm going to continue to learn. I practice what I preach, and I can't wait to be on stage and help people in different ways—remind them of their personal power, give them key takeaways so they can enjoy their journey even more, so they can get to the top of that mountain, whatever they’re climbing, even faster. It was great to be here with you today; hope it served you guys.

• Oh, it did for sure. Thank you so much.