Leap Academy with Ilana Golan - Dre Baldwin: Mastering the Pivot from Professional Sports to Business

Episode Date: May 23, 2024

Dre Baldwin got a late start in basketball, however, he marketed himself tirelessly to stand out from the competition. His strategies worked and he landed an agent. Although initially unintentional, he built a personal brand online as he played professionally. So as basketball prospects waned, he was able to transition into public speaking and entrepreneurship. In this episode, Dre shares his journey from an obscure basketball player to a successful entrepreneur, highlighting key tips and lessons for professionals considering entrepreneurship. Dre Baldwin is a speaker, author, entrepreneur, and business coach with a background as a professional basketball player. He works with businesses and entrepreneurs on branding and marketing their businesses through his company, WOYG Enterprises. In this episode, Ilana and Dre will discuss: - His basketball career - The marketing machine he created to sell himself - Monetizing his knowledge with digital products - The differences between working in sports and business - Why discipline and determination are crucial for success - How building relationships can lead to opportunities - The importance of continuous learning and self-improvement  - Personal development for professional growth - Mindset, discipline, and taking initiative for success in any field.  - Self-accountability for personal and professional growth - And other topics…   Dre Baldwin is a former professional basketball player turned author, entrepreneur, and business coach. He played basketball internationally for nine years after getting a Business Marketing & Management degree from Penn State Altoona. Dre started sharing his basketball workouts and motivational messages on YouTube in 2006, growing to over 100,000 subscribers and 35 million views. He consistently posts daily videos, leading to the development of his "DreAllDay" and "Work On Your Game" brands. Through his company, WOYG Enterprises, Dre assists businesses and entrepreneurs with online branding and marketing.  Connect with Dre: Dre’s Website: https://www.dreallday.com/  Dre’s LinkedIn: https://www.linkedin.com/in/dreallday/   Resources Mentioned: Dre’s YouTube: https://www.youtube.com/channel/UCwHgkC8tsH6r0hQjCw_raYw  Dre’s Book, The Third Day: https://www.thirddaybook.com/the-new-book-for-people-who-want-to-be-more-consistent-disciplined-but-can-t-get-started  Rich Dad Poor Dad: What the Rich Teach Their Kids About Money That the Poor and Middle Class Do Not! by Robert T. Kiyosaki: https://www.amazon.com/Rich-Dad-Poor-Teach-Middle/dp/1612680194  The 4-Hour Work Week: Escape the 9-5, Live Anywhere and Join the New Rich by Timothy Ferriss: https://www.amazon.com/4-Hour-Work-Week-Escape-Anywhere/dp/0091929113  Think and Grow Rich by Napoleon Hill:  https://www.amazon.com/4-Hour-Work-Week-Escape-Anywhere/dp/0091929113  Start with Why: How Great Leaders Inspire Everyone to Take Action by Simon Sinek: https://www.amazon.com/Start-Why-Leaders-Inspire-Everyone/dp/1591846447 

Dre Baldwin, 25 books, four TEDx talks, masterclasses with, I don't know, 7 million listeners, years of professional basketball. Some people will say he's just talented. I can't do that. What would you say, Dre? And thank you for being on the show. Well, thank you for having me, Ilana. I think I have a little bit of talent, but it's much more the discipline is the most important thing,

especially when you step into the professional space, because at the professional level, everybody has some amount of talent. We all have resources, information, and experience. So what separates one person from the next is really, I think the most important thing is your willingness and ability to continue showing up. That's the most important aspect of discipline, especially for me. Oh, and I love the word showing up and you have a whole thing around working on your game. But if you would have asked the kid, Dre, would he know that this could be your life? Absolutely not. Because the life that I have now

is really based around, it really started with the internet and the internet being what it is. And when I was a kid, I think the internet might have existed, but nothing like what we have here today. So there were no podcasts, there was no self publishing, there was no social media, there were no influencers, there was no digital products, none of this stuff existed. And a lot of what I do now business wise is based on those things. The only thing I did that wasn't really based on that was playing basketball. And that I probably wouldn't have guessed either. I thought I was gonna be a baseball player or football player. Basketball was kind of like the last resort when it came to sports. So tell us more about this, Dre, because I think you already showed a ton of determination, even as a kid. Can you share a little bit of baseball, a little bit of football. Never got serious or was

that good at any other sport. Finally got into basketball around age 14, which is pretty late if you're one to play college basketball, let alone pro. So I only played one year in high school and didn't really play that year. Walked on to play college ball at the third tier of college sports, what is called Division III. Most pro athletes are not coming out of Division III. Division I is the people you see on TV. It's usually those guys. And got out of college and wanted to keep playing pro, but nobody was asking me to play. So I had to market and sell my way into the pros. That's how I got in. And by using those marketing and sales skills, I knew that would separate me from other athletes because most athletes didn't want to do all that. They just want to play and just play.

I knew I had to do something extra because it was too many of us and not enough jobs. So being an athlete is different than being an entrepreneur in that there's a finite number of positions. Anyone can be an entrepreneur technically. Not everybody can play on a team sport professionally because there is a finite number of spots. So I knew I had to sell myself to get in, which I was able to do. I started what became a nearly 10-year career and at the same time started building my name on the internet through all that other stuff, which I'm sure we'll get into. So that's really how people came to know me was the internet, not actually pro ball. So it's ironic that you do all that work to become a pro athlete, but then nobody knows you

from being a pro athlete. They know you because you were on YouTube. It's just funny that it worked out that way, but it doesn't mean that being a pro athlete didn't matter. That was still a great accomplishment for me. And I think one of the things that I remember listening to you, Dre, is you talk about despite all of it and wanting to do basketball, but you still found yourself sometimes sitting on the bench and you still didn't quit. You still sat on that bench and continued marketing yourself to get into higher, higher places. What causes a 14 or 17 year old or whatever it is that your age at that point to not give up? That is something that clearly was your nature. Yes, it was. You're very insightful to pick that up. So absolutely, it was part of my nature to just continue to show up and keep trying at

something. A few things that go into that. So number one is, yeah, some of it was innate in that I was just going to keep trying and working on it and see if I can make it. Another thing was I had tried every other sport that I saw as available to me. So it's not like I tried everything. I never tried swimming. I never tried hockey.

