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The 20 Worst Shark Tank Deals of All-Time

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Entrepreneurs dreamed of landing a spot on "Shark Tank" to make a pitch for funding their idea or busness, but some of the deals which have been struck on the show were not as good as they might have hoped.

There has been a long history of bad deals along with the good ones and missed opportunities, but some take the cake as the worst deals in the history of the show.

If you think that everyone that struck an agreement on the show was happy later, you need to take a look at a few that haven't ended well. We've uncovered the 20 worst Shark Tank deals for your consideration.

20. Doorbot/Ring Doorbell

Jamie Siminoff appeared on Season 5 of Shark Tank and made his pitch to the sharks. He was asking for an investment of $700,000 to get his idea off the ground for a video doorbell system.

The business was initially called the Doorbot, but the name later changed to Ring Doorbell. Kevin O' Leary bit on the deal but insisted on 10 percent of the sales royalties and also a 5 percent stake in teh company.

Siminoff made a counteroffer and the deal was rejected by O' Leary. Siminoff walked off without the deal. The sharks missed out big time as Jezz Bezos and Richard Branson decided to invest in the Doorbot and it was changed to Ring when Amazon bought it from Siminoff for $1 billion. Talk about a missed opportunity.

19. Grinds

Pat Pezet and Matt Canepa are the owners of Grinds, a company that sells pouches of chewable coffee. Daymond John and Robert Herjavec struck an agreement with them for an investment of $75,000 in exchange for 15% equity in the company.

When the show ended the negotiations continued but the negotiations went south and the deal was called off. That same year Grinds had a successful year without the help of the sharks who tried to alter the original deal and the company brought in $1.35 million with the following year anticipating more than $4 million.

18. Three65 Underwear

William Strange came onto the show pitching a subscription model for men’s underwear. He walked away with a deal from Janine Allis and Naomi Simson, who offered him $60,000 for 25% of his company each.

However, once again, things changed once the cameras were off. Strange was working on not one, but two startups at the time.

The Sharks warned him that he would eventually have to make a choice between the two and so he did. Strange wrote about his decision to turn down the deal in order to go with his business, Start Up Smart:

17. Hy-Conn

Hy-Conn is an invention that was the idea of firefighters. The product is a connector that hooks a hose to a fire hydrant faster and more efficiently than the old traditional method.

When the firefighters pitched the deal, Mark Cuban was the shark that bit on the line. He made an investment of $1,25 million into the Hy-Conn company, but the deal ended up going south.

There were issues with the licensing of the product as well as some issues with the negotiations with Mark Cuban as he tried to change the deal with teh founders of Hy-Conn. As it ended up, the deal that was previously agreed upon fell through making this one of the worst deals to come out of "Shark Tank."

16. Qubits

Qubits is a toy that was created by inventor Mark Burginger. He appeared in Season 1 of "Shark Tank" to make his pitch for an investment of $90,000. He offered in exchange, a 51% stake in teh equity of the company.

The offer was one that Daymond John bit on. He threw out a condition to the funding though. He told Mark Burginger that he had to at least try to pair with one of the leading toy companies, and Mark agreed to this. Some suggested that Mark made no effort while other reports stated that he didn't have any success in his efforts.

Either way, he was not able to satisfy this condition of the agreement and the deal ended. We've heard reports that the company went under.

15. Hill Billy

Hill Billy is a clothing line. The owners of the company went on "Shark Tank" asking for an investment of $50,000 in their company in exchange for a 25% stake in the company.

They had some discussions with the sharks and Jeff Foxworthy and Daymond John both showed interest in making the company a skiing gear and snowboarding company, but things went downhill.

The owners admitted that they were not really there to strike a deal with any of the sharks. They didn't want the money, they just wanted to appear on national television to plug their new business.

This was one of the worst "Shark Tank" deals in history because although nothing illegal took place, it was a fraudulent representation in nature.

14. The Squirrel Boss

The Squirrel Boss owner appeared on the fourth season of "Shark Tank" to pitch the invention to the sharks. The product is a bird feeder that comes with a small remote control that would send an electrical current through the feeder and into the squirrels if they attempted to rob the contents out of the feeder.

It was intended to solve the problem of squirrels stealing bird food. The inventor pitched it as being harmless to the squirrels but the sharks begged to differ. It was considered to be cruel to animals because a jolt of electricity would hurt.

