Robert Reed is a business columnist for the Chicago Tribune. He’s written on a broad range of topics from Net Neutrality to McDonald’s plastic cold drink cups, and he came to the table this week for a free-ranging conversation about the economy and Chicago’s business climate. We changed topics pretty often, so here are some highlights from our conversation.

On the historic digital disruption we’re all living through in retail, entertainment, medicine and just about everything else:

But the whole relationship is changing, so maybe you will go to a store and pick up something that you ordered online. We’re going to see that in retail, apparel, and appliances, and we’re also going to see it in groceries. That’s a real big area of change. And Amazon is driving all of this.

Big, big stuff, and you know it is across the board. It’s going to happen in medicine. It’s happening in education. You name it, whatever it is, whether it’s a for-profit industry, a non-for-profit industry, the changes that are rippling through are going to have to be dealt with. And what no one can really say right now is it for the greater good and what’s the greater good. Will people be employed? Will they be able to live where they want to live?

On Amazon’s HQ2. Chicago’s in the top five, he believes, and one of our weaknesses is a strength: We’ve got lots of places for people to live:

It would have a positive impact, but there would be riplets because of it. But frankly, that’s one of the reasons why I personally believe Chicago has a good shot at it, because when you look at the, what they call the request for proposal that Amazon put out, Chicago does size up pretty well. And one of the things that I think Amazon is concerned about is community backlash, because they are having problems in Seattle on this point and Mayor Rahm Emanuel I think is right. They don’t want to walk into that problem again, which they could in a lot of the markets they are looking at. Chicago could absorb them. There are what, eight to ten tracts of land that you could do something with. So I think from that perspective it has a shot.

Increasingly though, I think the political dysfunction of the State is going to get in the way, because nobody wants to parachute into the middle of some kind of brawl like that, and that could be a problem. And so when you look over that list of 20 I think Chicago has a shot. I think the Washington area has a shot, but I also wouldn’t rule out something out of the blue, you know.

More Amazon: It looks as thought Amazon is set to battle, and possibly forever change, Walgreens. Can Amazon kill Walgreens?

I don’t think it could do that. I think Walgreens will have to do something, maybe like CVS is acquiring Aetna and become more of a healthcare provider, but Walgreens seems to be more intent on staying within the retail pharmacy, cosmetics, that world. And you know it’s a highly regulated industry, and one of the things that Walgreens has been able to do is navigate that. Amazon less so. I mean when Amazon has tried to sell basically regulated products it has run into problems, like liquor and beer, so there’s a learning curve there.

When a company is perceived as old and not modern in its ways, is it curtains? We talk about Sears and McDonald’s, two historically Chicago-based giants.

I think both of them had sort of for a long time said, “We will tell the customer what they want, and we’re not going to listen to the customer.” And that changed, and in McDonald’s case they heard and they’ve gone through a number of wrenching changes to be more… You know you are still selling fast food, so the areas of nutrition and healthy diets and all that, that’s not going to go away. They still have to deal with those issues. In the case of Sears, they wanted to be everything to everyone. They told you what they were going to give you, and if you didn’t like it well there was something wrong with you. [Laughs]

On the digital and generational shift happening in virtually every industry and business:

And the difficulty as a worker is to recognize and go with the change and not resist it, while at the same time maintaining what I consider to be core values and keeping true to yourself, and not getting swept away by all of this innovation and losing your humanity or looking out for other people. It’s difficult to cope in this society.

You can listen to this show on SoundCloud here.

You can read the transcript of this show here:CN transcript Feb 1 2018