Welcome to Cloudlandia

Protecting what you've built, revisiting where you started, and betting on the systems that have never let you down. In this episode of Welcome to Cloudlandia, Dan and Dean open with a riff on the strange new logic of secrecy in the internet age, where the best way to protect an idea may be to share it widely. Dan's story about a platform speaker who borrowed his Free Days, Focus Days, and Buffer Days framework without credit turns into a sharp point: the internet has made intellectual property both more fragile and more defensible at the same time. Dean connects this to his Nine Word Email and the way naming an idea is often the most durable form of ownership. Dean then pulls out journal number one, dated April 1996, thirty years ago this week, and the conversation becomes a time capsule. He walks through his early real estate licensing business, Toronto and Beyond, and how the same playbook he used then to generate leads in Halton Hills is still running today in Winter Haven, Florida. Dan reflects on his own 25-year journaling project that began after a difficult 1978, and shares that his massage therapist of 34 years recently confirmed his physical condition hasn't changed since they started. The episode closes on a larger canvas: real estate as a measure of civilization, the Louisiana Purchase at 50 cents an acre, Canadian politics, AI-driven job creation, and the quiet argument that the best protection against an uncertain future is a system that has already worked across three decades. SHOW HIGHLIGHTS 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: Yes. And AI will know about this call. Probably never. Dean Jackson: Probably Dan Sullivan: Never. It'll be scandalized. It'll be confused. Dean Jackson: Yes. This is the closest to analog. It's like, how did those spies meet in the trip down to our bathing suits neck deep in the ocean, having no wires, nobody listening. That's what Dan Sullivan: We're Dean Jackson: Having right now. Dan Sullivan: Yeah. There's a great story about Reagan, President Reagan. And when he got in, there was a particular situation where it was very clear that the Russians, the Soviets at that time, Dean Jackson: Were Dan Sullivan: Stealing American secrets. Dean Jackson: Very sneaky. Dan Sullivan: And Reagan had an interesting response to it. He said, "You know what we ought to do? Every so often, maybe every six months, we should collect every single secret in the United States and put them in 747s, cargo planes, 747 cargo planes, and fly them all to Moscow and dump them on the runway and fly off. And every six months we just dump all our secrets on the runway." He said, "The sheer confusion that that will cause will destroy the Soviet Union in a matter of a couple of years." Dean Jackson: That's funny, isn't it? Yeah. There's something interesting. Yeah. It's so funny, right? The things that we want to keep secret seem to be more desirable than the things we're willing to share. It's so- Dan Sullivan: Yeah. Just share everything. The way to destroy them. Actually, Seth Godin had a great line. He said, "Before the internet, the way to keep a secret secret was to keep it secret." Dean Jackson: Yes. Dan Sullivan: He says, "The way after the internet to protect your secrets is tell everybody your secret." Dean Jackson: Yeah. Oh, Dan, I can't tell you. So how many times the ... I created this thing called the nine word email. And the best thing I did was name it. And it's become known everywhere. And everybody who tries to present that idea as an original or as a, "Hey, here's this thing I've been working on. " Every single time in the comments is, "Oh, that's Dean Jackson's idea or that. " But predominantly, most people start out with the, "Here's an idea I learned...

The most productive stretch of your life probably isn’t waiting for motivation, it’s waiting for the right constraint. In this episode of Welcome to Cloudlandia, we follow Dean’s hundred-day phone fasting experiment locking his phone away from 10 AM to noon and what it revealed about the power of inevitability. Dean calls this his most consistently productive stretch ever, and Dan predicts that by the one-year mark, at least 20 other habits will have quietly shifted as a side effect. The big lesson: willpower is unnecessary when you design a system that removes the other options entirely. Dan shares that he’s now at day 116 of his ‘Creating Great Yesterdays’ practice and is finishing a new quarterly book, Yesterday Creates Tomorrow. He also makes a sharp case for proactive health investment twice-yearly full bloodwork, AI-assisted cancer detection, and taking personal ownership of your body rather than waiting for the system to catch something at stage four. The conversation moves into the language of regret, where Dan breaks down why ‘should,’ ‘would,’ and ‘could’ are manipulation words and how reframing your past experience as a source of lessons removes its power over you. The episode closes with a great business story from a Free Zone client: while every gas station in Washington State started charging for bathroom access, he went the other way, free bathrooms for everyone and created lineups of grateful customers who paid double out of sheer relief. It’s the kind of counterintuitive move that’s easy to describe and hard to execute, which is what makes it worth hearing about. This one’s got a few moments you’ll want to replay. SHOW HIGHLIGHTS 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: Good morning. Dean Jackson: Welcome to Cloudlandia. Dan Sullivan: Yes. I'm feeling it. I'm feeling the impact of Cloudlandia. Dean Jackson: I love that. There's always a home for us here in Cloudlanvia. Dan Sullivan: Yes. It's Dean Jackson: Our third Dan Sullivan: Space. Yeah. Well, yeah. And it's custom designed. Dean Jackson: That's exactly right. Dan Sullivan: It's custom design. Dean Jackson: You know when I say that, that's a really interesting thing, our third place, because that's how Starbucks, that was the intention of Starbucks when they got started as a third place between work and home, somewhere where you go to meet people and have great conversation. It's so funny because they've completely moved away from that. Now with the drive-throughs and the ... I described the interior spaces of the new coffee places as prison cafeteria style. It's like get your stuff and move along. Don't see them. Dan Sullivan: Yeah. Well, they went through a period, I think it's trying to think about a 10-year period where they were preaching to you, trying to make you a better person. And that didn't work. Don't have a goal in selling any product of transforming human nature. It's one of my- Observable. It's one of my firm foundational stones. Humans are going to do what humans are going to do and don't try to create a better human being. Just give them a little caffeine jolt and some sugar and they're okay. Dean Jackson: Observable life lessons. That's Dan Sullivan: Exactly right. Yeah. Yeah. Yeah. Dean Jackson: It's so funny. Dan Sullivan: Yeah. I think that's really the big thing now because this was actually ... I read an interesting book and it's called The Progressive Era in American History. And it starts kind of, I would say probably right after the Civil War. And it was a middle class. It was like people who lived in nice neighborhoods and they had nice things. And they made it their goal that their responsibility in life was to look at anywhere in America that didn't look like their neighborhood, didn't...

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 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...

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 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...

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 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...

