Shark Tank: 15 Dark Secrets You Never Knew About The Investors

Shark Tank is one of the few shows left on television that exemplifies the spirit of the American Dream. For eight seasons, the ABC reality show has given startup companies the opportunity of a lifetime by allowing them to pitch in front of a select panel of actual millionaire investors. The investors, commonly referred to as the “Sharks,” are successful entrepreneurs that control business empires, but if you thought that everything was that perfect behind the scenes, think again.

The truth is that the investors of Shark Tank have just as many secrets as the viewers who have made their show a success. It’s important to remember that the Sharks are real people, which mean they too have made mistakes, lost money, made poor investments, and worked degrading jobs before they became the business moguls that they are today.

You may know that Mark Cuban is the owner of the Dallas Mavericks or that Lori Greiner is the Queen of QVC, but these next juicy tidbits below might surprise even the most diehard Shark Tank fan. Investors Robert Herjavec, Lori Greiner, Daymond John, Mark Cuban, Barbara Corcoran, and Kevin O’Leary, aka Mr. Wonderful, have all been a part of Shark Tank since season one, but there’s still plenty you don’t know about these high-profile business sharks.

Here are the 15 Dark Secrets You Never Knew About The Investors Of Shark Tank.

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15 Mark Cuban’s Expensive NBA Fines

It’s no secret that Mark Cuban is a fan of basketball. In fact, he’s such a fan that in 2000 he purchased a majority stake in the NBA’s Dallas Mavericks for a whopping $285 million. It turned out to be a good move; in the following ten years, the basketball team won 29% more games in the playoffs and won the NBA finals in 2011 when they defeated the Heat.

That success has come at a major price, however. Cuban’s ownership has been the source of numerous controversies involving league policies. During his time as the Maverick’s owner, Cuban has frequently come under fire from the NBA for public statements regarding the league and referees.

In the future, the investor should learn to keep his cool, as his temper has led to 13 incidents where he’s been fined an estimated $1.66 million! Cuban’s paid the largest fine in NBA history, about $500,000, more than what the businessman would cough up during most deals on an episode of Shark Tank.

14 Kevin O’Leary’s Political Campaign Was Over $200,000 In Debt

As we’ve recently seen with the Presidential election, businessmen and politics go together like chocolate and peanut butter. Kevin O’Leary had the same sentiment in January 2017 when he decided to enter the race to lead Canada’s Conservative party.

At first, O’Leary’s campaign was mopping the floor with the competition. Although he was leading in most of the polls, Mr. Wonderful dropped out of the race just a few months later in April 2017, leaving his political campaign more than $200,000 in debt.

According to the rules of the Commissioner of Canada Election, O’Leary is not able to pay the debt off himself or loan the campaign money. Instead, the businessman must ask for individual contributions to his abandoned campaign for a maximum of $1,550 each until his debts are completely wiped out. Given the high-profile connections that O’Leary has made over the years, we figure it shouldn’t be too hard.

13 Not Every Deal is a Winner

You’d think that with all of the products invested in over the years, the Sharks would be raking in the dough. For the most part, you’d be right. The investors have made millions over the years on various Shark Tank products, but that doesn’t mean every deal they’ve made over the last eight seasons have been winners.

Companies like Toygaroo went belly up after striking a deal with Mark and Kevin because there wasn’t enough demand for their product. Others, like You Smell Soap, simply had too many orders to fill after the show and decided to sever their ties with their investors.

One of the biggest deals gone wrong was with an exercise machine called the Body Jac. When creator Jack Barringer, aka Cactus Jack, was asked by Barbara Corcoran to lose 30 pounds in order to guarantee his product worked, he successfully put his money where his mouth was.

Unfortunately, the deal later fell through anyway, with Corcoran calling it the worst investments in Shark Tank history.

12 Mark Cuban Is a Guinness World Record Holder... For Shopping

Other than breaking the record for the biggest fines paid in NBA history, business mogul Mark Cuban has  been breaking records for decades, even being introduced into the Guinness Book of World Records – as the world’s biggest online shopper.

That’s right, the Mavericks owner made the biggest single e-commence transaction in 1999 when he purchased an entire plane over the internet. After selling his company to Yahoo for $5.7 billion, Cuban decided to celebrate by purchasing his very own private jet.

Instead of letting his broker negotiate the sale, however, Cuban purchased the jet himself over the internet with a click of a mouse. The Shark’s Gulfstream V Jet was the largest online purchase is history when it was purchased for an estimated $40 million, cementing Cuban as the world’s biggest online shopper.

