An NBA Pro's Playbook for Entrepreneurial Success | The UnNoticed Entrepreneur

In this episode of The Unnoticed Entrepreneur, host Jim James interviews former NBA player Dre Baldwin (also known as Dray Baldwin). Baldwin recounts his journey from a modest Division‑III basketball background to a decade‑long professional career overseas, and how he leveraged early YouTube videos in 2005 to build a personal brand. He explains the "Work On Your Game" framework—mindset, strategy, systems, and accountability—that underpins his coaching, consulting, and the online Work On Your Game University. Baldwin defines mindset as habitual, subconscious thought patterns and stresses mental conditioning as the key to reshaping those habits. He emphasizes the necessity of clear results and destination‑setting for focus, likening it to a navigation system. The conversation covers his prolific content production: starting with YouTube videos, then self‑publishing 35 books, and creating hundreds of digital products, noting that only about 10% achieved market success. He reflects on product failures, attributing them to oversaturation, poor positioning, and limited marketing. Finally, Baldwin shares three core tactics for "unnoticed" entrepreneurs to attract attention—advertising, collaboration, and free content—while highlighting his aggressive, daily social‑media presence and the importance of cross‑pollination of audiences. The interview concludes with a concise, actionable tip: actively draw attention through these three channels.
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Welcome to this episode of The Unnoticed Entrepreneur. Really a special, special day today because I've got the former NBA basketball star, Dray Baldwin, joining me today. And we're going to talk about performance and results and how, as a professional athlete who played at the very highest level, both in the US but also in 8 other countries, has gone on to impact over 100 million entrepreneurs around the world. He's given TED Talks, he's written an astounding 35 books, and is on the show today to talk to us about really how an entrepreneur can get focused around performance and results. He's also going to give us his one mistake that he's made that we can learn from, and a key tip so that we can be just as successful as In life as we are on the court. Dre Baldwin joining me from Miami. Welcome to the show.
I am pleased to be here, Jim. Thank you for having me on. How are you?
I'm great, thanks. I have to confess, I'd rather be in Miami, I think, than in a fairly damp, uh, February here in the UK.
But it's pretty nice here, mate.
You've got the sunshine coming in, but I've got you coming into the studio, so I'm very blessed. Dre, first of all, tell us your backstory and then we're going to talk about how you transitioned from being a pro basketball player into being a prolific entrepreneur and author.
Sure. I come from the city of Philadelphia. Now, as you said, based in Miami. Always played sports growing up. Got into basketball as maybe the last sport that I tried, decided to stick with it. Wasn't very good when I started. I only played one year of scholastic high school ball. Walked on and played Division III college ball, which is the 3rd lowest tier of college basketball. Hustled my way into playing pro basketball, which started that career that you mentioned, spanned almost a decade. At that same time, I started publishing to this brand new website called YouTube. And, that's where I started to build an audience of people just knowing me, but mostly just athletes. About halfway through my career around 2009, 2010, I started my career in 2005, the players who were watching me started asking questions about mindset. And, that's where I started to lay the foundation for what became—
Yeah.
what we're going to talk about today, the Work On Your Game framework, because not only did the players appreciate the mindset pieces but also people who didn't play sports, they appreciated that stuff about mindset. And, that's how I knew, okay, here's an audience that I can serve if I decide to step outside of the realm of sports, which I knew I wanted to do from the very beginning. So, when I stopped playing in 2015, that's what I jumped into doing full-time. So, these days, we work with high-level professionals and entrepreneurs, people who are just ambitious and urgent about being in the top 2% of what they do, the same way a pro athlete is in that top 2%. I work with professionals now who are either already there or want to be there, and that's what we help people do to this day. So that is what Work On Your Game is all about.
Thank you for that, Dre. So the top 2%, how difficult is it for people like me to get into the top 2%? Do you, do you kind of have to start in the top 5% to get to the top 2%? Or can people really learn that mindset? What they have to do in order to get into that top echelon?
Good question. And no, you don't have to start at a certain place because even myself, I became a professional athlete even though my start was very humble, very humble beginnings from where I started as an athlete. So it's just a matter of, yes, there does need to be some— you got to have some clay to work with. You got to have some material to work with. But at the same time, it's mostly just about you having the right mindset, Applying the right strategy, having the right working systems, and then the accountability to make sure that everything and everyone is and are doing their jobs. That's really the key to getting into that top level. And of course, the key to staying there.
Trey, mindset is used as a term, frankly, quite a lot by quite a lot of people.
That's right.
Can we get your definition of mindset? Sure.
