‘Shark Tank’: Why Robert Herjavec Considers This Deal One of His ‘Favorites’ of the Show

Robert Herjavec has invested in countless companies since Shark Tank premiered in 2009. Partnering with a plethora of talented entrepreneurs over 13 seasons, Herjavec named one deal in particular that he views as a top pick.

Robert Herjavec of 'Shark Tank'
Robert Herjavec of ‘Shark Tank’ | Christopher Willard/ABC via Getty Images

Robert Herjavec took a chance on Tipsy Elves

In a 2021 interview, Herjavec was asked a range of questions on his Shark Tank portfolio, including which investment he ranks as a favorite. The millionaire had a hard time naming just one, but singled out a company from season five that made quite an impression.

“I love them all, but I would say Tipsy Elves, from a Shark Tank perspective,” Herjavec told The Motley Fool. “It was probably the first large investment I made in an area I didn’t really understand. I think I was just going through this phase of, ‘How many more sweater and food companies are going to come on this show?'”

When Evan Mendelsohn and Nick Morton entered the Tank to pitch their ugly Christmas sweater company, Herjavec felt a connection with the entrepreneurs and was confident in their business model.

“I just like the guys,” he remarked. “I thought they were good guys. I believe in what they were doing, and I love the product. We’ve seen it all. That was a company that was almost on the verge of going away. They almost ran out of money because of cash flow issues and inventory challenges, and now we’re at over $100 million. It’s the entire life cycle.”

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‘Shark Tank’ star decided to go outside his comfort zone

Despite having no extensive background in the apparel space, Herjavec offered Mendelsohn and Morton $100K for a 10% equity stake in Tipsy Elves. The internet security guru often gravitated toward tech deals but decided to change gears and diversify his investment portfolio.

“I was just having a moment where I was investing in stuff that I thought I understood,” Herjavec explained. “I think it was part of my education and journey as an investor. I think I felt if I invested in something, I’ve got to really understand it to the point I can run that business. That was probably a little bit of my own arrogance, because I’m a very technical cybersecurity guy.”

Mendelsohn and Morton’s pitch, as well as their demeanor in the Tank, won Herjavec over and prompted him to join forces with the pair. The Shark Tank panelist is glad he took the leap of faith.

“I looked at them, and they were selling $600,000 a year in inappropriate, ugly Christmas sweaters, and I didn’t understand it, but I believed in them,” Herjavec said. “I realize it’s OK if I don’t understand it, if the fundamentals are strong and the entrepreneur is strong. Like every investment, you get to a point, you either go forward or you don’t, and I just went forward.”

Robert Herjavec wants partners that are ‘resourceful and adaptable’

Though his co-Shark Daymond John is known as the fashion icon thanks to his megamillion-dollar company FUBU, Herjavec has taken on more apparel deals since his Tipsy Elves partnership. Investing in companies such as Bad Birdie golf wear and Buttercloth shirts, Herjavec is always open to new business ventures when he finds partners who are up for the challenge.

“I look for people that are highly resourceful and adaptable,” he shared. “Because anybody can work a plan, but plans can change every single day. I think that’s the beauty of Shark Tank.” 

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