Conversations with Coach Cowher
Mark Cuban
5/14/2026 | 27m 59sVideo has Closed Captions
Mark Cuban on hustle, risk, and getting his start in Pittsburgh.
Mark Cuban sits down with Coach Cowher to look back on the hustle that started in Pittsburgh—selling garbage bags, working odd jobs, and finding his edge early. He shares the lessons that shaped his path from Mt. Lebanon to building businesses, buying the Dallas Mavericks, and investing in others.
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Conversations with Coach Cowher is a local public television program presented by WQED
Conversations with Coach Cowher
Mark Cuban
5/14/2026 | 27m 59sVideo has Closed Captions
Mark Cuban sits down with Coach Cowher to look back on the hustle that started in Pittsburgh—selling garbage bags, working odd jobs, and finding his edge early. He shares the lessons that shaped his path from Mt. Lebanon to building businesses, buying the Dallas Mavericks, and investing in others.
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Thank you.
Okay.
You know, turn around.
Look at it a little bit.
Let those reflections allow you to reflect before you jump in.
I don't do this very often, but when I do, come over here and look at this, it's a remembrance of the journey that was taken to achieve this.
Not that you're measured by this.
It's a reminder of where you came from, the opportunities you were given, maybe kind of grit, determination that you applied.
This was the end of the road.
The map was a long journey.
It was filled with me reflecting on my roots, my upbringing, my appreciation.
And I got a chance today to talk to another man who grew up.
In the same area I did Mark Cuban, a champion of his own right, who's reached the pinnacle of entrepreneurship and actually won one of these 2011 NBA championship with the Dallas Mavericks.
It'll be kind of fun to talk about our roots, our journey.
Mark Cuban has to be an interesting talk.
So let's go back.
Let's go back Mt.
Lebanon High school.
Yeah.
And we we like I think you you would have tracked you.
You graduated.
You went all your early to Pitt.
Yeah.
What was you would have been your graduating class 76.
76.
Yeah.
So I was 75, right?
Yeah.
And you, you talked about and I remember reading about all the jobs that you had.
Right.
I, I delivered my first job was delivering the Pittsburgh Press and in crafting.
Yeah, for sure.
My brother, I used to help my brother.
He did the Post-Gazette, which meant you got to sweep in, right?
You got to sweep in.
Except Sundays.
Sunday.
Right.
Instead of, like, would you do the Pittsburgh Press because you had to get up so early?
No way.
Right.
And Sunday.
So I got Sundays.
We'd sit there, my brother and I, and we sit there who's got to wake up dad?
Because we can't carry him around.
So we were hoping dad had a good Saturday night.
Yeah.
So true.
Hey, so you're two.
You have two brothers, are they?
Where are they at?
Are they in Pittsburgh?
They're in Dallas.
They're Dallas now.
Yeah.
They've been.
They kind of followed me down.
And so after I started companies and everything, they started to work for me and do stuff like that.
So what are some of the jobs that you had in Pittsburgh?
Oh my goodness.
Like my first time I tried to make money.
I lived in Birdland in, Scott Township.
Chartiers Valley area would be my high school and, a Meadowlark Drive.
And there was a park down at the bottom of the hill, and I used to go and buy baseball cards, and then I would repackage them and I would sell them for more.
And with the promise that there would be a Pittsburgh Pirate baseball card, one of the packages.
Right.
So that's how I started to make money.
And then, one day my dad, when we lived in Birdland, he, you know, he, you know, his he and his boys would play poker every Thursday night.
And so one night, they were playing the Yank it up I'd go in there, grab a donut, they're drinking beer and talking, and, I was like, dad, I want a new pair of basketball shoes.
And he looks at me, looks at my feet.
He goes, those shoes look like they work.
When you have a job, you can buy whatever you want.
I'm like dad I'm 12.
One of his buddies who had to be drunk speaks up because I got a job for you.
I got all these boxes of, garbage bags that.
The boxes of 100.
You.
