Ep170: Thinking What You Think, Liking What You Like cover art

Ep170: Thinking What You Think, Liking What You Like

Ep170: Thinking What You Think, Liking What You Like

Listen for free

View show details

About this listen

 In this episode of Welcome to Cloudlandia, Dean and Dan open with a candid reflection on how the spread of AI is making authentic human presence feel more valuable, not less. From the small signal of Dean wearing an analog watch and missing the daylight savings change, to Dan observing the quiet shift happening in his own sense of discretion about how he spends his time, the conversation quickly finds its footing. They discuss how AI has democratized capability while leaving vision as the truly scarce resource, and why keeping a human in the loop between yourself and the technology may be the smartest positioning for entrepreneurs right now. The conversation moves through a rich detour on the making of Casablanca, a film nobody wanted to make, staffed by a rotating cast of writers and second-choice actors, that became an all-time classic through trial and error. This leads Dan and Dean into a broader discussion about Rick Rubin’s approach to music production: knowing what you like and being decisive about it, without needing technical ability. Dan connects this back to Strategic Coach and the idea that his thinking tools have always been an expression of thinking about his own thinking. His upcoming quarterly book, Who We’re Looking For, promises to capture exactly that kind of self-aware entrepreneurial identity. Dean closes with a sharp framework for evaluating the past: the distinction between “could have,” “would have,” and “should have”, and why only one of those carries real emotional charge. He ties it back to their running thread on guessing and betting, suggesting that the people who will win in the next decade are those who can look forward with clarity about what they are uniquely suited to do. This episode is a good one for any entrepreneur who wants to think more clearly about where their real advantage lies. SHOW HIGHLIGHTS As AI democratizes capability, vision becomes the scarce resource — and knowing what you want is worth more than knowing how to do it.Dan’s rule for technology and teamwork: only engage if it makes you better at what you’re already uniquely good at.Casablanca became a masterpiece by accident, rotating writers, second-choice actors, and a studio that just needed a film for Tuesday.Rick Rubin has produced some of the most celebrated music in history without being able to play an instrument, his edge is knowing what he likes and being decisive.Dean’s framework for evaluating past decisions: “could have” acknowledges options, “would have” shifts blame outward, and “should have” is the only one with real emotional weight.The next decade belongs to people who think what they think, like what they like, and do what they do best, because those are the bets most likely to pay off. Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT (AI transcript provided as supporting material and may contain errors) Dean Jackson: Welcome to Cloudlandia. Mr. Sullivan. Dan Sullivan: I'm here. I'm here. Dean Jackson: Okay. There You go Dan Sullivan: I can get about 10, 15 seconds of you preparing to focus on the next hour. Dean Jackson: You can? Okay. Dan Sullivan: Yeah. Yeah. I can hear packages crumbling. I can hear ... Dean Jackson: Things are getting in order here, moving Dean Jackson: Yeah. Dan Sullivan: Little bit of backstage before we get the front stage. I think that adds authenticity to the podcast. Flavor. Flavor. So Dean Jackson: They know it's real. Dan Sullivan: It's Dean Jackson: Not AI Dan and AI Dean talking. Dan Sullivan: So here's a question for you. Do you notice yourself becoming more human the more AI becomes pervasive? Dean Jackson: Yeah. It's the way. Dan Sullivan: In other words, real lationship. Dean Jackson: Yes. I think you're absolutely right.That's what I'm really noticing. It was a very interesting thing. This morning I went over to the cafe. I have to leave a little earlier because at 11, we do our podcast, but what had happened was I put a watch on today that I is an analog watch. Dan Sullivan: So it didn't account for the time change. Dean Jackson: Daylight savings. Exactly. Dan Sullivan: Yeah. Dean Jackson: And then I got in my car and I realized, oh my goodness. I haven't accounted for the time. That's funny. Dan Sullivan: Yeah, you're- Dean Jackson: How would we know, right? Our bodies don't know. It's so ... Dan Sullivan: Yeah. Well, I noticed coming to Chicago, so I'm in Chicago today. And I really noticed the impact of daylight savings time because Chicago is right at the beginning, the new time zone. I mean, the time zone I'm in all the way for Chicago and Dallas are in the same time zone. Yeah. But Dallas would be very, very late in the time zone. Chicago's very early. So I noticed it. I don't notice it that much in Toronto because Toronto is more in the second half of the Eastern time zone. And so I don't notice the difference, but I was really struck. There's ...
No reviews yet