Well, the definition is the way that your mind is set to be used. That's really what mindset is about. It's about your consistent and habitual ways of thinking, your mind, your thought patterns, your ideas, your beliefs, and your attitudes and the way that they are set, meaning they're happening over and over and over again habitually and unconsciously. That's what mindset is.
Okay. And so if someone's got, let's say, an underperforming mindset and they want to be in that top 2%, in your experience of working with over 100 million now entrepreneurs, or rather influencing over 100 million, and you've got tens of thousands that you've worked with and coached, Yeah, 100 million would be a lot of people to work with. Yeah, it would be a lot of people. You've influenced all of your videos and your 35 books. Yeah, but it's tens of thousands of people you've coached.
Yeah.
What, what would you say to these people? What do you say to them that gets them into that mindset? What if there's a pivotal moment or a pivotal phrase? Is there something that you could share that really helps people to, to get to the other side?
Well, if there was a phrase that I could do that with, I'll charge a lot of money for it. But, what it actually is, Jim, is a matter of conditioning. It's a matter of changing your habits because if all human beings, most of what we do, think, and say are habit-based, meaning we are not even consciously aware that we're doing it or thinking it. And, that controls about 85% of our behaviors mentally and verbally and thoughtfully. So, What we need to change are the underlying habits, and that's done through the process of conditioning. And mental conditioning works the same way as physical conditioning in that you take a certain strategy of behaviors and you do them on a consistent basis on purpose, consciously, to the point that your subconscious mind realizes what you're doing. It takes over the task, and then it starts doing it on its own without you having to think about it. The same way that if you tied your shoes this morning, you did it without thinking about it because you've done it so many times that the subconscious mind now takes over the task and you don't have to think about it anymore. That's the way you change your mindset, through subconscious programming, or what we call mental conditioning.
Dre, was this something that you always had, or is it something that you learned along the way? Because it sounds as though you, you know, have, have acquired a great deal of insight. I'm just interested in whether you had this sort of— that's how you got onto the court, or you learned it on the court or afterwards.
Well, it did not come from the court. I wish I had it when I was a little bit earlier because I would probably would have been, would have been a better player. So, it was absolutely not something I was born with. This is something that I developed over time. But, as far as that word that you use there, insight, that is my superpower. That is my most valuable skill when it comes to what I do these days is my ability to kind of see inside of things, break things down, and put them back together in a way that makes it easy for anyone to understand. That's the most valuable thing that I bring to the table. And so, I appreciate the compliment there. And, for me, when it comes to the mindset piece or anything that we're going to talk about here in this conversation, this is all stuff that I learned, applied, developed, and then, of course, mix it in with my own mental wiring, the way that I think and the way that I communicate and the things that I've experienced. And then, I can package it up and put it out there in my own way. So, that's how it came to be.
So, Dre, That's essentially a very positive message, isn't it? Because it doesn't matter where someone comes from, or even frankly where they are today, with the right mindset and the right approach and self-discipline, I'm sure you can move into that top 5% of whatever dedicated field you want. You mentioned performance, but you've also mentioned results. What role do results or the definition of results play in attaining that focus?
They're huge. They're actually one of the most important pieces you need because what are you going to focus on if you don't know where you're going, right? So, it's like if you're driving somewhere, you turn on the navigation, the first thing navigation wants to know is where are we going? Where do you want to go? What's the destination? So, if you don't have a clear destination, then there is nothing to focus on. So, The destination is required for focus. With no destination or no target, then focus is impossible. So, we have to know what we're trying to do, what we're trying to get done, whether that be in the short term or the long term. That is the result. And when you're clear on the result, then you can decide on what to focus on, at least in the moment or again for the long term.
Dre, that's wonderful. And now, you've got the Work On Your Game University and you've published 35 books. Let's just talk about what's the university doing, and then I'd love to know really how you've been building the brand for Dray Baldwin, because you've really gone from the court, uh, to the TED Talk stage and into boardrooms. So that's a fantastic trajectory. So tell us first of all about the university that you've created.
Sure. So, the university is where we do all of our high-level coaching, consulting. That's where our speaking, our programs, our courses, that's basically where all our focus is right now inside the university. So, that's where people get their education, their Work On Your Game education, I guess we can call it, is where that happens there. So, anyone who's being coached by us, anyone who comes to us through any form of consulting, it's all happening inside of Work On Your Game University. based on our 4-part framework of mindset, strategy, systems, and accountability. And the goals there, the results are about your highest level of performance done consistently. And of course, the goal is to help you bring in more money in your business because we're working with entrepreneurs and an entrepreneur's number one mandate is increasing value for shareholders.