The entrepreneurs quietly mastering AI right now won't make headlines, they'll just quietly take market share. In this episode of Welcome to Cloudlandia, we trace how birth timing, access, and circumstance shape who becomes an outlier from Malcolm Gladwell's hockey birthday effect to how Bill Gates got his 10,000 hours on a mainframe. Dan connects those dots to today's college graduates, whose degrees have been quietly devalued as AI handles both entry-level tasks and executive scheduling. The generation that sidesteps that broken system and goes straight to mastering AI, Dan argues, is the Andre Agassi of our moment, getting an unfair head start while everyone else is still in line. We shift into the mechanics of entrepreneurial success, where Dan introduces a new Free Zone tool: separating intentional wins from accidental ones. Some of your biggest breakthroughs, like Dean switching from professional tennis to real estate after watching a 15-year-old Andre Agassi dismantle a field, weren't planned, they were recognized in the moment. Dan also shares Day 75 of his 'Creating Great Yesterdays' practice, and how reframing ADD as emotional commitment to too many future possibilities at once finally gave him a way to work with it rather than against it. What ties this conversation together is a quiet argument for building inevitability into your environment. Whether it's locking your phone in a box, structuring a Free Zone summit around a single tool, or recognizing when the game you're in no longer matches who you're becoming, the clearest wins come from making the right behavior the only option. This episode rewards multiple listens. SHOW HIGHLIGHTS Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT (AI transcript provided as supporting material and may contain errors) Dean: Welcome to Cloudlandia. Mr. Sullivan. Dan: Mr. Jackson. Quality training. Quality training. I guess- Dean: For quality Dan: Purposes. Dean: That's why Dan: Everything Dean: Is recorded, right? Dan: I guess we need more of that, don't we? Quality training. Yeah. Dean: So you made it back? Dan: Yeah. It was unbelievable how we got back. Everything was exactly on time. Dean: Oh my goodness. Dan: Yeah. I put that date in the calendar. Dean: So they've abandoned their, we're not happy till you're not happy policy. Dan: Yeah. And in San Diego, they have this brand new terminal, which for a while anyway, is just devoted to Air Canada and Southwest Airlines. Oh, goodness. Dean: Wow. Dan: Yeah. Yeah. It's beautiful. I mean, beautifully designed. Dean: This is in San Diego? They have an Air Canada terminal? Dan: No, it's a brand new terminal. And for now, the only airlines are Air Canada and Southwest Airlines. Dean: Oh, okay. And this is in Toronto? No, Dan: San Diego. Dean: Oh, in San Diego. Yeah, yeah. Okay. That's surprising that the ... Dan: Yeah, it opened about six months ago. Oh, Dean: I like that. Dan: It's an extension of the main terminal, but for now. And for a moment in history, I don't know how long, but you just arrive and you walk in and Air Canada is right there. That's great. Dean: They Dan: Take the bags and then you just go to the left a little. And the clear line is we have clearer. And we walked straight through. Bags went straight through and really nice, very nice terminal. But the gate where we needed to be was right there. And the plane arrived on time and we got on time. It took off on time. And we got home a half hour early. I guess the jet stream was more powerful that night. And Dean: Everything is working. That's almost like just a few more of those and not going to erase the taste of your other Dan: Experience. Oh no, that was gone and then that was gone. Oh, Dean: Good. There you go. Dan: That was gone. I don't really hold onto it. I've Dean: Always Dan: Loved the- But I had been playing with a...

The way you structure your time shapes everything else, including who else can reach you, and when. In this episode of Welcome to Cloudlandia, we get into two parallel time experiments that Dan and Dean are running, Dan's 70-day practice of using each day to "create a great yesterday," and Dean's intermittent phone fasting that divides the day into clear, protected zones. Dan traces the origin of his approach to a story from Leora Weinstein, who shifted his focus entirely from the uncertain future to building a reliable past, one day at a time. The result? His most productive December and January on record, and a measurable shift away from last-minute scrambling. They also explore how abundance, whether it's 14 kinds of corn flakes or an infinite choice of tasks, can paralyze decision-making rather than free it. The conversation moves through Dan's "Upping Your Game" tool (an evolution of the A/B/C model), AI bots taking on their creators' personalities, the surprising legal and real estate ripple effects of data centers, and a listener book recommendation about the history of money. Dan makes the case that the real cure for future anxiety isn't better planning, it's higher consciousness in the present. There's something almost game-like about committing to a better past each morning, and both Dan and Dean are finding that the scoreboard doesn't lie. This one's worth your time. SHOW HIGHLIGHTS Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT (AI transcript provided as supporting material and may contain errors) Dean Jackson: Welcome to Cloud Landia, Mr. Sullivan. Hello there. There he is. From the West Coast. Dan Sullivan: Yes, I am straight Dean Jackson: To Cloud Landia. Cloud Landia is accessible from all points. Dan Sullivan: Yes, yes. But where you're sending from does make a difference. So I had a question for you. Dean Jackson: Tell me Dan Sullivan: From your experience, because you've had both, what's worse, 23 degrees Fahrenheit in Orlando, or minus 10 degrees in Toronto? Dean Jackson: Well, I will tell you this, that it came to the point last week that I actually had to wear pants one day. And so yeah, there's that, which I don't prefer, but today is a beautiful, we're right back now up to, let's see, it's 71 and sunny, probably similar to what you have right this moment. Dan Sullivan: Yeah, we're probably there. Yeah, the door is open. I'm looking out at, it's a nice place. I don't know if you've ever been here. Which one? La Jolla. Estancia. Dean Jackson: Yes. I've been to Estancia. Yeah, it's very Dan Sullivan: Nice. Nice place. Yeah. Yeah. We gotten in here just about this time yesterday, just a casual afternoon. Went to a really nice place, Maxima, who was with you last week? Maxima. And we went to an old hotel called the Empress Hotel. Dean Jackson: I know where that is. Dan Sullivan: Really nice restaurant. Dean Jackson: Oh, that's great. Dan Sullivan: Yeah, it's good. Dean Jackson: So the crowd is gathering. Dan Sullivan: I don't know if any of the clients are in yet. Our team just came in. I was sitting in the lobby. Lobby. And so half our team. Yes, Dean Jackson: Please. When is the actual, so you are in La Jolla, California for the Free Zone Summit, and that is on Tuesday is the actual day? Dan Sullivan: Well, it really starts Dean Jackson: Monday night. Dan Sullivan: Well, it starts Monday afternoon because Mike Kix is going to put on an AI from three to five o'clock. And then, Dean Jackson: Oh, there you go. Dan Sullivan: Then the Pacific Dean Jackson: Starts right in his backyard. Dan Sullivan: Yeah. Pretty well. Pretty well. And he's going to use one of our tools for part of his presentation. We have, I don't know if you remember an old tool. It was called the A BC model, and the A represented activities that you find really irritating. You hate them. Dan Sullivan: Yes. Dan...

