One of the most underrated TV shows on ABC is Shark Tank. Kevin O’Leary, aka Mr. Wonderful, has been on Shark Tank from the very first episode – in fact, he never missed any. With a fortune worth 450 million dollars, O’Leary has made a name of himself in the software industry and has made many successful deals on Shark Tank. Among O’Leary’s most famous deals are BasePaws, the pet-DNA-testing company; Greenbox, a pizza box that also serves as a plate; and Verbalizet, an app that translates languages in real-time.
However, once a business dives in the Tank, people can always expect O’Leary harsh demeanor. He is very transparent about his opinion of business practices, markets, and the current economy, which leads to him saying savage comebacks to entrepreneurs. O’Leary also does not oppose stealing the deal from the other sharks, which provided memorable moments on TV. Walking away with a deal or not, one can always count on O’Leary’s honest opinion – here are the top 10 takedowns on Shark Tank.
Shark Tank
- Release Date
- August 9, 2009
- Cast
- Mark Cuban
- Seasons
- 11
10 ‘You just made me p***, I am out!
Season 14, Episode 16
In this episode, we meet Michael Akindele and Ehime Eigbem, a husband-and-wife team who introduce the Sharks to Sweetkiwi, a guilt-free frozen yogurt. The Sharks were eager to try the healthy treat, as they are always when food is involved. Ehime created Sweetkiwi to offer a healthier dessert option, and the couple has successfully expanded the brand by opening stores in Nigeria. Entering the Tank, they sought $250,000 for 5% of their company.
O’Leary offered the requested amount but for 20% equity, and while the couple wanted to explore other offers, Mr. Wonderful remained open to negotiations. As the couple pitched their marketing strategy and tried to win over the Sharks, it became apparent they were particularly focused on Mark Cuban. Frustrated by their hesitation, O’Leary eventually declared, “I’m out!” since he was the only one who had made an offer. In the end, Robert stepped in with an offer, and the couple walked away with a deal.
9 ‘Stop the madness, are you out of your mind?! Are you crazy? Who would give you ten bucks for that??’
Season 1, Episode 1
In one of the most popular pitches in Shark Tank (for the worst reasons), Mary Ellen Simonsen presented her idea for organizing sticky notes on Season 1 of Shark Tank, seeking a $100,000 investment for 20% equity. Her product, an attachment for laptops or desktops to keep sticky notes clean and organized, had no sales and no patent.
Kevin O’Leary immediately questioned the $500,000 valuation, asking how a sticky note holder could be worth that much. Mary struggled to justify the product’s value, leading O’Leary to lose his temper, yelling that she was out of her mind. When Barbara expressed interest, O’Leary even claimed she must not be from this planet.
8 ‘You’re dead to me’
Season 1, Episode 4
Paul Watts pitched his Graffiti Removal Services, a mobile franchise, on Shark Tank, seeking $350,000 for 15% equity to expand his business through franchising. His vision included a truck equipped with environmentally-friendly products, sourced from a single manufacturer. Robert countered with an offer of $350,000 but demanded 75% of the business, effectively making Watts an employee in his own company. O’Leary then proposed partnering with Robert on the deal.
In a dramatic turn, Paul declined the offer, refusing to become an employee of his own business. O’Leary, visibly upset, warned, “If you walk away, I’ll forget about you.” Watts confidently replied, “No, you won’t. Every time you see graffiti, you’ll think, I should’ve invested in that company.” He walked off the stage without a deal, keeping his head high and believing that he made the right choice.
7 ‘The market has spoken…and its basically telling you – people hate this product. I hate it too’
Season 5, Episode 19
In a very embarrassing pitch, husband and wife Ivan Barnes and Lisa Evans pitched Squeeky Knees, toddler clothing with built-in squeakers, on Shark Tank. Despite only generating $10,000 in sales over three years, they sought $80,000 for 20% equity. Squeeky Knees featured a patented “squeaker” sewn into the knee area of toddler pants, which Lisa created in 2010 to protect her son’s knees and bum while adding a playful element as he explored the house. The couple invested all their savings into the business, hoping the Sharks would see its potential.
When Lori Greiner inquired about their sales, Ivan revealed they had sold 500 units, making just over $10,000 in three years. The Sharks expressed concern, noting that the constant squeaking could be annoying as toddlers move around. O’Leary was particularly critical, dismissing the product as a bad idea due to low sales and bluntly telling the couple they were “right over a cliff.” The couple left the Tank without securing a deal.
