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March 12, 2024 44 mins

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

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

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

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Shauna Foster (00:06):
Winning is your guide to making it in business.
Join our award-winning host andentrepreneur, Mackenzie Kilshaw
, and special guests in casualconversations that will educate
and inspire you on your businessjourney.
Winning will help you learn thehard lessons the easy way, with
guidance from celebratedentrepreneurs and business

(00:26):
leaders.
It's fun, it's informative,it's winning.

Mackenzie Kilshaw (00:31):
Hello, welcome to Winning.
I'm your host, MackenzieKilshaw, and today's guest is
Dre Baldwin.
Hi, Dre.

Dre Baldwin (00:37):
Hey Mackenzie, how are you?

Mackenzie Kilshaw (00:38):
I'm really good.
How are you?

Dre Baldwin (00:40):
Excellent.
Thank you for having me on.

Mackenzie Kilshaw (00:41):
Yeah, it's really great to have you on.
Dre is the CEO and founder ofWork on your Game Inc.
He has given four TEDx talks ondiscipline, confidence, mental
toughness and personalinitiative.
He's also authored 33 books.
He's appeared in nationalcampaigns like Nike, Wendy's,
Gatorade, Buick, Wilson Sportshuge, huge campaigns.

(01:03):
He has published over 8,000videos and his content has been
viewed over 100 million times,which is amazing.
Dre also has a podcast, Work onyour Game.
It's a daily podcast where hehas over 7 million downloads.
So, Dre, I'm really excited totalk to you today and talk a
little bit more about working onyour game.
So, thanks for being here.

(01:23):
Do you want to tell theaudience a little bit more of
who you are and what is Work onyour Game?

Dre Baldwin (01:32):
Sure.
So everything you said in thebackground hopefully I can live
up to in your introduction there.
I grew up in the city ofPhiladelphia, now based in Miami
, always played sports growingup, got into basketball pretty
late around age 14, was as lateif you're trying to go play in
college or let alone playing inpros.
I only played one-year highschool ball, walked on to play
Division III college ball.
I had to hustle my way into probasketball, which I was able to

(01:54):
do, luckily, and at the sametime started publishing to this
brand new platform calledYouTube, and that's where I
started to build the name formyself online, and it was mostly
just the basketball players.
But after a few years theplayers started asking questions
about my approach because theyjust saw I was really consistent
, and this is way beforeconsistently publishing online
was a thing, and they startedasking about mindset.
So I started talking about itand people who were not athletes

(02:17):
started hearing the videosabout mindset and saying, Dre,
this stuff applies to everybody,this doesn't just apply to
sports.
So that's how I knew what mysegue would be from the sports
world to an audience of peoplewho were not athletes, and
that's exactly what I did in2015 when I stopped playing, and
that's pretty much what I'vebeen doing full time ever since.
So my company now, as you said,is Work On Your Game, and what

(02:38):
we do here is we take the toolsto help athletes reach the top
of the sports world and we applythose tools to the business
world to help professionals format their highest level, do so
consistently and, of course,make money.

Mackenzie Kilshaw (02:49):
Yeah, I love that and really, if you're
looking at it, the sports worldand the business world are
actually quite similar, right.
It is a lot of hard work,dedication, having the right
mindset to get you really whereyou want to go, and they do
correlate a lot, so it's reallycool that you went from sports
to the business world also.

Dre Baldwin (03:09):
Yes, thank you.
Yeah, yeah, there's a lot ofconnections.

Mackenzie Kilshaw (03:13):
Yeah for sure .
So you started out with sports.
I know, like you said, youdidn't start till a little bit
later, kind of an early teenager.
Did you always want to be abasketball player.
How did that?
How did that start?
What was when you were younger?
What did you want to do?
How did it grow from there?

Dre Baldwin (03:30):
I just wanted to be someone who was known.
I want people to know who I was, and I think athletics was the
vehicle.
Simply because I was.
I always had the athletic gene,so I was always playing sports.
You know a little bit offootball, a little bit of, you
know, touch football, notserious football, kickball,
backyard basketball, that kindof stuff.
You know running, you knowjumping over stuff, those kind

(03:53):
of things.
I knew I was athletic.
I was at least more athleticthan most of the kids on my
block.
But you know what, do you know?
You're just in that small spaceand I tried a bunch of sports.
You know, tried football, neverreally played football, did a
little bit of baseball wasn'treally that good.
So basketball was the sport.
That was just a naturalprogression.
Just where I'm from, everybodyplays basketball.
Because you don't needequipment no, it doesn't cost

(04:15):
anything to play basketball youjust show up and you have one
ball and a bunch of people.
You have a game.
That's how I just naturallygravitated towards basketball,
because that's what washappening in my environment.
And luckily I was no tall, longarms, I can run and I can jump.
You know I'm black, so thatmust mean I'm good at basketball
.
All right.
So then I just I kept playingand practicing by myself.
I wasn't good when I firststarted, but I got good because

(04:38):
I just kept practicing on my own.
Good thing about basketball isyou can practice by yourself.
So I just kept practicing on myown at the local playground and
the afternoons in thesummertime when it was too hot
for everybody else, and so I hadsome space to myself where I
could actually practice.
I had a little sandbox forbasketball, I guess you can say.
And that's how I did it.
So to answer your question, wasit my vision to become a

(04:59):
basketball player?
Not, at first, my vision wasjust to become known somehow.
And then, because I wasathletic, I figured it would be
through sports, but I didn'tknow which sport.
And then finally, once I got tobasketball and no, when I
started off I wasn't good.
But as I continued to practiceand I got better, I started to
think, well, maybe this couldactually happen and luckily, in
some ways it did.

