August 5, 2025 • 10 mins
If you want to connect with us -> https://defeat90.com/connect
In this raw, unscripted episode, Jeremy ditches the notes and speaks straight from the heart about one of the toughest parts of entrepreneurship—navigating honesty, bluntness, and conflict in business relationships. Triggered by a recent real-life situation, Jeremy explores the delicate balance between speaking truth and showing grace, and why being vulnerable and authentic is so important for personal and professional growth.
He dives into the challenges of knowing when to confront someone and when to let things go, sharing insights from his own journey with personality types, expectations, and the desire to build healthy, impactful connections. Jeremy invites listeners to reflect on their own approach to conflict, communication, and the importance of understanding where misaligned expectations can lead to broken relationships.
Whether you struggle with confrontation or just want to build stronger, healthier business relationships, this episode is packed with relatable stories and practical wisdom. Join the conversation and learn why real change—and real business success—starts with honest, courageous communication. https://defeat90.com/connect
Show Note Chapter Markers 00:00:00 – Intro: Going Off Script Jeremy shares why this episode is unscripted and sets the stage for a vulnerable conversation. 00:00:22 – Raw Honesty & Vulnerability Why Jeremy believes in being real, sharing weaknesses, and processing tough moments out loud. 00:01:23 – The Honesty Dilemma A real-life situation sparks the question: When is honesty worth the risk of conflict in business? 00:02:32 – Confrontation or Letting Go? Jeremy grapples with whether to address a business issue head-on or let it slide. 00:03:40 – Personality, Bluntness, and Growth How personality types (like Enneagram 8) influence our approach to honesty and conflict. 00:05:00 – Speaking Truth with Grace The challenge of balancing honesty, bluntness, and kindness in business relationships. 00:06:02 – Navigating Tough Conversations When to confront, when to hold back, and what’s really at stake in business interactions. 00:07:08 – Values, Integrity & Accountability What happens when someone’s actions don’t match their stated values? Jeremy reflects on responsibility and calling others in. 00:08:14 – The Heart Behind Conflict Digging into why we do what we do, and how expectations shape relationships and disagreements. 00:09:13 – Healthy Conflict vs. Broken Relationships How to move from miscommunication and assumption to understanding and resolution. 00:10:22 – Building Better Business Relationships Jeremy’s hope for the Defeat 90 community: more honesty, healthier conversations, and stronger connections.Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
I'm going to get myself in trouble,for this episode of this podcast,
because I don't have my iPadthat normally keeps me on track of
what I'm talking about and or points.
I have no points, actually,with this, this podcast,
there's some things that happenedthis week, and I just feel like
it's gonna be better coming from my heartand thinking through this versus just
(00:20):
this scripted thing.
I think this is a place for meto be vulnerable with you guys.
There's some thingsI've been thinking about.
I just kind of want to process.
And that soundsnot even remotely intriguing to you.
Then just, hey,catch the next episode next week.
No worries.
If you'd like to see me crash and burn,stay tuned.
Your stories,your experiences can change it all.
(00:41):
Let's fight until you're together.
We can defeat 90.
Okay, so
in fairness to myself,
I shouldn't say
I should havea little more faith in myself
to be able to just to talk from my heart.
But, you know, part of this defeat
is being vulnerable is being honestabout where we're at in life.
for me, I always want to use the thingsthat I'm going through or learning to help
(01:05):
because I want to share my weaknesses.
are some things that happen this week.
I'm not to get into that,because I think it's
for the sake of the person and people.
And, but it's led me to this,
this place of this question,where does honesty
and bluntnessHow does that fit in in business?
Now, you might say, hey, being whatwe should always be honest, we shouldn't.
(01:29):
Some people mean like,maybe we shouldn't be blunt.
We should communicate
with grace and say things in a kind,loving way in which I 100% agree with.
But even then,
even when you speak things, there's thingsright now you probably have.
You want to say to someone
in a relationshipin or a business relationship or whatever,
but you know, you can't say itbecause they won't receive it.
So how do you know when to behonest or not?
(01:51):
To be honest, I think we should always behonest, don't get me wrong.
But I think there's this, this, this, thismisnomer of
how we go through
and interact in relationships
with how we feel about situations when,
especially when people do thingsthat we're not so happy with.
