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July 28, 2025 30 mins

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What does it really mean to win?
Lately, I’ve been sitting with this question—and the more I observe high performers, the more I notice a common thread: the most successful people aren’t doing everything. They’re obsessed with one thing.

This episode was inspired by my time at the Aspire Tour, where leaders like Ed Mylett, David Goggins, and Jesse Itzler laid out their blueprints for success. What stood out? Simplicity. Focus. Depth. Whether it’s Bezos building everything around the customer, Rolex sticking to watches, or Jiro dedicating 75+ years to perfecting sushi—true winning comes from going all in on what aligns most.

Here’s what you’ll take away:

  • Why obsession with one thing beats juggling many
  • How the world’s best build momentum through narrow, deep focus
  • A new lens on “winning” that goes beyond titles or income
  • How to find your personal definition of winning—one that aligns with your values and fuels consistent growth

Let’s redefine winning together. Subscribe to the Winning Is... newsletter and tune into the show to explore powerful stories and timeless truths that help you stay aligned, focused, and fulfilled.

Thank you for tuning in! If you feel led, please subscribe & share the show to others who you believe would benefit from it.
Keep in touch below!

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Do hard things.
Help one person, be good and dogood, live a life of discipline
, and you will always win.
You have all the tools that youneed to succeed.
Welcome to win today.
Thank you so much for tuning in.
My name is Ryan Cass and I amyour host.
My purpose in this world is tohelp push people further and

(00:22):
harder than they believepossible and become unshakable
in what matters most to them intheir lives.
Every week, you're going tolearn from either myself or a
renowned expert in their field,and we're going to unveil pieces
of our playbook to help you wintoday.
Please, if you love this show,subscribe and share it with
somebody that will benefit fromit.

(00:43):
Let's dig in what is winning?
How do you define that?
It's a question that I'm goingto be exploring more frequently,
as the business is evolving andas I've noted two things in

(01:05):
particular from notablecompanies and founders, ceos and
creators, and that's curiosityand obsession.
Over one thing the more that Idive deeper into people that I
admire want to learn more about,and same thing with businesses.

(01:27):
Is that what has made so manypeople that we love to talk
about on the show or in circles?
We often bring these people upand when we deep dive them,
bring these people up.

(01:48):
And when we deep dive them, itwasn't that they've done a
million things, it's thatthey've done one to two things,
maybe three, extremely well, andthey've remained curious and
obsessive over that thing.
I believe we live in a worldnow where it can appear that the

(02:12):
key to success is doing athousand different things very
well and that's exaggerated,obviously, but doing many things
very well, and if we don't haveour hands in enough different
pots, then we're not doingenough.
Yet when we go and dive deeperinto businesses and stories and

(02:36):
the reason why many of thesefolks that we admire are the way
they are and why they've madeit the way they have, a million
things don't come out.
So why is it that we at timescreate these definitions or

(02:58):
these long laundry lists ofhere's the key to success,
here's how you get rich quick,here's how you create the life
you want.
Just follow my 27-step guide.
I'm committed to exploring whatwinning is.

(03:21):
Even this podcast Win Today.
I've had this thought in mymind for a while now as I've
been running, and that's where Ido a lot of my thinking on life
and where things I believe aremost clear to me, either running
or sitting down with a journal,but usually running first.

(03:41):
I've been pondering what evenis winning?
What does win today mean tosomebody else that's listening?
Because my version of whatwinning a day looks like can be
completely different than whatyour version is.