In this episode of Welcome to Cloudlandia, we explore how changing fundamental time structures unlocks behavioral transformation that willpower alone can never achieve. Dean shares his 14-hour phone fasting experiment and the profound impact of creating inevitable constraints rather than relying on self-discipline. We discuss how raising decisions to the level of inevitability—physically locking your phone away—removes the constant negotiation with temptation. Dan introduces his new framework for productivity: making your purpose each day to create a great yesterday, shifting focus from anxiety-inducing future planning to confidence-building past accomplishment. We examine how AI accusations on social media reveal our default skepticism, why technology adds to life rather than eliminating existing solutions, and the critical difference between content and context in an AI-saturated world. The conversation moves through airport infrastructure decay, New York's political experiment, and why surgeons will always be humans using technology rather than replaced by it. This is a conversation about reclaiming attention, restructuring time, and recognizing that confidence comes from documented wins rather than optimistic projections. Whether you're struggling with digital distraction or seeking sustainable productivity systems, this episode offers practical frameworks grounded in real experimentation. SHOW HIGHLIGHTS Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT (AI transcript provided as supporting material and may contain errors) Dean Jackson: Mr. Sullivan. Dan Sullivan: Yes, Mr. Jackson. I wonder if our calls are being recorded in China. I just wonder. I hope so. I hope so. And transcribed and transcribed. I'd like to see one of our transcriptions in Chinese idiograms. That's it. Exactly. So are you just- I would get it framed and put it on a wall. Dean Jackson: Oh, that's perfect. Are you just getting up or are you still up from the big party last night? Dan Sullivan: No, we had massage. We have a massage therapist that we've had since 1992. 1992. She comes to our house on Sundays. Yeah. Dean Jackson: Oh, that's fantastic. Dan Sullivan: Yeah. Yeah. Yeah. Well, that's great. Dean Jackson: So how was- Dan Sullivan: We don't have the ideal climate that you enjoy at the Four Seasons. Valhalla. Valhalla. But we try to make up for it with other dimensions. Dean Jackson: That's right. The little built-in spa. Dan Sullivan: Yeah. Dean Jackson: Well, that's fantastic. So the party was a big success? Dan Sullivan: That was great. Dean Jackson: Yeah. Yeah. Had Bob's birthday party. Dan Sullivan: Yeah, it was great. Yeah, we had a restaurant. We took it over for ... Restaurants will have private parties and you take over the whole restaurant. And it's right at Front and Bay Street, just almost across from Union Station. And it's Peruvian Japanese fusion. Just shows you what people are putting together these days. And it was great. It was great. And our entire involvement was just showing up. Dean Jackson: Yes. I love that. That's the best. Dan Sullivan: Yeah. And Mark Young and his son were there and David Haase and Lindsay came. And Pete Warrell was here. He came ... Yeah. Richard and Lisa. Richard and Lisa were there. And so a lot of people traveled quite a distance to get there. So it was really great. Yeah. Dean Jackson: Absolutely. Oh, that's awesome. Yeah. I was texting with Richard Rossi yesterday. Dan Sullivan: After 12:00. After 12 o'clock noon. Dean Jackson: That's exactly right. Dan, I am a converse. Dan Sullivan: You're a new man. You're a new man. You're a new man. Dean Jackson: I am. I mean, this is a new normal. It's such a ... I'm realizing what a difference this phone fasting is. It's the best thing that I've ever done for productivity and just the ... I don't know. It's like the brain chemistry. I can feel it...

In this episode of Welcome to Cloudlandia, Dean and Dan explore the rapid transformation happening at the intersection of AI, work, and human relationships. Dean shares insights from an AI marketing conference where attendees split into two camps—those excited by technical possibilities and those overwhelmed by the pace of change. The key insight? Focus on the "what" and "who" rather than getting lost in the "how," treating AI as a tool that handles the backstage work while humans shine in front-stage interactions. The conversation takes a sobering turn as they examine how AI is fundamentally reshaping employment markets. Entry-level jobs are vanishing as companies choose AI over inexperienced workers, and the educational system continues training students for positions that may no longer exist. Dan shares a fascinating study showing how teachers' cognitive profiles have shifted dramatically toward fact-finding and rule-following—exactly the skills AI now replicates—while entrepreneurial thinking remains uniquely human. They discuss the growing value of authenticity in an increasingly automated world, from the appeal of live podcasts to the irreplaceable nature of genuine human hospitality. Dan shares his successful framework for using strategic thinking in political campaigns, demonstrating how human connection and listening remain the foundation of influence. The episode concludes with a powerful observation: as AI attempts to take center stage, the real response will be a return to valuing live, in-person human experiences more than ever. SHOW HIGHLIGHTS 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. Hello there. There he is. How are you? Dan Sullivan: Good, good. Dean Jackson: There we go. Well, you are in Chicago now? Dan Sullivan: I'm in Chicago, yeah. Reasonably mild for this time of year. It's just a little bit above phrasing, still not too bad. Not too bad. Well, Dean Jackson: It's reasonably perfect here, just exactly at room temperature in the courtyard. Yeah. So there we go. You had a great week with the live 10 times talk podcast with Joe this week. That was good. Speaker 3: I think Dean Jackson: That there's a real pendulum swing right now in live, craving live and authentic and real stuff. It's a pretty interesting juxtaposition this week because I spoke at a conference on Monday and AI bought/marketing conference that Perry Belcher was holding in Orlando. So about 650 people there and it was just speaker after speaker sharing all the amazing things that are coming, that they're doing with generative AI and agentic AI, all the things. And we had a panel at the end of the day with all the speakers and I noticed two types of questions. It was open for Q&A. So people would come up to the mic and I noticed that there were technical people asking technical questions about the mechanics of how do you string together these syntax and using all this language of what the behind the scenes, the things that are making things happen. Dean Jackson: And then there were other people who came and were sort of like deer in headlights caught with feeling overwhelmed that they're in the wrong room, that they're so far behind, they'll never catch up. And it was really what struck me is it was, I said, the best thing if you're a creative person, a visionary in this, is the best thing you could really do is just pay attention to what they're doing, what's actually possible to get an idea of what the actual applications are and how you would see this working for you because that's what your strength is. And note who is doing these things and just focus on the what and the who and just completely bypass the how. Don't worry about how to do any of this. I said, this room is full of people who are ready and will do, which is...