That's kind of what happens.
There's there's a situationthat I'm very frustrated about, happens
(02:15):
that I don't have the relationshipwith this person to be able
to talk through with them, to say, hey,
this, this and this, we're not okay.
Now. I'm I'm literallywaiting that out of going, like
for the health of that personand how the situation happened.
Should I have that conversation?
But it brings me to this biggernarrative of like,
(02:36):
I thought, hey,this could be a great opportunity
for you guys to understand who I amnow, I've talked to you guys before that
I think I've said this in many episodes,that I am not on the grand scale now.
Grand.
And I want to clarify somethingreally, really important right now.
I do not think that
our number should be used as crutchesbecause I've met those people.
Like what?
I'm just an eight and I'm eightand I can just be rude
(02:59):
and and but this is who I am, like,you know, like.
Or it could be Myers-Briggs, right?
Look, this is just who I am. I hate that
I believe these are tools that help us.
I think, you know,
healthy person should have all attributesof all the different numbers
and be striving towards thatbecause that makes way more sense.
So the eight, yes, I stand up for,you know, speak truth to power
(03:19):
for nine is a peacemaker.
It makes things better.
Like you care for people you knowyou can start pulling these things in.
Sevens are a blast. Thank you.
Except I'm like eight seven.
Which I can be fun.
I mean, sometimes,
probably more goofy than funif we're just being like,
I guess I'm being vulnerable.
More goofy than fine.
Maybe I'm fun.
Anyways, getting back to the point.
(03:40):
So there's this.
This part of methat I'm an eight and eight have.
Let's put it this way.
When I finally figured out.
So I took the test of figuring outwhat I was as an Enneagram,
it was like itsaid, that was A27 exactly in the numbers.
And then, a wing eight or whatever it was.
And then I had no other numbers, like
(04:00):
they were basically almost zerofor the rest of them.
And so I thought I was a twofor the longest time.
I'm not a two.
That's
I remember when I read this book,wrote back to you about figuring this out,
and when I found out that I was an eight,I was legitimately pissed
because every eightI had ever met in my life,
and this is leading upto a story of different things, is that
(04:23):
they're not nice people,they're very blunt and they're rude,
and it has to be their wayand they can come across controlling.
When I realize now as I've studiedthis more, those are very unhealthy.
Eight there's been times in my lifewhere I have definitely been unhealthy.
Eight and acted that way,but when eight are healthy,
they gravitate to acting like ato and taking care of people, which is
(04:44):
something that I love doing.
And also two eightat the healthiest version of who they are.
They're very philanthropic,and they are about helping
change the world and make a difference,which I, I want to do with my life right.
Getting back to this whole thingabout speaking truth in relationships
really powerful about speaking truthand love and doing that.
(05:04):
But most people don't want that.
And I've I've experienced more in my life,
especially even when I'm thoughtfulof the things of how I've hurt people.
And that and I really hate thatbecause I, I don't want to ever be blunt
for being blunt.
Like, I don't want to ever just scold youfor being like, oh, you suck.
Like, like, especially if I've been hurtor something like that.
(05:26):
I it's not worth it to mebecause in the end, like, I genuinely care
about the entire picture of things.
And that's a big thing at our agency.
It it's not worth it.
Or at least for the healthy eight.
I guess my question,my thought through all this is
how do we in business?
Have the tough conversations?
(05:48):
How do we talk about the thingsthat people don't want to talk about?
How do we do conflict?
I know how I
so there's a situation, for this personreally let me down in business.
And there's some thingsthat I was really not happy with and that
I'm again, been debating whether I'mgoing to confront or not confront.
there's a ramification to that, right?Because I don't know this person.
(06:10):
Well, if I knew them, I'd beI'd be very much like, hey, let's.
So is there a time
when things just need to let let be,
and when is a time that when you actuallyneed, need to confront things?
This is when I'm wrestling.So this is the topic I'm bringing.
So if you don't want to commentin this section about this, about,
hey, when when is the time to confrontand when is the time not now.
(06:32):
Granted, the degree of severity.
What happened wasn't it wasn't
super, super severe,but definitely based on what this person
does for a living contradicts their valuesand what they stand for.
