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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. Ep169: Arguing With Time

    5 DAYS AGO

    Ep169: Arguing With Time

    Every conversation has the potential to reveal something useful hidden within the ordinary, and this one delivers several of those moments. In this episode of Welcome to Cloudlandia, we catch up after Dan's 11th trip to Buenos Aires for his ongoing stem cell treatments, where he shares a remarkable milestone: a 12% increase in brain volume over three years, roughly equivalent to reversing 30 years of cognitive decline. The conversation flows naturally into Dean's growing practice of "phone fasting" and constraining his available hours, and how that's led to a heightened clarity about where attention actually goes each day. We then dig into the idea of "creating a better past", the practice of making today worth remembering tomorrow, and how this connects to calendar structure, scheduling disciplines, and the real cost of vague future planning. Dan shares why he treats his schedule as a commitment rather than a suggestion, and why words like "should," "would," and "could" are blame-shifting words that quietly block learning and behavior change. Dean's shift to locking in six months of workshops in advance gives a concrete example of how structure actually creates freedom. The episode closes on a thought worth sitting with: Dan's observation that at the bottom of all unhappiness, there's an argument with time. The conversation between these two has a way of making the abstract feel immediately actionable, worth your full attention. SHOW HIGHLIGHTS Dan increased his brain volume by 12% in three years through stem cell treatments, equivalent to reversing roughly 30 years of cognitive decline. Only 0.05% of people are proactively using AI to create output, meaning the competitive advantage window for early adopters remains wide open. Strategic Coach's 250 thinking tools stay permanently "upstream" from AI, because AI can only work with what humans have already created and published. Dan eliminated "should," "would," and "could" from his vocabulary entirely, calling them blame-shifting words that signal complaint without any intention to change behavior. Dean locked in six full months of workshops in advance for the first time, discovering that visible structure on the calendar creates bookings, and momentum that vague future planning never could. Dan's rule for unhappiness: at the bottom of every persistent dissatisfaction, you'll find someone having an unwinnable argument with time. Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT (AI transcript provided as supporting material and may contain errors) Dean: Welcome to Claudelandia. Mr. Sullivan. There he is. Are you in Argentina? Dan: Nope, nope. Dean: No, I'm Dan: Back in Toronto. No, we arrived about noon yesterday. We got back. Yeah. Dean: Okay. Joe is on his way. Dan: Yep. Yep. He left last night. Dean: Well, he didn't leave last night actually. Well, he missed his connection. So that's a problem. Yeah, hopefully he figured it out, but he was definitely on the ... We're not happy till you're not happy airline experience program. Dan: Yeah. Dean: So Garnet and Shirley, they were on the flight that took off. He was so frustrated. Yeah, he was so frustrated because he was on the runway or on the ramp and they were just taken off, so he missed just barely. Dan: You know, people are not necessarily talk about Joe, but I noticed a lot of people are throughout their entire life, they're about three hours late. Dean: Oh, just missed. Yeah, exactly. Dan: Yeah. Yeah. And if they just take one future event or one present event out of their life, they'd be on time, but there's always one thing that makes them three hours late. Dean: That's funny. Dan: Yeah. Dean: So you're in Toronto now? Dan: Yeah, just got back. Yeah. Yeah. Dean: Perfect. Dan: And the snow is starting to melt. Dean: Okay. That's what I hear. Dan: That's Dean: What I hear. You can see the light at the end of the tunnel. Dan: Yeah. Yeah. The power went out in our neighborhood last night. Suddenly it was just completely black, but at our house, five seconds later, the generator kicked in and we had full lights, electricity. Everything was working. Dean: Oh, see? Dan: Yeah. Dean: That's why you get a generator, right? Dan: Yep. Yep. Yep. Yep. Yep. Dean: Because that's like doing an experience transformer in advance. Dan: Yeah. Dean: Looking forward. Dan: I remember a New Yorker cartoon a long time ago, 30, 35 years. And it shows this elderly couple standing at a corner in New York City, a street corner. And right in the middle of the intersection is a dead elephant. Dean: Oh my. Dan: And the wife, the older lady is saying to her husband, "Elmer, I'm never going to complain about you bringing that elephant gun with you on a date." Dean: Oh my goodness. That's so funny. Better, safe than sorry. Dan: You never know when the elephant's going to show up. Dean: That's exactly right. Better to have the