I'll sell them to you for three bucks.
You sell them for six bucks around the neighborhood.
I'm like, dad, can I?
And he was like, sure.
And literally no lie.
I had the world's first and only garbage bag route, right?
Like you had a paper route.
Oh, I would go door to door in Scott Township, and I'd be like, hi, my name is Mark.
Do you use garbage bags?
You know, and that's what got me started.
And from there, I mean, I sold magazines door to door.
I worked at Isalys on, Beverly Road.
Isalys.
That's chipped ham.
Let me just tell you about Chipped Chopped Ham Right.
What about it?
Yeah.
So?
So, anyways, I was working behind the counter, and I had to slice the Chipped Chopped Ham And one day I got distracted when I was, like, sliced off the edge of my finger and, like, didn't hit bone, but, like, at the end of my finger went flying and there was blood everywhere.
And so it's just like that was my short career at Isalys as I worked at Gracie's on Bower Hill Road.
I mean, every job you could, I laid carpet for a little bit.
Every job I worked out at Ralph's Discount in downtown Pittsburgh as a box, boy, you name it.
I had every stupid job there was for a kid.
And, you know, that is.
That's something.
So you go to Indiana because, And you go to the, the Kelley School of Business because it's one of the top ten.
But it was the least expensive because you knew you had to put yourself through it.
Right.
Exactly.
Was the cheapest one out of the top ten.
And I was like, okay, I could take a bus there.
And that's all that mattered.
And so one of the jobs you had and I go to this, ask you this question, and I read this about this disco dance lessons.
So, so yeah, that was you.
Hey.
So can I just tell you honestly, I was a closet disco guy, okay, I love to disco, but I was on call for football players to be in a disco.
So I would go in the back of a disco, sitting in the back of the bar in my seat, quietly just dancing to some badges.
I go and I'm like, this is like, I don't make sure no one sees me.
That I was like, loved it.
I would I would come home during the, summers in Pittsburgh and I would work at the bars down in Oakland.
So I worked at there was a bar called Chances R, you know, and I would work there every summer, just wherever I could get a job.
It was great, right?
But it was all discos and I would give dance lessons and I. You like I was getting paid back then $25 an hour to go to sorority houses sorority houses to teach girls and their parents how to dance.
Would take that job today.
And so one of the jobs that was a boilermaker, Freddy Galtier from the local, got me in there because I was playing college football at NC state, but he got me the full, I got the full race, so I was making like 13 bucks an hour.
I would work one night.
I do seven twelves for like one month.
I had like three grand and I go down to NC state.
Man, I was just like buying drinks for everybody.
Oh yeah, that was the dream job coach.
That literally was the dream job maker, right?
Freddy Galtier the local.
Right.
Because if you knew somebody that worked there was in the union, right?
Who could get you a job during the summer, even if it was just sweeping the floor?
It was nasty.
But they got paid.
They got paid.
I mean, they would stick us into these all these things.
They said, can you.
Well, I go like you're paid.
So you must be know how to weld.
I'm thinking well I don't know the guy I was with was the same way he goes, hey, man, you can do this.
I goes, I got you.
So I'm, I'm welding, learning how to weld.
Like literally they say we need to cut this out.
I'm going.
So I'm going like this.
I'm going, man, there's sparks going everywhere because you're doing great.
You're doing great.
I go, I don't think I'm doing that great I get down to boxers like I'm like, what was that?
But that's crazy.
Like, you were making $13 an hour.
I made $1.60 an hour.
Right.
So tell me about so your infatuation with the Mavericks, did you play basketball in high school?
Yeah.
Not well, I made it, you know, the first couple years, and then I got cut, right?
I, I, I'm like I was 6# 2## till I started to shrink and so but I didn't grow until I got to college.
Right.
I went from like that 5#11## to 6# 2## in college.
So I could play some.
But I wasn't very good in high school.
But in any event, it was just, I, I love the game, and that's what got me into it.
I mean, I would play pickup ball every day, right?
