
Welcome to Cloudlandia
Business & Economics Podcasts
Join Dean Jackson and Dan Sullivan as they talk about growing your business and living you best life in Cloudlandia.
Location:
United States
Description:
Join Dean Jackson and Dan Sullivan as they talk about growing your business and living you best life in Cloudlandia.
Language:
English
Episodes
When AI Becomes Your Thinking Partner
8/27/2025
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...
Duration:00:51:40
Ep160:AI and the Future of Creative Work
7/16/2025
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...
Duration:00:59:15
Ep159: Unlocking the Future of Learning
7/8/2025
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...
Duration:01:01:59
Ep158: AI's Role in Shaping Global Dynamics
7/2/2025
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,...
Duration:01:01:32
Ep157: Unveiling Toronto's Dual Identity
6/25/2025
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...
Duration:00:46:01
Ep156: Convenience Versus Tradition
6/16/2025
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...
Duration:00:53:14
Ep155: The Allure of AI in Real Estate and Beyond
5/28/2025
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...
Duration:00:54:05
Ep154: From Stem Cells to Geopolitical Tensions
5/7/2025
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....
Duration:00:50:58
Ep153: Exploring the Crossroads of Health and Technology
4/30/2025
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...
Duration:00:49:27
Ep152: Exploring Time Zones and Trade
4/9/2025
In this episode of Welcome to Cloudlandia, we start by unraveling the intriguing concept of global time zones. We humorously ponder the idea of a unified world clock, inspired by China's singular time zone. The discussion expands to how people in countries like Iceland adapt to extreme daylight variations and the impact of climate change narratives that often overlook local experiences. We then explore the power of perception and emotion in shaping our reactions to world events. The conversation delves into how algorithms on platforms shape personal experiences and the choice to opt out of traditional media in favor of a more tailored information stream. The shift from curated media landscapes to algorithm-driven platforms is another key topic, highlighting the challenges of navigating personalized information environments. Finally, we tackle the critical issue of government financial accountability. We humorously consider where vast sums of unaccounted-for money might go, reflecting on the importance of financial transparency. 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: Yes, and I forgot my time zones there almost for a second. Are you in Chicago? Yeah, you know. Why can't we just all be in the same time zone? Dean: Well. Dan: I know that's what China does. Yeah, Well, that's a reason not to do it. Then you know, I learned that little tidbit from we publish something and it's a reason not to do it. Dean: then that was. You know I learned that little tidbit from. We publish something and it's a postcard for, you know, realtors and financial advisors or business owners to send to their clients as a monthly kind of postcard newsletter, and so every month it has all kinds of interesting facts and whatnot, and one of them that I heard on there is, even though China should have six time zones, they only have one. That's kind of an interesting thing. Imagine if the. United States had all one time zone, that would be great. Dan: Yeah, I think there would be advantages and disadvantages, regardless of what your time system is. Dean: Well, that'd be like anything really, you know, think about that. In California it would get light super early and we'd be off a good dock really early too we'd be off and get docked really early too. Yeah, I spent a couple of summers in Iceland, where it gets 24 hours of light. Dan: You know June 20th and it's. I mean, it's disruptive if you're just arriving there, but I talked to Icelanders and they don't really think about it. It's, you know, part of the year it's completely light all day and part of the year it's dark all day. And then they've adjusted to it. Dean: It happens in Finland and Norway and Alaska. We're adaptable, dan, we're very adaptable. Dan: And those that aren't move away or die. Dean: I heard somebody was talking today about. It was a video that I saw online. They were mentioning climate change, global warming, and that they say that global warming is the measurement is against what? Since when? Is the question to ask, because the things that they're talking about are since 1850, right, it's warmed by 0.6 degrees Celsius since 1850. We've had three periods of warming and since you know, the medieval warming and the Roman warming, we're actually down by five degrees. So it's like such a so when somebody says that we're global warming, the temperature is global warming and the question is since when? That's the real question to ask. Dan: Yeah, I think with those who are alarmist regarding temperature and climate. They have two big problems. They're language problems, Not so much language, but contextual problems. Nobody experiences global. That's exactly right. The other thing is nobody experiences climate. What we experience is local weather. Dean: Yes. Dan: Yeah, so nobody in the world has ever...
