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Welcome to Cloudlandia

Welcome to Cloudlandia

Von: Dean Jackson and Dan Sullivan
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 Join Dean Jackson and Dan Sullivan as they talk about growing your business and living you best life in Cloudlandia.© 2026 Welcome to Cloudlandia Marketing & Vertrieb Ökonomie
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  • Ep166: The Great Yesterdays

    Ep166: The Great Yesterdays
    Feb 18 2026
    The way you structure your time shapes everything else, including who else can reach you, and when. In this episode of Welcome to Cloudlandia, we get into two parallel time experiments that Dan and Dean are running, Dan's 70-day practice of using each day to "create a great yesterday," and Dean's intermittent phone fasting that divides the day into clear, protected zones. Dan traces the origin of his approach to a story from Leora Weinstein, who shifted his focus entirely from the uncertain future to building a reliable past, one day at a time. The result? His most productive December and January on record, and a measurable shift away from last-minute scrambling. They also explore how abundance, whether it's 14 kinds of corn flakes or an infinite choice of tasks, can paralyze decision-making rather than free it. The conversation moves through Dan's "Upping Your Game" tool (an evolution of the A/B/C model), AI bots taking on their creators' personalities, the surprising legal and real estate ripple effects of data centers, and a listener book recommendation about the history of money. Dan makes the case that the real cure for future anxiety isn't better planning, it's higher consciousness in the present. There's something almost game-like about committing to a better past each morning, and both Dan and Dean are finding that the scoreboard doesn't lie. This one's worth your time. SHOW HIGHLIGHTS Dan's 70-day "great yesterday" practice turned December and January into his most productive months ever.Dean's intermittent phone fasting from 10 PM to noon creates four protected daily zones for deeper focus.Future anxiety may simply be a symptom of low present consciousness, not a problem that better planning solves.Dan's upgraded "Upping Your Game" tool helps identify which activities to eliminate, tolerate, or expand and where AI can step in as the "who."An East German twin's paralysis in front of 14 varieties of cornflakes illustrates how abundance without criteria leads to retreat, not freedom.AI chatbots tend to reflect the personality of the person who created them, including their blind spots and biases. Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT (AI transcript provided as supporting material and may contain errors) Dean Jackson: Welcome to Cloud Landia, Mr. Sullivan. Hello there. There he is. From the West Coast. Dan Sullivan: Yes, I am straight Dean Jackson: To Cloud Landia. Cloud Landia is accessible from all points. Dan Sullivan: Yes, yes. But where you're sending from does make a difference. So I had a question for you. Dean Jackson: Tell me Dan Sullivan: From your experience, because you've had both, what's worse, 23 degrees Fahrenheit in Orlando, or minus 10 degrees in Toronto? Dean Jackson: Well, I will tell you this, that it came to the point last week that I actually had to wear pants one day. And so yeah, there's that, which I don't prefer, but today is a beautiful, we're right back now up to, let's see, it's 71 and sunny, probably similar to what you have right this moment. Dan Sullivan: Yeah, we're probably there. Yeah, the door is open. I'm looking out at, it's a nice place. I don't know if you've ever been here. Which one? La Jolla. Estancia. Dean Jackson: Yes. I've been to Estancia. Yeah, it's very Dan Sullivan: Nice. Nice place. Yeah. Yeah. We gotten in here just about this time yesterday, just a casual afternoon. Went to a really nice place, Maxima, who was with you last week? Maxima. And we went to an old hotel called the Empress Hotel. Dean Jackson: I know where that is. Dan Sullivan: Really nice restaurant. Dean Jackson: Oh, that's great. Dan Sullivan: Yeah, it's good. Dean Jackson: So the crowd is gathering. Dan Sullivan: I don't know if any of the clients are in yet. Our team just came in. I was sitting in the lobby. Lobby. And so half our team. Yes, Dean Jackson: Please. When is the actual, so you are in La Jolla, California for the Free Zone Summit, and that is on Tuesday is the actual day? Dan Sullivan: Well, it really starts Dean Jackson: Monday night. Dan Sullivan: Well, it starts Monday afternoon because Mike Kix is going to put on an AI from three to five o'clock. And then, Dean Jackson: Oh, there you go. Dan Sullivan: Then the Pacific Dean Jackson: Starts right in his backyard. Dan Sullivan: Yeah. Pretty well. Pretty well. And he's going to use one of our tools for part of his presentation. We have, I don't know if you remember an old tool. It was called the A BC model, and the A represented activities that you find really irritating. You hate them. Dan Sullivan: Yes. Dan Sullivan: And B represents okay activities that you don't hate them, you don't love them, you're just doing them more or less as a matter of habit. But it takes up your time and attention, and then they see as fascinating and motivating. And then you apportion what amount of time do you think you're spending on A and also B, and also C ...
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    58 Min.
  • Ep165: Creating Yesterday to Build Tomorrow

