Mastering the Business Pivot with Athlete-Turned-Entrepreneur Dre Baldwin

What transforms an athlete into a business mogul? Dre Baldwin, CEO of Work on Your Game, joins me, Mackenzie Kilshaw, to unravel this enigma, sharing his incredible evolution from basketball courts to business. With the agility of an athlete, Dre navigates through his past, revealing how the principles of sportsmanship powered his rise to becoming an inspirational force in business. This isn't just a conversation about personal triumph; it's a masterclass for anyone yearning to channel their competitive spirit into entrepreneurial success.

Embark on a journey with us as Dre decodes the art of asset creation and the importance of molding a brand that outlives the ticking clock of an athletic career. His strategic playbook flips the script, turning the ephemeral into the enduring. From launching innovative basketball training programs to the world of digital products, Dre's story is an inventive blueprint that demonstrates how to convert passion into a legacy. His approach strikes at the heart of modern entrepreneurship, where the digital landscape is the new arena and adaptability is the name of the game.

As we pivot toward the end of our insightful session, Dre lays the essence of what it takes to transition from sport to the speaker's podium with the finesse of a seasoned pro. It's a candid look at the importance of discipline, mental grit, and the proactive hustle that defines a true champion—both in athletics and business. Dre's journey is not just one of navigating change but also a testament to the power of self-belief and the relentless pursuit of excellence. Tune in for an episode that scores points not just in play but in the playbook of life's grand game.

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Chapters

• 0:27 From Basketball to Business
• 7:13 Creating Assets and Building a Business
• 16:48 Transitioning From Athlete to Speaker
• 27:11 Importance of Discipline and Mental Toughness
• 35:19 Importance of Personal Initiative in Success

Transcript

Shauna Foster: 0:27

Winning is your guide to making it in business. Join our award-winning host and entrepreneur, Mackenzie Kilshaw, and special guests in casual conversations that will educate and inspire you on your business journey. Winning will help you learn the hard lessons the easy way, with guidance from celebrated entrepreneurs and business leaders. It's fun, it's informative, it's winning.

Mackenzie Kilshaw: 0:53

Hello, welcome to Winning. I'm your host, Mackenzie Kilshaw, and today's guest is Dre Baldwin. Hi, Dre.

Dre Baldwin: 0:59

Hey Mackenzie, how are you?

Mackenzie Kilshaw: 1:00

I'm really good. How are you?

Dre Baldwin: 1:01

Excellent. Thank you for having me on.

Mackenzie Kilshaw: 1:03

Yeah, it's really great to have you on. Dre is the CEO and founder of Work on your Game Inc. He has given four TEDx talks on discipline, confidence, mental toughness and personal initiative. He's also authored 33 books. He's appeared in national campaigns like Nike, Wendy's, Gatorade, Buick, Wilson Sports huge, huge campaigns. He has published over 8,000 videos and his content has been viewed over 100 million times, which is amazing. Dre also has a podcast, Work on your Game. It's a daily podcast where he has over 7 million downloads. So, Dre, I'm really excited to talk to you today and talk a little bit more about working on your game. So, thanks for being here. Do you want to tell the audience a little bit more of who you are and what is Work on your Game?

Dre Baldwin: 1:54

Sure. So everything you said in the background hopefully I can live up to in your introduction there. I grew up in the city of Philadelphia, now based in Miami, always played sports growing up, got into basketball pretty late around age 14, was as late if you're trying to go play in college or let alone playing in pros. I only played one-year high school ball, walked on to play Division III college ball. I had to hustle my way into pro basketball, which I was able to do, luckily, and at the same time started publishing to this brand new platform called YouTube, and that's where I started to build the name for myself online, and it was mostly just the basketball players.

Dre Baldwin: 2:25

But after a few years the players started asking questions about my approach because they just saw I was really consistent, and this is way before consistently publishing online was a thing, and they started asking about mindset. So I started talking about it and people who were not athletes started hearing the videos about mindset and saying, Dre, this stuff applies to everybody, this doesn't just apply to sports. So that's how I knew what my segue would be from the sports world to an audience of people who were not athletes, and that's exactly what I did in 2015 when I stopped playing, and that's pretty much what I've been doing full time ever since. So my company now, as you said, is Work On Your Game, and what we do here is we take the tools to help athletes reach the top of the sports world and we apply those tools to the business world to help professionals form at their highest level, do so consistently and, of course, make money.

Mackenzie Kilshaw: 3:10

Yeah, I love that and really, if you're looking at it, the sports world and the business world are actually quite similar, right. It is a lot of hard work, dedication, having the right mindset to get you really where you want to go, and they do correlate a lot, so it's really cool that you went from sports to the business world also.

Dre Baldwin: 3:31

Yes, thank you. Yeah, yeah, there's a lot of connections.

Mackenzie Kilshaw: 3:34

Yeah for sure. So you started out with sports. I know, like you said, you didn't start till a little bit later, kind of an early teenager. Did you always want to be a basketball player. How did that? How did that start? What was when you were younger? What did you want to do? How did it grow from there?

