During a recent filming day on the Shark Tank set in Culver City, California, the competition for deals was intense. But as the crew prepared for the next pitch, the Sharks unwound with some fun. The Sugarhill Gang's "Rapper's Delight" blasted, prompting Daymond John, Lori Greiner, guest Shark Bethenny Frankel, and Robert Herjavec to dance around the stage. Mark Cuban nailed the lip-sync: "I said a hip hop the hippie the hippie / For the hip hop and you don't stop / Rock it for the bang bang boogie / Say up jumping the boogie for the beat." Even Kevin O'Leary tapped his feet while texting. Daymond capped it with a pirate joke: "What do you call a pirate with two arms, two legs, and two eyes? A rookie," drawing groans from the group.
"We're very zen in the den," Herjavec laughs. "If I lose a deal to another Shark and it succeeds, it was meant to be. Success combines the right time, opportunity, Shark, and go-to-market strategy."
Still, the Sharks openly share regrets over deals they made or missed.
Deals the Sharks Regret Making
In season five, all five Sharks united for a rare $1 million deal for 30% of Breathometer, a smartphone-connected portable breathalyzer. Users blew into it for an app-based blood alcohol assessment to gauge driving safety.
Challenges followed: fulfillment issues and inaccurate readings that understated danger levels. The FTC mandated disabling the app and full refunds.
"They faced major hurdles," Herjavec says. "This taught me to invest only in entrepreneurs with proven business experience."
The Deals That Got Away
Lori Greiner's instincts have fueled Shark Tank triumphs like the Simply Fit board ($170 million in sales despite Daymond's "plastic potato chips" jab) and Scrub Daddy ($150 million, post Kevin's dismissal).
"I don't look back," Greiner says. "I landed the deals I wanted." Yet she regrets passing on Doorbot in 2013—a Wi-Fi doorbell streaming video to phones or computers. Sharks called it unremarkable, overriding her "hero product" gut feeling. Rebranded as Ring, it's now valued at $1 billion per a November Shark Tank update, a top success story.
"I should have trusted my instincts, invested, then done due diligence," Greiner reflects.
The Sharks stay resilient. "Why cry over spilled milk," O'Leary says, "when another killer pitch is always coming through the door?"
Related: What Sharks Have Learned After a Decade in the Tank