In this episode of Welcome to Cloudlandia, Dan and Dean explore the intersection of personal transformation and rapid global change in our technology-driven world. Dean reveals the profound results of his eight-week phone-in-the-box experiment, sharing how reclaiming 14 hours daily has restored his ability to read for extended periods and revolutionized his creative process. He discusses developing systematic approaches to manage ADHD, including mastering 50-minute focus sessions that consistently produce two fully-formed thought pieces. With Charlotte, his AI partner who can read his handwriting, Dean has created a sustainable rhythm for generating hundreds of insights annually. Dan shares unexpected breakthroughs from his stem cell treatments—while the 50-year-old knee injury heals slowly, his cognitive testing has improved 90% and his reflexes have returned to levels he hasn't experienced in decades. He discusses upcoming book launches, including The Greater Game with John Bowen, featuring original entrepreneurial research and interactive dashboards, plus the innovative four-by-four casting tool being developed as their first licensed internet product. The conversation shifts to examining how individual action amplified by technology can expose truth at remarkable speed. From Venezuela's Maduro being extracted to a Brooklyn jail cell to a lone citizen journalist uncovering $112 million in daycare fraud with just his phone and one day of investigation, we explore how Cloudlandia enables rapid revelation of hidden realities. We close by reflecting on the philosophical nature of AI use—how billions of people are each creating entirely unique cognitive signatures with their AI tools, as distinctive as fingerprints yet largely invisible to the world. It's a fascinating look at how technology simultaneously democratizes capability while making individual creative processes more private than ever. SHOW HIGHLIGHTS 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. Dan Sullivan: Mr. Jackson. How are you? Good, good. Had a great trip to London for- Dean Jackson: I didn't know you were going to London. Dan Sullivan: Yeah. Yeah. We just decided at the last moment, unfortunately, we got good flights and good rooms and some friends of ours from the DC area, they went and Steven Palter and his family were there. Oh, Dean Jackson: Nice. Dan Sullivan: So lots of great meals, lots of great place. Two out of three, which is good batting average. That gets you into Hall of Fame if you get two out of three. Exactly. Actually, if you get three out of 10, you've got a good chance. Dean Jackson: That's right. Dan Sullivan: If you play 20 years and have a 300 batting average, probably you're in consideration depending on Dean Jackson: Venture capital. Dan Sullivan: When the hits actually happened. Dean Jackson: Yeah. I got Babs texted on New Year's Eve and you guys were back from ... I didn't realize you were gone. Were you there for Christmas or after Christmas you went? Dan Sullivan: Yeah, we left on Christmas day night and flew overnight to London. And then boy, it was buzzing. London downtown doesn't matter what day it is, it's buzzing. Yeah. I just saw a video last night and it's one of these new AI films, which I think is really great where they'll take a sketch that was made of London 2000 years ago and then they'll animate it. And Speaker 3: It's Dan Sullivan: Really terrific. It's really terrific. For history buffs, it's terrific. I think this AI thing has uses. What do you think? I mean, are you noticing things that you wish you could have done five years ago more quickly? They're happening more quickly. Dean Jackson: Yeah. I'm working today on creating a better past. And the better past involves AI. Yeah. That's a really interesting thing. I watched over Christmas,...

In this episode of Welcome to Cloudlandia, we explore how Miles Copeland, manager of The Police, turned Sting's unmarketable song "Desert Rose" into a 28-million-dollar advertising campaign without spending a dime. The story reveals a powerful principle most businesses miss—the difference between approaching companies at the purchasing department versus the receiving dock. Dan introduces his concept that successful entrepreneurs make two fundamental decisions: they're responsible for their own financial security, and they create value before expecting opportunity. This "receiving dock" mentality—showing up with completed value rather than asking for money upfront—changes everything about how business gets done. We also explore how AI is accelerating adaptation to change, using tariff policies as an unexpected example of how quickly markets and entire provinces can adjust when forced to. We discuss the future of pharmaceutical TV advertising, why Canada's interprovincial trade barriers fell in 60 days, and touch on everything from the benefits of mandatory service to Gavin Newsom's 2028 positioning. Throughout, Charlotte (my AI assistant) makes guest appearances, instantly answering our curiosities. SHOW HIGHLIGHTS Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT(AI transcript provided as supporting material and may contain errors) Dean Jackson: Mr. Sullivan, Dan Sullivan: Good morning. Good morning. Dean Jackson: Good morning. Good morning. Our best to you this morning. Boy, you haven't heard that in a long time, have you? Dan Sullivan: Yeah. What was that? Dean Jackson: KE double LO Double G, Kellogg's. Best to you. Dan Sullivan: There you go. Dean Jackson: Yes, Dan Sullivan: There you go. Dean Jackson: I thought you might enjoy that as Dan Sullivan: An admin, the advertise. I bet everybody who created that is dead. Dean Jackson: I think you're probably right. Dan Sullivan: Yeah. I was just noticing that. Jaguar, did you follow the Jaguar brand change? Dean Jackson: No. What happened just recently? Dan Sullivan: Yeah. Basically maybe 24. They decided to completely rebrand. Since the rebranding, they've sold almost no cars and they fired their marketing. That's problem. Problem. Yeah. You can look it up on YouTube. There's about 25 P mode autopsies. Dean Jackson: Wow. Dan Sullivan: Where Dean Jackson: People are talking mean must. It's true. Because they haven't, there's nothing. It's pretty amazing, actually, when you think about it. The only thing, the evidence that you have that Jaguar even exists is when you see the Waymo taxis in Phoenix. Dan Sullivan: Is that Jaguar? Dean Jackson: They're Jaguars. Yeah. Dan Sullivan: I didn't know that. Yeah. Well, yeah, they just decided that they needed an upgrade. They needed to bring it into the 21st century. Couldn't have any of that traditional British, that traditional British snobby sort of thing. So yeah, when they first, they brought out this, I can't even say it was a commercial, because it wasn't clear that they were selling anything, but they had all these androgynous figures. You couldn't quite tell what their gender was. And they're dressed up in sort of electric colors, electric greens and reds, and not entirely clear what they were doing. Not entirely clear what they were trying to create, not were they selling something, didn't really know this. But not only are they, and then they brought out a new electric car, an ev. This was all for the sake of reading out their, and people said, nothing new here. Nothing new here. Not particularly interesting. Has none of the no relationship to the classic Jaguar look and everything. And as a result of that, not only are they not selling the new EV car, they're not selling any of their other models either. Dean Jackson: I can't even remember the last time you saw it. Betsy Vaughn, who runs our 90 minute book team, she has one of those Jaguar SUV things like the...