(05:19):
I mean, it's not like I can'tgo to the grocery store by
myself, I'm not that famous, butI did make it as a basketball
player.

Mackenzie Kilshaw (05:26):
Yeah, for sure.
Yeah, you played pro and youplayed in eight different
countries, and overseas too.
So you, I mean you made it inthe eyes of making that your
career, for a point in time, forsure.

Dre Baldwin (05:39):
Yes, I did.
You're right about that.

Mackenzie Kilshaw (05:41):
Yeah, so you obviously practice is important
to you.
You've been talking about thata lot and how that helped you.
So when you went from yourprofessional career, were you
already, guess, working on workon your game, or was it just

(06:01):
something that you did in theory, or how did that business
aspect come from your basketball?

Dre Baldwin (06:08):
Yes, so start putting content online in 2005
and this was all basketballstuff and then around 2008 and
around 2009, 2011 and thistwo-year span, three years
conclusive.
This is inclusive.
This is where things started tochange, because in 2009, I
found myself unemployed frombasketball.
So, in other words, I was afree agent.

(06:29):
No, the phone wasn't ringing.
Yep, and I already had anaudience of people online.
I've been blogging as well asputting videos on YouTube, so I
had an audience online and theinternet was starting to become
we were, I guess we were in, Iguess, what they call web 2.0,
where you could basically putyourself out there and publish
yourself and blogs and your ownwebsites and sell stuff, and all
that stuff was starting tobecome a thing.

(06:50):
Yeah, I had an audience.
Phone wasn't ringing and I needto figure out what to do,
because I wanted a way tobasically have control over my
destiny, make money and stillhave something to do with
basketball, because if the phonedoesn't ring again, then I need
something to do.
So I had just finished.
Well, years earlier I had readRich Dad, poor Dad by Robert
Kiyosaki, and that was throughjust a random connection.

(07:12):
I got in the network marketingwhich I didn't build a business
in, but that experience openedme up to some new things like
personal development and bookson business.
So he talked about havingassets, how assets can put money
in your pocket and you don'thave to be your only asset by
just working and making money.
Because even though being anathlete is a job that most
people will see as a dream joband it is, at the same time, it

(07:34):
can see, when you're an athleteis still job.
You only get paid when you'reworking and if you're not
working like I wasn't at thetime You're not making any money
.
So assets, so how do I createassets?
So I had kept that idea in theback of my mind.
So now I just finished readingthe new version of risk dad,
poor dad for the digital age.
It was called the Four HourWork Week by Tim Ferriss also

(07:55):
great, yeah, right.
So Tim was just talking about alot of similar things not in
exact same vein, but a lot ofsimilar things just using the
internet for it.
So how can you outsource andhire somebody in India to work
for you?
I never thought of that beforeor how can you, again, be more
efficient in doing your workthrough using the tools of the
internet?
At the time, which was again2008, 2009 so he had a blog a

(08:20):
very popular blog at the time,still popular where he talked
about if you have an audience,or even if you don't.
Actually, he said if you havean idea and you want to create a
product and sell it online,here's what you do.
He had this little, basicallylittle process of what you do.
I followed the process becauseat this point, I needed
something.
So, as they say, necessitiesand mother of urgency all right,
you get urgent when you havenecessity.

(08:40):
So I start following his littleexperiment and I created a
little training program forbasketball players, because I
already had an audience of ballplayers.
I knew that I could help themby showing them how to practice.
So why don't I make a productout of showing people how to
practice?
Okay, so I created two productsfour dollars and ninety nine
cents apiece one for your moneyor one for shooting and I put
them on this little one-pagewebsite on a free hosting

(09:02):
platform.
I was just following Tim'sformat, his formula, and I went
to Google AdWords and I boughtfive dollars worth of ads for
like whatever keyword basketballtraining or basketball
practicing, something like thatand Tim said run ads and just
send the traffic to yourone-page website and then have

(09:23):
your product, whatever is called, have a little description of
the product and then put abutton that says buy this
product for and puts your price.
So I had that by this productfor four dollars and ninety nine
cents.
When people click on the button, it takes them to another page
that says this product is stillunder construction, but if you
want it, just put your emailaddress in and when it's ready
will email you.
And Tim said if you get peoplecoming from Google, again they

(09:45):
don't know you.
So there's not your grandmadoing it to be nice.
Yeah, people coming from Googlewho put their email address in.
That means you have a viableproduct, go make it and sell it.
So it's a those people there's,those are your customers right
there.
Yeah, and I did this and peoplewere putting their email
I want to give a disclaimer herefor those who are listening to
this in 2024 you can't do thiswith five dollars.

(10:05):
Today you probably need 50.
All right, but back then you go, five dollars, you probably
need 500.
If it's basketball, it's a verycompetitive keyword.
But anyway, I did this andpeople start putting your email
addresses in and, mind you, Istill had an audience online.
I didn't tell them about thisyet because those were my warm
audience.
You had to deal with a coldaudience.
So I made the product, put avideo up on YouTube, say, hey, I

(10:26):
have, this new product is overhere at this website.
People started buying itimmediately the first day I made
sales and I remember when I mylittle Blackberry at the time,
the little light blinked andsaid congratulations, you made a
sale for four dollars and 99cents.
When I made that sale,Mackenzie, I said to myself I
could do this for the rest of mylife, because what I had done
was created what we all know nowas intellectual property.

