August 12, 2025 • 7 mins
Comedian Drew Desbordes (Druski) speaks on his career and what he is working on. He speaks with Bloomberg's Romaine Bostick
See omnystudio.com/listener for privacy information.
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Goop over at Taylor Swift. You're not the only one
dropping big entertainment news today. You may have heard Fannie
that she's actually coming out with a new album. She
declined our request for comment, but we got the next
best thing. Drew Ski, the comedian, actor, entrepreneur and everything
in between, the multi hyphen it had a chance came
into the Bloomberg studios earlier today. We had a chance
to catch up with him and really talk about just
(00:20):
how much the entertainment industry has evolved, particularly for someone
like him. We got to start on social media and
is now kicking off an arena tour next month. Take
a listen.
Speaker 2 (00:31):
I'm actually very excited. Man. We've transitioned through a lot
of different stages of my career so far, and like
being able to say that this is my first arena
tour is like still mind blowing. But yeah, no, it's
definitely amazing. And we yeah, we're working on so much, man.
We got TV shows, now, we have a movie on
(00:52):
the way. Yeah, there's so much in store.
Speaker 1 (00:54):
So was it always your goal to be a comedian?
Was that what you grew up wanted to be?
Speaker 2 (00:58):
Yeah, I think I just didn't know when I was younger,
I used to just want to be funny in school,
but I got in trouble for it. So I was
kind of confused early on because I didn't really know
am I supposed to be doing this? You know what
I mean? Because everybody painted to be like a bad
thing in school. So yeah, it is. It is amazing
how it actually transpired throughout life. I had to figure
out what my purpose was.
Speaker 1 (01:18):
But yeah, no, I am curious about just the economics
of your business. I mean, we talk about the big
could A fests tour, but you have all these other shows,
dating show, the Cold a House Show, and I'm knowing
for getting a few others out there as well. But
you're producing all these yourself, right, yes, to your own company,
So effectively this is your business.
Speaker 2 (01:39):
Yes, you control it. Yes, one hundred percent ownership, that's
what we promote. Yeah, one hundred percent. No, but there's
there's a reason for it though, Like we I know,
I make the joke all the time, even with could
have been records that you know, we we. I do
enjoy doing it, but I mainly do it for the fans.
Knowing that I can do it myself now that I
(02:00):
have money from brand deals and people that I work
with in order to do it. It's like I don't
need another company to come in, which is cool. I
do enjoy that, but I think building my own IP
in this area is probably the most, like strongest thing
that I enjoyed developing.
Speaker 1 (02:15):
In the process from when you started to where you
are now, were you ever tempted to maybe sign or
take a job with a bigger company?
Speaker 2 (02:22):
Yeah, yeah, well there's some deals out there. I'm still tempting,
but I'm not saying it's not out the picture. But
the main thing I did start doing my own shows
and giving it for free on YouTube was because I
wanted to build something bigger by myself first, and then
you know, as things happen, we are actually we have
a lot of stuff coming up that will be with
(02:44):
other companies as well. But yeah, no, I think I
just wanted to build out my IP and like I
looked up to, you know, the Adam Sandler story of
how he built up Happy Madison and like just all
his movies and his production company, So I wanted to
do the same for mine.
Speaker 1 (02:58):
When you look at the opportunities out there for the
next Drewski whoever that may be and coming up. Do
you think that that path that you took will still
be there?
Speaker 2 (03:07):
Yes? With social media is so it's moving so fast,
and I think so many people are starting to find
out that they can do it themselves, which is why
I pride myself on what we have done. I hope
others will follow that same process and know that if
you are getting money from these companies, don't just think
that you have to go buy a car, or go
buy a big house, or go just splurge your money.
(03:30):
A smart thing you can do is try to build
your own IP and try to build your own business
around you. So what I would do, like, let's say Nike,
we work with Nike, So if Nike gives me a
million dollar check, I don't go and put that in
my pocket and try to go get a bunch of
cool stuff. I'll go and try to spend that money
on one of the episodes on my TV shows like
(03:51):
Yeah and Where It. Maybe it may sound crazy, but
like that money never goes just straight into the pocket.