AI becomes a thinking partner, not a replacement, as Dan Sullivan and Dean Jackson compare their distinct approaches to working with artificial intelligence. In this episode of Welcome to Cloudlandia, we explore how Dan uses Perplexity to compress his book chapter creation from 150 minutes to 45 minutes while maintaining his unique voice. Dean shares his personalized relationship with Charlotte, his AI assistant, demonstrating how she helps craft emails and acts as a curiosity multiplier for instant research. We discover that while AI tools are widely available, only 1-2% of the global population actively uses them for creative and profitable work. The conversation shifts to examining how most human interactions follow predictable patterns, like large language models themselves. We discuss the massive energy requirements for AI expansion, with 40% of AI capacity needed just to generate power for future growth. Nuclear energy emerges as the only viable solution, with one gram of uranium containing the energy of 27 tons of coal. Dan's observation about people making claims without caring if you're interested provides a refreshing perspective on conversation dynamics. Rather than viewing AI as taking over, we see it becoming as essential and invisible as electricity - a layer that enhances rather than replaces human creativity. SHOW HIGHLIGHTS ​ ​ Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com ​ ​ ​ TRANSCRIPT(AI transcript provided as supporting material and may contain errors) Speaker 1: Welcome to Cloud Landia, Speaker 2: Mr. Sullivan? Speaker 1: Yes, Mr. Jackson. Speaker 2: Welcome to Cloud Landia. Speaker 1: Yes. Yeah. I find it's a workable place. Cloud Landia. Speaker 2: Very, yep. Very friendly. It's easy to navigate. Speaker 1: Yeah. Where would you say you're, you're inland now. You're not on Speaker 2: The beach. I'm on the mainland at the Four Seasons of Valhalla. Speaker 1: Yes. It's hot. I am adopting the sport that you were at one time really interested in. Yeah. But it's my approach to AI that I hit the ball over the net and the ball comes back over the net, and then I hit the ball back over the net. And it's very interesting to be in this thing where you get a return back over, it's in a different form, and then you put your creativity back on. But I find that it's really making me into a better thinker. Speaker 3: Yeah. Speaker 1: Yeah. I've noticed in, what is it now? I started in February of 24. 24, and it's really making me more thoughtful. Ai. Speaker 2: Well, it's interesting to have, I find you're absolutely right that the ability to rally back and forth with someone who knows everything is very directionally advantageous. I heard someone talking this week about most of our conversations with the other humans, with other people are basically what he called large language model conversations. They're all essentially the same thing that you are saying to somebody. They're all guessing the next appropriate word. Right. Oh, hey, how are you? I'm doing great. How was your weekend? Fantastic. We went up to the cottage. Oh, wow. How was the weather? Oh, the weather was great. They're so predictable and LLME type of conversations and interactions that humans have with each other on a surface level. And I remember you highlighted that at certain levels, people talk about, they talk about things and then they talk about people. And at a certain level, people talk about ideas, but it's very rare. And so most of society is based on communicating within a large language model that we've been trained on through popular events, through whatever media, whatever we've been trained or indoctrinated to think. Speaker 1: Yeah, it's the form of picking fleas off each other. Speaker 2: Yes, exactly. You can imagine that. That's the perfect imagery, Dan. That's the perfect imagery. Oh, man. We're just, yes. Speaker 1: Well, it's got us through a million years of...

In this episode of Welcome to Cloudlandia, we discuss our experiences working alongside an AI assistant named Charlotte. We explore how Charlotte helps us create personalized emails, enhancing our creativity and productivity. Through funny stories and thoughtful discussions, we see how AI is changing professional and creative landscapes. We also talk about the art of time management. The idea is to treat life like a game, where the goal is to achieve personal milestones within the time you have each day. By focusing on three main tasks and celebrating small victories, you can feel more accomplished. The conversation shifts to self-awareness and leadership in a virtual world. We discuss the importance of breaking away from predictability and using mental frameworks to capture and apply new ideas. The episode ends with a look at evolving creative partnerships, emphasizing the power of collaboration and being present with your audience. SHOW HIGHLIGHTS Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT(AI transcript provided as supporting material and may contain errors) Dean: Mr Sullivan. Dan: Mr Jackson, it's always good to hear your voice. Dean: Always wonderful, and it seems like this week went fast, faster than usual. But we all know, dan, it actually moved at the speed of reality, the speed of reality 60 minutes per hour. Speed of reality moved at the speed of reality, the speed of reality 60 minutes per hour. Dan: Speed of reality is like the law of gravity. That is the truth. Dean: Yeah, charlotte made me laugh out loud today. Dan: That's a good sign. Dean: actually, I'll tell you what I asked Charlotte this morning. I said what are the top 10 impacts you could have in my life? And she said here's a prioritized list of the top 10 impacts I can have, mapped by impact versus effort, with examples from your world. And it was so funny. She listed all these things. You know daily email companion. You know you talk, I type, I shape, title and polish. You know all of these things curate and repackage your IP, brainstorming and naming partner. You know all these high insight leverage. Dan: Then she started I said tell me more about that. Sounds to me like Charlotte wants this to be lifetime a lifetime relationship. Dean: I agree, and it's so funny. Dan: She included herself in all of your impact. Dean: Oh, yeah, and. But she referred back to all of our history. Right, I said tell me more about number one, right, my daily email companion. And she said you know you talk. I go straight. This is the highest impact, lowest friction thing we can do, because you already generate so many brilliant observations, frameworks, stories and examples just by being Dean Jackson. You live in a state of constant insight. My job is to harvest that in real time and shape it into daily emails that strengthen your relationship with your list, cement your authority as the world's most interesting marketer, create a growing archive of evergreen content, seed future books, offers, talks and more Boy. Dan: I mean Boy talk about a plug for online dating. I mean really types of emails we can create. Dean: an example that made me laugh out loud was, you know, personal notes, observations, story based personal notes, and the subject she had for that was I had eggs, bacon and clarity this morning Eggs, bacon and clarity. Dan: Yeah, eggs, bacon and clarity. Dean: Like that is legitimately funny Dan. Dan: I mean it's so like that is legitimately funny. Then, yeah, well, she's. You know. They say that I want you to take this in the right way, but that dogs take on the personality of their owner, you know. Dean: I mean it's so funny. Every email? Dan: No, I think you know, I find it really, really interesting. I mean that my sense is that you're that Charlotte is a medium that enables you to get in touch with you at your best. Dean: She said why this works so well for you. Because, one, you don't...

In this episode of Welcome to Cloudlandia, we explore the shifting landscape of expertise in the digital age. Our discussion starts by examining the sheer volume of digital content and how it challenges traditional learning and expertise. With AI playing a significant role, we consider how this technology might disrupt long-established institutions like universities, allowing individuals to gain expertise in new ways. We then take a historical journey back to the invention of the printing press, drawing parallels between past and present innovations. Using AI tools like ChatGPT, we uncover details about Gutenberg's early legal challenges, showcasing how AI can offer new insights into historical events. This approach highlights how asking the right questions can transform previously unknown areas into fields of expertise. Next, we discuss the changing role of creativity in an AI-driven world. AI democratizes access to information, enabling more people to create and innovate without needing institutional support. We emphasize that while AI makes information readily available, the challenge of capturing attention remains. By using AI creatively, we can enhance our understanding and potentially redefine what it means to be an expert. Finally, we consider the impact of rapid technological advancements on daily life. With AI making expertise more accessible, we reflect on its implications for traditional expert roles. From home renovation advice to navigating tech mishaps, AI is reshaping how we approach problems and solutions. Through these discussions, we gain a fresh perspective on the evolving landscape of expertise and innovation. SHOW HIGHLIGHTS Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT(AI transcript provided as supporting material and may contain errors) Dean: Mr Sullivan. Dan: But who's going to listen to all the transcriptions? That's what I want to know. Who's going to read them yeah, but what are they going to do with them? I don't know, I think it's going to confuse them actually. Dean: They're on to us. They're on to us. They're on to us and we're on to them. Dan: Yeah but it's a problem. You know, after a while, when you've overheard or listened to 3 million different podcasts, what are you doing with it? I know, is it going anywhere? Is it producing any results? You know, I just don't know that's really. Dean: It's funny that you say that right. Like there's, I and you have thousands of hours of recorded content in all of the podcasts. Like between you know, podcasting is your love language. How many five or seven podcasts going on at all time. And I've got quite a few myself. Dan: I have eight series. Dean: You've got eight series going on regularly 160 a year times, probably 13 years. Yeah, exactly. Dan: Let's say but there's 1,600. Let's say there's 1,600 and it adds up. Dean: Let's call that. We each have thousands of hours of on the record, on the record, on your permanent record in there. Yeah, because so many people have said uh you know, you think about how much people uh talk, you think about how much people talk without there being any record of it. So that body of work. I've really been trying to come to terms with this mountain of content that's being added to every day. Like it was really kind of startling and I think I mentioned it a few episodes ago that the right now, even just on YouTube, 500 hours a minute uploaded to YouTube into piling onto a mountain of over a billion available hours. Dan: It's more than you can. It's really more than you can get to. Dean: And that's when you put it in the context of you know, a billion. I heard somebody talk about. The difference between a million and a billion is that if you had,1 a second each second, for if you ran out, if you're spending that $1 a second, you would run out if you had a million dollars in 11 and a half days, or something like that and if you had a? billion dollars, it...