(10:49):
At the time I was not familiarwith that term and it was
basically taking an idea,packaging it up, putting a label
on it, putting a price on itand exchanging it for money.
That's what I just did and Isaid I got a million ideas, only
off one I got a whole bunch ofmoney.
So if I can pack as these allup and sell them and make money

(11:09):
from it, then I got a business.
I got a business opportunityright here in front of me and I
knew I couldn't play basketballforever and even if the phone
does ring again eventually, yourshelf life as an athlete,
athletic careers, are very short, so luckily, the phone did ring
again.
I kept playing till 2015, but,answering your question here, I
was an entrepreneur officiallyas of that day when I made my

(11:29):
first four dollar and 99 centssale, because I created my own
product, put it out, sold it andcollected the money, and I just
made more products, first ofall for basketball.
At this time and again I toldyou this is about a three-year
span at this time,self-publishing also became
ubiquitous.
So I started writing books,because I've always been a
writer, always been a blogging.
Then I started writing books,then I started creating courses.

(11:50):
So I had those three thingsgoing from 2009 through 2015.
So when I stopped playing in2015, I already had a runway of
an audience.
I had a framework, I had ideasand I had products.
So I already had these thingsin place when I stopped playing
basketball.
So it's not like I woke up thenext day like, okay, now, what

(12:10):
do I do.
I already knew what I was gonnado, because I was already doing
it.

Mackenzie Kilshaw (12:14):
Yeah, that's an awesome story and just built
from there.
I mean, now we're almost 10years later and you've got
podcasts, you've got you know somany things 33 books.
All of this is built on oneitem that you didn't even have
completed yet and you're alreadyselling it.
That's amazing.

Dre Baldwin (12:31):
Oh, thank you.

Mackenzie Kilshaw (12:32):
Yeah, when you got that first blink on your
Blackberry, were you like holycrap, like I made it.
Or were you like like I canjust imagine the excitement of
something because you werefollowing what the book told you
to do.
But when you get that firstkind of customer, first sale,
must have been really exciting.

Dre Baldwin (12:53):
Well, I didn't say a holy crap, I made it because
it was only $4.99, but I was, Iwas I would say I was satisfied
is the word that I would usebecause I already knew that I
had an audience.
So this was not.
It was not a guess as towhether or not I could sell the
product, because I was alreadyposting videos on YouTube for

(13:14):
four or five years by that point.
So I already knew there werepeople who wanted exactly what I
was selling.
So it wasn't a surprise thatsomebody will buy it.
It was satisfaction in that.
Okay, Tim laid out this plan, Ifollowed it, I did everything he
said and there are people whoactually will buy this and they
were buying.
So I was just satisfied withthat.
And now the first thing I'mthinking is okay, how can I so

(13:38):
enough of these programs towhere, if I don't get another
phone call to play basketball,it doesn't matter.
So that's what I was thinkingabout.
So I'm gonna make enough ofthese so that I can know, keep
my phone turned on, know thebills paid, know the rent paid,
etc.
That's what I was thinking likedo I need to make more of these
programs?
And answer was probably yes,because once somebody buys one,
well, now they need somethingelse to buy.

(13:59):
I thought what's the nextprogram?
So now I started thinking aboutall the stuff that I had made
on YouTube, all the differentthings I had taught.
I said, alright, how many ofthese programs can I create?
I got a mass produce thesebecause I need to have so many
that I could sell the sameperson 50 programs.
Yeah, that's what I was thinkingand my mind you, this is not.
There's no Chat GPT at thispoint.
I had to manually do this, allright.

(14:20):
So that's what I startedthinking of how do I do this to
where I can make a true fullfledged business out of this?
And at that time I didn't evenknow what auto delivery was,
which means if somebody bought adigital product from me, I had
to email them manually andinclude attachments of the
product.
I didn't even know was a suchthing as auto delivery, so so

(14:40):
that everyone know how far we'vecome in 15 years.
So after about a week of thisemailing, every person hit the
product.
I wrote I thought there has tobe a faster way to do this and I
found auto delivery.
So we fix that up prettyquickly.

Mackenzie Kilshaw (14:54):
Yeah, well, that's the thing, though, when
you're stepping into a newbusiness really it was a
business for you that you're notsure that's kind of stuff
happens.
You probably didn't even thinkabout it, and then at first it's
oh, I'll just email it, no bigdeal.
But then all of a sudden, youhave so much volume coming in
that you're just spending yourtime emailing right emailing
attachments.
So definitely, automating thatwas was a great thing for you.

Dre Baldwin (15:18):
Yes.

Mackenzie Kilshaw (15:20):
Your time is better spent not sending emails
with attachments, that's forsure.

Dre Baldwin (15:23):
That's right.

Mackenzie Kilshaw (15:25):
So let's talk a little bit more about Work On
Your Game and maybe, if youwant to speak a little bit first
on the transition of, you werevery basketball focused.
Yes, but, then you becamebusiness focused, so do you want
to yeah, just talk a little bitabout work on your game and,

(15:46):
and what is it all about?
And how did you make thattransition to the business side
of things?