Dre Baldwin: 3:52

I just wanted to be someone who was known. I want people to know who I was, and I think athletics was the vehicle. Simply because I was. I always had the athletic gene, so I was always playing sports. You know a little bit of football, a little bit of, you know, touch football, not serious football, kickball, backyard basketball, that kind of stuff. You know running, you know jumping over stuff, those kind of things. I knew I was athletic. I was at least more athletic than most of the kids on my block. But you know what, do you know? You're just in that small space and I tried a bunch of sports. You know, tried football, never really played football, did a little bit of baseball wasn't really that good. So basketball was the sport. That was just a natural progression.

Dre Baldwin: 4:32

Just where I'm from, everybody plays basketball. Because you don't need equipment no, it doesn't cost anything to play basketball you just show up and you have one ball and a bunch of people. You have a game. That's how I just naturally gravitated towards basketball, because that's what was happening in my environment. And luckily I was no tall, long arms, I can run and I can jump. You know I'm black, so that must mean I'm good at basketball. All right.

Dre Baldwin: 4:54

So then I just I kept playing and practicing by myself. I wasn't good when I first started, but I got good because I just kept practicing on my own. Good thing about basketball is you can practice by yourself. So I just kept practicing on my own at the local playground and the afternoons in the summertime when it was too hot for everybody else, and so I had some space to myself where I could actually practice. I had a little sandbox for basketball, I guess you can say. And that's how I did it.

Dre Baldwin: 5:17

So to answer your question, was it my vision to become a basketball player? Not, at first, my vision was just to become known somehow. And then, because I was athletic, I figured it would be through sports, but I didn't know which sport. And then finally, once I got to basketball and no, when I started off I wasn't good. But as I continued to practice and I got better, I started to think, well, maybe this could actually happen and luckily, in some ways it did. I mean, it's not like I can't go to the grocery store by myself, I'm not that famous, but I did make it as a basketball player.

Mackenzie Kilshaw: 5:48

Yeah, for sure. Yeah, you played pro and you played in eight different countries, and overseas too. So you, I mean you made it in the eyes of making that your career, for a point in time, for sure.

Dre Baldwin: 6:01

Yes, I did. You're right about that.

Mackenzie Kilshaw: 6:02

Yeah, so you obviously practice is important to you. You've been talking about that a lot and how that helped you. So when you went from your professional career, were you already, guess, working on work on your game, or was it just something that you did in theory, or how did that business aspect come from your basketball?

Dre Baldwin: 6:30

Yes, so start putting content online in 2005 and this was all basketball stuff and then around 2008 and around 2009, 2011 and this two-year span, three years conclusive. This is inclusive. This is where things started to change, because in 2009, I found myself unemployed from basketball. So, in other words, I was a free agent. No, the phone wasn't ringing. Yep, and I already had an audience of people online. I've been blogging as well as putting videos on YouTube, so I had an audience online and the internet was starting to become we were, I guess we were in, I guess, what they call web 2.0, where you could basically put yourself out there and publish yourself and blogs and your own websites and sell stuff, and all that stuff was starting to become a thing. Yeah, I had an audience. Phone wasn't ringing and I need to figure out what to do, because I wanted a way to basically have control over my destiny, make money and still have something to do with basketball, because if the phone doesn't ring again, then I need something to do. So I had just finished.

Dre Baldwin: 7:27

Well, years earlier I had read Rich Dad, poor Dad by Robert Kiyosaki, and that was through just a random connection. I got in the network marketing which I didn't build a business in, but that experience opened me up to some new things like personal development and books on business. So he talked about having assets, how assets can put money in your pocket and you don't have to be your only asset by just working and making money. Because even though being an athlete is a job that most people will see as a dream job and it is, at the same time, it can see, when you're an athlete is still job. You only get paid when you're working and if you're not working like I wasn't at the time You're not making any money. So assets, so how do I create assets? So I had kept that idea in the back of my mind. So now I just finished reading the new version of risk dad, poor dad for the digital age. It was called the Four Hour Work Week by Tim Ferriss also great, yeah, right.

Dre Baldwin: 8:18

So Tim was just talking about a lot of similar things not in exact same vein, but a lot of similar things just using the internet for it. So how can you outsource and hire somebody in India to work for you? I never thought of that before or how can you, again, be more efficient in doing your work through using the tools of the internet? At the time, which was again 2008, 2009 so he had a blog a very popular blog at the time, still popular where he talked about if you have an audience, or even if you don't. Actually, he said if you have an idea and you want to create a product and sell it online, here's what you do. He had this little, basically little process of what you do. I followed the process because at this point, I needed something. So, as they say, necessities and mother of urgency all right, you get urgent when you have necessity.

Dre Baldwin: 9:02

So I start following his little experiment and I created a little training program for basketball players, because I already had an audience of ball players. I knew that I could help them by showing them how to practice. So why don't I make a product out of showing people how to practice? Okay, so I created two products four dollars and ninety nine cents apiece one for your money or one for shooting and I put them on this little one-page website on a free hosting platform. I was just following Tim's format, his formula, and I went to Google AdWords and I bought five dollars worth of ads for like whatever keyword basketball training or basketball practicing, something like that and Tim said run ads and just send the traffic to your one-page website and then have your product, whatever is called, have a little description of the product and then put a button that says buy this product for and puts your price. So I had that by this product for four dollars and ninety nine cents. When people click on the button, it takes them to another page that says this product is still under construction, but if you want it, just put your email address in and when it's ready will email you.

