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April 9, 2025 31 mins

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Developing a trusted "Number Two" in your business isn't just smart strategy—it's biblical stewardship at its core. In this illuminating episode, Harold Milby provides a comprehensive roadmap for identifying, developing, and empowering your successor with godly wisdom guiding every step.

The journey begins with finding someone who possesses both character and capability. While competence matters, qualities like integrity, humility, and trustworthiness form the foundation of effective Christian leadership. Harold shares practical assessment methods to evaluate potential candidates, along with critical pitfalls to avoid—like selecting someone too similar to yourself or overlooking quieter achievers who might be diamonds in the rough.

Drawing from his own extensive experience as a Number Two leader for over two decades, Harold offers unusually candid insights into this vital relationship. His personal stories reveal how being stretched beyond his comfort zone by a mentor who believed in him created profound growth opportunities—a pattern you can replicate with your own emerging leaders.

The episode weaves together practical business wisdom with spiritual guidance, examining the biblical model of Moses and Joshua as the ultimate example of godly succession planning. Through intentional mentoring, progressive responsibility, and public affirmation, Moses prepared Joshua to lead with confidence and divine purpose—a pattern every Christian business leader should consider.

Whether you're currently searching for your organizational second-in-command or looking to strengthen your existing leadership pipeline, this episode provides the framework you need to honor God while ensuring your business thrives beyond your tenure. Discover how developing others becomes an act of faith that extends your impact far beyond what you could accomplish alone.

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Episode Transcript

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Speaker 1 (00:03):
Welcome to the Christian Business Concepts with
your host, harold Milby.
Christian Business Concepts isdedicated to guiding companies
and business owners in becomingeffective, efficient and
successful through God's Wordand godly principles.
Now, here's your host, haroldMilby.

Speaker 2 (00:19):
Thank you, kelly, and welcome everyone to this week's
Christian Business Conceptspodcast.
I'm your host, harold Milby,and each week I try to discuss
topics and biblical principlesthat, when you apply them, I
think will help you find truegodly success.
And today it's my prayer thatthis podcast encourages you,

(00:41):
that it empowers you andenlightens you as you listen.
Now, this week, I'd like togive a big shout out to Sherman
Texas, right here in the UnitedStates.
We appreciate all of you therein Sherman Texas who have
downloaded so many podcastepisodes, and we are just hoping

(01:01):
that will be a blessing to you,as we do with all of you who
download these podcasts aroundthe world each week.
We're so thankful.
We're thankful to the Lord foreach and every one of you.
We hope you'll just continue tohelp us to reach our goal of
reaching over 1 million peoplewith this message of a godly
success through applying thesebusiness biblical principles, of

(01:25):
a godly success throughapplying these business biblical
principles In our companyspotlight.
This week, I want to talk aboutForever 21.
Forever 21, it's a fashionretailer that was founded in
1984 by a husband and wife team,actually Do Won Chang and Jen

(01:47):
Suk Chang.
Their Christian faith hasalways guided their approach to
running their company, forever21.
And in an interview recentlywith CNN, do Won Chang expressed
his desire and their desire toshare the love of God with their
customers and their employees,and that really reflects their

(02:11):
intention.
They've got an intention tolead with a really faith-based
perspective and that's theirdesire desire.
Their deep commitment to theirrelationship with God is not
only really reflected in theirbusiness and in their work with
their employees and their carefor their employees, but even in

(02:33):
their charitable giving.
They give them to a lot ofcharities and they're really
trying to help those charities.
But they also put scriptures onthe bottom of their shopping
bags.
So you know they're trying tolive out their faith.
They're a great example of whata Christian business ought to
be.
So remember that name, forever21, and we hope that you'll

(02:57):
participate in visiting theirstores and buying from them, and
we want to support them as aChristian business.
That's what this is about andthat's what our podcast is about
.
So, as a Christian businessleader, you're called to not
only have that business andstart and run that business, but

(03:20):
you're called to steward thepeople and the resources that
God has really kind of entrustedyou with, and part of that
stewardship involves preparingthe next generation of leaders,
and so I want to talk today alittle bit about raising up a
number two person.

