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July 10, 2025 22 mins

You can't break out by trying to fit in! That's the mantra we’re diving into today as we chat with the hilarious Jimmy Failla, who’s gone from New York City cab driver to comedian to comedy radio kingpin, middays on his network FOX Across America show...which has exploded onto another 10+ stations just since we recorded this interview!

We’re talking all about how you have to be your unique self in a world that’s constantly trying to squeeze you into a box. Simple, but not easy. Jimmy shares his wild journey and how he crafts his show, blending humor with the serious stuff, like current events and even politics — you know, the fun topics! Plus, we’ll get into the nitty-gritty of how to connect with audiences across different platforms, including his top-rated TV Show and best-selling books!

So, grab your earbuds, kick back, and let’s explore the art of being a one-of-a-kind voice in this crazy media landscape!

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
You can't break out by tryingto fit in.
So don't look around you andtry to just be a part of what you
see working.
Try to be that unique thingthat you are.
Cause that's what Rush was, to whatever.
Extent you are too.
Jimmy.
Well, thank you.
But I say that knowing that'smy background in stand up Brand with
On Demand.

(00:21):
Rebooting radio with adifferent take on all radio can be.
You know, there's so manystories about how the station you're
on might change itsprogramming directive and there you
went, or something like that.
So if you can startestablishing, it's almost like these
side businesses for us, theseturnkey businesses, you can leverage
these platforms into othergrowth streams.

(00:42):
Because the one thing I'lltell anybody who followed comedy,
the old adage goes, in comedy,we get paid weekly, very weekly.
You know, so you get creative.
Now, your guides through themedia morphosis, David Martin and
author of the book Brand withmedia branding coach Kipper McGee.
Hey.
This time, kids, we're divinginto the world of comedy media and

(01:05):
a new take.
A brand new, fresh take ontalk radio.
Our guest has mastered the artof blending humor with sharp insights,
transitioning from a New YorkCity cab driver to a standup comedian.
And now a celebrated media personality.
Known for his witty takes oncurrent events, he's become a fresh
voice in American media,reaching audiences nationwide with

(01:27):
his syndicated radio show.
Now he's taking center stageonce again with his own show on the
Fox News Channel, offering acomedic break from the week's headlines.
Today we explore his journey,his take on the media landscape,
and his vision for the futureof broadcast comedy.
In a time of deep divides,Brand, with On Demand is proud to

(01:48):
welcome the network radio hostof Fox across America and TVs Fox
News Saturday night, Jimmy Fallon.
Crowd goes wild.
Yeah, thank you for thatflattering intro.
You read it just the way Iwrote it down.
Of course we did.

(02:09):
So, Mr. Fearless, sir, from.
From cab driving to comedy andradio, what key lessons have you
learned about connecting witha variety of audiences across different
platforms or even the sameaudiences in different venues?
Let me give you this, okay?

(02:30):
I have a superpower for real.
This matters.
Okay.
And it's the fact that I'vespent so much time in the consumer's
position as a cab driverbecause you understand when you're
driving a taxi in New YorkCity, you're either getting cut off
or shot at, or you're justdriving along listening to the radio.
So when I wasn't talking tohobbits, and time travelers, you

(02:53):
know, and people teleportedinto my taxi from other dimensions.
Seriously, anybody who tellsyou we don't have life on other planets
has never driven a taxi in NewYork City.
Okay, I've met it all.
But the one thing I can tellyou, okay, especially when it.
As it pertains to radio, is ifyou're behind the wheel for 12 to
15 hours a day, as I was sixdays a week, you're consuming an

(03:14):
awful lot of radio.
And what you come to quicklyunderstand, and this probably travels
into other content mediums aswell, is we're all kind of in the
companionship business.
And what I mean by that is Ialways tell people who are trying
to get into radio you'restarring in a buddy cop movie.
When you host a radio show.