Dre Baldwin: 10:04

And Tim said if you get people coming from Google, again they don't know you. So there's not your grandma doing it to be nice. Yeah, people coming from Google who put their email address in. That means you have a viable product, go make it and sell it. So it's a those people there's, those are your customers right there. Yeah, and I did this and people were putting their email

Dre Baldwin: 10:22

I want to give a disclaimer here for those who are listening to this in 2024 you can't do this with five dollars. Today you probably need 50. All right, but back then you go, five dollars, you probably need 500. If it's basketball, it's a very competitive keyword. But anyway, I did this and people start putting your email addresses in and, mind you, I still had an audience online. I didn't tell them about this yet because those were my warm audience. You had to deal with a cold audience. So I made the product, put a video up on YouTube, say, hey, I have, this new product is over here at this website.

Dre Baldwin: 10:50

People started buying it immediately the first day I made sales and I remember when I my little Blackberry at the time, the little light blinked and said congratulations, you made a sale for four dollars and 99 cents. When I made that sale, Mackenzie, I said to myself I could do this for the rest of my life, because what I had done was created what we all know now as intellectual property. At the time I was not familiar with that term and it was basically taking an idea, packaging it up, putting a label on it, putting a price on it and exchanging it for money. That's what I just did and I said I got a million ideas, only off one I got a whole bunch of money. So if I can pack as these all up and sell them and make money from it, then I got a business. I got a business opportunity right here in front of me and I knew I couldn't play basketball forever and even if the phone does ring again eventually, your shelf life as an athlete, athletic careers, are very short, so luckily, the phone did ring again.

Dre Baldwin: 11:44

I kept playing till 2015, but, answering your question here, I was an entrepreneur officially as of that day when I made my first four dollar and 99 cents sale, because I created my own product, put it out, sold it and collected the money, and I just made more products, first of all for basketball. At this time and again I told you this is about a three-year span at this time, self-publishing also became ubiquitous. So I started writing books, because I've always been a writer, always been a blogging. Then I started writing books, then I started creating courses. So I had those three things going from 2009 through 2015. So when I stopped playing in 2015, I already had a runway of an audience. I had a framework, I had ideas and I had products. So I already had these things in place when I stopped playing basketball. So it's not like I woke up the next day like, okay, now, what do I do. I already knew what I was gonna do, because I was already doing it.

Mackenzie Kilshaw: 12:35

Yeah, that's an awesome story and just built from there. I mean, now we're almost 10 years later and you've got podcasts, you've got you know so many things 33 books. All of this is built on one item that you didn't even have completed yet and you're already selling it. That's amazing.

Dre Baldwin: 13:19

Oh, thank you.

Mackenzie Kilshaw: 13:19

Yeah, when you got that first blink on your Blackberry, were you like holy crap, like I made it. Or were you like like I can just imagine the excitement of something because you were following what the book told you to do. But when you get that first kind of customer, first sale, must have been really exciting.

Dre Baldwin: 13:40

Well, I didn't say a holy crap, I made it because it was only $4.99, but I was, I was I would say I was satisfied is the word that I would use because I already knew that I had an audience. So this was not. It was not a guess as to whether or not I could sell the product, because I was already posting videos on YouTube for four or five years by that point. So I already knew there were people who wanted exactly what I was selling. So it wasn't a surprise that somebody will buy it. It was satisfaction in that.

Dre Baldwin: 14:12

Okay, Tim laid out this plan, I followed it, I did everything he said and there are people who actually will buy this and they were buying. So I was just satisfied with that. And now the first thing I'm thinking is okay, how can I so enough of these programs to where, if I don't get another phone call to play basketball, it doesn't matter. So that's what I was thinking about. So I'm gonna make enough of these so that I can know, keep my phone turned on, know the bills paid, know the rent paid, etc. That's what I was thinking like do I need to make more of these programs? And answer was probably yes, because once somebody buys one, well, now they need something else to buy. I thought what's the next program? So now I started thinking about all the stuff that I had made on YouTube, all the different things I had taught. I said, alright, how many of these programs can I create? I got a mass produce these because I need to have so many that I could sell the same person 50 programs.

Dre Baldwin: 15:01

Yeah, that's what I was thinking and my mind you, this is not. There's no Chat GPT at this point. I had to manually do this, all right. So that's what I started thinking of how do I do this to where I can make a true full fledged business out of this? And at that time I didn't even know what auto delivery was, which means if somebody bought a digital product from me, I had to email them manually and include attachments of the product. I didn't even know was a such thing as auto delivery, so so that everyone know how far we've come in 15 years. So after about a week of this emailing, every person hit the product. I wrote I thought there has to be a faster way to do this and I found auto delivery. So we fix that up pretty quickly.

