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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.

  1. Ep166: The Great Yesterdays

    4H AGO

    Ep166: The Great Yesterdays

    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 right now, and then a year from now, where would you want your time allocation? But I changed it, upgraded it, and it's called Upping Your Game. And then you brainstorm for each of the three categories, and then you talk about the top three changes you're going to make with a top three for B and top three with C. And then Mike's going to show how that relates to ai, where AI is the who. Oh, I like that. Yeah. Yeah. So Dean Jackson: I like that. I mean, yeah, that's great. I always had to mix in my mind, we're used to A being the good thing and C being the less than thing. So I had to always flip that in my mind that the C is actually the good thing in this model, but the sentiment of it I love, and it's similar. It's like you could overlay the unique ability, unique ability, and the things you you're excellent at and the things you're, Dan Sullivan: And in some ways, that's almost the essence of coach. And so it's been a couple, it's simple, but not necessarily easy. Dean Jackson: That's the truth. That is the truth. Dan Sullivan: Simple. But not necessarily could be easy, but not necessarily. Dean Jackson: Yeah, it's easy. Yeah. It's nice when you look at it just to be crystal clear, right? That fits with your, I've been using your model of is there any way for me to get this result without doing anything? That would be the A plus for me of these. Right? And then, yeah, what's the least amount Dan Sullivan: That I, that's a model that's a little closer to where I am right now, that the a c model, I think the A, b, C model is about 15 years old. And the question, the three questions, I think is about two years. So one of them is repair of the past. The other one is it's sort of I'm not going to do anything in the future. Right, right, right. Yeah. I'm going to expand and grow and jump without me doing anything at all. Dean Jackson: That's even better with your mind. With your mind, yes. Prompting. But I think that's the magic of that is knowing what you want, knowing that this is what I want, but is there any way for me to get it without doing anything? I think that's fantastic. So Max was here in Orlando at Celebration last week. We had a breakthrough blueprint, and we actually, we had about a half size group. We lost people that were stranded in North Carolina, the freeze in New Jersey, the deep freeze or whatever. One of they showed me it was a hundred car pile up in Charlotte, a hundred car pile up. I mean, you could see that's like the ice. Everybody's sliding into each other. That's kind of crazy. I don't prefer it. Every time that kind of stuff happens, it makes me more resolute in my snow free millennium Dan Sullivan: Commitment. Dean Jackson: I'm quite enjoying that. That's the right way to do it. Dan Sullivan: Yeah. Well, I think people are really built differently, but I so love the change of seasons that I wouldn't be tempted like La Jolla here. I mean, there isn't much here that would give you the kind of resistance that you would actually develop character. Dean Jackson: Well, the only thing Dan would be the traffic. The traffic trying to get out of La Jolla at any time in rush hour. But other than that, you don't have to leave La Jolla or get into it. It's perfection. Yeah, Dan Sullivan: I, I don't feel any of Newton's third law here, third law for every action, there's an opposite and equal. I'm just not getting the equal reaction here. It's just all easy. I mean, how can you develop character when everything's Dean Jackson: Just, well, you have to develop. What you have to do is develop the character in order to get to be there. That's the real thing. Somebody said that San Diego, especially LA and the coastal areas have gotten unreachable for average Americans or the things, and it's like my first thought was, well try harder. I mean, that's not, LA Jolla doesn't owe anybody anything to be affordable. Why Dan Sullivan: Now would you count $40 for bagel and Lve? Exactly. Choice. That was my choice. This morning. I said, I'd like to have the bagel and locks, Dan Sullivan: And Dan Sullivan: They said, well, it's a buffet. You can put together your own bagel and locks. But what if I just want the bagel and locks? Dan Sullivan: Doesn't matter Dan Sullivan: How much is, well, first of all, how much is the buffet? It's $40. And I says, well, what if I just want the bagel and Lux? It's 40. Dean Jackson: Right, exactly. Dan Sullivan: And it's not even bagel, it's actually Bagel Crisps. So they've taken a bagel and they've cut it into 10 pieces and crisp it. Dean Jackson: Okay. Dan Sullivan: But it's actually quite good. It's actually Dean Jackson: Good Melba toast in a way. Dan Sullivan: Yeah. It's like Melba toast, but it's bagel. It's got a nice taste to it. So I had five of them. I had five of them Dean Jackson: Get your money's worth. Dan Sullivan: I wasn't heavy on the locks. I had a big let or whatever they call 'em, a crisp. I had one of those. And