11 Kevin O'Leary Lost Mattel Millions of Dollars

You would think, what with their millions of dollars, that the Sharks have never made a bad business deal in their lives - but you would be wrong. If history has taught us anything, it’s that nothing is every a sure thing in business, and the investors on Shark Tank aren’t immune to a bad day at the office either.

O’Leary’s The Learning Company was one of the biggest educational software companies in the world at one point. Toy giant Mattel took notice, and in 1999 they bought the company out for an estimated $4 billion. Unfortunately for Mattel, The Learning Company had a history of net losses and collapsing revenues and the deal became known as one of the biggest disasters in acquisition history

When all was said and done, Mattel ended up losing $105 million dollars on the deal and O’Leary was subsequently fired as CEO of the company, but not before he cashed his shares out before the plummet, pocketing nearly $6 million as a result.

10 Lori Greiner Sold to QVC's Rival

Known as the “Warm-Blooded Shark” on the show because of her empathy towards budding entrepreneurs, Lori Greiner built her fortune on the flagship shopping network, QVC. Although she’s now knows as the “Queen of QVC,” she didn’t always have the loving relationship with the channel she has today.

Lori’s first product was a specialized jewelry box in order to keep earrings and other accessories organized. When she had an opportunity to pitch the product on QVC on air, the network passed on the offer. Instead, she pitched the product on the network’s rival channel, HSN, to enormously successful results.

Although they initially rejected her first product, QVC and Greiner have had a fantastic relationship ever since, with the investor as the host of several shows on the network over the years.

9 Horrible First Jobs

Shark Tank investors

Like many of the entrepreneurs pitching their ideas on the show, the investors themselves do not come from a background with money. Many of the Sharks started at the bottom of the food chain, working degrading and difficult jobs that nobody wants.

Like a lot of youngsters, Kevin O’Leary’s first job was working at a mall in an ice cream parlor. He was fired after only his second day of work after he refused to scrape off the gum from underneath the tables. O’Leary said that this incident shaped his future, swearing that day that he would never work for anyone else other than himself.

Likewise, Mark Cuban got his first lesson in entrepreneurship at a young age when he started selling garbage bags door to door in order to buy a new pair of sneakers.

One of Daymond John’s first jobs was waiting at Red Lobster, which he continued to work at even after his company Fubu became a huge success.

8 Daymond John Blew $20 Million

If you’re a regular guy who's never had a nickel to their name, we admit it’s a little hard not to go on a shopping spree once you come into some money. Sometimes it's nice to treat yourself. However, Daymond John took that philosophy to new heights after his company FUBU became a huge success and blew his first $20 million in the process.

John has said that after initially becoming successful, he got caught up in the millionaire lifestyle, throwing lavish parties with hefty price tags. As a result, he ended up going through $20-$30 million and began neglecting his role as a husband and father.

Only after his spending binge and his wife divorcing him did John realize he needed a life change. He started focusing more attention on his business and family, and finally got back on the right path to becoming the business mogul he is today.

7 Robert Herjavec's Dark Backstory

Most of the investors on Shark Tank come from humble beginnings. Rather than being from families with money, the Sharks are all do-it-your-self-millionaires thanks to their hard work and persistence. However, Robert Herjavec’s fortune is even more astounding when you consider his extremely dire background.

During his childhood while he lived on a farm in Croatia, Herjavec’s father was arrested 22 separate times for speaking out against the communist regime. Because of the pressure, the family left the country and attempted to immigrate to America. However, the family was turned away at the border and eventually found refuge in Canada instead.

Despite his rather tumultuous childhood, Herjavec went on to become one of America’s most recognizable business leaders through his insanely successful global IT security firm, the Herjavec Group.

6 Mark Cuban's Company Was Sued

We all like to believe that the companies that get deals on Shark Tank go on to become successes. Sadly, this isn’t always the case. Often times, companies are riddled with behind-the-scenes problems, and Mark Cuban always seems to pick the ones with the most drama.

In season 8, Cuban purchased 15% of company Under the Weather for $600,000. The Cincinnati-based company produces weatherproof tents for outdoor sporting events. However, Under the Weather is now facing a lawsuit from their former partners, Connecticut-based company Anthem Sports, who claims that Under the Weather is infringing upon their weatherproof pods that they sold online.

According to the suit, Anthem sold Under the Weather tents until 2015 when they became too expensive for the retailer. Now that Under the Weather has made a deal with Cuban, Anthem is taking a preemptive strike so ensure that their new pods, which they sell now, do not infringe on Under the Weather’s patents.

