Thousands of entrepreneurs each year have pitched their businesses on “Shark Tank” since the hit show started up in 2009.

Some of the people involved have gone one to be incredibly successful after winning investment from the sharks.

However, some of the most memorable pitches have been the worst ones.

They all have their reasons for being so bad, some are just the product in general and some are due to the arrogance and stubbornness of the entrepreneurs.



Arthur Grayer and Michael Wooley were seeking $50,000 for 10 percent of their children’s backpack alternative company Vestpakz.

Unfortunately, the only thing going for them was two cute kids modeling the product.

Michael’s daughter invented the product when she was 12 and he made a licensing deal with Arthur in 2013.

The product went around in 75 Walmart stores.

The annual sales of $10,000 were poor, especially with the context of being in Walmart.

However, the Sharks were intrigued by the story of Michael’s daughter winning an entrepreneurship competition and even making it onto Oprah Winfrey’s talk show.

All of this occurred in 2003, and Michael’s daughter was now 27.

The investors exploded in laughter at the revelation.

The guys didn’t get a deal.

Tycoon Real Estate

The founder of Tycoon Real Estate is Aaron McDaniel.

Unfortunately for him, the Sharks not only hated the product idea but some of them hated the entrepreneur behind it.

Aaron pitched his real estate crowdfunding service as a way for average people to invest in real estate.

He failed to convince the Sharks that it was a safe model and that he was someone to be trusted with money.

Mark Cuban said that his idea was “scammy.”

Barbara Corcoran thought it was “spooky.”

And O’Leary — who was actually interested in making a deal — asked McDaniel if he had a criminal record.

Shark Tank can either make or break a company.

Speaking afterwards Aaron stressed his company was not “sleazy” and wasn’t looking to “swindle money out of anyone.”

Cougar Energy

Ryan Custer pleaded for a $150,000 investment in return for 30% of his company Cougar Energy.

The idea behind it was to make energy-drink shot bottles specifically tailored to single, middle-aged women wanting to date young men like himself.

The idea was cliched in general and didn’t go down well with the Sharks.

Unfortunately, he only had $60,000 in sales over three years.

His pitch is proof that a gimmick can only take a brand so far.

Technology Enabled Clothing

Scott Jordan was looking for $500,000 for 15 per cent % equity in his company SCOTTeVEST.

The company makes vests that accommodate all of your gadgets.

He initially impressed the investors with $5 million in sales, so then O’Leary offered $1 million for 30 per cent.

Scott made a call to one of his advisers and decided that the Sharks were low-balling him.

So then, Scott began to point and yell at the investors, basically telling them they were worthless.

Yes… not exactly the best way to build professional relationships.

Copa di Vino

James Martin originally pitched his wine company Copa Di Vino in season two.

He left a few deals on the table because he found the offers too low.

He did the same thing in season three.

It’s understandable that James would turn down O’Leary’s offer of $600,000 for 51 percent equity during his first trip to the Tank.

However, he was reluctant in season three – this was quite frustrating since the Sharks were willing to negotiate on his terms.

He spent way too long negotiating with the Sharks in his second pitch that they were convinced that he was using the show as an advertising platform and had no intention of ever making a deal.

His second pitch made Cuban and John start looking out for what they call “gold diggers” on the show.

Corcoran told James: “I didn’t like you then, and I don’t like you now”.

Image credit: ABC/Andrew Eccles

Follow WhatNews on YouTubeTwitterLinkedin, and Facebook