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Welcome to Cloudlandia

Welcome to Cloudlandia

By: Dean Jackson and Dan Sullivan
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 Join Dean Jackson and Dan Sullivan as they talk about growing your business and living you best life in Cloudlandia.© 2025 Welcome to Cloudlandia Economics Marketing Marketing & Sales
Episodes
  • Ep157: Unveiling Toronto's Dual Identity

    Ep157: Unveiling Toronto's Dual Identity
    Jun 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 Dan and I explore the complexities of living in a "world-class" city like Toronto, discussing its cultural vibrancy against the backdrop of global geopolitical tensions.Dan delves into Toronto's significant role as a financial and technological hub, emphasizing its strategic importance in trade with the United States, where a substantial portion of Canadian exports cross the border.We discuss the transformative potential of AI in today's digital revolution, drawing parallels with historical innovations like Gutenberg's printing press, and how these advancements continuously redefine our society.We examine the evolution of Starbucks, from a unique third space with artisanal baristas to a more automated environment, and ponder the implications of this shift on quality and customer experience.The conversation shifts to the rise of independent coffee shops, highlighting how they meet the demands of discerning customers by offering premium experiences.Dean reflects on our relentless pursuit of convenience in modern urban life, where technological advancements shape our daily routines and enhance our quality of life.We conclude with a discussion on habit formation and the role of technology in reinforcing existing habits, while considering the balance between maintaining old routines and embracing new ones. 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: ...
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    46 mins
  • Ep156: Convenience Versus Tradition

    Ep156: Convenience Versus Tradition
    Jun 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 In this episode, we delve into Canada's evolving identity, sparked by significant events such as the King's visit and U.S. tariffs, which have prompted provinces to reevaluate internal trade barriers.Dan explores the challenges and comparisons between Canada and the U.S., particularly in areas like cannabis legalization and its broader implications on issues such as prison reform.We discuss the health concerns surrounding the rise of vaping, particularly its impact on youth, and how it is becoming a focal point in societal discussions.We navigate the transformative role of energy innovation and artificial intelligence, examining their impact on industries and economic power, particularly in the context of U.S. energy consumption.Dean shares personal experiences to illustrate AI's capabilities in reshaping information consumption, emphasizing technology as a powerful change agent.The intersection of technology and consumer behavior is dissected, with a focus on convenience trends, including the selective demand for electric vehicles and limousine services in luxurious locales.We conclude with a humorous anecdote about students using tape-recorded lectures, reflecting on the broader implications of convenience and technology in education. 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: ...
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    53 mins
  • Ep155: The Allure of AI in Real Estate and Beyond

    Ep155: The Allure of AI in Real Estate and Beyond
    May 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 In our recent trip to the UK, we experienced the unexpected warmth of London and engaged with the local culture, which included charming interactions with black cab drivers. This atmosphere set the tone for a successful event launch in Mayfair with global participants.We discussed the sparse historical records left by past civilizations, such as the Vikings, and how this impacts our understanding of history, drawing a parallel to the rich experiences of our recent travels.AI advancements, particularly Google Flow, are revolutionizing the creative landscape by democratizing filmmaking tools, allowing for lifelike scenes and interactions to be created easily and affordably.The potential of AI in the real estate market was explored, using the example of Lily Madden, an AI-driven persona in Portugal, which highlights the challenge of consumer attention in an ever-saturated digital content environment.We analyzed the Democratic Party's approach to media influencers in the 2024 election, noting the need for genuine engagement with voters' lives amidst fierce competition for attention in today's media landscape.The discussion shifted to aging and longevity, focusing on productivity and engagement in later years. We emphasized the importance of remaining active and contributing meaningfully past the age of 60.We wrapped up the episode with excitement about future projects, including a new workshop and book, highlighting our commitment to staying creatively engaged and inviting listeners to join us in future discussions. 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 ...
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    54 mins
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