Shark Tank is famous not only for serious business deals but also for the worst deals that result in regret of life. Some of the most regrettable deals in Shark Tank history include massive crashes, legal failure and unfulfilled promises.
The sharks have admitted to losing money, facing promotional nightmares or regretting shaking hands on several notorious investments.
Over the years, several multi-millionaire investors have shared their biggest financial regrets from the show. Pointing to operational failures, founder mismatches or mathematical oversight. Here are some of the most regretted deals of Shark Tank that fans still recall today.
Worst Shark Tank Deals They Regret Taking
Breathometer
Breathometer is famously considered the worst investment in the history of Shark Tank. It’s a portable smartphone breathalyzer. Yim initially asked for $250,000 for a 10% stake in his company. $1 million for a 30% equity stake split among all five Sharks. It turned into a massive failure.
The devices were plagued with accuracy issues and the company struggled to fulfill orders. The Federal Trade Commission (FTC) stepped in, ordering the company to refund all customers and halting the sale of the product. Mark Cuban has since called it the “worst execution in the history of Shark Tank”.
Body Jac
An assistive device designed to make pushups easier and relieve joint strain. Jack Barringer sought $180,000 for a 20% equity stake. Sharks Barbara Corcoran and Kevin Harrington agreed to provide the $180,000 for 50% equity, but with one major contingency. Jack had to lose 30 pounds.
Corcoran believed he wouldn’t sell the product successfully while overweight. The product wasn’t a scam; it was a massive commercial flop. Corcoran later named Body Jac her worst deal, stating that she regretted investing in a “fast-talking cowboy selling exercise equipment who needed to lose 50 pounds”.
HyConn
HyConn is a rapid connect/disconnect fire hydrant adapter designed to save firefighters time. Mark Cuban and Lori Greiner agreed to $1.25 million for a 100% buyout. Later negotiated to $500,000 for 50% and royalties.
The deal with Mark Cuban eventually fell apart due to disagreements over company valuation and sales figures. While the initial deal died and the company largely disappeared from the public eye for a while. The business continued to operate independently.
ToyGaroo
ToyGaroo is a “Netflix for toys” subscription service that allows parents to rent toys online. Kevin O’Leary and Mark Cuban invested $500,000 for a 35% stake. The logistics and shipping costs of moving, cleaning and sanitizing large, bulky toys proved to be more expensive than the founders had thought so.
The company went bankrupt in 2012 due to unsustainable logistics and inventory costs. Mark Cuban later commented that the founder spent more time trying to secure television appearances and media exposure. Than focusing on the heavy lifting required to run the business.
Coffee Meets Bagel:
While Coffee Meets Bagel wasn’t a bad deal the Sharks took. It is one of the biggest deals the sharks missed getting into. The founders of the popular dating app Coffee Meets Bagel turned down Mark Cuban’s record-setting $30 million buyout offer on the show. It’s a regret for the entrepreneurs. Viewers criticized the founders for being greedy. While the app has managed to survive and remains operational. It never reached the explosive valuation that would have made turning down a $30 million upfront cash payday a smart strategic move.
The Painted Pretzel:
Thomas secured a $100,000 deal for 25% equity with Mark Cuban. Early in his Shark Tank tenure, Cuban invested in this chocolate-covered pretzel business to “prove a point” to Kevin O’Leary. While the episode generated massive sales for The Painted Pretzel, the business lost cash. The owner implemented a “free shipping” model to please customers. Her profit margin was $15 per unit, while shipping cost $16 meaning the business lost $1 on every single sale until Cuban became involved.
Show No Towels:
Entrepreneur Shelly Ehler secured a $50,000 on the spot cash deal from Lori Greiner for her kids’ poncho-towel hybrid. It was a historic moment on the show but the relationship broke up within a year. Ehler later publicly blogged about her bitter disappointment. Stating that working with a Shark did not look anything like what was presented on television and the company was doomed shortly after. ShowNo towels are no longer available for retail purchase.
Sweet Ballz:
Sweet Ballz was a gourmet cake ball company founded by James McDonald and Cole Egger. They sold bite-sized, preservative-free gourmet cake balls in flavors like Red Velvet and Birthday Cake that could stay fresh on shelves for up to 45 days. They appeared on the Season 5 premiere of Shark Tank and secured a $250,000 deal from Mark Cuban and Barbara Corcoran for a 25% equity stake. Despite a massive incline in popularity, the business quickly demolished due to severe legal disputes and partnership fallouts.
SignalVault:
Chris Gilpin pitched SignalVault, an RFID blocking card that prevents electronic pickpocketing, on Shark Tank’s Season 7 premiere. He secured a joint deal with Daymond John and Lori Greiner. The product uses E Field technology to disable hidden scanners and is designed to protect an entire wallet. After a tense negotiation with multiple Sharks, Gilpin accepted an offer from Lori Greiner and Daymond John for $200,000 for 15% equity. Afterwards, the founder and Greiner’s partnership ended in legal conflicts.