    58 min
  2. Ep165: Creating Yesterday to Build Tomorrow

    FEB 11

    Ep165: Creating Yesterday to Build Tomorrow

    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 by really getting into my own brain. Dan Sullivan: Yeah. It's really interesting. I mean, over the years, because I've been continually creating thinking tools for entrepreneurs to look at things from a different perspective. But my feeling is that you can't make other behavioral changes unless you change a time structure, that there has to be a fundamental change of a time structure. And if you change a time structure, then all sorts of things can happen just because of that fact. And you've changed a 14 hour time structure in your life. Dean Jackson: Yeah. Give me some other examples because that's the first time I've heard you say that. So when you say the changing the time structures, what- Dan Sullivan: Yeah. Well, a simple example would just be that you have three different kinds of days. You have free days days and buffer days. And that immediately changes how you'd get work done. It changes what was sort of an off day. People say, "Yeah, well, I'm taking a day off." But in fact, they did business on their day off. I used to give this example. I said, everybody probably has come across the concept of Neapolitan ice cream. They used to come in the square package Dean Jackson: And then Dan Sullivan: You- Dean Jackson: Yeah, it's one of my favorites. Yeah. Dan Sullivan: And then if you took the cardboard away that protected, it was just this beautiful block. There was chocolate, vanilla, and strawberry. And then for some reason you forgot about it and you went away for three or four hours and you came back and it was just neopolitan soup. And which turns out to be chocolate. All things default to chocolate. Like if strawberry and vanilla and chocolate melt, what you have is a lighter shade of chocolate. Dean Jackson: Okay. That's interesting. Dan Sullivan: And everything gets mixed up with everything else and there's no structure, there's no distinction among your days. And I think you don't get rejuvenated. You're not very productive. And I just think everything falls apart when you mix different kinds of time structure, but you've created a very fundamental 14 hour structure right in from the end of one day to the middle of the next day. And so your brain just reorganizes everything just because you created that structure. Dean Jackson: Yes. I'm noticing it for sure. And yeah, it's a profound change. So I'm very excited about that. That's a good progress. Like that's one of my main things that I see looking at. What I've discovered in that, in reflecting on it, like why that works so well is that I've raised it to the level of inevitability. And we talk about that as like the apex ... That's the apex predator of certainty, is that when I put my phone in the lockbox, I've created an environment where it's inevitable that I'm not going to look at my phone for 14 hours because I can't. It's physically not possible for me to look at my phone because it's in the box. So I've eliminated the option, no willpower required. Like if I brought it and I put it in my bag and I went to the cafe or I went to whatever I'm sitting in the courtyard here and I had the phone inside the door in another room, there's still the siren song of the promise of dopamine or the fear of missing out or the something would draw me inevitably to check the phone and then you've reset the ... Dan Sullivan: A growling or a whimpering dog Dean Jackson: In Dan Sullivan: The next room. Dean Jackson: Yep. Dan Sullivan: Yeah. Dean Jackson: That's exactly right. Dan Sullivan: And you can't concentrate on anything else because it's drawing your attention. Yeah. Dean Jackson: Yeah. Dan Sullivan: Yeah. And maybe I could just look for five minutes, maybe Dean Jackson: .That's what I say. You start rationalizing, right? Yeah. Dan Sullivan: Yeah. Dean Jackson: You start rationalizing and negotiating the things. There's something to it because I was overlaying that with the thought of creating a better past and that- Dan Sullivan: So I've got a question for you and this is a big idea that I'm presenting. What if tomorrow the whole world decided to do what you're doing and that- How great would that be? No, but what would happen to the world economy? Dean Jackson: I wonder. I wonder. I mean, I guess it would ruin my breakfast plans. What? If I couldn't go to Honeycomb and get breakfast, if everybody else is closed. No, Dan Sullivan: Not closed. Their phone was off for breaking hours. Oh, I think that's it. Not that they weren't doing everything else, it's just that they're phone. Oh, got it. What do you think? Dean Jackson: I mean, I think it would be- It Dan Sullivan: Would certainly change online marketing. Dean Jackson: Yeah, absolutely it would. But I think that then people would ... I think it just condenses it. I look at the first thing, within 10 minutes of turning on my phone, by 12:10, I'm completely caught up on anything that I missed. First of all, I check my text messages. That's the thing that you'll see

    1h 2m
  3. Ep164: AI, Employment, and the Future of Human Connection

    JAN 28

    Ep164: AI, Employment, and the Future of Human Connection

    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 points Why 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. So Dan Sullivan: We didn't. It's what you said, the room is filled with people who know the how. You don't have to worry about the how. Dean Jackson: Yeah, that's exactly right. And I said, the thing is that I talked about the self-milking cow, that the biggest frustration is that sometimes the creatives are worrying about having to be a self-milking cow where they have to milk themselves and pasteurize it and package it and take it to market, all the things. Where if you just focus on making the milk, you can surround yourself by farmers and do all of that other stuff and just free yourself to be a cow. It was funny to see just the shoulders relax and you could hear the collective for those people, for the people in the room that were in that situation. Dan Sullivan: Yeah. Yeah. I've had the same experience talking to strategic coach clients. And I have it in the workshops, but not so much because the people in the workshops are there to think about their thinking about what they've been doing and what they're doing next. But when I'm in a more social setting, and in my case, it would be when I'm in one of our two main offices, Toronto or Chicago, and it's lunchtime and there are other coaches coaching the client. Then at lunchtime, I'm in the cafe and as many as eight or nine other people will come and join me for lunch. But the last three times that I did that, that was probably in December. The entire topic for the entire lunchtime hour was AI, which is interesting. I mean, to compare it a year back, it wouldn't have been that way a year ago. Dan Sullivan: So it's a topic that's grown in importance over the last year. And one of the groups was a first year group. They were just in their first year of strategic coach. And a woman asked me, she said, "How are you looking at this? " And I said, "Well, I take a theater approach to entrepreneurism, and that is that there's a backstage and there's a front stage." And I said that, "I think that what AI is allowing us to do is to increase the automation in the backstage so that we can make the front stage more and more human." So it's actually freeing humans up to be in the front stage and because there's so much that AI does, which is sort of predictable and repetitive work that's now using up the time and effort of backstage people and so we can free them up. So we put our emphasis on the interaction of engaging with people and that's largely unpredictable. Dan Sullivan: So unpredictable front stage, more predictable backstage. So that's been my approach to it so far. And it seems, first of all, it also has that relaxing impact that you talked about. I mean, it is amazing, but if everything's amazing, it stops being amazing. Dean Jackson: I think you're right. And the question I've been asking now, whenever I see these things or I hear people talking about their rather ... And people take pride in the way they've strung together all these agentic bots doing these complex workflows of things. But the question I've been asking both to myself and to them is to what end? That's the thing is I always have to think like, to what end is this? What is the outcome that we're attaching this to? Because a lot of it's just activity for activity's sake, content for content's sake, without really understanding like, how is this making the boat go faster? Is it improving the ability to get a result? And it's a very interesting thing when you work backwards from the outcome that you're looking for, as opposed to just working at the workflow. Everybody immediately assumes that more content is better and that more having ... I've noticed that the proliferation of clones, that's the big thing now, setting up your AI clone to create these videos for almost you. Dean Jackson: As Jerry Spence would say, we can all detect the thin clank of the counterfeit. And so it's not exactly as ... If you've got the chance to watch or to give your real life attention units to something that is not authentic, or you can be on a live 10 times talk podcast with you and Joe where you know 100% that it's real and it's you guys and there's like a real gathering of humans. There's a different energy to it. Dan Sullivan: Yeah. Yeah. I get that feeling. And the other thing for the people who are straining things together right now in January of 2026, how's it going to be any different in 2027? They're still going to be straining new things together, but have they produced everything to be different- Have they produced any breakthrough impact by their straining things together? Dean Jackson: Yeah. What's the result? That's the exact, that's the thing. That's what I always look at is that, to what end is this going to actually make a difference? I shared with you my new ... The process now of creating my five new thoughts a week of brainstorming the ... Today is come up with the idea day, and then through the week I'll write the five thoughts. An

