Discipline is easy to talk about when things are going well. It matters more when the results have yet to show up.
Dre Baldwin learned that lesson long before becoming an entrepreneur. He spent much of high school trying to make the varsity basketball team, eventually earning a place as a senior but spending the season on the bench. His college career brought another setback when a coaching change left him without a team. Rather than walk away from the sport, Baldwin spent the next two and a half years improving his game and finding ways to get himself in front of the people who could give him an opportunity. He went on to play professional basketball for nine years.
In this conversation, Derrick Kinney speaks with Baldwin about what that experience taught him about discipline, preparation and personal responsibility, and why those lessons became central to the way he approaches business.
Baldwin explains his Work On Your Game framework, including why professionals cannot depend on motivation to keep showing up. He also discusses what he calls “the third day,” the point when the initial enthusiasm surrounding a goal has worn off and the work itself becomes the reason many people stop.
Their conversation moves from the basketball court to entrepreneurship, sales and personal branding, with a particular focus on preparation and consistency. For advisors building businesses of their own, Baldwin’s experience raises a useful question: when progress is slower than expected, what keeps you doing the work?
Key Insights
- Discipline needs something stronger than motivation. Motivation comes and goes. Baldwin argues that professionals need an “anchor,” an outcome strong enough to keep them working when enthusiasm fades or results are slow to arrive.
- Find your scoreboard. Sports provides an objective measure of performance. Business is less straightforward, making it important to identify the measures that show whether the work is actually producing results.
- Keep showing up after the novelty fades. Baldwin calls it “the third day.” Starting something new can generate plenty of energy. The harder test comes later, when the excitement disappears and the work remains.
- Preparation happens before the opportunity. Top performers do much of their work before anyone sees the result. For advisors and business owners, preparation can create an advantage well before an important meeting, prospect conversation or opportunity arrives.
- Build around your strengths. Baldwin encourages business owners to identify their “superpower” rather than imitate how others market themselves. His own advantage is consistency: finding what you do particularly well and continuing to do it.
- Invest in your own development. Baldwin considers himself his favorite investment. Courses, coaches and events may not provide an immediate return, but he sees continued learning as an investment in what he can produce later.
Listen to the Conversation
Transcript
Derrick Kinney
Welcome to the Derrick Kinney Podcast on Modern American Advisor. Each week we revisit one of my most valuable conversations to bring advisors practical ideas to grow their businesses, serve their clients, and make more money to do more good. As a business owner or entrepreneur, rejection is one of those inevitable feelings you’re going to face. Maybe one of your ideas doesn’t pan out the way you want. Or your customers don’t accept a new product or service that you were really excited about.
You’re going to face rejection and adversity, but how you respond to it can be the difference between a thriving and a struggling business. I love bringing expert business minds on this podcast. So today we’re talking about lessons learned from a professional basketball player turned entrepreneur. In just 5 years, Dre Baldwin went from being a high school benchwarmer to signing the first contract of a 9-year professional basketball career. While playing, Dre pioneered new ways of personal branding and entrepreneurship through an ever-growing content publishing empire. His content now has over 73 million views.
Today, Dre is breaking down the discipline, confidence, boldness, and authenticity that every professional athlete needs and how it applies directly to you as a business owner. And he shares how to find your superpower so you stand out and win loyal customers. Plus, Dre reveals the one specific quality it takes to be in the top 1% of athletes, and he reveals the best investment he’s ever made. I think his answer might surprise you. Dre, welcome to the podcast.
Dre Baldwin
Hey Derrick, great to be here with you. Thanks for having me on. Looking forward to this.
Derrick Kinney
Well, I am as well, and I think this’ll really be a timely message for our business owner and entrepreneur listeners. Let’s dig right in. The lessons learned in competing in athletics often translate well to business owners and entrepreneurs. That’s where I wanna start today. You’ve been a talented athlete since you were young. But the story I’m most intrigued with is how you tried and failed to make your high school varsity basketball team for 3 years. Then you finally made the team as a senior, only to sit on the bench the entire season.
Now, to most people, that would feel so defeating. Walk me through how you dealt with that rejection and what kept you striving toward that goal.
Dre Baldwin
Yeah, well, I guess I wasn’t that talented. You know, I didn’t make the team. I barely played in high school. So I was kind of a late bloomer there when it came to sports. But for me, Derrick, I’ve always been a competitive person. I’ve always been a competitor. And I guess what I was doing was fighting against the situation. Not really fighting as a person or a player, but fighting against the situation because I wanted to basically prove myself right.
So when things weren’t really working for me as an athlete, I really It’s just part of my wiring just to tap into how can I fight back against this situation and figure this out and make it work. Because I mean, we’re from the era that was pre-social media, right? So we’re not looking on social media and having all of our feelings and thoughts affirmed and validated no matter how ridiculous they may be.
