Two women in little black dresses enter the tank. One has dark hair, the other has long, blond locks. “Okay, folks, 30 seconds,” the stage manager says. “Here we go, folks, stand by. Shark Tank 65 is in session. And five, four, three. Gentlemen, lady.” His pointed index finger signals action. Doors open, and the women begin the long walk down a corridor, toward the five Sharks in their leather chairs. The dramatic music and the voice of the announcer you hear on the show are absent. The only sounds are the uncertain clicks of the ladies’ stylish stilettos.

The women reach a red and blue Oriental rug laid out before the Sharks. But they can’t begin their pitch until a camera has filmed them from all angles, taking a full minute. They stare silently at the Sharks. It is excruciating to watch. 

Finally, the director gives a cue, and they begin. “Hi, I’m Rachael.” “And I’m Melissa.” Then together: “And we are the Cashmere Hair girls of Beverly Hills.” They deliver a well-rehearsed, two-minute pitch to get the basics of their clip-in hair-extension business across to the Sharks, who are clearly hearing this information for the first time.

The energy on the set is low. It feels like any other business meeting that you’d rather not suffer through. Cuban listens and takes notes. Why would he even consider getting involved in a deal like this? Then again, he invested $25,000 for a 33 percent stake in a business called I Want to Draw a Cat for You.

John and Greiner ask the tough questions, and, after about 30 minutes, both women lose confidence. The dark-haired one gets defensive. Her high-pitched voice cracks. In midsentence, she loses her train of thought, stops talking, and stares at the floor. John tells her to take a deep breath and relax. The cameras capture a close-up of tears in her eyes.

“So, what you are telling me is that there are no women out there with real hair,” O’Leary says. “I hate this product.” 

The dark-haired woman, now looking like she might faint, offers a meager retort. “We will work for you 20 hours a day,” she says. 

Cuban cuts in and gives them advice instead of a deal. “How are you going to compete?” he asks. “How are you developing your brand? Have you defined where you are going? Forget the market, get people to trust you. Just know what you are doing. If you hustle, it will happen. You’ll be fine.”

The show has aired, so I can tell you that these women did not get what they came for. However, they did get priceless national television exposure for their product and expert advice from the Sharks. I have little doubt that the Cashmere Hair girls of Beverly Hills sold some hair extensions after the show aired. I myself rushed back to my hotel after the taping and almost dropped $400 on a set of Sunset Blonde 20-inch extensions.

Shark-Tank2 IN THE TANK: Mark Cuban's aggresive personality has made him the show's breakout star.

After the women leave, stagehands descend on the set, roll up the carpet, and prepare for the next entrepreneur. Makeup artists circle the Sharks and touch up their faces. I am surprised to hear the Sharks still talking about the hair-extension deal. There are no cameras, yet they continue to discuss what would have made the deal work and what the women could do to make their business more successful. Nobody is listening but me. Finally, Cuban stands up and stretches. Greiner kicks off her high heels. “Dead Flowers,” by The Rolling Stones, blares from the sound system. 

“This show is a lot of work, but it’s really a lot of work once you close the deal,” Cuban says.

The stagehands set up two Christmas trees and a table draped in a blue cloth atop which sit boxes of Hanukkah Tree Toppers. The group of people sitting around me snickers as a nerdy man wearing a blue Santa Claus hat hits the carpet and says, “Hello, gefilte Sharks.” For the next 40 minutes, he explains how he is going to “bridge the gap between ho ho ho and dreidel, dreidel, dreidel” by selling Star of David tree toppers to interfaith families. Woody Allen could not have scripted a hokier infomercial.

Greiner, the “Queen of QVC,” does not bite. She doesn’t think the market for the product is broad enough. O’Leary scolds the man for bringing to the Tank a hobby he sells out of his home. The man’s chutzpah is impressive, though.

“My vision is seeing this on the top of a 100-foot tree in New York,” he says. 

O’Leary replies, “My vision is making money. Your vision does not have dollar signs. I’m out.”


Cuban uses the moment to offer advice he often gives on the show. “You’re a mensch,” he says. “The biggest challenge I’ve experienced on my time on Shark Tank is growing someone out of working in their home or garage and into a business. You have a full-time job, and you want to make everyone happy. But as an investor coming in, I want a return. You can’t be everything to everybody. You aren’t set up for it. I’m out.” 

Just when it looks like curtains for the meshuggener, John throws out an offer. The Sharks laugh at the stunt, but John is not kidding. The guy walks out with $50,000 for a 35 percent stake in Hanukkah Tree Toppers. There were no scripts or prompts. Months later, when I watched this segment on television, it was edited only for time. The way the deal went down wasn’t changed.

The cameras are off, and, once again, the Sharks hash over the details of the presentation. Several of them question John’s judgment. I wish they would show the post-pitch interactions. It occurs to me that these serial entrepreneurs really are Sharks. They don’t care about the size of the prey, they’re just hungry. They are wired to do deals. I look at my watch and realize I’ve been watching the taping for four hours. It feels like far less. The stress of watching the Sharks work has made my stomach ache and my throat feel tight. It’s time for lunch.