Duration:00:50:13
Ep151: A Journey Through Technology and Personal Growth
4/3/2025
In this episode of Welcome to Cloudlandia, we start by discussing the unpredictable nature of Toronto's weather and its amusing impact on the city's spring arrival. We explore the evolution of Formula One pit stops, highlighting the remarkable advancements in efficiency over the decades. This sets the stage for a conversation with our guest, Chris Collins, who shares his insights on balancing fame and wealth below the need for personal security. Next, we delve into the intricacies of the VCR formula—proposition, proof, protocol, and property. I share my experiences from recent workshops, emphasizing the importance of transforming ideas into intellectual property. We explore cultural differences between Canada and the U.S. in securing property rights, highlighting the entrepreneurial spirit needed to protect one's innovations. We then examine the role of AI in government efficiency, with Elon Musk's technologies revealing inefficiencies in civil services. The discussion covers the political and economic implications of misallocated funds and how the market's growing intolerance for waste pushes productivity and accountability to the forefront. Finally, we reflect on the transformative power of technological advancements, drawing parallels to historical innovations like the printing press. 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: That feels better. Dean: Welcome to Cloudlandia, yes. Dan: Yes indeed. Dean: Well, where in the world? Dan: are you? Dean: today, toronto. Oh, you're in Toronto. Okay, yeah, where are you? Yeah? Dan: where are you? Dean: I am in the courtyard at the Four Seasons Valhalla in my comfy white couch. In perfect, I would give it 73 degree weather right now. Dan: Yes, well, we're right at that crossover between middle winter and late winter. Dean: You never know what you're going to get. It could snow or it could be. You may need your bikini, your Speedo or something. Dan: I think spring in Toronto happens, I think somewhere around May 23rd, I think somewhere around. May 23rd, and it's the night when the city workers put all the leaves on the trees. Dean: You never know what you're going to get. Until then, right, it just might snow, and they're stealthy. Dan: They're stealthy and you know, I think they rehearse. You know, starting in February, march, april, they start rehearsing. You know how fast can we get all the leaves on the trees and they do it all in one night they do it and all. I mean they're faster than Santa Claus. I mean they're. Dean: Have you seen, Dan? There's a wonderful video on YouTube that is a comparison of a Formula One pit stop from the 1950s versus the 2013 Formula One in Melbourne, and it was so funny to show. Dan: It would be even faster today. Dean: It would be even faster today. Oh yeah, 57 seconds it took for the pit stop in the 50s and it was 2.7 seconds at Melbourne it was just amazing to see. Dan: Yeah, mark young talks about that because he's he's not formula one, but he's at the yeah, he's at the level below formula one right, every, uh, every minute counts, every second counts oh, yeah, yeah, and uh, yeah, he said they practice and practice and practice. You know it's, it's, if it can be measured. You know that there's always somebody who's going to do it faster. And yeah, yeah, it's really, really interesting what humans do. Dean: Really interesting what humans do. I read something interesting or saw a video and I've been looking into it. Basically, someone was saying you know, our brains are not equipped for omniscience, that we're not supposed to have omniscient knowledge of everything going on in the world all at once. where our brains are made to be in a local environment with 150 people around us, and that's what our brain is equipped for managing. But all this has been foisted on us,...
Duration:01:05:44
Ep150: Unexpected Skies and Local Legends
3/26/2025
In this episode of Welcome to Cloudlandia, we reflect on how places, people, and experiences shape our perspectives. The conversation begins with casual observations, from warm weather making transitions easier to memorable encounters like “Spam Man,” a mysterious figure spotted at the Hazleton Hotel. We also explore the impact of changing landscapes, both physical and cultural. From real estate in Toronto to how cities evolve, we discuss how development can shape or diminish the character of a place. This leads to a broader conversation about timeless architecture, like Toronto’s Harris Filtration Plant, and how thoughtful design contributes to a city’s identity. Technology’s role in daily life also comes up, especially how smartphones dominate attention. A simple observation of people walking through Yorkville reveals how deeply connected we are to our screens, often at the expense of real-world engagement. We contrast this with the idea that some things, like human connection and cooperation, remain unchanged even as technology advances. The discussion closes with thoughts on long-term impact—what lasts and fades over time. Whether it’s historic buildings, enduring habits, or fundamental human behaviors, the conversation emphasizes that while trends come and go, specific principles and ways of thinking remain relevant across generations. 