Dre Baldwin (15:52):
Sure.
So remember, going back in thestory was that I got introduced
to what turned out to be networkmarketing when I was in college
and they?
The first thing is that inthose meetings, the speaker
would just spend a lot of timejust breaking down a lot of
people's most of the audience isfalse beliefs about how do you
make money, what are youroptions when it comes to

(16:12):
increasing your income, becauseeverybody was there because they
wanted to make more money noteverybody, but most of us and
the things that he was sayingfrom the stage were not being
taught to me in my collegelecture halls, and I have a
four-year business degree, sowhy are they not teaching this
stuff in schools?
I didn't understand it then,but I understand it now, why
they weren't teaching it.
And then the other thing was hesaid if you want to build a

(16:36):
business, you have to buildyourself, so make sure you go by
the personal development books.
And those are things that I'venever heard before, but they
made perfect sense.
So when I read Kiyosaki, thatplanted the seed in my mind for
being an entrepreneur, I knew Iwanted to be an entrepreneur.
This was a matter of how andwhat I was gonna do so.
The thing about the programsthat I was selling those
basketball programs was I wasnot running ads.

(16:56):
I didn't know how to run ads.
I only did the Google ad wordsthing, based on what Tim said,
but I didn't keep running ads.
I only did that for theexperiment and the only
marketing I would do to sell myprograms was just put more
videos on social media.
That's how I was selling myprograms just put a video on
social media, put a link to thewebsite and people are buying
them and and then YouTube atsome point changed their
algorithm that to stop peoplelike me from using them as a

(17:18):
resource.
Yeah, the thing is, as I keptdoing things business wise and
the audience that I had couldsee that I was doing business
things, even though it was usingbasketball as the vehicle, a
lot of them started to say, wow,I see, I see you're doing your
like your business things rightand I started doing more.
I was doing brand deals with alot of big companies at that

(17:40):
time based on my influence inthe basketball space.
But at the same time, I couldsee the writing on the wall like
I wasn't gonna play basketballforever and only thing that was
making me popular and helpingthose programs sell was that I
was putting out Basketballvideos every day.
Well, what happens when I stopputting out basketball videos
every day?
So I was thinking about thatalready.
So that's why, when I noticedthat there was an audience of

(18:00):
people who were not basketballplayers, who liked my stuff, I
said why don't I find a way toserve them as well?
Because I also understood thatmy audience when I first started
Mackenzie were 13 to mostly 13to 21 year old males and they're
trying to play basketball,hopefully for a living.
And one thing you have tounderstand about that audience
is that they're trying to playbasketball for a living, which

(18:22):
means they don't have any money,which means not much you can
sell to them.
I don't know if you can sell topeople who don't have money.
So five dollars was about theceiling and not the ceiling, but
you get my point.
I couldn't go high ticketselling to these people.

Mackenzie Kilshaw (18:35):
No, it's like $200, Right yeah right.

Dre Baldwin (18:39):
I wasn't thinking high ticket at the time, didn't
even know what that meant, but Iunderstood that there was a
limit to this and I would haveto sell a bulk of products in
order to make the kind of moneythat I wanted or needed to make.
So as people who were notathletes started coming into my
world, I realized, okay, there'sa whole other opportunity here.
So now, this wasn't somethingthat I just magically came up

(18:59):
with.
So about 2014, I knew I wantedto.
I was about to get out ofbasketball play till 2015.
I went to a Toast Mastersmeeting and in the speech that I
gave I just said hey, I'mgetting out of basketball, I
want to get into.
Next thing I was gonna do wasprofessional speaking.
The reason why this was my ideawas because around 2010, the
players again they were askingquestions about my mindset.

(19:20):
From just watching my videosand knowing my background, I
started doing these videoscalled the weekly motivation,
and the weekly motivation wasthis a little two to five minute
selfie video where I would justtalk about some mindset
principle, that just somethingthat I knew, something that I
thought was just common sense tomost people.
I realized very quickly that itwasn't common sense.
It wasn't the common knowledge,and I would just talk about

(19:43):
things like discipline andconfidence and mental toughness
and personal initiative, and Iwas using basketball kind of as
a canvas, but it wasn't aboutbasketball.
So people who didn't playbasketball started seeing those
videos and that's when theystarted reaching out and saying,
Dre, I don't even playbasketball, but that stuff
you're saying about mindsetapplies to me the way it applies

(20:03):
to others.
That's what told me that therewas an audience outside of the
sports room.
So in 2014, when I had went tothis, toast masters said I'm
about to get out of basketball.
There was another guy in theaudience who had played in the
NFL, and it was only about 10people in the room.
So this is just complete irony.
Yeah, he had played in the NFL.
I knew his name, but I didn'tknow his face because football

(20:25):
players wear helmets, so Ididn't know what he looked like.
But when he told me his name, Iknew who he was.
Yeah, he said well, look, I'mabout to retire from football
and I am about to go to thisconference where all the people
do their professional speakersand and what it was was a
National Speakers Associationconference.
I didn't know that at the time.
But he said I'm about to go tothis conference, I want to find
out what I need to know aboutthe speaking business and

(20:46):
anybody I meet, I'll just passtheir info to you.
I said, alright, I appreciateit.
He meant well, he gave me aninfo of one person and she was
already a full-time speaker.
She was author, she was in thethought leadership, she was
coaching, consulting, basicallyeverything that I wanted to do
she was already doing.
And when we connected I calledher and when we connected she

(21:07):
said well, look, I will help youlearn the ins and outs of the
speaking business if you help meunderstand how to get my name
known on the internet, becauseshe wasn't very known on the
internet but I was known on theinternet, so I'll help you with
this if you help me with that.
And that's exactly what we did.
And she taught me to ropes, tothe speaking business.
So she helped me understandthat, this whole thing that you
have, you got something goinghere.