So the era that I come from and the way that I’m wired, I had to be objective looking at myself like, okay, I might think I’m better than everybody else on the team, but They’re on the team and I’m, I’m here in the bleachers watching the game. So that clearly means there’s something that I need to fix about myself. I need to fix something about my game. There was nothing wrong with them. There was something I needed to do. I’ve always thought that way, and I built my career and now my business around that framework.
What do I need to do and take full ownership of my situation so that I can get things to where I want them to be? And I’m not, you know, putting it, I’m not putting the onus on anyone other than myself.
Derrick Kinney
Well, that’s so well said because as you said, so many people count on social media or others for validation.
Dre Baldwin
Right.
Derrick Kinney
And there’s not a whole lot of introspection that occurs. So what makes you stay disciplined to keep evaluating yourself? And as you said, taking sole responsibility for what happens to you?
Dre Baldwin
Because we’re in a performance and results-based business, Derrick. I mean, this whole thing, this whole game, whether we’re talking about the business world, the sports world, or anything in between, you get rewarded based on your performance and the results of that performance, period. Not based on your stories. People may be interested in your story after you prove you can perform and produce results, but you don’t get paid for the story. You get paid for the result. The result is what people are after.
Because I’ve always been focused on the results and coming from the sports world, the great thing about sports, Derrick, is that we have a scoreboard, right? And it’s black and white. The scoreboard tells no lies. And the scoreboard tells you objectively what the deal is. If you walk into a room and there’s a game on TV and you didn’t know there was a game happening, what’s the first thing you want to know? What’s the score?
Derrick Kinney
The score.
Dre Baldwin
All right. So who’s winning? All right. Who’s winning? Who’s losing? How much time is left? So you can gauge if the other team has a chance here. And that’s the great thing about sports is that that scoreboard is black and white and it always tells the truth. Whereas in every other area of life, you have all these other variables and different ways of measuring, but in sports, you can’t lie and you can’t hide.
And it’s, it’s really clear. So that’s the great thing about coming from sports and then translating it over to business is the kind of people that I work with are people who wanna be dealt with in the exact same way. Let’s look at things objectively as they are, because we’re looking at the scoreboard here. It’s not my opinion, it’s not your opinion. It’s what does the scoreboard say? Let’s figure out what our scoreboards are and we’re gonna base everything off of that.
Derrick Kinney
Yeah. Like you said, you know, feelings tell part of the story, but facts reveal the real truth. So let’s go back then. So you walk on to play basketball in college at a Division III school.
Dre Baldwin
Yeah.
Derrick Kinney
Then you finish your college years not even on the basketball team due to a coaching change, which left you in the cold. So for most athletes, that would be the end of the line, but not you. You chose a different path to keep playing ball. Tell me about that.
Dre Baldwin
Yes, I was literally out in the cold because I was in Altoona, Pennsylvania. It’s pretty cold there in the wintertime.
Derrick Kinney
Literally.
Dre Baldwin
That was the day I was out of the basketball program. So for me, the first thing I did, I remember walking out of the gym that day. I can still see it. The first thing I started doing was reconstructing in my mind because I’ve always been someone who visualizes how I am going to deal with this situation and how can I, even when things change underneath my feet, the first thing I’m thinking is, okay, how can I come up with a new strategy here based on this changing situation?
And the first thing I started thinking was, okay, what am I going to do now? So my first idea was I was going to see if I could go to a different school and play the rest of my career there. When that didn’t work out, next thing I’m thinking is, okay, how can I prove that I’m better than these players who are still on the team and that this coach made a mistake?
And since my college career was going to be over, the only next level was the professionals. So my next thing was, okay, how do I get to the pro level? And it took me – it was 2 and a half years from my last college game to my first pro game. So that was a long time, even though I was still pretty young at that time. It was a long time to not have anything going on as far as being on a team.
So my whole mindset during that period was, let me just keep working on my game, develop my skills, because I knew I needed to get better to be a professional-level player. Because at the time, I was just playing college. I also had to figure out how to get myself seen, heard, and known by the people who could actually help me make a career happen? because again, at the level that I was playing at, nobody was checking for me to go and play in the pros.
But the level that I was at, we didn’t produce pro players at the school that I went to. So I had to figure out how to get myself seen by the people who are actually making it happen in a completely different space? So I had to really tap into my marketing and sales skills and learn how to sell myself.
And that’s really what I learned to do between that time that school ended and my pro career started. And luckily those skills actually helped translate very well, very handsomely into what I do as a business person now.
Derrick Kinney
So let’s talk about some of the mental lessons You learned from facing athletic adversity because that really shaped you, as you said, into the business owner you are today.
Dre Baldwin
Right.
Derrick Kinney
What came out of that, you have said, is a framework that you call Work On Your Game. Explain that framework to me and how business owners can apply that.
