“Predictions are actually a shitty business because ... if you make a prediction that ends up being correct, in between the time you make the prediction and it coming true, it becomes less provocative, less interesting, less bold.”

Our next question comes from Blister on Reddit. They say: Hi, Scott. You regularly display a high level of convention on outcomes that are highly uncertain. Young Americans wrong frequently, but that doesn't seem to faze you. It's a quality that a lot of very successful people possess, but I expect it's a product of success, or at least exacerbated by it, rather than an innate quality of successful people. I'd be curious to hear you reflect on that and how your confidence conviction has evolved throughout your life. I'm not sure if you're saying I'm confident or full of shit. I think the answer is probably both. I've been in the predictions business for a long time. So, my first, my only real job was in Morgan Stanley, where you were trying to predict the direction of bonds or fixed income or stocks. So, you would do your homework and then you'd have a viewpoint. I used to draft reports for analysts saying this is what so-and-so economists thinks is going to happen interest rates. So, the alpha or the juice, if you will, is in predicting the uncertain because, all right, if I turn this light on, if I flip the switch, most likely the lights will go on. No one's going to pay you to tell them that. They're going to pay you to give you an informed position. And the thing about predictions is it's not being right that matters, it's catalyzing an interesting conversation that results in better outcomes. Okay, I believe that a third of Levi's sales will be done online by 2010. I was wrong. I made that prediction in 2000. Levi Strauss and Company was my biggest client. I was in the strategy firm for 20 years. You're in the business of trying to create or fashion a future, and your job isn't really to predict the exact future, it's to create a series of possible scenarios such that you can plan against that future with strategy and resource allocation, the best foots to a number of different outcomes. So, I don't make predictions haphazardly. I read a lot, I look at a lot of data, and when I make a prediction, I actually believe it's going to happen. And again, the objective isn't to be right, but to catalyze a conversation that results in better outcomes. The key is to be right more than wrong. And occasionally, what's really exciting is you see something someone else doesn't, and you say, This is what I think is going on, and this is what I think is going to happen. And you get more right than you get credit for. Predictions are actually a shitty business because the judgment body of people, if you make a prediction that ends up being correct, in between the time you make the prediction and it coming true, it becomes less provocative, less interesting, less bold, right? I predicted Amazon would buy Whole Foods. Before they purchased Whole Foods, that seemed incredibly provocative and even crazy. They had never made an acquisition of that size, much less a grocer. But soon after they made the acquisition, it seemed obvious. It seemed rational. It didn't seem that provocative or risky to predict. I predict WeWork would not go public, that after reading the S1, that investors would gag on this ridiculous ayahuasca trip form of a prospectus. When I said that, when the prospectus came out, the entire media world lit up about me saying that. After the IPO was pulled, it was, well, of course it was pulled. It was obvious now in retrospect. In terms of what started that, what I would suggest is looking at data and then trying to draw a throughput line through the data and what happens. Where it gets really interesting in the predictions I really enjoy is I don't think people take into account that the people making these decisions are human. And most of them are huge ego midlife crisis men who I relate to and I can put myself, I can put my feet in their shoes. And oftentimes my predictions are not only based on macro data and social trends, but how I think a 58-year-old CEO might be thinking about this issue. Anyways, I love making predictions. I think it's important. At the end of the day, the way I kind of vote with my pocketbook is I invest in a lot of the predictions I make. Some I get wrong, some I get right, but here's the key: you just need to get more right than wrong. Also, what's changed as I've gotten older is I realize that as my platform has grown, I have a greater responsibility to do more work on predictions that might upset people or change policy. I said something about San Francisco last week, and the mayor actually called me. I realized that I've got to be, and while I still believe what I said, I've got to be, I don't know, just a little bit more thoughtful, careful. That's good and bad as my platform has grown. Thanks for the question. We'll be right back after a quick break. Support for the show comes from PipeDrive. 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