(21:27):
You're an athlete, you havethis, these mindset pieces that
you talk about.
You've already written books,you already have an audience on
the internet.
So you're already.
You're a person who actuallydoes stuff you implement.
So I know, if I invest my timeinto you, you're actually going
to do what I tell you.
Because she said listen, ahundred people have come to me
asking the same thing I want tolearn to speak in business.

(21:47):
Then I tell them what to do.
They do nothing.
But you, I see that you'realready doing stuff, so I'm
betting that you're actuallygoing to do something if I tell
you what to do.
That's the only reason shedecided to meet with me, and and
on top of the fact that I couldhelp her with the internet.
So, so she started telling mestuff and everything she told me
I did it.
So she said that you might needto make some cold calls and try
to get yourself some somespeaking gigs.

(22:09):
Speak for free.
You need to get some proof thatyou can actually stand on the
stage and speak.
And I made cold calls and I didit, and I got on stages and I
spoke, and this is how I startedto get myself out there and
this is how I landed Ted Talkssame thing had to just go out
there and just pitch myself, andshe helped me understand that
you need a framework.
Okay, so the stuff you'retalking about is good, but you
got to organize it.
You have to organize it in away that when you call somebody

(22:31):
and say, hey, I'm, I'm, I wantto speak at your conference,
they're gonna say, well, what doyou speak about?
You need to answer and needs tobe concise and it needs to make
sense.
How does your experience as anathlete help them?
And they are a sales company.
What do you, what do you had todo with that?
And she helped me understandthat there's a way to organize
that.
The framework that became workon your game, so framework that

(22:52):
I had to this day, came fromthat conversation, those
conversations, and that's how Istarted to realize oh, I can
transition here.
And also when it came to thespeaking, the reason was for the
speaking was the last part,I'll give it to his answer.
Mackenzie was when I starteddoing the mindset videos, the
weekly motivation, the athleteswho were watching me and the non

(23:13):
athletes will leave comments onthe video and say, Dre, you
sound like a philosopher, yousound like a college professor,
you should be a professionalspeaker, the way you speak, the
way you explain things, becauseI just had this ability to
articulate.
You know, I've always had thatability, just communication
skill.
So that's what planted the seedin my mind okay, if I don't
play basketball, what can I do?
I can be a professional speaker.

(23:33):
And then when I met this woman,she was a professional speaker
and she was no charging people10, 15, 20 thousand dollars for
a speech.
I said, okay, well, if I canmake that kind of money now I'll
be a professional speaker.
So that's what got me off thefour dollar 99 cent programs and
on to let me see if I can getinto the speaking business
that's a really cool story.

Mackenzie Kilshaw (23:53):
I think, too, it shows a lot about, I mean,
you.
You diversified so much likethat.
It's a natural progression, butyou also had to take the steps
to get there and that also Ireally like the also the power
of networking there, because youwere literally at a
Toastmasters, I think yes, youmeet this guy, you connect with

(24:16):
him, he connects you to someone,but you do the work and that's
that's the glory of having anetwork of people, that someone
can help you and you helped herright.
So that was such a I meantotally changed where you were
going, but I think in all thegood ways.

Dre Baldwin (24:33):
Absolutely and in your 100% correct, and that the
fourth piece of my the workingyour game framework, as
originally created, was personalinitiative, which is going and
making things happen.
You can't sit around just waitfor the opportunity.
You have to go do stuff.
So I just went and did stuff somany different times that
Sometimes that's who'sserendipitous outcomes that.

(24:53):
I could not have planned.
I couldn't plan there'd be a.
I'm at a meeting with 10 peopleand an NFL player happens to be
there and he happens to beretiring and he happens to want
to be a professional speaker.
How does that happen?
Yeah, that's, that's just blindlook, but because I showed up,
it occurs.

Mackenzie Kilshaw (25:07):
That's right, yep, you showed up and you took
, you started talking to thatthe NFL player and you start
right and you're like, hey, ifyou go there you share great
it's, it's that whole dynamic ofbeing present and you could
have went to that meeting andnot talk to anyone and went home
and None of this might havehappened right.

Dre Baldwin (25:27):
Exactly.
But that's the reason why Iwent to the meeting, because
someone told me that atToastmasters you can learn how
to be a professional speaker.
They were actually wrong.
That's not what they do atToastmasters.
No, because I was there and Iannounced that I wanted to be a
professional speaker.
Someone heard that and theysaid well, hey, guess what, I
know something.

Mackenzie Kilshaw (25:43):
Yeah, that's awesome.
Do you still use basketball alot in what you talk about?

Dre Baldwin (25:49):
I use sports as a, sometimes I use sports as a
frame of reference, but one ofthe things, Mackenzie, is my
superpower is my ability tobreak things down and put them
back together.
It's the way I say it, and whatI mean by that is, even if you
have never picked up abasketball in your life, I can
use a basketball example or abasketball metaphor with an

(26:13):
audience of people who neverplayed ball and I can explain it
in a way that you'll understandit and understand why it
connects to what I'm saying,even if you know nothing about
basketball.
That's my superpower.

Mackenzie Kilshaw (26:23):
Yeah, definitely a talent.
Well, and, as you said, you'vealways enjoyed writing.
Clearly you've got greatcommunication skills.
I think it all goes hand inhand.
Plus, I'm assuming you lovebasketball still and you're not
playing anymore, but let's youstill talk about a sport that
you love and use that as an easyway for people to understand
something.