Dre Baldwin
Sure. So it’s a 4-part framework that covers, first of all, the discipline to show up every single day to do the work. Secondly, the confidence to put yourself out there boldly and authentically. Third, the mental toughness to continue showing up, doing the work, putting yourself out there, even when the success you’ve expected to achieve has yet to be achieved.
And then lastly, the personal initiative to take all of that stuff and basically turn that potential energy into kinetic energy and go make things happen instead of waiting for things to happen. And the way it translates for business is, first of all, the discipline of showing up every day to do the work.
Now, we all understand whether you’re starting a business, working at a job, studying, or competing as an athlete, is that there are gonna be long days, there are gonna be hard days, there are gonna be times when you don’t feel like being at work, you don’t feel like being at the office, you don’t feel like practicing, and you’re on a sports team. Even pro athletes have days they don’t feel like being at work. It’s how do you show up and do you deliver on those days when the energy is not quite there.
Because a professional must show up. An amateur has an option of not showing up. They have the option of not giving their best effort ’cause they’re not getting paid by definition. But a professional, since you’re getting paid, as soon as you accept that paycheck or that direct deposit, whatever it is, you gotta show up and do a job even when you don’t feel like doing that job.
And that’s what separates the pros from the amateurs. So that’s the discipline part.
Derrick Kinney
One of the things that I was looking at your website, the discipline piece is something that really captured my attention because I think discipline is lacking for so many people. I mean, there are days, as you mentioned, I struggle with it as well. And I’m a very high-producing guy.
Dre Baldwin
Right.
Derrick Kinney
So for business owners listening right now that who have goals and, from the outside looking in,, they’re very successful, very focused, very achievement-oriented, but they’re in a slump. What should they say to themselves or do? What small habits or steps do you suggest to get themselves out of that and stay disciplined to get the results they want?
Dre Baldwin
The biggest thing is that they have to have some anchors in their mind.
Derrick Kinney
Anchors.
Dre Baldwin
Yeah. The way I describe the anchor is, There’s a lot of times when people, you know, everybody wants to be disciplined. People understand the concept of it, almost everyone, but most people can’t execute on it. So they think that to solve that problem, they need to get themselves motivated. The challenge with getting motivated is that often motivation is external.
And secondly, you can’t always depend on that external motivation to be around when you need it. And motivation comes and goes. And I like to tell people motivation’s for amateurs. Motivation is what you give to some eighth graders. But for us professionals, us adults, we have to have something stronger than motivation and something more consistent and dependable than motivation.
That’s the anchor. The anchor is what is the outcome or outcomes, plural, that you want that has a strong enough pull on you that it will move you to be disciplined even when you don’t feel like being disciplined. And that’s the thing that kind of pulls you through what I call the third day, pulls you through those moments when you don’t really feel like being at work and when things are not really working. You made a bunch of calls, nobody’s answering you. Made a bunch of offers, nobody’s buying. How do you keep yourself moving in those moments?
And that’s really what separates those who make it and those from those who don’t. What separates the real pros from the pretend pros and the amateurs is the anchor that’s gonna move you to show up to work tomorrow when you just had 5 terrible days in a row? Do you show up on that next day?
Now, a lot of people don’t. What separates the winners from the losers is whether you show up, even if things aren’t going the way you want them to go.
Derrick Kinney
And to your point, would you agree that not every day is going to be a great day? Sometimes just doing the work and not even feeling like you did a good job, but it’s going to prepare you better for the next day.
Dre Baldwin
Yeah, I actually have one of those days myself today. I’m not at work, but physically I like to run outside. So I like to run 10Ks and stuff like that. I’ve run a couple marathons, but 10K is my nice zone.
Derrick Kinney
Okay.
Dre Baldwin
And, but now in the summertime, I’m in Miami. So it’s humid as ever out here. It’s 83- something degrees at 4 in the morning. And the humidity is like you’re drinking water every time you breathe. And you’re running, and it’s a challenge to run here in the summertime. But all the races are in the fall and the spring when the humidity is lower.
So I know that pushing myself through not so great runs in the summer, by the time I get to the fall and the humidity goes away, it’s almost effortless to get out there and run. So I know this is the challenging time that makes the runs in the less challenging times a lot easier.
So I know today’s run was not my best, but I know that pushing through a run like this, by October, this will be so easy for me. The same distance, but with a lot less challenge to my lungs.
Derrick Kinney
So what you’ve done, Dre, is you’ve really reframed what someone might say is, boy, I’m really not doing well, or what’s wrong with me?
Dre Baldwin
Exactly.
Derrick Kinney
Why aren’t I performing well? To, no, this is normal and this is how I should feel because that’s gonna help me down the road. You’ve just restructured. How did you come to that conclusion to reframe that? ‘Cause that’s a very powerful change right there.