(03:35):
Every.
Every one of those buddy copmovies begins with a guy getting
into the squad car, hearing anew partner's voice, and fighting
whether or not he can ridealong with that guy and fight crime.
Well, the key to being a goodradio host is people have to want
to spend time in the squad carwith you and vibe.
If the atmosphere you'recreating leaves them angry or filled

(03:57):
with some type of angst orhostility, then your space becomes
hard to inhabit, and theyeventually ask the sergeant for a
transfer, which in this caseis them just changing the station.
So my superpower is that Itake the air every day as a listener
a lot more than I do as a host.
Great stuff, Jimmy.
Your radio show, Fox AcrossAmerica really creates a new kind

(04:20):
of talk radio, blending humorwith current events and common common
sense and, yes, even some politics.
Plus all those wacky drop ins.
How do you balance being funnywhile tackling serious issues?
And how did this concept come about?
Well, a lot of it, to answerboth questions, is the drugs.
Obviously, you know, we got alot more bandwidth than we know.

(04:45):
I'm kidding.
Again.
The process for me of what I'mtrying to do when it comes to radio
is I'm trying to put theirvitamins in their applesauce.
Do you know how they trick akid into taking the vitamins he doesn't
want?
Or they trick the dog intotaking the vitamins they don't want
by burying it in somethingsweet that they'll enjoy.

(05:05):
That's essentially what I'm doing.
I'm tasked with covering hardnews for three hours a day, but I'm
trying to be mindful of thedigestion process.
So that was the brainchild forall of these sound drops that I play
and song parodies and Sketchesthat I write is I want to make this
stuff more accessible, meaningemotionally accessible.

(05:26):
I want it to feel good going down.
So it's amazing because I'vechronicled what often feels like
we're starring in the seriesfinale of America.
We've had such a great timedoing it that I don't think a lot
of us realize they're now, youknow, the Statue of Liberty is basically

(05:47):
selling feet pics for allintents and purposes, Right?
You're listening to my show,you feel good about it.
You're like, well, they'regoing to be big feet, but I'll buy
a pair.
I think I'll buy a pair.
Yeah.
Funnier if that weren't so true.
Wow.
Okay.
I gotta ask you one thingabout all the sound effects and drop
ins and stuff.
I mean, how do you collect allthose things?
And more importantly, how doyou play them?

(06:08):
Do you do the buttons or doyou have them?
I, I, you know what I, I do, Iplay them myself.
So I have 10 pages of drops onan Enco page.
So let's say each page has ahundred drops is I add about eight
or nine of them every week andget rid of some and add new ones.
But I know where they are inreal time and I'm playing them off

(06:28):
a mouse.
So when I'm talking to you, Ihave an idea in my head of the point
I'm trying to make.
So there's two conversations,the one I'm having out loud and the
one I'm having in my headabout what might accentuate a point
I'm trying to make, what mightbreak this up a little bit.
That is all me in real time,but it's completely improvisational

(06:49):
in the sense that, yes, I knowwhere these drops are in my head.
No, I don't get on the micwith any plan for an individual break
because I need this to sound organic.
And for me, I'm better attrusting my average than I am at
scripting my average.
Do you follow what I'm saying?
Yep, absolutely.
1,000%.

(07:10):
Yeah.
Good.
Yeah.
Like when.
What I mean is, if thesestations knew just how unprepared
this show is, none of themwould clear it, but it actually works
better.
I mean, we started on 27stations, we're on 160 stations,
which, I know there are biggershows, but that's a lot of growth
because we've grown with a lotof independent stations picking us

(07:31):
up just because the atmosphereis a better way of digesting talk
radio.
Yeah.
So on that note, given allthis experience both on stage and
on air, what in your mind doesit take to make a great segment?
Whether it's radio, podcast,tv and how do you decide which topics

(07:55):
are worth your time incovering and making it to the show?
My primary focus, okay.
Is to filter it through thelens of not radio or TV host Jimmy,
but through cab driver Jimmy.
Meaning does this story impactcab driver Jimmy?
Is it about crime or safety orthe economy or the quality of local

(08:17):
education?
Is it something that has adeliverable for the consumer?
Because the truth is, in orderfor them to care about it a lot,
number one, it has to relateto them.
But you need to care about it.
And for that reason, it'sweird, but I find more fun in topics
that might seem heavy than Ido in topics that might seem superficial.

