Kevin O’Leary is widely recognized as the sharp, unapologetic investor from the hit show Shark Tank. But behind the persona is a man with deep roots in business. His career spans decades, and he has collaborated with some of the most influential minds in tech, including Steve Jobs himself.
Beyond television, Kevin actively works with rising entrepreneurs and often invests in their ventures. He doesn’t just write checks. He shares frameworks. Actionable ones. And recently, he laid out a few clear principles for anyone who dreams of starting a business. According to him, these are essential steps a young entrepreneur must follow to improve the odds of long-term success.
Let’s walk through what he actually said.
1. Invest two full years in learning before launching
You may be tempted to jump straight into your startup idea. But Kevin strongly advises against that. His recommendation is this: before you start your business, get a job in the same industry. Join a company that operates in the space you’re interested in. Stay there for at least 24 months. That means two entire years of soaking up insights and learning on the ground.
He even says that if the job is unpaid, take it anyway. Treat it as an investment. Think of it like a field-level MBA. If necessary, apply for internships.
Why go through this? Because real-world exposure will give you clarity about how that industry works. You’ll get a front-row view of the structure, the moving parts, the bottlenecks, and the revenue logic. You’ll gain intuition that textbooks and online courses can’t offer.
Kevin believes these two years will protect you from making beginner mistakes when you finally start. You will make fewer blunders, waste less time, and know how to make decisions faster and with more accuracy. In his eyes, this is non-negotiable.
2. How to raise money without losing your head
So you’ve completed the 24-month industry immersion. What now? Kevin says this is the right moment to launch your venture. But here comes the next big question. Where do you get the money?
O’Leary is very clear here. Don’t go for a big bank loan right away. Don’t chase angel investors or venture capitalists. Start lean. Raise a small amount of money from friends and family in the form of a loan. Not a donation. A loan. Something you commit to paying back.
He gives a simple figure: ten thousand dollars. In local context, that could mean three to five lakh taka. This should be an amount that helps you begin, but won’t destroy relationships if things don’t go according to plan.
Even after gaining industry experience, you’re still not immune to risk. The early stage is fragile. You might take time to get traction. So don’t raise money like a gambler. Start with what’s reasonable and test the waters. That’s what smart entrepreneurs do.
3. Brace yourself for the reality of failure
Let’s say you now have both the experience and the capital. Even then, success will not fall into your lap. O’Leary stresses that entrepreneurs must mentally prepare for the possibility of failure. And not just a single failure. Multiple ones.
According to him, having a great idea and enough cash does not guarantee anything. These elements only increase your chances. But business is chaotic. Markets shift. Customers behave in unpredictable ways. Regulations change. Competitors move faster. You are never fully in control.
So expect that your first few attempts might flop. You might get rejected. You might lose money. And if you aren’t prepared for that, the psychological hit could destroy you.
Kevin is brutally honest here. He says that in the first few years, failure is almost guaranteed. And that is okay. What matters is whether you learn from those failures and adapt quickly. That’s what separates real entrepreneurs from hobbyists.
4. Presentation is not optional, it is strategy
In business, you won’t just be sitting behind a desk. You’ll constantly interact with people. You’ll need to pitch, explain, negotiate, and build trust. And how you show up in those moments can make or break you.
O’Leary says you must pay close attention to your confidence, your dress, and your communication style. These are not vanity points. They are signals. People pick up on them instantly.
If you’re insecure, it will show in your voice and body language. If you’re arrogant, that will show too. Both are damaging. What you want is grounded confidence.
So what’s the fix? According to Kevin, it all starts with awareness. Be mindful of your posture, your clothes, your tone, and your timing. Your confidence should come from knowledge, not from ego. When you truly understand your business and believe in your product or service, confidence will follow naturally.
Kevin says you won’t even need to speak for people to sense it. Eye contact, body movement, voice pacing, everything will communicate your authority. But if you ignore this, your chances of being taken seriously drop fast. And in business, first impressions often become final judgments.
Kevin O’Leary is not trying to sell you a shortcut. He is laying out a blueprint that filters out the unserious. Learn first, raise modestly, expect setbacks, and project trustworthiness.
If you follow this sequence with intent, your odds of building something meaningful go way up. And in today’s chaotic market, playing it smart is the real power move.
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