Mackenzie Kilshaw: 15:42

Yeah, well, that's the thing, though, when you're stepping into a new business really it was a business for you that you're not sure that's kind of stuff happens. You probably didn't even think about it, and then at first it's oh, I'll just email it, no big deal. But then all of a sudden, you have so much volume coming in that you're just spending your time emailing right emailing attachments. So definitely, automating that was was a great thing for you.

Dre Baldwin: 16:06

Yes.

Mackenzie Kilshaw: 16:08

Your time is better spent not sending emails with attachments, that's for sure.

Dre Baldwin: 16:11

That's right.

Mackenzie Kilshaw: 16:12

So let's talk a little bit more about Work On Your Game and maybe, if you want to speak a little bit first on the transition of, you were very basketball focused. Yes, but, then you became business focused, so do you want to yeah, just talk a little bit about work on your game and, and what is it all about? And how did you make that transition to the business side of things?

Dre Baldwin: 16:39

Sure. So remember, going back in the story was that I got introduced to what turned out to be network marketing when I was in college and they? The first thing is that in those meetings, the speaker would just spend a lot of time just breaking down a lot of people's most of the audience is false beliefs about how do you make money, what are your options when it comes to increasing your income, because everybody was there because they wanted to make more money not everybody, but most of us and the things that he was saying from the stage were not being taught to me in my college lecture halls, and I have a four-year business degree, so why are they not teaching this stuff in schools? I didn't understand it then, but I understand it now, why they weren't teaching it. And then the other thing was he said if you want to build a business, you have to build yourself, so make sure you go by the personal development books. And those are things that I've never heard before, but they made perfect sense. So when I read Kiyosaki, that planted the seed in my mind for being an entrepreneur, I knew I wanted to be an entrepreneur. This was a matter of how and what I was gonna do so.

Dre Baldwin: 17:39

The thing about the programs that I was selling those basketball programs was I was not running ads. I didn't know how to run ads. I only did the Google ad words thing, based on what Tim said, but I didn't keep running ads. I only did that for the experiment and the only marketing I would do to sell my programs was just put more videos on social media. That's how I was selling my programs just put a video on social media, put a link to the website and people are buying them and and then YouTube at some point changed their algorithm that to stop people like me from using them as a resource.

Dre Baldwin: 18:07

Yeah, the thing is, as I kept doing things business wise and the audience that I had could see that I was doing business things, even though it was using basketball as the vehicle, a lot of them started to say, wow, I see, I see you're doing your like your business things right and I started doing more. I was doing brand deals with a lot of big companies at that time based on my influence in the basketball space. But at the same time, I could see the writing on the wall like I wasn't gonna play basketball forever and only thing that was making me popular and helping those programs sell was that I was putting out Basketball videos every day. Well, what happens when I stop putting out basketball videos every day? So I was thinking about that already.

Dre Baldwin: 18:45

So that's why, when I noticed that there was an audience of people who were not basketball players, who liked my stuff, I said why don't I find a way to serve them as well? Because I also understood that my audience when I first started Mackenzie were 13 to mostly 13 to 21 year old males and they're trying to play basketball, hopefully for a living. And one thing you have to understand about that audience is that they're trying to play basketball for a living, which means they don't have any money, which means not much you can sell to them. I don't know if you can sell to people who don't have money. So five dollars was about the ceiling and not the ceiling, but you get my point. I couldn't go high ticket selling to these people.

Mackenzie Kilshaw: 19:23

No, it's like $200, Right yeah right.

Dre Baldwin: 19:26

I wasn't thinking high ticket at the time, didn't even know what that meant, but I understood that there was a limit to this and I would have to sell a bulk of products in order to make the kind of money that I wanted or needed to make. So as people who were not athletes started coming into my world, I realized, okay, there's a whole other opportunity here. So now, this wasn't something that I just magically came up with. So about 2014, I knew I wanted to. I was about to get out of basketball play till 2015. I went to a Toast Masters meeting and in the speech that I gave I just said hey, I'm getting out of basketball, I want to get into. Next thing I was gonna do was professional speaking. The reason why this was my idea was because around 2010, the players again they were asking questions about my mindset. From just watching my videos and knowing my background, I started doing these videos called the weekly motivation, and the weekly motivation was this a little two to five minute selfie video where I would just talk about some mindset principle, that just something that I knew, something that I thought was just common sense to most people. I realized very quickly that it wasn't common sense. It wasn't the common knowledge, and I would just talk about things like discipline and confidence and mental toughness and personal initiative, and I was using basketball kind of as a canvas, but it wasn't about basketball. So people who didn't play basketball started seeing those videos and that's when they started reaching out and saying, Dre, I don't even play basketball, but that stuff you're saying about mindset applies to me the way it applies to others. That's what told me that there was an audience outside of the sports room. So in 2014, when I had went to this, toast masters said I'm about to get out of basketball.

Dre Baldwin: 21:01

There was another guy in the audience who had played in the NFL, and it was only about 10 people in the room. So this is just complete irony. Yeah, he had played in the NFL. I knew his name, but I didn't know his face because football players wear helmets, so I didn't know what he looked like. But when he told me his name, I knew who he was. Yeah, he said well, look, I'm about to retire from football and I am about to go to this conference where all the people do their professional speakers and and what it was was a National Speakers Association conference. I didn't know that at the time. But he said I'm about to go to this conference, I want to find out what I need to know about the speaking business and anybody I meet, I'll just pass their info to you. I said, alright, I appreciate it.