(03:40):
This is a trusted person whocan share your responsibilities
and, if really needed, they canstep into your role.
You know, today I'm going toshare kind of a step-by-step
guide, first to identifying whothat person may be and then
developing them, empowering themand preparing them to be a

(04:02):
number two.
All the whole.
While that you're doing this,you're also seeking God's
counsel and aligning with thosebiblical values.
You know, I spent a long part ofmy career as a number two.
That's kind of what I felt likeI was called to.
So I came alongside and I didthis for one person for a long

(04:27):
time and was his number two andactually enjoyed that more than
anything I've ever enjoyed in mylife, to be honest.
And this person he had morethan one number two.
He had about three of us and wewere his number two person and
he came to each one of usdifferently for different things

(04:48):
.
You know, throughout thoseyears and you know I just took
that opportunity to learn, togrow, to stretch, to be
stretched.
He was really good at that, andI think that's part of what you
do.
And so in today's dynamicbusiness landscape, we'll say
you know, leaders are.
Often, you know, you getconsumed by just the daily

(05:10):
operations.
It can really cause you toneglect a vital responsibility,
and that's developing thesefuture leaders.
You know, a number two personis not just a backup, but
they're really a strategic assetthat's essential for your

(05:34):
organizational success.
I believe that this individualshould step in during, maybe, a
crisis.
They're there to support thatcritical decision-making and
ensure continuity duringleadership transitions.
That's something that's alsovery important, and research

(05:56):
from the Harvard Business Reviewindicates that only 30% just
think about that.
Only 30% of organizations feelconfident in their leadership
pipeline.
You know, which really kind ofhighlights this urgency that I
think we need to have for aproactive approach to developing

(06:18):
a really capable number two.
You know Richard Branson, who'sthe founder of Virgin Airlines
and Virgin Group.
He said one time he said thebest leaders know their success
depends on surroundingthemselves with people who are
smarter, more capable and readyto step up.

(06:41):
A strong number two isessential for that.
So I believe that most of yourgreat leaders and great business
operators understand theimportance of having a strong
number two.
They deliver significantbenefits to both the leader and
the organization.

(07:01):
So a good number two will giveyou that operational support.
It really frees up your time tofocus on strategic priorities.
You know, when you've got agood number two they could do a
lot of the strategic operationalthings that need to be done and
that kind of gives you thatopportunity to really focus on

(07:24):
the vision and through thestrategies that you need to have
in the business.
Uh, it gives you a lot of goodperspectives.
Uh, it really uh, uh, uhcreates uh team morale.
Uh, you get that because, uh,you know it.
It kind of lets people see thatyou have a commitment uh to

(07:45):
growth, to personal growth anddevelopment of people within the
organization.
And then it also gives you thisorganizational resilience
because it provides stabilityand continuity during, you know,
a planned either a planned oreven an unexpected transition.

(08:05):
So you've got to identify thisright person.
That's the first thing that'sgot to happen.
You've got to identify thisright person.
That's the first thing that'sgot to happen.
You've got to identify who theyare, you know, and choosing
this right person uh is acritical decision, uh, and, and
this individual will play apivotal role in your
organization and may one dayeven lead the organization.
So the selection is veryimportant and it requires prayer

(08:28):
and discernment and a focus onboth character and capability.
So here are some of thequalities that you need to look
for for a number two.
When you're identifying thispotential person, you need to
seek individuals who exhibitthese kind of qualities I'm
going to share with you.
So, first of all, you need tolook for a person with integrity

(08:50):
, honesty and ethical behaviorand a strong moral foundation.
That's very key, according toProverbs 10 and 9.
And then there's humility.
You know you've got to have awillingness.
This person needs to have awillingness to learn.
They've got to have awillingness to serve other
people and prioritize themission that you have for their

(09:15):
organization over their personal, what their personal gains may
be or personal desires may be.
So you've got to have humility.
And there's companies that I'veworked for that that's the key.
That's one of the things thatthey look for.
There's a lot of people theyhave passed on, you know, even
though they've been maybe abetter person than their number

(09:38):
two is.
But because the number two ismore of a humble person, they
fit their culture and theircompany a little bit better.
So that's important.
But you want to look forcompetence.
You know they've got to becompetent.
Of course they've got to havethe skills and the knowledge and
experience that are needed toperform well.

