Kevin O'Leary Credits 'Random Decisions' For Biggest Shark Tank Success Stories

Kevin O'Leary, known as "Mr. Wonderful" from Shark Tank, has a message. Entrepreneurs and investors should listen. Never underestimate the power of keeping your options open. In a recent social media post, the Canadian business owner got real about some lessons that he's learned from years of investing and dealmaking.

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"The tiny decisions that make millions end up having a huge impact in your life," O'Leary said. Reflecting on his time on Shark Tank, he admitted that even the savviest investors can't always predict which deals will take off. "You don't know if you have a winner. You have to invest in a lot of deals, and what ends up happening is the smallest, most inconsequential deal – the one you thought was, ugh, it's a flier – ends up being huge five years later."  

That unpredictability is why O'Leary focuses on "option value." According to him, it's about staying flexible and open to anything. "Option value in life is absolutely huge," he said. "Never give up your options. Keep as many options open as you can because the smallest thing can be worth a fortune one day."

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In finance, option value broadly refers to having the flexibility to act when opportunities pop up. In options trading, it's the ability, but not the obligation, to buy or sell an asset at a certain price. For O'Leary, this goes far beyond investing. It's a strategy for life.

On Shark Tank, O'Leary has backed companies like Wicked Good Cupcakes, LovePop, and Plated. These started as small-time operations before scaling into major successes. His philosophy is simple: "Sometimes, the smallest, most random decisions lead to the biggest wins."

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For entrepreneurs, O'Leary's advice is timely. Startups often face tough calls about where to focus their resources. But keeping an eye on the big picture can pay off, surprisingly. For example, O'Leary's investment in Groovebook – a small photo-book subscription service – resulted in one of the show's largest acquisitions when Shutterfly bought it for $14.5 million.

"You've got to stay in the game long enough to win," O'Leary often says. For him, patience and flexibility are key.

This approach isn't just for billionaires or Shark Tank stars. It's advice anyone can use. Whether choosing a career path, saving for retirement, or deciding where to live, the idea of keeping doors open is huge. "Option value – it's a game-changer," O'Leary said.

So, consider O’Leary’s perspective next time you face a tough decision. That small, seemingly unimportant choice might be the start of something big.

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