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 you behaved when you were out of my sight. Dean: I did. I'll have to tell you something. I can't tell you how much I appreciate the arrangement of this warm weather. For me, it's made the transition much more palatable warm weather. Dan: for me it's made the transition much more palatable. Dean: I mean our backstage team is really getting good at this sort of thing, and you know when we were in. Dan: we were in Phoenix a couple of weeks ago and we had a rooftop party and right in the middle of the party we arranged for Elon Musk to send one of his rockets out. Dean: I saw that a satellite launch yeah. Dan: Yeah, can you imagine that guy and how busy he is? But just you know, just to handle our request he just ended up with, yeah, must be some money involved with that. Dean: Well, that's what happens, Dan. We have a positive attitude on the new budget. Dan: Yeah, and you think in terms of unique ability, collaboration, you know, breakthroughs free zone you know, all that stuff, it's all. Dean: it's the future. Dan: Yeah. So good Well he sent the rocket up and they're rescuing the astronauts today. Dean: Oh, is that right? How long has it been now since they've been? Dan: It's been a long time seven, eight months, I think, Uh-huh, yeah and Boeing couldn't get them down. Boeing sent them up, but they couldn't get them down. You know, which is only half the job, really. Dean: That was in the Seinfeld episode about taking the reservation and holding the reservation. Yeah. They can take the reservation. They just can't hold the reservation yeah. Dan: It's like back really the integral part. Back during the moonshot, they thought that the Russians were going to be first to the moon. Kennedy made his famous speech. You know we're going to put a man on and they thought the Russians, right off the bat, would beat him, because Kennedy said we'll bring him back safely and the Russians didn't include that in their prediction. That's funny. Dean: We had that. We're all abuzz with excitement over here at the Hazleton. There's a funny thing that happened. It started last summer that Chad Jenkins Krista Smith-Klein is that her name yeah, yeah. So we were sitting in the lobby one night at the Hazleton here and this guy came down from the residences into the lobby. It was talking to the concierge but he had this Einstein-like hair and blue spam t-shirts that's, you...
Duration:00:50:34
Ep148: Unexpected Snow in the Sunshine State
3/5/2025
In this episode of Welcome to Cloudlandia, We explore the unexpected weather patterns that challenge our understanding of climate and geography. A surprising cold snap in Florida becomes the starting point for a broader conversation about climate variability. Dan shares personal experiences from Phoenix and Edmonton, highlighting the dramatic temperature shifts that reveal the complexity of our planet's weather systems. Our discussion then turns to the human fascination with Earth's resilience and our speculative nature about the world's potential existence without human presence. These reflections provide a unique lens for understanding climate change, moving beyond abstract data to personal observations and experiences. The unpredictability of weather serves as a metaphor for the broader environmental transformations we're witnessing. Shifting gears, we delve into a critical political discourse centered on the fundamental question: "Who pays for it?" We examine policy proposals ranging from universal basic income to more ambitious financial initiatives. The conversation explores the complex financial dynamics of such proposals, particularly how higher-income earners often bear the primary financial burden. 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: Well, did you thaw out? Dean: I am in the process of thawing out. This has been a Bizarre, I finally saw the sun came out. Yesterday I was having a chat with charlotte about the weather and there's only been two days in january where the temperature has been above 70 degrees. Yeah, this has been an unusually cold and rainy january. We actually had snow up in the northern part of Florida. Dan: Tallahassee, I think had snow. Dean: Yeah, Tallahassee had snow all the way down to Pensacola. Dan: I think, yeah, all the way down to Pensacola. Dean: The whole panhandle had snow, it's not good. No bueno, as they say. Dan: Well, they said things were going to be different with Trump. Dean: Well, here we are, six days in and the sun's already out, dan, it's warming up. That's so funny. Dan: Yeah, and people in the South really aren't prepared for this, are they? Dean: No, and I can speak as a Southerner. Dan: You actually have an ancestral memory of things being really cold. I mean, you were born in a very cold place. That's right, you know so I'm sure you know that got imprinted somehow on your. Dean: I think so I must have genetic, like I must have the, you know, the active pack for super cold weather. It must be installed at a genetic level when you're born in a certain area right, but it doesn't explain I don't prefer it at all. Dan: Now Babs and I are on Tuesday, are flying to Phoenix and we'll be there for two and a half weeks Two and a half weeks we'll be there. And it'll be like maybe 65 degrees and the Arizonians will be complaining about it. And I said you have no sense of perspective. Dean: Right. Dan: You have no sense of perspective and anyway, you know I think I've mentioned this before this is the biggest obstacle that the global warming people have. Dean: How do we explain this cold no? Dan: One of their biggest problems is that nobody experiences climate. We only experience weather. Yes, yeah, and it's like abstraction that they try to sell. But nobody experiences abstractions. They experience reality, and it must be very frustrating for them. It must be very frustrating for them. They discovered, for example, that Antarctica now with really accurate readings has actually cooled over the last 20 years, that, year by year by year, there's actually been a cooling in Antarctica. And the same thing goes for Greenland. Greenland has actually gotten colder over the last 20 years and they keep trying to sell a different message. But, the actual, now the records, because they made claims 20 years ago...