I never tried soccer. I tried a little baseball, a little football. I think I could have been a good tennis player in Atlanta, but I never really played. Nobody in my neighborhood played tennis. We had a beautiful tennis court right next to the basketball court, but everybody's on the basketball court and nobody played tennis. I think I could have been good at tennis, but never played golf. So basketball was looked at as the last option I had if I was going to make it in sports. I could have made it in something outside of sports maybe, but basketball was looked at as the last option I had if I was going to make it in sports. I could have made it in something outside of sports, maybe. But basketball was the last option. So I didn't see a plan B when it came to sports if it wasn't going to be basketball.

Another thing is I had to credit my parents. I grew up with both parents at home and they went to work every day. And they didn't have fun jobs like what we do. They had jobs that they did what they had to do, but they did it. They showed up every day and they never complained about it. They also never bragged about it. They just went to work every day. When I got on the basketball court, I took what I saw modeled to me at home and I applied it to the basketball court. I just continued to show up because, again, sports was maybe my last chance. Also, just being a competitive person. I wasn't competing

against other people, per se, in the big picture. I was competing against the situation because the situation was saying, all right, this is not going to work. And I was competing back and saying, well, I am going to make it work. So it was just a continuing to show up. And as I accumulated little small incremental wins, it was just building up in my mind more confidence that I can make it happen. But even all the way up through the college years, it's not like most people from the outside looking in would have looked at me and said, OK, I see what you're doing, Dre. You did it. You made it.

No, you've kind of proved it. It wasn't until I became a pro when I signed my first contract, which was at the age of 23. That's when people could look at it and say, OK, I see what you're doing now. But all the way up through then, again, high school, I only played one year and didn't play. And in college, I was playing, but I was playing at a division three school, which doesn't produce pro players. So even our classmates will look at us like, all right, it's cool. You're on a basketball team, but where are you going after this? You're just on a basketball team here. This is nothing.

It doesn't mean anything. So it's not like anybody was looking at me like, okay, you're doing something because you made this level. It wasn't until I got to the pro level that then it was like, okay, now people are starting to say and see, okay, now you've done something. And that's incredible, Dre. And I think, first of all, you decided to show up every day. You created your own luck. You didn't wait for luck to come your way. I mean, obviously, we all need luck in life,

but in general, you create your own luck. And I think for some people, it always looks like that overnight success. Oh my God, Dre, he's just lucky and talented and he gets it all easy. But you really created this marketing machine around you and you pushed yourself in and you basically got yourself out of what John Maxwell calls a people pile in and you basically got yourself out of what John Maxwell calls a people pile, right? You got yourself out of that, right? Like the big people pile and to be noticeable, right? And that's incredible.

So talk to us a little bit about some of these marketing. Again, you've done marketing campaigns for the biggest companies in the world. We'll talk about it. But how did you even get started? Because it's a really beautiful story. How did you get out of that people's pile and try to get more marketing to be noticeable? So I got to go back in the story. So I started playing pro ball in 2005 at the age of 23. A couple of years before that, I responded to this bulletin board posting on my college campus that said, do you want to make some extra money in the summertime? Now, just to help people understand

why I even responded to that, I was a college student and I was playing sports. I don't know how much you follow sports, Ilana, but you know, nowadays in college sports, athletes can make money. They have this name, image, and likeness thing, so you can make money off your name. But back then, it was actually against the rules to make money off your name, image, and likeness, so it was literally flipped. So back then, if you made make money off your name, image, and likeness. So it was literally flipped. So back then, if you made money off of your name, image, or likeness, you were actually committing a violation and you could lose your eligibility to even play. A lot of people don't know that.

Yeah, so that was how it was. So if you're a college athlete, you basically had two jobs. You were playing a sport and you had to be a full-time student to be eligible to play. So you literally were broke. Most college athletes were broke. We had no money. So I'm looking to make some money in the summertime. Now, in the. So you literally were broke. Most college athletes were broke. We had no money. So I'm looking to make some money in the summertime. Now in the summertime, you can make money. You had to do real work, not just because of who you are. So I responded to it. Turns out this guy was some random guy. He's doing network marketing. Now I did not stay in the

network marketing industry, but I went to a couple of meetings and there were two things that happened at those meetings. Number one is the man on the stage was talking about money and money generating in ways that I had never been taught. The only thing I knew about making money at that point was go to school, get a degree, get a job, get your check every two weeks. I didn't know anything else about making money. And what this guy was talking about were concepts that made perfect sense, but no one had ever explained to me. And mind you, I'm like 21 years of age. No one had ever explained these things to me. And I also have a four-year business degree. And the classes I was taking on my college campus, nobody was talking about this stuff. I'm like, wait, why is nobody talking about this? Because

it made perfect sense what he was saying. Like, hey, if you want to make money, don't just work more hours. Figure out how you can leverage other people's efforts and sell other people's stuff and plug into a network and plug into a system. I said, why is nobody talking about this? That's number one. Number two, the guy said, because anyone who's been to a network marketing meeting, you know that half the people in the room are already in the business and half the people are prospects. I was a prospect. And he would talk to the people in the business. He said, make sure when you leave the room, there's some books out there. Make sure you buy some of those books, because if you're going to build a business, you must also build yourself. And the business cannot grow any more than you grow.

And I said, that makes perfect sense as well. No one had ever said that to me. And he was explaining this concept called personal development, which I had never heard before. I'd never heard that phrase before. I'd always been reading books, but I didn't know there was a genre just for making yourself a more valuable person. So that was the second thing. And in that second piece, I went out and looked at the books, which I could not afford because, again, I was a broke college student. But I remember a few of the books and I decided I would go get them when I got the opportunity.