And then, after we sold Broadcast.com, Tiffany and I, when we were dating, went to a mavs game the start of the 99, 2000 season.
And I'm looking around.
It's the first game of the season.
We're undefeated.
We have Dirk Nowitzki, we have Michael Finley.
Steve, I'm looking around going, I could do better than this.
And so the guy who owned it was a guy named Ross Perot Junior, right, who didn't care anything about basketball.
He was just a real estate deal to him.
And he was good at that.
And so I was like, hey, I'll buy it from you.
And it was only a short negotiation, but we agreed to, to buy for $285.
And to me, that was a dream because I was a basketball junkie then I'm a basketball junkie now.
You know, I can barely move, but I'll still get out there, shoot and play with my son.
You know, being a Pittsburgh man, if Mark, you would come back here and buy the Steelers, I know that he'll be a lot more active in free agency than Mr.
Rooney.
I can't afford him any more, right?
You'll win a championship in 2011, and then all of a sudden you get involved with Shark Tank.
And I got to tell you, and this is the this is the truth.
My wife and I would sit here our default.
If we sit there, there's not a good game on okay or I don't want to sit there and watch a three hour movie.
If it's at 10:00 at night, what can we watch for a half hour or something?
I go, we have gone to Shark Tank for the last 3 or 4 years in this watching episode after episode.
I'm sorry.
No, no, no, I just, you know, like you, I take away is.
I love it, it's you coaching that's you coaching.
That's that is you coaching young people and like, you're you're asking the hard questions.
You're sitting there making them think what, what they really want to get into and do you really want to do this.
Yeah.
And make them defend their points.
And I, I mean, is that I mean that how you looked at the Shark Tank?
You know what?
You're the first person to say it that way.
I didn't really look at it as coaching.
But you're right.
Like the way I looked at it, this, you know, the people to get to that carpet on Shark Tank and pitch us, you have to be kicked out of thousands of people that audition.
And this is your whole life on the line.
And my attitude was, I'm going to try to help you, right?
Because this is so important to you that even if it's not a business I wanted to invest in, I always want to leave you with a piece of advice, some coaching to help you do better.
And I would hear back, even though, you know, I might not have done a deal, I would hear back from people all the time.
Hey, you gave me great advice.
This helped me, you know, take my company here or there.
But you nailed it, coach.
You know, it really is about coaching.
Just like athletes, entrepreneurs need coaching too.
No question.
You provoke thought.
And I said, you can sit there if you you have a talk if somebody walks away.
And I provoked thought and made them start to think about something, isn't that a degree of wisdom, a mentorship that you are giving them right now in the course of doing that, to make them look within themselves?
The give some thought about thinking outside the box, because I look at your success in sports, I look at your success, success in entrepreneurship.
I just go back to Pittsburgh and I think about people from Pittsburgh.
It's called grit and determination.
And if you represent that man and I think you you share that with the people, you're around you.
It's about hard work.
It's about finding your passion.
Right?
You sit there and it's like, okay, there could be a competitive spirit.
I says, you know, don't be surprised by winning and let losing inspire you.
And so I so I said, don't be surprised by winning.
But let losing inspire you.
Yeah.
You know, you know better than anybody that losing hurts more than winning feels good.
It does it does.
You know.
And in business it's the same way.
Right.
When you when you lose the deal, when something happens to your company, it's the worst thing ever.
And when you win, when you win a deal, when you're growing your company, then that was last year and you got to do it again and do a better right.
And I think that I use that exact same statement when I said about, you know, what would you say when you've had a sustained long period of time?
I said, I think what happens is when you first start, the winning feels great and the losing inspires you.
I said, but as long as you stay in it, the higher level of expectation that you create the losing starts to feel worse than the winning feels good because winning becomes an expectation, yo.
Oh yeah, I mean, and you know, you, you've been part of championship teams like when we won in 2011.
I remember running on the court just just beaming and smiling and then realizing, oh, that season is over, right.
24 hour rule.