(08:39):
If only because you care aboutthat heavy topic and how it affects
people.
Like, I can give you two greatminutes on whether or not JD Vance
wears eyeliner, but hisability to put on eyeliner doesn't
affect your ability to payfor, you know, groceries.
Right.
I'm usually having more fun inthat serious area than I am in that
superficial area.

(08:59):
But I think the.
It's the deliverable metric.
Does this offer a tangibledeliverable or an impact on the listener's
life?
And I think that was a lesson learned.
I mean, this for the 2016 election.
I came into that election as acab driver.
I came out of it as someonewho was starting to appear infrequently
on tv.
But the one thing I wasn'tsurprised by was the outcome.

(09:21):
Because I knew for as much asthe media was dissecting Trump's
tweets and his attitudetowards debate moderators and stuff
of that nature, I knew theboots on the ground were hearing
a different story.
They were hearing things aboutjobs, you know, and maybe about America
not getting ripped off by ourenemies or allies alike and certainly
border security.

(09:41):
That resonated with people.
And in my head I was like,wow, I'm actually more equipped to
do this than most of these socalled experts because the experts
analyze along the lines ofwhat the other experts are talking
about.
So I try to be just mindfulof, again, cab driver Jimmy would
care about this, whereas TVJimmy is around people who might

(10:03):
care about that.
Now, to be honest, I'm notaround anybody because I need an
extra hour a day in the makeup chair.
Yeah, okay.
I'm in a different lane.
Most of these people on Foxlook like TV stars.
I look like I installed your tv.
Okay.
But that's Another superpower.
It's relatability, man.
I'm one of them, not one ofthe TV people.

(10:25):
I'm one of the listeners.
Absolutely.
With your success, Jimmy, onradio and certainly on cable too,
in addition to your standup,do you see any emerging trends in
media that content creatorsthat are working in audio and video
or whatever other distributionplatform they happen to be on should
be thinking about?
What do you see coming next?
All right, two things.

(10:46):
Okay.
One is we're in a reallyfragmented landscape when it comes
to content consumption.
It's fragmented in a way it'snever been before.
People used to have a fewbasic options for entertainment now
because the portability aspectof the phone means everything is
in play.
And the truth is people aregravitating towards things, number

(11:09):
one, that make them feel good.
There's a very limited marketfor anger.
There's a very limited marketfor bile and hostility.
And I think you are uniquelypositioned as a broadcaster right
now.
If you can tell people, youdon't have to tell them what they
want to hear.
You don't need to be in aconfirmation bias business, but they
need to personally trust you.

(11:29):
I think it's become moreintimate now and that people do have
an intimate relationship withevery host they consume because they
not only see you on TV or hearyou on radio, they're now looking
at a picture of your dinner on Sunday.
They're now it's ball gamefinding out whether or not Lincoln's
team covered the spread.
As I'm so focused on.

(11:50):
So I think the truth is you'rea companion now more than you are
just a host.
I think you are a lifestyle.
And I think if your lifestyleis agreeable, like you're kind of
cool and they know you'rebargaining with them in good faith,
they'll take a lot of rideswith you that they wouldn't traditionally
take with other hosts ifthey're genuinely of the mind that

(12:11):
you are this thing you'representing to them.
So authenticity is number one.
That's really, really big.
But number two is entertainment.
And this is what's really sooverlooked by Rush Limbaugh is so
many guys came along and triedto kind of ape his style, and that
might have meant militantpolitical analysis, but Russia's

(12:33):
superpowers.
He was a great entertainer andpeople, and I can tell you this,
as a cab driver, found him tobe a great companion in the car.
He was somebody you could ridealong with and fight crime every
day.
And self awareness to theshow, even when it was a self Awareness
to how obnoxious he was being.
He'd be like, yeah, we got totake another obscene profit break.

