‘Shark Tank’: Here’s How Kevin O’Leary Really Feels About Missing Out on This Best-Selling Product

Many millionaires (and billionaires) have launched their careers on the Shark Tank stage. Among the dozens of entrepreneurs who’ve gone on to bigger and better things, there’s one product in particular that Kevin O’Leary — aka “Mr. Wonderful” — has strong feelings about.

Kevin O’Leary didn’t get the name ‘Mr. Wonderful’ on ‘Shark Tank’ from being a pushover

Kevin O'Leary speaks on stage
Investor and TV personality Kevin O’Leary of the show ‘Shark Tank’ attends the 2016 Interbrand Breakthrough Brands Summit | Matthew Eisman/Getty Images

The Canadian businessman, author, politician, and television personality on ABC’s Shark Tank co-founded O’Leary Funds and SoftKey. He now sits in one of the “shark” chairs offering to make a deal with entrepreneurs, or ultimately saying “you’re dead to me.”

O’Leary has contributed over $8,543,000 on-air, according to Sharkalytics. That equals 40 deals across 131 episodes of Shark Tank.

“I’ve had many, many successes on Shark Tank and many, many failures. That’s the nature of venture investing,” O’Leary told CNBC Make It. “But, I’ve had some really big winners.”

He continued, “Plated, one of my deals, got sold to Albertsons, the grocery chain, for $300 million dollars. That’s the biggest exit in Shark Tank history.”

Another winner in O’Leary’s portfolio is Groovebook. It’s a photo-printing app subscription service. It sold to Shutterfly for $14.5 million.

“The deal was only 18 months old” at the time of the sale,” O’Leary said. “[The co-founders] became millionaires. That’s a great outcome.”

Mr. Wonderful hasn’t only acquired success stories. There are plenty of deals he passed on or was out-bid by another shark. Among those he didn’t see doing well is now a billion-dollar business.

O’Leary passed on this billion-dollar product

Way back in 2013, the chief founder of a video doorbell company stood in front of the sharks. Ring CEO (then called “Doorbot”), Jamie Siminoff, asked for a $700,000 investment in exchange for 10 percent equity in his company.

No shark made an offer except O’Leary. Siminoff passed and walked away with nothing. Five years later, after “Doorbot” became a smart-home security business, “Ring,” sold for a reported $1 billion to Amazon.

During the GeekWire podcast, Numbers Geek, Siminoff was asked if he’d have done anything differently.

“I’ve had many private failures, but they’re not I guess on ABC for twelve minutes on primetime TV,” he said. “You know, I think I probably would have done the same thing. The company, it turned out, was worth that or more.

Here’s how O’Leary really feels about letting Ring slip through his fingers

At the time the Amazon deal was announced, O’Leary said it was “probably the biggest miss” in the show’s history, then alluding to the fact that he first passed on Plated but offered them a deal at a later point.

He went on to say there was obvious promise, but Siminoff came in too early.

“I liked [Siminoff] a lot. I thought he was a great sales guy, but at that time his valuation was insane,” O’Leary told CNBC.

“I never think about it a second time, I really don’t. I feel that the road is always going forward. You can’t go looking back — you can’t second guess yourself. You have to do what you think is right in the moment…For that time, I made the correct decision.”

O’Leary had nothing but kind words for Siminoff saying, “When you’re sitting in the Shark Tank, you can feel the aura of greatness. He had it.”

He then elaborated on how he ultimately feels about losing out on Ring’s success.

“Do I regret I don’t have an extra $100 million dollars today? Sure, but my mother taught me ‘never cry over spilled milk’. There’s always another opportunity next time the Shark Tank door opens.”

There are no hard feelings here. Siminoff even joined the sharks as a guest investor in 2018.