But after a championship you strictly 72 hours, maybe a week.
I still celebrated it.
Yeah.
I didn't say I wasn't stupid, but in my mind, right.
I'm thinking, how do I top this?
Where do we go next?
Right.
And then unfortunately, the NBA had a lockout and that kind of screwed us all up.
But, it was just like, if you if you're a competitor.
Yeah, you're a competitor.
Yeah.
Sports is competition.
But business is the ultimate sport because you don't even know who you're competing against.
And you don't know when the game ends or the game starts.
You can't make trades.
It's just different.
And the thing I loved about you too and I just I just sit there I said, Nick, you think outside the box.
And I used to sit there and just tell my coaches, I said, if we want to be at the very best, we got to stay a step ahead.
I want some creative, innovative thinking, think outside the box.
And we took that to the next level of blitzing.
We took the next level of an offense just looking for the type of athlete, but to stay up there and I go back to the same thing.
That's a Pittsburgh trait that we had because always yes, I mean, it's a competitive spirit that says, you know what, I will play within the rules to a degree.
But I said, and if I if I play outside the rules, it's not it's not cheating unless you get caught the rules just aren't good.
Right.
Well, the refs just don't know what they're doing.
Right.
So you get back to Pittsburgh much.
Ar there any thoughts coming back here?
Yeah I mean I wouldn't live there because my family's here now and I go back my my high school buddies are still my best friends.
And we still use like our all of our nicknames.
Like I took Russian in high school and my name in Russian class was Boris.
You know how you have to pick a name?
yeah, I was Boris.
And so they all still call me Boris.
There's Bomfy.
There's Big man, there's Tow the pro, there's more.
You know, there's Stewie, I mean, all these stupid nicknames.
And I go back all the time just to see those guys.
We'll go to a Steeler game, a Pirates game, Penguins game.
Whatever.
Hey, so I got to go.
I gotta tell you this other story because I. The immaculate reception because we were both there around the same time.
So yeah, I can tell you from where I was on the Immaculate reception, number one, I didn't, I didn't my dad was sitting in the kitchen.
He'd have his beer with my mom.
Listen to Maroko.
And I just said, I'm going to, we're going to go out.
I'm gonna go play football outside.
So I went outside for the game.
I can't see the game because the game wasn't on TV.
No, it wasn't on.
So I went, I, we were just playing out there and I remember my dad.
Can I go?
You are not going to believe what happened I don't know what.
And so he goes, you'll see it on the 6:00 news.
Right.
I remember exactly where I was.
I remember exactly where I was, where I did the same thing we were, I was at my house and I had a, a hoop in the backyard on the driveway.
Like this game's over.
Yeah, right.
And I'm just going to go off and get some shots up, and I hear my dad.
Oh my God, oh my God, oh my God.
Right in the basement, you know, and jumping around.
And then you saw on the 6:00 news.
Yeah.
Did you go to many games.
Oh no.
We went to one game like my, my dad did upholstery on cars.
It was a big deal.
But I remember the last game I went to with my first game and last game I went with my dad, was at Pitt Stadium.
I went to Pitch Stadium with Cannonball Butler.
Yes, yes, it was.
You had a heart attack hill.
You had to walk up the heart attack hill walking up there with my dad and my uncle.
It was the I'm like, where are we going right now?
And it was, it was, you know, it used to be S.O.S.. Same old Steelers right before you got there.
Right.
And so I'll never forget, I went up there and I think it was the Redskins we were playing.
And the first play of the game they throw like an 80 yard bomb to Roy Jefferson.
If I remember that.
Oh yeah.
Yeah.
And we're up seven nothing.
And then we lose.
Of course it was like 14 The guy I remember the most name was Bobby Walden because he was the punter.
Yes, Bobby.
Yes, he was a punter because he punt more than anybody in time he was I knew he wanted the quarterback.
Oh my God.
Just like arguing about Joe Gilliam versus Terry Hanratty versus Terry Bradshaw I know.
So so let me ask you this question.