Dre Baldwin
Yes, that’s a great observation, Derrick. And because I’m a very analytical person, I’m a super analytical thinker and I’m, I’m the type of person who I’ve always been able to, as I said, look at myself objectively and not just try to look at everything, even that I do, with rose-colored glasses. And I look at this run that I went through today, and this was not, definitely not my best.
And my energy wasn’t as great as it has been in the times when I’ve won races, at least in my age group. And I had to look at that and understand, all right, let me not just beat myself up and say, okay, I’m just terrible. I know I didn’t get that much worse. But I understand the circumstances, right? The circumstances around it.
And I know, ’cause I’ve done this before, right? Summer comes every year, right? It’s a cycle. Spring, summer, fall, winter.
Derrick Kinney
That’s right.
Dre Baldwin
So I know this happens every year the exact same way. And when the weather gets crispy out here, it’s so easy to run. It’s almost like you’re not trying. So I have to put that in the right frame because what happens with a lot of people in a similar situation, it doesn’t have to be physically, but they have these days where things are not working and they’re like, man, they start looking at themselves and beating themselves up. Like, something’s wrong with me.
Something’s wrong with my process. Maybe I should quit. Maybe I don’t belong here. Everybody else is better than me. And you start beating yourself up. Then the subconscious mind is listening to all of that. And the subconscious mind controls 85% of what you think. It’s not your conscious thoughts, it’s your subconscious thoughts. And especially when they’re emotionalized, they get in there even faster and deeper.
Derrick Kinney
Oh.
Dre Baldwin
So you have to be very careful about your self-talk and your self-conversation. So I always make sure that I frame it, even if I didn’t have a great day, let’s say I didn’t sleep well the night before, or I went to bed too late, or I ate some pizza. Like, that’s my fault that I didn’t perform the way that I was supposed to.
And I can own that too. But it’s just making sure that we can look at ourselves objectively, as objective as a human being can be. ‘Cause no human is completely objective, but try to be as objective as we can be about ourselves and with others. Because I mean, that’s literally what I do for a living, so I have to do it. Yeah. Yeah.
Derrick Kinney
You wanna practice what you preach, but it’s, it’s nice to talk with people who admit I struggle with this as well. You know, so many people looking on the outside see somebody like you, Durie, and they say, man, this guy’s super successful, got it all together, no problems. But then they hear you pull back the curtain and say, look, I struggled with this today. I just found a way to get through it.
And I, that’s why it can help you as well. So thank you for being so vulnerable on that. I really appreciate that.
Dre Baldwin
Thank you.
Derrick Kinney
Now you mentioned, uh, in one of your books a principle, and you touched on it briefly a second ago called the third day.
Dre Baldwin
Yeah.
Derrick Kinney
And that really got me thinking about business and how this can apply to entrepreneurs. Talk about that principle and what it means to them.
Dre Baldwin
Sure. So the third day originated from my basketball days when I used to put all these basketball videos on YouTube and the players would always ask me, well, Dre, why is your gym always empty? Because any young basketball player knows you go to the basketball court, everybody’s there. You never get, can get the court to yourself to kind of practice ’cause so many kids on the court.
And I would always be in this empty gym. So they would ask me, well, do you own the gym? Do you rent the gym out? You know, do you go at a time nobody else is there? And the answer was this whole concept of the third day. And I explained to them, if you put a brand new gym out there, the first day everybody’s gonna be out there. The second day, still a lot of people, but not as many.
And by the third day, it is damn near empty. And I don’t mean necessarily that quickly in 3 days, but over time, eventually the newness to the situation, the novelty wears off. People realize that, okay, yeah, this is a nice place, but It’s not funny games. It’s not a party here. You actually, only thing you can do here is work.
Derrick Kinney
Wow.
Dre Baldwin
And eventually people are gonna stop showing up because they don’t wanna do the work. And as long as, and I just continued to show up. So the reason I had a gym, an empty gym to myself all the time when I was making those videos is because I just showed up every day. It’s not, I wasn’t going to any exclusive resort. The gym was $10 a month. There’s a city-owned gym, so anybody can get in there, but just nobody came. I just kept showing up every day.
And that was the third day. And how it applies in business is the exact same way. Because a lot of entrepreneurs, especially these days, because we have the internet and everyone can post their highlight reels and make it look like everything they do is turning to gold, like King Midas.
Derrick Kinney
That’s right.
Dre Baldwin
Right? So as an entrepreneur, if I’m an up-and-coming entrepreneur right now and I go on Instagram and I’m looking at me, I’m looking at you, I’m looking at all these entrepreneurs out there and I’m like, man, everything they do looks so shiny. Their pictures are so crispy. They are doing these events that are into full rooms of paying customers. Man, I just put out my first product and nobody bought it. Uh, I must be a bum. There must be something wrong with me.