Yeah, absolutely it is. So, you've got the university and is that a physical place that people need to go to or is it online or a hybrid?
Hey, maybe one day we'll build a campus, but right now it's online.
Okay. Yeah, I'm sure the UK would love to have a campus. It sounds like a fantastic approach too.
And what we need—
yeah, what we need too really is a mindset, not just academic frameworks.
That's right.
Can we turn the focus to this kind of amazing and frankly prolific content production and how you've been building your brand? Tell us which came first. Is it the frameworks or the books or the videos? And what strategy have you taken to produce so much content so consistently over time?
The videos came first and then the books, I would say, was second and the framework was third. So the videos came first because I had, getting out of college again, I played at the Division 3 level, which is a level that doesn't produce pro players. So, to get into pro basketball, I had to take some extra steps. I had to go to this event, Jim, that is called an exposure camp. And, exposure camp is like a job fair but for athletes. And, you pay to go to these events and a bunch of people who all think they're good enough to have a job as a professional athlete all show up and we all basically play basketball for a couple days. And, we're trying to prove to an audience of pro basketball decision-makers, these are agents, scouts, coaches, players.
Yeah.
team owners from around the world. They all come to one place for this. We're all trying to prove that we're good enough to play pro. Hopefully, we can impress someone. So, I went to that event and that was my segue into pro basketball because I played pretty well at that event. And, the footage from that event because this was in 2005 that I went to this exposure camp, the footage was on this thing called a VHS tape. You remember those, Jim?
I'm afraid I do. I'm afraid I do.
Yeah. Alright. So, the Gen Zers listening to this, you can ask your parents or you can Google it. It'll tell you what a VHS tape was. So, The VHS tape was basically YouTube, but a physical version of YouTube. Let's just put it that way. So, I took that video to an audiovisual store. They put it onto a data CD. And that CD, I put into a computer and I uploaded it to this new website called YouTube. And again, this is 2005. That was the year YouTube came out. And I just put the footage up there just for myself because with a VHS tape, you know, you can lose it, you can get wet, you can leave it in the sun, and the footage is gone. So, I just wanted it to be somewhere where I wouldn't lose it. So, that's how I got—
Wow.
into creating— I kind of stumbled into creating content. That wasn't the original idea. I'm just going to make a bunch of videos and get known from video. That wasn't the plan. But when I put the video out, what happened, Jim, is when I went back to YouTube to check on it some months later, because again, who cares about YouTube in 2005? I noticed that there were comments on the video and people were just saying, hey, who are you? Where do you play? How often do you practice? Who taught you? They could tell. They could clearly tell that this random guy who they don't know It was obvious that I could play, but they didn't know who I was. And I was putting video on YouTube and there wasn't anybody else doing it. So, they were— I could tell that they were presuming, hey, maybe I can learn basketball from this random guy because clearly he knows and he's making himself available. So, maybe he can help me. So, these kids were basically crowdsourcing their knowledge from the internet, which is a normal thing to do now. But in 2005, this was not normal. And if you're from my era or any era before that, I grew up in the 1990s. If you didn't know a person, actually physically know them, you couldn't get information from— there was no— you couldn't go on the internet and get information. You had to go to the library or you had to know somebody, right? So now they could go on the computer and get information. So I realized in a very short time there's an opportunity here because number one, I already went to the gym and practiced every day anyway. That was my normal behavior. And this was without a camera, without YouTube. Then I realized, okay, there's an audience of people who want to see what a high-level player does every day in practice. And I had the ability to do it. And I also know how to, I know how to break down and explain things. Again, you mentioned insight earlier. I know how to do that. So eventually I got the, I got the idea, hey, maybe I can start doing this on purpose and doing it strategically, putting video out. Now it took a few years, Jim. So this is not like some overnight thing. I didn't wake up the next day with this bright idea. So 2005, I put the first video out and from 2005 through about 2000, I would just put out videos sporadically, maybe once a month, every few weeks, whenever I felt like it and got around to it. In 2009, what happened here is, first of all, YouTube was purchased by Google, and Google immediately began to monetize the website, which meant anyone who was publishing content can now make money from publishing content. That wasn't a thing before that. And number 2, I found myself a free agent in sports, so I didn't have any contract offers coming in. And I wanted to make sure I had a secure way of continuously making money. And it wasn't going to— it wasn't happening from basketball, at least at that moment. So that's when I started really focusing on, okay, I'm going to put out a video every day. I'm going to start writing articles on my website all the time. So I started doing this on purpose and doing it much more intentionally. And that's when— this is also the same time that social media started to become ubiquitous. Everybody started using it. So for that period, One more thing. I also started creating my own products. I started creating training programs for basketball players, all in the same timeframe. So that's when all the brand and all that stuff began. So that was the video. You want me to talk about the books and the frameworks or?