    52 min
  4. Ep163: The Phone-in-the-Box Experiment and the Speed of Truth

    JAN 21

    Ep163: The Phone-in-the-Box Experiment and the Speed of Truth

    In this episode of Welcome to Cloudlandia, Dan and Dean explore the intersection of personal transformation and rapid global change in our technology-driven world. Dean reveals the profound results of his eight-week phone-in-the-box experiment, sharing how reclaiming 14 hours daily has restored his ability to read for extended periods and revolutionized his creative process. He discusses developing systematic approaches to manage ADHD, including mastering 50-minute focus sessions that consistently produce two fully-formed thought pieces. With Charlotte, his AI partner who can read his handwriting, Dean has created a sustainable rhythm for generating hundreds of insights annually. Dan shares unexpected breakthroughs from his stem cell treatments—while the 50-year-old knee injury heals slowly, his cognitive testing has improved 90% and his reflexes have returned to levels he hasn't experienced in decades. He discusses upcoming book launches, including The Greater Game with John Bowen, featuring original entrepreneurial research and interactive dashboards, plus the innovative four-by-four casting tool being developed as their first licensed internet product. The conversation shifts to examining how individual action amplified by technology can expose truth at remarkable speed. From Venezuela's Maduro being extracted to a Brooklyn jail cell to a lone citizen journalist uncovering $112 million in daycare fraud with just his phone and one day of investigation, we explore how Cloudlandia enables rapid revelation of hidden realities. We close by reflecting on the philosophical nature of AI use—how billions of people are each creating entirely unique cognitive signatures with their AI tools, as distinctive as fingerprints yet largely invisible to the world. It's a fascinating look at how technology simultaneously democratizes capability while making individual creative processes more private than ever. SHOW HIGHLIGHTS Dean shares eight weeks of results from his daily experiment, revealing how eliminating phone access for 14 hours has fundamentally restored his ability to focus, dramatically improved his sleep scores, and brought back the hours-long reading sessions he thought he'd lost forever.. Dan reveals the surprising results from eight stem cell treatments—while his 50-year-old knee injury progresses slowly, his brain health has skyrocketed with 90% improvement in cognitive testing. The remarkable story of Venezuela's Maduro—executed flawlessly in 30 minutes by Delta Force with 120 planes, no American casualties, and no equipment left behind. Dan's theory that if you interviewed half the world's population, you'd find four billion people working on four billion different things with AI—each creating cognitive signatures as unique as fingerprints, largely undetectable and fundamentally private despite the connected world we inhabit. Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT (AI transcript provided as supporting material and may contain errors) Dean Jackson: Welcome to Cloudlandia. Dan Sullivan: Mr. Jackson. How are you? Good, good. Had a great trip to London for- Dean Jackson: I didn't know you were going to London. Dan Sullivan: Yeah. Yeah. We just decided at the last moment, unfortunately, we got good flights and good rooms and some friends of ours from the DC area, they went and Steven Palter and his family were there. Oh, Dean Jackson: Nice. Dan Sullivan: So lots of great meals, lots of great place. Two out of three, which is good batting average. That gets you into Hall of Fame if you get two out of three. Exactly. Actually, if you get three out of 10, you've got a good chance. Dean Jackson: That's right. Dan Sullivan: If you play 20 years and have a 300 batting average, probably you're in consideration depending on Dean Jackson: Venture capital. Dan Sullivan: When the hits actually happened. Dean Jackson: Yeah. I got Babs texted on New Year's Eve and you guys were back from ... I didn't realize you were gone. Were you there for Christmas or after Christmas you went? Dan Sullivan: Yeah, we left on Christmas day night and flew overnight to London. And then boy, it was buzzing. London downtown doesn't matter what day it is, it's buzzing. Yeah. I just saw a video last night and it's one of these new AI films, which I think is really great where they'll take a sketch that was made of London 2000 years ago and then they'll animate it. And Speaker 3: It's Dan Sullivan: Really terrific. It's really terrific. For history buffs, it's terrific. I think this AI thing has uses. What do you think? I mean, are you noticing things that you wish you could have done five years ago more quickly? They're happening more quickly. Dean Jackson: Yeah. I'm working today on creating a better past. And the better past involves AI. Yeah. That's a really interesting thing. I watched over