6 ‘There is only one answer to this. I have to hire you both, so I can fire you’
Season 6, Episode 1
In this episode, we are introduced to Amber, a mobile phone charging station with fingerprint scanning, pitched by entrepreneur Bill Shuey. Shuey aimed to sell Amber to venues like restaurants, museums, airports, and movie theaters for $180-$200 per unit. While the Sharks recognized the potential of the idea, they saw it as a poor business proposition, especially since the product was only available for pre-order.
O’Leary wasted no time in shutting down the pitch, calling it one of the worst ideas he had ever heard. He disliked the product so much that he jokingly said he wanted to hire the Amber team just so he could fire them.
5 ‘You can’t even LIVE in New York for 45,000. There are rats that are making more money than that’
Season 10, Episode 7
In this episode, Samantha Stephens introduced OatMeals, a creative oatmeal restaurant concept featuring innovative recipes like oatmeal with bacon, truffle, banana, and even cheese. The Sharks were impressed, with Lori Greiner calling it one of the most delicious meals she had ever tasted on Shark Tank. Samantha, who had been running her New York City business for six years, was seeking $500,000 for 20% of her company.
However, when Samantha revealed she only paid herself $40,000 annually, Barbara questioned how she could survive in such an expensive city. Mr. Wonderful bluntly stated that no one could live in New York on that salary. Despite these concerns, Samantha ultimately secured a deal with Lori, aiming to bring oatmeal back to American breakfast tables.
4 ‘They’re going to crush you like the cockroaches you are!’
Season 3, Episode 15
This phrase is one of Mr. Wonderful’s most famous lines, often repeated across multiple episodes. One instance was during Ryan Custer’s pitch for Cougar Energy, where he sought $150,000 for 30% of his company, which aimed to sell energy-drink shots to single, middle-aged women interested in dating younger men like himself. With only $60,000 in sales over three years, the pitch was a clear example of how weird this business idea was.
Kevin O’Leary often delivers reality checks to contestants who haven’t fully considered their competition. Many entrepreneurs enter the Tank with ideas that can be easily replicated by larger corporations or are already being executed more effectively by others. The beverage industry, in particular, is notoriously challenging, and when Kevin sees that the entrepreneurs haven’t thoroughly thought through their competitive strategy, he doesn’t hold back: he tells them they’re going to get crushed.
3 ‘We’re spanking him like a baby seal!’
Season 2, Episode 1
Jonathan walked into Shark Tank during Season 2, seeking $85,000 for 10% equity in his men’s fashion accessory brand, Wurkin Stiffs. He demonstrated how his innovative magnet system effortlessly keeps shirt collars in place. Jonathan shared that he came up with the idea while trying to control his own floppy shirt collar, using paperclips and magnets to create the first Collar Stay prototype.
Jonathan was eager to partner with Daymond but grew impatient, feeling that Daymond was taking too long to make an offer. Daymond expressed his frustration, stating he couldn’t work with partners who wouldn’t communicate properly. Mr. Wonderful cut through the tension, demanding a decision. Ultimately, Jonathan accepted a deal with Barbara and Daymond for $100,000 in exchange for 40% equity. Since appearing on Shark Tank, Wurkin Stiffs has expanded its product line to include a variety of men’s business attire accessories, ensuring you stay sharp throughout the day.
2 ‘Ok, that’s wonderful. But how do I make money off depressed people?’
Season 6, Episode 7
TITIN founder Patrick Whaley entered the Tank seeking a $500,000 investment in exchange for 5% equity in his company, which sold compression gear with gel inserts designed for athletes. These vests could be heated or cooled to aid in post-workout recovery. When Mark Cuban questioned the science behind the product, Patrick struggled to provide a convincing explanation, leading Mark to drop out.
Despite this, O’Leary and Daymond both made offers: Kevin proposed $500,000 for 15% equity, while Daymond countered with $500,000 for 20% equity. Patrick ultimately chose Daymond’s offer, partly because he doubted Kevin would be a good partner, to which Kevin responded with characteristic bluntness.
1 ‘This is a very bad idea. It howls at the moon. You should take it out behind the barn and shoot it.’
Season 3, Episode 13
Scott Olson, the founder of Rollerblade and the pioneer of inline skating, pitched his latest idea, Skyride, to the Sharks. Skyride is an elevated, human-powered monorail where users propel the “capsule” by pedaling or rowing along an elevated track, which incorporates Rollerblade wheels. It looked like a product out of a sci-fi movie. Olson sought $3 million for a 20% share in the business, despite having no sales but several projects in development.
While the Sharks found the concept intriguing, they were concerned about its high cost and limited applicability. Robert didn’t see a viable consumer market, and Mr. Wonderful bluntly dismissed the idea, comparing it to a creature of the night that should be shot.