Duration:00:59:25
Ep147: Cultural Ripples and Modern Innovations
2/26/2025
In this episode of Welcome to Cloudlandia, Dan and I explore technology and communication sparked by an unexpected conversation about cold snaps in Florida. We examine the evolution of communication technologies, from text to video, focusing on AI's emerging role. Our discussion highlights how innovations like television and the internet have paved the way for current technological developments, using the progression of airliners as a metaphorical framework for understanding technological advancement. Our conversation shifts to exploring human interaction and technological tools. We question whether platforms like Zoom have reached their full potential, emphasizing the importance of self-awareness and collaboration. We then journey back to 1967, reflecting on historical and cultural movements that continue to shape our current societal landscape. This retrospective provides insights into how past experiences inform our present understanding of technology and social dynamics. Personal anecdotes and political observations help connect these historical threads to contemporary discussions. 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, that would be me. Oh my goodness. Dan: I am not Do you have a cold? Dean: Do you have a cold? Dan: I do yeah. Dean: And is it freezing in Florida? Dan: It's very cold, it's unseasonably. Dean: Comparatively comparatively yes. Dan: It's unseasonably cold. Dean: Yeah. Yeah, well, we're getting our blast tomorrow, but it's colder than yeah. It's about 15 today with a 10 mile an hour wind which makes it 5, and tomorrow it's going down. It's going down even further. This is the joy of Canada in January. Dan: I don't know about the joy. Dean: But yeah, I like your voice I like your voice. Dan: I'm going to try and uh and make it all the way through, dad, but the uh just before you, I'm. Dean: You can put charlotte on. Dan: Yeah, exactly, yeah yeah, I'll tell you, I'm really realizing how, how incredible these conversations like. I really start to think and see how charlotte's um capabilities as a researcher. Dean: And uh, dean dean, I can't hear you. Dan: I'm trying to switch to my other uh headphones. But as long as you can hear me, can you hear me now? Dean: yeah, yeah, it's very good, okay good. Dan: Good, good good. Dean: I like this voice, though you know. Dan: It's got. Oh, really Okay, yeah, yeah, the baritone. Dean: Yeah, I mean you might create another version of yourself, you know which? Oh yeah, I should quick get on 11 Labs. I don't know if this would be your main course, but it would certainly be a nice seasoning. As a matter of fact, you could have on 11 Lab, you could go with them and you could have your normal voice as one of the partners and you could have this voice as the other partner. There you go, you could talk to each other. See, that makes a lot of sense right there. Yeah, it's so good. The reason the reason I'm saying this is I just had a whole chapter it is being done, I'll probably have it on tuesday, this being sunday of of one of the chapters of the book Casting Not Hiring, in two British voices, man and a woman, and it's charming, it's very charming. Dan: Really Wow. Dean: I really like it and they're more articulate. You know, brits, they invented the language, so I guess they're better at it. Yeah, that's what I really like about Charlotte's voice is the reassuring right, yeah, yeah, you get a sense that she's had proper upbringing. Dan: Mm-hmm, exactly, worldly wisdom. Well, certainly she's got command of the language yeah, the uh I was mentioning before I cut off there that uh, I was. I'm really coming to the realization how valuable charlotte is as a research partner. You, you know, a conversational, like exploration, like getting to the bottom of things, like I was. I've just fascinated how I...
