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
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Episodes
  • Ep144: From Burnout to Breakthrough

    Ep144: From Burnout to Breakthrough
    Feb 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 We discuss the adaptability of humans to different climates, using Calgary's Chinook weather patterns as an example, and emphasize the importance of taking breaks to prevent burnout, citing Strategic Coach's policy of providing six weeks off after three months.Dean and I explore the planning strategies inspired by the golden age of the British Royal Navy, advocating for a structured year with 80% planning and 20% spontaneity to embrace life's unpredictability.Dan reflects on using 25-year frameworks to evaluate past achievements and future aspirations, noting that he has accomplished more between ages 70 to 80 than from birth to 70.We delve into the importance of discernment and invention, highlighting these skills as crucial for problem-solving and expressing creativity in today's world.Dean talks about sports salaries, noting how they reflect economic trends, and discusses the financial structure of sports franchises, particularly in relation to player salaries and revenue.We touch on government efficiency and cost-cutting measures, discussing figures like Elon Musk and Vivek Ramaswamy, and the impact of Argentina's President Milley.The conversation shifts to global trends and AI's role in the future workforce, noting the significance of recognizing patterns and making informed predictions about future technological advancements.Dean and I emphasize the importance of weekly and daily time management strategies, suggesting that structured planning can enhance both personal and professional effectiveness.Dan shares his year-end practices, including reflecting on past years and planning for the new year, while also noting his personal preference for staying home during the holidays to relax and recharge.We humorously recount historical events like the Y2K panic and discuss how technological shifts have historically reshaped industries and societal norms. 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 ...
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    1 hr and 3 mins
  • Ep143: Unveiling the Mysteries of Modern Media

    Ep143: Unveiling the Mysteries of Modern Media
    Jan 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 We explore the presence of drones over New Jersey, questioning whether they are linked to government surveillance or civilian activities, while considering the broader context of misinformation and conspiracy theories.Dan and I discuss the concept of anticipation being more stressful than actual experiences, suggesting it as a contributor to mental distress.The impact of cultural icons like Mr. Beast and Kylie Jenner is examined, highlighting their influence despite lacking traditional skills in their fields.We ponder on how cultural shifts are altering perceptions of corporate leadership, using a hypothetical scenario of a CEO's public safety being compromised.The dynamics of news consumption are analyzed, contrasting real-time news feeds with curated platforms like RealClear Politics to understand how they balance diverse political viewpoints.I share my experience with digital abstinence, noting the benefits of reduced distractions and the negligible impact of disconnecting from the continuous news cycle temporarily.The concept of "irrational confidence" is explored, discussing how it characterizes overachievers and can be cultivated over time to foster personal growth.We reflect on long-term investment strategies inspired by Warren Buffett, emphasizing the enduring need for certain products and industries.I consider the importance of balancing cultural awareness with the need to filter out unnecessary noise, contemplating changes in my information consumption habits.Insights from personal experiments in digital and media consumption are shared, emphasizing the importance of distinguishing between transient cultural information and lasting knowledge. 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 ...
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    54 mins
  • Ep142: From Childhood Snow to Cutting-Edge Networks

    Ep142: From Childhood Snow to Cutting-Edge Networks
    Jan 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 We discussed the remarkable evolution of our coaching program, starting from 1994 with 144 workshops conducted solely by me, to a network of 18 associate coaches delivering 600 coaching days annually.Dean shares his experiences from the icy north and reflected on the gradual adaptation to warmer climates, providing insights into the unique economic opportunities that arise from natural challenges.We explored the nostalgic memories of childhood winters, contrasting them with the warm climates of Florida and San Diego, and discussed the cultural differences in regional terminology.The episode delved into the shift from rigid hierarchical structures to more fluid, networked systems, highlighting the transformative impact of technology on productivity and organizational dynamics.We imagined the productivity revolution that could have occurred if a writer in the 1970s had access to a modern MacBook, pondering the implications for decision-making and strategic planning.The conversation touched on the global dominance of the US dollar as the world's reserve currency, and the minimal impact of foreign trade on the US economy compared to other export-driven nations.We questioned the viability of Bitcoin as a true currency due to its lack of fungibility compared to the US dollar, and discussed gold's role as a hedge against currency inflation.The episode highlighted the Canadian dollar's strategic role as a financial hedge, particularly in relation to tax burdens and global business ventures.We examined the concept of "sunk cost payoffs," encouraging reflections on optimizing investments in fixed costs to achieve greater returns through training and education.The episode concluded with a light-hearted discussion on Canadian healthcare services, and the humorous notion of using Chicago as a secondary tier for healthcare needs. 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...
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    52 mins

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