(04:02):
As an easy example, my life maylook completely different than
yours.
I don't have a family at home,meaning kids or a spouse that
I'm tending to daily.
Therefore, my definition ofwinning may look completely

(04:24):
different in that, I wouldimagine for those that are in
that category, winning is thatthey've taken care of their
family that day and been thebest father, husband, spouse,
leader, wife that they can be.
What I'm getting at here is thatthere's no singular definition

(04:45):
to what winning is, and that'swhy I'm on this quest to explore
what that is, be highly curiousand obsessive over that, so
that we can unlock uniqueinsights for people and help you

(05:06):
and help us craft a perhaps adifferent definition for success
, for winning, other than adollar figure in your bank
account, a scoreboard.
What's on a scoreboard?
What a particular outcome is?
What if winning was somethingvery deeply connected to your

(05:33):
heart?
What if, by creatingconversations with notable
founders, ceos and creators,just like we have been for the
last several years, and focus onwhat winning means to them,
then that can help you andothers craft a meaningful
definition as to what winning isto you, and I don't believe

(05:55):
that it's something that, oncewe define, it remains fixed
forever.
Perhaps it does, but perhaps itevolves.
But perhaps it evolves.
Part of what drives this we'llcall it evolution of the podcast
now the newsletter Winning Is,which came out today.

(06:19):
Part of what's driving that isI'm seeing a trend in where

(06:45):
businesses and people that arereally, really crushing it in my
eyes and that I admire the mostare doubling and tripling down
on less equals more and focusingon that, or rather remaining
open to that thing, or very fewthings that they're really
focused on, meaning that, oncewe're fixated on this one thing,
that we still remain open tothe possibilities, the ideas,

(07:07):
the thoughts, the perspectives,so that we can then take the
best of those insights andinfuse them into this one thing
that we're really diving deep on.
I went to the Aspire TourConference last year in
Charlotte the Aspire Tourconference last year in
Charlotte, north Carolina and Iremember walking away feeling

(07:29):
extremely inspired.
So how cool is that Aspire,inspire.
The founders, andrew Cordelland Eddie Wilson, are amazing in
that they've built a businesstour that has generated over
$100 million in revenue, hasspeakers like Jesse Itzler,

(07:50):
david Goggins, ed Milet, codySanchez some of the biggest
names across sports, acrossbusiness, across every major
industry, and they get thesepeople to come to various cities
all over the globe and sharetheir stories.

(08:12):
You get to hear keynotespeeches and I remember getting
to hear from Ed Milet, who's oneof my favorite of all time.
Hearing him live talking aboutthe power of one more.
Hearing him live talking aboutthe power of one more was by far
one of the most uniqueexperiences that I've had.
As it relates to conferences andbusiness events.

(08:35):
There's a different type ofenergy.
When you enter these rooms andwhen you come in there with an
open mind, you leave with somuch, so many nuggets that you
can go act upon, and thesepeople are giving you their
playbooks.
One thing I've another thingI've come to learn is that
there's no real deep secrets.

(08:56):
A lot of these people whetherit's Ed Milet, david Goggins,
jesse Itzler, everybody I justnamed they're giving you the
game right there, but you haveto be open and curious to being
able to actually hear it and seeit right in front of you.

(09:17):
A lot of us are rather manypeople can be closed off to the
game being given to you becausewe make up this story in our
minds, that it's supposed to besomething really complex, and we
are completely closed off towe're being handed the keys

(09:38):
right there.
So, at this Aspire Tourconference, andrew and Eddie and
Eddie, who sold 76 companies ina year worth $1.2 billion are
just giving nothing but freegame.
Andrew gave about a two-hourkeynote about money and he

(09:59):
titled it Money Is, Now money is.
Think about that.
Money is, money is, money iswhat.
Here's some of the things thatcome out and this is from the
stage, but then also probablythe same things that we say in
our own minds Money is freedom,money is power, money is

(10:23):
stress-free, Money is stressful,money is abundant.
There's no singular definition,but it's something that we talk
about a lot.
Andrew had a video series andpodcast for a while called Money
Is, and he would uncover theinsights from these people that

(10:43):
I've mentioned Alex Rodriguez,the biggest names To show that
money is a game Andrew's wordsbut that it's not something that
can be universally defined,however, or, in addition, by