Today on Welcome to Cloudlandia, Our discussion unravels the surprises of Ontario's geography, the nuances of tariff wars, and the timeless drive for ambition, ensuring you're well-equipped with insights into how technology continues to redefine the global landscape. Discover how NuCom's innovative app is revolutionizing sleep and relaxation. We dive into the specifics of how its unique audio tracks, like "Summer Night," are enhancing REM and deep sleep, all while adding a humorous twist with a comparison to Italian driving laws. With separate audio for each ear and playful suggestions for use, you'll learn how this app is setting new standards for flexibility and effectiveness in achieving tranquility. Finally, we ponder the evolving nature of trust in a world increasingly dominated by AI and digital interactions. Drawing inspiration from thinkers like Jacques Ellul and Thomas Sowell, we discuss the societal shifts driven by technological advances and the potential need for encryption to verify digital identities. SHOW HIGHLIGHTS Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT(AI transcript provided as supporting material and may contain errors) Dean: Mr Sullivan. Dan: Ah, Mr Jackson. General Jackson. General Jackson. Dictator Jackson Dean: Now there's two thoughts that are hard to contain in the brain at the same time. Are you in Toronto or at the cottage today? At the cottage, look at you, okay. Dan: Yeah, all is well, very nice day, yeah, except our water went out and so we can't get it fixed until tomorrow morning because it's cottage country. Till tomorrow morning because it's cottage country. And you know, this is not one of those 24-7 everybody's available places on the planet. Dean: Where do people in cottage country go to get away from the hustle and bustle of cottage country on the weekends? Dan: Yeah, it's a good question. It's a good question. It's a good question they go about two hours north. Dean: It feels like that's the appropriate amount of distance to make it feel like you're getting away. Dan: In the wild. Dean: Yeah. Dan: So we're having to use lake water for priming the vital plumbing. Dean: The plumbing you have to do. Dan: You have to have pails of water to do that and we'll do. Even though it feels like a third world situation, that's actually a first world problem. Dean: You're right, you're exactly right. Dan: Yeah, yeah, beautiful day, though. Nice and bright, and the water is surprisingly warm because we had a cold winter and the spring was really cold and we have a very deep lake. It's about um the depth meters on the boats go down to 300 feet, so that's a pretty deep lake that's a deep lake. Yeah, yeah, so here we are here's a factoid that blew my mind. The province of Ontario, which is huge it's 1,000 miles north to south and it's 1,200 miles east to west has 250,000 freshwater lakes, and that's half the freshwater lakes on the planet. Isn't that amazing? Dean: Yeah, I heard a little. There's some interesting Ontario facts. I remember being awed when I found out that you could drive the entire distance from Toronto to Florida north and still be in Ontario. Dan: Yeah. Dean: Yeah, yeah. Dan: Yeah, If you go from the furthest east, which is Cornwall a little town called Cornwall to the furthest west, which is a town called Kenora Right, kenora to the furthest west, which is a town called canora right, uh, canora. It's the same distance from that as from washington dc to kansas city. Oh, that's amazing yeah I had a good. Dean: I had a friend who was from canora. He was an olympic decathlete, michael sm. He was on the Olympic decathlon team and that's where he was from Kenora, kenora. Dan: Mm-hmm. Yeah, yeah, it's a lot of big. I mean most of it's bugs, you know most of it's bugs. It's not, you know, the 90% of the Ontario population lives within an hour 100 miles of the? U, lives within an hour a hundred miles of the US. Yeah,...

In this episode of Welcome to Cloudlandia, I reconnect with Dan Sullivan for another wide-ranging conversation that blends current events, history, technology, and human behavior. We start by reflecting on the safety and comfort of life in Canada while discussing the news of missile strikes in Israel. From there, we explore the idea that innovation often advances when entrenched leaders move on—whether in science, business, or geopolitics. Dan brings up Thomas Kuhn’s idea that progress happens after the old guard exits, creating room for new ways of thinking. Our conversation shifts into the role of AI as a horizontal layer over everything—similar to electricity. We compare this shift to earlier transitions like the printing press and the rise of coffee culture. Dan shares his belief that while AI will transform systems, the core of human life will still revolve around handled needs and personal desires. We wrap by talking about convenience as the ultimate driver of progress. From automated cooking to frictionless hospitality, we recognize that people mostly want things to be “handled.” Despite how fast technology evolves, it’s clear that unless something is of deep personal interest, most people will let it pass by. As always, the conversation leaves room for reflection and humor, grounded in the reality that technological change doesn’t always mean personal change. SHOW HIGHLIGHTS Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT(AI transcript provided as supporting material and may contain errors) Dean: Mr Sullivan, Dan: Mr Jackson, I hope the rest of your day yesterday went well. Dean: Oh, delightful, I learned stuff yesterday. That was a very nice day, beautiful, beautiful weather today. You know what, dan, if you could, as an option at the Hazleton, upgrade to include your perfect weather for $1,000, this is what you'd order, it's this kind of day. Yeah, mid-70s perfect white fluffy clouds. Yes, it's why. Dan: Living in a safe, globally unimportant country. That's exactly right. Holy cow, I don't know if you've seen, yeah, what's uh? I woke up like literally just a few minutes ago seeing all the, uh, the raining missiles on israel right now from Iran. Have you seen that this morning? Dean: Oh yeah, there's a lot of them. Most of them don't hit anything and most of them are shot down, but still it puts some excitement in your day. Dan: I mean really, yeah, these ones look like. They're something unique about these ones that they're supersonicersonic and many of them are hitting, yeah, different than what we've normally seen. Like normally, when you see it, it's the, the iron dome or whatever is, you know, intercepting them, which is always interesting, but these ones are like Direct, like you can see them hitting in inrael that's. I mean, could you imagine, dan, like you, just look at how geographically we are. You know we've won the geographic lottery in where we're positioned here, you know, just realizing that's never. Even though you can, all you know you always take precautions with the umbrella above us, over the outside. Dean: But I mean still that today. I've lived in Toronto for 54 years now, just past the anniversary, the 54th anniversary and I think that, first of all, when you have a really large city like Toronto, the center of a lot of things that go on in Canada, A world-class city like Toronto. Well, it's not a world-class city. But yeah, they have to go five years. I'm putting a new rule in for world-class cities. You have to go five years without ever saying the words. Dan: Yeah, we're a world-class city. Dean: We're a world-class city. And that takes you to stage one probation. Dan: Yeah. Dean: No, that takes you to stage two, probation, and then stage three probation is where all the people who've been saying it's a world-class city have either died or moved, and then it's sort of like science. There was a famous he wasn't a...