So at the time, I went on eBay. And this was before Amazon was a place to buy books. And I bought a couple of pirated copies of these books. And don't tell anybody I'm telling you this. So I bought a couple of pirated copies. I bought Think and Grow Rich by Napoleon Hill. And that book really helped me understand that there's a way that you can consciously change the programming book I bought was Rich Dad, Poor Dad by Robert Kiyosaki. That book is really what set me on the path of entrepreneurship. And it got me thinking, okay, now this guy is explaining these principles even deeper for me to understand. I said, when I get done playing basketball, because that was my goal, mind you, at this time, I'm a division three college player. There's no guarantee I'm going to play basketball. So I'm going to try to play basketball. But after basketball, I'm going to become an entrepreneur. I don't know how, where, what,

I don't know what I'm going to sell, but I know I'm going to be an entrepreneur because what he's explaining here is way better than the prospects I saw in front of me, most of my classmates in college. I don't want to do what they're doing. I knew I was different from them. I was a C student in college, not because I lacked intelligence, but because I just didn't want to follow that program. It just didn't make sense to me. So that's the stage. That's the foundation, Alana, for why I got into marketing and became an entrepreneur. So when I was looking to become a pro player, mind you, that people pile that you mentioned, great metaphor. I asked myself, how am I going to separate myself from all the other players who want to play pro? Because a lot

of people don't know this, but worldwide, you have about 5,000 jobs worldwide for an American male to play professional basketball, about 5,000, actually 5,000 total male and female. And the NBA has about 500. So you got about 4,500 for the rest of the world. That sounds like a lot, right? But that's not a lot. How many men in America think they can play pro basketball? Go to your local Equinox. All right, you'll see. Everybody. Everybody thinks they can, but not everybody can. So I said, this is like a one out of a thousand chance. How am I going to make it? And most players, their mindset is, well, I'll just play. I'll just play and I'm going to be so good that it's going to be obvious and I'll sign. And that's the way most players

want it to go. And that's the way I would love for it to have gone, but I knew that wouldn't be enough. So what am I going to do or what can I do that these other players won't do? And I know a lot of athletes. Most athletes off the basketball court, they're lazy. So I figured, what can I do? I can sell myself. Let me see if I can get an agent. First, I went to an exposure camp. You know what those are? Ever heard of them? No. Okay. So exposure camp is like a job fair for athletes. Everybody knows what a job fair is. People with no jobs, but you want a better job. You show up to the job fair, talk your way into hopefully an opportunity, a conversation, coffee, a job interview, and you can move yourself up in your career. So exposure camp is like a job fair, but instead of

talking and handing out resumes, you bring your sneakers and you play. So it's a two-day event with 200 people, players. We all think we're good enough to play pro or advance our careers professionally, but at this moment, none of us have a contract. So this is kind of like a casting call, even more than a job fair, because we're all trying to get cast, but there's only five roles and there's 200 people. That's what it's like. So it's a meat market. So I went to one of these events and I played pretty well. It was only two days, Saturday, Sunday. I played pretty well at that event. I got a scouting report from an independent third party that said positive things about me. All

right, this guy is good enough to play pro. And I got the footage from that event. That footage was on this thing called a VHS tape. You remember those? Okay. So the VHS tape and the scouting report was the collateral that I needed to start selling myself because I understood if I just went to a bunch of agents, because agents are sports world, same as the literary entertainment world. They're the go-between. They know the people with the jobs and you're the person who wants the job. So they're the middleman.

I needed a middleman because I knew I was going to play overseas and I'd never been outside the country. So I can't call anybody over there, but they can. So I knew I needed an agent, but in order for me to reach an agent in Atlanta, I need something to show them that proves I'm worth their time. Because if I just called them and say, Hey, I'm really good. I can dunk. I can shoot. How many people are calling them saying everybody. So I needed some proof. So when I went to the exposure camp, now I had the proof. I got the VHS. I have the scouting report. This is just my mindset at this time. I'm just working backwards. So once I got those two things, I went on Google and this is 2005, by the way, and I Googled basketball agents. So any basketball

agent who had a phone number, I called them. So I called 60 basketball agents and I told all of them, basically said the same thing to all of them. Here's who I am. Here's what I have. I immediately got to that part. I got a scouting report from this pro exposure camp I went to, because that's credibility. And I have the footage, Mr. Agent, so you can see it. Don't just take my word for it. I can show you. I said, okay, show me what you got. Now, mind you, it's a VHS tape. There's not a link. I had to make copies of the VHS tape. I had a double-decker VCR at home. So any Gen Zers listening to this, ask your parents. They'll tell you what a VCR is. I was making copies of this. I was making copies of the VCR and mailing them in bubble mailers physically to the agents who were asking for the footage. So I called 60 agents. I spoke to 20. They said,

let me see what you have. Of those 20, one of them came through the funnel and said, I will represent you. He became my first agent. And that's how I got into pro basketball. That is such an incredible story. What's beautiful about it, even when you talk about it, you know, it starts with 60. You get to talk to 20. You don't talk about the 40 that ignore, reject, because again, that's inevitable. It's always going to be there. It's always going to be a numbers game.

Success is a numbers game, right? But the beautiful thing is how you're looking at one out of the 60, but you needed the 60 in order to get that one. Most people will stop way before that, which is interesting that you continue when everybody else stops, which is why you can live a dream and all the rest are trying to figure this out, right? But I think the other thing that you talked about is that disruption of professional education, kind of a big thing that we stand for, because it really doesn't teach you how to move that lid on yourself, on their leadership, on your

money beliefs, on your capabilities. So I just love that point, which I think to me is really, really interesting. I think many, many people don't realize how much we're holding ourselves back. And that's the biggest thing that we need to start elevating. But tell me again, you hustle your way in. And I think at some point, you're also starting some kind of a daily motivation, weekly or weekly motivation videos, right? So talk to me a little bit about that. Because I think, again, it just shows your grit, tenacity. And also, even if one door doesn't necessarily open, other doors were open, right?