The second issue they had with the contraption is that nobody wants to spend all day monitoring a bird feeder for squirrel activity so they could catch them in the act, push the button, and shock the little critters. The inventor offered a 40% stake in the company in exchange for a $130,000 investment.

This was one of the worst pitches in the history of the show. Not only did the sharks show no interest in investment, but they also laughed the inventor off of the stage.

13. Toygaroo

The owners of the Toygaroo toy company appeared on "Shark Tank" in 2011 to make their pitch to the sharks. The premise of the business was unique and they did a great job of explaining that the company that both rented and sold toys gave parents an option for saving money.

Since kids get sick of toys quickly, this gave them the chance to try them out on a rental basis and buying them later if it worked out. Mark Cuban was a taker on this deal and he invested $50,000 in the company.

Within a year, Toygaroo stopped taking orders, suspended their social media then filed for bankruptcy. In the end, Cuban lost every cent of his investment and there was never a reason given for the company's failure.

12. Breathometer

One of the worst deals in the "Shark Tank" history has got to be the Breathometer. This invention was a device that acted as a portable breathalyzer and it could be plugged into the audio jack of a smartphone.

It would give a reading of the blood alcohol level along with feedback to let the user know if they could legally operate a motor vehicle, or if they should find a ride. While this sounded like a good idea, and all five sharks came together to invest $1 million for 30% of the company, it ended up being a total bust.

After the investment was made the company ran into a plethora of problems. For starters, the company had issues fulfilling their orders. On top of this, the Breathometer was tested and found to be a lot less accurate than the company had guaranteed it for.

On some occasions it reported the BAC to be far below what it actually was, suggesting that people could drive when in reality they had no business behind the wheel. The Federal Trade Commission got involved in the investigation and then ordered Breathometer to make full refunds to all of its customers.

11. The Bouqs Company

The Bouqs Compan is an innovative florist business offering direct from farm to table sales. By cutting out the middleman, owner John Tabis believed that he could offer lower prices and become more successful.

The company was based in Venice, California. He appeared on "Shark Tank" in 2014, and the pitch that he made wasn't very well received by the sharks. Instead of meeting his request with interest, they seemed to pick the business apart.

The business was set upon a different kind of business model that they didn't like at all so they all passed on the deal. Within just a couple of deals, thanks to other investors who saw the potential and invested $23 million in Bouqs, it ws selling $43 million worth of flowers a year.

The business took off and became a massive success and this was one of the biggest misses that the sharks made, making it one of their worst errors in judgment.

10. Chef Big Shake

Shawn Davis is the owner of Chef Big Shake and he appeared on "Shark Tank" to pitch his business proposition. He was an experienced chef and he had a great idea for a business.

Chef sold frozen hamburgers, fish burgers, chicken burgers shrimp burgers. He asked for an investment of $200,000 for a 25% stake in the company. None of teh sharks showed any interest in jumping on board with the deal and sent Davis away with no deal.

Davis made an impressive pitch and the food was good but they felt that it was too big of a risk. Shawn didn't have any problem finding other investors who coughed up $500,000 in investment capital.

The business jumped to earning more than $5 million the following year. Chef Big Shake products were sold in over 2,500 grocery stores and it was one of the biggest misses in the history of "Shark Tank."

9. Coatchex

Derek Pacque is the founder of Coatchex, and he appeared on season 4 of "Shark Tank" to make his pitch. The company was a coat check system tht matches people's faces to their coats.

Mark Cuban thought that the company had some merits but he wasn't wanting to go with teh deal that Derek had originally proposed. He offered Pacque a deal for $200,000 for a stake of 33% in the company.

Pacque declined Cuban's request. In a counteroffer, Cuban offered him the total amount of investment requested for a higher stake in the company. Again, Derk declined the offer.

This would be a deal that Cuban would regret losing because Coatchex landed major contracts for upscale events and the company grew to be a multi-million dollar revenue generator. This was one of the worst passes that the sharks made by offering bad deals which were declined.

8. Proof Eyewear

Proof Eyewear is one of a kind handcrafted eyewear company. The products are made from sustainable wood. The owner of the company is Brooks DAme.

He and his two brothers made their pitch to the sharks hoping to gain investment to advance their eco-friendly frame company. The company used plant-based plastics and wood frames which were all eco-friendly.

The sharks seemed to like the product and O' Leary offered to invest $150,000 if they gave him 25% equity in the company in addition to royalties.