Dre Baldwin (26:41):
Yes, I can use it as a frame of reference, but I
don't need to.
So I just want to be clear.
I don't need to use basketball.
I can.
We have to have this wholeconversation?
I had to talk about basketballat all.
I can still give value.
So the material that I put outa lot of times I'm not bringing
up sports at all and again, if Ido bring up sports, you don't
need to be a sports player oreven a sports fan to understand

(27:03):
why I'm using it.
But the bottom line is neverabout sports, because I don't
play sports and, yeah, abusiness person, I'm an
entrepreneur.

Mackenzie Kilshaw (27:10):
Yeah, for sure.
It's just an easier way to getyour message across.
I guess when you use it some,when you talk about something
that's relatable for peopleright, it helps depending on who
you're talking to.

Dre Baldwin (27:22):
Now, what you're talking about, who's never
played sports?
Now it might be harder becausethey don't get it.
They don't know why your brainthat up.
So if I'm using the rightreference, it depends on the
reference, what I'm talkingabout, who I'm talking to.

Mackenzie Kilshaw (27:33):
Okay, I guess this is a great point.
Then, really, depending whoyou're talking to, you're gonna
change your message to make surethat it's appropriate for them.

Dre Baldwin (27:41):
Mm-hmm.

Mackenzie Kilshaw (27:42):
Awesome.
Okay, let's talk a little bitabout discipline and two kind of
points here.
Why is discipline such animportant aspect of success?
And also how does disciplinecreate confidence?

Dre Baldwin (27:58):
Well, disciplines an important aspect of success,
because it's all about showingup and doing your job on a
consistent basis.
And if anyone asked me, Dre,what's the number one asset that
you've used to get from whereyou were to where you are, an
answer is discipline.
Always, that is.
The most important assets forme personally, is discipline.
One reason is because, as youshow up consistently and do your

(28:18):
job, it helps build confidence,and most people want confidence
.
Most people need discipline,but they want confidence.
And also, because so few peoplehave discipline, it actually
allows you to stand out by thelaw of contrast.
Because so few, so few peoplehave discipline.
When you have it, you stand upfrom the crowd.
Because most people don't showup consistently, most people

(28:40):
don't follow through, mostpeople are not consistent.
So, when it comes to whydiscipline matters so much, and
what was the other half of thequestion, just how does
discipline create confidence?

Mackenzie Kilshaw (28:51):
I think you just kind of said it.

Dre Baldwin (28:52):
Yeah.
So this is when this onecreates confidence.
In that, confidence is definedas your belief in your ability
to do something, and that beliefcomes from the fact that you've
actually done it.
So confidence about lookinginto your past.
And you look into your past andyou see that you've done this
thing over and over and overagain, that you have afforded
your right to be confident.
You forward yourself the rightto be confident at it because
you've done it so many times.

(29:13):
So that's how disciplinecreates confidence.
And, again, as I said, mostpeople want confidence, but they
need discipline.
So a lot of times people shyaway from the things that they
need, but they go runningtowards things that they want.
The problem is, people golooking for the confidence they
want but they don't have itbecause they haven't laid the
ground right, they haven't paidthe price right.

(29:33):
You didn't.
You didn't pay for yourmembership.
You can't use the gym, allright.
So there's a metaphor for youright there.
So you have to actually do thework, because confidence is
literally a membership.
It's a membership in that onceyou become confident, you don't
just stay confident.
You have to keep doing thethings that led to you being
confident.
And if you stop doing them,then you lose your confidence
and that ability.

(29:53):
It's like if you stop, howoften do you record episodes for
the show?

Mackenzie Kilshaw (29:58):
Oh, once or twice a week.

Dre Baldwin (30:00):
Once or twice a week.
So if you went three months anddidn't record anything and then
you try to recording it, youprobably a little sloppy when
you came back right because youstop paying the price.
You lost the skill so it workswith.
That's how it applies anything.
That's the concept of atrophy.
You don't use something, youlose it.
The ability goes away if you'renot using it.
So the discipline of yourecording once or twice a week

(30:21):
makes you sharper and use getbetter time at the time, at the
time, the more you do it and youbecome more confident in doing
the thing because you're doingit so often.
But if you stop doing it, thenthe confidence goes away because
you are doing the work.
Now the challenge is you know inyour mind what it looks like to
be able to do it because you'vedone it so many times.
Let's say you go away for sixmonths and you know what it
looks like to be able to do itbecause you've been there.

(30:42):
But you can't do it right nowbecause you have not been paying
the price.
So you have to have thediscipline to work yourself back
up to that skill level that youwere at before to get sharp
again.
But you got to pay the price.
You got to start back at groundzero where you were.
You can get there fasterbecause you know the path.
Then you did the first time,but you still have to pay your
dues the same way than anybodyelse would I.

Mackenzie Kilshaw (31:03):
Love that and I think discipline is something
that, honestly, we don't reallytalk about enough.
But I could not agree with youmore.
It's so necessary and puttingin the time.
It doesn't matter what yourbusiness is.
You have to put in the timeright, because if you don't, you
can hope and wish that thatcomes, gonna be what it is, but
without the actual work you'renever gonna get there.