Which I think this is just beautiful to see you. Dre, can you share a little bit? So the agent gets me on first contract. I go play in Lithuania. That's where I start my career, 2005. Now I take that VHS tape. I take it to an audio visual store and get them to put it on a data CD because anybody knows, remembers VHS that

you only have one copy of your footage. So if anything happens to that tape, it's gone. So I didn't want that to happen. And now the internet is starting to become a thing. We don't know quite what yet. I guess this is web 2.0 for people who know that lingo. So there was a new website out that said you could put as much footage up here as you want for free. It was called YouTube. So I took that data CD and I uploaded my footage from that exposure cam to YouTube. And I just put it on YouTube just for myself. This was no grand scheme to market and promote myself. That wasn't the plan. I wish I was that smart.

That was not the plan. I just put it up there for me just because I didn't want to lose the footage. That's the only reason I put it on YouTube. And I forgot about it because who cares about YouTube in 2005? Nobody. So I'm playing ball. I'm traveling. I played in like three or four countries my first four or five years and playing pro ball. And I would put videos up and then I saw people were responding to the video. Maybe six months later, there were comments on the video and people are like, who do you play for? Where'd you play? What school did you go to, et cetera. And I immediately realized, light bulb moment, that there's an

audience of people who want to learn basketball and they're just going to the internet looking for anybody who can help. Because they were not looking for Dre Baldwin. Nobody knew my name at that point. And mind you, I'm playing overseas. So most Americans have no idea what's happening overseas, in basketball especially. So they don't know me. They're just looking up basketball, and I just happen to be there. So I realized that there was an audience there, but at the same time, so what? It's not like there's any money I can make from this. I had no products to sell. There's no ad revenue. There's no such thing as an influencer, and there's no such term as social media. So who cares about this stuff? So if you're a blogger or a YouTuber in 2007, what are you? You're some loser living in your

parents' basement who needs to take a shower, shave, and get a real job. That was the mindset of people looking at those people back then. It's changed now, but that's how it was. So I didn't care. I put videos up sporadically every six months, every six weeks. Whenever I got around to it, I put a video up. So I start to slowly, this audience is building, but I'm playing. My main thing is I'm playing basketball. I'm traveling. I'm putting videos on YouTube every now and then. 2009 phone is not ringing. I'm a free agent. I don't know if it's going to ring again. So at this point, I just read another book. This was the millennial, new millennium version of Rich Dad Poor Dad. It was called The Four Hour Work Week by Tim Ferriss. And Tim,

a lot of people don't know this, but his book blew up because of his blog. He had a very popular blog before the book came out. And I would read his blog. And he had this little experiment that said, hey, here's how you can test out a digital product and sell it online. I followed the experiment. I had an audience of basketball players, right? Now, the reason I followed the experiment is not, again, not because I had this big grand scheme of being a businessman. That was in the back of my head from back in 2002, but the phone's not ringing and I need to make

some money. I'm in my mid to late twenties at this point. I'm like, okay, I need some control over my life. If the phone doesn't ring again, what do I do? So this was perfect timing. I follow it. I create a couple of products, one for how to dribble the basketball, one for how to shoot the basketball. I priced them at $4.99 a piece. I put these products out and they immediately started selling. And when I made my first sale, I said to myself, I can do this for the rest of my life. Because what I had done is I created what I now know to be intellectual property. You create an idea, turn it into a tangible thing, put a price tag on it, present it to the market, and exchange it for money.

I said, I'm not going to be able to jump 40 inches in the air forever, but I will be able to take an idea and turn it into a product forever. So that's how I actually started making money, $4.99 a piece. So now the mindset piece that you asked about to finally answer your question. The players who were following me on YouTube, they started to get interested in me, the person. So at first, they just came to me because I had the information. And this is a key thing when it comes to branding and marketing, especially when you're building a personal brand. Simon Sinek has a book called Start With Why. The thing that connects people to you is not your information or your skill or how good you are at the thing.

It's why do you do what you do? That's the emotional connection. And once the players saw that I knew my stuff, like obviously this guy can dribble, shoot, pass, do the crossover, he can teach me the Kobe move. Then they wanted to know who is he? And they started asking about my background. And that's when I started to share. One year high school, didn't start playing until I was 14, walked on D3. All right, the reason I'm in this empty gym in Miami while basketball season's going on because my phone's not ringing and I'm waiting for my phone to ring so I can play again. So the players started to connect with me because for every one LeBron James, you got a thousand Dre Baldwin's. So you got the guy who goes to Yellow Brick World because he's just so good that the opportunities just keep coming. But then you got the guy who wants to go, but the opportunities aren't coming. It's stop and start. It's up and down, up and down. So many players could relate to me because they got cut from their high school team. They had to walk on to play in college. They didn't have anyone around them believing that they would make it as an athlete, but they believed. So when they saw me and I had actually

made it, quote unquote, they're like, okay, well, if he did it, let me see what this guy's doing. Maybe I can follow his path. So as they kept asking me questions about mindset, Dre, why do you keep coming to the gym to work out? Because I want to work out every day too, but I just don't have the motivation to do it. Or how do you get the confidence to come to the play in the practice or in the tryouts rather that two-day exposure camp?

People don't understand about the sports world, Amana, that you practice all year for one day. You need it one day. If you have one bad day, after all that year of practice, you got to wait another year to get another chance. It's a cutthroat. It's a cutthroat game. So they ask about that. Or they would ask, well, Dre, with your background, high school, college, you're not signed to a contract right now, but you're good, but you're not signed. What keeps you going? Why keep trying? Why not just give up? Because I should have given up. A logical, reasonable person would have given up. I am dumb enough to have kept trying. And then they would ask, well, how do you get started with all this stuff? Because at this point now, I got a nice little name to myself on the internet. Now

I'm somebody on the internet and I played overseas. And it's hard to find information on how to play overseas because it's not like being a lawyer. Like a lawyer is go to school, go to college, go to law school, pass the ball, you're a lawyer. All right. There's a process and it's clean. To be a professional basketball player, there's no process.