(09:59):
And you know that's really what1 Timothy, 3 and 10 says
Loyalty.
You know you've got to have acommitment to an
organizational's values andvisions, with a, with a really.
You know your desire as anumber two person would be to to
have a, a just a really similarvision or a willingness to back

(10:26):
up the vision of the leadershipthere.
And then you need to look forleadership potential.
They've got to have thispotential.
They may not step into thatrole right off the bat as the
number two.
You may have to groom them, youmay have to prepare them, but
you've got to look for thatleadership potential.

(10:46):
And then you've got to have atrustworthiness.
There needs to be alignmentwith your company values.
That's got to be important andthat's got to be there.
And they've got to have acertain amount of strategic
thinking.
They've got to be able to lookat things through a strategic
mind and make decisions andthings strategically.

(11:10):
You've got to see that bigpicture.
They've got to see that, andthey've got to make decisions
with more of a long-term type ofvision that they have when they
make those decisions.
They've got to have a long-termimpact when they make those
strategic decisions.

(11:31):
And next would be theadaptability.
That's something you need tolook for.
Look for somebody that'sadaptable.
They're flexible, they canreally thrive in a changing
environment, and then they canembrace new challenges.
So then, if you find thesequalities in a person, you've
got to assess those qualities.

(11:52):
You have to look at them.
How deep are they?
How much in depth are they inthese qualities?
You can use a lot of differentmethods when you evaluate
candidates, but I find thatthese are the ones that you want
to use.
So, first of all, observation,so you can watch a person and
watch how they handle challenges, watch how they interact with

(12:15):
others and watch how theyapproach their work.
I've always said, you know,there's two types of people that
work.
There's those who lean intotheir job and those who lean out
, and what I mean by that is,those who lean in are always
aggressive in their work andthey're always looking for ways
that they can accomplish theirwork, whereas somebody who leans

(12:36):
out is always looking for waysnot to do their work, and so you
want to look for somebody thatleans in so you can observe this
person for a period of timeMaybe there's multiple people
that you're watching and thenyou want to get feedback.
That's the next way that youcan assess these qualities, so
you can gather a lot of insightsfrom people they work with with

(12:58):
supervisors, with team membersand talk about their character.
You know kind of talk abouttheir performance there's
nothing wrong with that and thenget feedback.
And then next look at theirperformance reviews.
Your company should be doingperformance reviews.
If they're not, they should be.
So look at their pastachievements, look at how

(13:19):
they've grown, and then you canassess their consistency and
potential.
If you've got somebody that hasa positive performance review
this year but the next two yearsthey don't and then the next
year they do, then you may wantto take a pass on that person
because you're looking forconsistency.

(13:39):
And then another way you canassess these things is to
actually interview them.
Just sit down and talk to them,tell them what you're looking
for and then discuss what theirgoals are, discuss their values
and discuss what their vision isand make sure they align, make
sure they line up with yours,with your organization's mission

(14:00):
.
That's important and thenincrease responsibilities.
You've got to test theircapabilities and you know my
boss that I spent 23 years or 21years with, I should say he was
a master at stretching people.
There were so many times thatwhen he would come to me with

(14:22):
something, I would think tomyself as I walked out of his
office you know, I can't do this, I don't think I can make this
work, I don't think I can do it.
But he had a lot of confidencein me and he challenged me a lot
to do things and it reallystretched me.
It really helped me to enhancemy abilities, increase my
abilities and my knowledge, andthat's what you want to be able

(14:46):
to do.
So you can do that with themand you can help them by
increasing theirresponsibilities.
And so those are some of thethings that you can do to
evaluate them.
And you know there's severalpitfalls that you have to look
for when you're doing a numbertwo and you've got these are
mistakes that you just have tolook for.

