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Welcome to Cloudlandia

Welcome to Cloudlandia

By: Dean Jackson and Dan Sullivan
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 Join Dean Jackson and Dan Sullivan as they talk about growing your business and living you best life in Cloudlandia.© 2026 Welcome to Cloudlandia
Episodes
  • Ep170: Thinking What You Think, Liking What You Like

    Ep170: Thinking What You Think, Liking What You Like
    Apr 1 2026
    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 ...
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    54 mins
  • Ep169: Arguing With Time

    Ep169: Arguing With Time
    Mar 25 2026
    Every conversation has the potential to reveal something useful hidden within the ordinary, and this one delivers several of those moments. In this episode of Welcome to Cloudlandia, we catch up after Dan's 11th trip to Buenos Aires for his ongoing stem cell treatments, where he shares a remarkable milestone: a 12% increase in brain volume over three years, roughly equivalent to reversing 30 years of cognitive decline. The conversation flows naturally into Dean's growing practice of "phone fasting" and constraining his available hours, and how that's led to a heightened clarity about where attention actually goes each day. We then dig into the idea of "creating a better past", the practice of making today worth remembering tomorrow, and how this connects to calendar structure, scheduling disciplines, and the real cost of vague future planning. Dan shares why he treats his schedule as a commitment rather than a suggestion, and why words like "should," "would," and "could" are blame-shifting words that quietly block learning and behavior change. Dean's shift to locking in six months of workshops in advance gives a concrete example of how structure actually creates freedom. The episode closes on a thought worth sitting with: Dan's observation that at the bottom of all unhappiness, there's an argument with time. The conversation between these two has a way of making the abstract feel immediately actionable, worth your full attention. SHOW HIGHLIGHTS Dan increased his brain volume by 12% in three years through stem cell treatments, equivalent to reversing roughly 30 years of cognitive decline.Only 0.05% of people are proactively using AI to create output, meaning the competitive advantage window for early adopters remains wide open.Strategic Coach's 250 thinking tools stay permanently "upstream" from AI, because AI can only work with what humans have already created and published.Dan eliminated "should," "would," and "could" from his vocabulary entirely, calling them blame-shifting words that signal complaint without any intention to change behavior.Dean locked in six full months of workshops in advance for the first time, discovering that visible structure on the calendar creates bookings, and momentum that vague future planning never could.Dan's rule for unhappiness: at the bottom of every persistent dissatisfaction, you'll find someone having an unwinnable argument with time. Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT (AI transcript provided as supporting material and may contain errors) Dean: Welcome to Claudelandia. Mr. Sullivan. There he is. Are you in Argentina? Dan: Nope, nope. Dean: No, I'm Dan: Back in Toronto. No, we arrived about noon yesterday. We got back. Yeah. Dean: Okay. Joe is on his way. Dan: Yep. Yep. He left last night. Dean: Well, he didn't leave last night actually. Well, he missed his connection. So that's a problem. Yeah, hopefully he figured it out, but he was definitely on the ... We're not happy till you're not happy airline experience program. Dan: Yeah. Dean: So Garnet and Shirley, they were on the flight that took off. He was so frustrated. Yeah, he was so frustrated because he was on the runway or on the ramp and they were just taken off, so he missed just barely. Dan: You know, people are not necessarily talk about Joe, but I noticed a lot of people are throughout their entire life, they're about three hours late. Dean: Oh, just missed. Yeah, exactly. Dan: Yeah. Yeah. And if they just take one future event or one present event out of their life, they'd be on time, but there's always one thing that makes them three hours late. Dean: That's funny. Dan: Yeah. Dean: So you're in Toronto now? Dan: Yeah, just got back. Yeah. Yeah. Dean: Perfect. Dan: And the snow is starting to melt. Dean: Okay. That's what I hear. Dan: That's Dean: What I hear. You can see the light at the end of the tunnel. Dan: Yeah. Yeah. The power went out in our neighborhood last night. Suddenly it was just completely black, but at our house, five seconds later, the generator kicked in and we had full lights, electricity. Everything was working. Dean: Oh, see? Dan: Yeah. Dean: That's why you get a generator, right? Dan: Yep. Yep. Yep. Yep. Yep. Dean: Because that's like doing an experience transformer in advance. Dan: Yeah. Dean: Looking forward. Dan: I remember a New Yorker cartoon a long time ago, 30, 35 years. And it shows this elderly couple standing at a corner in New York City, a street corner. And right in the middle of the intersection is a dead elephant. Dean: Oh my. Dan: And the wife, the older lady is saying to her husband, "Elmer, I'm never going to complain about you bringing that elephant gun with you on a date." Dean: Oh my goodness. That's so funny. Better, safe than sorry. Dan: You never know when the elephant's going to show up. Dean: That's exactly right. Better to have the gun and not need it. Oh Dan: Yeah. Yeah. Yeah. It ...
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    1 hr and 4 mins
  • Ep168: Why Relationships Still Beat Algorithms