(11:27):
hearing what it is to peoplethat we look up to.
That can then give us a tool tocraft what it means to us and
become more clear on what wereally want, or to build a
better relationship with thething.
So I've been thinking for quitesome time on when today, and
where I see this business goingand where I see the Unshakable
Discipline community going.
I recognize that I talk aboutwinning a lot, and winning can
mean a lot of different things.
Therefore, I'm choosing to goon a quest to understand what

(11:49):
winning means to notable peoplearound the world, and by doing
so, that is going to help youcraft your own meaningful and
unique definition of whatwinning is and perhaps help you
in your future conquest, becausenow you know what winning is

(12:12):
and you can apply thatdefinition across the things
that are most important to youin life, whether it's your
family, your business, yourrelationships, your fitness.
You have a more clear or you'reopen to exploring that perhaps
winning is more than a dollarfigure.

(12:34):
Winning is more than what thescoreboard says.
Winning is more than one thing.
So we're going to do that.
That's what we're going tostart pivoting towards, and I'm
going to be more intentionalabout asking people and creating

(12:54):
conversations about whatwinning is to them, and I'm
curious as to what we'll find.
I believe that we will uncoverdefinitions that we could have
never possibly dreamt of andperhaps by doing so, one thing

(13:20):
that we learned from somebodyelse is the one thing that you
were looking for that reallyresonates with you, that you can
now use as your guidepost.
So we're not going to focus ona thousand different things.
We're going to go and focus onwhat is winning and be highly

(13:41):
curious and obsessive and sharewhat we learn along the way, and
I'm taking a piece of theplaybook from the best and
brightest that I've seen so far.
We're going to dive deep on onething that's going to come out
in the weekly newsletter, that'sgoing to become more apparent

(14:01):
in the podcast interviews andthat's going to become more
apparent in the content that I'mputting out on a weekly basis.
So we have definitions, orrather we've got existing
platforms, as to what is money,what is wealth, but what is
winning and maybe even thispodcast changes to winning is

(14:26):
I'm not sure.
Let me know what your feedbackis on that.
I think about when I thinkabout one thing and then I'm not
sure.
Let me know what your feedbackis on that.
I think about when I thinkabout one thing, and then I'm
going to get into my definitionof what winning is, both in long
form and in short form.
I mentioned that I've noticedtwo things that stand out with
notable brands and peoplecuriosity and obsession.

(14:48):
Think about Amazon and what hasmade Amazon what it is today.
Yes, now Amazon sells millionsof products and across a wide
range of domains, meaning thatyou can buy clothes from Amazon.

(15:10):
You can also host your websiteon Amazon.
Now you can buy your shoes fromAmazon.
You can also have a packageshipped to you via drone.
Jeff Bezos, when he was startingAmazon, had a focus on one

(15:31):
thing.
It wasn't for Amazon to be thebest at selling a million
products.
It was for Amazon to beobsessed on one thing the
customer, customer obsession.
I've been following Nick Baer'slead on listening to Founders

(15:52):
podcast by David Senra and thispodcast is.
I'm loving it because everyweek it's diving into the story
of a successful founder andtheir biography and David goes
into shareholder letters thathave been written, previous
books that have been writtenprevious books that have been
written, existing books that areon these people, interviews,

(16:15):
one-on-one discussions with themreally unpackaging.
What is it that makes peoplelike Jeff Bezos and Steve Jobs
the founders of Nestle?
I most recently listened to thestory of Michael Ferrero.
If you've had the Ferrero andRocher chocolates with the gold

(16:36):
wrapping amazing story, I wouldhave never knew that that family
in Italy basically are thepioneers of the chocolate world
$40 billion empire.
Going back though, on JeffBezos, it uncovers that Amazon

(16:58):
became so successful because thecustomer was first and the
customer was the point ofobsession.
The customer wanted convenience, the customer wanted a wide
array of products and theywanted it to be able to come to

