It’s been 16 years since Kevin O’Leary sold the Learning Company for $4.2 billion, but the Marlborough Street resident didn’t take the money and head off to retirement. He’s since made a name for himself as Mr. Wonderful on ABC’s Shark Tank, investing in companies like Boston’s Wicked Good Cupcakes, which he calls one of the most successful to ever come out of the show. The shark who believes “Business is war; it’s not a social club” shared a few tricks of the trade.
What financial lesson did you learn the hard way? No matter what anybody puts forward as a forecast, it’s just that; it’s a forecast. … Being flexible, being able to pivot and understanding that you’re going to make mistakes with certainty—100 percent probability you’re going to make mistakes—and in doing that you leave enough flexibility and you can actually adjust when those hits are taken. Most entrepreneurs that fail can’t pivot. They can’t adjust.
Well, obviously Uber has been extremely disruptive, very controversial, a service I use in every city I travel to around the world, when available.
What’s a misconception people have about you after watching the show? Well, I may be the only shark that tells the truth, and the reason I do is that I actually think I’m trying to help you save your money. … If I tell you that your business has no merit and you’re going to go bankrupt and waste all your family’s money, I’m telling you that because it’s true, and so you can cry now or cry later, after you’re bankrupt. I’m not trying to make friends, I’m trying to make money. … So being honest caused me a reputation of being a mean shark, but that’s not true at all. I’m the nicest shark and the only one who tells the truth.
I would have to say one of the best cellars is Grill 23. They particularly have a fantastic sommelier there.
A lot of these deals are very disruptive, they’re very innovative, they’re very risky, they’re out-of-the-box thinkers…but the reason they’re able to capture capital and the imagination of investors is they have these three attributes. So number one is they’re always able to articulate their idea in 90 seconds or less. … Number two is…they’re able to articulate and explain a roadmap as to why they’re the entrepreneurs that should execute the business plan. … And lastly, and this is the one that actually is the downfall of many that sound so promising initially…if you don’t know the numbers, you’re dead.