Yeah. I mean, what a wonderful story. And as you say, I think also just to point out that one, that you were doing this on purpose, but secondly, that it took time, that you know, you can do it on purpose, but you still need time for it to accumulate and for people to find you and to subscribe. It's really, really isn't such a thing as an overnight success story. So, but then let's talk about how you then move into books, because many people get comfortable in one medium and they stay there.
Yeah.
But you've gone on not to just publish, you know, one book, but 35. So Tell us how you've done that. It's an amazing accomplishment. Yeah.
Well, yeah, it seems— it sounds like it when you say it that way. It doesn't seem like it when I think about it because I was there for every one of them. But, when it comes to the books, I had always been writing. So, I've always been a big reader and a big writer. So, before I even got that video on YouTube in 2005, I was actually blogging first. I had a blog before I had a YouTube channel. Now, the blog didn't take off. I didn't get a bunch of fans from blogging. I did from YouTube. But since I was always a writer around that same period, maybe 2009 through 2011, this is when all this stuff was happening. Self-publishing became ubiquitous. And I realized or I found out that you could write a book and put it out and you didn't have to go through a gatekeeper in order to write your book. So, that's when I started writing even more and I wrote my first book. It's the only book of mine that's a complete just narrative book. It's called By a Game. And it was really just for my basketball audience because all I was talking about was just my basketball story, my upbringing in basketball up through my college years. And then I started writing more books on mindset. And then I wrote some books about how to play basketball professionally overseas because a lot of players were asking about that. How do I play overseas if I want to? Because the industry doesn't have a ton of information. So I started writing books about that. And then anytime I just came up with a solid enough idea that had enough meat on the bones, so to speak, then I'll write another book about it. And that's how I really got into the writing. And the good thing about the self-publishing is that you didn't have to go through a gatekeeper or be approved though by anybody in order to get your book out and you could do it extremely quickly.
And so from a practical point of view, were you writing those, typing those out yourself, or did you get some DuVic voice and then have some people help you? To type it out?
Well, first of all, nobody helped me. Every word that comes out of Work on Your Game is written by me, always will be.
Fantastic.
And secondly, the voice-to-text thing, I don't even think it was that, uh, big of a thing at that time. I don't think it really became a thing until maybe— I know when I wrote my book Work on Your Game, which came out in 2019, by that time voice-to-text was more of a thing because I remember writing certain portions of that through voice-to-text. But everything before that, because Work on Your Game was probably book number, maybe number 20. So about the first half or 60% of my books were all just typing them, typing with my fingers. I like to write on my phone. I can write on the phone very fast.
Wow. Okay. Well, that's even more inspirational. Dre, you've now built this amazing business. And as you say, in the old days when you started, every learning institution was in a physical place, and now you've got an online university. That's how much it's all moved in 20 years.
That's right.
It's— it seems like almost as of a textbook case of how to build a brand through just sheer hard work, but also a great deal of inspiration and passion. If there's something that you've done that hasn't worked quite as you might have hoped, what would that be? Is there something that you can share with us as a— as a lesson that we can learn, um, from something you've done that Didn't quite work out? Why would, why would it have not worked out?
Yeah. Every product that we haven't mentioned here didn't work out.
So, so we've all got those.
Yeah. So I've, I've created a ton of products that didn't really, didn't really sell that well. Might not even sold at all. I just would just move on to the next one, next one, next one, trying to find the right, just trying to find that next hit. Because a lot of what I did from, let's just say from 2009, that's when I created my first product, which is a $4.99 training program for basketball players. Those are my first 2 products was one for $0.01 for shooting, $5 apiece. So, from 2009 to 2020, that whole decade-plus period, there was no— I didn't have any formal, um, as far as entrepreneurial business building, marketing, advertising, I didn't have any training on that stuff. I have a business degree from college, but nothing they were teaching then has anything to do with what we're talking about here today. Zero. So, I was just doing it like, okay, I got another idea. Let's put this out. Here's another idea. Let's put this out. Here's another idea. Put it out. There was no big-brained strategy behind this. It would just be put something out. If it works, let's keep pushing it. If it doesn't work, then let's move on to the next one. So, I've created probably in my lifetime, I've probably created 500 different products, things that had a price tag, and I put it out and told people you could buy this. Now, how many of them actually Worked, meaning people were actually actively buying them, I would say 10%, maybe.