Christmas, there's a new series called Pluribus. Dan Sullivan: You described it on a previous session. Dean Jackson: Yeah. I was just fascinated. It wrapped up Christmas Eve. Dan Sullivan: What is it? A final six or a final 12? What's the numbers of humans? Dean Jackson: Oh yeah, there was 12 humans that were- Weren't taken Dan Sullivan: Over. We're not taking over. Dean Jackson: In the joining. I thought what a really interesting ... Dan Sullivan: In my lifetime, I've discovered about five of them. You're one of them. Dean Jackson: Okay. Yeah. The interesting thing is it was a really interesting ... If you think about the joining the many at Pluribus as the physical embodiment of AI, the large language model, that was what was very interesting. What I found really was that one of the 12, one of the people who was unaffected by it very quickly learned on that anything is possible. And so they were Carol, the lead character, she summoned ... The many are responsible for delivering whatever Carol wants kind of thing. They're at her service. And so she arranges a meeting. She wants to meet the 12. And so they set it up for South of France or somewhere. And one of the gentlemen realized that he has access to everything. So he insisted on being flown on Air Force One, that that's available to him, that whatever is available is available to you. And I thought it was a really interesting thing of how some people put limits on themselves, even when everything is available to you. That this guy was thinking without limits, like, "What's the thing? I want Air Force One to come and why me to meet with them." And it was really ... I thought it's the same. It's very interesting to see Dan Sullivan: How- So are they immortal too? Dean Jackson: That's a great question. I don't know that whether they're immortal, but ... Dan Sullivan: Yeah, because if not, then they're limited by time. Dean Jackson: Yeah. It's unclear to me right now whether they are immortal. Dan Sullivan: Well, you can only push a plat so far. It's like metaphors. Metaphors are very useful up to a point. Yeah. Yeah. Dean Jackson: Unless you're a self-miller. Dan Sullivan: I mean, is it driving them crazy or what's happening to Dean Jackson: Them? Well, it's very ... So Carol is set on undoing the joining because she feels that everybody has this right to be an individual with their own autonomy and agency and whatever it is, rather than just blending in and becoming the group mind. And so there's another gentleman from Ecuador or somewhere in some Spanish speaking he is, and he Dan Sullivan: Wants to- Not Venezuela. Dean Jackson: Not Venezuela. He wants to do the same thing. No, not Venezuela, luckily. Dan Sullivan: Yeah. Yeah. Yeah. Yeah, because Nicholas Maduro's ... Things were just normal on Saturday and on Brooklyn. And then 24 hours later, he was in a jail cell in Brooklyn. And I mean, that's quite a shift in one day. Dean Jackson: So tell me the ... I know all those words that you just said, but I don't know the actual ... Can you give me the synopsis of- Dan Sullivan: Well, it would happen when your phone was in the box. Dean Jackson: Yeah. Dan Sullivan: Yeah. Yeah. First of all. Dean Jackson: Overnight. Dan Sullivan: So Trump couldn't call you to let you know because check your back calls. Maybe Trump maybe Trump dropped a call. Yeah. In 30 minutes, they got in and got out. They went in and they found him and his wife in his bedroom and they packed him up and brought him by helicopter to a carrier in the Mediterranean ... Not Mediterranean, in the Caribbean. And then they flew him to New York and he's now in a jail cell in Brooklyn. Yeah, the two of them. Yeah. Yeah. And that's because he said he wouldn't stop sending drugs to the United States. Dean Jackson: Okay. Okay. Dan Sullivan: They brought him to the United States. Dean Jackson: Okay. There you go. Dan Sullivan: Yeah. Dean Jackson: And how do people in Venezuela feel about that? Dan Sullivan: Apparently there are celebrations all over. I mean, first of all, there's two types of people in Venezuela, those who are joyous and celebrating, and those who are confused and pissed off. And I mean, you never get complete consensus on something like this. And so anyway, it's apparently really well planned, really well executed and really well. No American lives lost, no equipment left behind. They went in with 120 planes, knocked out all the power and Karakas, knew exactly where to go, flew in. Now, there's no report of casualties. I suspect there's some casualties because he had Cuban security pretty troops because Cuba depends upon Venzauela for its oil. And so that stopped about two weeks ago. They stopped the oil to Vince or to Cuba just by stopping the ships and now just decided that to move things forward, they just put him in a jail cell in Brooklyn and then see how the negotiations go after that. Dean Jackson: Wow. And now, so that will affect the South American stuff. Wasn't he the nexus for funding? Speaker 3: Yeah.

