I’ve almost finished listening to Nassim Nicholas Taleb’s The Black Swan, a book about how large-impact, hard-to-predict, and rare event beyond the realm of normal expectations. At the same time, Tim O’Reilly caused me to stumble upon this article previewing Jim Collins‘ (author of Good to Great and Built to Last) new book “How the Mighty Fall.”

In some way the two authors’ could not be more different. Taleb writes in a harsh, sarcastic, cutting tone that heaps scorn on many of the worlds finest minds as well as, one senses, the books readers. His harshest barbs are reserved for academics, who if often sees as being to interested in theory to help with real world problems. I’ve never seen Taleb in person or on video, but after listening to The Black Swan I can’t help but see him as an lethal and angry intellectual street fighter, mad at a world that didn’t notice his brilliance earlier.

Collins, in contrast, reads like a classic business academic writer who has gone mainstream. He never offends, and his tone is never harsh – he seems like the archtype westcoast Business school Professor – smart, driven and direct, but slightly geeky in that friendly way and not overly intense (hence westcoast).

But while their styles (and I hypothesize, personalities) are dramatically different, they overlap in some curious and interesting ways. Both are concerned with business issues and both are writing about outliers. Taleb is concerned with the outlying events that can completely alter one’s world. Collins in concerned with outlier companies – those that experience impressive and continuous success. And while I’m sure there are lots of areas where the two will disagree, it is interesting to focus on where the two almost completely overlap.

The first appears where Collins talks about the first symptom of a company going into decline: Hubris Born of Success:

“The best leaders we’ve studied never presume they’ve reached ultimate understanding of all the factors that brought them success. For one thing, they retain a somewhat irrational fear that perhaps their success stems in large part from fortuitous circumstance. Suppose you discount your own success (“We might have been just really lucky/were in the right place at the right time/have been living off momentum/have been operating without serious competition”) and thereby worry incessantly about how to make yourself stronger and better-positioned for the day your good luck runs out. What’s the downside if you’re wrong? Minimal: If you’re wrong, you’ll just be that much stronger by virtue of your disciplined approach. But suppose instead you succumb to hubris and attribute success to your own superior qualities (“We deserve success because we’re so good/so smart/so innovative/so amazing”). What’s the downside if you’re wrong? Significant. You just might find yourself surprised and unprepared when you wake up to discover your vulnerabilities too late.”

This whole paragraph sounds like a friendly version of Taleb. Praising leaders who don’t claim to understand the full complexity of their world, their business or even their own success? Classic Taleb.

More interesting however, is the emphasis on luck. Taleb regularly argues that luck is (at a minimum) underestimated and more often ignored outright, as a factor in a businesses success. No CEO wants to stand up and say, yes, we become $10B dollar company not just because we were good, but because we were lucky – it doesn’t exactly send a positive message to share holders (or does it justify their enormous bonus). But Collins not only agrees that luck is a factor, he argues that good companies admit to themselves that luck was a factor.

In hockey you hear people say you’ve got to be good to be lucky and lucky to be good. The point is, if you work hard, bounces will eventually come your way and you’ve got to be good enough to pounce on them and make those opportunities count. Begin to think you don’t need luck, you stop seeing the opportunities and also begin to believe you are inherently better than anyone. Fact is, you’re not. You’ve got to work. Hard. And hope for some luck. Even then, you probably never become Google.

The second interesting place of overlap is in Collins discussion about how companies begin to deny that they are at risk or in peril.

“Bill Gore, founder of W.L. Gore & Associates, articulated a helpful concept for decision-making and risk-taking, what he called the “waterline” principle. Think of being on a ship, and imagine that any decision gone bad will blow a hole in the side of the ship. If you blow a hole above the waterline (where the ship won’t take on water and possibly sink), you can patch the hole, learn from the experience, and sail on. But if you blow a hole below the waterline, you can find yourself facing gushers of water pouring in, pulling you toward the ocean floor. And if it’s a big enough hole, you might go down really fast, just like some of the financial firm catastrophes of 2008. To be clear, great enterprises do make big bets, but they avoid big bets that could blow holes below the waterline.”

In The Black Swan, Taleb has an entire piece on assessing risk which parallels this quote. He notes that too often business people and – in particular – financial types, focus on predicting the likelihood of an event – even when a prediction model is deeply flawed or essentially meaningless. Since often assessing the likelihood of an event is often impossible Taleb argues it becomes much more important to ascertain the likely magnitude of it’s impact. So avoid doing things or exposing yourself to risks that, if they go wrong, will blow out your hull. Indeed, the Black Swan is essentially a 250 page book on this paragraph.