There's no step-by-step color by numbers. And I started answering these questions. So I started talking these questions. So I started talking about discipline, showing up every day, confidence, putting yourself out there, mental toughness, how to keep showing up and putting yourself out there, even when things are not working and when success is late to the party and taking initiative, how to make things happen instead of waiting for things to happen. And I started talking about these in these videos, finally getting to the answer to your question here called the weekly motivation. So at this point, I was starting to put out YouTube videos

every day because now Google has purchased YouTube. This is about 2009. So now they say, when your videos get viewed, you'll make a little bit of ad revenue. So I'm like, all right, my phone's not ringing. I might as well get that. Let me get the ad revenue. So I started putting videos out every day on basketball. It was just basketball stuff. So every Monday, I did the weekly motivation. That was a mindset video. So it wasn't about sports. It was just about mindset because this is what the players were asking for.

They wanted to know the mindset. So when I started doing those, I did those every Monday for 400 Mondays in a row, weekly motivation. And what happened is two things. Number one is the players appreciated it, of course, because they all were coming to realize after five years of getting the skills, they came to realize that without the mindset, the skills were not actionable. They couldn't activate the skills without the mindset. So they appreciated that. The other thing was people who didn't play sports started to find me online. And they started saying, Dre, I don't even play basketball. But the stuff you're saying in these videos applies to me.

And I have my own IT firm. I am a teacher. My son was watching your video and I heard what you were saying. And that stuff applies to me as well. They would say things like that. And that told me I got a whole audience of people I can serve who don't play sports. Now, why do I care? Because I'm a basketball player. I'm a pro basketball player. I could teach basketball players the rest of my

life. I could be a basketball trainer. I could be a coach. I can do that for the rest of my life. And there are plenty of athletes who do. So why did I care that people who didn't play ball liked my message? Well, let's go back to 2002, that network marketing meeting. All right. I was thinking bigger than just sports. I said, I want to have a message that expands beyond the sports world because I was never so good at sports that I could just rest on the walls of athleticism or being an athlete. I figured at some point in my life, the sports thing is the gravy is going to stop running and I'm going to have to do something outside of the world of sports. Now, luckily, I had a nine-year career as a pro athlete, which was, again, not in the cards, but I always had my mind on something bigger than just sports, and I knew I had more skills than just sports. So that's when I realized, okay, I can expand my audience, which is what I started doing, and it naturally kind of happened. So also around this point, Ilana, self-publishing becomes a thing. Now you can write your own books.

You don't have to go through a publisher. So I started writing my own books. Now, if I can make a $4.99 basketball program, why not make a course on mindset? And I started doing that. And I started doing these things. I started creating all these digital products and programs. And from 2010 through 2015, I stopped playing in 2015. I had two careers going at the same time. I'm doing the basketball stuff. And now I'm building this, what we now call brand online. So now I started calling it work on your game. Now I've got these people who don't play ball following me. Now I've got these people who do play ball following me. Now I got the ball players who, many of them didn't make it pro, right? So a lot of people who play sports, their careers end in high school. Some of them end in

college. Some of them end after college. So they're leaving the sports world and moving on to other things in life. But at the same time, they're still connected to me because now my message is bigger than just sports. So now there is still value in listening to Dre, even though I don't play ball anymore. So it was, again, I wish I could say I had this all as a big strategy. It didn't, it wasn't like that. It kind of just happened naturally. But even to this day, I haven't picked up basketball in 10 years, but I still have people from the basketball days who are still in my audience to this day. So that's a long answer to a short question, but that's how it happened. So it's such an incredible story because first of all, it's amazing to me how many similarities we see between my tech world, corporate, and the world of sports.

There's a lot of things that are not the same, but I think there's a few things that your need to adapt, reinvent yourself and leap again, again, again, is continuous. And it's amazing to see how you realize all these potentials and you jump on them even before they're even a thing, right? So you keep on reinventing yourself, which is super strong. But I think the other thing that you mentioned is at least in corporate, if somebody would have said the word mindset, I would roll up my eyes and say, oh, this is BS. All I need is a strategy, strategy, strategies. And the truth is, it's like 90% mindset, 10% strategies, and maybe a little bit of luck. But I think it takes me a long time to realize that what was holding me back wasn't the strategies. The strategies might be simple. I just need to put

a video out or I need to put a post out. But it's the mindset of what we people say and what if I fail and what if I look like an idiot? It's the mindset. It's easy to get up when things are successful. How do you get up from a failure? Everything you said, it's just really interesting to see the similarities. But talk to me about a hard moment because, you know, when you talk about it, it seems almost easy for you, right? Share a hard moment, if you will.

Well, it's easy to talk about it because I know my story. So it's easy to talk about it. It was not easy to do. So I make it sound simple. But no, this is a 15-year story that I'm telling you. So let's take it out of the sports world, go to the business world. So I decided that I was going to stop playing ball. This is around 2014, 2015.