    58 min
  5. Ep162: Why Creating Value First Changes Everything

    JAN 14

    Ep162: Why Creating Value First Changes Everything

    In this episode of Welcome to Cloudlandia, we explore how Miles Copeland, manager of The Police, turned Sting's unmarketable song "Desert Rose" into a 28-million-dollar advertising campaign without spending a dime. The story reveals a powerful principle most businesses miss—the difference between approaching companies at the purchasing department versus the receiving dock. Dan introduces his concept that successful entrepreneurs make two fundamental decisions: they're responsible for their own financial security, and they create value before expecting opportunity. This "receiving dock" mentality—showing up with completed value rather than asking for money upfront—changes everything about how business gets done. We also explore how AI is accelerating adaptation to change, using tariff policies as an unexpected example of how quickly markets and entire provinces can adjust when forced to. We discuss the future of pharmaceutical TV advertising, why Canada's interprovincial trade barriers fell in 60 days, and touch on everything from the benefits of mandatory service to Gavin Newsom's 2028 positioning. Throughout, Charlotte (my AI assistant) makes guest appearances, instantly answering our curiosities. SHOW HIGHLIGHTS How Miles Copeland got $28M in free advertising for Sting by giving Jaguar a music video instead of asking for payment. Why approaching the "receiving dock" with completed value beats going to the "purchasing department" with requests. Dan's two fundamental entrepreneur decisions: take responsibility for your financial security and create value before expecting opportunity. How AI is accelerating adaptation, from tariff responses to Canada eliminating interprovincial trade barriers in 60 days. Why pharmaceutical advertising might disappear from television in 3-4 years and what it means for the industry. Charlotte the AI making guest appearances as the ultimate conversation tiebreaker and Google bypass. Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT (AI transcript provided as supporting material and may contain errors) Dean Jackson: Mr. Sullivan, Dan Sullivan: Good morning. Good morning. Dean Jackson: Good morning. Good morning. Our best to you this morning. Boy, you haven't heard that in a long time, have you? Dan Sullivan: Yeah. What was that? Dean Jackson: KE double LO Double G, Kellogg's. Best to you. Dan Sullivan: There you go. Dean Jackson: Yes, Dan Sullivan: There you go. Dean Jackson: I thought you might enjoy that as Dan Sullivan: An admin, the advertise. I bet everybody who created that is dead. Dean Jackson: I think you're probably right. Dan Sullivan: Yeah. I was just noticing that. Jaguar, did you follow the Jaguar brand change? Dean Jackson: No. What happened just recently? Dan Sullivan: Yeah. Basically maybe 24. They decided to completely rebrand. Since the rebranding, they've sold almost no cars and they fired their marketing. That's problem. Problem. Yeah. You can look it up on YouTube. There's about 25 P mode autopsies. Dean Jackson: Wow. Dan Sullivan: Where Dean Jackson: People are talking mean must. It's true. Because they haven't, there's nothing. It's pretty amazing, actually, when you think about it. The only thing, the evidence that you have that Jaguar even exists is when you see the Waymo taxis in Phoenix. Dan Sullivan: Is that Jaguar? Dean Jackson: They're Jaguars. Yeah. Dan Sullivan: I didn't know that. Yeah. Well, yeah, they just decided that they needed an upgrade. They needed to bring it into the 21st century. Couldn't have any of that traditional British, that traditional British snobby sort of thing. So yeah, when they first, they brought out this, I can't even say it was a commercial, because it wasn't clear that they were selling anything, but they had all these androgynous figures. You couldn't quite tell what their gender was. And they're dressed up in sort of electric colors, electric greens and reds, and not entirely clear what they were doing. Not entirely clear what they were trying to create, not were they selling something, didn't really know this. But not only are they, and then they brought out a new electric car, an ev. This was all for the sake of reading out their, and people said, nothing new here. Nothing new here. Not particularly interesting. Has none of the no relationship to the classic Jaguar look and everything. And as a result of that, not only are they not selling the new EV car, they're not selling any of their other models either. Dean Jackson: I can't even remember the last time you saw it. Betsy Vaughn, who runs our 90 minute book team, she has one of those Jaguar SUV things like the Waymo one. She is the last one I've seen in the wild. But my memory of Jaguar has always, in the nineties and the early two thousands, Jaguar was always distinct. You could always tell something was a Jaguar and you could never tell what year it was. I mean, it was always unique and you could tell it wasn't the latest model because they look kind of distinctly timeless. And that was something that was really, and even the color palettes of them were different. I think about that green that they had. And interesting story about Jaguar, because I listened to a podcast called How I Built This, and they had one of my, I would say this is one of my top five podcasts ever that I've listened to is an interview with Miles Copeland, who was the manager of the police, the band. And in the seventies when the police were just getting started, miles, who was the brother of Stuart Copeland, the drummer for the police. He was their manager, and he was new to managing. He was new to the business. He only got in it because his brother was in the band, and they needed a manager. So he took over. But he was very, very smart about the things that he did. He mentioned that he realized on reflection that the number one job of a manager is to make sure that people know your band exists. And then he thought, well, that's true. But there are people, it's more important that the 400 event bookers in the UK know that my band exists. And he started a magazine that only was distributed to the 400 Bookers. It looked like a regular magazine, but he only distributed it to 400 people. And it was like the big, that awareness for them. But I'll tell you that story, just to tell you that in the early two thousands when Sting was a solo artist, and he had launched a new album, and the first song on the album was a song called Desert Rose, which started out with a Arabic. It was collaboration with an Arabic singer. So the song starts out with this Arabic voice singing Arabic, an Arabic cry sort of thing. And this was right in the fall of 2001. And Speaker 1: Yeah, that's a good, Dean Jackson: They could not get any airplay on radio airplay. You couldn't get American airplay of a song that starts out with an Arabic wailing Arabic language. And so they shot a video for this song with Chebe was the guy, the Che Mumbai, I guess is the singer. So they shot a video and they were just driving through the desert between Palm Springs and Las Vegas, and they used the brand new Jaguar that had just been released, and it was really like a stunning car. It was a beautiful car that was, I think, peak Jaguar. And when Miles saw the video, he said, that's a beautiful car. And they saw the whole video. He thought you guys just made a car commercial. And he went to Jaguar and said, Hey, we just shot this video, and it's a beautiful, highlights your car, and if you want to use it in advertising, I'll give you the video. If you can make the ad look like it's an ad for Sting's new album. I can't get airplay on it now. So Jaguar looked at it. He went to the ad agency that was running Jaguar, and they loved it, loved the idea, and they came back to Miles and said, we'd love it. Here's what we edited. Here's what we did. And it looks like a music video. But kids, when was basically kids dream of being rock stars, and what do rock stars dream of? And they dream of Jaguars, right? And it was this, all the while playing this song, which looked like a music video with the thing in the corner saying from the new album, A Brand New Day by Sting. And so it looked like a music video for Sting, and they showed him an ad schedule that they were going to purchase 28 million of advertising with this. They were going to back it with a 28 million ad spend. And so he got 28 million of advertising for Stings album for free by giving them the video. And I thought, man, that is so, it was brilliant. Lucky, lucky. It was a VCR. Yeah. Lucky, Dan Sullivan: Lucky, lucky. Dean Jackson: It was a VCR collaboration. Perfectly executed. Dan Sullivan: Yeah. Yeah. It just shows that looking backwards capability, what I can say something that was just lucky looks like capability. Dean Jackson: Yeah, the whole, Dan Sullivan: I mean, basically it saved their ass. Dean Jackson: It saved Sting and Yeah. Oh yeah. But I think when you look in the, Dan Sullivan: No, it was just lucky. It was just lucky. I mean, if there hadn't been nine 11, there's no saying. There's no saying it would've gone anywhere. Dean Jackson: Right, exactly. Dan Sullivan: Well, the album would've gone, I mean, stain was famous. Speaker 1: It would've Dan Sullivan: Gone, but they probably, no, it's just a really, really good example of being really quick on your feet when something, Dean Jackson: I think, because there's other examples of things that he did that would lead me to believe it was more strategic than luck. He went to the record label, and the record label said, he said he was going to give the video to Jaguar, and they said, you're supposed to get money for licensing these things. And then he showed them the ad table that the media buy that they were willing to put behind it. And he said, oh, well, if you can match, you give me 28 million of promotion for the album, I'll go b