Dre Baldwin: 21:38

He meant well, he gave me an info of one person and she was already a full-time speaker. She was author, she was in the thought leadership, she was coaching, consulting, basically everything that I wanted to do she was already doing. And when we connected I called her and when we connected she said well, look, I will help you learn the ins and outs of the speaking business if you help me understand how to get my name known on the internet, because she wasn't very known on the internet but I was known on the internet, so I'll help you with this if you help me with that. And that's exactly what we did. And she taught me to ropes, to the speaking business. So she helped me understand that, this whole thing that you have, you got something going here. You're an athlete, you have this, these mindset pieces that you talk about. You've already written books, you already have an audience on the internet. So you're already. You're a person who actually does stuff you implement. So I know, if I invest my time into you, you're actually going to do what I tell you. Because she said listen, a hundred people have come to me asking the same thing I want to learn to speak in business. Then I tell them what to do. They do nothing. But you, I see that you're already doing stuff, so I'm betting that you're actually going to do something if I tell you what to do.

Dre Baldwin: 22:43

That's the only reason she decided to meet with me, and and on top of the fact that I could help her with the internet. So, so she started telling me stuff and everything she told me I did it. So she said that you might need to make some cold calls and try to get yourself some some speaking gigs. Speak for free. You need to get some proof that you can actually stand on the stage and speak. And I made cold calls and I did it, and I got on stages and I spoke, and this is how I started to get myself out there and this is how I landed Ted Talks same thing had to just go out there and just pitch myself, and she helped me understand that you need a framework.

Dre Baldwin: 23:13

Okay, so the stuff you're talking about is good, but you got to organize it. You have to organize it in a way that when you call somebody and say, hey, I'm, I'm, I want to speak at your conference, they're gonna say, well, what do you speak about? You need to answer and needs to be concise and it needs to make sense. How does your experience as an athlete help them? And they are a sales company. What do you, what do you had to do with that? And she helped me understand that there's a way to organize that. The framework that became work on your game, so framework that I had to this day, came from that conversation, those conversations, and that's how I started to realize oh, I can transition here. And also when it came to the speaking, the reason was for the speaking was the last part, I'll give it to his answer.

Dre Baldwin: 23:53

Mackenzie was when I started doing the mindset videos, the weekly motivation, the athletes who were watching me and the non athletes will leave comments on the video and say, Dre, you sound like a philosopher, you sound like a college professor, you should be a professional speaker, the way you speak, the way you explain things, because I just had this ability to articulate. You know, I've always had that ability, just communication skill. So that's what planted the seed in my mind okay, if I don't play basketball, what can I do? I can be a professional speaker. And then when I met this woman, she was a professional speaker and she was no charging people 10, 15, 20 thousand dollars for a speech. I said, okay, well, if I can make that kind of money now I'll be a professional speaker. So that's what got me off the four dollar 99 cent programs and on to let me see if I can get into the speaking business that's a really cool story.

Mackenzie Kilshaw: 24:41

I think, too, it shows a lot about, I mean, you. You diversified so much like that. It's a natural progression, but you also had to take the steps to get there and that also I really like the also the power of networking there, because you were literally at a Toastmasters, I think yes, you meet this guy, you connect with him, he connects you to someone, but you do the work and that's that's the glory of having a network of people, that someone can help you and you helped her right.

Mackenzie Kilshaw: 25:14

So that was such a I mean totally changed where you were going, but I think in all the good ways.

Dre Baldwin: 25:20

Absolutely and in your 100% correct, and that the fourth piece of my the working your game framework, as originally created, was personal initiative, which is going and making things happen. You can't sit around just wait for the opportunity. You have to go do stuff. So I just went and did stuff so many different times that Sometimes that's who's serendipitous outcomes that.

Dre Baldwin: 25:41

I could not have planned. I couldn't plan there'd be a. I'm at a meeting with 10 people and an NFL player happens to be there and he happens to be retiring and he happens to want to be a professional speaker. How does that happen? Yeah, that's, that's just blind look, but because I showed up, it occurs.

Mackenzie Kilshaw: 25:55

That's right, yep, you showed up and you took, you started talking to that the NFL player and you start right and you're like, hey, if you go there you share great it's, it's that whole dynamic of being present and you could have went to that meeting and not talk to anyone and went home and None of this might have happened right.

Dre Baldwin: 26:15

Exactly. But that's the reason why I went to the meeting, because someone told me that at Toastmasters you can learn how to be a professional speaker. They were actually wrong. That's not what they do at Toastmasters. No, because I was there and I announced that I wanted to be a professional speaker. Someone heard that and they said well, hey, guess what, I know something.

Mackenzie Kilshaw: 26:31

Yeah, that's awesome. Do you still use basketball a lot in what you talk about?

