Amazon (AMZN -1.48%) shocked the business world last month with the announcement that Jeff Bezos would retire from the role of CEO. The company has long been a model for anti-fragility, or the ability to thrive in the face of challenges or grow through chaos, a concept developed by Nassim Taleb in his book Antifragile: Things That Gain From Disorder. With the upcoming departure of Bezos, investors are no doubt wondering what lies ahead.

On this clip from Motley Fool Live, recorded on Feb. 3, "The Wrap" host Jason Hall and contributor Brian Stoffel discuss the company's antifragile history and Bezos' lasting impact on Amazon.

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Jason Hall: How does Bezos' plan to step down as CEO change your view of Amazon going forward?

Brian Stoffel: One thing that I've learned, and Amazon's my number three position overall. If I never would've sold any and I have before just because it's got too big, it's definitely my biggest. If anything I've learned that I shouldn't overreact when something like this happens, especially when it's planned and there's a very clear glide path from one to the other.

I think when Steve Jobs passed away, that was so shocking. But just looking at what happened at Apple over the last 10 years, I was someone who really felt like innovation was dead, and I'm not totally certain that I'm wrong about that, and still it's been a great stock to own.

The thing that I'm looking for the most is, I have spent a lot of time digging through so many letters to shareholders from Jeff Bezos, and I've put it in the chat if anybody wants to read, I did one [article] a while back. I went through every single one for the last 20 years and if anything, anyone who watches this knows that I'm big on anti-fragility which basically means getting stronger from chaos.

There is no company that has done this better over the last 20 years than Amazon, and if you go back and you read those letters. To me, Nassim Taleb is the one who came up with the idea, at least popularized because he wrote a book called Antifragile. Jeff Bezos, they share the same DNA when it comes to that stuff and it's funny because there was a time when I mentioned that on Twitter and Taleb said, "I think he follows a lot of this stuff." He responded and said that.

I'm really curious to read the letter to shareholders, which I know sounds like such a small thing, but there is so much good stuff in there. The biggest one, and I'll just say this real quick and then I'll pass it on. There's a letter he wrote once about the difference between "two-way doors and one-way doors." A two-way door is the decision that you make, that you can make it, realize it didn't go so well and you can go right back through the door. It's just like at a restaurant where the wait staff goes back and forth, that's a two-way door. You should make those decisions superfast and that's so applicable to the way that we do our lives in non-financial ways too.

But he said that there are also one-way doors. Those are the doors that once you go through, it's going to be really hard to go back, and you should take forever to make those decisions. That if you understand anti-fragility, is part of the basis of anti-fragility. Marriage would be a great example. Obviously, you can go both ways, but it's not a two-way swinging door. It's really painful and hard, or at least it can be to go back through.

I'm curious to see if that essence can stay there, and maybe I'm naive in thinking that it's been there all along, but I have very little to say that it hasn't been and that's something I'm going to keep watching.