I try to always reinvest.
Speaker 1 (03:58):
Reality mentioned Nike, I mean, you've had a lot of
brand partnerships, Beats by Dre, Nike, raising Canes, Mountain Dew, Google, Pixel, I'll.
Speaker 2 (04:08):
Probably forgetting a few Monster and Riz Picks is one
of the good ones. Wow.
Speaker 1 (04:12):
And so they all came knocking on your door wide
because you're so popular there.
Speaker 2 (04:18):
Just I don't think it's always my popularity. I think
they they may feel like I have that pull on
this next generation. Not to brag, I'm not. I'm not
a big brag. I'm just saying I do think I
also bring a good entertainment level to the brand deals
that I have been that we could do commercials on
TV or commercials for social media, and my fans they
(04:42):
adapt to it like they really do, like go and
buy the stuff whenever we drop anything. So I think
that that has probably worked out the best for me.
Speaker 1 (04:50):
There is some I mean, looking at some of the
clips that have been put out with some of these brands,
I mean there is a level of authenticity. I made
that word that I see in you what you do
compared to other influencers, And I wonder are you picking
sort of brands or products that you maybe use or
you have a love for, or are you kind of agnostical?
Speaker 2 (05:09):
Yeah, we're very picky about who we work with as well,
Like majority of my company for life is entertainment. We
try to make sure that we have a say so
in any of the stuff that we're putting out or
any of the commercial stuff. Like, we want to make
sure that this is just as funny as the content
that I'm putting out by myself. So yeah, that's definitely
marked in the contract before we sign anything with any company,
(05:32):
is to make sure that we have say so on
any creative.
Speaker 1 (05:35):
I do have to ask you about just the idea
of protecting your reputation and in the context obviously for
a Nike or raising knees to whoever, these big brands
are taking a risk, right, I mean, normally they like
to play it safe. They want to make sure that
the people they're aligned with are going to say, you're funny.
But you've had a few jokes, a few sketches that
didn't quite land the right way. You got some pushback.
(05:58):
So how do you navigate that? I mean, because you're
trying to sort of, you know, not be controversial, but
be provocative.
Speaker 2 (06:04):
Well, yeah, I think a lot of stuff and I
appreach about this, like relationships are key, and you know,
with comedy, they have to understand that comedy is comedy,
and sometimes you do have to walk that line of
what's funny and what's too far. So I think with
having a good relationship with some of these brand partners
(06:25):
or some of like you know, some of the higher
ups in that company, they understand like, Okay, this is
this is fine, and we trust him in this because
we know this is how we found him. So being
able to have these conversations with some of the higher
ups of these companies, it's like, Okay, they do have
a certain sense of trust that Okay, this is Yer
Ski and this is why we love him. So we
(06:46):
can't cut ties because maybe we see a skit was
too far, or maybe this was this joke was too
far left. So it's worked good just off of just
having good relationships with majority of the people that we
work with.
Speaker 1 (06:58):
I mean, how do you see social media comedy, Instagram
comedy evolving?
Speaker 2 (07:03):
It's had it in a great direction. I think social
media now with just the streaming stuff and like the
twitch world and us getting into that. So now I'm
starting to develop even pivoting my content into the streaming
world and like how that works. So yeah, it's definitely
headed in a good direction though for sure.
Speaker 1 (07:22):
That was my conversation with the comedian and entrepreneur Drewski.
I always just want to point out Bonnie that last
question that I asked him. My son gave me that
question because I think of all the guests I've had
on the show, on all the years I've been on
this network, this was the one he cared about most.
We could have David Solomon, Jamie Diamond, and Jamie Fraser
around the table, he would not have cared Drewski. Yeah,
he's tuning it out. He's sixteen, sixteen
Speaker 2 (07:44):
All right, Okay,
Goop over at Taylor Swift. You're not the only one
dropping big entertainment news today. You may have heard Fannie
that she's actually coming out with a new album. She
declined our request for comment, but we got the next
best thing. Drew Ski, the comedian, actor, entrepreneur and everything
in between, the multi hyphen it had a chance came
into the Bloomberg studios earlier today. We had a chance
to catch up with him and really talk about just
(00:20):
how much the entertainment industry has evolved, particularly for someone
like him. We got to start on social media and
is now kicking off an arena tour next month. Take
a listen.