I stopped playing 2015. And my first idea was I was going to become a professional speaker because I didn't even know such thing as a professional speaker. But then when I found out and I was already making all these talking videos on YouTube, I said, okay, well, I can speak. I don't have a problem speaking in front of crowds. No nervousness of public speaking. Let's see if I can get into this game. And I didn't really know how to do it, but I met somebody who met somebody who knew a, someone who was full-fledged already in the game. She kind of taught me the ropes and she said, well, this is what you're going to have to do, right? She said, you're going to have to make a lot of calls, make a lot of cold calls, no problem doing that. You got to send a lot of emails. You might get a CRM to keep all this under

control. And you're probably gonna have to do some speaking for free in order to make it work in order to kind of get some traction, prove your proof of concept. And I said, all right, cool. So that first year, 2015 going into 2016, I did a whole lot of calls that didn't get answered, a whole lot of emails that did not get responded to and offered to speak for free. And many times got turned down anyway. And I got a lot of times they said yes, but the times that I did did speak for free, I got to prove myself, get some footage, get some proof that I was good,

did a couple of TED Talks early on. And that really started to create the momentum for me as far as being accepted as an entrepreneur. The good news is, because none of that was really making me any money, the good news is I already had my products from the basketball days and the mindset stuff, that stuff I was still selling. So that kept me going as far as like, you know, if I had to show the IRS I made any money that year, it was from

the stuff I'd done as a basketball player. It wasn't for anything I was doing as an entrepreneur. It wasn't making me any money, not yet. At least not a business guy entrepreneur, not the basketball entrepreneur. So that first year, probably 2015, 2016, going into 2017, there was really no traction as far as the non-basketball material. It wasn't until about 2017, 2018, that's when I started to get some paid speaking gigs. People started coming, asking for coaching and getting into the consulting spaces. That's when that stuff really started to actually work. And I realized probably about 2017, 2018, that I couldn't just walk into this world, that I needed to get educated again, same way that those network marketers were educating, the same way going to college, you get educated, same way as

a basketball player, you have to learn the game. I had to learn the game of being a businessman. At that point, I was a product creator and I was damn good at it. And I had an audience, but I was not an entrepreneur because I couldn't explain to you entrepreneurship in 2016, even though I was making money. Through entrepreneurship, I could not explain entrepreneurship. So I didn't really know the game. I realized I had to re-educate myself. And that takes a good dose of humility, especially for an athlete, because as athletes, a lot of people don't understand this from the outside looking in. Being an athlete is essentially a part-time job. It is a full-time job because you have to train.

And when you add in the training and the recovery, yes, it's a long day. But you don't get paid for training and recovery. Same way that someone who works at an office doesn't get paid for driving to and from work. It's the same thing. You don't get paid for that. Our actual workday is about two to four hours a day. A long day is four hours of work. Most people work eight hours a day.

And our seasons are not year-round. Our seasons are about four to six months. So if you normalize the salary of an athlete, you got to double it for the time every day and then double it again for the fact that we only work half the year. So when people really think about it, it's a part-time job. Athletes get mad when I say that and I say, well, I'm an athlete, so I'm allowed to say it. So anyway, to be an entrepreneur is a lot more work. Being an entrepreneur is a lot harder job than being an athlete. Being an athlete is the best job I ever had. It is way easier than what I do now. So the whole point is I had to humble myself and get educated again as to how this game works.

Because the same way that I had to learn the fundamentals from the ground up in sports, you got to learn the fundamentals from the ground up in business. And that's what I've been doing and still consider myself a student. I still consider myself relatively young in the business world. So again, I stopped playing in 2015. It hasn't even been 10 years yet. So really just learning. I don't think there was any one particular moment of terribleness for me as an entrepreneur. It was just understanding that I had to learn the game again and understand that there's a lot harder game and there's a lot more work involved and there's a lot more competition.

At least in sports, if you play for the Miami Heat, you know, okay, we got the Knicks, the Lakers, the Nuggets. You know who all your opponents are. The business world is highly subjective. It is about who likes you. It is about relationships. It is about strategy. And it is about systems. And you can be really, really good at your thing.

I can be the best speaker in the world. It doesn't mean really, really good at your thing. I can be the best speaker in the world. It doesn't mean I'm going to book any stages. I can be the best writer in the world. It doesn't mean I'm going to sell any books. I can be the best whatever podcaster in the world. It doesn't mean I'm going to have any listeners. So you have to have other elements besides just being good to succeed in business. Whereas in sports, if you're just good, that's enough because the structure and the systems and the relationships are done by someone else. But in the business world, you have to do all that stuff. And that's a whole other ballgame is the reason why many athletes want to transition into business.

But it's challenging for them because they don't understand how much more work it is in the business world as opposed to the sports world. And I love that you said that, Troy, because I think one of the key things that people don't realize is that you go to entrepreneurship because of your why or because of some passion. But most of the time, what you're going to do is you're going to put your sales hat and your marketing hat. Do you need to hustle in business development

and partnership? And like, you're going to hustle. And it's interesting, like, I feel like with experience, you actually need to get a lot more humble. Because to some extent, when I was young, I was confident. I was like, yeah, I'm going to kick ass, you know, I got it. But to some extent, when you get experience, it actually you realize there's a lot more, it's a lot harder than you expected. You know, I remember from time to time talking to people, I'm like, yeah, I want to create my billion dollar company. I'm like, let's start with your 10 million revenue and talk to me after. So I think we also get a little bit of humbleness as we start. But you

still had marketing campaigns for Nike and Wendy's and Gatorade and NBA and Jordaned it. Samsung, you've hustled to get yourself into some of the most prominent companies in the world. Maybe some tips, like what helped you drive? Great question. Two things. Number one is I started something when nothing existed. So that's the personal initiative. Many of the brand deals I did happened because I was known in a space that was starting to become visible. People were starting to pay attention. So I would say the tipping point for social media as far as the creators and these what we now call influencers is probably about 2012 through about 2013, about that range.

That's when it tipped from about 2009 to 2012. There were a bunch of people consuming the internet, but they were not producing. So those were the days when I basically killed it for those four years. Let's just put it that way. In terms of the content I was creating, the products I was selling, there was very little competition, but there was a lot of audience. Then by about 2013, people stopped watching and they started making. Now you have competition. Now everybody's a creator. That's when it flipped. And our rhythm changed as well. That happened also.