So just you the success you've had.
And then I think it's just this has really been fun talking to you and I, I want to get your address too.
I want to send you my helmet.
I'm going to sign I want to get you.
Please.
Yeah, I do, I do, I want to and I want to send you my book too.
I want to say because you'll you'll appreciate it.
It's all I appreciate.
It's like I had a lot of mistakes, but I always call them lessons learned.
And it was a lessons learned.
All right.
So.
So, as you sit here, what advice would you give to young entrepreneurs today?
Like if you had to sit there and someone said they want to be the next Mark Cuban?
First, you don't want to be me.
You want to be you, right?
But so I have the same rules I try to teach my kids.
I try to live myself like.
Number one is, how you do anything is how you do everything.
You know.
If you cut corners anywhere in business or in life, right, it's going to catch up to you.
You don't want that to become a habit, right?
And then for entrepreneurs specifically, I tell them, and this is from Bobby Knight, I stole it for him.
Everybody's got the will to win.
But it's only those with the will to prepare that do win.
Right.
And then specific to business sales cures all.
Because if you don't believe and love your business so much that you know that when you're selling your product or service, you're helping somebody and it's the most important thing, you're not going to succeed.
No business has ever succeeded with no sales.
Yeah.
So those are like kind of my three lines, but the one that I always make sure runs through my head, even is how you do anything is how you do everything.
Yeah.
What point do you sit there and say, is it worth it?
Yeah.
You know, how many times have you sat there and said, you know, man, like, why am I like, why am I doing this?
And at the same time you're doing it because you need a job.
It's a job.
It's your job.
And you know what?
Sometimes those jobs didn't didn't pan out.
Yeah.
That wasn't the worst thing in the world, right?
I mean, no, I mean, like, I learned more from the jobs that I hated.
Yeah.
Jobs I know.
Right?
As an entrepreneur, I learned what not to do.
Right.
And like I got fired from jobs and I like, I realized I wasn't a very good employee.
I didn't get fired because I didn't know what I was doing.
I got fired because I was like, always trying to do too much, or I thought I was too smart, right?
Instead of just listening to the right owner, whoever and doing what they say, I was like, oh, you don't even went up.
But, yeah, your point.
Like, I wasn't a good employee, but I made sure, like, I would tell people, I tell kids to this very day.
I'm like, you pay to go to college, but you don't need a perfect job after you graduate because you're getting paid to learn, right?
And that's the way I always looked at it wasn't a great job, but I was getting paid to learn, and I learned a lot.
And when I finally got fired from a job and started my first real company, Micro Solutions, I knew I thought I didn't know everything.
There was a lot I needed to learn, but I learned some things about what not to do from the bosses that fired me.
And that's why I live by this mantra that there's no mistakes.
They're just lessons learned.
Yes, you know what?
They know what.
And you can always live a safe life.
But it's okay to go out and risk and do something.
Oh, yes.
Yeah.
And how about this.
And I and I believe this I said, you know like talking about what do you say before a big game with Super Bowl game.
I said this tell you something.
We're all going to we all live with regrets.
Regrets for things we do have regrets for things we didn't do.
And I would much rather have regrets for things I did.
I don't want to sit there, and I don't want to sit there and just say, well, I wish I would have done this.
Now go for it, man.
Go for it.
And you know what?
If you don't make it, it's a lesson learned.
But you know what?
You went for it always like my line.
The same kind of line is it doesn't matter how many times you fail.
You only gotta be right one time.
And then everybody will tell you how lucky you are, right?
You know, that#s it.
Before you got on here.
So I picked up my Super Bowl trophy and I talked about.
That's not the reason why I've lived my life.
I've always tried to achieve this is kind of the result of that.
But I think when you live with a sense of purpose, the hard work, you never forget where you came from.
It's a little bit of reflection as you look at anything that you accomplish.
A reflection of the core values that you stand for.
Is that not what Pittsburghers are all about?
Amen.
