Name: Joe Rogan Experience #1955 - Cliff Gray
Uploaded: 2023-03-15T00:00:00.000Z
Description: Watch the stand-up comedy video 'Joe Rogan Experience #1955 - Cliff Gray' from PowerfulJRE on Comedy Buff. Published 2023-03-15. Transcript available.

Watch the stand-up comedy video 'Joe Rogan Experience #1955 - Cliff Gray' from PowerfulJRE on Comedy Buff. Published 2023-03-15. Transcript available.

Joe Rogan Experience #1955 - Cliff Gray

Joe Rogan Podcast, check it out.
The Joe Rogan Experience.
Train by day, Joe Rogan Podcast by night, all day.
Hello, Chris.
What's up?
What's up, man?
Nice to meet you in person.
You too.
We've been chatting back and forth online for quite a while now.
Yeah, man.
You know, it's funny, I was looking at it, I think it's been like five or six
years since
our first, like, interaction.
How did you get involved being a hunting guide?
What was your, what's your path to that?
Yeah, man.
So it's a, I guess it's a long story.
You know, I grew up in a rural area.
My dad, my dad was a cattle rancher, and then he did a little outfitting when I
was a kid.
And then it, well, it's kind of a long story, man, because I thought this was
normal when
I was a kid, but when I was, when my dad was an adult, he was a cattle rancher,
and then
he went back to vet school.
And so he actually left outfitting and cattle ranching and pursued that, and
that was when
he was, like, in his 40s, you know?
And so that was my first exposure to, you know, being an outfitter or guiding
was through
my father.
And then, honestly, man, like, growing up, I hunted all the time.
I've been, I've been obsessed with, you know, hunting since I was 10, 12 years
old.
And then I went and kind of did a more traditional, I guess, lifestyle.
I went to school, went to undergrad, went to business school, and then I worked
in finance
for a few years.
And I mean, we can get deep into, like, why that didn't last.
You know, I got...
Maybe you can help us explain why the banks are failing right now.
I don't know, man.
It's been so long since I've been in that world.
What a different contrast, though.
The contrast between that world and the world that you live in now.
Dude, it's crazy to think about because I still know people that, you know, are
finance guys.
My brother's a finance guy.
Does he live in hell?
Yeah, well...
He can't be happy.
Yeah, yeah.
He's doing all right because he doesn't, you know, he doesn't...
All the investment strategies that he's do for the most part, like hedge type
of strategies.
But he's doing okay.
But, yeah, it's a different world, man.
It's definitely a different world.
Yeah.
Yeah.
And I always look back on my path and I think, like,
well, did I choose, you know, did I choose the right thing?
I don't know.
But I'm happy.
So, I guess, you know.
If you're happy, you chose the right thing.
But no one, there's no right thing.
There's just, like, life.
Life and decisions.
This idea that you're going to, like, oh, I wish I could do it differently.
Well, you definitely can't.
So, don't wish that.
There's no way you can do it differently.
Right.
Unless you have a fucking time machine.
And even if you have a time machine, you will already have the knowledge of
what happens if you do it wrong.
So, if you go back and try to do it right, who knows how you're going to fuck
that up.
Yeah, yeah, sure.
Like, it's not life.
That's, imagine living your life knowing what's going to happen if you do it
certain ways.
Like, that would be a terrible way to live.
Like, you'd be just, you would never be in the moment.
You'd be constantly filled with this anxiety of making sure that you don't do
the thing that you have already done.
Right.
So, that you could live your life in a different way.
I mean, I can imagine if, like, you know, you run a red light and crash into a
car and go, oh, my God.
How could I stop that from happening again?
I have to make sure I don't do that again.
Sure.
Things like that.
Yeah.
That makes sense.
Yeah.
But, like, a whole life path?
Yeah, yeah, yeah.
Like, change your whole life?
Yeah.
I wish I did it a different way.
Well, you definitely didn't.
So, keep going.
Right.
And, man, life's so path-dependent, you know, and that you get, you know, you
choose certain things and there's probably, like, a million different ways it
could go.
And, you know, that was, like, for me, there was a point in my life when I was
doing finance.
I was a trader when I was a young guy.
And, you know, there's just kind of a moment where I'm like, man, dude, I just
want to do something else.
And then you start down that path and it just, it leads you in wild places, man.
Well, literally, for you.
Yeah, yeah, yeah.
Well, sure, dude, look at me right here, where I'm at right now.
Like, you would have never, I would have never imagined this in my wildest
dreams, dude.
That's funny, but I meant wild places like the wild.
Oh, yeah, yeah, yeah, yeah.
You know, that, too.
Both things.
Both things are kind of wild.
Yeah, yeah, yeah.
Yeah.
So, how did you make this choice to, like, get off the path?
Because, for a lot of people, I think one of the problems with the path is you
get married, you get a house, you have kids, you have responsibilities, and
then you're stuck.
Because you really can't change careers because you have so many dependents.
There's so many people depending upon you.
You have so many responsibilities.
You have to kind of just suck it up and keep doing this thing that you don't
enjoy for your family.
Yeah, so to answer that question, man, I think I have to be a little humble
about it, Joe, because I came from a family, including my wife.
When I met my wife, man, like, I was a guy that was well-educated and looked
like a guy that was going to be on, like, a traditional path to, you know, to
great success as a finance guy.
And that's when I met my wife.
And then I, like, I tricked her, man, because I switched it up on her, you know,
but she stayed with me the whole time.
And so I got to give her that.
But also my family, too, man.
Like, you can imagine, like, you know, my parents, you know, wanted me to get a
great education.
I mean, they, my family, man, like, basically lived the American dream.
