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Success Story Podcast

Dre Baldwin – Entrepreneur & Former Pro-Basketball Player | Work On Your (Business) Game

By May 22, 2022January 18th, 2023No Comments

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About The Guest

Dre is a former 9-year pro basketball player who traveled to 8 countries in his career after walking on at an NCAA Division 3 school.

He is now a full-time entrepreneur who has authored 29 books and performed 4 TEDxTalks on Discipline, Confidence, Mental Toughness & Personal Initiative. Dre has over 137,000 subscribers on YouTube, and his daily Work On Your Game podcast has been downloaded over 3 million times.

Talking Points

  • 00:00 — Intro
  • 01:49 — Dre Baldwin’s origin story
  • 11:08 — What are some of the things applicable for high-performing professional athletes vs those for entrepreneurs?
  • 17:56 — What are some thoughts of Dre Baldwin on entrepreneurship?
  • 22:47 — How does Dre Baldwin maintain confidence even when something isn’t going according to plan?
  • 30:26 — How did Dre Baldwin condition himself for mental toughness?
  • 34:50 — How does Dre Baldwin get a person on board who has no time to invest in themselves?
  • 36:54 — What does personal initiative mean according to Dre Baldwin?
  • 40:49 — What is the impact Dre Baldwin wants to leave on the world?
  • 42:58 — Where do people connect with Dre Baldwin?
  • 46:15 — What was the biggest challenge of Dre Baldwin’s career?
  • 46:47 — Who is the mentor of Dre Baldwin?
  • 47:26 — A book or a podcast recommended by Dre Baldwin?
  • 48:45 — What would Dre Baldwin tell his 20-year-old self?
  • 49:11 — What does success mean to Dre Baldwin?

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What is the Success Story Podcast?

On this podcast, you’ll find interviews, Q&A, keynote presentations & conversations on sales, marketing, business, startups, and entrepreneurship.

The podcast is hosted by entrepreneur, business executive, author, educator & speaker, Scott D. Clary.

Scott will discuss some of the lessons he’s learned over his own career, as well as have candid interviews with execs, celebrities, notable figures, and politicians. All who have achieved success through both wins and losses, to learn more about their life, their ideas, and insights.

He sits down with leaders and mentors and unpacks their stories to help pass those lessons on to others through both experiences and tactical strategies for business professionals, entrepreneurs, and everyone in between.


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Machine Generated Transcript


people, confidence, day, sport, play, mindset, athlete, book, mental toughness, podcast, dre baldwin, basketball, scott, conditioning, game, business, point, person, HubSpot, work


Scott D Clary, Dre Baldwin


Scott D Clary  00:00

Welcome to success story, the most useful podcast in the world. I’m your host Scott D. Clary. The success story podcast is part of the HubSpot Podcast Network and the blue wire Podcast Network. The HubSpot Podcast Network has incredible podcasts like my first million. My first million is hosted by Sam Parr and Shawn Peri, they feature famous guests. They discuss how companies made their first million and then some they brainstorm new business ideas based on the hottest trends and opportunities in the marketplace. Here are some of the topics he talked about. If you like any of these, you will love the show three profitable business ideas that you should start in 2020 to drunk business ideas that can make you millions, asking the founder of Grammarly how he built a $13 billion company or Sass companies that anybody can start. If these topics are up your alley, go check out my first million listen to it wherever you listen to your podcast. today. My guest is Dre Baldwin Dre is a former nine year pro basketball player who traveled eight countries in his career after walking on at an NCAA Division Three school. He is now a full time entrepreneur who has authored 29 books and performed four TED talks on discipline, confidence, mental toughness and personal initiative. Dre has over 137,000 subscribers on YouTube. And his daily work on your game podcast has been downloaded over 3 million times. So we spoke about personal initiative we spoke about entrepreneurship we spoke about confidence, mental toughness and fortitude lessons that he’s learned from a life as a professional basketball player, and he’s applied to building businesses. So let’s jump right into it. This is Dre Baldwin, author, speaker, writer, entrepreneur, and former professional athlete