• • •

I leave sound stage 25 and weave through the studio streets, past the set of Jeopardy! and Wheel of Fortune, to the catering area. The cast and crew sit on long tables covered with green plastic tablecloths. I grab a spot next to Cuban, who is devouring a plate of salmon and a tossed salad. From our table, we can see the basketball courts used by movie and television stars who need to blow off steam between takes. I’ve been told Adam Sandler rules the courts. “We’ll see about that,” Cuban says.

I tell Cuban I am physically exhausted from watching the taping of Shark Tank. “It’s crazy, isn’t it?” he says. “We are concentrating so hard. You just have to pick up the nuances of everything.” 

A woman sitting across from me says she does not trust reality television because it feels contrived and made up. “You can’t make this shit up,” Cuban says. “This show is a lot of work, but it’s really a lot of work once you close a deal.” The Sharks sometimes field nine pitches a day, wearing the same clothes from one day to the next because the segments are mixed and matched. The pitches range from 20 minutes to an hour and a half.

Cuban says he has hired 10 people to oversee his Shark Tank businesses. He may shake hands with an entrepreneur on the show, but sometimes the deal falls through during due diligence. “Of the deals I make on the air, maybe 30 percent don’t happen,” Cuban says. “I’d say 90 percent of the time, the entrepreneur changed the deal. It was not us backing out.” 

villy-custom-bikes Villy Custom bike

I ask Cuban why he bothers to do the show. In 2012, All-Star Brooklyn Nets point guard Deron Williams said he decided to stay with his team in part because Cuban was too busy taping Shark Tank to come woo him personally. Whether that was true or not, Cuban couldn’t have relished the negative publicity. In addition to the Mavericks, he has investments in high-tech companies and entertainment to worry about. Cuban produced the movie Good Night, and Good Luck, which was nominated for six Oscars.  

“The show has become a reinforcement of the American Dream,” he says. “When you see people come out here and see them be successful, you think, ‘I can be, too.’ And you get advice and get the feedback, and, in aggregate, it’s an education. That’s important in this day and age, in this economy. I do it, too, because it’s philanthropy to me. I want to help companies grow and help people have their dreams come true.”

You might be tempted to dismiss that explanation as insincere. Remember, this is the same guy who showed off the hip-replacement scar on his bare behind for Dancing With the Stars. He loves attention, and there is no doubt that the attention he gets on Shark Tank feeds his business. But while he might romanticize his Shark role, Cuban does take philanthropy seriously, matching every fine he gets from the NBA (and there have been many) with an equal amount donated to charity. And he’s right about the show. If you watch it long enough, you get a business education between the snarky sound bites.

I tell Cuban that my 4-year-old nephew was watching a Mavericks game, and, when he saw Cuban on the screen, he said, “Hey, there’s the guy on Shark Tank.” Cuban laughs but says he isn’t surprised.

“I went to speak about the Mavs at Hockaday, where my girls go, and as soon as I started talking, the kids starting asking me about Shark Tank,” he says. “I have a 4-, 7-, and a 10-year-old. The older two are always talking about deals and asking me why I did this or that. I have to negotiate with Alyssa, my 7-year-old. She kicks my ass. We call it The Alyssa Tank.”

O’Leary approaches our lunch table. Without looking up from his phone, he says, “We were just talking about rehearsing for the Emmys.” 

Cuban has apparently overlooked this entry on his calendar. “What are you talking about?” he asks. 

“The Emmys,” O’Leary says. “We have to sit there for four hours tomorrow night.” 

“I’ve been nominated for the Academy Awards,” Cuban says. “It’s brutal. I hate it.” 

The talk turns to basketball. I let Cuban know that in another life I was the general manager of the Dallas Diamonds, a women’s professional basketball team, for two years. In 1981, I drafted arguably the best female player in the game’s history, Nancy Lieberman. I have his attention now. He fires questions at me. “Yes, we made money in the second year,” I say. “You really had to hustle,” he says.

I ask why he moved from Pittsburgh to Dallas. “Fun, sun, money, and women,” Cuban says. “I lived in The Village with six guys in one apartment. I slept on the floor and worked as a bartender at Elan.” 

We talk about life in Dallas during the early ’80s, all details off the record. We realize we have friends in common. Which is when I start to think that I’m getting tight with Cubes. When we get back to Dallas, no question we’ll hang out. Maybe he’ll want my input on the empty GM chair in the Mavs’ front office. 

Several months later, I email my buddy Mark some follow-up questions for this story. The email is not answered in five minutes. I hang for five days before I resend. No reply.

Early on a Sunday morning, I craft a 30-second elevator pitch for help. Bam. He answers. I scan his email. Did you ever take the court from Adam Sandler? “No. We are working. Didn’t have enough time.” Was the pitch from the bicycle-light guy the most heated Shark Tank exchange he’d ever had? “I don’t remember. You waited too long to follow up. We do more than 100 deals when we tape.”

I feel my chance of becoming the general manager of the Dallas Mavericks slip away. And then my fate is sealed. I ask: “When taping the show, do you stay in L.A. or go back and forth daily on your jet?” He replies: “Dumbest question I’ve ever been asked.”

Was it a dumb question because he does or because he doesn’t? I will never know. I didn’t handle my deal right, and I missed my chance. This is the reality of dealing with Mark Cuban. You never know if you’re going to get a million dollars or an insult. I gave it my best shot. I’m out.