Okay.
Right. But everything else didn't work.
Yeah. Okay. So would that be product market fit, do you think?
Um, uh, maybe it might've just been oversaturation. Might've been I didn't do a good job of marketing it, letting people know that it existed. Maybe I didn't position it the right way. Maybe I was just putting out so much that people just missed it because I just gave them too many things. It was like drinking from a fire hose. So they just missed some of it. So it could have been any of those things and any of those products. The good news is, because I understand the concept of positioning, good news is any of those products, I could go grab one, dust it off the shelf, reposition it, talk about it differently, and probably make a sale right now because none of them were time sensitive. So when I come up with some, and I still feel like I'm relatively new in the business game. So as I learn more and I have more resources and more, maybe more hands on deck to do things, I could get every product I've ever created and market it and advertise it and position it better. And maybe we can make those products sell. So I'm not going to say any of them is dead because who knows, they might come back.
Yeah, they're just in the archive, aren't they? Really? For, for getting back out into the market.
Right.
Trey Baldwin.
My son.
So yeah, well, that's right. You've got a young son there. So it's all in the IP of Dre Baldwin.
That's right.
If there's a number one tip that you'd give to an unnoticed entrepreneur who's listening as I am to your story and just being frankly inspired and amazed, what would be your one, your number one tip to the unnoticed entrepreneur?
If their challenge is that they're unnoticed, if that's what they're calling themselves, Jim, then I would say the number one tip is you need to figure out some ways to draw attention to yourself. And when it comes to marketing, online, there are basically 3 ways to draw attention. May I share those 3 ways?
Please do. Yes, absolutely.
Okay. So, number 1 is advertising. And this is not in any particular order. Advertising is just the fastest. It is also the costliest, but it can produce the results the quickest. So, that's advertising. Second one is through collaboration. And this is what we're doing right now is a collaboration because some of my audience is going to now know you. Some of your audience is now going to know me. So, collaboration is you connect with someone who already has an audience You two do something together, share something together, and now both of your audiences get to kind of cross-pollinate. And the good news about that is that Jim doesn't lose anything, Dre doesn't lose anything because most of our audience members are polygamists anyway. They're not just listening to one person. They buy and read and listen to and watch multiple people. So, number 2 is collaboration. And number 3 is content. Most of us know about content. You put something out for free and let the world see it. The more of it you put out, hopefully, the more attention that you get. Now, content is the slowest to turn over from action to result, but it costs you absolutely nothing, which means you can put out as much of it as you want. And at Work On Your Game, we put out a ton of content. I think we've talked about that a lot right here. So, advertising, collaboration, content, and every entrepreneur, every marketer should be doing a mix of all 3.
Trey Baldwin, and you've Articulated that wonderfully, and also you've demonstrated it brilliantly. Dre Brawley, if people want to find out more about you, where can they go?
Well, of course you got workonyourgameuniversity.com. That's the place where we do all of our coaching, our consulting, our speaking, our programs are all underneath the umbrella of the university. As far as socials, we are on every social media platform, so I'm on all of them. My profiles are public everywhere, so you just look my name up. I am extremely easy to find. I'm hard not to find and we publish on every platform every day. So I'm over-indexing on social media, meaning I post more than any marketer would recommend you post. I post on social media every single day.
Great, Walden. I'm glad that you've taken some time to post and join me and collaborate with me on the Unnoticed Entrepreneur Show today. Thank you so much for joining me.
Thank you for sharing your platform, Jim, and I appreciate the opportunity.
Well, it's really been inspiring. And so For all of us that have thought about mindset as being something other people have, I think what Dre's really shown is that there is a process and that we all have the potential to improve. But we do need to have results in mind before we start with the behavior change, because if you don't have a result, as Dre says, if you don't have the location in the sat nav, the vehicle doesn't know in which direction to travel. It's just the same with our own lives. So He's also shown us how creating content is really a wonderful, wonderful way to share what you think and to bring in an audience and also to serve that audience consistently over time. And that's really why he's built such a wonderful business. And now a man with a mission to build a university to train the next generation. So really an amazing story. So thank you for joining me, Jim James, and our guest today, Dre Baldwin. Dre, thank you so much for joining us from Miami today.
Thanks for having me, Jim.
And it's been wonderful, hasn't it? So if you've enjoyed this as much as I have, do please place a review on the player that you're showing this with and also share it with a fellow unnoticed entrepreneur. Many, many great lessons from today's episode. And until we meet again, I just do encourage you to keep on communicating.
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