Dre Baldwin  01:50

Alright, so give you a three to five minute version Scott come from the city of Philadelphia. Now live in Miami, Florida. Always play sports growing up so all the normal backyard or where I’m from driveway sports kickball, somebody had no basketball court or portable court in the backyard touch football. Oh, that the first organized sport that I tried was football. Couldn’t my family couldn’t afford football equipment. So I never really got around to the serious part of football, then play some baseball for a few years. And all my neighborhood friends played on the baseball teams, we just all play sports, but I didn’t really have a lot of talent for baseball. I knew my ceiling was mediocrity. So I moved on from baseball to basketball. And I was around age 14. So if you’re just starting a sport at age 14, you’re probably not going to go far in that sport. If you’re trying to go somewhere, let’s talk about no cause you’re gonna want to play pro. So me playing basketball starting at age 14 to try to go anywhere ambitious was kind of far fetched. And even in my high school years trying out for the basketball teams, that it was a my reality was a reflection of that didn’t meet my high school team until I was a senior sat the bench the one year that I was on the team. I score two points per game that anybody who knows basketball knows two points not about. Now maybe if you’re playing I’d always tell people you’re playing soccer or hockey 2.0 Superstar, but in basketball, you’re not even playing. So finishing high school, I knew I wanted to go to college, because I just wanted to get the experience I wanted to get out of my my city, my neighborhood where I’m from. And college was a good excuse to get away and go see another part of the life and other part of the world. But also wanted to play sports. But I did not have any type of I didn’t have any offers. I didn’t have any sports scholarships, no sports coaches were checking for me or anything like that. So wherever I was going to go to school I was going to have to walk on. And for those who don’t know what that means, it means you literally walk in nobody. You didn’t have an appointment. It’s kind of like making a sales call with no appointment done. Yeah, exactly. So I was I was basically cold calling my way into college basketball. And the challenge though, with college is that you have to actually enroll in the school. It’s not like you can pick any school, you have to enroll, then try to make the basketball team. So that’s what I did. I went to a school that is now a Division Three level play college basketball, didn’t set the world on fire, but I did play. But again, I’m playing at Division Three level. Again, for those who don’t know, sports, d3 is the third tier. So when you watch college football championships and all that March Madness as division one, then is Division Two, we were down here in the basement at Division three. So division three athletes usually are not the ones even dreaming about making a pro win and I’m actually doing it. But when I got out of college, I still had this idea, this irrational idea that I was going to become a pro athlete. But again, I had no prospects. So when I got out of school, there’s not like, it’s not like there’s a bunch of basketball agents no beating down my door. No, my family didn’t have to change their number. We weren’t getting too many phone calls from agents, about representing Dre Baldwin to play pro bowl. I wasn’t having scouts come to my games or anything like that. So my first year out of school I had while I had this idea, again, I had no solid prospects in my first year after I graduated, and this is in graduate May of 2004 to give everybody a timeline. I worked at footlocker that was my first job. The first job I got was footlocker, I was an assistant manager When I worked at a gym called Bally Total Fitness, selling memberships, and then a year removed the summer of 2005, I saved up my money and I went to this event called an exposure camp. Now many people don’t know about those. And exposure camp is like a job fair, but it’s for athletes. But instead of a bunch of athletes showing up with resumes, and wearing suits, and telling people what we can do, we actually bring our sneakers and our gear, and we play our sport in front of everybody. So people were familiar with the NFL Combine, it’s a similar idea. There was what the NFL Combine is that everyone still has the possibility to get drafted. Whereas at an exposure camp, you got a bunch of nobody does the combine, you probably heard of a lot of those players if you follow college sports, but in a basketball exposure camp, you anybody can basically show up, they’ll take anybody’s money, they all act like they have a selected process. But if you’ll pay, they’ll take your money. So I saved up my $250. That’s all it costs. And I had to pay at the door because I didn’t even have I didn’t have a credit card or bank account at the time. So I get there, pay my 250 at the door. And it’s a two day event. Saturday, Sunday, you got two days about 200 basketball players there. And we’re all trying to prove that we are good enough to play pro. And at that two day event, I did pretty well got it nice scouting report got my foot is from that. Whatever is that to get myself a basketball agent, and I’m skipping over some parts that does not make it to home, but got myself a basketball agent. And that agent helped me get my career started. So my first job was encountered with Wynia in 2005, at the age of 23 years old. Now at the same time, I took the footage from that exposure camp. It was on this device called a VHS tapes got you remember VHS?


Scott D Clary  06:35

I do and that’s your you’re dating yourself, man. It’s


Dre Baldwin  06:38

exactly, exactly showing my age. So yes, that VHS tape. I knew that you know, anybody who remembers VHS and those of you listening who don’t know what that is no, Google it or ask your parents, they’ll tell you. So with the VHS tape, I knew if you drop it, it gets wet, you give it in the sun, that footage is destroyed. So I’m like, Man, I gotta save keep this footage forever, because this footage is like my golden ticket in the plane Pro, because that’s what I needed. The reason I didn’t get I didn’t have any scouts looking at me when I got out of college because I didn’t have good game footage of me playing against pro level players. Because again, I was playing against Division Three players. And most of those guys are not pro level. But that exposure camp, those are better players. And I played well against them. So I needed that footage. So I got that footage, I took it to an audio visual store, they put it on a data CD, and I took that data CD and I put it in my parents desktop computer, and upload it to this new website. I just heard of Scott. And on his website, they said, you can put up as much footage as you want completely for free. And it’s called This is 2005. So this is how I started a parallel career didn’t even know this is going to be a career because in 2005, nobody was talking about this. We weren’t using phrases like content, personal branding, social media, those phrases did not exist in 2005. So I just put the footage up there just for me. It was just for me, because who was on the internet looking up Dre Baldwin? Nobody. So a couple years later, not even years. But months later, I went just to check on the footage. And I saw there was comments on the video. And there are people asking like, Hey, who do you Who taught you how to play? How often do you practice? Or where do you go to school, because they can see that I could play they didn’t know who I was they see like this guy looks like he knows what he’s doing. And I realized very quickly, Scott, that this was an underserved community that basically the people watching my videos were, they were me, but 10 years younger, they were the players who wanted to play ball, but they didn’t have anybody to teach them. The event is that they had over my generation, our generation is that they could go to the internet and get information. Whereas in my generation, nobody was there to teach, you had to figure it out on your own, or you just didn’t. So I once I saw that they just wanted me to make more videos, I just kept making them. And I did it sporadically at first and it was around around 2009 2010 I found myself out of a job in basketball. And I started making the videos more consistently because now Google had purchased YouTube, they said, well, we’ll give you some ad revenue. We’ll share the ad revenue with you if you make videos and you’re popular. And again, this sounds like common sense now, but this is not common sense to 2009. So and they’re like what you make money just by putting videos on the internet again, back then if you were doing that you were a bum living in your parents basement who need to get a real job, right? You remember those days so that? Yeah,