Dre Baldwin: 26:37

I use sports as a, sometimes I use sports as a frame of reference, but one of the things, Mackenzie, is my superpower is my ability to break things down and put them back together. It's the way I say it, and what I mean by that is, even if you have never picked up a basketball in your life, I can use a basketball example or a basketball metaphor with an audience of people who never played ball and I can explain it in a way that you'll understand it and understand why it connects to what I'm saying, even if you know nothing about basketball. That's my superpower.

Mackenzie Kilshaw: 27:11

Yeah, definitely a talent. Well, and, as you said, you've always enjoyed writing. Clearly you've got great communication skills. I think it all goes hand in hand. Plus, I'm assuming you love basketball still and you're not playing anymore, but let's you still talk about a sport that you love and use that as an easy way for people to understand something.

Dre Baldwin: 27:29

Yes, I can use it as a frame of reference, but I don't need to. So I just want to be clear. I don't need to use basketball. I can. We have to have this whole conversation? I had to talk about basketball at all. I can still give value. So the material that I put out a lot of times I'm not bringing up sports at all and again, if I do bring up sports, you don't need to be a sports player or even a sports fan to understand why I'm using it. But the bottom line is never about sports, because I don't play sports and, yeah, a business person, I'm an entrepreneur.

Mackenzie Kilshaw: 27:57

Yeah, for sure. It's just an easier way to get your message across. I guess when you use it some, when you talk about something that's relatable for people right, it helps depending on who you're talking to.

Dre Baldwin: 28:09

Now, what you're talking about, who's never played sports? Now it might be harder because they don't get it. They don't know why your brain that up. So if I'm using the right reference, it depends on the reference, what I'm talking about, who I'm talking to.

Mackenzie Kilshaw: 28:21

Okay, I guess this is a great point. Then, really, depending who you're talking to, you're gonna change your message to make sure that it's appropriate for them.

Dre Baldwin: 28:28

Mm-hmm.

Mackenzie Kilshaw: 28:29

Awesome. Okay, let's talk a little bit about discipline and two kind of points here. Why is discipline such an important aspect of success? And also how does discipline create confidence?

Dre Baldwin: 28:45

Well, disciplines an important aspect of success, because it's all about showing up and doing your job on a consistent basis. And if anyone asked me, Dre, what's the number one asset that you've used to get from where you were to where you are, an answer is discipline. Always, that is. The most important assets for me personally, is discipline. One reason is because, as you show up consistently and do your job, it helps build confidence, and most people want confidence. Most people need discipline, but they want confidence. And also, because so few people have discipline, it actually allows you to stand out by the law of contrast. Because so few, so few people have discipline. When you have it, you stand up from the crowd. Because most people don't show up consistently, most people don't follow through, most people are not consistent. So, when it comes to why discipline matters so much, and what was the other half of the question, just how does discipline create confidence?

Mackenzie Kilshaw: 29:38

I think you just kind of said it.

Dre Baldwin: 29:40

Yeah. So this is when this one creates confidence. In that, confidence is defined as your belief in your ability to do something, and that belief comes from the fact that you've actually done it. So confidence about looking into your past. And you look into your past and you see that you've done this thing over and over and over again, that you have afforded your right to be confident. You forward yourself the right to be confident at it because you've done it so many times. So that's how discipline creates confidence.

Dre Baldwin: 30:03

And, again, as I said, most people want confidence, but they need discipline. So a lot of times people shy away from the things that they need, but they go running towards things that they want. The problem is, people go looking for the confidence they want but they don't have it because they haven't laid the ground right, they haven't paid the price right. You didn't. You didn't pay for your membership. You can't use the gym, all right. So there's a metaphor for you right there. So you have to actually do the work, because confidence is literally a membership. It's a membership in that once you become confident, you don't just stay confident. You have to keep doing the things that led to you being confident. And if you stop doing them, then you lose your confidence and that ability. It's like if you stop, how often do you record episodes for the show?

Mackenzie Kilshaw: 30:45

Oh, once or twice a week.

Dre Baldwin: 30:47

Once or twice a week. So if you went three months and didn't record anything and then you try to recording it, you probably a little sloppy when you came back right because you stop paying the price. You lost the skill so it works with. That's how it applies anything. That's the concept of atrophy. You don't use something, you lose it. The ability goes away if you're not using it. So the discipline of you recording once or twice a week makes you sharper and use get better time at the time, at the time, the more you do it and you become more confident in doing the thing because you're doing it so often. But if you stop doing it, then the confidence goes away because you are doing the work.

Dre Baldwin: 31:20

Now the challenge is you know in your mind what it looks like to be able to do it because you've done it so many times. Let's say you go away for six months and you know what it looks like to be able to do it because you've been there. But you can't do it right now because you have not been paying the price. So you have to have the discipline to work yourself back up to that skill level that you were at before to get sharp again. But you got to pay the price. You got to start back at ground zero where you were. You can get there faster because you know the path. Then you did the first time, but you still have to pay your dues the same way than anybody else would I.

Mackenzie Kilshaw: 31:50

Love that and I think discipline is something that, honestly, we don't really talk about enough. But I could not agree with you more. It's so necessary and putting in the time. It doesn't matter what your business is. You have to put in the time right, because if you don't, you can hope and wish that that comes, gonna be what it is, but without the actual work you're never gonna get there.

