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How Mark Cuban went from beer-stained floors, flat broke to billions

Three weeks before his 24th birthday, Mark Cuban sputtered into Dallas in his ’77 Fiat X1/9, leaking oil and optimism.

All he had that July 7, 1982 day was a little cash, wrinkled clothes, a sleeping bag, a two-seat car with a hole in the floorboard and an invite to bunk with five guys in a three-bedroom apartment.

His ensuing rise to billionaire Mavericks owner is well-known dot-com lore, but what about the backstory? What brought him to Dallas? Who were these roommates and what became of them?

Meet Greg Schipper, Dave O’Brien, Mike Sterry, Dave Carr and Mark Wisely. Now in their early 50s and spread across the country, they have off-the-wall memories of the quirky roommate with the absurd reading glasses, the fellow they nicknamed Cubano and Slobbins.

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“Literally, Cuban landed on our doorstep flat-busted broke,” Schipper says. “Everybody figured, ‘We’ve got five guys, what the hell, what’s six? We’ll just split the rent one more way and make it really fun.’ ”

Today, they are divided as to whether they saw clues of greatness in the Pittsburgh-raised, Indiana University-educated party monger who crashed their place, and Dallas, on a whim.

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Was it fluke or fate that he arrived near the end of an oil boom, therefore in one of the cities least affected by America’s 1981-82 recession?

“Dallas then, like now, had a can-do spirit,” Cuban says. “So there were no limits to what you could do.

“No matter where, I was going to try to do what I could do, anyway. I think the bigger thing was I had nothing. So I had nothing to lose, right? It was all about going for it.”

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Having graduated in 1981 with a bachelor’s in business, Cuban operated a Bloomington, Ind., campus pub called Motley’s — until it was cited for having underage patrons, including a wet T-shirt contestant.

Meanwhile, IU classmate Schipper graduated in the spring of ’82 with no job offers. Sensing opportunity, he drove to Dallas and almost immediately phoned Cuban.

“Great attitude. Great atmosphere. Great energy. Great-looking women. Great weather. Get your butt down here.”

Welcome to Dallas

Cuban likes to joke that Schipper deserves credit, or blame, for altering the course of Dallas sports history.

Through Schipper, the dots connect to the four other roommates, all high school classmates from Rochester, Ind.

First to arrive was O’Brien, an IU fraternity brother of Schipper’s. O’Brien dropped out during his senior year and beelined to Dallas, where during the summer of ’81, he had lived with his brother and worked construction.

Next came Sterry and Carr. Sterry worked in an Oklahoma oilfield until his clothes were stolen. Upon returning to Rochester he saw Carr, who had dropped out of Indiana State.

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“My mom and dad were mad as hell at me,” Carr says. “Sterry and I went to Oklahoma, got there and found nothing we wanted. We knew O’Brien was in Dallas, so we said, ‘Hell, let’s go.’ ”

The three signed a $600-a-month lease at the Hill, a subdivision of the sprawling Village Apartments. To this day, the Village is a young-adult city within the city.

The early ’80s gave rise to Yuppies, and Dallas seemed to epitomize the young, upwardly mobile, materialistic professional. The Village was a melting pot of Yuppies and wannabes from around the country, rampant hormones and nightly keggers.

Many, including Cuban, carried student-loan debt. Cramming into apartments like sardines made fiscal if not actual sense.

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“Ours was a pretty nice apartment,” Schipper says. “But by the time we got done with it, it wasn’t.”

Schipper, tenant No. 4, shared a bedroom with frat-brother O’Brien. But Nos. 5 and 6, Wisely and Cuban, were relegated to the living room and sleeping bags on the brown shag carpet.

“It reeked of Miller Lite and Budweiser and everything else,” Wisely says.

“If you didn’t have a buzz when you went to bed, you had one when you woke up.”

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'The Hotel'

None of the six recalls the apartment number. They simply know it as “the Hotel.”

The Hill complex has since been demolished and rebuilt. The Hotel was an upstairs unit, overlooking a creek and the intersection of Greenville Avenue and Northwest Highway.

The closets were taken, so future-billionaire Cuban piled his clothes in a corner. Which garments might have been clean was anyone’s guess.

