Name: Kevin O'Leary: Firing Employees GONE WRONG
Uploaded: 2025-12-25T14:00:12.000Z
Description: Watch the stand-up comedy video 'Kevin O'Leary: Firing Employees GONE WRONG' from TAFS Clips on Comedy Buff. Published 2025-12-25. Transcript available.

Watch the stand-up comedy video 'Kevin O'Leary: Firing Employees GONE WRONG' from TAFS Clips on Comedy Buff. Published 2025-12-25. Transcript available.

You just played music for us. You're a guitarist. You're a photographer. You're
now an actor.
You are a documentarian. You've made a documentary film before in your early
years.
You are an entrepreneur. You are kind of an elder statesman of business in
North America, I'd say.
Would you consider yourself a modern-day renaissance man or like a da Vinci of
sorts?
You know, the journey of entrepreneurship is not a destination. It's a journey.
And the reason you would want to do that now, and I tell everybody this,
because I teach entrepreneurship at places like MIT and Harvard now,
it's not about the greed of money because you just listed off a bunch of things
I couldn't do if I wasn't free to do them.
That's what money buys you, the free time.
It's not about the greed of money. I don't need more money.
I need more time to pursue the things that really interest me.
So what you find out is that if you're motivated by money as an entrepreneur,
you will never get it.
Right.
You have to be so insanely passionate about what you're doing, and all the
competitors are pursuing you.
And then one day you wake up and you're filthy rich.
That's how it happens.
Every guy I've ever talked to that's had a huge exit has said, I never saw it
coming because I was just myopically focused on my business.
It was the same for me.
And then one day we were acquired for $4.2 billion.
And then what I found was amazing for all of us, the people, the nine core
people, we didn't know what to do the next day.
We just went back to work.
I mean, that's all we know.
And so we just kept doing other things, and I've done many other successes and
failures in that period.
But, you know, it's allowed me to do some really interesting things, and that's
what keeps me going and, you know, pursuing stuff.
Uh-huh.
Yeah.
It's very interesting.
Yeah, yeah.
But you have to be able to afford the time, right?
The time is the problem.
You can't buy any.
I mean, that's the one thing, no matter how rich you get, you can't buy.
You can't buy health, and you can't buy, you know, you can't be guaranteed
health.
You've got to be very careful, and I certainly think about that a lot.
And I do try and use my time very carefully because I don't have to do anything.
So I'm kind of, I'm here because I want to be here, and so I block this because.
You're a big fan.
Yeah, well, also, I just, you guys do interesting work.
I've seen some of it, and it's interesting, and I thought this could be good.
So, you know, that's why.
And then I'm going to do some other crazy shit tonight, and.
What's that?
I'm going to have a dinner with the auctioneer of the F.P. Journe Francis Ford
Coppola watch,
which I put on television about an hour ago.
Oh, wow.
Yeah, it's probably the most coveted watch on earth.
It's probably going to sell on Saturday for between three and five million
dollars.
I wanted to hold it in my hand before it went into a private collection for a
generation.
So I suggested we bring it to television.
Did you consider stealing it?
Yeah, the problem with that is I know Journe.
I'm wearing one of his watches.
He's, the thing about watchmaking, which I really learned as time passed, is
collectors
now covet the independent watchmaker.
And Journe is now considered a living Picasso.
He is making only 900 watches a year.
There are thousands of collectors around the world that want a Journe.
But he personally decides who gets each piece.
Really?
Yeah.
And so...
And they cost, what, over a thousand dollars probably?
What's funny about that?
Yeah, the secondary market would be in the millions.
Whoa.
Primary, you can get one as inexpensive as 18,000, but you can't.
I mean, that's the problem.
The Elegant, which is the entry-level watch, sells for 18,000, secondary market
is 158,000.
And that's a beautiful piece.
Pretty simple.
I want to try something, because this is kind of a free education for me.
Because I'm a new entrepreneur, I'm an entrepreneur of sorts.
I don't think of myself as one.
I'm kind of a...
Well, you're supporting yourself with what you do.
I have a staff now, and I...
Yeah, you have a responsibility.
Yeah, and they look up to me, and they see me as a friend more than a...
I bet some of them think you're an asshole.
That's probably true.
No, I think that they think...
Well, okay.
One thing that I've struggled with, and maybe you can, as an educational thing
for the audience,
you can kind of impart some wisdom on me, is firing.
Like, I don't, like, I've...
There is one individual who's not here today.
Because you whacked him?
No, because I...
And I've...
It's probably been a matter of three months that he should have been fired.
But every time I get close, I just don't have it in me.
So, perhaps if we could, like, act it out, you could kind of show me...
You could be me, I'll be him.
And then you could kind of, like...
Because I really...
I don't know how to do this.
I called my girlfriend's dad and said, how do you fire...
What's his name?
Paul.
Okay, so you're Paul.
No, no, the guy?
Yeah.
Oh, uh, yeah.