And that to me is that to meis the scarier part about it
is this this person's businessrelies on these value sets,
(06:54):
and then they justdid something against that.
Then am
I doing them a disservice by not actuallyconfronting and saying, hey,
these actions don't line up
with who you say and who you want to beand what you do.
thinkthe bigger part of this whole thing is.
Understanding my heartand why I do what I do
we all have expectationsof what we want in relationships.
(07:17):
I've had some really tough and hardrelationships that have ended and things
and conflict in and of itself can be greatif it's done in a healthy way.
I'm not talking about fighting or arguing.
I'm talking about actual legitimatelike questions, conflict, where they do
really well is when it's based health,where we can have those conversations.
more times than not,the reason why conflict happens
(07:39):
is because I have expectation of whatsomething should look like.
And you have expectationsand they don't match up.
we assume the other person shouldjust know that and should just get it.
And so we go, why don't you do this?
And they're going, why don't you do this?
And before you know it, instead of itbeing a hey, let's get to know each other,
let's understandhow we should approach this.
It becomes this epic warthat turns into huge, that lasts
(08:03):
sometimes for decades, and thingswhere people stop talking to each other.
And or broken relationshipsor things that are ended.
And I hate that coming from a personthat's perfectly capable of confronting
and coming from a personthat always wants to work through things
and figure it out and fix the problem.
Because I'm a problem solver,that's part of how I'm wired.
I hate when it can't be,and I wrestle with I hate the situations
(08:25):
whereI don't know how to solve the problem.
I don't know how to confront itin the right way
because it may not be received or,you know, maybe it's not worth it
or whatever, I guess it comes down to whyyou're doing what you're doing.
And so I challenge you as you startlooking at one, when you have a conflict
with someone in businessor employee or customer,
Try to figure outwhere the miscommunication is.
(08:47):
Try to understand the problem.
Ask questions Start
trying to get things to a placewhere you can start figuring out
where the misaligned expectations are Canwe come to a resolve?
Can we come to a place wherewe're on the same page?
Because the alternative working throughthings, we all have those relationships.
We all have those things in lifethat are forever broken.
my hope through talking about this, comingfrom a person's able to confront
(09:10):
is sometimes the healthiest thing you is.
Just listen And sometimesthe healthiest thing I can do
is say, hey, how you're acting.
Okay, this this is not okay.
And it's here'swhy and here's where my expectations are.
Help me understand.
That's I think one of the biggest things,if I do contact this person, I'm going
to start from a perspective of going,help me understand what's going on.
(09:32):
before I make any accusationor say to things, help me understand.
what you need, what you're wanting,where we got off track.
think it's a healthier place.
But anyways, your thoughts.
So hey, that's really randomand I probably got myself in trouble.
Price of something.
And probably maybe it's not even cohesive,but I just wanted to just
(09:53):
talk and be realabout to get to know more about who I am
and understand
that I care about relationships.
And this 90 and building relationshipwith you is super, super important to me
because I know that the only waywe're going to defeat the 90%
failure rate, the only way that our livescollectively will be changed
(10:14):
and we will be better at what we dois by having solid relationships,
good conflict, healthy,no conflict, good conversations.
So if you like this, hey, pleasesubscribe, comment.
Like all those things, wherever itwhatever platform you're on.
But know this I'm rooting for youand I look forward to getting to know you.
I'm going to get myself in trouble,for this episode of this podcast,
because I don't have my iPadthat normally keeps me on track of
what I'm talking about and or points.
I have no points, actually,with this, this podcast,
there's some things that happenedthis week, and I just feel like
it's gonna be better coming from my heartand thinking through this versus just
(00:20):
this scripted thing.
I think this is a place for meto be vulnerable with you guys.
There's some thingsI've been thinking about.
I just kind of want to process.
And that soundsnot even remotely intriguing to you.
Then just, hey,catch the next episode next week.
No worries.
If you'd like to see me crash and burn,stay tuned.
Your stories,your experiences can change it all.
(00:41):
Let's fight until you're together.
We can defeat 90.
Okay, so
in fairness to myself,
I shouldn't say
I should havea little more faith in myself
to be able to just to talk from my heart.