Dre Baldwin: 32:12

That's right. You got to put in the work in anything and as much as know as an entrepreneur. I talk to people all the time about don't fall into the trap of you know what they call hustle culture or a family, that you have to go to bed late and you got to wake up early and team no sleep and all these things that people say about just hustle, hustle, hustle. Don't fall into that trap. At the same time, hard work still matters. You still had to do the hard work. There's no shortcuts of hard work. Anything you want to be successful at, you have to work hard. The challenge is what are you working hard on? That's the real challenge. Is not that there's a way to shortcut the, the mandate for actually putting in hard work and effort and anything you want to be successful.

Mackenzie Kilshaw: 33:00

Yep, I love that advice and it goes to everything business, but I mean it goes to if you want to be a doctor, you have to go to the seven years of medical school or whatever. To be a doctor you want to be right. All of these, it doesn't matter if you're an entrepreneur or small business owner or another profession. Putting in the work is going to get you there and that's the only way.

Mackenzie Kilshaw: 33:18

I love how you said there's no shortcut to hard work, because that's such a such a great way to phrase it so simply, but it's very true that's right mental toughness, too, is something you talk a lot about, and this might go back to discipline, but do you want to just touch a little bit more on mental toughness and why it's necessary in your business?

Dre Baldwin: 33:41

Sure business life the way we describe mental toughness is your willingness to remain disciplined and confident, despite the fact that being disciplined and confident up to this point has yet to produce a desired result. So, no matter how hard you work, how clear and clean your plans are, how talented you are, how much you believe in yourself, inevitably something's not going to go the way you want it to go. Never be. Something's just not going to work in life. Somebody else may disappoint you. You plan to picnic and is raining outside now. You did all the hard work and things just don't go the way that you expected. This is inevitable. It happens to everyone.

Dre Baldwin: 34:14

Knowing is immune to this mental toughness is your willingness to stick to the plan, stay persistent and stay disciplined and remain confident that your effort will pay off, even though it has yet to pay off.

Dre Baldwin: 34:27

And the reason why mental toughness matters so much, Mackenzie, is because it becomes the great differentiator between the people who succeed and the people who fail. And that many people quit when they haven't gotten the result that they expected, especially if they feel like other people know about it, because people are so afraid of ridicule and criticism that they would rather not try, then try and come up short or especially if they've already tried and came up short once, they don't want to let that happen again. So they rather do nothing, they rather just quit. And mental toughness is your competitive advantage. When you are willing to remain consistent, you're willing to stick to it, you're willing to have the grit and the toughness and want to grind it out, getting through the situations that are less than ideal, so that you can achieve your desired outcome even though you're not getting out, even though things are not going the way you want them to go.

Mackenzie Kilshaw: 35:20

Okay, the last thing I really want to talk about and you kind of talked about it a little bit already but personal initiative and why that's so important. But I think for you, like you said before, when you started with work in your game, you you kind of just went for it.

Dre Baldwin: 35:37

That's right. Yeah, personal initiative. And first place I heard this was in the Pomeo Hill and his book thinking girl rich and for the law of success, where that book came from. And he says that if you're going to be successful or I'll say that I say this because I basically took his concept and spread it into my own words is you can't sit around and wait for an opportunity to find you. You have to go, create an opportunity.

Dre Baldwin: 36:01

You have to go and do something so that when I think about my own story, how many times I had to take initiative I had taken this to just go practice basketball and then take initiative to try out for the team when I got cut the first three times. And initiative to go walk on to play in college, and this took to try to play pro when no one was asking me to play pro. I get on the internet when it wasn't even a thing to be. Publishing content on the internet by creating a product, offering it to the world, doing Tim's little experiment to test out and see if this works, to actually sell your $4.99 training program. Talking about mindset in videos because a lot of people are asking about it, realizing that people who didn't play sports wanted it, and not pigeonholing myself in just the sports world. I'm going to that toast master's meeting following what my mentor was telling me to do, all of these things so many times that I had to take initiative in order to be where we are here today. I mean, I don't know if you told your audiences, but how this conversation even happened. All right, there was, there was an initiative taken right. So we, we are always looking to initiate.

Dre Baldwin: 37:06

Initiative comes from the word initiate. Initiate comes on word initial, initial means first. You go, first you have to move first. You can't sit around and wait for someone to offer you the opportunity. Is great when it happens, but is even better when you go create it, because now you know you can create another one. That gives you confidence. All right. So all of these work together the discipline of looking for opportunities and trying to initiate them when they start working. It gives you more confidence that the next one can work and the next one, and the next one. And also you need to have the mental toughness to understand that if you reach out and something doesn't work, that's okay, keep trying. Next one, make the next call. Someone doesn't buy at your last sales presentation, I'm gonna make the next presentation. All right.