In this episode of Welcome to Cloudlandia, Dan and I talk about how much AI is reshaping everyday life. I share how new tools like Google’s Flow V3 are making it easier than ever to create video content, while Dan explores how AI could tackle complexity—like managing city traffic or enhancing productivity—when it's applied intentionally. We also look at how people are adapting to the massive increase in content creation. I ran some numbers: Americans spend around 450 minutes per day on screens, but YouTube alone sees 500 hours of content uploaded every minute. So while AI makes it easier to create, attention remains limited—and we’re all competing for it. Another theme is “agency.” We discuss how autonomous vehicles, digital payments, and convenience tools reduce friction, but can also make people feel like they’re giving up control. Dan points out that even if the technology works, not everyone wants to let go of driving, or of how they interact with money. Lastly, we reflect on what it really means for tools to be “democratized.” I talk about Hailey Bieber’s billion-dollar skincare brand and the importance of vision, capability, and reach. The tools might be available to everyone, but outcomes still depend on how you use them. We end with thoughts on tangibility and meaning in a world that’s becoming more digital by the day. SHOW HIGHLIGHTS Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT(AI transcript provided as supporting material and may contain errors) Dean: Mr Sullivan. Dan: How are things in Florida Hot? Dean: Hot, it's hot. Dan: It's hot. Dean: They're heated up. Dan: It's normal. Dean: Yeah, no, this is like it's unusual. It went from perfect to summer, All just overnight. I'm looking forward to coming to. I'm looking forward to coming to Toronto, to coming to. I'm looking forward to coming to Toronto Two weeks right, Two weeks here. Dan: Friday. I'm actually uh, You're going to spend a week. Dean: Yeah, I'm in. Dan: Chicago. I'm in Chicago next week. Dean: Yeah, I'm in. So I'm. Yeah, I'm coming for three weeks. Dan: You're holding court. You're holding court. Dean: I'm holding court every which way I arrive on Friday, the 6th, and I leave on the 29th, so there. So you are going to be in Chicago next Saturday. Dan: Next Saturday you're in Chicago, yeah, until the Friday and then back home and we'll have our. Whether it's table 9 or not, it's going to be table 9. Let's just call it table 1, because it'll be at restaurant one. Dean: That's exactly right. Dan: It'll probably be nice to maybe even sit outside, which is a very good restaurant. Yes, on the patio. Yeah, yeah, that's great. Well, canada is going through profound changes. Dean: That's what I hear, so prepare me. I'm already prepared that I will be ordering Canadians with breakfast instead of Americanos. Dan: They've already conditioned me for that. I've been here 54 years in Toronto 54 years and over 54 years I've never gotten a good answer about what a Canadian is. Dean: Okay. Dan: Okay, except that we're not Americans. We're not Americans. And to prove it, and to prove it, they brought the King of England over to tell them Okay, ah that's funny. Dean: I didn't see anything about that. Is that just that yeah? Dan: we came over. They have a thing called the throne speech. When parliament resumes after an election, it's called the throne speech. Dean: Okay, just a reminder. Dan: Yeah, and so just to tell you that we're an independent, completely independent country, we got the King of England to come over and talk to his subjects. Dean: And. Dan: I guess that's what caused the division in the first place, wasn't it? Dean: was the King of. Dan: England. So nothing's changed in 236 years. It's all been. You know the royalty. They brought the royalty over to put some muscle into the Canadian identity, anyway. But there is a profound change and I don't know if you knew this, but there's...

In this episode of Welcome to Cloudlandia, we kick off by reflecting on a recent trip to the UK, where London's unexpected warmth mirrored the friendliness of its black cab drivers. Our visit coincided with the successful launch of the 10 Times program in Mayfair, which attracted participants from various countries, adding a rich diversity to the event. Next, we delve into the advancements in AI technology, particularly those related to Google Flow. We discuss how this technology is democratizing creative tools, making it easier to create films and lifelike interactions. This sparks a conversation about the broader implications of AI, including its potential to transform industries like real estate through AI-driven personas and tools that enhance market operations. We then shift our focus to the political arena, where we explore the Democratic Party's attempt to create their own media influencers to match figures like Joe Rogan. The discussion centers on the challenges of capturing consumer attention in a world overflowing with digital content, and the need for meaningful messaging that resonates with everyday life. Finally, we touch on aging, longevity, and productivity. We emphasize the importance of staying engaged and productive as we age, inspired by remarkable individuals achieving significant milestones beyond 60. SHOW HIGHLIGHTS Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT(AI transcript provided as supporting material and may contain errors) Dean: Mr sullivan it has to be recorded because it's uh historic thinking it's historic thinking in a historic time things cannot be historic if they're not recorded, that is true, it's like if, uh, yeah, if a tree falls in the forest yeah, it's a real. Dan: It's a real problem with what happened here in the Americas, because the people who were here over thousands of years didn't have recordings. Dean: They didn't write it down. They didn't write it down. Dan: No recordings, I mean they chipped things. Dean: They didn't write it down. Dan: They didn't write it down no recordings, no recordings. Yeah, I mean, they chip things into rock, but it's, you know, it's not a great process really. Dean: I think that's funny, you know, because that's always been the joke that Christopher Columbus, you know, discovered America in 1492. But meanwhile they've been here. There have been people, the sneaky Vikings, and stuff. How do you explain that in the Spaniards? Dan: Yep. Dean: Yeah. Dan: Yeah Well, writing. You know, writing was an important thing. Dean: Yeah, yeah. Dan: We don't know much. We don't, yeah, we really don't know much about the Vikings either, because they didn't they weren't all that great at taking notes. I mean, all the Vikings put together don't equal your journals. Dean: That's true. All the Viking lore's the not what's happening. So it's been a few weeks yeah I was in the uk, we were in the uk for a couple weekends for uh-huh okay, it was great, wonderful weather, I mean we had the very unusual. Dan: It was great, wonderful weather. Dean: I mean we had the very unusual weather for May. It was, you know, unseasonably warm 75, 80, nice bright oh my goodness. Dan: Yeah, really terrific. And boy is the city packed. London is just packed. Dean: And getting packed dirt, huh. Dan: Yeah, yeah, just so many people on the street. Dean: I always, I always laugh, because one time I was there in June which is typically when I go, and it was. It was very funny because I'd gotten a black cab and just making conversation with the driver and he said so how long are you here? And I said I'm here for a week. He said, oh, for the whole summer, because it was beautifully warm here for the whole summer. Yeah, that's so funny, I hear hear it's not quite. Dan: They're fun to talk to. Dean: Oh man for sure. Dan: Yeah, they know so much. Dean: Yes, I hear Toronto. Not quite that warm yet, but get in there I think today is...