(12:54):
You know.
But people found thatendearing because he was leaning
into the reality of who he was.
So I think for people who aretrying to break through this very
fragmented landscape, okay,you can't break out by trying to
fit in.
So don't look around you andtry to just be a part of what you
see working.

(13:14):
Try to be that unique thingthat you are.
Because that's what Rush was,to whatever.
Extent you are, too.
Jimmy.
Yeah, well, thank you.
But I say that knowing that'smy background in standup.
So really quick, and you guysmight appreciate this, you know,
prior to me coming to Fox,getting my own show, obviously in
comedy, I was the guy whowould go on before the guy you had

(13:35):
actually heard of.
You know, there's.
There's a two drink minimum.
You're gonna need both of themto get through my act.
And you're the middle, right?
And then the guy you wanna seeis coming on stage, and that's kind
of where I started.
And that's fine.
But that leaves you in thegreen room having a lot of conversations
with other celebrities thatmight be friends with the celebrity
you're opening for.
Well, one of the things Larry David.

(13:55):
Larry David Kirby, Enthusiasm,Seinfeld, Larry David told me is
he said that his character onCurb youb Enthusiasm is who he wishes
he could be in real life.
Meaning in real life, he's notthat confrontational, he said, because
someone would have shot him by now.
Because the law of averagessay you can't get into an argument
over every innocuous thingjust because he said, basically in

(14:19):
defining his TV and mediaPersona, that's who he would be.
In a world of zeroconsequence, how does he really feel?
And TV was his opportunity toact out on it.
Well, if you want to breakthrough as a broadcaster, you really
have to look at yourself that way.
How would you be in a worldfree of consequence?
And I know people might say,but hold up, there's consequence,

(14:41):
there's censorship, there's everything.
But if you're bargaining withyour audience in good faith and you're
operating free of any type ofmalice or malicious intent, there
almost isn't consequence anymore.
Okay?
There isn't.
You know, we're kind of pastthat now because we don't have the
luxury of policing speech theway we did two years ago, four years
ago and eight years ago.

(15:03):
Like, if you notice, nobody'scanceling comedians anymore because
they're too busy working asecond job to pay for groceries.
The culture is a luxury.
So be the superhero version ofyou would be my advice to anybody
who wants to break through.
And speaking of that, Jimmy,it seems that more and more broadcasters,
and particularly those withspoken word chops, morning shows

(15:25):
on music stations and talkhosts, it's more common that they
are doing live shows with somesort of audience, a studio audience,
or maybe they're doing acomedy show or something like that.
Is that becoming more and morepart of a host revenue portfolio?
Should local hosts and contentcreators, what should they be doing

(15:47):
to secure their longevity in achanging media landscape where their
pay might be flattening oreven decreasing from the radio gig?
Yeah, you should absolutelylook out into those alternative streams
of revenue.
Like if you have the abilityto do a live act.
Okay, whatever that live actmight, you might not be a comedian,

(16:09):
but let's say you're a radiohost and you just want to have like
a town hall where you takequestions or you just want to do
a live version of the showwhere people get to interact with
it, then yeah, I would explorefinding a venue that might partner
with you on the proceeds andputting something together because
one, it builds yourrelationship with your audience and
that you get to meet them sothey have a bigger investment in
you.

(16:30):
But two, it does create yourability to generate revenue independently
of fickle overseers.
You know, there's so manystories about how the station you're
on might change itsprogramming directive and there you
went or something like that.
So if you can startestablishing, it's almost like these
side businesses for us, theseturnkey businesses, you can leverage

(16:52):
these platforms into othergrowth streams.
So yes, it is imperative thatpeople do that.
If you can get to bookwriting, anything you can do that
gives you that flexibility.
Because the one thing I'lltell anybody who followed comedy
is the old adage goes, incomedy, we get paid weekly, very
weekly, weekly, you know, soyou get creative.