    53 min
  6. When AI Becomes Your Thinking Partner

    08/27/2025

    When AI Becomes Your Thinking Partner

    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 Dan reduces his book chapter creation time from 150 to 45 minutes using AI while maintaining complete creative control Only 1-2% of the global population actively uses AI for creative and profitable work despite widespread availability Nuclear power emerges as the only viable energy solution for AI expansion, with one gram of uranium equaling 27 tons of coal Most human conversations follow predictable large language model patterns, making AI conversations surprisingly refreshing Dean's personalized AI assistant Charlotte acts as a curiosity multiplier but has no independent interests when not in use 40% of future AI capacity will be required just to generate the energy needed for continued AI expansion ​ ​ 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 survival. Yeah, yeah. But the big thing is that, I mean, my approach, it's a richer approach because there's so much computing power coming back over, but it's more of an organizational form. It's not just trying to find the right set of words here, but the biggest impact on me is that somebody will give me a fact about something. They read about something, they watch something, they listen to something, and they give the thought. And what I find is rather than immediately engaging with the thought, I said, I wonder what the nine thoughts are that are missing from this. Speaker 3: Right? Speaker 1: Because I've trained myself on this 10 things, my 10 things approach. It's very useful, but it just puts a pause in, and what I'm doing is I'm creating a series of comebacks. They do it, and one of them is, in my mind anyway, I don't always say this because it can be a bit insulting. I said, you haven't asked the most important question here. And the person says, well, what's the most important question? I said, you didn't ask me whether I care about what you just said. You care. Yeah. And I think it's important to establish that when you're talking to someone, that something you say to them, do they actually care? Do they actually care? Speaker 1: I don't mean this in that. They would dismiss it, but the question is, have I spent any time actually focused on what you just told me? And the answer is usually if you trace me, if you observed me, you had a complete surveillance video of my last year of how I spent my time. Can you find even five minutes in the last year where I actually spent any time on the subject that you just brought up? And the answer is usually no. I really have, it's not that I've rejected it, it's just that I only had time for what I was focused on over the last year, and that didn't include anything, any time spent on the thing that you're talking about. And I think about the saying on the wall at Strategic Coach, the saying, our eyes only see, and our ears only here what our brain is looking for. Speaker 2: That's exactly right. Speaker 1: Yeah. And that's true of everybody. That's just true of every single human being that their brain is focused on something and they've trained their ears and they've trained their eyes to pick up any information on this particular subject. Speaker 2: The more I think about this idea of that we are all basically in society living large language models, that part of the reason that we gather in affinity groups, if you say Strategic coach, we're attracting people who are entrepreneurs at the top of the game, who are growth oriented, ambitious, all of the things. And so in gatherings of those, we're all working from a very similar large language model because we've all been seeking the same kind of things. And so you get an enhanced higher likelihood that you're going to have a meaningful conversation with someone and meaningful only to you. But if we were to say, if you look at that, yeah, it's very interesting. There was, I just watched a series on Netflix, I think it was, no, it was on Apple App TV with Seth Rogan, and he was running a studio in Hollywood, took over at a large film studio, and he started Speaker 1: Dating. Oh yeah, they're really available these days. Speaker 2: He started dating this. He started dating a doctor, and so he got invited to these award events or charity type events with this girl he was dating. And so he was an odd man out in this medical where all these doctors were all talking about what's interesting to them. And he had no frame of reference. So he was like an odd duck in this. He wasn't tuned in to the LLM of these medical doc. And so I think it's really, it's very interesting, these conversations that we're having by questioning AI like this, or by questioning Charlotte or YouTube questioning perplexity or whatever, that we are having a conversation where we're not, I don't want to say this. We're not the smartest person in the conversation kind of thing, which often you can be in a conversation where you don't feel like the person is open to, or has even been exposed to a lot of the ideas and things that we talk about when we're at Strategic Coach in a workshop or whatever. But to have the conversation with Charlotte who's been exposed at a doctoral level to everything, it's very rewarding. Speaker 1: She's only really been exposed to what Dean is interested in. Speaker 2: Well, that's true, but she, no, I'm tapping into it. I don't know if that's true. If I asked her about she's contributing, her part of the conversation is driven by what I'm interested in, but even though I'm not interested in the flora and fauna of the Sub-Saharan desert, I'm quite confident that if I asked her about it, she would be fascinated and tell me everything she knows, which is everything about Sub-Saharan flora and fauna. Speaker 1: How would you even know that? Speaker 2: I could ask her right now, because Speaker 1: She's been exposed to ask her, here's a question for Charlotte. When she's not with you, is she out exploring things on her own? Does she have her own independent? Does she have her own independent game? And that she's thankful that you don't use up all of he