But, you know, part of this defeat
is being vulnerable is being honestabout where we're at in life.
for me, I always want to use the thingsthat I'm going through or learning to help
(01:05):
because I want to share my weaknesses.
are some things that happen this week.
I'm not to get into that,because I think it's
for the sake of the person and people.
And, but it's led me to this,
this place of this question,where does honesty
and bluntnessHow does that fit in in business?
Now, you might say, hey, being whatwe should always be honest, we shouldn't.
(01:29):
Some people mean like,maybe we shouldn't be blunt.
We should communicate
with grace and say things in a kind,loving way in which I 100% agree with.
But even then,
even when you speak things, there's thingsright now you probably have.
You want to say to someone
in a relationshipin or a business relationship or whatever,
but you know, you can't say itbecause they won't receive it.
So how do you know when to behonest or not?
(01:51):
To be honest, I think we should always behonest, don't get me wrong.
But I think there's this, this, this, thismisnomer of
how we go through
and interact in relationships
with how we feel about situations when,
especially when people do thingsthat we're not so happy with.
That's kind of what happens.
There's there's a situationthat I'm very frustrated about, happens
(02:15):
that I don't have the relationshipwith this person to be able
to talk through with them, to say, hey,
this, this and this, we're not okay.
Now. I'm I'm literallywaiting that out of going, like
for the health of that personand how the situation happened.
Should I have that conversation?
But it brings me to this biggernarrative of like,
(02:36):
I thought, hey,this could be a great opportunity
for you guys to understand who I amnow, I've talked to you guys before that
I think I've said this in many episodes,that I am not on the grand scale now.
Grand.
And I want to clarify somethingreally, really important right now.
I do not think that
our number should be used as crutchesbecause I've met those people.
Like what?
I'm just an eight and I'm eightand I can just be rude
(02:59):
and and but this is who I am, like,you know, like.
Or it could be Myers-Briggs, right?
Look, this is just who I am. I hate that
I believe these are tools that help us.
I think, you know,
healthy person should have all attributesof all the different numbers
and be striving towards thatbecause that makes way more sense.
So the eight, yes, I stand up for,you know, speak truth to power
(03:19):
for nine is a peacemaker.
It makes things better.
Like you care for people you knowyou can start pulling these things in.
Sevens are a blast. Thank you.
Except I'm like eight seven.
Which I can be fun.
I mean, sometimes,
probably more goofy than funif we're just being like,
I guess I'm being vulnerable.
More goofy than fine.
Maybe I'm fun.
Anyways, getting back to the point.
(03:40):
So there's this.
This part of methat I'm an eight and eight have.
Let's put it this way.
When I finally figured out.
So I took the test of figuring outwhat I was as an Enneagram,
it was like itsaid, that was A27 exactly in the numbers.
And then, a wing eight or whatever it was.
And then I had no other numbers, like
(04:00):
they were basically almost zerofor the rest of them.
And so I thought I was a twofor the longest time.
I'm not a two.
That's
I remember when I read this book,wrote back to you about figuring this out,
and when I found out that I was an eight,I was legitimately pissed
because every eightI had ever met in my life,
and this is leading upto a story of different things, is that
(04:23):
they're not nice people,they're very blunt and they're rude,
and it has to be their wayand they can come across controlling.
When I realize now as I've studiedthis more, those are very unhealthy.
Eight there's been times in my lifewhere I have definitely been unhealthy.
Eight and acted that way,but when eight are healthy,
they gravitate to acting like ato and taking care of people, which is
(04:44):
something that I love doing.
And also two eightat the healthiest version of who they are.
They're very philanthropic,and they are about helping
change the world and make a difference,which I, I want to do with my life right.
Getting back to this whole thingabout speaking truth in relationships
really powerful about speaking truthand love and doing that.
(05:04):
But most people don't want that.
And I've I've experienced more in my life,
especially even when I'm thoughtfulof the things of how I've hurt people.
And that and I really hate thatbecause I, I don't want to ever be blunt
for being blunt.
Like, I don't want to ever just scold youfor being like, oh, you suck.
Like, like, especially if I've been hurtor something like that.
(05:26):
I it's not worth it to mebecause in the end, like, I genuinely care
about the entire picture of things.
And that's a big thing at our agency.
It it's not worth it.
Or at least for the healthy eight.