Duration:00:51:16
Ep146: The Tides of Media and Innovation
2/19/2025
In this episode of Welcome to Cloudlandia, We take you through the fascinating evolution of media and communication technologies. We begin by tracing the journey of written communication from ancient Sumerian pictographs to Gutenberg's printing press. The narrative explores how each technological breakthrough transformed our ability to share information, from industrial-era steam presses to the digital revolution sparked by the first email in 1971. Our conversation delves into the parallels between historical technological adaptations and current innovations. We examine the story of a 1950s typesetter transitioning to digital technologies, drawing insights into how professionals navigate significant technological shifts. The discussion introduces the concept of "Casting, not Hiring," emphasizing the importance of finding meaningful experiences and team dynamics in a rapidly changing world. We explore the transformation of media consumption and advertising in the digital age. Traditional media platforms give way to digital giants like Facebook and Google, reflecting broader changes in how we create, distribute, and consume content. The conversation touches on audience dynamics, using examples like Joe Rogan's media presence and Netflix's market evolution to illustrate these shifts. 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, and how are you? I am wonderful. Welcome to Cloudlandia, you are in the Chicago outpost. I am. Dan: I'm sitting in a very comfortable spot, noise-free. I just had. Have you ever done any IV where they pump you? Up with good stuff. Dean: I have yeah. Dan: Yeah, I just came from that, so I may be uncomfortably exuberant. Dean: Uncomfortably exuberant. That's a great word there, right there. Dan: Yeah, yeah, uncomfortable to you. Dean: That's the best. Dan: Yeah, yeah. So anyway, we have a good service. Dean: The only thing I miss about Chicago comfortable to you, that's the best, yeah, so anyway, we have a good service. The only thing I miss about Chicago. Dan is our Sunday dinners. Oh the Sunday roundtable. Dan: Yeah, it's a bit more informal now so we don't have a big gap. It's not like the Last Supper. Dean: Right, exactly. Dan: We have Mike Canix coming over and Stephen Paltrow. Dean: Okay, there you go. Dan: They'll be on straight carnivore tonight. Dean: Okay, good, I like everything about that. Dan: Yeah, it's a little bit of snow on the ground and snowing right now, but it's nice. Dean: Oh, that's awesome. Well it's winter here. It's like cool. Yeah, I almost had to wear pants yesterday, dan, it was that cold. Dan: I had to wear pants yesterday, Dan. Dean: It was that cold I had to wear my full-weight hoodie. But yeah, but it's sunny, it's nice. Dan: I was just in the hot tub before we got on the call the Chinese intelligence, who are listening to this phone call. They're trying to visualize what you just said. Dean: Yes, Well, I had a great conversation with Charlotte this morning and something happened. That is the first time I've done it. I literally I talked her ear off. I reached my daily limit of talk interaction. We were talking for about an hour. There's a limit. Yes, I pay $20 a month and I guess there's a limit of how long you can engage by advanced voice tech. Dan: I'd give her a raise. I'd give her a raise. Dean: So they were on her behalf demanding a raise. I'd give her a raise. So they were on her behalf demanding a raise from $20 a month to $200 a month, and I could talk to her all I want. I still think it's worth it. It really is. When you think about if we go through the personification again, if you think about what you're getting for 200 I mean, just the conversation I had with her this morning was worth more than 200, yeah, so you want to know what we were talking about. What were you talking? about well,...
Duration:00:55:03
Ep149: Finding Balance in a High-Tech World
2/19/2025
In this episode of Welcome to Cloudlandia, Dan shares his journey from recovering in snowy Toronto to basking in the Arizona sunshine at Canyon Ranch. While battling a cold and back spasm in Canada, He found unexpected humor in a limousine driver discovering our heated driveway before making my way to the warmth of Tucson. At Canyon Ranch, I read historical British Navy novels and attended Richard Rossi's conference, where conversations sparked insights about technology's role in our world. The discussions centered on how companies like Google and Apple influence geographic naming conventions and how AI tools like ChatGPT and Claude work to match human capabilities rather than surpass them. We explored the relationship between technology and daily life, from electric vehicles to meal delivery services. These conversations highlighted how technological advances aim to streamline our routines while acknowledging the challenge of replicating genuine human experiences. The experience reinforced that technology offers convenience and efficiency but cannot replace authentic human connections and experiences. This balance became clear through examples like distinguishing between Bach's original compositions and AI-generated music, reminding us of technology's role as a tool rather than a replacement for human interaction. 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. Mr Jackson, I hope you're well, I am. Dan: I'm much better than I was last weekend. I was, yeah, out of it. I mean, really I had like a cold and my back was in spasm. It was not good. So I'm a nice recovery week and I'm on the mend. How was your adventures in Arizona? Are you still in Arizona? Dean: now. No, I got back around 11 o'clock last night to Toronto. That has about a foot of snow. Dan: I saw that. Dean: Yeah, and it's still snowing, it's still coming down. So we really had nothing for November, december, january, but February seems to be the winter. It's really snowing, I mean it's continuous, it's not heavy snow, but it's just constant, and I kind of like it. And we got home last night and the limousine driver who driveway and he said, oh, I hope we can get up to your driveway and he, he hadn't uh, he didn't have previous he didn't have previous experience. He says oh my golly, you have heated driveways. And I said, yeah, uh, of course you know we've got to be good to our got to be, good to our limousine drivers. Dan: You know we have to you know, set a standard for driver friendliness and anyway, so Did he tell you, listen, if you wanted to really be good, you'd buy the house behind you so we could keep the driveway going all the way through. Dean: Yeah, somebody else did and they fixed it up, so I think that's out of the future. That's out of the. You know that's not going to happen. You can't add that to the compound, right? Yeah, so anyway, regarding Arizona, it was great. We were there for two and a half weeks so we had Richard Rossi's conference which was terrific, yeah, terrific. Richard does such a great job with this right. Dan: I mean, it's something that he's really doing it out of his own passionate curiosity himself. I think that's a good thing when you can make your own thing. I think that's a good thing when you can make your own. Dean: Then we did a week at Canyon Ranch in Tucson, which was really terrific and beautiful. I mean just gorgeous weather every day 75-ish. Got up to 80 a little bit, but absolutely clear. Not a cloud in the sky. For a week Didn't see a cloud in the night sky in Tucson. Dan: I was going to ask what's a day in the life at Canyon Ranch for you. Dean: I'll have a massage scheduled. You know you can go to 50 different things, but I don't. And you know, I read a lot while. I'm there I go for walks and know, did some gym work? and and then, yeah, just...