    52 min
  7. Ep160: AI and the Future of Creative Work

    07/16/2025

    Ep160: AI and the Future of Creative Work

    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 In this episode, Dan and I discuss the revolutionary impact of AI on creativity and productivity, highlighting how our AI assistant, Charlotte, crafts personalized emails that reflect our personalities. We explore the concept of time management as a game, where achieving daily goals brings a sense of accomplishment and managing time effectively can alter our perception of time itself. The conversation touches on the balance between digital engagement and real-world experiences, emphasizing the impact of excessive screen time on teenagers' mental health. We delve into the importance of self-awareness and leadership in a virtual world, using a mental framework to navigate internal dialogues and embrace creativity. There's a fascinating discussion on the role of virtual platforms like Zoom during the pandemic, which have reshaped brainstorming and productivity by facilitating more focused and reflective sessions. Our guests share their experiences of evolving creative partnerships, emphasizing the shift from idea curation to output command, and the benefits of structured playfulness in enhancing creative capabilities. Finally, I reflect on the potential of AI to deepen personal and professional growth, highlighting the anticipation of continued collaboration with Charlotte for fresh insights and experiences. 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 need to sit down and write. Two, you're naturally prolific. This just catches the water from your stream. Three, you already have an audience who loves hearing from you. And four, you're building a library, not just sending one-offs. Dan: Yeah, it's very interesting. I mean I, charlotte is several levels higher than Charlotte is several levels higher than my current confidence with AI. I mean what you're doing, Because I do other things during the day. Do you know that, Dean? Dean: I mean, I do Wait a minute, your week isn't just going around getting observations and sharing them with me on Sundays. Come on. Dan: That's all I can do. But the thing is just from the perplexity interchange. It's really interesting what I'm learning about my ambitions and my intentions, which you're doing too, of course. But I just move on to the next capability and I think that probably you're in a real steady flow of that. But, for example, I had 45 minutes before I was coming on with you this morning. I said let's just write a chapter of a book. Dean: And. Dan: I do it with a fast filter and seven minutes ago it's complete. I have it with a fast filter and seven minutes ago it's complete. I have a complete. So what that means is that I have a fast filter that. I can sit down with Shannon Waller who interviews me on it then it gets, then it gets transcribed, mm-hmm, and then it goes to the writer editor team who put it into a complete chapter. But I've completed my, except for being interviewed on it, which is all this stuff and so yeah. So I mean that would be something that, previous to perplexity, I would think about for about a week and then. I would have a deadline staring me in the face and I'd have to get it done. And I do a good job. You know, I do a good job and yeah but here it's just how much is deadline? Dean: do you think is the catalyst? Dan: oh, yeah, yeah. Dean: A hundred percent. Dan: But the deadline is Thursday for this and I would be doing it Wednesday night. Here I said I know I can knock this off before I talk to Dean. I said I know just from my experience. So you know that was like 28 minutes. I had a complete chapter where, well, if you include the not getting to it with actually getting to it, it's probably about five hours. Dean: About a four to one ratio. Yeah, exactly, no, no. Dan: But I used to do this with the in the early days. I had a lot of life insurance agents. Like you have a lot of real estate, real estate agents, and I said, those big cases, those big cases, some of the big cases you have, and the problem with the life insurance industry is that you put in an enormous amount of work before you even know if there's a possibility of a payoff. So they said, well, those big cases, I had one once. It took me two years. The person said it took me two years and I said, boy, it took a long time. I said actually no, I said the actual result was instantaneous. Dean: It was not getting the result. Dan: that took two years, and I think that this really relates to what AI does. We've put time estimates on things where it all depended upon us. And we say well, that'll take me five hours to get to that result. And this morning. It took me 28 minutes to do it and I was, you know, and it just flowed there. There was no problem. It was in my style and had my voice. You know the way I write things, so it's really, really interesting. Our time estimation is what's changing. Dean: I agree, because the base reality of time is constant. You know what I've been likening. Dan: You're either in the river, you're either in the water or you're not in the water. Dean: That's exactly right. You're exactly right. Dan: Should I jump? What's it going to feel like when I get there, exactly? Dean: Have you seen? There's a video game called Guitar Hero and it's on, you know, xbox or any of these other ones, and they have a guitar and instead of strings it has buttons yellow, blue, green, red and you are on a. You're standing at the base of what it looks like a guitar bridge with the strings there, and when you start the game, the music starts moving towards you, like you are in a Tetris game or something right it's coming towards you. Dan: When you said that, I just thought of Tetris. Dean: Okay, yeah, exactly so it's coming towards you like Tetris, and then it's showing you what you need to press, right at the moment. When it hits the line, the horizon, right where it meets you, you have to be, you press. You know red and then green and then blue,