You Smell Soap
Megan Cummins, founder of the vintage-style soap brand You Smell Soap, secured a handshake deal on Shark Tank for $55,000 and a salary. After months of silence, Herjavec’s team returned with an altered, less favorable proposal. Declining this new offer ultimately hindered her company’s growth, leading to its eventual closure.
After taping, Cummins experienced a frustrating six months where Herjavec and his team were completely unresponsive. When they finally replied, the contract terms had changed significantly. Herjavec’s team proposed taking 50% equity for the exact same $55,000 investment. Cummins declined the offer, feeling it was an unreasonable change from the handshake agreement they made on-screen.
CATEapp
Despite scoring a $70,000 deal on Shark Tank with Kevin O’Leary and Daymond John, the CATE (Call and Text Eraser) app deal never officially closed after the show. The controversial privacy app ultimately failed to sustain consumer interest and went out of business by 2013.
InvisiPlug
Invisiplug, pitched in Season 5 by Michael Barzman and Bryan O’Connell, secured a deal with Lori Greiner for $125,000 for 10% equity, plus a $1 per unit royalty until the investment was recouped and 25 cents per unit in perpetuity. The power strip became a major success, expanding into retail giants like Staples and Target.
Michael Barzman, co-founder of the Shark Tank-featured company Invisiplug, faced serious legal trouble after he admitted to a massive cross-country art fraud scheme. He was charged with lying to the FBI after creating and selling dozens of counterfeit paintings attributed to the legendary artist Jean-Michel Basquiat.
Barzman eventually confessed that he and an accomplice fabricated the works, aged them outdoors, and created a fake backstory. The fake pieces famously made their way to a high-profile exhibition at the Orlando Museum of Art before being seized by the FBI in June 2022. Because Barzman previously pleaded guilty to a separate 2016 gun-related charge and subsequently this federal art fraud, these controversies completely destroyed his credibility.
Qubits
During Season 1 of Shark Tank, inventor Mark Burginger pitched Qubits, his flexible geometric construction toy. Daymond John offered $90,000 for a 51% equity stake, but with a firm condition: Mark had to secure a licensing agreement with a major toy manufacturer. Daymond even enlisted the help of fellow investor Kevin O’Leary to pitch major brands like Mattel and Hasbro. Because the major toy companies ultimately passed on the product, the deal with Daymond could not be finalized. Despite the Shark’s deal falling through, the exposure from the show gave the business a major boost.
Common Pattern Behind These Deals
The worst Shark Tank deals that investors deeply regret share a common pattern. They involve fast talking, stubborn founders and overvalued valuations based on hype rather than revenue. Rapid scaling without adequate logistical infrastructure and severe mismanagement of funds post-deal.
The Sharks get swept up in a high-energy pitch from an entrepreneur who relies on salesmanship rather than sustainable business. When the hype fades, these founders often refuse to listen to expert advice. Fail to manage day-to-day operations or prove to be uncoachable. Entrepreneurs often walk into the tank seeking massive investments based on projected future revenues rather than current sales.
They value their companies using unrealistic revenue multiples. Sharks who overpay early on struggle to see a return on their investment. When the company’s actual performance fails to match the optimistic numbers pitched on the show. Some companies experience massive exposure from the Shark Tank effect and get overloaded with immediate demand.
Founders and investors then try to scale production and fulfill orders. Without having the proper supply chain or logistics in place. Order fulfillment falls apart and quality control drops. Customer service fades which quickly sinks the business. Once the capital from the Sharks hits the bank account, the founders misuse the funds.
Such as drawing high salaries before turning a profit or sinking massive budgets into marketing while ignoring issues. The business rapidly runs out of cash. The founders then treat the business as “a game of raising money”. Rather than focusing on the fundamentals required to build a profitable company.
Conclusion
The “worst deals” on Shark Tank fall into two categories. Disastrous investments that cost the investors hundreds of thousands of dollars. Massive rejections of products that later became billion-dollar empires.The worst deals that the Sharks regretted taking involve severe mismanagement, fraud and logistical nightmares.
The conclusion regarding the worst deals on Shark Tank that the investors regret taking is that flawed entrepreneur execution, poor post show due diligence and unsustainable scaling are the causes of investors’ bad luck. While the Sharks accept that a percentage of early-stage investments will fail. Their most unforgettable regrets come from deals where the on-air pitch showed fatal operational red flags, false metrics or mismanagement.
Hey there! I’m Fatima Shoaib, a passionate content writer who believes in creative solutions. Reading enthusiast and storyteller, dedicated and eager to apply my skills to a fast-paced environment and make a positive impact in the industry.Currently focusing on current business projects and goals, I aim to stay passionate about driving results in the business sector. This connection that I felt towards business was because of Shark Talent. I am always exploring to binge into new episodes of Shark Tank. Read more About me.