So the answer is because I had an audience before it was normal to have an audience, I was able to make relationships and build connections with companies. And they were looking to connect with people. They were kind of early on it. And then the consumer saw it and everybody jumped in. So that was one thing is just being a first mover. I guess, does they call it the first mover in business? First person out there. So I was the first person creating basketball content for free on the internet. Nobody was doing it before me. And basketball players know that. The other thing is the relationships. And in the relationships, there were other people, they were creators on the internet because they were creators. So let me explain what I mean by that. I was a creator on YouTube

with basketball content because I'm a basketball player who happened to be on YouTube. I was not a creator who happened to talk about basketball. I was a basketball player. I just happened to have a cheap little $100 camera and I brought it with me to the gym and I made videos. I was not on YouTube because I was trying to be a YouTuber. But again, in that time period that I told you that tipping point, then you started to get these people who came to YouTube to be YouTubers. That was their point. Basketball just happened to be the topic. I was the opposite. I was a basketball player who happened to be on YouTube. There's a difference. So I know many of these guys who were YouTubers and basketball was the subject. I knew them because

they knew me. They knew me because anybody who looked at YouTube for basketball between 2005 and 2013, they all know me. So I built relationships with many of those guys and they were coming in it specifically for business. And they were looking to build a brand and get known. And many of them, they would do like review sneakers and tell you why this sneaker is better than that sneaker. Now, because they're doing that, well, what did the companies do? Nike and Jordan and Reebok, they said, oh, let's build a relationship with these guys because these guys will help us sell more sneakers. And they did. And they would build relationships with them. And even one guy I knew, he told me this personally, because I was, for example, I was out in California once. I'm in Miami. I live in Miami. I was in California visiting. And there was a YouTuber out there who I knew of. And he was a YouTuber, basketball player, but YouTuber, not professional player, but YouTuber who played ball. I told him I'd be in California. He was like, yeah, just come through, come play, pick up basketball with us. I played with him. We sat in his car for about an hour and a half after we played basketball and we just talked, just building a relationship, connecting. He was asking me questions about business. I was asking him questions. I was telling him about things, about the contracts and how these companies work and things like that. And we just built a relationship. So we consider each other friends. So he went and got a deal with Jordan, Jordan Brand. The good thing about Jordan Brand is they send a lot of free stuff. So Jordan, he builds with Jordan Brand. He builds a connection with them and they want him to be like their main influencer guy. And he told me this on the phone with them. And they say, hey, by the way, what other YouTube guys

slash influencers should we connect with and bring them in on this deal? Because we don't want to just have one guy. We want to have like four or five. He mentioned my name. Jordan didn't come looking for me. They came looking for him. But because I knew him, he mentioned my name. And that's how I got in, for example, with them. So a lot of times it was not, Dre is just so amazing that the world beat a path to my door. I wish that was the story. And if it was, I would tell you that wasn't the story. It was just, I have relationships. And I realized that very early. I realized that even way back when I was trying to get on in basketball, that the relationship is

the key. Because there are many times in my pro career, when I was, remember I told you about the phone not ringing. And many times I was able to make that phone ring because I knew someone who knew someone and they can make the phone ring and they made the phone ring on my behalf. So I realized that in business, that it's not being good. You can't just skill your way to the top in business. If that was the case, a lot of people who are known for being successful would not be the known people. And there are a lot of unknown people who will be the known people. A lot of it is relationships. A lot of it is strategy. And a lot of it is the system. Who do you know? That's the most important thing. And you need to be good. Don't discount being good. Skill matters. I mean, after all, I'm going to work on your game,

guys. So have game. But if you don't have the right relationships in the business world, it will destroy you. You can be really good and really frustrated because people don't know you. So if I had to point to one thing between those two, I would have to say the relationships. As much as it may pain some people who think that the skill is all they need, it's not the only thing you need. You have to know the right people in the business world and your communication skill, your ability to build with the right people and have the right people have a favorable opinion of you is everything in business. And you can get a lot more done

through the right relationships than you will ever get done through hard work. I can't stress that enough. What you said is so spot on. And there's a saying, connections is the new currency. And I do believe everything is happening in the hidden market.

People know you and people will bring you in. And that is about relationship, building that trust that you've been able, again, to early on start leaning into, which is pretty interesting because you've been that early adapter that just keeps on adapting, which is really, really interesting. I think the other element is the fact that you've walked the walk. So you're not just talking about it. This is not just motivational stuff. You walk the walk. You needed to get back up every single time. And I think there's a different level of authenticity when you come from that area. The one thing that I do want to ask you a little bit about, I think you

have one video that talks about why do winners always look in the mirror? That saying to me is so strong. Can you talk to us a little bit about it? The concept is winners look in the mirror and losers look out the window. And where that came from was, it was just just a self accountability. And that's a big thing over here in our world is self-accountability. And this goes back to the athlete days because when I only played one year of high school basketball, it's not because basketball was not on my radar. I tried out the first three years. I just didn't make it. I got cut freshman year, sophomore year, junior year.

I made it senior year, and I sat on the bench senior year. So I can tell people I had a front row seat, best seat in the house, right there on the bench, watching the game from the front row. And when I started putting my YouTube videos out, what happened is a bunch of up and coming ballplayers, again, I told you these are 13 to 24 year olds, they were facing those same challenges and they would come to me and say, well, Dre, look, I tried out for my high school team. I didn't make it. I think the coach is hating on me or the other players, they wouldn't give me the ball or these guys hate me.

So they're not giving me the ball or whatever the situation is. And I would always turn it back on them and say, well, maybe you're just not that good. Maybe you just can't make a layup. Maybe you can't make an open shot. That's why you didn't make the team. And mind you, I don't know these kids, right?

