10/08/2011 08:38 EDT | Updated 12/09/2011 05:12 EST

Five Business Lessons From Steve Jobs


A lot of people have said a lot of great things about Steve Jobs. And for good reason: he built the world's second-most valuable company, with billions in profits and products that have improved every aspect of our lives. But Steve didn't get there by being a soft, fluffy, Kumbaya-type leader. I know -- I negotiated with him and believe me, he was absolutely relentless. He got there by living and breathing some fundamental, universal business truths. So in Steve's honour and in his memory, here are five of the cold, hard business lessons that we can all learn him.

Never Lose Sight of the Value of a Dollar

As successful as he was, Steve never lost sight of the value of a dollar. I learned this first-hand when I was running The Learning Company, which at that time was the global leader in educational software. Steve wanted to launch Macs in schools using our software. Apple only had a small share of the market and it cost us over $50 million to develop the software he wanted. There was no way we would create the software on our own dime.

We thought we could share that cost with Apple, since Apple would benefit from having our titles. But did Steve budge? Not a chance. He stubbornly refused to give me a cent and insulted me for daring to ask for his money. He was so adamant about watching his company's cash that he kept yelling profanities, even in the parking lot as I was getting into my car to leave. Money, after all, is the result of hours of painstakingly difficult effort. Giving it away should never be easy -- and for Steve, it never was. (That being said, I have always said that Apple should pay dividends -- but that's for another day.)

Work Hard

It's easy to say, but so few people really know how to work hard. For Steve, there was no substitute for hard work. He took his business seriously, because to him, Apple was everything. Stories abound of how Steve worked all hours when necessary -- weekends, evenings, you name it. That's because Steve knew that life isn't easy, and that to be successful, you need a lot more than a good idea. You need to make big sacrifices, avoid distractions, and be as ruthless as necessary.

Steve made sure that others worked hard, too. Even after engineers thought a product was ready to ship, Steve was known for spending countless hours agonizing over every detail. He would send his staff back to the drawing board over and over again, as many times as it took, until everything was perfect. Do you think his staff always appreciated his thoroughness? Of course not. But Steve knew that sometimes, great leadership is about pushing people to work harder than they knew they could.

Business Is Not a Popularity Contest

Steve Jobs had his critics. Some saw him as an egomaniac, and others, as a control freak. He would remember who on his team added value and who didn't. And he never apologized for his relentless, visionary drive -- because he understood that business is about making money, not making friends. Like every CEO should, Steve kept a laser-like focus on creating value for his shareholders.

Don't Wait to Acknowledge Failure

I have met many entrepreneurs who have the passion and even the work ethic to succeed -- but who are so obsessed with an idea that they don't see its obvious flaws. Think about that. If you can't even acknowledge your failures, how can you cut the rope and move on?

Steve never had this problem. When a product or an idea failed, he wouldn't obsess over it -- he would calmly take it behind the barn and quickly put it out of its misery. Anyone remember the Newton? How about the Apple Pippin? How about the QuickTake? With these and many other barely-remembered flops, Steve understood the importance of acknowledging a failure and quickly moving on.

Listen to the Market

Business is fundamentally about creating things that people want. But to do that, you have to know your customers inside and out. Do they want simplicity? Lower pricing? A better experience? More convenience? The answer is different for every business, but every business has to know the right answer for itself.

In the tech world, no company knew their customers as well as Apple under Steve's leadership. Steve and his team knew that a lot of people wanted their digital experiences to be easier, friendlier, simpler, and less intimidating. That's why they had the discipline to say no to thousands of perfectly good ideas, and instead to build products with fewer buttons, less complexity -- and much higher profit margins.

Final Thoughts

One thing I've always loved about money is that it's one of the only things in life that's black and white: you either make it or you lose it. Steve Jobs didn't just make it -- he created hundreds of billions of dollars in value for his investors, and even more for Apple's resellers, suppliers, developers and employees. As we remember Steve, let's be sure to learn the lessons of his entrepreneurial legacy.

Kevin O'Leary is a repeat entrepreneur, chairman of O'Leary Funds, and the bestselling author of Cold Hard Truth.

He appears on ABC's Shark Tank, CBC's Dragons' Den and CBC's Lang & O'Leary Exchange.

You can follow Kevin on Twitter (@kevinolearytv), on Facebook ( or at