Maybe I need to go back to, you know, my full-time job because clearly I’m not good enough for entrepreneurship. And we start comparing ourselves to what we see other people doing. That’s the third day. Or you think you put all this time into your product launch and nobody signs up, or you put all this time into writing your book and nobody wants to read it, or you put this time into launching your podcast and you’re not getting any downloads, or you posted something on Instagram, nobody liked it. You wrote this long caption, nobody read it.
And so you’re looking at yourself And wondering if something may be wrong with you. And it’s in that moment, is that moment right there, is the decision that you make. Am I going to continue to show up to figure this out? Or are you gonna, no, just stop giving full effort, completely quit, and not keep trying in this game because you have indoctrinated yourself and conditioned yourself to believe that something must be wrong with you, your process, your idea, or something along those lines that says you don’t belong here. Or are you gonna keep showing up and doing the job?
That, it actually applies in business much more than sports. ‘Cause at least in sports, we can look at the scoreboard and you at least know exactly where you’re at in sports. You can see the scores.
Derrick Kinney
Right.
Dre Baldwin
In business, you have no idea. And you often don’t even know who your competitors are. At least in sports, I know if I’m on the Knicks, I know we got the Lakers, the Bulls, the Heat. I know who all the opponents are. In business, you have no idea. And so you have to figure these things out.
And if you don’t have the right internal conversation going on and you don’t have the right mental conditioning going on, then it’s gonna be a very rough ride that might not last long. Ooh.
Derrick Kinney
Well said. Well said. Spicy, but well said. You know, as I consult with business owners, I find that they all want to be successful. They all wanna grow their business, but what holds them back from reaching their revenue goals is they don’t know what to do. Now, you say that you can, quote, Prepare to perform like the top 1%. What does it take to be in the top 1%?
And what are some specific examples of people who perform like that?
Dre Baldwin
All right, great question. So first of all, one of the things that the people in the top 1% do is they actually take the time to prepare. And while people like yourself and myself, Derrick, we might think it a normal thing, it is like common sense to go in, quote unquote, common sense. to prepare for a performance. A lot of people don’t prepare. A lot of people show up to situations completely underprepared.
And one of the things I’ll say about professionals versus amateurs is that a professional is always prepared ahead of time for a performance or a job or a deal, whereas amateurs often show up at the moment and hope that they can figure it out as they go along. An example of this is, uh, you familiar with Floyd Mayweather, right? The boxer?
Derrick Kinney
Yes, sure.
Dre Baldwin
Okay. All right. So I was hearing, I was listening to this guy being interviewed. I think it was on Tim Ferriss’s podcast. And he was talking about how ‘Cause he knows Floyd. So he’s at one of the fights to see Floyd fight. And he’s with his wife. And one of Floyd’s people hears that Triple H is in the audience.
So they send for Triple H to come back to the locker room. So they bring Triple H and his wife back to the locker room. He meets Floyd, introduces his wife to Floyd, and they’re cool. They’re just talking a little bit. And Triple H looks up at the – there’s a clock counting down in the locker room. This is a big fight.
And there’s like 30 minutes left. And Triple H is thinking to himself, well, I know what I need to do when I’m getting ready to perform. I want everybody away from me so I can get in my zone. 30 minutes before the performance. So he says, hey, man, we gonna get outta here. He tells Floyd, we gonna leave and go back to our seats.
And Floyd says, nah, man, it’s cool. Just stay here and watch TV with me. And Floyd’s just hanging out watching TV. You couldn’t even tell he was about to fight for this –
Derrick Kinney
Wow.
Dre Baldwin
a $100 million fight. And all right, Triple H is like, all right, okay. So they keep talking, hanging out. He looks up at the clock again. It’s 15 minutes left before he goes out to fight for his championships. And Triple H says, all right, man, we’re really gonna get outta here. because again, Triple H is thinking how he thinks when he’s performing.
And Floyd looks at him and says, man, look, if I’m not ready to win this fight right now, nothing I can do in the next 15 minutes is going to get me ready to win this fight. I’m already ready.
Derrick Kinney
Yes.
Dre Baldwin
And Triple H, he relayed the story, and I don’t even know which fight that was, but we know Floyd’s undefeated. So whichever one it was, he won. He was ready. And the whole point is professionals are always ready for their situation. And whenever you see a professional show up not fully prepared, this is when they get beat. Think of Mike Tyson when he got knocked out by Buster Douglas back in the early ’90s. He wasn’t prepared. He wasn’t mentally prepared. Physically, he had the tools, but he wasn’t mentally prepared.
Michael Jordan, when he came back from baseball in the middle of the season, he was still pretty damn good, but it was that little piece that he didn’t have playing against the other top 1% players in the world. That little piece, they ended up losing. Other pieces they needed on the team as well.