(15:07):
So make sure, number one, thatyou select you don't select
someone that's just like you.
You know that's going to createsome blind spots in your
leadership.
You want to find people thatare not like you.
You know you're like you, right?
So you don't need to have amimic or have a mini me, if you

(15:28):
will.
What you want to do is findpeople who are different, have
different perspectives, havedifferent experiences.
You want somebody differentthan you so you can have a
well-rounded leadership team.
So find somebody that's notlike you.
Another mistake that we make isoverlooking quieter people,

(15:49):
people that are a little bitmore quiet, and what we do is we
go to the people that are morevocal, that they're more visible
employees.
A lot of times, there's a lotof gems out there, there's some
really gold out there in yourfactories or in your companies,
in your organizations, or maybenot in your organization, but

(16:12):
they're the quiet person.
They're not the one thateverybody knows and hears, but
they're the ones that get thingsdone.
So don't overlook those type ofachievers and go after the
people only that are vocal andvisible and then ignoring
diversity.
That's going to limit yourinnovation.
It's going to limit those freshperspectives.

(16:33):
So you want diversity and thenthe last thing you have to watch
as a pitfall is rushing thatdecision.
You don't need to rush thedecision.
If you don't have a number tworight now, it's not going to
hurt anything to wait monthslater to find the right person.
Don't rush into it.
Take your time.
Take your time, read James 1and 5.

(16:55):
That'll give you a goodperspective on that.
So now you've identified themand you've picked them, and you
have that number two, how do youdevelop them?
How do you spend time and youdevelop this person once you've
identified them?
Because development is aboutbuilding their skills.
It's about shaping theircharacter and deepening their

(17:20):
faith and preparing them to leadwith confidence and with
godliness.
Those are important factors,especially when we're talking
now.
We're talking about Christianbusinesses.
So one of the things that you dois you mentor them.
That's going to be thefoundation for their development
.
You want to be a mentor to thatperson.

(17:41):
You need to have regularone-on-one meetings so that you
can give them guidance andsupport.
Now, the person that I workedfor used to come into my office
every morning.
He'd come into my office everymorning.
We'd have short you know littleshort meetings.
Sometimes they were 15 minutes,sometimes they were 45 minutes,
and we'd talk about a lot ofthings.
We talked about personal things, but we would talk about work

(18:05):
things.
He would challenge me, he wouldask me how I was going to
handle certain situations.
He would give his support orhis input.
But you want to mentor thatperson, so hold regular meetings
.
And then you want to share yourexperiences, share your
successes.
Now, when you do that, don'tjust share successes, you want

(18:26):
to share your failures too,because we all learn through
failure.
We probably learn more throughfailure than we do through
success.
And so you want to be able toshare your failures with that
person so that you can give themsome really practical wisdom.
And then you want to encouragethem to seek God's direction as
they go through this journeydirection as they go through

(18:53):
this journey.
You want them to view theirrole as really a calling.
You can read Colossians 3, 23through 24 on that.
But I can tell you from my ownexperience, I felt like being
that number two was a calling.
It was a calling on my life.
That's what I knew I wassupposed to be doing and that's
what I did.
And I think that it's importantthat you understand that it is

(19:14):
a calling, or that theyunderstand it is a calling.
So the next thing that you do,besides mentoring, is you do
training.
So you've got to support them.
You've got to support theirgrowth, and you can do that
either through formal educationyou can recommend courses or
certifications that are relevantto what they're doing.

(19:34):
You can send them to workshopsand you can send them to
conferences.
Give them some good access tothese kinds of leadership events
and especially if you can findthose that are integrating faith
with business I think that'skey.
And then, provide readingmaterials.

(19:55):
You know the one company that Iworked for.
You know they had a wholelibrary and so they provided
great material, reading material, a lot of books, but I would
throw in there also devotionals,anything else that would help
build both their professionaland their spiritual maturity.
I think that's important.

(20:18):
And the next thing you've got todo is you've got to provide
some opportunities for growth.
This is where you get tostretch their abilities.
So you want to give them somechallenging projects, maybe some
things that require initiativeand a lot of problem solving,
but you want to assign that taskto them, that project to them.
You want to give them thoseleadership roles and teams or

(20:43):
projects that gain a lot ofhands-on experience.
That's important, you knowexpand their responsibility and
that helps them to reallybroaden their perspective.
And then you want to getfeedback from them and
evaluation, and so you want tohelp them.