Duration:00:48:53
Ep145: Exploring Judicial Systems and Economic Models
2/12/2025
In this episode of Welcome to Cloudlandia, we explore how government assets could reshape public spending and economic growth. The discussion stems from Thomas Sowell's analysis of U.S. government land value. It extends to real-world examples of public-private partnerships, including Toronto's LCBO real estate deals and Chicago's parking meter agreement with a Saudi entity. Dan and I delve into the relationship between constitutional rights and entrepreneurship, drawing from my upcoming book. The American Bill of Rights creates unique conditions that foster business innovation and self-initiative, offering an interesting contrast to Canada's legal framework. This comparison opens up a broader discussion about judicial appointments and the role of government in supporting individual potential. The conversation shifts to the transformative impact of AI on content creation and decision-making. I share my experience with tools like Perplexity and Notebook LM, which are changing how we gather information and refine our writing. Integrating AI into daily workflows highlights the significant changes we can expect over the next quarter century. Looking ahead, We reflect on future podcast topics and the lessons learned from blending traditional insights with AI capabilities. This combination offers new perspectives on personal development and professional growth, suggesting exciting possibilities for how we'll work and create in the years ahead. 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: Yes indeed. I beat you by 10 seconds. Dean: I beat you by 10 seconds. Dan: Yeah, yeah. Dean: Well, there you go. That's a good way to end the year, right there. Dan: Yeah. Dean: Not that it's a contest. Dan: I was looking at an interesting article this morning from yesterday's Wall Street Journal by Thomas Sowell. I don't know if you know Thomas Sowell. No, yeah, he's probably the foremost conservative thinker in the United States. Okay, I think he's 90-ish, sort of around 90. He's been a professor at many universities and started off in his teenage years as a Marxist, as a lot of teenagers do, and before they learn how to count and and before they learn math the moment you learn math, you can't be a Marxist anymore and and anyway he writes and he just said how much all the land that the US government owns in the 50 states is equal to 1.4 trillion dollars. If you put a market value on it, it's 1.4 trillion dollars. I bet that's true wow and the problem is it costs them about that much money to maintain it, most of it for no reason at all. And he was just suggesting that, if Elon and Vivek are looking for a place to get some money and also stop spending, start with the property that the US government owns and sell it off. Dean: That's interesting I'm often Two things. Dan: Two things they get money coming in, yeah. And the other thing is they don't spend money maintaining it. Yeah, but it's 20, 25% of the land area of the US is actually owned, I guess owned, controlled by the US government. And you know there was a neat trick that was done here in Toronto and I don't think you'd be aware of it but the LCBO, liquor Control Board of Ontario. So in Ontario all the liquor is controlled by the government. The government is actually the LCBO is the largest importer of alcoholic beverages in the world. Dean: Wow. Dan: Nobody controls the amount of liquor well, and I. I just wonder if that's one of the reasons why you moved to Florida to get away from the government. Dean: Control of liquor they're a single payer, a single pay system. Dan: I just wondered if yeah, I just wondered if that on your list of besides nicer weather. Dean: I thought maybe you know being in control of your own liquor. I always found it funny that you could. You know you can buy alcohol and beer in...