But Michael Jordan wasn’t all the way Michael Jordan. He talked about it himself. And one of the things that Mike said was, during that season when he came back from baseball in the middle of the year, he said, I can still do the great stuff, but I couldn’t do it at the snap of a finger like I used to. I used to be able to just tell myself, all right, I’m taking over and do it.
And he said that year I couldn’t do that anymore. But then he spent that whole summer, the summer of 1995, getting himself back to basketball shape. And then we know what happened. Next 3 years, he won a championship all 3 years in a row.
Derrick Kinney
Yeah.
Dre Baldwin
So it was that preparation. And that’s what separates the pros from the amateurs is that that’s Just the time that they take to do the preparatory work. So then when they get to the performance, it looks easy and everybody’s looking at them like, man, this person is so talented. That’s not talent. That is preparation plus talent.
And that’s what makes greatness.
Derrick Kinney
Dre, let me ask you this and see if you agree or disagree. When you think about professionals preparing, you know, obviously the younger that we are, there’s more talent, athleticism. As athletes get older, they tend to retire and they kind of age themselves out. But would you feel that being a professional is as much preparing, but also understanding how to maximize where you currently are in your current health and athletic situation to maximize your current situation?
Dre Baldwin
Sure. So it’s looking at what tools you have and what resources you have, and then just figuring out what your game is kind of what we say in the sports world. And they call it playing within yourself, right? Knowing your skills. So if you’re not a three-point shooter, don’t try to shoot three-pointers, right? If you’re not athletic like LeBron, don’t try to dunk on everybody.
So it’s knowing what your game is and then maximizing yourself to make the most of that game. And to give you an example, let’s say from the business world here, for the business people listening, you take someone like, one of my favorite audio programs that I listen to over and over is Zig Ziglar, Secrets of Closing the Sale, right? Yeah, Yes, I’ve heard that. He made that, maybe, I don’t know when he made that. I may not have been alive when he made that recording.
But one of the things in there is he’s just going over, here’s all the different ways you can close a sale. When a prospect says this, or they ask this question, or they’re showing this, here’s how you frame it and move the conversation where you want to move it. And I’ve used that stuff to close deals, right? 30 years after he made it.
And that’s part of preparation. That’s what a good salesperson is always making sure they’re ready to close the sale because you’re in the business of selling. You don’t get paid unless you close the deal. And everything in life is a sale. So having yourself prepared with information, being prepared with knowledge, being prepared with insights, being prepared, like knowing your audience, knowing who you’re talking to.
One of the things that you’ve shown right here, a lot of people probably won’t appreciate this as much as they should, Derrick, but I know that you’ve done some research on me because you’re pointing things out that I know I didn’t say to you when we made our connection, but you went and did the work.
That’s preparation. And that It’s a little thing and it’s that slight edge, I guess we can say, that separates over time. There becomes a big gap between you and the people who don’t do that work.
Derrick Kinney
Yeah, it’s interesting. It’s, it’s like that one degree. And if you’re getting better one degree every day, it’s a small change, but focusing on that every day makes a huge difference. Now, this is something I’m real excited about because I wanted to delve in. Dre, you are a content creation machine. And I wanna talk about marketing and attracting your ideal customers. I mean, you produce a heck ton of content as you’re building your brand, and I wanna know what’s the easiest and most effective way for people to brand and market themselves and their business right now?
Dre Baldwin
The easiest and most effective way is figuring out your superpower and pressing on the gas on that superpower. What is that thing gonna be for you? So you noticed, uh, before we even got to this point in the conversation, Derrick, a lot of what we’ve been talking about here is on discipline, consistency, preparation.
Derrick Kinney
Right.
Dre Baldwin
And then you bring up the fact that I’m consistently disciplined in putting out material, right? And so I am living exactly what my strength is. My strength that I have, I feel like I have more than one strength, but if I had to point out one strength that most separates me from most other people is the consistency. is the discipline, is the fact that I show up every day and do my stuff.
So even when people reach out to me and I say, hey, what’s the challenge that you’re dealing with right now? The number one thing I hear all the time is consistency. It’s not because everybody –
Derrick Kinney
Consistency.
Dre Baldwin
Right. It’s not because everybody in the world is challenged with consistency. Maybe they are, maybe they’re not. People usually have more than one problem, right? But when they’re talking to me, they bring up the thing they think I can help with. So that’s why I always hear about consistency and discipline. So if someone’s trying to get themselves out there right now, you really have to figure out what is your superpower? What space can you own? What is your niche? Is it, no, that you’re funny? Is it that you can put stuff out every day?
Is it that you just can go deep in depth? And like, there are some people who can write long, thousand-word articles all the time, and that’s their thing. Then you get somebody like Seth Godin, he writes a 2-paragraph article and he’s branded himself around that, right? Little 2 paragraphs every day in your email.