Scott D Clary  09:12

you’re early. You’re early YouTube man. You’re early. Yeah, exactly. Yeah,


Dre Baldwin  09:17

right blogging as well. So around that time, that’s when I really started focusing more on internet thing. And the funny thing is no, all the work you do to become a pro athlete, but most of the people who recognize me if I’m out in the street or at the mall, they recognize me from YouTube. Nobody recognized me from overseas basketball, because who in America watches overseas basketball? Hardly anybody. So that’s the is the ironic thing about the whole situation and just to tie this whole thing together. I’ll fast forward next 10 years, players started asking me questions about mindset because they realize they’ve heard about my background of how I barely made it in high school and how I had to hustle my way and sort of proves walk on in college so they were asked me about you know, why did you keep doing it? Why did you keep trying? Why did you keep practicing? How did you keep the vision alive in your mind? And that’s when I started Talking about the mental tools. And I’m sure we’ll get to here, Scott, that became the foundation of my philosophy now just called work on your game. And when I started talking about those things, people who didn’t even play sports, started finding my videos and my articles and things like that. And they would tell me what is right. I don’t play sports. But the way you talk about mindset, anybody can use that that’s valuable anybody. So that planted a seed in my mind, when I’m done playing ball, I can take this piece, the mindset stuff, and I can teach this to anyone, I don’t have to limit myself just to athletes. So when I stopped playing ball in 2015, I just went full speed ahead on the mindset stuff, and took it into what we now call thought leadership, which is writing books speaking, no coaching, consulting, podcasting, things like that. And now today, my company is called work on your game, you could guess. And it’s all about taking the mental tools that help athletes get to the top 1% In sports, and leveraging those same tools at work and in everyday life. So serving entrepreneurs, professionals, of course, athletes, anybody who really just wants to maximize their max max out on their potential, and make sure that they’re making the most of their opportunity. So that is my backstory. And I think that was five minutes might have been longer.


Scott D Clary  11:07

That was right, no, that’s pretty good. That was pretty concise, and succinct. And it was a good story, because it tees up exactly how you got to where you are today. And you know, even looking at you now like just like looking at your bio, I see so many reasons why somebody who has been a high performance athlete would have so many lessons to teach somebody who is trying to build a business or what but it’s something that, you know, sometimes you follow, like the football coaches or whatever, and you get like, you know, the business tips from them. But I don’t see people that actively pivot an entire career, and then understand how the lessons they’ve learned, operating at such a high level can be so applicable to an entrepreneur or somebody starting out from the ground up, I think that’s what’s it’s incredible how your story evolved. And like all these different inflection points in your story just led to you being able to have the experience and the platform, because that’s also very important to be able to do this. So as you so as you pivoted from pro ball, and then you started, like down the thought leadership pathway, walk me through some of the things that you realized were applicable for a high performing professional athlete that are also applicable to an entrepreneur, because that’s what you speak about. And that’s what you do. TED talks on. That’s what you write books about. I think that’s also a lot of your content on Instagram, whatnot, a lot of these these certain mindset things, and not just mindset, but actual application of certain things can be super applicable to entrepreneurs. So what are those things you discovered?


Dre Baldwin  12:41

Sure. So really, it kind of went back to what the athletes were asking me because really, the foundation of it was me just answering questions to the athletes. And they would just say, Well, why come to the gym every day in practice? Why come to the gym every day and work out and then put these videos out? And honestly, Scott, I thought it was a normal thing. I thought that’s what every athlete did is I’m figuring I play basketball, I want to play pro, or I’m already playing pro, I need to get ready for my next job opportunity to just go to the gym every day practice so that my game is sharp. So when that call comes in, I’m ready to go. I thought that’s what any athlete would do. But what I realized very quickly was that not every athlete did this because when I showed myself doing it, people were looking at it like they couldn’t they were surprised. And I’m like, Isn’t this what anybody would do, you have a job, you show up ready for your job, or at least ready for the job that you want, you prepare for the job that you want, before you even have the job. I thought that was normal behavior, a normal mindset. So that was where the discipline came from showing up every single day to do the work. So that was the number one principle and is still to this day. That is the foundational point, I think, for any professional in anything. Because if you look at the dictionary definition of professionals, a person who gets paid to do something as it may not be patient, but my definition of a professional is a person who shows up every day and delivers regardless of how they feel. Because some days were sick. Sometimes you’re tired. Sometimes you don’t feel like turning the mic on. You don’t feel like writing another pays for your book. You don’t feel like being in the gym, but you’re getting paid for it. It’s your job. You got to show up and do the work just like you think of your favorite who’s your favorite athlete Scott?


Scott D Clary  14:15

Woof was my favorite athlete. Let’s take it back like like Muhammad Ali like someone like back like, like he Yeah, go for it. Go for it. Go for a box


Dre Baldwin  14:25

Muhammad Ali. Now I’m sure now during the matches that everybody was watching Muhammad Ali. He was all keyed up and ready to go as many because boxing is not like you’re boxing 80 times a year or 160 games a year like baseball, but I’m sure there were days Muhammad Ali did not feel like training. No boxers do rote work and they run the miles and they gotta hit the bag and they got to do to jump rope. I’m pretty sure in Scotland you can tell me if you disagree. There were days Muhammad Ali did not feel like training. But he understood right because of his position. And because of the next person he was fighting in. Because fighting him was like the grand prize of anybody’s career, he knew he had to show up and do that training so that he will be ready to deliver every time so that no, somebody couldn’t make a they can make their whole career based off of beating him, you know, so he had to be ready to show up every day. Are you think of a Lebron James? Does he feel like playing every single time at two times a year, knowing that he’s getting the best shot of every player he plays against as every player wants to be able to say, Hey, I’ve dunked on LeBron James or I stole the ball from LeBron or I scored on LeBron twice, in one game 12 years ago, you know, everybody’s trying to get their highlight off of him. So he has to be that mentally on point every single day. And that’s much more of a mental decision than it is a physical skill. Now, a lot of people don’t really understand it. So they constantly think about it. So that first principles discipline. The next one’s gonna


Scott D Clary  15:47

say, I was gonna say just one thing. No, I just wanted to point out something. The only reason why I picked Muhammad Ali is because I love I love boxing as a solo sport. And I find that and maybe you just comment on this, if you think there’s something to it, like, you think there’s a certain mental toughness that can be pulled from a solo sport versus a team sport, not to say obviously, like, at a team level, like mental fortitude, and the psychology to show up everyday is not important, because it obviously is, but like, there’s no team holding you accountable when you’re when you’re on your own. That’s I thought it was I thought that was something that’s super impressive. When I look at boxers, it’s probably some of the most notorious like solo sport, you’re just showing up on your own with your coach.