Dre Baldwin: 37:48

When I play professional sports, people don't understand how many teams that we reached out to that didn't respond or said no, you only need one. You're gonna pay for one thing at a time, right? So it's not like everybody's gonna say yes to you, even my programs not everybody who saw the programs, both them but we sold enough in them, right? So it's not about everybody saying yes, is about you being willing to take the initiative and because so few people are willing to take an initiative, again it becomes a competitive advantage. So all of these pieces that we talked about discipline, confidence, missile, toughens, personal initiative they're all competitive advantages when you know how to create them and you have them on a consistent basis. Because so few people have them consistently, people can have them every now and then. So few people have them consistently that if you can be consistent in these is separate you from everybody else.

Mackenzie Kilshaw: 38:38

I love that and I did not share how you became a guest. But I'm going to now because I'll be honest with you and I didn't tell you this before I was blown away. I reach out to lots of people, lots people reach out to me and of course I always look to see, because usually you just get a name, maybe a bio attached or check out the website. But you actually sent me a video and it was talking about yourself, in a good way, but why you would be a good guest and why my audience would like to hear this information, and it was fantastic like I was blown away by it. So that was the best ever guest experience that I've had to get a guest on. And but you did that right. I didn't reach out to you. You reach out to me with that video and I watched it. I was like, yeah, he's gotta be on. So thank you for that. That's just just shows what personal press excuse me, personal initiative does. It works, so keep it up for sure.

Mackenzie Kilshaw: 39:39

I'm glad it worked yeah, I'm glad to work to do. You have a most important lesson that you can share with the audience.

Dre Baldwin: 39:46

Yes, we're in a performance and results based business. I tell people that all the time and it applies in the sports world you absolutely have to perform and the result is on a scoreboard.

Dre Baldwin: 39:59

You win or you lose, and you lose too often, you'll be out of a job and in the business world is the same thing. You have to perform in your business and the result is you get to choose the result. But you can count your cash, you can count leads, you can count conversion rate, you can count how many people are watching your show, whatever it is. But there needs to be a clearly defined result that you're after and everyone is no that and the performance is based on producing that result. And if you're not producing the result for too long, you may end up out of a business or you will lose a lot of business. So we're on a performance and results based business. You need to know everyone listening what is the result that you're after and what type of performance is required in order for that result to be achieved on a consistent basis. People don't know that you do a whole lot of work is still not get to your goal, so make sure that's clearly defined.

Mackenzie Kilshaw: 40:48

What is there anything you wish you had known, or maybe wish you could have told yourself in 2014, when you're working on this?

Dre Baldwin: 40:57

Yes, man, so many things. So, going back to when I put my first book out, which I knew about building an email list, because I didn't have a list when I first started, when I put my first book, I probably missed out on fifty thousand email addresses that I could have had on my list had I known about this building that's one. Number two I wish I had known about just going high ticket in terms of selling whatever it is, and I'm selling because it takes the same amount of effort to sell something for twenty grand that it takes to sell it for two hundred dollars. Say, my effort may not be to the same person, but it takes a month effort. So I wish I had known that a lot earlier. So I'll just give you those two.

Mackenzie Kilshaw: 41:32

Those are perfect. Thank you so much. I'm people I know are gonna want to know more about you. Where can they find you? Where's the best place for them to go to learn more?

Dre Baldwin: 41:41

Sure, you can go to all course. You can find me on all the social media platforms, on every single one, usually the name there is just Dre Baldwin or Work On Your Game, different ones with different platforms, but I'm easy to find everything's public. I do have a book that I give off free to people. Can I share that?

Mackenzie Kilshaw: 41:57

Yeah, of course yes.

Dre Baldwin: 41:59

My book, The Third Day, what's ahead right here for those watching on video. This book is all about how you show up and give your best effort when you feel like. That's what discipline is about. So this is one of the main framework. So you explain discipline. So that day when you realize that the thing you signed up for is not one big party, the novelty is worn off, the newness is worn off, but you still have to show up and do your job and is all on you. That is called the third day, and this book is about the decision that you make on that day is not about that day happening, because happens.

Dre Baldwin: 42:28

Everybody is about the decision that you make and your decision is unique and unique to you. So the decision you make determines whether you're gonna be a pro or an amateur. And a professional person does something is a main paid occupation. Only way you can get paid consistently is you have to show up consistently, even when you don't feel like it. That's what this book is about. Is about structuring and systematizing showing up even when you don't feel like showing up. www. t Third day book. com. The book is free. You cover the shipping.

Mackenzie Kilshaw: 42:58

I love that. I think I'll be going on to that site shortly after record this drink. Thank you so much. I really appreciate it. You're a great guest and everybody listening will see you on the next episode. Thanks for listening to Winning. Be sure to subscribe to get all of our new episodes. If you enjoyed this episode and you'd like to help support the podcast, please share it with others, post about on social media and leave a rating and review wherever you listen to it. To catch all of the latest from us, you can follow Winning Podcast on Instagram @winning_ podcast, Facebook @Winning Podcast and on Twitter @winning pod. Winning was created and is produced by me, Mackenzie Kilshaw music, created by Summer Firby, editing by Seth Armstrong. Special thanks to Shauna Foster for voicing our opening and, of course, a huge thank you to this episode's guest. Thanks again for listening and I'll see you on the next episode.