(21:05):
You want to make sure you gotregular check-ins with them.
You want to talk about theirprogress, talk about things that
are challenging them, ask themwhat's the most challenging
thing you're dealing with.
So spend a lot of time askinggood questions and then make
sure that you have good formalperformance reviews, make sure
you help them set the goals andyou've got a way to measure

(21:28):
their growth and you just wantto, you know, be honest with
them and them be honest with youas you have this feedback.
And then, lastly, what you wantto do is you want to seek God's
guidance, according to Proverbs3, 5, and 6,.
I think it's important that youencourage that person that's

(21:50):
your number two to pray, toreflect throughout this growth
process and remind them thatleadership is a spiritual
journey as much as it is aprofessional one.
So that's really important.
And then the next thing that youneed to do is you need to
empower them.
I've seen that happen time andtime again the leader will do

(22:15):
everything, the owner will doeverything up to this point, but
then they won't empower them,they won't let them have that
responsibility.
So you want to empower them.
It means you've got to trustthem with a lot of
responsibility and you've got totrust them with decision-making
authority.
And I worked for a person veryshortly.

(22:36):
It was a very short period oftime and before I understood he
hired me as a number two person.
But he never would let me havethe opportunity to make
decisions, and even when theywere simple decisions and I
would make those decisions, Ialways got called into his
office and he was somewhat upsetthat I made these decisions

(22:57):
without him.
Some of these decisions weremade even when he was out of the
country and he was upset aboutit.
And these were decisions thatwe had already talked about and
we knew that if ABC happened,then we made the decision and
those things happened and I madethe decision.
But some people just don't wantto empower the people that they

(23:17):
have or that number two person,and so they've got to be able to
lead independently.
That's the only way they'regoing to strengthen themselves
with the confidence and thecompetence that they really need
.
You've got to empower them.
So you do that by delegating.
You delegate by clearlyassigning those tasks to them

(23:41):
and outlining very specificallywhat your expectations are.
That's important.
And then you've got to buildtrust.
You've got to do that throughhaving these good, honest, open
communications with them and itreally creates this
collaborative you know I'mtalking about collaborative
environment all the time,because this important is

(24:04):
powerful within an organizationand then you want to get regular
feedback from them and you wantto make sure you encourage
their efforts.
And then you want to set clearexpectations.
That's the next thing, clearexpectations.
You want to have themunderstand what's expected of

(24:24):
them.
And then you want to make sureyou have accountability.
You've got to review theirprogress on a regular basis and
you've got to address any kindof problems right away and
you've got to offer constructivethings that you can help them
with when those expectationsaren't met.
And so you've got to do thatand you've got to recognize and

(24:48):
celebrate what theircontributions are.
That's so important, even inthe accountability process.
And then again you seek God'sguidance.
Encourage that person that'syour number two to seek his
wisdom.
Remind them to lead, but leadas a servant and be like Christ.
In Mark 10, verse 42 through 45, he talks about this.

(25:12):
So some of the best practices, Ithink, for practicing
empowerment is.
You know, you kind of startsmall.
You know, delegate some smallertasks first before you increase
their responsibility.
Don't go from zero to 100 milesan hour right off the bat.
The next thing you want to makesure you're transparent.

(25:34):
You know, share your thoughtprocess, make sure they
understand why you're askingthem to do what they're doing.
That's important.
That helps them to learn and togrow and then again celebrate
their successes and then, whenyou do have to correct them, be
gracious about it.
You know, deal with themistakes, but do it with

(25:57):
kindness, do it with clarity,don't just come down on somebody
like a hammer, but do itgraciously.
You know, I've seen number twosget berated in front of
employees and in front of thosethat they're in charge of or
those that they're supervisorfor their supervisor, and that's

(26:19):
really something that youshould never, never do, unless
you just want to have a yesperson, unless you just want to
have somebody that is not goingto be that person that leans in
because they'll be afraid to.
So those are some of the bestpractices.
And then, you know, make surethat you document things,
document that process.
Maybe you need to have somebodyhelp you write a process for,