Dre Baldwin  16:26

Absolutely. And no, it’s funny, because since I stopped playing ball in 2014, a lot of people always ask me, Jerry, do you play pickup you play in the leagues or anything, I play zero basketball, cold turkey. Because to me, I’m always in a mentality of I can’t be at my best, or whatever my best potential is, at that moment, I want to play at all because I don’t want to be like the old guy with some young guy who’s isn’t half of what I was at his age, no beaten me, just because I’m not in shape anymore. So I don’t play ball at all. But I do have a boxing trainer. As a matter of fact, I had a boxing workout this morning. And you’re 100% Correct. Because in a solo sport, not only do you not have a teammate holding you accountable, also in the matches in the games, the performances is just you out there, you can pass the ball to somebody else like in basketball. If I’m not making my shots that night, I can pass them on to my teammates, if he’s making all the shots, we can still win the game. But in boxing or tennis, if my surf is off, or something’s wrong, my ankle and I’m not moving the right way, I can’t hide, I can’t pass the ball to anybody and still win the game, you’re going to take that loss and everybody sees you. So absolutely. In a solo sport, it’s a completely different approach. Because you have to, you kind of had to be your own accountability, even though no boxers have trainers, and no tennis players have whatever swimmers and he’s always sport, they have trainers and coaches Exactly. But in the performance, there is no one to pass it off to during that performance. And when you lose, you can’t point it, anybody and when you win, all the glory goes to you. So 100% Agree.


Scott D Clary  17:56

Anyways, you’ve gone through I don’t mean to interrupt you. That’s that was interesting, because that’s, that’s sort of like the, you know, I always equate sports to start up and like as an entrepreneur, like, you don’t have a team day one. You’re 100%. So day one. Yeah. Right.


Dre Baldwin  18:09

So discipline is the first principle that the work on your game is based on. The second one is confidence. And this is the one that usually if someone comes to me, and they’re asking for anything, mindset wise, usually they’re asking for confidence. If they don’t know anything about me, they use the same God, I want to be more confident, I want to have more self esteem, I want to believe in myself more. And why is that? If you ask somebody, why do they want more confidence, they’ll usually say something like, I’ll perform at a higher level, I’ll be more consistent, I’ll have more, I’ll be better able to sell my products, start up conversations with people, you know, close people on my products and offerings, whatever it is, everybody wants confidence. What many people don’t understand is that discipline creates confidence. That number one, number one main source of confidence is discipline. Because if you think about it, Scott, the most confident people, you know, are usually very disciplined individuals. And very disciplined people are usually very confident. And why is that is because those discipline people, because they’re showing up and they’re doing the work and they know that they are following their their principles on a day to day basis, they have earned the right to be confident. So confidence is defined as your your belief in your ability to do something. So where do you get that belief from from actually doing it? Now, if you haven’t done the thing before, let’s say you practice that, let’s say as a boxer, or a business person, you’re trying to sell something, you’ve done all the practice, you listen to tapes, you’re ready, but you haven’t done the actual performance yet. Where do you get that confidence from? Now, some people have this concept of faking it until you make it but I actually don’t believe in that concept. I don’t believe we fake it till you make it, I think is a misnomer. Oxymoron. The reason is because the subconscious mind doesn’t know the difference between imagination and reality but at the same time, it takes everything literally. So when you tell yourself that you’re faking it till you make it. It’s kind of like Cinderella. Notice in the row as she puts on that glass slipper. She has this beautiful ballgown but at some point Ain’t no clock strikes midnight, she goes back to wearing rags. And that’s what happens to people, when they fake it till they make it is that eventually you’re going to tell yourself to Stop faking it and all that confidence that you had, you go back from the beautiful bog down to the racks. So what I suggest that people do instead is become, because you don’t have to fake it, you can just become that person. And I give an example, one of my TED talks, I talked about this a basketball player, he was in practice, and a coach told him that day, I want you to pretend to be the best player on the team. And this guy was this player that he was talking to was marginal player, maybe the 10th best player on a 12 person roster. But that day, when he’s pretending to be the best player on the team, he’s doing all kinds of crazy moves. He’s making all kinds of miraculous shots that he never does. And all his teammates are looking at him crazy. Like, where’s this coming from? We didn’t know you had this ability. And what he had done is he had stepped into this principle that I call it a super u, which is you still being yourself, not faking it. But as you are at your highest possible level of confidence. And what you do in that moment is you borrow that confidence from another person. So to give an example, you take a say somebody who’s a boxer, and they are them, whoever they are. Now, before they go into that mess, they’re looking for that confidence, I will tell them listen, I want you to think about somebody like Muhammad Ali, or Mike Tyson or Floyd Mayweather, or whoever your favorite boxer is. And I don’t want you to try to beat them in the ring, because you don’t have their same wiring or skill set. But I want you to look at think about their mentality, think about how they would walk into the ring, think about how they would approach the fight? How would they feel about themselves going into running? How would their confidence be? How would they? How would they picture their performance leading up to the game for a basketball player? I saw a picture of Michael Jordan or Kobe or Steph Curry, what is their confidence? How do they feel about themselves? How do you look at themselves in the mirror before the game, now I want you to think about yourself the same way they would think about themselves. So you’re basically mirroring their mentality, not necessarily their actions. And that way, you can step into a level of confidence that maybe that person has never had before. Because as humans, we have these things called mirror neurons, like you can watch somebody else do something, and just by watching him do it, you have a better understanding how to do it, even though you haven’t done it before. And that works for confidence. It works for no hammering in a nail, it works for repairing a car, it works for anything, but people have to understand the principles behind it and understand it, you’re not trying to be somebody else, you’re still being yourself, you don’t want to be faking it because eventually, like I said, faking is going to end you don’t want to tell your brain to you’re pretending to be anything. So the second principle is confidence. So


Scott D Clary  22:33

and just I want to ask one question on that one. Say you, I understand the concept. And you put your mind in the space of somebody who has that experience, and he’s done it a lot. So now you have that confidence, you’re becoming it? How do you make sure that when something doesn’t go according to plan that you can maintain that confidence? How do you not break this perception? Because I feel like it’d be human nature. The second, I’m going for a shot that I’ve never made before. And I don’t make it all of a sudden, I get in my own head. And I just realized that I tried to do this thing to become this person. And it worked for 90% of the time, but then that one time, that didn’t work. I’m like shit, I’m not that person. I completely screwed that up. Because you haven’t you’re not that person. So how do you how do you keep adding? Keep that mindset? Right?