In this episode of Welcome to Cloudlandia, we start with Dan’s recent experience with stem cell injections, a journey filled with both challenges and relief. This discussion transitions into the inspiring story of a Vietnamese massage therapist who built her career in Canada, highlighting the diverse paths in the healing professions. Our conversation then shifts to the political landscape of Canada. We analyze the unique dynamics of minority governments and consider the influence of international figures like Trump on Canadian politics. We also discuss the role of central banking figures in political negotiations and reflect on the contrasts between Canadian and American electoral perspectives. Next, we explore the parallels between political and economic systems, examining the shift from traditional hierarchies to modern digital frameworks. The conversation covers the challenges faced by third-party candidates in the U.S., with a focus on Robert F. Kennedy's independent run, and delves into the economic tensions between China and the U.S., considering their impact on global trade relations. Finally, we reflect on the importance of creative consistency and the power of legacy. Whether it's maintaining a long-term streak of publishing or creating innovative tools, we emphasize the value of continuously producing impactful content. SHOW HIGHLIGHTS Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT(AI transcript provided as supporting material and may contain errors) Dean: Mr Sullivan, Dan:Mr Jackson, Dean: there he is. How are things in your outpost of the? Dan: mainland. Well good, I had a convalescence week. They really packed me full of new stem cells. And the procedure is things aren't good if I'm not feeling bad. Dean: That's what I'm saying. It's along the lines of we're not happy until you're not happy. Dan: How's that for a closing argument? Dean: That's good, that's good. Dan: Yeah. Dean: Things aren't good if you're not feeling bad. Dan: I got the procedure on the Thursday of last week, not the week we're just finishing, but the week. So Thursday, friday, saturday and it was almost one week later, exactly on Thursday, almost the same time of day, and all of a sudden the pain went away. Dean: Okay, how long was it Acute onset? Did you have to travel in pain? Dan: Yeah, well, I did, but they drugged me out. Yeah, they had sedatives Right when they were doing the procedure and then you had takeaways. Dean: Yeah, A goody bag. Dan: Nothing like a good drug. Yeah, exactly, especially a pa pain killing drug and and they're real big on this but went full force this time I had eight different injections, both ankles, both knees, even the knee. That's good they do it to reinforce what's already there. Reinforce what's already there. And then tendons the tendons in the calf, tendons in the hamstring, tendons in the quadriceps and then on both hips, both hips, so the left leg is the. You know in the spotlight here and when you're it's like you're experiencing inflammation in the ankle, in the calf, in the knee, in the upper leg and then the hip at the same time the leg doesn't want to, the leg doesn't want to work, right exactly yeah yeah, so that's the big problem, but actually I'm feeling pretty chipper today that's great, so that. Dean: So it took a week to get that. Is that usual or was this an unusual? Because I don't think I've ever heard you mention the pain. Dan: Usually it was a couple of days, but they got me while they had me. Dean: Well, that's good, and today you feel noticeably better. Dan: Now, yeah, I was noticing that we have a long-term massage therapist who comes to our house. Dean: Oh, my goodness. Dan: She's been coming for 33 years. Vietnamese Wow A boat person, actually, someone who escaped on a boat when she was a teenager, actually someone who escaped on boat when she was a teenager. And you know, really, she grew up, her grandmother was....

In this episode of Welcome to Cloudlandia, I chat with Dan about his recent journey to Buenos Aires for stem cell therapy on his knee. After living with an injury since 1975, he shares how advancements in medical technology are providing new solutions for pain and mobility. We discuss the challenges of recovery and the impressive potential of these therapies, along with vivid stories from his experience in this vibrant city. We also touch on the role of AI in our modern landscape, questioning its reliability and pondering whether it enhances creativity or simply recycles existing ideas. As we explore the implications of AI, we consider how it can assist in achieving desired outcomes without requiring individuals to develop new skills themselves. Sullivan emphasizes the importance of meaningful work and the balance between utilizing technology and fostering genuine human creativity. Our conversation wraps up by highlighting the ongoing journey of personal growth and the need for continuous improvement in an ever-evolving world. SHOW HIGHLIGHTS Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT(AI transcript provided as supporting material and may contain errors) Dean: Mr. Sullivan. Dan: Mr Jackson, it's been a while, it's been a while. Dean: And yet here we are. Like no time has passed. Dan: Yes. Dean: Because it's now. Dan: But I've put on a lot of bear miles since I saw you last. Dean: Yeah, tell me about your journeys. Dan: Yeah well, buenos Aires. Yep Just got back yesterday and am in considerable pain. Oh really what happened. Well, they give you new stem cells. So now, they're going after. They're going still on the knee, but now they're going after tendons and ligaments, yeah, and so this may seem contrarian, but if you're in pain, it means that they're working. Dean: Oh, okay. Dan: How's that? For a compelling offer If you feel really bad about this, it means that what I'm offering you is a great solution. Dean: Yeah, with a name like Smuckers, it's got to be good, right yeah? What was that cough syrup that was known to taste so bad? Buckley's, buckley's. Dan: Tastes so bad. Tastes awful Works great. Dean: Yeah, that's right. That's the perfect thing. Tastes awful, works great. So were they completely pleased with your progress. Dan: it's, yeah, I think that the from what I can tell from they. They show you pictures of other complete cartridges. You know, okay, with other people and my left this is my left knee an injury from 1975. 1975, uh-huh, so 50 years, and it progressively wore down. It was a meniscus tear and in those days they would remove the torn part of the meniscus, which they don't do anymore. They have new surgical glue and they just glue it back together again. But this is the. This is one of the cost of living in over a period of history where things get better and so, as a result, I have a cartilage today which is equal and capability as it was before I tore it in 1975. However, all the adjustments my left leg and my head to make, 50-year period of adjusting to a deteriorating capability in my left there was a lot of calcification and stresses and strains on the tendons. So now that they can see the complete cartilage back, they can know exactly what they have to do with the otherons. So now that they can see the complete cartilage back, they can know exactly what they have to do with the other things. So they still reinforce it. So I get new stem cells for the cartilage because it has to be reinforced and so it's a good thing. I'm planning to live another 75 years because I think every quarter over that period I'm going to be going to Argentina. Dean: Oh boy, this is great. Dan: Or Argentina, is coming to me. They're going through their FDA phases right now and he's getting the doctor scientist who created this is getting his permanent resident card in the United States. So I think probably five years five years it'll be available to...