Dre Baldwin (31:25):
That's right.
You got to put in the work inanything and as much as know as
an entrepreneur.
I talk to people all the timeabout don't fall into the trap
of you know what they callhustle culture or a family, that
you have to go to bed late andyou got to wake up early and
team no sleep and all thesethings that people say about

(31:46):
just hustle, hustle, hustle.
Don't fall into that trap.
At the same time, hard workstill matters.
You still had to do the hardwork.
There's no shortcuts of hardwork.
Anything you want to besuccessful at, you have to work
hard.
The challenge is what are youworking hard on?
That's the real challenge.
Is not that there's a way toshortcut the, the mandate for

(32:09):
actually putting in hard workand effort and anything you want
to be successful.

Mackenzie Kilshaw (32:13):
Yep, I love that advice and it goes to
everything business, but I meanit goes to if you want to be a
doctor, you have to go to theseven years of medical school or
whatever.
To be a doctor you want to beright.
All of these, it doesn't matterif you're an entrepreneur or
small business owner or anotherprofession.
Putting in the work is going toget you there and that's the
only way.
I love how you said there's noshortcut to hard work, because

(32:33):
that's such a such a great wayto phrase it so simply, but it's
very true that's right mentaltoughness, too, is something you
talk a lot about, and thismight go back to discipline, but
do you want to just touch alittle bit more on mental
toughness and why it's necessaryin your business?

Dre Baldwin (32:53):
Sure business life the way we describe mental
toughness is your willingness toremain disciplined and
confident, despite the fact thatbeing disciplined and confident
up to this point has yet toproduce a desired result.
So, no matter how hard you work, how clear and clean your plans
are, how talented you are, howmuch you believe in yourself,
inevitably something's not goingto go the way you want it to go

(33:13):
.
Never be.
Something's just not going towork in life.
Somebody else may disappointyou.
You plan to picnic and israining outside now.
You did all the hard work andthings just don't go the way
that you expected.
This is inevitable.
It happens to everyone.
Knowing is immune to this mentaltoughness is your willingness
to stick to the plan, staypersistent and stay disciplined

(33:34):
and remain confident that youreffort will pay off, even though
it has yet to pay off.
And the reason why mentaltoughness matters so much,
Mackenzie, is because it becomesthe great differentiator
between the people who succeedand the people who fail.
And that many people quit whenthey haven't gotten the result
that they expected, especiallyif they feel like other people
know about it, because peopleare so afraid of ridicule and

(33:57):
criticism that they would rathernot try, then try and come up
short or especially if they'vealready tried and came up short
once, they don't want to letthat happen again.
So they rather do nothing, theyrather just quit.
And mental toughness is yourcompetitive advantage.
When you are willing to remainconsistent, you're willing to
stick to it, you're willing tohave the grit and the toughness

(34:20):
and want to grind it out,getting through the situations
that are less than ideal, sothat you can achieve your
desired outcome even thoughyou're not getting out, even
though things are not going theway you want them to go.

Mackenzie Kilshaw (34:32):
Okay, the last thing I really want to talk
about and you kind of talkedabout it a little bit already
but personal initiative and whythat's so important.
But I think for you, like yousaid before, when you started
with work in your game, you youkind of just went for it.

Dre Baldwin (34:49):
That's right.
Yeah, personal initiative.
And first place I heard thiswas in the Pomeo Hill and his
book thinking girl rich and forthe law of success, where that
book came from.
And he says that if you'regoing to be successful or I'll
say that I say this because Ibasically took his concept and
spread it into my own words isyou can't sit around and wait

(35:11):
for an opportunity to find you.
You have to go, create anopportunity.
You have to go and do somethingso that when I think about my
own story, how many times I hadto take initiative I had taken
this to just go practicebasketball and then take
initiative to try out for theteam when I got cut the first
three times.
And initiative to go walk on toplay in college, and this took
to try to play pro when no onewas asking me to play pro.

(35:32):
I get on the internet when itwasn't even a thing to be.
Publishing content on theinternet by creating a product,
offering it to the world, doingTim's little experiment to test
out and see if this works, toactually sell your $4.99
training program.
Talking about mindset in videosbecause a lot of people are
asking about it, realizing thatpeople who didn't play sports

(35:52):
wanted it, and not pigeonholingmyself in just the sports world.
I'm going to that toastmaster's meeting following what
my mentor was telling me to do,all of these things so many
times that I had to takeinitiative in order to be where
we are here today.
I mean, I don't know if youtold your audiences, but how
this conversation even happened.
All right, there was, there wasan initiative taken right.

(36:13):
So we, we are always looking toinitiate.
Initiative comes from the wordinitiate.
Initiate comes on word initial,initial means first.
You go, first you have to movefirst.
You can't sit around and waitfor someone to offer you the
opportunity.
Is great when it happens, butis even better when you go
create it, because now you knowyou can create another one.

(36:35):
That gives you confidence.
All right.
So all of these work togetherthe discipline of looking for
opportunities and trying toinitiate them when they start
working.
It gives you more confidencethat the next one can work and
the next one, and the next one.
And also you need to have themental toughness to understand
that if you reach out andsomething doesn't work, that's
okay, keep trying.
Next one, make the next call.
Someone doesn't buy at yourlast sales presentation, I'm

(36:58):
gonna make the next presentation.
All right.
When I play professional sports,people don't understand how
many teams that we reached outto that didn't respond or said
no, you only need one.
You're gonna pay for one thingat a time, right?
So it's not like everybody'sgonna say yes to you, even my
programs not everybody who sawthe programs, both them but we

(37:19):
sold enough in them, right?
So it's not about everybodysaying yes, is about you being
willing to take the initiativeand because so few people are
willing to take an initiative,again it becomes a competitive
advantage.
So all of these pieces that wetalked about discipline,
confidence, missile, toughens,personal initiative they're all
competitive advantages when youknow how to create them and you

(37:39):
have them on a consistent basis.
Because so few people have themconsistently, people can have
them every now and then.
So few people have themconsistently that if you can be
consistent in these is separateyou from everybody else.