Dre Baldwin  23:19

Great question. So this is that’s part of your training. That’s part of the mental training, ahead of the performance. Because if you think about it, every professional prepares for the situation before the situation. And amateurs get into the situation, then they try to prepare while they’re in. So part of your training is to be ready for that situation. This is why every athlete has a coach, every athlete has a trainer, every athlete goes through a lot of practice before they get to play in the game, you don’t practice you don’t put. But in the professional world, outside of sports, we have a lot of people out here the kind of freelancing and not not like as a freelancer but freelancing, meaning they’re not preparing and training for the situation before they get into it. So an athlete, if I’m training a basketball player or a boxer, for example, I’m getting them ready for the fact that they’re going to miss a shot, that they’re going to try and move in, somebody’s gonna steal the ball from them, and they’re going to try to dunk and they’re going to miss the dunk, or they’re going to get their shot. But I think we get crossed over and scored on two times in a row by somebody else who’s better than them. And they have to be mentally prepared for that so that when that situation occurs, they know how to deal with it. I’ll give you an example. Did you see the tiger was documentary? I think it was on HBO. Max. You see that?


Scott D Clary  24:29

I think I think so. I can’t remember now though. It was It wasn’t a while ago, I think I think I have yet but I just don’t remember I don’t remember specifically.


Dre Baldwin  24:35

I think maybe a year or two ago it came out but I just watched it probably this year. But in that Docu series, you see when Tiger was coming up as a golfer because his dad taught him how to golf right. So he’s 1415 years old. He will be out on a on a LYNX golfing. His dad would be with him and his dad would do stuff to distract him. When Tiger was lining up a putt, his dad would walk through his mind before he put it or when he was just about he was in his backswing because that will call off or laugh or make some noise and try to distract him. And the whole point was teaching Tiger like, look, these kinds of things might happen in the real match. And you have to not come unglued not become unwired, and you got to deal with it, and be mentally tough enough to deal with that situation because he saw a Tiger had the talent, he had the physical ability, but it’s the mental ability that unlocks the physical ability. So it’s making sure that you’re doing the preparation ahead of time and not preparing for everything to be perfect. or preparing for the fact that things will go wrong, and they’re gonna go off course, Are you mentally? Do you have the mental dexterity to deal with that situation on the fly when it happens? Because it’s going to happen?


Scott D Clary  25:40

Good, good. No, it makes sense. So that’s, that’s part of the that is part of the prep. So when even if you’re going into even if you’re going into a situation where you are becoming something, so that you have that, that mindset, you can still be doing the prep ahead of time, so that you’re aware that when things don’t go 100% The plan. And this is actually, you know, this is something that I don’t think you have to do for a specific event, right? Like, it’s not like this is a mindset that you can carry with you through the next job, you’re going into next interview or going into the next startup you want to take on it can it can be a mindset that even if even if you’re casually just taking up a sport and you want to you want to play a sport, and you’re you know you haven’t played in a few years like it is the mindset just just preps you for things not going right? You take it everywhere, right? It just like you just have to know it. That’s how you have to think,


Dre Baldwin  26:28

exactly. And just understanding that life is not always going to go in your favor exactly as you want it in the way that I describe it to people is playing a road game. It’s like playing a game on the road in sports, because, and let’s say a sport, like football or basketball, no team wins the championship without winning some games on the road, you have to be able to go into a hostile environment where things are not set up and your favorite people don’t want you to win, and they are not going to move out of your way. And you have to figure out how to win anyway. And no, it’s funny, I was just listening to Zig Ziglar secrets of closing the sale tape. And I listened to that tape all so many times. But one of the things that he talks about is that you got to be able to close the close ones, because as a salesperson, you’re going to have some gimmies, you’re going to have some customers who come in, as they say sometimes with their credit card on your forehead, you’re gonna that’s an easy sale, but you can’t build the whole sales career just on easy sales, you’re gonna have some of those co sales where it could go either way. And if you don’t close enough of those close ones, the road games, then you can’t build a career in sales. So I was understanding that there are going to be some situations that could be you might win, you might lose, you gotta win enough of those to get by. And then the easy ones would be the easy ones, then there’s gonna be some that you’re not going to win no matter what. But you got to win enough of those 5050 games is the same thing as sports is the same thing in businesses and sales isn’t everything in life.


Scott D Clary  27:47

Sorry, sorry. Okay. What? Okay, so after this is confidence, but I think it’s sort of dovetails into the next point as well. Yeah. So yeah. So So walk me through that. Walk me through that. And how does that obviously, actually go for it? Then I have a question. I follow up after pickle for first.


Dre Baldwin  28:04

Okay. All right. So we have this point in place, showing up every day doing the word confidence, putting yourself out there boldly and authentically. The third principle is mental toughness. Now mental toughness is your willingness and ability to continue being disciplined and confident despite the fact that following the program, following the rules, your discipline and your confidence have not yet produced the desired results. So this is right, what what you just asked about that, just because you followed everything perfectly. I mean, if you ever signed up with a coach, or you sign up for a course, or you’re following some somebody who has a 10 step process to produce outcome XYZ, and you follow exactly what they said, did exactly what they told you to do. And you did not get the desired result. The mental toughness is do you look at it and say, let me figure this out. Let me figure out what’s missing here. How do I fix this? How can I go about this a different way, or you just throw your hands up, give up and quit? And while it sounds so trite, and it sounds so common sense, maybe to many of the listeners, people who listen to a show like this, you probably wouldn’t even think of even needing to make that choice. But there are so many people out there who, when things don’t go the way that they expected or don’t go according to plan or no one real life alters that lab test, they just give up. They just they just don’t keep showing up. And persistence is one of the number one traits of successful people is that they’re just willing to persist. They don’t quit when things don’t go their way. They just regroup and they figure out a way how can I go at this problem? A different way to make it work out and anybody who works in startups? I mean, this is your whole business. Right? This is the the entire thing is being persistent, even though it didn’t work exactly how you thought it would.