    59 min
  8. Ep159: Unlocking the Future of Learning

    07/08/2025

    Ep159: Unlocking the Future of Learning

    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 We discuss the overwhelming volume of digital content and how it challenges the utility and comprehension of information in the modern age. Dean talks about the potential impact of artificial intelligence on traditional educational institutions, like Harvard, and how AI might reshape our understanding of expertise. Dan describes the intersection of historical innovation and modern technology, using the invention of the printing press and its early legal battles as a case study. We explore how AI democratizes access to information, enabling individuals to quickly gather and utilize knowledge, potentially reducing the role of traditional experts. Dean shares humorous thought experiments about technological advancements, such as the fictional disruption of electric cars by the combustion engine, highlighting the societal impacts of innovation. Dan critically examines energy policies, specifically in New York, and reflects on creative problem-solving strategies used by figures like Donald Trump and Elon Musk. We reflect on the evolving landscape of expertise, noting how AI can enhance creativity and transform previously unexplored historical events into newfound 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: 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 would be 30 be 11 000, 32 years, and so you think about if you've got a million hours of content it would take you know it's so long to consume it. Dan: You know it's funny. I was thinking about that because you know there's a conflict between the US government and Harvard University. I don't know if you follow this at all. No, government and Harvard University. I don't know if you follow this at all. Because no? Yeah, because they get about. You know they get I don't know the exact number, but it's in the billions of dollars every year from the US government, harvard does you know? Harvard does you? know, and and. But they, you know they've got some political, the DEI diversity, and the US basically is saying if you're, if you have a DEI program which favors one race over another, we're not going to give. We're not going to give you any more money, we're just not going to give you any more money. I mean unless it's if you favor one racial group over another, you don't get the. You don't get US tax money. So they were saying that Harvard has $53 billion endowment. And people say, well, they can live off their endowment, but actually, when you look more closely at it, they can't, because that endowment is gifts from individuals, but it's got a specific purpose for every. It's not a general fund, it's not like you know. We're giving you a billion dollars and you can spend it any way you want Actually it's very highly specified so they can't actually run their annual costs by taking, you know, taking a percentage, I think their annual cost is seven or eight billion dollars to run the whole place billion to run the whole place. So if the US government were to take away all their funding in eight, years they would go bankrupt. The college would go, the university would just go bankrupt, and my sense is that Trump is up to that. The president who took down Harvard. The president who took down Harvard. It wouldn't get you on Mount Rushmore, but there's probably as many people for it as there are against it. Dean: Well, you never know, by the end it might be Mount Trump. We've already got the gulf of america who named it? Dan: anyway, yeah it's so, it's, yeah, it's so funny because, um you know, this was a religious college at one time. You know, harvard, harvard college was once you know, I I'm not sure entirely which religion it was, but it was a college. But it's really interesting, these institutions who become. You say, well, you know they're just permanent, you know there will never be. But you know, if a college like a university, which probably, if you took all the universities in the world and said which is the most famous, which is the most prominent, harvard would you know, along with Cambridge and Oxford, would probably be probably be up and you know what's going to take it down. It is not a president of the United States, but I think AI might take down these universities. I'm thinking more and more, and it has to do with being an expert. You know, like Harvard probably has a reputation because it has over, you know, 100 years, anyway has hundreds of experts, and my sense is that anybody with an AI program that goes deep with a subject and keeps using AI starts acquiring a kind of an expertise which is kind of remarkable, kind of an expertise which is kind of remarkable. You know, like I'm, I'm beginning that expert expertise as we've known it before november of 2022 is probably an ancient artifact, and I think that that being an expert like that is going to be known as an expert, is probably going to disappear within the next 20 years. I would say 20 years from now 2045,. The whole notion of expert is going to disappear. Dean: What do you? Think I mean you think, I think yeah, I have been thinking about this a lot. Dan: You'll always be the expert. You'll always be the expert of the nine-word email. That's true, forever, I mean on the. Mount Rushmore of great marketing breakthroughs. Your visage will be featured prominently. That's great. I've cemented my place in this prominently. Dean: That's great. I've cemented my place. Yeah, that's right. Part of that is, I think, dan, that what I am concerned about. Dan: That would be the highest mountain in Florida, that's right, oh, that's right. Oh, that's funny, you'd have to look at it from above. Dean: That's right. The thing that I see, though, is exactly that that nobody is doing the work. I think that everybody is kind of now assuming and riding on the iterations of what's already been known, because that's what that's really what AI is now the large? Language. That's exactly it's taking everything we know so far, and it's almost like the i

    1h 2m
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4.3
out of 5
9 Ratings

About

Join Dean Jackson and Dan Sullivan as they talk about growing your business and living you best life in Cloudlandia.

Information

  • Creator
    Dean Jackson and Dan Sullivan
  • Years Active
    2020 - 2026
  • Episodes
    160
  • Rating
    Explicit
  • Copyright
    © 2026 Welcome to Cloudlandia
  • Show Website
    Welcome to Cloudlandia

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