Depending on what the court decides, Cuban soon might not be the only person allowed to sell weatherproof tents for his Mavericks games.

5 Robert Herjavec Hated Mark Cuban For the First Two Seasons

Despite some trash-talking and undercutting one another on deals, for the most part, the Sharks on the show seem to get along friendly enough. However, the smiles and light jabs on camera are a different story altogether behind the scenes, with some arguments heating up to the point of fighting words.

According to Robert Herjavec, one of those arguments led the Shark to harbor resentment towards fellow investor Mark Cuban. Due to Cuban’s boisterous personality, Herjavec claims that tensions were high before even stepping on set together.

The tension boiled over into one of the most heated arguments in Shark Tank history when Herjavec became disgruntled that Cuban was investing his money in almost every pitch on the show.

Although Herjavec claims that he hated Cuban during the first couple seasons, the two have learned to deal with one another over the years – but that doesn’t mean that tempers don’t fly off the handle every now and again in an episode.

4 Marc Cuban Has Produced Some Bad Movies

Sharknado 3 Mark Cuban Ian Ziering

Mark Cuban is definitely the most high-profile investor on Shark Tank. Along with his very big personality and the fact that he owns an NBA team, Cuban is also widely known for his other passion: movies. Over the years, Cuban has produced a series of critically-acclaimed films, including the Oscar nominated Good Night, and Good Luck directed by George Clooney.

While he’s produced some gems over the years, Cuban is also responsible for a ton of cinematic garbage. He’s responsible for horror disasters such as Black Christmas and Turistas, as well as sophomoric comedies like One Last Thing.

Although he’s popped up in Sharknado 3, the worst film Cuban has been responsible for is no doubt Serena, a botched drama from 2014 starring Bradley Cooper and Jennifer Lawrence. Despite the A-list talent, the movie was torn apart by critics and single-handedly tanked 2929 Productions.

After a string of misses, Cuban finally put his film distributor, Magnolia Pictures, up for sale in 2011.

3 LL Cool J Helped Save Daymond John's Fubu

Daymond John has built his empire on the back of FUBU, his hip hop apparel company. Starting with just a line of hats, FUBU has become one of the biggest brands on the planet, but the company almost went out of business even before it even got off the ground.

Between 1989 and 1992, John had to temporarily shut down FUBU three separate times when he continually ran out of capitol. Even after John’s mother mortgaged her house, there still wasn’t enough left to keep the business afloat.

Things took a turn when rapper LL Cool J, who was from the same neighborhood as John, decided to wear a FUBU hat in one of his GAP commercials. The free marketing was just the kind of push FUBU needed to gain steam and become the powerhouse company it is today.

Ironically, GAP didn’t realize they were giving FUBU free advertising until a month later, at which point they fired the ad executives responsible for the commercial.

2 Robert Herjavec's Depression

It’s an old saying that money doesn’t buy happiness, and no one can attest to that more than Shark Robert Herjavec. Despite his millions of dollars and fame, Herjavec battled with depression and contemplations of suicide when he and his wife separated in 2014.

After the separation, Herjavec’s children refused to talk to him, leading the investor to a very dark period of his life. At one point, Herjavec was so depressed that he stood on the balcony of a Toronto hotel and seriously considered jumping to his death. Thankfully, before he made the decision to jump, Herjavec called his pastor, who was able to provide him help from a shelter that gives emergency care to people in need.

Through volunteering in soup kitchens, Herjavec was able to put his problems into perspective and overcome his depression. It led to him joining the cast of Dancing with the Stars where he met his fellow dancer and future wife, Kym Johnson.

1 The Investors Frequently Change the Deals

Shark Tank presentation being pitched to the sharks

While most episodes of Shark Tank feature entrepreneurs getting the deal of their dreams, often times, the deal you see on camera isn’t the one the companies end up with. Although all the negotiations on the program are real, the handshake agreements frequently fall apart when the cameras stop rolling.

In a survey done by Forbes in 2016, it was discovered that nearly 73% of businesses did not receive the precise deal that’s brokered on the show. In most cases, the terms of the deal are tweaked or altered. This isn’t always a bad thing, with some of the owners stating that the deals still ended up being productive for their businesses.

However, about 43% of the surveyors stated that their deal completely fell apart after the show. In some instances, the Sharks will completely pull out of the agreement or change the terms so much that the businesses are forced to pull out themselves.

While many businesses still say they’d do Shark Tank all over again if they had the chance, we have to wonder just how many took a certain deal that ended up never happening.


Do you know of any other dark secrets about Shark Tank's investors? Let us know in the comments.

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