Scott D Clary  29:42

I just want to take a second and thank the sponsor of today’s episode. HubSpot. Now, as a leader, you’re always on the lookout for more ways to arm yourself with knowledge, the books, the seminars, and most importantly, the podcast and help you make the best possible decision for you, your company, your customers, because when you know No more, you can apply more. And you can grow with HubSpot CRM platform, you can store, track, manage and report on all the tasks and activities that make up your relationships with customers. With a bird’s eye view over all your customer interactions HubSpot empowers your decision making like never before. So you can give your business and your customers all the good you’ve got learn how to make your business grow Do you have an you make a point that I’m sure that people listen to a business or you know, an upskilling focused podcast where you’re trying to learn how to be better and do better? I’m sure they do have a level of mental toughness that maybe the average person doesn’t but even then, like when, when stuff doesn’t work out, like it’s hard, like, it’s just really, it’s really hard. Like there’s no way around it. So somebody that teaches us for a living? Do you have tips on how to condition yourself so that when things don’t work out, and it’s easy to pivot, and you have to pivot? Maybe you have some sort of kind of like what you said before, like you you know, you’re preparing for things to not go right? What is an exercise that you could do, so that you can prepare for things to not go, right? Because if you can prepare for things to not go right, you can pivot quickly, you can go into something new much quicker, you’re not letting yourself get in your own way, and slowing yourself down. Because of like, what, what’s in your head? So how do you condition yourself for mental toughness is the question,


Dre Baldwin  31:29

great questions about my book work on your game, as you can see over my shoulder right there. The first chapter of that book is called mental conditioning. That’s the very first chapter of the book. And you think about conditioning, if anybody if you ever play a sport that involves running like basketball, baseball, football, one of the things that we do at the beginning of every season training camp is we do conditioning workouts, and what is it conditioning workout is just a whole lot of things that are designed to get you physically fatigued. And the whole point of that is not so that what many people incorrectly think they think being well physically conditioned means that you never get tired. Now trust me, I still I still run know, probably a 10k, three times a week, here in Miami where I live. Every time I run, I feel fatigue. Even though I’m in great shape, I feel fatigue every single time. Even though I’m in physical condition. What conditioning means is not that things are not going to happen. It’s just a matter of how much time do you need to recover before you can get right back at it. So when you’re well conditioned physically as a basketball player, for example, if you go sprint up and down the court 10 times in a row, even LeBron is gonna get tired, Kobe will get tired, Steph Curry will get tired, it’s it’s a matter of Steph Curry might only need 30 seconds of breathing time before he can run full speed all over again. Whereas somebody who’s not conditioned, they might need 30 minutes or 30 days before they can run full speed ever again. So that’s what conditioning is about. It’s about shortening the amount of time you need to deal with the setbacks and challenges when they inevitably happen. So how do you get ready for that is it goes right back to the preparation and being ready ahead of time of what’s going to happen and anticipating the fact that there may be challenges. And that’s what’s your work into your strategy. Because going back to boxing analogy from boxing is, is not the hard punch that knocks you out is the punch that you didn’t see coming. You see somebody get knocked out in boxing, it’s not because they got hit so hard. It’s because they didn’t know it was coming. And surprise them. That’s when they get knocked out. And it’s the same thing in life is that if you anticipate that there will be a challenge, then you’re you can much better deal with the challenge because you knew it was coming doesn’t make it any easier. But it feels easier. And you can make it look easier, simply because you got ready for it. And actually, my newest book called The third day is all about that. It’s conditioning yourself to deal with the challenging days, that third day is that challenging day you got the startup, you’re going, everybody’s excited for you. You’re excited, you got all this initial attention coming into you. You’re selling your product, it feels good. But then that newness wears off. The novelty is gone. And now it’s just you by yourself. And they everybody has moved on to the new guy who has something new to came out newer than yours. Now what do you do? And it’s at that point right there that a lot of startups and you can tell me if I’m wrong about this guy, a lot of startups don’t make it past that point. Because that’s where definitely don’t, right, that’s the newness as more know. Exactly. Now, you got to grind through that part, that third day is what I call it, you got to grind your way through that. And if those who grind through it, then they might get to the point where they can see the light of day. But a lot of people and a lot of businesses and a lot of situations just don’t make it through that point. So that grind right there. That’s what makes the professional is dealing with that grind. It is not the talent. It is not the opportunity names are not the resources. It’s the mental toughness to grind through that tough part that is going to come to everybody


Scott D Clary  34:52

just on that point. So actually, when when people are building something, and this is something that I see often they focus on building and they all in theory, love what you just said and all makes sense. And nobody would argue these are all important things. But then you get stuck in the day to day you get stuck in the doing and and you have to execute on things and life is busy. So what do you say to somebody who knows that this is like focusing on your mindset getting your mind, right? They know it’s important, but they just never quote unquote, like find a time to invest in building themselves so that they can help themselves in the future when they actually need some of the things that you’re speaking about. How do you how do you get that person on board? Or is that not the person? The focus on? Do you focus on people that are already trying to help themselves?


Dre Baldwin  35:46

Well, it’s a combination of both because the people who are the people who understand the value of that are the kind of people who come find somebody like me, because they understand the value of it, and they’re like, I know, I need to make this investment. Because I know these challenges are gonna come up, or I’m already dealing with these challenges. Now, on the other hand, and people who are not aware, or they’re not constantly thinking about it, they one of two things is going to happen. Either they will, they can hear the message from like this conversation right here. They might be listening to this and saying, okay, you know, what that actually makes sense. Let me go read a book, let me go listen to some more Scott stuff, let me go see more of what Dre is talking about. And then maybe they’ll they will convince themselves because we can’t convince them, they gotta choose themselves to get more into this, or the other thing is going to happen is they’re gonna get their butt kicked by life, by business, by the industry by situation. And then they’ll realize, oh, okay, this is what they were talking about, okay, let me make sure this doesn’t happen again. But one of the two things has to happen, but there’s nothing that I can say or that you can say that is more valuable than what they say to themselves. And that’s either like kicking their butt, and then they say, or they get the idea ahead of time. So what is going to happen one way or other?