    Ep168: Why Relationships Still Beat Algorithms
    Mar 18 2026
    AI is producing more content than ever, but the competition for real human attention has never been fiercer, and no algorithm is going to change that. In this episode of Welcome to Cloudlandia, we open with Dean noticing a new kind of AI fatigue, the creeping discomfort of scrolling through feeds filled with emotionally manipulative, AI-generated content designed to mimic reality. Dan adds his own observation: the UN’s push to centrally control AI development, which he sees as less a threat and more an unintentional comedy. From there, the conversation gets into the economics of attention, Dean’s framing of 1,000 waking minutes per person per day as a fixed resource, and Dan’s eight years of recovered attention after cutting television (roughly 800 hours a year, or 100 full days). We then work through the distinction between capability and ability, why giving everyone access to the same tools doesn’t level the playing field, any more than putting a grand piano in every home produces Billy Joel. Dan shares a striking data point from Strategic Coach: after 36 years in business, 85% of their 800 registrations last year still came through personal referral, no technology involved. That leads Dean to a new concept he’s developing called “REAL-ationships,” the coming premium on trust built with actual people as AI-generated mimicry becomes harder to distinguish from the real thing. Dan caps it with a sharp observation: technological mimicry is not emotionally satisfying, at least not after the first time. This episode lands on a counterintuitive truth for any business owner: the more powerful AI gets at producing content at scale, the more valuable a genuine human relationship becomes. It's worth a listen. SHOW HIGHLIGHTS Dean identifies a new kind of AI fatigue—not from using it, but from being unable to escape emotionally manipulative AI-generated content in everyday feeds.Dan recovered 800 hours of attention per year—equivalent to 100 full days—simply by cutting television eight years ago.Everyone has 1,000 waking minutes per day; with roughly 450 already consumed by screen time, the real scarcity isn’t content—it’s attention.Capability vs. ability: giving everyone a grand piano doesn’t produce Elton John—the qualitative edge still belongs to the person, not the tool.After 36 years in business, 85% of Strategic Coach’s 800 annual registrations still come from personal referral—no technology involved.Dean’s new concept “REAL-ationships”: as AI mimicry becomes undetectable, the value of trust built with a real person you know is only going to increase. 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: Mr. Jackson. Welcome to Cloudlandia Dan Sullivan: Yes. Welcome to Cloudlandia. Dean Jackson: So you know what's funny? Dan Sullivan: Is it getting congested? Dean Jackson: Oh, I realized, I think I've noticed that today or this week, I reached a level of AI fatigue that I'm noticing is a different sensation in that- Dan Sullivan: It's like the 18 mile mark of the marathon. Dean Jackson: I think that's true. I'll tell you what happened for me is that when I watch Reels or Instagram or Facebook, any of the things, what I'm noticing is the majority of the things that I'm seeing now are AI. And it's getting to where it's not as obvious that it's AI, but it is AI and you can tell that it's AI and it kind of is getting to where it's bothersome. And I realize that this is like we're seeing things, especially when they're trying to make things, they're using it now to create videos that tug on your heartstrings in a way like this family adopted this lion mother who laid her ... They fed the lion and now the lion brings back her cubs to meet the homeowners. And it's just so ridiculous. And everybody is ... Dan Sullivan: Yeah. And this is in Monica Beach, right? Yeah, exactly. It's near the Ferris wheel on Monica. Yeah. Dean Jackson: Santa Monica here. Right. Exactly. Santa Dan Sullivan: Monica. Santa Monica. Yeah. Dean Jackson: It's Just so ... So I realize now, and the fact is that most people don't realize it. I mean, there's so much engagement and you start to see now how just all of these situations where people are being confronted or having arguments or what looks like ... This is where it becomes troublesome is the propaganda ones where they're showing confrontations or arguments between two people. Angry Karen does this or confronts this person or all these things where it's like ... I don't know. It's like ... I always say how Jerry Spence talked about that our minds are putting out their psychic tentacles, testing everything for truth, and it can detect the thin clank of the counterfeit. And I think that that's true, but I worry that many people's counterfeit detectors are not...
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    1 hr and 5 mins
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