    Ep165: Creating Yesterday to Build Tomorrow
    Feb 11 2026
    In this episode of Welcome to Cloudlandia, we explore how changing fundamental time structures unlocks behavioral transformation that willpower alone can never achieve. Dean shares his 14-hour phone fasting experiment and the profound impact of creating inevitable constraints rather than relying on self-discipline. We discuss how raising decisions to the level of inevitability—physically locking your phone away—removes the constant negotiation with temptation. Dan introduces his new framework for productivity: making your purpose each day to create a great yesterday, shifting focus from anxiety-inducing future planning to confidence-building past accomplishment. We examine how AI accusations on social media reveal our default skepticism, why technology adds to life rather than eliminating existing solutions, and the critical difference between content and context in an AI-saturated world. The conversation moves through airport infrastructure decay, New York's political experiment, and why surgeons will always be humans using technology rather than replaced by it. This is a conversation about reclaiming attention, restructuring time, and recognizing that confidence comes from documented wins rather than optimistic projections. Whether you're struggling with digital distraction or seeking sustainable productivity systems, this episode offers practical frameworks grounded in real experimentation. SHOW HIGHLIGHTS Dean's 14-hour phone fasting creates inevitability through physical constraint, eliminating the need for willpower by making phone access impossible overnight.Dan's new productivity framework: "My purpose today is to create a great yesterday" shifts focus from future anxiety to past confidence.Behavioral change requires changing time structure first—Dan's 46-day experiment with creating great yesterdays eliminated his attention deficit entirely.Document accomplishments with "No did it" format to remind yourself what life would be like without each completed task.AI excels at content matching but struggles with context creation—the key differentiator for human creative and strategic thinking.Elon's management approach: weekly meetings asking "What did you accomplish?" interrogates the permanent record rather than optimistic future plans. Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT (AI transcript provided as supporting material and may contain errors) Dean Jackson: Mr. Sullivan. Dan Sullivan: Yes, Mr. Jackson. I wonder if our calls are being recorded in China. I just wonder. I hope so. I hope so. And transcribed and transcribed. I'd like to see one of our transcriptions in Chinese idiograms. That's it. Exactly. So are you just- I would get it framed and put it on a wall. Dean Jackson: Oh, that's perfect. Are you just getting up or are you still up from the big party last night? Dan Sullivan: No, we had massage. We have a massage therapist that we've had since 1992. 1992. She comes to our house on Sundays. Yeah. Dean Jackson: Oh, that's fantastic. Dan Sullivan: Yeah. Yeah. Yeah. Well, that's great. Dean Jackson: So how was- Dan Sullivan: We don't have the ideal climate that you enjoy at the Four Seasons. Valhalla. Valhalla. But we try to make up for it with other dimensions. Dean Jackson: That's right. The little built-in spa. Dan Sullivan: Yeah. Dean Jackson: Well, that's fantastic. So the party was a big success? Dan Sullivan: That was great. Dean Jackson: Yeah. Yeah. Had Bob's birthday party. Dan Sullivan: Yeah, it was great. Yeah, we had a restaurant. We took it over for ... Restaurants will have private parties and you take over the whole restaurant. And it's right at Front and Bay Street, just almost across from Union Station. And it's Peruvian Japanese fusion. Just shows you what people are putting together these days. And it was great. It was great. And our entire involvement was just showing up. Dean Jackson: Yes. I love that. That's the best. Dan Sullivan: Yeah. And Mark Young and his son were there and David Haase and Lindsay came. And Pete Warrell was here. He came ... Yeah. Richard and Lisa. Richard and Lisa were there. And so a lot of people traveled quite a distance to get there. So it was really great. Yeah. Dean Jackson: Absolutely. Oh, that's awesome. Yeah. I was texting with Richard Rossi yesterday. Dan Sullivan: After 12:00. After 12 o'clock noon. Dean Jackson: That's exactly right. Dan, I am a converse. Dan Sullivan: You're a new man. You're a new man. You're a new man. Dean Jackson: I am. I mean, this is a new normal. It's such a ... I'm realizing what a difference this phone fasting is. It's the best thing that I've ever done for productivity and just the ... I don't know. It's like the brain chemistry. I can feel it renewing. It's something like it's probably not unlike chronic inflammation from dopamine dripping constantly to the repairing of that from now the slow ... I'm manufacturing my own dopamine ...
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    1 Std. und 2 Min.
  • Ep164: AI, Employment, and the Future of Human Connection