Speaker 2 (00:31):
I'm actually very excited. Man. We've transitioned through a lot
of different stages of my career so far, and like
being able to say that this is my first arena
tour is like still mind blowing. But yeah, no, it's
definitely amazing. And we yeah, we're working on so much, man.
We got TV shows, now, we have a movie on
(00:52):
the way. Yeah, there's so much in store.
Speaker 1 (00:54):
So was it always your goal to be a comedian?
Was that what you grew up wanted to be?
Speaker 2 (00:58):
Yeah, I think I just didn't know when I was younger,
I used to just want to be funny in school,
but I got in trouble for it. So I was
kind of confused early on because I didn't really know
am I supposed to be doing this? You know what
I mean? Because everybody painted to be like a bad
thing in school. So yeah, it is. It is amazing
how it actually transpired throughout life. I had to figure
out what my purpose was.
Speaker 1 (01:18):
But yeah, no, I am curious about just the economics
of your business. I mean, we talk about the big
could A fests tour, but you have all these other shows,
dating show, the Cold a House Show, and I'm knowing
for getting a few others out there as well. But
you're producing all these yourself, right, yes, to your own company,
So effectively this is your business.
Speaker 2 (01:39):
Yes, you control it. Yes, one hundred percent ownership, that's
what we promote. Yeah, one hundred percent. No, but there's
there's a reason for it though, Like we I know,
I make the joke all the time, even with could
have been records that you know, we we. I do
enjoy doing it, but I mainly do it for the fans.
Knowing that I can do it myself now that I
(02:00):
have money from brand deals and people that I work
with in order to do it. It's like I don't
need another company to come in, which is cool. I
do enjoy that, but I think building my own IP
in this area is probably the most, like strongest thing
that I enjoyed developing.
Speaker 1 (02:15):
In the process from when you started to where you
are now, were you ever tempted to maybe sign or
take a job with a bigger company?
Speaker 2 (02:22):
Yeah, yeah, well there's some deals out there. I'm still tempting,
but I'm not saying it's not out the picture. But
the main thing I did start doing my own shows
and giving it for free on YouTube was because I
wanted to build something bigger by myself first, and then
you know, as things happen, we are actually we have
a lot of stuff coming up that will be with
(02:44):
other companies as well. But yeah, no, I think I
just wanted to build out my IP and like I
looked up to, you know, the Adam Sandler story of
how he built up Happy Madison and like just all
his movies and his production company, So I wanted to
do the same for mine.
Speaker 1 (02:58):
When you look at the opportunities out there for the
next Drewski whoever that may be and coming up. Do
you think that that path that you took will still
be there?
Speaker 2 (03:07):
Yes? With social media is so it's moving so fast,
and I think so many people are starting to find
out that they can do it themselves, which is why
I pride myself on what we have done. I hope
others will follow that same process and know that if
you are getting money from these companies, don't just think
that you have to go buy a car, or go
buy a big house, or go just splurge your money.
(03:30):
A smart thing you can do is try to build
your own IP and try to build your own business
around you. So what I would do, like, let's say Nike,
we work with Nike, So if Nike gives me a
million dollar check, I don't go and put that in
my pocket and try to go get a bunch of
cool stuff. I'll go and try to spend that money
on one of the episodes on my TV shows like
(03:51):
Yeah and Where It. Maybe it may sound crazy, but
like that money never goes just straight into the pocket.
I try to always reinvest.
Speaker 1 (03:58):
Reality mentioned Nike, I mean, you've had a lot of
brand partnerships, Beats by Dre, Nike, raising Canes, Mountain Dew, Google, Pixel, I'll.
Speaker 2 (04:08):
Probably forgetting a few Monster and Riz Picks is one
of the good ones. Wow.
Speaker 1 (04:12):
And so they all came knocking on your door wide
because you're so popular there.