Scott D Clary  36:56

That sort of dovetails into the last point, and that’s what I was trying to figure out, like, personal initiative, holding yourself accountable, and just being, you know, self aware of what what you’re good at what you’re capable of, and maybe some of the things that you need to work on. What is personal initiative? How does it fit into this framework of discipline? Confidence, mental toughness? Is it just like what you just mentioned? Is it being self aware of the fact that you have to go and work on these things, read a book, focus on getting your mind right before you start building something? Or is it? Is it holding yourself accountable? Once you’re already down a path of building something? What is your version of personal personal initiative mean?


Dre Baldwin  37:41

Well, both of those are part of it in the way I describe personal initiative as being that go getter. A person who goes and makes things happen instead of waiting for things to happen. So you in the line of work determine Scott, this is exactly this should fit you to a tee. And what bayonet go getter means is understanding that the three things we’ve talked about so far are all mindsets, discipline, confidence, mental toughness, a way of thinking that you could do all of that by sitting in your seat and never doing anything. You could read about it all day, and watch YouTube and listen to podcasts and all that stuff. But personal initiative is taking that potential energy and turning it into kinetic energy, energy in motion, going and actually doing something. Because these days with, I mean, how many people have a podcast? How many people write books, how many people are making YouTube videos, right? Everybody, literally everybody is doing that. So the thing is, many of us these days, can get into what we call analysis by paralysis, right, or paralysis by analysis is that we’re just taking in all this information. And we’re thinking about this and that, and there’s all this new stuff that we can get. And we don’t feel like we know enough to take action yet. And we don’t want to make cold calls. We don’t want to put our product out there because not quite ready. The problem is by the time you figure out what to do, the opportunity is gone, the options are gone, your vitality is gone. So the important thing for me and this is something that I tell people all the time, I call it the 10% rule of information in action. So you only need 10 person information to get started. To take action, you only need 10 person information, then along the way, you will learn more. And I guarantee you you’re probably not going to get the perfect result when only 10% of information, however, you make your self eligible to get to the perfect result because you got started because you moved because you put yourself out there. Now you can get some feedback from the universe, you can get what I call activity knowledge. And you can figure out how does this stuff actually apply to Dre and Scott are talking about here. Let me say how this applies to me how it applies to my life and my particular situation. So if you’re sitting around waiting to get all quote unquote, of the information, first of all, that’s impossible because information is being created at a faster pace than any of us can take it in. So you can never get all the information and whatever is information right now today, two weeks from now is not going to be information anymore. It’s something has changed. So you have to be willing to move without knowing everything and actually being comfortable in that being uncomfortable in your ignorance. I guess we can call it being comfortable in the discomfort if you even want to call it that, of knowing that things are always changing around you but trusting that you will be able to change with it. That’s what personal just centers


Scott D Clary  40:13

and ultimately just taking action because then you get like that’s the main takeaway is take action like get get that momentum going to get that flywheel of like activity happening. And that’s, that’s going to propel you to figure stuff out to do something new to get to the next level. Like, it’s just all about, like, at the end of the day, it sounds like common sense isn’t common, but it sounds it sounds so simple. It’s like just get your ass started. And then everything else starts to fall into place not easily, but things start to happen.


Dre Baldwin  40:43

It’s common sense that people I guess, but it’s not common sense to the average person.


Scott D Clary  40:47

No, no, fair, fair. If you had, if you had one lesson, because you teach you teach a lot. If you had like one lesson that you’d want people to take away from all your work, your TED talks, all the content you put out the books you write, what would what would that lesson be? What would the like be the mark that you want to leave? On the words that heavy question, but I’m curious


Dre Baldwin  41:11

is that mindset is the foundation of everything. Mindset is the foundation of creating success is the foundation of winning is the foundation of taking yourself to another level, even if you feel like you are already successful. The person that got you to where you are today is not the person that’s going to get you where you want to be this time next year. There is something that needs to change about who you are being as a person, not your actions, the actions come after. But something needs to change about the way that you think and the way that you see yourself and the way you see your business in order for you to take your business to another level. And when you change how you see yourself and the way you think the actions will automatically follow. Because I’m a person who doesn’t work out, for example, and I changed my mindset to someone who does work out well, what am I going to do, I need to get a gym membership, need to give me some sneakers, I need to make sure I wake up an hour early so I can go work out before I go to work, the actions will automatically follow the mentality. If you truly believe it about yourself, you will take actions that match what you see. And it is impossible for any human being to consistently act or an extended period of time in a way that is in conflict with the way that they see themselves. So when you change how you see yourself, your actions will automatically follow. So mindset is the foundation


Scott D Clary  42:18

that’s always that’s good. I love that quote. That I love that quote. So if you’re if you like that, that that brings it back to the Start man that brings it back to the you cannot fake it till you make it. It’s your you’re going to your mind is going to self correct at some point it’s going to shatter this whole perception you’ve built for yourself. So it’s not fake it till you make it. It’s just getting your mind right and then executing against that proper mindset. You said it much more eloquently than me. Paraphrase.


Dre Baldwin  42:48

You can clip it out and clip it out and use it.


Scott D Clary  42:51

No, that’s that’s that’s a social clip for sure. That was that was good. Whatever you just said like, like 60 seconds ago, that was golden. Okay, I want to I want to do a couple rapid fire just to pull out from your career, some insights, you’ve done a lot in your career there your pro career, obviously, all the content, you’ve put out the books, the TED Talks. But most importantly, before I pivot, where can people connect with you? So what are all the socials, the websites that you want people to go check


Dre Baldwin  43:20

out? Well, I’m on every social media platform, not on tick tock, I have a tick tock account on post there, but I’m everywhere else. The one I’m most active on probably is Instagram. I use Instagram stories all day every day. So you want to get a really good inside look and a good feel for my personality Instagram story. My Instagram is just my name at Dre Baldwin, my newest book, The third day, I give people a free copy if they just cover the shipping. Can I tell them about that? Scott?