I guess my question,my thought through all this is
how do we in business?
Have the tough conversations?
(05:48):
How do we talk about the thingsthat people don't want to talk about?
How do we do conflict?
I know how I
so there's a situation, for this personreally let me down in business.
And there's some thingsthat I was really not happy with and that
I'm again, been debating whether I'mgoing to confront or not confront.
there's a ramification to that, right?Because I don't know this person.
(06:10):
Well, if I knew them, I'd beI'd be very much like, hey, let's.
So is there a time
when things just need to let let be,
and when is a time that when you actuallyneed, need to confront things?
This is when I'm wrestling.So this is the topic I'm bringing.
So if you don't want to commentin this section about this, about,
hey, when when is the time to confrontand when is the time not now.
(06:32):
Granted, the degree of severity.
What happened wasn't it wasn't
super, super severe,but definitely based on what this person
does for a living contradicts their valuesand what they stand for.
And that to me is that to meis the scarier part about it
is this this person's businessrelies on these value sets,
(06:54):
and then they justdid something against that.
Then am
I doing them a disservice by not actuallyconfronting and saying, hey,
these actions don't line up
with who you say and who you want to beand what you do.
thinkthe bigger part of this whole thing is.
Understanding my heartand why I do what I do
we all have expectationsof what we want in relationships.
(07:17):
I've had some really tough and hardrelationships that have ended and things
and conflict in and of itself can be greatif it's done in a healthy way.
I'm not talking about fighting or arguing.
I'm talking about actual legitimatelike questions, conflict, where they do
really well is when it's based health,where we can have those conversations.
more times than not,the reason why conflict happens
(07:39):
is because I have expectation of whatsomething should look like.
And you have expectationsand they don't match up.
we assume the other person shouldjust know that and should just get it.
And so we go, why don't you do this?
And they're going, why don't you do this?
And before you know it, instead of itbeing a hey, let's get to know each other,
let's understandhow we should approach this.
It becomes this epic warthat turns into huge, that lasts
(08:03):
sometimes for decades, and thingswhere people stop talking to each other.
And or broken relationshipsor things that are ended.
And I hate that coming from a personthat's perfectly capable of confronting
and coming from a personthat always wants to work through things
and figure it out and fix the problem.
Because I'm a problem solver,that's part of how I'm wired.
I hate when it can't be,and I wrestle with I hate the situations
(08:25):
whereI don't know how to solve the problem.
I don't know how to confront itin the right way
because it may not be received or,you know, maybe it's not worth it
or whatever, I guess it comes down to whyyou're doing what you're doing.
And so I challenge you as you startlooking at one, when you have a conflict
with someone in businessor employee or customer,
Try to figure outwhere the miscommunication is.
(08:47):
Try to understand the problem.
Ask questions Start
trying to get things to a placewhere you can start figuring out
where the misaligned expectations are Canwe come to a resolve?
Can we come to a place wherewe're on the same page?
Because the alternative working throughthings, we all have those relationships.
We all have those things in lifethat are forever broken.
my hope through talking about this, comingfrom a person's able to confront
(09:10):
is sometimes the healthiest thing you is.
Just listen And sometimesthe healthiest thing I can do
is say, hey, how you're acting.
Okay, this this is not okay.
And it's here'swhy and here's where my expectations are.
Help me understand.
That's I think one of the biggest things,if I do contact this person, I'm going
to start from a perspective of going,help me understand what's going on.
(09:32):
before I make any accusationor say to things, help me understand.
what you need, what you're wanting,where we got off track.
think it's a healthier place.
But anyways, your thoughts.
So hey, that's really randomand I probably got myself in trouble.
Price of something.
And probably maybe it's not even cohesive,but I just wanted to just
(09:53):
talk and be realabout to get to know more about who I am
and understand
that I care about relationships.
And this 90 and building relationshipwith you is super, super important to me
because I know that the only waywe're going to defeat the 90%
failure rate, the only way that our livescollectively will be changed
(10:14):
and we will be better at what we dois by having solid relationships,
good conflict, healthy,no conflict, good conversations.
So if you like this, hey, pleasesubscribe, comment.
Like all those things, wherever itwhatever platform you're on.
But know this I'm rooting for youand I look forward to getting to know you.
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