He's not here right now, also.
You know, I get it, but I'm going to give you...
Here's how it goes down.
You know, I want you to be happy.
I really want to be...
I want you to be happy.
And I have a feeling you're not happy.
And the reason I feel that way is you're not with the team anymore.
You're not on the same agenda.
And that must be that you're not happy.
Now...
I'm happy.
I'm fine.
I like it.
Well, the team isn't happy with you because they feel you're not happy.
And I'm going to make it very simple for you.
We're going to end our relationship today, but the good news is I'm going to
give you
a fantastic exit package because I want you to be fairly treated.
That's number one.
How much?
How much?
And number two is, you know...
How much is the exit package?
I'm going to pay you three months of your salary.
Okay.
I don't have to.
I could pay you six weeks.
To be a good guy because I'm a good guy.
Listen, that's why they call me Mr. Wonderful.
Yeah.
So I'm going to give you three months.
Do I call myself Mr. Wonderful?
But what's important is that we go our own ways now.
I don't want you sitting around.
In fact, I've cleaned out your whole place.
There's a box outside on the street.
It's waiting for you.
Yeah.
Okay.
But I've got you a limo.
The box is in the limo and it's going to take you wherever you want.
Okay.
Can I just do that right now?
I swear to God.
Yeah.
Yeah.
I mean, you did.
Well, that's how you do a fair...
A fair...
Yeah.
A shit can.
Okay.
I mean, I'll be nice about it, but...
Okay.
I mean, just give me a minute.
I know we're pressed for time, but I'll just get him out of here.
Because this has been driving me nuts.
Well, I think you've got to make a decision.
That's my whole point.
Hey.
Hey.
Hello?
Hey, where are you?
I'm home.
I'm home right now.
Yeah.
Well, why aren't you here right now?
Um, no, I had a family emergency.
It's a fucking...
Hold on one second.
He bullshits the worst.
It's the worst bullshit I've ever heard.
Well...
Wait, give me a second.
Give me a second.
Yeah.
Um...
Okay.
Well, you know, I've got to say, um, I'm starting not to...
Listen, it doesn't matter, but I don't...
My son is in the hospital right now.
He is?
Yeah.
He relapsed.
You know, I know that you have other issues, but he...
Is he okay?
He relapsed.
He overdosed.
He's going to be...
He's not dead or anything.
He's okay, but he is...
He's...
It was pretty bad.
Um...
I'm sorry, dude.
And since...
Yeah.
I know.
Since your...
Since your wife.
Yeah, I know.
Yeah.
He's got the same...
Because it's a disease.
Yeah.
I know, and it's just like, it's happening again.
And I just...
I can't lose them both.
And it's just...
I'm sorry I didn't text you.
I thought I did.
Well, here's what I'm going to do.
I can tell that you're not happy.
And the team isn't happy with you.
Um...
Yeah.
And what I'm going to do is offer you a very generous package.
Are you...
Are you firing me?
What I'm going to do is I want you to be happy.
So I'm going to offer you three months of your pay.
And then, um...
And then, uh, your box...
I packed up a box and your stuff is outside right now.
My son is in the hospital right now.
And you're telling me I'm going to lose my health insurance?
Well, listen...
Then I get through this show.
This is...
This is...
It's...
Business is...
Are you filming this right now?
No, I'm not filming this.
No, I wouldn't...
No, come on.
No, no, I'm just saying...
Um...
I gotta...
Like a prank thing?
No, no, I gotta go.
It just...
Um...
Good luck with everything in three months and, uh...
You put this out in a suit?
Okay, anyway.
Well.
Oh, man.
That's a horrible story if it's true.
If he made that up, he's a bad person, right?
I don't know.
I don't know.
You know, I feel like an asshole right now.
Well, I think, you know, there could be asshole factor six in you.
I don't know.
Was it not the right time?
Should I not have done it then?
Unfortunately, these two things are horrific.
They're both bad.
But, you know, there has to be some...
There has to be an outcome.
That's the whole point.
Because I don't think it's going to get better for him.
I mean, this is...
Listen, my heart goes out to him if that story's true.
Yeah, I didn't know that at all.
Well, do you know that?
Well, I know that there have been problems in the family, and he is dealing
with a lot.
Well, that's a very, very tough situation.
I mean, I don't wish that on anybody, but...
Should I say sorry?
Should I hire him back?
I feel like I should...
Why do you think it'll be better?
I'm like, he's in a lot of that.
No, but the whole point is, why is the original problem still...
It's still going to be there, whatever it was.
I mean, I don't know the details.
Yeah, yeah.
Listen, you know, business is...
You're right.
You know what you're talking about.
Yeah, you're right.
It's kind of like you have to take care of the remaining employees.
That's what matters.
Yeah.
You could be more generous if that story's really true.
Maybe six months.
Or maybe a year.
Or maybe a raise.
Maybe.
Well, okay.
Let's move on, because we have...