Duration:01:01:55
Ep144: From Burnout to Breakthrough
2/5/2025
In this episode of Welcome to Cloudlandia, Dan and I explore how organizations can balance productivity with employee well-being through structured breaks and strategic planning. Dan shares insights from Strategic Coach's approach of giving employees six weeks off after three months of work, using Calgary's changing weather as a metaphor for workplace adaptability. Looking at the British Royal Navy's history, we discuss how its organizational structure relates to modern planning methods. Dean explains his 80/20 framework for yearly planning—using 80% for structured goals while keeping 20% open for unexpected opportunities, which helps teams stay focused while remaining flexible. The conversation turns to a long-term perspective through 25-year frameworks, examining how past achievements shape future goals. Dean shares a story about the Y2K panic to illustrate how technological changes influence our planning and adaptability. We conclude with practical applications of these concepts, from cross-training team members to implementing daily time management strategies. 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 thought I'd just give you a minute or two to get settled in the throne. Dean: Oh, you see, there you go. I'm all settled, All settled and ready. Good, it's a little bit chilly here, but not you know, not yeah it's a little bit chilly here too. Dan: Yeah, it's a little bit chilly here too. It just shows you there's different kinds of little bits. Dean: Different levels. Choose your chilly. Yeah, that's so funny, are you? Dan: in Toronto. It just brings up a thought that there are people who live in climates where 40 degrees below zero is not such a bad day. Dean: Yeah. Dan: And there are people who live in temperatures where it's 120, and that's not a too uncomfortable day. Dean: Right. Dan: So that's 160 degrees variation. If nothing else, it proves that humans are quite adaptable. I think you're right. I think you're absolutely right. Dean: That's what that shows. I use that example a lot when talking about climate change. We're very adaptable. Dan: Oh yeah, yeah, there is a place in. I looked this up because in Western Canada I think in the Denver area too, they have a thing called a Chinook, and I've actually experienced it. I used to go to Calgary a lot for coach workshops and I'd always, if it was like February, I'd always have to pack two complete sets of clothes, because one day it was 20 degrees Fahrenheit in the morning and it was 75 degrees Fahrenheit in the evening, the morning, and it was 75 degrees Fahrenheit in the evening, and then it stayed. And then it stayed that way for about two days and then it went back to, back to 20. And uh, this happens about, I would say, in Calgary, you know Alberta. Uh, this would happen maybe three or four times during the winter mm-hmm yeah, so so so there? Dean: well, there you go, so are you. Are you done with workshops therefore? Dan: yeah, yeah of strategic coach does the whole office closed down from the 20th and 20th of well yeah 20th was our party, so that was friday night. So we have a big in toronto. We have a big christmas party. You know, we have 80 or 90 of our team members and they bring their other, whatever their other is and not all of them, but a lot of them do and now we're closed down until the 6th, uh, 6th of january. That's great. Yeah, you know what? Dean: a lot of people that's 17 days, that's that's 17 days yeah that's a very interesting thing. Dan: So you know, it's like um so completely shut down as there's nobody in the office nobody, you know there's people who check packages like, okay, yeah, and they live right around the corner from the office, so they just go in and you know they check and, um, you know, and if, um, but no phone calls are being...
Duration:01:03:18
Ep143: Unveiling the Mysteries of Modern Media
1/29/2025
Today on Welcome to Cloudlandia, We start with the mysterious drone sightings over New Jersey, exploring the thin line between conspiracy and curiosity. These nocturnal aerial visitors become a metaphor for our complex modern world, where information and imagination intersect. We then investigate the profound impact of cultural icons like Mr. Beast and Kylie Jenner, examining how influence transcends traditional expertise. Our discussion reveals how public figures navigate changing landscapes of leadership and visibility, offering insights into the evolving dynamics of success and social capital. The episode concludes by challenging our approach to information consumption. Drawing from personal experiments and wisdom from thought leaders like Warren Buffett, we explore strategies for staying informed in a noisy digital ecosystem. Our conversation provides practical perspectives on navigating media, understanding cultural shifts, and maintaining perspective amid constant information flow. 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 are the drones looking down on you. Are the drones looking down on you. Dan: I mean, how many do you have up there? What is going? Dean: on with these drones. Dan: Yeah, I bet there's just a bunch of civilians fooling around with the government. Dean: Yeah, I wonder you know like you look at this. I think it's so. I wonder you know like you look at this. I think it's so amazing that you know we've had a theme, or I've been kind of thinking about this, with the. You know, is this the best time to be alive or the worst time to be alive? And I mentioned that I think probably in every practical way, this is the best time, but the anything in the worst time to be alive column just the speed and proliferation of, you know, conspiracies and misinformation and the battle for our minds. You know, keeping us in that. You know everything is just enough to be. You know where you're uncertain of stuff. You know there's a lot of uncertainty that's being laid out right now in every way. I mean, you look at just what's happened in the last. If we take 2020, fear you know. Dan: Well, tell me about it. I'm not very much of that 2024. Tell me about it. I experience very much of that. But why don't you tell me about that? Because I want to note some things down here. Dean: You know what? Dan: Every month, more money comes in than goes out. What more do you need to know besides that? Dean: I agree with you. I'm seeing the light here. It's just on the top level. We went through an election year which is always the you know the highly funded, you know misinformation campaigns or you know putting out there. So everybody's up on high level. Dan: Are you talking about lies Are? Dean: you talking about lies? Are you talking about lies? Who knows Dan? Dan: When I was growing up we called them lies. Why so many extra letters? I mean lies, that's a perfectly good Anglo-Saxon word. Why is Greek and Roman stuff in there? Dean: I think that's the thing, If we just simplify it. But if we bring it down to lies and truth, it's much more. Dan: I like lies and truth. Dean: Yeah, it's much more difficult to discern the lies from the truth. Dan: Yeah, he's telling a lie here, folks, his mouth is moving Exactly. Dean: You know that's the truth, but I just look at that. It's like you know the things that are. You know the things that are happening right now. Like you look at even with the government, even with the congressional hearings or announcements on, almost just like a matter of fact, oh yeah, there's aliens, there's totally aliens. There's. They've been here for a long time. We've got some in, we've got all the evidence and everything like that. But you know, carry on, it's just kind of so. It's so funny. Stuff is being like, you know,...
