I’m starting a new feature that will run every Friday (well, that’s the plan anyway) and focus on one or two interesting pieces on risk.  I’ll flag news articles, speeches, commentaries and other content that offers a thoughtful perspective on risk – both purposeful risk-taking as well as risk mitigation.

This week, it seems appropriate to feature one of the greatest risk-takers of our time, Steve jobs, who just stepped down as CEO of Apple.  Compared to other CEOs, Jobs has had little to say over the years for a man with so many accomplishments, but his few speeches are gems.  Here (with a big hat tip to Brendon Slattery at Macworld) are three worth reading, with highlights on Jobs’s comments about risk.

The first is an interview Jobs gave to Playboy in 1985, just a few months after the Macintosh was introduced. Here is what he had to say then about risk-taking:

“At Apple, people are putting in 18-hour days. We attract a different type of person‑ a person who doesn’t want to wait five or ten years to have someone take a giant risk on him or her. Someone who really wants to get in a little over his head and make a little dent in the universe. We are aware that we are doing something significant. We’re here at the beginning of it and we’re able to shape how it goes. Everyone here has the sense that right now is one of those moments when we are influencing the future. Most of the time, we’re taking things. Neither you nor I made the clothes we wear; we don’t make the food or grow the foods we eat; we use a language that was developed by other people; we use another society’s mathematics. Very rarely do we get a chance to put something back into that pool. I think we have that opportunity now. And no, we don’t know where it will lead. We just know there’s something much bigger than any of us here.”

What’s remarkable now is how fresh the interview feels.  Its themes are still current; it reads as if Jobs could have given it yesterday.

The second selection is from remarks Jobs made about a dozen years later, in 1997, when he appeared at the annual Macworld convention and told the assembled faithful that Microsoft would invest in Apple to shore up Apple’s weak financial position.  Jobs addressed the rivalry with Microsoft that had long been a defining part of the Apple culture:

“If we want to move forward, see Apple healthy and prospering again, we have to let go a few things here. We have to let go of this notion that for Apple to win, Microsoft has to lose. We have to embrace the notion that for Apple to win, Apple has to do a really good job. And if others are going to help us, that’s great … And if we screw up and don’t do a good job, it’s not somebody else’s fault – it’s our fault … So the era of setting this up as a competition between Apple and Microsoft is over as far as I’m concerned. This is about getting Apple healthy, and this is about Apple being able to make incredibly great contributions to the industry, to get healthy and prosper again.”

This is pretty amazing when you consider that Jobs’s disdain for Microsoft burned hotter than anyone’s.  Yet Microsoft’s lifeline was vital to Apple’s survival at the time, and Jobs was able to see what was really important and set aside his animosity.  But it wasn’t just expediency that motivated Jobs to embrace a rival in a moment of need.  He clearly wanted to shift the thinking at Apple and put the company in a position to be innovative, dynamic, a force in the industry and firmly in control of its own destiny.  It was a huge risk at the time but it opened the way for the company’s astonishing success in the years that followed.

Last, but hardly least, is Jobs’s 2005 commencement address at Stamford University.  It’s incredibly personal and moving.  Jobs speaks eloquently about risk-taking, creativity, rebounding from setbacks (like being fired as CEO of Apple) and finding – and doing – what you love.