Like, none of them, they didn't grow up wealthy, you know, nor did I, but they
kept me comfortable.
And then, you know, they got great success and they wanted, they wanted, or
they got, you know, they got success through hard work.
And they wanted to see me, you know, have a path of, like, you know, go, go to
Wall Street, go be an attorney, go do something like that.
Because that seemed like the easy path, I think, in their mind and seemed to
make sense.
And they were giving me that opportunity.
But when I decided not to do that, man, not one time have my parents or my
brothers for that part said, like, dude, you're doing, you're being an idiot.
You know what I mean?
Like, when I told them, like, hey, I'm going to buy.
So, essentially, I bought an outfitting business that had been, you know,
pretty much run into the dirt, you know.
And it was just, it was just federal permitting where I could expand into a
bigger, you know, guiding business in Colorado.
When I told them I was going to do that, like, I was quitting my job at the
time.
And I was working, I was, I had transitioned working to working for a wealthy
family who treated me awesome.
But when I said, hey, man, I'm going to go be an outfitter, my parents were
like, I mean, my dad was like, sounds awesome.
You know, my brother was like, sounds awesome.
I can't, and I don't think that everybody grows up in a family that's that
supportive of it.
So, I don't want to say that, like, I, you know, did it all, like, I'm just a
guy that just said, hey, I'm going to do something cool and independent.
It was what I wanted to do.
And I had support, man.
So, I can't, I can't.
Well, that's very fortunate.
Yeah, yeah.
That's very fortunate.
So, what, how did you, so if you're in the middle of this world, this financial
world, how did you make that transition?
Like, what were the steps involved in making the transition?
Did you just immediately up and quit and just figure out how to get a job as an
outfitter?
Or were you already doing some outfitting?
Yeah, so, so I've been in, I mean, all through my childhood and, you know, and
then even when I was an undergrad in school, I hunted all the time.
And I had done a bunch of guiding and I was exposed to it.
And the other thing for my type of outfitting and guiding, I had been exposed
to livestock and horses and mules my whole, my whole life.
And that's a big part of, like, wilderness outfitting is you got to be familiar
with, you know, how to pack mules, how to pack horses, how to ride horses, you
know,
up in the mountains, because that's a huge proportion of what I, what I did
just to get into remote areas.
So, you know, not, not to dive, like, into the depth of my childhood, but I was
exposed to that, you know, the first 20 years of my life where, you know, I had
that skill set.
So, that's, that's the first part of it.
And then, you know, how I actually mechanically did it, I mean, so the, just to
give you some context, me and my brothers start when I was young.
At a business school, me and my brother started a financial company and it
changed, changed in a bunch of different ways and he still operates it.
But when I was, I think I want to say like 22, 23, I started working for our
biggest client.
And he was a phenomenal guy and I was doing more like family wealth management
for him.
And literally, Joe, I was, I was just kind of struggling day to day with being,
I always wanted to be in the outdoors and I wanted to go do something else.
And I literally just walked into his office and I was like, Bob, like, I love,
I love you, man, but I gotta, I gotta go.
Like, I gotta go do something else.
And I, and I kind of had a plan to get, to go back to Colorado.
I was born in the area, you know, where, where I did most of my outfitting and
guiding.
And it was funny because he looked at me and he kind of, he kind of laughed
because I think he knew it was coming.
Like he, he knew, he, he, uh, I mean, he came from a different world.
Like he'd grown in up, grown up, you know, grown up in, you know, um, doing
business deals and all that.
And I grew up from somewhere else.
And I think that's why he kind of enjoyed having me around.
Cause we would talk about, you know, our, you know, different backgrounds and
stuff, but he was just like, well, the first thing he said is like, Cliff, can,
I'm just going to ask you one time, man.
Can I give you more money?
And I'm like, Bob, we shouldn't even talk about it, man.
He's like, all right, dude, go for it.
Well, that's great.
So literally like a week later, me, me and my wife, we moved to Colorado and I
had a supportive wife.
Yeah, dude.
That's awesome.
Yeah.
I, uh, she, she's been epic.
The, the whole, the whole way.
So how did you go about starting and getting clients?
So if you're starting an outfitting business, you're a young guy, you're
leaving the financial sector and you're going and starting and getting clients.
How do you go about making that happen?
Yeah.
So, so part of the, part of how that, how that process worked for me is when I
got to Colorado, I started doing some packing and guiding.
This is, I mean, this is after I worked in finance.
So I took like, you know, kind of a, most people would say a step back to my
career, you know?
So one day I was like looking at financial models and trading and that sort of
thing.
And then three weeks later I was like helping guys pack, you know, elk out of
the wilderness on mules, you know, that sort of thing.
So, so I started getting exposed to it that way again.
Um, and then what, uh, what, what I did was I started just looking for a
business to buy.
And so you have to, there's, when you're operating in the wilderness areas, you've
got to have federal permitting.
So I got all that figured out, I bought a business and then it's just like hand
to hand combat, man.
Like you, I mean, the first year that I was guiding and outfitting, I think I
had, you know, maybe like a dozen clients or something like that.
The last year that, that I, that I outfitted, I had like north of 200 clients,
you know?
So it's just, it's just hand to hand combat.
And then, you know, as you learn an area and we can get into the nitty gritty
details of it, but these wilderness areas, th