    Ep164: AI, Employment, and the Future of Human Connection
    Jan 28 2026
    In this episode of Welcome to Cloudlandia, Dean and Dan explore the rapid transformation happening at the intersection of AI, work, and human relationships. Dean shares insights from an AI marketing conference where attendees split into two camps—those excited by technical possibilities and those overwhelmed by the pace of change. The key insight? Focus on the "what" and "who" rather than getting lost in the "how," treating AI as a tool that handles the backstage work while humans shine in front-stage interactions. The conversation takes a sobering turn as they examine how AI is fundamentally reshaping employment markets. Entry-level jobs are vanishing as companies choose AI over inexperienced workers, and the educational system continues training students for positions that may no longer exist. Dan shares a fascinating study showing how teachers' cognitive profiles have shifted dramatically toward fact-finding and rule-following—exactly the skills AI now replicates—while entrepreneurial thinking remains uniquely human. They discuss the growing value of authenticity in an increasingly automated world, from the appeal of live podcasts to the irreplaceable nature of genuine human hospitality. Dan shares his successful framework for using strategic thinking in political campaigns, demonstrating how human connection and listening remain the foundation of influence. The episode concludes with a powerful observation: as AI attempts to take center stage, the real response will be a return to valuing live, in-person human experiences more than ever. SHOW HIGHLIGHTS Why creatives should focus on making the milk and let others handle the farming—how AI frees you to do only what you do best.How AI is eliminating traditional first jobs and why the education system is preparing students for a future that no longer exists.Dan's theater approach to AI—automating predictable backstage work to make human front-stage interactions more valuable and authentic.How Ted Budd used Strategic Coach's Dangers, Opportunities, and Strengths framework to win a Senate seat, swinging the vote by 14 pointsWhy live podcasts and human hospitality are becoming more valuable as AI proliferates—people can detect "the thin clank of the counterfeit"s.Dean's evolved creative process using AI to handle everything except the actual thinking—writing five thoughts weekly with minimal friction. Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT (AI transcript provided as supporting material and may contain errors) Dean Jackson: Welcome to Cloudlandia. Mr. Sullivan. Hello there. There he is. How are you? Dan Sullivan: Good, good. Dean Jackson: There we go. Well, you are in Chicago now? Dan Sullivan: I'm in Chicago, yeah. Reasonably mild for this time of year. It's just a little bit above phrasing, still not too bad. Not too bad. Well, Dean Jackson: It's reasonably perfect here, just exactly at room temperature in the courtyard. Yeah. So there we go. You had a great week with the live 10 times talk podcast with Joe this week. That was good. Speaker 3: I think Dean Jackson: That there's a real pendulum swing right now in live, craving live and authentic and real stuff. It's a pretty interesting juxtaposition this week because I spoke at a conference on Monday and AI bought/marketing conference that Perry Belcher was holding in Orlando. So about 650 people there and it was just speaker after speaker sharing all the amazing things that are coming, that they're doing with generative AI and agentic AI, all the things. And we had a panel at the end of the day with all the speakers and I noticed two types of questions. It was open for Q&A. So people would come up to the mic and I noticed that there were technical people asking technical questions about the mechanics of how do you string together these syntax and using all this language of what the behind the scenes, the things that are making things happen. Dean Jackson: And then there were other people who came and were sort of like deer in headlights caught with feeling overwhelmed that they're in the wrong room, that they're so far behind, they'll never catch up. And it was really what struck me is it was, I said, the best thing if you're a creative person, a visionary in this, is the best thing you could really do is just pay attention to what they're doing, what's actually possible to get an idea of what the actual applications are and how you would see this working for you because that's what your strength is. And note who is doing these things and just focus on the what and the who and just completely bypass the how. Don't worry about how to do any of this. I said, this room is full of people who are ready and will do, which is see how it could apply. Dean Jackson: And that's a ... Dan Sullivan: I talked about about- Could you restate that? You blacked out for about five seconds there. Oh, Dean Jackson: Really? Okay. ...
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    52 Min.
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