(26:45):
you know for developing a numbertwo, but have it written down
and then, maybe just for a while, maybe for a period of time,
just let them shadow you, justlet them learn, let them watch,
and so you can do that.
But you've got to communicatethis plan.
You've got to have a plan, awritten plan, show it to them,
tell them why this is what we'redoing, here's how we're going

(27:07):
to go about it.
And then you've got to begin tohave that timing, because it
might be 12 to 18 months beforethey're ready to transition into
that number two spot.
So that's important.
So you've got to set that andcommunicate that timeline to
them so that they understandwhat's going on and don't tell

(27:30):
them oh, it's going to be 18months and it's been 18 years
and you still haven't put themin that spot.
So that's important.
So you develop that action plan,have you a good action plan,
you know what your needs are,and then set up an action plan
of what you're going to do andhow you're going to do it.
And you're going to have somechallenges.

(27:51):
You're going to have somechallenges.
You're going to have resistancefrom other people.
Maybe they think they shouldhave been chosen.
I went through that and you'regoing to have some resistance
and you've also got to keepmotivating the number two person
because they'll wane in theirsome resistance and you've also
got to keep motivating thenumber two person because
they'll wane in their motivationsometimes and you got to help

(28:12):
do that, help continue to keepthem motivated.
And then you've got toencourage them to be independent
in their thinking and that'simportant.
So make sure that you do thatand help them to handle mistakes
.
You know, a great example is thestory of Moses and Joshua.
You know they give a greatexample of raising up a number

(28:36):
two and Moses identified Joshuaas a very faithful, as a very
courageous person and you canread about that in Numbers,
chapter 27.
And he mentored him, he gavehim opportunities to lead, you
know, according to Exodus,chapter 17.
And he empowered him, he gavehim responsibility and what

(29:00):
Moses was doing is he wasplanning for his succession and,
you know, and he talkedpublicly to the congregation, to
the people of Israel, aboutJoshua.
He did that publicly andprepared him publicly.
You can read about that inDeuteronomy, chapter 31.
But they had a great relianceon God throughout that whole

(29:22):
process and that is kind of ahighlight for the importance of
faith in all leadershipdevelopment.
So, raising up a number two,it's really an act of faith.
It's an act of stewardship,because that's our
responsibility as leaders.
And when you identify thatright person, you develop their
skills and their character andyou empower them to lead.

(29:45):
You're planning for yoursuccession, or maybe the
succession of anotherhigh-ranking position within the
organization.
So you honor God when you dothis.
You honor God when you'repreparing that person.
So seek his guidance in everystep that you take when you're

(30:05):
talking about doing this, andyou trust, trust God, trust him
that he will equip both of you,you and that number two person
to fulfill his purpose.
Well, lord, we come before youright now, lord, and we ask you
to grant us wisdom to raise upleaders who reflect your heart.
Lord, guide us with your spiritand may our efforts glorify you

(30:28):
as we build these organizations.
Lord, rooted in faith, rootedin service.
Lord, help us to apply theseprinciples to do more than just
raising up leaders for ourbusiness, but we're raising up
people that are godly, powerfulmen and women in their personal
lives as well as their careers.
And, lord, we thank you forhelping us to do that.

(30:49):
In Jesus' name, amen and amen.
Well, thanks again fordownloading this week's podcast
and I hope you'll help us growthe CBC family and community by
sharing this podcast with atleast four or five other people
you know.
Put a link to this podcast onyour Facebook, four or five
other people, put a link to thispodcast on your Facebook page

(31:09):
or your LinkedIn page andthat'll really help us to grow
the Christian Business Podcastcommunity and family.
Well, that's all the time wehave for today, so until next
time, remember that Jesus isLord and he wants you blessed.

Speaker 1 (31:29):
Thank you for tuning into this week's Christian
Business Concepts podcast.
Go toChristianBusinessConceptscom for
more information and resources.
Be sure to check out otherpodcasts that will help you take
your business and your personallife to a whole new level of
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Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

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