But that’s his thing. And then you have people who can put out a 30-minute solo episode every day. And then you got people who do an hour-long, a 3-hour livestream every night, and that’s their thing. So you have to figure out what’s the space where you can dominate and people can come to know you for that thing, and then just press the gas on that and use it to your advantage.
Derrick Kinney
So I’m taking copious notes here in the background, Dre. So if you hear me clicking, uh, you’re saying some good stuff. And I really like when you said, what is your superpower? And then press the gas pedal on that. You know, so many business owners and entrepreneurs have this fear. They’ve got this idea, but now they’ve gotta tell the masses about it and they just freak out like, oh my gosh, I’ve gotta be this perfect YouTube star, Instagram hero.
And the bottom line is just put a phone up and start talking.
Dre Baldwin
Smart.
Derrick Kinney
And producing content. I mean, when I began doing some work on this 2 years ago, I was nervous, anxious, worried, but it just gets better and better. And then I realized nobody was really thinking about me as much as I thought they were. And it really humbled me a lot.
Dre Baldwin
Mm-hmm.
Derrick Kinney
You know? So the key is, as you said, is action, consistency, discipline. And with consistency, you get better in terms of the quality. And, you know, we’ve talked about business today, and I think our listeners have taken a lot from the well that we’ve tapped into. And now I like to ask each of our guests like yourself how our listeners can build their wealth.
And so I have 5 fast questions I want to ask you, Dre. First of all, what advice would you give your 18-year-old self about money?
Dre Baldwin
Oh, get financially literate, become financially literate. And go, first of all, figure out what that means and then go to the library, or I guess now it’d be Amazon, but back then it would’ve been the library or the bookstore, and go read some books on financial literacy that are written on your level so that you can actually understand what that means.
Derrick Kinney
Any books that come to mind that you’d recommend to people right now that you like?
Dre Baldwin
Oh yeah, of course. We have to start with Robert Kiyosaki. Rich Dad Poor Dad. That’s where I started. That’s the reason I’m an entrepreneur to this day.
Derrick Kinney
Yeah. Such a good book. Such a good book. What is the biggest financial mistake you’ve ever made?
Dre Baldwin
Hmm. That’s a good question. Nobody’s ever asked me that. The biggest financial mistake that I have ever made is, I’ll give you one. In 2009, I went to a Miami Heat game here in Miami, and there was this, I had, we had these really good tickets to like a preseason game. So I wanted to, when you go to preseason games, all the sales people come around, they try to sell you more tickets.
So the sales guy came and he brought us to better seats, like damn near half-court front row. He’s trying to sell me on the season ticket package. And I’m like, man, this Miami Heat team, this team is okay, but I don’t want that many tickets to see this team. It seems not that good. They only had one good, one great guy was Dwyane Wade at the time.
And the guy said, well, look, you hear about how in the summer of 2010, they’re clearing cap space, you know, LeBron might come play here in Miami. And I looked at the guy, he was crazy. I said, come on, man. LeBron James is not coming to play for the Miami Heat. All right. What am I gonna do with 41 tickets to the Miami Heat games for the next 5 years with this team?
And then LeBron comes here and I knew guys who had season tickets and they didn’t go to any games. They just sold their tickets every night and wow, they made a lot of money off those. So that was my biggest financial mistake, not buying those tickets.
Derrick Kinney
Yeah, I would agree with you on that one.
Dre Baldwin
Yeah.
Derrick Kinney
Flipping the script here. What’s one financial decision you are most proud of?
Dre Baldwin
Well, that’s another good question. One financial decision that I’m most proud of is, man, just understanding the concept of investing in myself and being willing to do things like go to events, sign up for courses, hire coaches, and, you know, put money into, you know, mastermind programs, things like that. Things that many people wouldn’t put their money into because there’s no money immediately coming out.
But it’s building yourself up and building your mind up to the point that you’ll be able to make more money later. It’s just that investment mindset that surprisingly a lot of people just don’t have. They can’t wrap their minds around that. So me being able to learn that, even though I was not taught it as a youth, but being able to learn it later, I would have to say that.
Derrick Kinney
Oh, that’s good. What’s your favorite investment right now?
Dre Baldwin
My favorite investment is myself. That’s my favorite investment right now is investing in myself. So joining programs, I’m in two programs right now. I’m about to join another one this week. So I’m always getting into programs and I’m about to buy the ticket to a couple events. I’m about to spend a couple thousand dollars on that, but I can write all that stuff off.
So that’s how I can justify it emotionally, but I know logically it makes sense anyway. So just myself.
Derrick Kinney
Yeah. And for our audience, so These aren’t events necessarily that you’re speaking at. These are ones that you’re going to –
Dre Baldwin
No, not at all.
Derrick Kinney
To soak in information to keep refining your craft.
Dre Baldwin
That’s right. Mm-hmm.
Derrick Kinney
Yeah.
Dre Baldwin
Yeah. Okay.