So I would say to them, look, maybe you're right. Maybe the coach is hating on you. Maybe all the other players at school conspired to make sure you didn't make the team. Maybe the coach is hating on you. Maybe all the other players at school conspired to make sure you didn't make the team. Maybe your parents are trying to block your goal of being a basketball player because they want you to be an engineer so they won't take you to the park. Maybe that's the situation. Maybe that's true. However, what can you control? You can't control the coach. You can't control the other players and you can't control your

parents. All you can control is what you do. So what can you do to maximize your ability on the court to make sure that if anything else is the reason, it's not that? And I would emphasize that over and over and over again to the players and that self-accountability issue, the self-accountability topic, because it's about ownership. And when you take ownership of, you have power over. And what you take power over, you have power over. And what you take power over, you can control. And if what you do not take responsibility for, you cannot do anything about. And the biggest challenge that I noticed with athletes and still to this day with non-athletes is that a lot of times people abdicate that responsibility because they would rather

point the finger at someone or something outside of themselves. And it's not that they're necessarily wrong. It's just that when you're pointing the finger at something else, if that or them or it is the reason for your failure, well, what are you going to do? You have no power. You can't do anything. And the mindset of the successful person, I've read enough personal development. I've done a lot of it. The mindset of a successful person is that there's always something that I can do about the situation, regardless of what everybody else does. There's always something that I can do. And that goes from whether you're talking to religious texts, to the more secular stuff, to the Jack Canfields, to Napoleon Hills, to Robert Greene, to 50 Cent, to anybody who talks personal development. There's always what can I do about the situation that I

can take control of the circumstance. And that self-accountability has always been a big deal for us. So that's why I say to people, if you're a leader, you always look in the mirror. The first question you should always ask yourself, I'll tell you a story. 16 years old, I'm playing in a recreational league team. So this is my junior year, I'm 17. So last year, I wasn't on the high school team. And our team in the recreational league was really good. We went all the way to the championship. Championship game, I played terrible. I wasn't making any shots. I scored like the first two points of the game. I didn't score again the rest of the game. So we ended up losing the game. Championship game. We hadn't lost any games all season. That's the only game we lost was the championship. So we lose the championship

game and the coach takes me out at the end and I'm mad at the coach for taking me out. And one of the other coaches came up to me after the game and he said, Dre, before you get mad at the coach or anybody else, look at yourself. Ask yourself what you did tonight. He was 100% correct. And I had to take ownership of that. And this is why I always tell people, if things are not working in your favor in your life, you got to ask yourself, what did you do or not do that led to this situation? Because you can at least do something about that. You cannot control anything that anybody else does. And we only control about 1% of life.

I tell people this even when I give my keynotes, I talk about this. 99% of life is out of your control. You don't control the internet. You don't control the weather. You don't control other people as much as you think you do. You can influence them. You don't control them. All you can control is you and your mindset and how you respond to the situations around you and how much

of that 1% you decide to take ownership of determines who you become in life. And that applies to everyone. And most people end up looking out the window when things are not going in their favor and looking for something outside of them to fix the situation when instead, if you looked in the mirror, you would actually empower yourself. So that's what that concept is about. So to me, any type of success is all about that extreme ownership that you're talking about. And keep asking yourself, you know, you're either going to be the victim or you're going to be the victor. Is this getting me closer to my goal or not? And if it's not getting me close to my goal, I need to wipe it and I need to continue

because that is not serving me. So I love that you said that, Trey. We do have a little tradition in the podcast to look at yourself now and advise your younger self, wherever that means. What would be probably an advice for yourself that you wish you knew earlier or you would have helped you along your journey?

I'll tell you three things, I'll be quick. Number one, invest in yourself, invest in personal development as quickly as possible, as soon as possible. So my son will know about personal development as soon as he can read, whereas I didn't learn about it till I was 21, 22. So that's number one. Number two is speed and urgency, acting with speed and urgency, because anytime we come across a breakthrough in life, and I that works. We're like, man, I wish I knew this 10 years ago. I would have achieved so much more. I would have done so much more had I known this earlier or had I, I knew about it, but I didn't do it. I wish I had done this three weeks

ago. I wish I had done this last month. I would have had a lot more success. That's number two, urgency and speed. And number three is invest in relationships. Most valuable thing, even though I mentioned college and it wasn't teaching me anything about thing, even though I mentioned college and it wasn't teaching me anything about business, even though I have a business degree, the relationships that I made in college are very valuable. And if I could invest in one thing even more, if I was to go back, I would go to college again. I would just make more friends and hang out more and socialize even more because I would build more relationships that lasted for the rest of my life. So those three things, personal development, speed, and relationships. I can relate to every single one of them. And I think for me, I wish

I woke up and got a little bit more of that self-help for me, because I always thought it was just that engineering degree is what's going to help me get further and further in life. And that doesn't. So I wish somebody woke me up. But I'm glad I woke myself up, right? We're looking at ourselves. So I love that. And I think you mentioned that, I mean, you have dozens of books, but there is maybe a book that you're willing to give to our audience and also work on your game, university. Do you want to talk a little bit about that? Sure. So it's my book, The Third Day. I give people a free copy of it. So all we ask is just to just cover the shipping. We'll send you a physical

copy of the book, paperback. All you do is go to thirddaybook.com. Now what this book is about is the subtitle is A Decision That Separates the Pros from the Amateurs. So this book is all about how you show up and give your best effort when you least feel like it, which as a professional is a requirement because you don't have the option of taking the day off when you don't feel good. You still have to show up and give your best effort. So the third day is what we call those days when you don't really feel like it, but you have to anyway. How do you give your best effort then systematically and strategically? This is not a rah-rah motivational book. You might get motivated, but that's not the point. The point is give you the system and the strategy to do it. And again, thirddaybook.com. The book is book. You might get motivated, but that's not the point. The point is give you the system and the strategy to do it.

And again, thirddaybook.com. The book is free. You just cover the shipping and we'll give you a free copy. And another thing you mentioned, Work On Your Game University. That's the place where we do all of our coaching, our consulting, all of our speaking. Most of our focus these days is inside the university because that's where we work with our high-level performers and people who want to be high-level performers. So that's just work on your game, university.com. And we'll have all the links here for our listeners. Dre, this was so inspiring. I enjoyed

every minute of it. I'm sure the audience do. Thank you for all the insights, the authenticity, the love that you bring to people, which just shines through with every sentence. So thank you so much. Well, I appreciate the opportunity. I appreciate you sharing your platform, Ilana, and I'm looking forward to hearing feedback from the audience. It's going to be a good feedback for sure. you