Speaker 2 (04:18):
Just I don't think it's always my popularity. I think
they they may feel like I have that pull on
this next generation. Not to brag, I'm not. I'm not
a big brag. I'm just saying I do think I
also bring a good entertainment level to the brand deals
that I have been that we could do commercials on
TV or commercials for social media, and my fans they
(04:42):
adapt to it like they really do, like go and
buy the stuff whenever we drop anything. So I think
that that has probably worked out the best for me.
Speaker 1 (04:50):
There is some I mean, looking at some of the
clips that have been put out with some of these brands,
I mean there is a level of authenticity. I made
that word that I see in you what you do
compared to other influencers, And I wonder are you picking
sort of brands or products that you maybe use or
you have a love for, or are you kind of agnostical?
Speaker 2 (05:09):
Yeah, we're very picky about who we work with as well,
Like majority of my company for life is entertainment. We
try to make sure that we have a say so
in any of the stuff that we're putting out or
any of the commercial stuff. Like, we want to make
sure that this is just as funny as the content
that I'm putting out by myself. So yeah, that's definitely
marked in the contract before we sign anything with any company,
(05:32):
is to make sure that we have say so on
any creative.
Speaker 1 (05:35):
I do have to ask you about just the idea
of protecting your reputation and in the context obviously for
a Nike or raising knees to whoever, these big brands
are taking a risk, right, I mean, normally they like
to play it safe. They want to make sure that
the people they're aligned with are going to say, you're funny.
But you've had a few jokes, a few sketches that
didn't quite land the right way. You got some pushback.
(05:58):
So how do you navigate that? I mean, because you're
trying to sort of, you know, not be controversial, but
be provocative.
Speaker 2 (06:04):
Well, yeah, I think a lot of stuff and I
appreach about this, like relationships are key, and you know,
with comedy, they have to understand that comedy is comedy,
and sometimes you do have to walk that line of
what's funny and what's too far. So I think with
having a good relationship with some of these brand partners
(06:25):
or some of like you know, some of the higher
ups in that company, they understand like, Okay, this is
this is fine, and we trust him in this because
we know this is how we found him. So being
able to have these conversations with some of the higher
ups of these companies, it's like, Okay, they do have
a certain sense of trust that Okay, this is Yer
Ski and this is why we love him. So we
(06:46):
can't cut ties because maybe we see a skit was
too far, or maybe this was this joke was too
far left. So it's worked good just off of just
having good relationships with majority of the people that we
work with.
Speaker 1 (06:58):
I mean, how do you see social media comedy, Instagram
comedy evolving?
Speaker 2 (07:03):
It's had it in a great direction. I think social
media now with just the streaming stuff and like the
twitch world and us getting into that. So now I'm
starting to develop even pivoting my content into the streaming
world and like how that works. So yeah, it's definitely
headed in a good direction though for sure.
Speaker 1 (07:22):
That was my conversation with the comedian and entrepreneur Drewski.
I always just want to point out Bonnie that last
question that I asked him. My son gave me that
question because I think of all the guests I've had
on the show, on all the years I've been on
this network, this was the one he cared about most.
We could have David Solomon, Jamie Diamond, and Jamie Fraser
around the table, he would not have cared Drewski. Yeah,
he's tuning it out. He's sixteen, sixteen
Speaker 2 (07:44):
All right, Okay,
Popular Podcasts
Law & Order: Criminal Justice System - Season 1 & Season 2
Season Two Out Now! Law & Order: Criminal Justice System tells the real stories behind the landmark cases that have shaped how the most dangerous and influential criminals in America are prosecuted. In its second season, the series tackles the threat of terrorism in the United States. From the rise of extremist political groups in the 60s to domestic lone wolves in the modern day, we explore how organizations like the FBI and Joint Terrorism Take Force have evolved to fight back against a multitude of terrorist threats.
Dateline NBC
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
NFL Daily with Gregg Rosenthal
Gregg Rosenthal and a rotating crew of elite NFL Media co-hosts, including Patrick Claybon, Colleen Wolfe, Steve Wyche, Nick Shook and Jourdan Rodrigue of The Athletic get you caught up daily on all the NFL news and analysis you need to be smarter and funnier than your friends.