Scott D Clary  43:44

Yeah, do that man. Do it and give me and send me a link. So I can put it in the show notes. But for sure.


Dre Baldwin  43:49

Oh, yeah, sure. Well, so this is the newest book called third day, the decision that separates the pros from the amateurs. This is one of my this framework is about discipline. And we talked about discipline at the beginning of the show. The third day is the framework that I use to explain it. And whenever I give speeches I talk about the third day, this is the thing that people remembered the most. So I went and wrote a whole book just about this. So this is the biggest, most popular framework within work on your game. And it’s all about your ability to show up on a consistent basis and deliver consistently and that seems to be the thing that people ask me about the most How can I be more consistent? How can I make sure I’m sticking to my discipline, sticking to my habits, sticking to the things I said that I want to do. That’s what the third day is. And the third day is I’ll give a quick metaphor for it. You show up to the gym, let’s say we got a new year coming up when it comes out might already be in a New Year. Everybody comes to the gym in January, right? Anybody who goes to the gym, you know January you hate going because you got all these people who you know won’t be there in two months. Everybody’s in the gym, right? That’s the that’s the first day metaphorically it doesn’t have to be days second day. And I’d say that’s the middle of January. People are still showing up but it’s not new anymore. They’re getting there a little bit later and given up even a little bit earlier, not showing up quite as often. The third Day is probably let’s say, by Valentine’s Day, you got the same people that were there before, the same people from last year. Now all the new people that that they forgot their gym membership. And I don’t know if people noticed, you know that 50% of gym revenue is people who never show up to the gym. That is people who have memberships before. Yeah, yeah, but they don’t actually ever show off that. Yeah, they make most of their money from people who never come to the gym. And the thing is that people, if everybody who had a gym membership regularly use the gym, the gym would not have capacity to service all those people. So they factor this into their business model is that most of the members will never show up. So that’s the third day is the newness is gone, the novelty is gone, you realize that this thing that you signed up for, and even if you’re paying for it, this is some actual real work, I had to actually do some work here to start up as real work. Alright, having a podcast is actual work, this relationship is real work, or this gym is actual work. And that’s when you separate the pros from the amateurs who is going to show up, that’s what this book is about. And I’ll give you a copy for free, I’ve got to tell you, it is third day And I’ll Scott, you’ll have the link, so everybody can just click on it and go to copy. Third day, the book is free, all you got to do is cover the shipping, and I will physically ship you a copy of that book.


Scott D Clary  46:14

Amazing. Thank you, man. Okay, so let’s go into some rapid fire questions to pull out some last insights from you. Biggest challenge you’ve overcome in your own personal life, or professional life. But what was that challenge? Had you overcome it?


Dre Baldwin  46:27

The biggest challenge I had to overcome was really just developing the confidence, the confidence as a person the confidence, to talk to just people to talk to audiences, then as an athlete, and then in the business world, and then some people see me now and they might not think that but the reason I’m able to teach confidence because I know what it feels like to be at zero and I know what it feels like to be at 100. So confidence.


Scott D Clary  46:47

Okay, good. If you had to choose one person, obviously, there has been many, but one person has had a major impact on your life. Who was that person? What did they teach you?


Dre Baldwin  46:57

I have to go on my favorite author, Robert Greene, who wrote the 48 Laws of Power 33 Strategies of War, the 50th law. And what I learned from him is really just learning to look really introspectively into people, not only other people, but also myself and think about the psychology behind people’s actions. I’ve always been into that. But when I read his book, he was speaking directly to me. So it got me more into it. So Robert Greene.


Scott D Clary  47:20

Good, good. Good. So this is you answered two questions with one but I’ll give you the next one is a book or podcast you’d recommend so another book? Yeah, go for it, go for it.


Dre Baldwin  47:32

Another book I recommend is the law of success by Napoleon Hill. Now most people know Napoleon for thinking grow rich. But the law of success was like a it was like a course that he created it and from within the law of success he grabbed thinking grow rich, he basically extracted it from the law of success and may Think and Grow Rich was became the most popular business book of all time. But that book is a super long but but it is worth the time investment to read it. I mean, read with your eyes and get the audiobook I got the audio book and the physical book. And I have read that book many times actually need to read it again. So that one off success.


Scott D Clary  48:06

Just out of curiosity, are you more of an audio book or like a physical book person?


Dre Baldwin  48:11

I used to be very physical books, but then when audiobooks came out and just the demands on my time, I do audiobooks more now, so I’m more audiobook now.


Scott D Clary  48:22

Yeah, I am, too. I was just I was just curious. Sometimes there’s something to be said for like actually sitting down and opening a book, but I found myself doing podcasts or audiobooks. At like 1.5. Exactly. Yeah, yeah. Good for you.


Dre Baldwin  48:37

I had a time like I used to.


Scott D Clary  48:41

Which is again, it’s a good problem to have. Right? Right. Okay, if you could tell your 20 year old self one thing, what would it be?


Dre Baldwin  48:48

No easy question. Invest in yourself. Invest in yourself, meaning getting around the right people. Invest in reading books, invest in getting information that is not going to be taught to you in school is not going to be taught to you by your parents, and people who invest in themselves. They grow by multiplication, whereas people who don’t invest they only grow by addition. So everybody’s growing. It’s just the people who invest they they grow faster. So invest in yourself.


Scott D Clary  49:12

And last question, what does success mean to you?


Dre Baldwin  49:15

Success means being a person who you’re proud to look at in the mirror and living the kind of life that you want to live. Not what everybody else thinks you want to live or what everybody else wants for you, but what you actually want for yourself. So success really comes down to an honest conversation that you have with yourself, not what anybody else thinks about you.



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