Kevin O'Leary always gets straight to the point. The “Shark Tank” investor, known also as Mr. Wonderful, has a detailed message for entrepreneurs raising their first round of funding: Don't assume there's going to be a second.
“You Waste Money, There Won’t be Any More”
In a recent post on X, O'Leary laid it out plainly: "Entrepreneurs, listen up! The biggest mistake you can make with your first round of funding? Assuming there's a second. WRONG! You need to treat that first check like it's the last dime you'll ever raise."
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In a video message, he doubled down: “You’ve got to go into the first saying it’s the last money you raise. You can’t make the assumption that people just want to keep pouring money on losses.”
O'Leary's advice is that every cent matters. If you blow through your initial funding thinking more cash is around the corner, you might be in for a harsh reality check. “Save, save, save, save, and don’t waste money,” he said. “You waste money, there won’t be any more.”
Love the Grind or Find Something Else
O'Leary also believes that passion fuels the best entrepreneurs. If you don't love the work, you'll never survive the stress and long hours that come with starting a business.
“It’s just who you are. It’s your soul, your being,” he said. “That’s what makes great entrepreneurs and great leaders. They want to get up in the morning and get to work.”
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He argues that successful founders don't drag themselves to their desks each day. Instead, they can't wait to get started. That mindset keeps them going when things get tough. Hard work doesn't feel like a struggle when you're passionate about what you do.
“Business is Binary”
O'Leary is known for his black-and-white view of success: “Business is binary. There are winners and losers. You either make money or you don’t.”
That means no half-measures. Especially in your twenties, he says, forget about work-life balance. "If you want to succeed in business, you have to work 25 hours a day because there's someone across the world who will kick your a*s if you don't," he said.
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According to O'Leary, your twenties are the time to go all-in, because you have the energy and fewer responsibilities. It's the foundation you build during those years that will carry you forward.
He also believes that staying informed is non-negotiable. He starts his mornings early with an hour of reading, digging into news from around the world and financial research. “If you make decisions without relevant information, I guarantee you, you will lose money 100% of the time,” he said.
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