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“He pretty well lived in his corner,” Carr says. “He’d put on his clothes for work and they’d be wrinkled to hell. We’d say, ‘Slobbins, you’re not going to wear that, are you?’ ”

Thankfully, there were two bathrooms, although Cuban says the towel situation was “pretty nasty,” especially since the two he brought were frayed and scanty.

His first job in Dallas was bartending at elan on Greenville. Sterry was a gutter installer. Carr and Wisely worked construction.

O’Brien tried selling life insurance, then joined honors-graduate Schipper in phonebook ad sales. Schipper also peddled burglar bars before landing in magazine ad sales.

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Life wasn’t glamorous, but it was often bodacious, to borrow a catchword from that summer’s Fast Times at Ridgemont High.

The Hoosier state transplants satisfied their basketball yen with pickup games. None recalls attending Mavericks games when the team began its third season that fall.

They stretched their 18K salaries by scarfing happy hour food at elan, Confetti and Studebaker’s. Home staples included Hamburger Helper, instant soup and mac and cheese — and in Cuban’s case, cold spoonfuls of jarred Ragu or canned chicken and dumplings.

“We’d each buy a bag of potatoes that you could microwave and eat for a dollar a day,” Sterry says. “And each day we’d grab for the want ads, looking for a new job.”

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Got a job?

Of the Hotel dwellers, only Schipper and O’Brien previously knew Cuban, from the IU days.

Schipper informed the others that Cuban was a “riot” and perpetual wheeler-dealer.

Cuban had made extra cash at Indiana by starting chain letters. Somehow, he gained use of a campus cafeteria so he could give disco lessons. He took over Motley’s after persuading the previous owner to let him throw a party there and keep the proceeds.

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Wisely says Schipper and Cuban immediately widened the Hotel occupants’ social circle “100-fold. We were throwing parties every third weekend. The place was packed.”

Schipper says he and Cuban were on a two-pronged mission, reasoning “the more money we made, the more women we’d get.”

But what was the deal with Cuban’s reading glasses? Dark-framed with bottle-thick lenses, they required athletic tape to keep one of the temple arms attached. Usually, Cuban didn’t bother.

“The glasses were always half falling off,” Schipper says. “They were hilarious.”

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Cuban shrugs that he couldn’t afford new ones, adding, “Tape worked. Besides, nobody saw me wear them outside the Hotel.”

Cuban kept the glasses on the back lid of the commode, handy for Sunday mornings when he scoured the newspaper cover-to-cover.

“One morning after one of our parties, we hear him yell ‘Oh [expletive],” Wisely says. “Over the course of this party, someone had ‘knocked’ his glasses into the toilet.

“What’s he do? Pulls them out, rinses them off and starts reading.”

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Cuban showed he could play and work equally, though. He got a second job, as a salesman at Dallas’ first personal computer software store, Your Business Software. Never mind that he knew little about computers.

Hey, at least by then he had retrieved the faux-felt brown sectional couch and blurry rear-projection TV that had been in Motley’s. Instead of smelly carpet, now he slept on a mangy sofa.

“Nasty, crumbly filling poured out of this thing,” chuckles Schipper. “You probably wouldn’t let your dog sleep on it.”

A mind for business

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In December 1982, the Hotel occupants were stunned to find a lockout notice on the door, informing them their rent was overdue.

They had given their share to O’Brien and assumed he paid it. But he had disappeared and joined the Air Force. Gulp. The others would have to muster an extra $125 each.

“I don’t know if I’m going to be able to hack this,” Carr recalls Cuban muttering.

Wisely says the Village “had a way of drawing people in, but after a while it would weed people out. Probably, a lot of children were conceived there. A lot of friendships and business relationships probably were developed and ideas hatched.”

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Cuban and Schipper left the Hotel and moved into a neighboring Village subdivision, the Corners. The Hotel II lodgers included Cuban’s younger brother Jeff and another Indiana grad, Scott Susens.

Hotel II was intact for about eight months. Long enough for Cuban to earn enough to buy six of the biggest, fluffiest towels he could find.

Long enough for Cuban to get fired from Your Business Software — after defying the boss’s order to open the store, rather than close a software deal off-site.