Duration:00:53:41
Ep142: From Childhood Snow to Cutting-Edge Networks
1/15/2025
In our latest episode of Welcome to Cloudlandia, we explore the remarkable growth of our coaching program, from its modest beginnings in 1994 to the bustling network of 18 associate coaches providing 600 coaching days annually. This evolution underscores the importance of adaptability and foresight as we hint at exciting expansion plans for 2026. Beyond the professional landscape, we delve into the nostalgic appeal of different climates and regional traditions. We compare the frigid allure of snowy winters with the sun-drenched charm of Florida and San Diego, offering a cozy reflection on why people choose to embrace extreme weather. Our conversation then turns towards the intricate dance of leadership and organizational structures. We explore the shift from rigid hierarchies to fluid, networked systems, imagining the profound changes in productivity that have paved the way for today's entrepreneurial landscape. From the global dominance of the US dollar to the speculative world of cryptocurrency, our discussion unveils the strategic significance of these economic elements, adding a light-hearted twist to our take on Canadian healthcare services. 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, mr Jackson, fresh from the frigid north, oh my goodness. Dan: Dan I you know. Yeah, I'm just happy to be back. It's sunny and warming. I'm going to say it's warm yet because it was only got up to like 6.3 or something yesterday, but it's warming up and it's warmer than it was. I did escape, without defaulting, my snow free millennium. I didn't get a cold this time, that's true. And I didn't get any snow on me, so that's good yeah. Dean: Well, we're actually in Chicago today and it's 49. Oh my goodness, wow, we're actually in Chicago today and that's 49. Oh my goodness, wow, it's deciding to see if it can upset Orlando, the area, a last valiant attempt before the total freeze sets in. Dan: Yeah, exactly. Dean: Exactly. Dan: Well, Dan, what a great couple of workshops we had this week. They were really I know about one of them, I know about one. Dean: That's actually a good thing to say. You know when you're developing a company. Dan: Absolutely yeah. Dean: I was telling people that in 1994, fifth year of the program, I did 144 workshop days that year and the reason being I was the only coach. So then in 95, we started adding associate coaches and we're up to 18 now. We just had our 18th one come on board. Come on board and this year the total coaching team will do 600 coaching days compared to 144 back in 1994 and I will do 12 of them. Dan: I was just gonna say yeah, 12. You got three groups times four, right yeah? Yeah yeah, that's great the connector. Dean: the connector calls which I, which I, which I absolutely love. I just think those two hour coaching calls are superb. Dan: I do too. Two hour zoom. Two hour zoom calls are the perfect. That's the perfect length. Anything more is too much. Dean: Yeah, so if you add those up, that would be using eight hours as a workshop day that would be 16 more days of coaching in a year, but that's significantly fewer than my 144. The problem with the 144, you didn't have much energy for creating new stuff, right? Dan: Yeah, and you were. Yeah, I guess that's true, right, and some of it you were having to. The good news about the position you're in right now is you really only do the same workshop three times, right, Like you do a quarterly workshop, but even that by the third time you've learned. Dean: Well they actually change. I mean they're probably 90%. In other words, number two is 90%, brings forward 90% of number one, and number three brings forward Because you've economized. You know I can do this quicker, I can do this. You add some new things, you get some new ideas. Dan: And you see what land is right, how...
Duration:00:51:47