Mackenzie Kilshaw (37:50):
I love that and I did not share how you
became a guest.
But I'm going to now becauseI'll be honest with you and I
didn't tell you this before Iwas blown away.
I reach out to lots of people,lots people reach out to me and
of course I always look to see,because usually you just get a
name, maybe a bio attached orcheck out the website.
But you actually sent me avideo and it was talking about

(38:16):
yourself, in a good way, but whyyou would be a good guest and
why my audience would like tohear this information, and it
was fantastic like I was blownaway by it.
So that was the best ever guestexperience that I've had to get
a guest on.
And but you did that right.

(38:36):
I didn't reach out to you.
You reach out to me with thatvideo and I watched it.
I was like, yeah, he's gotta beon.
So thank you for that.
That's just just shows whatpersonal press excuse me,
personal initiative does.
It works, so keep it up forsure.
I'm glad it worked yeah, I'mglad to work to do.
You have a most importantlesson that you can share with

(38:57):
the audience.

Dre Baldwin (38:59):
Yes, we're in a performance and results based
business.
I tell people that all the timeand it applies in the sports
world you absolutely have toperform and the result is on a
scoreboard.
You win or you lose, and youlose too often, you'll be out of
a job and in the business worldis the same thing.
You have to perform in yourbusiness and the result is you

(39:20):
get to choose the result.
But you can count your cash,you can count leads, you can
count conversion rate, you cancount how many people are
watching your show, whatever itis.
But there needs to be a clearlydefined result that you're
after and everyone is no thatand the performance is based on
producing that result.
And if you're not producing theresult for too long, you may
end up out of a business or youwill lose a lot of business.

(39:42):
So we're on a performance andresults based business.
You need to know everyonelistening what is the result
that you're after and what typeof performance is required in
order for that result to beachieved on a consistent basis.
People don't know that you do awhole lot of work is still not
get to your goal, so make surethat's clearly defined.

Mackenzie Kilshaw (40:00):
What is there anything you wish you had known
, or maybe wish you could havetold yourself in 2014, when
you're working on this?

Dre Baldwin (40:10):
Yes, man, so many things.
So, going back to when I put myfirst book out, which I knew
about building an email list,because I didn't have a list
when I first started, when I putmy first book, I probably
missed out on fifty thousandemail addresses that I could
have had on my list had I knownabout this building that's one.
Number two I wish I had knownabout just going high ticket in
terms of selling whatever it is,and I'm selling because it

(40:31):
takes the same amount of effortto sell something for twenty
grand that it takes to sell itfor two hundred dollars.
Say, my effort may not be tothe same person, but it takes a
month effort.
So I wish I had known that alot earlier.
So I'll just give you those two.

Mackenzie Kilshaw (40:44):
Those are perfect.
Thank you so much.
I'm people I know are gonnawant to know more about you.
Where can they find you?
Where's the best place for themto go to learn more?

Dre Baldwin (40:53):
Sure, you can go to all course.
You can find me on all thesocial media platforms, on every
single one, usually the namethere is just Dre Baldwin or
Work On Your Game, differentones with different platforms,
but I'm easy to findeverything's public.
I do have a book that I giveoff free to people.
Can I share that?

Mackenzie Kilshaw (41:09):
Yeah, of course yes.

Dre Baldwin (41:11):
My book, The Third Day, what's ahead right here for
those watching on video.
This book is all about how youshow up and give your best
effort when you feel like.
That's what discipline is about.
So this is one of the mainframework.
So you explain discipline.
So that day when you realizethat the thing you signed up for
is not one big party, thenovelty is worn off, the newness

(41:31):
is worn off, but you still haveto show up and do your job and
is all on you.
That is called the third day,and this book is about the
decision that you make on thatday is not about that day
happening, because happens.
Everybody is about the decisionthat you make and your decision
is unique and unique to you.
So the decision you makedetermines whether you're gonna
be a pro or an amateur.
And a professional person doessomething is a main paid

(41:52):
occupation.
Only way you can get paidconsistently is you have to show
up consistently, even when youdon't feel like it.
That's what this book is about.
Is about structuring andsystematizing showing up even
when you don't feel like showingup.
www.
t Third day book.
com.
The book is free.
You cover the shipping.

Mackenzie Kilshaw (42:10):
I love that.
I think I'll be going on tothat site shortly after record
this drink.
Thank you so much.
I really appreciate it.
You're a great guest andeverybody listening will see you
on the next episode.
Thanks for listening to Winning.
Be sure to subscribe to get allof our new episodes.
If you enjoyed this episode andyou'd like to help support the
podcast, please share it withothers, post about on social

(42:33):
media and leave a rating andreview wherever you listen to it
.
To catch all of the latest fromus, you can follow Winning
Podcast on Instagram @winning_podcast, Facebook @Winning
Podcast and on Twitter @winningpod.
Winning was created and isproduced by me, Mackenzie

(42:53):
Kilshaw music, created by SummerFirby, editing by Seth
Armstrong.
Special thanks to Shauna Fosterfor voicing our opening and, of
course, a huge thank you tothis episode's guest.
Thanks again for listening andI'll see you on the next episode
.
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