(17:15):
We are with the incrediblyentertaining Jimmy Fader.
What a guy.
He's a network radio host ofFox Across America on radio and on
cable tv, Fox News Saturday night.
Know someone who'd be a greatguest or have an idea for a topic
we ought to cover?
Well, let us know.
Reach out via email, shout outshow@brandwithondemand.com or follow

(17:40):
us on social brand with plus.
That's on Instagram, Facebookand X.
Brand with plus.
P L U S brand with plus.
And if you're new here, wejust want to say welcome and don't
forget to hit the Followbutton on your podcast app.
And for our returning folks,please share the podcast with a friend

(18:01):
and give us a five star reviewwherever you get this brand with
On Demand helping you perfectyour audio and omnichannel skills.
Coming up, Jimmy Fala revealssomething that Fox forgot to tell
him during the job interview.
Here at Music Master, we canhelp with a lot of things because

(18:23):
we've heard a lot of things.
Have you ever heard this?
Of course you have.
It's dead air.
Or how about this because cuzyou left me.
Yeesh.
What's known as the trainwreck Segway.
Or maybe your PD just heardtwo of the same artists back to back
and it's not even Tuesday.
At Music Master we know athing or two because, well, we've

(18:47):
heard a thing or two.
We are Music Master Perfect.
The sound of your radiostation today.
Check out musicmaster.comwondering how to put.
AI to work for you?
Well, here's a must have tool.
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(19:09):
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Get details and a free sevenday trial now.
Radiocontentpro.com what theydidn't tell you at.

(19:31):
The job interview brand withOn Demand.
Now we're talking with NewYork cab driver turned comedian turned
radio and cable TV star Jimmy Fayla.
Jimmy, thinking about movingto radio and tv?
What's the one thing they forget?
Got to tell you in the job interview.

(19:52):
That you're not allowed to eatcarbs anymore.
That was a big, that was a,that was a big, that was a big breakthrough
in tv.
They have me walking aroundwith a shock collar on so I stop
eating food.
But no, to be serious, here'sthe truth.
Radio is better than TV ifyou're actually trying to have a
good, productive conversationbecause you have a lot more room

(20:14):
in the break.
What nobody tells you makingthat jump from radio to TV is just
how finite the time is on the air.
Like you think about it.
When you have a guest on yourradio show, you're going to talk
to this guy for 8 minutes, 10minutes, 12 minutes, 15 minutes if
you have room, okay?
In TV, the guy's on for three minutes.
There's a different story thanthe one you're talking about streaming

(20:36):
across the bottom of thescreen and a picture in the corner
of the guy.
Coming up next.
It is such a smash and grabmedium that there's an efficiency
to tv.
Okay.
That really does help you inradio become a more targeted broadcaster,
but really does often deny theconsumer a more fleshed out discussion

(20:56):
because it's like, what do you got?
Why do you got it?
Who's coming up next?
We'll be right back.
So that's the biggest changeis the management of time as a broadcaster.
So I prefer radio better for substance.
I prefer TV just in terms ofas a comic, you know, your ability
to do visual things.

(21:17):
Sure.
Absolutely.
Great stuff, Jimmy.
Great stuff.
Our thanks to the verytalented Jimmy Filo.
We have links to his podcast,the TV show, his books and more all
in the show notes.
Just scroll down on your phone.
Kudos to exec producer CindyHuber for incredible coordination

(21:37):
all the time and our associateproducer Hannah B For only booking
the best.
Speaking of which, coming upnext, omnx.
Brand with On Demand.
It's me, Scott Bertram,general manager of wrfh, Radio Free
Hillsdale at Hillsdale Collegeand lecturer in journalism.
Here.
We'll talk a bit about the thenext generation of radio and audio

(22:01):
talent.
I'll talk a bit about substackand my podcast on 50 years of Saturday
Night Live.
All that coming up on the nextBrand with On Demand.
That's a wrap, Kipper.
It's all about company beinggood company, a good companion.
It's really a secret tosuccess in the show.
Notes@brandwithondemand.comI'm Dave Martin.

(22:24):
And I'm Kipper McGee.
May all your brand width be wide.
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