The brothers turned down his offer because of the royalty inclusion. Herjavec also made an offer that they didn't feel would be fair and they declined his offer as well. They were not able to get the deal that they were asking for from the sharks so they left not taking any of the offers.

As it turned out, this was a big goof on the part of the sharks because the company ended up beign a raging success with retailers selling their brand in 20 countries throughout the world. In just a year they hauled in a revenue of $2.5 million and the company has continued to grow. When you offer bad deals you miss out.

7. Echo Valley Meats

David Alwan is the owner of Echo Valley Meats. He is a connoisseur of meats and he appeared on "Shark Tank" hoping to get a deal in the fourth season.

He brought samples of the meat and the sharks were all impressed with the flavor, but they didn't enjoy his presentation. they weren't convinced that David Alwan had what it takes to be successful in business.

They felt his business plan was unclear and therefore, they turned him down. This ended up being one of the worst deal decisions tht they had made.

He was offering them a chance to get in on the action, which ended up being worth $1.4 million shortly after the show aired. Later, Alwan came back on "Shark Tank" and Cuban took him up on a deal.

6. Xero Shoes

Steven Sashen and Lena Phoenix are the inventors who came up with a novel invention for shoes. Instead of using the high amount of padding, they believed that their running sandals would provide ample foot support for running while making it feel like you were going barefoot.

The two made their intriguing pitch to the sharks and even though there was interest, Kevin offered them the requested amount in exchange for a 50% interest in their company.

This was too much to ask for the investment and they felt that the deal was completely unfair, and they walked away. After walking, their sales picked up and within a year they were earning $2.5 million annually.

The product and company became a big success, no thanks to the horrible deal offer they were smart enough to turn down.

5. Body Jac

Body Jac is the dreamchild of Jack Barringer. Jack had problems losing weight and it was difficult for him to do pushups. He invented a machine that would help people do push-ups and called it the Body Jac.

Jac made his pitch to the sharks and Barbara Corcoran told him to lose 30 pounds to get an investment from herself and Kevin Harrington. He lost the weight and they invested the funds.

Corcoran had put $50,000 into the deal and the Body Jac was a big bust. This was one of the worst deals for Corcoran because she lost her $50,000.

4. You Smell Soap

Megan Cummins is the owner of a luxury soap company called You Smell Soap. She made her pitch to the sharks, then cut a deal for a $55,000 investment from Herjavec in exchange for 20% equity in the company.

After the show was done, she received a contract from Herjavec which made her an offer of $55,000 for half the company. She rejected the altered deal because it was one of the worst attempts to change during the negotiation process.

3. ShowNo towels

ShowNo towels is a business that centers around a combined towel and Pancho, created by Shelly Ehler. She made her pitch on "Shark Tank" with her patented product. She asked for $50,000 and Lori Greiner bit on the deal.

After the show, the deal turned wretched and fell apart. Greiner kicked her to the curb, and after six years the business ended.

2. Sweet Ballz

Sweet Ballz is a cake ball company owned by James McDonald and Cole Egger. They made their pitch to the sharks asking for $250,000 for 25% of the company.

Mark Cuban bit on the deal but it wasn't long before things took a nasty turn. The two partners had a falling out and got into a lawsuit after the deal was struck.

It even went to far as to have a restraining order issued.  However, since that time Sweet Ballz has managed to sustain their business and is thriving today.  Their products continue to ship to many of the top food service providers in the United States.

1. Night Runner

Doug and Renata Storer made their pitch to the sharks for an investment to fund their Night Runner business. The product they created was running shoes that were outfitted with rechargeable LED lights that would light up the trail ahead.

Herjavec bit on the deal and offered $250,000 for a 15% stake in teh company. It seemed like the deal was struck and everything was a go until the owners changed their minds.

They decided that it would not be in their best interest to take the deal. After the show, they went on to generate $1.5 million in revenue from the company. This was one of the worst deals for Herjavec who thought he had a good investment, but they hung him out to dry and walked away.

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Allen Lee

Written by Allen Lee

Allen Lee is a Toronto-based freelance writer who studied business in school but has since turned to other pursuits. He spends more time than is perhaps wise with his eyes fixed on a screen either reading history books, keeping up with international news, or playing the latest releases on the Steam platform, which serve as the subject matter for much of his writing output. Currently, Lee is practicing the smidgen of Chinese that he picked up while visiting the Chinese mainland in hopes of someday being able to read certain historical texts in their original language.

Read more posts by Allen Lee

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