You know what What makes us different in some respects is every kid I know, even if they're not kids anymore, every kid I knew growing up, all of our dads went to work.
All of our dads, you know, would leave too early in the morning, would leave, would get home too late at night, were exhausted, couldn't do everything.
Like my dad wasn't at every football or basketball game because he had to work.
You know, when you see your parents work that hard and not necessarily accomplish their dreams.
And remember, our parents were the first generation coming from immigrants who had nothing, right.
Our parents were the kids of the depression, and their parents came over here with nothing.
And, you know, are all of my friends, you know, your friends, our grandparents, right?
Might not even have spoken English.
Right.
And they left the country to get here.
And I think that resonates with all of us.
You know, it's funny because I. Your mom, did your mom work?
Yo, my mom did every stupid, odd job you can imagine.
My mom, my mom used to take the pack bus downtown to work at a restaurant.
She never knew how to drive a car.
She, my dad.
My dad tried one time to teach her how to drive a car.
We were living down in Beach View in the city, and we're coming up this hill and my dad says.
Hey, when you turn the car, don't worry about the wheel.
Turn back by itself.
So she's driving, she turns it and she goes.
She just takes her hands off the wheel.
He goes no no no.
She hit the wall.
That's the last time she was ever behind the wheel.
Hey, let me just tell you, I used to take the 41 B and then take the 41 C to get downtown, right, to work at Ralph's discount or.
I worked at this Greek restaurant always.
So we would go to Pirates games, and I'd always, you know, we would buy the cheapest tickets and then try to sneak down as much as we watch the game.
But there was there was a guy who worked at one of the gates, and I promised him a hoagie one time, and I brought I learned to bring this guy hoagies, and he would let us into the box seats and we were just sit down.
So did you ever did you ever have you went to Forbes Field, right?
Yeah.
Yeah.
My dad would take me out.
Did you ever have the.
So I used to go there and I'd sit there.
Sometimes we would go there a bunch of, like, my friends and we, we were tempted to be one of those guys that ran across from right field and try to climb up, do you remember that people used to do that.
And then they would take off.
The police would come out and it's like, go, go, go.
And the guy was climbing arguably like nine out of ten times.
They got caught.
But then every now and then the guy would make you gotta wait anyway with you.
I'll tell you about Forbes Field story.
Right?
So after they tore it down, that's, I went.
I told you, I went back home to Pittsburgh and I lived in Oakland.
Right.
And then I would work at the time, but I lived on Dawson Street, which is right next to where the the wall was that they left up.
And so that was my place.
When I would like to have a date or anything, I'd bring her up there and try to make out at the Forbes Field wall.
That that was your getaway anyway.
Right?
Field of force field.
Oh my God.
I'll just leave you the this Mark, you know, you did not disappoint.
I mean, you are you.
I've looked up to you for so long just because of just the way.
The way that you just have attacked everything with a passion, with a grit, with the determination and doing things the right way.
And and just again, your ability to mentor while you're doing something because you're, you're, you're teaching a lot of people what they really need in life.
And it's not always going to be easy.
You're not going to be defined by how many times you get knocked down before by how many times you get back up.
I think that goes back to Pittsburgh blood.
I love to see you sometime.
I hope our paths run across.
You're the best man.
Thank you for doing this.
Thank you.
Coach.
It was great.
I really enjoyed it.
That was fun.
Yeah.
You know, you think about special people from Pittsburgh and the successful people from Pittsburgh and guys like Mark Cuban involved in sports, involved in entrepreneurship.
But he never forgot where he came from.
And I think you walk away and I talk with him.
And as we share stories, we realize the parallels that we both had while championships were maybe the end of the or are result of those parallels.
It was a journey we both take and and still take today.
The core values that you had, the grit, the determination, the passion, the willingness to think outside the box, all the things you learn from to be successful in Pittsburgh and to be able to survive in Pittsburgh still exists today and can take you to a very, very tops of mountains.
That's Mark Cuban.
We got to talk about your sweatshirt.
Okay.
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