Derrick Kinney
And the last question, in my book, I wrote about a concept called The Generosity Purpose, which is a cause that you’re passionate about and supported either individually or with your business. And I’m curious if there is a cause that you care deeply about, and if so, what is that?
Dre Baldwin
No, I don’t have anyone in particular. One thing that I do engage in, Derrick, is I go to this website called Kiva. You familiar with Kiva?
Derrick Kinney
Kiva? Yes, sure. Yeah.
Dre Baldwin
So I go on Kiva and I’ll just search and I’ll try to find a project. I don’t look based on any particular demographics like male, female, where they’re from or anything like that, usually outside of the United States. But I try to find a project that’s close and I can give some money to kind of get them over the hump, or somebody who is at zero and they’ve been around, but nobody’s giving them any money.
So I’ll try to give them some momentum by giving them money. And then whenever they pay it back, I just redonate it out. So I like using a site like Kiva and just keeping that money in rotation at all times. Whatever’s in there, I never take it out.
Derrick Kinney
Yeah. And those are pretty small dollar amounts too. I mean, you’re actually making a big change with very small dollar amounts. Almost anybody can do that.
Dre Baldwin
Exactly. Exactly. You can make a big difference to somebody for someone outside the United States. $50 can be huge for their –
Derrick Kinney
can be huge –
Dre Baldwin
their progress. Right.
Derrick Kinney
That’s great. Well, Dre Baldwin, I have really enjoyed this conversation. I know our listeners have taken a lot out of this. I’ve taken quite a few notes myself. You’ll need to listen to this several times, people. Dre Baldwin, thanks for being on.
Dre Baldwin
Thank you for having me on, Derek. I appreciate the opportunity.
Derrick Kinney
Talking to Dre reminded me of a post I put on Instagram a few days ago. In it, I talked about how many business owners keep thinking, I need to make my product better and better. So they lower prices and focus on adding fancy new features, but they don’t focus on solving a problem. Your product probably doesn’t need more fancy features. As long as you’re solving a problem, you just need more people to know that you exist.
That’s the key difference I want you to hear. Make it about the person whose problem you’re trying to solve. Don’t make it about the product itself. If you do that, you will see your sales increase and grow your business. Thanks for listening to the Derrick Kinney Podcast on Modern American Advisor. Do you want to attract more $3 million to $10 million clients and grow your business? Then check out successforadvisors.com.
That’s successforadvisors.com. And remember, if you want a business that’s booming, focus on the human. We’ll see you next time.
About Dre Baldwin
Dre Baldwin is a former professional basketball player, entrepreneur and creator of Work On Your Game. After spending much of his high school career on the bench, Baldwin went on to play professional basketball for nine years.
During his playing career, he began building an audience through online content, eventually generating more than 73 million views. His work now draws on lessons from professional sports to address discipline, confidence, mental toughness and personal initiative in business and performance.
More from Dre Baldwin
Resources Mentioned
- Work On Your Game — Dre Baldwin
- Rich Dad Poor Dad — Robert Kiyosaki
- Secrets of Closing the Sale — Zig Ziglar
- Kiva
FAQs
Who is Dre Baldwin?
Dre Baldwin is a former professional basketball player and the founder of Work On Your Game. His path into professional basketball was unconventional. He spent much of high school on the bench and later went more than two years without playing for a team before beginning a nine-year professional career. His work today applies lessons from sports to business, performance and entrepreneurship.
What is Dre Baldwin’s Work On Your Game framework?
Work On Your Game centers on four areas: discipline, confidence, mental toughness and personal initiative. For Baldwin, the framework is less about motivation than what happens when motivation is absent: doing the work, putting yourself forward and continuing when the expected result has not arrived.
What is “the third day”?
Baldwin uses “the third day” to describe the point when something is no longer new. The initial excitement has passed, fewer people are showing up and the work remains. He first recognized the pattern through basketball, but sees the same thing in business when a product does not sell, a new podcast attracts few listeners or an idea takes longer than expected to gain traction.
How does Dre Baldwin stay disciplined?
Baldwin points to what he calls an “anchor.” Rather than depending on motivation, which can change from one day to the next, he focuses on the outcome he is working toward. That outcome has to matter enough to keep him moving through the days when the work is difficult or progress is hard to see.
What can business owners learn from professional athletes?
Preparation is one of the clearest lessons Baldwin carries from sports into business. Professionals prepare before the moment of performance. For a business owner or advisor, that might mean knowing the audience, researching a prospect or sharpening a skill well before it is needed.
Continue Listening
This conversation is part of Modern American Advisor’s ongoing Derrick Kinney Podcast series, featuring discussions with industry leaders, entrepreneurs and business strategists on the ideas shaping the future of wealth management.
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- Brian Feroldi — How To Invest Through Market Volatility
- Rich Redmond — Fear, Preparation, and Lasting Success