That was a Thursday. The next afternoon, the Hotel II crew rode to Galveston in a red Ford convertible that Cuban bought from a friend, with a check that bounced.

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Susens and Schipper recall Cuban, between gawks at girls on the beach, scribbling notes on a yellow legal pad — the framework of the company he would start, MicroSolutions.

Cuban talked Susens out of an investment banking job offer and into joining MicroSolutions. But did Cuban throttle back on the nightlife? No. As MicroSolutions grew, so did the scope of the parties he promoted, until they outgrew the Village.

Cuban, Schipper, Susens and a Corners neighbor named Jeff Swaney rented a warehouse on Elm Street and threw a 50-keg bash with 2,000 guests paying $20 each. Swaney later transformed the warehouse into Club Clearview, paving Deep Ellum’s revitalization.

“After that party, we separated the money and there’s $5,000 or $6,000 apiece, and we were excited about that,” Susens says. “But I remember us thinking, ‘This is peanuts. We’re all going to make a lot of money someday.’”

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They did, especially Cuban. MicroSolutions sold for $6 million in 1990. His next venture, Broadcast.com, was acquired by Yahoo in 1999 for $5.9 billion in Yahoo stock.

Susens worked with Cuban until the stock buyout, then remained with Yahoo until 2009. Over the years, Cuban approached Schipper about being his “detail” guy, but Schipper was starting a digital-media sales company.

Now Schipper does contract work for National Geographic and is semiretired in Santa Barbara, Calif. A couple of summers ago, he accompanied “a bunch of other knuckleheads from Indiana” on Cuban’s G550 to Cancun for the Mavericks owner’s 50 birthday bash.

Does Schipper regret not taking one of Cuban’s job offers?

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“I’d lived with Mark and knew what he was like,” Schipper says with a laugh. “Even though I knew never to bet against him, it wasn’t the right career path for me.

“Would I have a G5 now? Maybe. Would I be any happier? I don’t think so. I couldn’t be any happier with my life.”

'This is crazy'

Odds probably were against it, but the four other Hotel I occupants, too, have experienced success.

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Sterry owns a gutter company and real estate in Dallas. A former Mavericks season-ticket holder, Sterry says Cuban would sometimes move Sterry’s kids to his courtside seats.

Wisely owns and operates mobile parks throughout Indiana. He has visited with Cuban several times when the Mavericks come in to play the Pacers.

“Someone once asked me about Cuban, and I joked, ‘He’s working on his second billion and I’m working on my second million,’” Wisely says. “But unless it’s someone close to me, it doesn’t come up that, ‘Mark Cuban and I slept on a beer-stained carpet.’”

Carr returned to Rochester in 1983 and is a luxury-home builder. He knew Cuban had done well but was surprised when Wisely phoned in ’99 to tell him about the Broadcast.com sale. He says he bought $2,000 in stock and sold four days later, netting $4,000.

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“I’ll tell you the craziest,” Carr says. “I woke up one night and turned to Fox and he was on a panel talking about economics. I’m sitting there thinking, ‘What the hell? This is the guy we called Slobbins. This is crazy.’

“One minute, we’re out there barely surviving. The next minute the guy’s on TV, talking with some of the world’s leading economists about how to turn things around.”

O’Brien was in the Air Force for four years. He lived in Rhode Island for 15 years and now lives near Clearwater, Fla., and owns two small packaging and distribution companies.

Now he can laugh about those Dallas days, and at himself.

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“I basically left under the cover of darkness, with a suitcase full of clothes,” he says. “Those were fun days, but as far as me being a responsible, contributing member of society, it wasn’t a good time, to be honest with you.”

When he left, his brother sold his truck and liquidated what he could. For years, O’Brien was certain his brother had settled the Hotel debt.

But a few years ago he contacted Cuban, who, after several e-mail exchanges, teased, “Don’t you owe me some money?” O’Brien phoned Schipper, who told him how hard it had been on everyone to come up with $125.

O’Brien compounded 5 percent interest and mailed Cuban a $500 check, adding that if he didn’t want the money he could contribute it to his Fallen Patriots Fund.

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What did Cuban do? He cashed it, probably with a smile, for old time’s sake.