(17:19):
their door quickly withouthaving to go somewhere else.
Now, jeff didn't build Amazonto focus on what he thought was
the best thing to do.
He let the customer dictateeverything to what now Amazon is
today.
So Amazon expanded across allof these domains because of one

(17:43):
thing the customer See what I'msaying here.
One thing Listening more to theFounders podcast, I listened to
an episode about Rolex.
If you notice, what is one thingthat Rolex makes, what are they
known for?
Watches.
Have you ever thought about thefact that Rolex doesn't make

(18:07):
handbags or backpacks orclothing or anything else?
They're focused on making thebest watch in the world, and
that's what they're known for.
Sure, if they made a clothingline, would it do well,
absolutely Anything that's gotthat Rolex crown on it.

(18:27):
People want to buy it becausethey've built a brand that
people recognize for extremelyhigh quality and craftsmanship.
But Rolex is focused on onething an amazing watch.
Private investors or if Rolexwas public would likely attempt

(18:53):
to lead the company intoproducing all of these different
products, but they got reallygood at one thing.
Many of you may love sushi, as Ido, and one of my favorite
documentaries that I've everwatched is Hero Dreams of Sushi.
Hero J-I-R-O.
I may be pronouncing itslightly off.
I believe it's Hiro.
Hiro Dreams of Sushi, hiro Ono.

(19:17):
For 75 years plus and counting,hiro has focused on making the
best sushi in the world.
He has, if I'm not mistaken,either a two or a three Michelin
star restaurant in Tokyo.
There are, I believe, no morethan 20 seats in the entire

(19:41):
restaurant.
World ranking officials,presidents, ceos, celebrities
they all go to Hiro's sushirestaurant, which is in the
middle of a strip mall in Tokyo.
You would walk right past itand not know that it's there,

(20:02):
yet these are where the mostfamous people in the world go to
have sushi when they're inTokyo.
The most famous people in theworld go to have sushi when
they're in Tokyo.
He only makes a select number ofitems.
He gets his rice from the sameexact place.
He only buys tuna from oneperson.

(20:26):
Any of his apprentices have tolearn even how to perfect rice
for three to five years beforethey're even allowed to touch
fish.
If the sushi isn't up to Hiro'sstandards that day, it doesn't
get put on the menu, and thiswould be something that you and
I, I'm sure.
The things that get rejectedoff the menu that day are things

(20:47):
that you and I would absolutelylove and wouldn't be able to
taste the difference, but that'sthe level that he has.
If he decided to open up aburger joint, would it do well,
of course, but it gets away fromhis one thing sushi.

(21:10):
So I'm going down the curiosityjourney myself and that what
happens if we become highlycurious and obsessive of one
thing?
So what is winning?
I've been journaling on thisand I'm going to read to you my

(21:30):
journal entry and all the thingsthat come to mind with what
winning is, and then I'm goingto define it very short and
sweet and the reason why I'mgoing to read out the entry is
because it's my intention thatby doing so, it may help create

(21:52):
new perspective for you.
Create new perspective for you.
It may help you with yourdefinition.
It may help you in thinking ofsomething that you wouldn't have
associated winning with before.
Much of what's on here isn'ttied to particular objectives.
It's more tied to states ofbeing, which I've come to

(22:17):
appreciate much more, in thatI'll share more insights on that
.
How about that?
So here's the entry and here isthe, and at the end we'll have
the singular.
Here's my one sentence.
Definition of winning is Winningis more than a score.

(22:38):
Winning is closeness and richconnections with special people.
Winning is freely exploring theworld and local community.
Winning is injecting somethinggood in the life of one person.
Winning is injecting somethinggood in the life of one person.

(23:01):
Winning is recognizing theabundance of good in this world
and always seeing the light.
Winning is smiling when someoneisn't kind or a situation
that's not favorable unfolds.
Winning is catching sunrisesand sunsets.
Winning is expanding your body,mind and soul to new heights

(23:22):
that your former self wouldn'thave deemed possible.
Winning is seeking knowledge andperspectives.
Winning is going after yourgoals with all of your might.
Winning is creating your dreams.
Winning is recognizing thesound of nature.

(23:45):
Winning is stopping toappreciate the birds chirping,
squirrels running and treebranches swaying.
Winning is being grateful foreverything in life.
Winning is doing your best toembrace and exemplify the word
of the big man upstairs.
Winning is paving a path forothers to follow, guiding those

(24:07):
who look up to you and sheddinglight for those who you don't
even know look up to you.
Winning is being clear on whatyou want in this life and
creating the time necessary tobe clear.
Winning is being the rock foryour family, regardless of what

(24:27):
trials and tribulations haveoccurred.
You are the one who stands talland makes the choice to be
better.
Tall and makes the choice to bebetter.
Winning is always staying youngat heart, smelling the roses

(24:49):
and remembering to make the mostof this life, because it's not
infinite.
Winning is being in constantcreation and alignment.
That's my short form definition.
Winning is being in constantcreation and alignment.
Constant creation of the thingsthat I mentioned there.

(25:10):
Constantly creating deepconnection, constantly creating
the opportunity to appreciateeverything around you,
constantly creating a goodexample for others to follow.
Being in alignment is being inalignment with your goals, the

(25:36):
things that matter most to you.
Winning is being in constantcreation and alignment.
That's my definition right atthis moment and I feel firmly
rooted in that.
But with curiosity andobsession it could be refined,

(26:08):
it could be tweaked, and that'sokay.
But with that, as I sat andstared at those words on the
paper for a long time that I'vebeen journaling about, I feel
clear in that those are thethings that really matter most
in life and when I'm inalignment with that, that's what

(26:28):
winning is to me.
Not all 27 of those things atone single time time, or however
many I just mentioned, but alot of those things are what I
work to inscribe into my DNA,into my way of being, meaning.

(26:50):
It's just a part of who I am,it's just what I do and it's not
something that I have to writedown every day.
It's like putting on a shower.
It's like putting on a towelafter you get out of the shower.
Setting a good example forsomeone isn't, in my view,
something that needs to bewritten down.
It's just something you do.
Prioritizing connection withpeople that mean most to you is

(27:18):
a part of who I am and it's whatI do.
There was a point in time wheremany of those items mentioned
were things that need to bewritten down, because they were
things that I want habits andtraits that I wanted to build to

(27:39):
ultimately be inscribed into myDNA.
But that's really now how Idefine myself and it's my wish
that, by sharing that, it getsyou thinking about what is
winning to you and there's noright and wrong answer here and

(28:03):
we're going to keep providinginsights on what that really
means and how you can shape whatthat means to you.
But I'm truly excited aboutexploring this further and
helping people craft thatdefinition, because when you can

(28:23):
look back and it's easy attimes to not believe that we're
making progress or doing enoughbut when we have something
clearly defined, then we caneasily look at that definition
and it's almost a binaryresponse Am I in alignment with

(28:45):
that or am I not?
Or am I working to fulfill thatdefinition?
Is what I'm doing today, iswhat I'm doing this week, in
alignment with that or not, withthat or not?
It almost serves as thisinstant reminder or incentive
like, hey, actually, no, you are, you are winning, you are

(29:05):
winning.
And then that's going to giveyou the momentum, energy,
excitement to keep showing up togo after the big things, to

(29:26):
chase your dreams, to touch yourdreams, and perhaps I don't
want to get ahead of myself.
I'm going to hold my thought.
Winning is being in constantcreation and alignment.
I want to know what winning isto you and we're going to keep
going down this path.
Be sure to subscribe to thewinning is newsletter which is

(29:51):
down in the bio or the link shownotes, and we're going to win
today, but be more clear on whatwinning is.
I really appreciate you guys.
Let's go win.
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