gun and not need it. Oh Dan: Yeah. Yeah. Yeah. It may be socially awkward, but you never know when you're going to need that elephant gun. Dean: I love it. So this is- Dan: This is our 11th trip to Buenos Aires. Dean: So what's the progress report? Dan: Yeah. Well, it's interesting because I'm the oldest patient that they've ever had at this clinic who's doing this procedure where you're replacing a cartilage and it's completely back. But what they've discovered is that it's a very young cartilage. It's an early life cartridge, which is okay if you're 13 pounds. Dean: Right. Dan: Yeah. But I weigh more than 13 pounds. And so it's a brand new cartilage. It's completely back. So if I do an MRI lying down, it's completely back. But if I do an MRI with me standing with my full weight, it's as if nothing's happened yet. Dean: Oh, really? And that's ... Well, what's the protocol for that too? Dan: It's kind of a gelatin that they put into the knee now, and it gradually kind of creates a structure in there. I think this is from the cosmetic world, where they put this in people's Dean: Cheeks or they- Wharton's jelly or whatever. Is that what you're talking about or is that Dan: Something that- Yeah, something like that. But gradually it'll reinforce the growth. My cartilage is growing at a much faster pace than a six month old baby would be. Yeah. And the pain is less. I Dean: Was just going to say, what's the practical thing? Dan: I would say if I compare to a week now, a seven day experience to seven days before I went for my first treatment, which was November of 19 to 2023, so it's two and a half years, basically. My pain is down somewhere between 80 and 90%. Dean: Oh, that's awesome. And that's really- Dan: Yeah. Yeah. I mean, pain is the problem. Dean: Well, there you go. Dan: Well, Dean: That's Dan: Just the knee, but the big Dean: One Dan: Has been the brain. I mean, by far the biggest impact because they do it on my knee for cartilage purposes. They do it on both my ankles because I have Achilles tendons, broken Achilles tendons in both of my ankles, and they're good. They're good. They're better. There's more flexibility, more push off. But the big one has been the stem cells to the brain, and I've increased my brain volume by 12% in three years. Dean: 12%. Dan: 12%. I mean, Dean: That's great. And Dan: That's about 30 years. That's equal to about 30 years of decline. Dean: Wow. Dan: So I would be ... Dean: Basically, Dan: I'm back where I was when I was 52. Dean: Brain wise. Dan: Being 82 right now. And I notice it. I notice it too. Dean: You do? What do you notice? Like your brain feels more limber and alive? Dan: No, the biggest thing is that the world makes sense. Dean: Okay. Okay. That's Dan: Interesting. The entire world now is suffering from Trump to arrangement syndrome. Dean: Oh my goodness. Yeah. It's so ... Yeah, it really is. I think consciously- Dan: He's taken on a historically unique role where there's nobody who's indifferent to him. Dean: Right. Exactly. Dan: There's no in between. Dean: Yeah. I mean, it's really ... Yeah, this is ... It's funny because with my phone fasting and my zone of my 12:00 PM till 6:00 PM is really because I'm constraining the available time that I have to meet with people, that those times are filling up. So I really have very little time to pay attention to what's going on. Like just at a tippy top level, I know that we've bombed Iraq or Iran, sorry. But that's really ... I have not ... I've escaped really all of the other ... Just cursorily or peripherally, I've seen things about Dubai and the Emirates and stuff Dan: Like that. Well, I think because it was a war, it's a war. So people say, "Well, he's causing a war." Actually, the war has been going on for 49 years, but it's only been from one side. So the Iranians, the Mulas, the whatever they are, declared war on the United States in 1979, but it was only Dean: In Dan: 2026 that an American president noticed it. And he said, "Oh, you can't do that. Dean: " Yeah. Wait a minute. Dan: Wait a minute. Yeah. I knew I had an itch there. I didn't know what it was. So why don't we make this quick? We'll just destroy your entire leadership in the first half hour. Dean: Okay. There we go. Reset. Dan: There we go. There we go. You tried to get our attention. It took you 49 years, but you got our attention and here it is. Yeah. Dean: Yeah. So I look at that for me as ... Dan: Sure. Dean: That's been a noticeable difference is just- Well, that's Dan: Great. Dean: ... general awareness. Dan: And I don't think you've deprived the world of anything by not paying attention to it. Dean: No, because I think you said it when you gave up TV, you made the observation that there's a lot better things going on in your brain than our in that. And for me, I'm realizing that exact same thing. I've been really loading up a large language model in my brain of being exposed to so much stuff now. And yeah, so now it's really building the interface to tap i

    1hr 4min
  2. Ep168: Why Relationships Still Beat Algorithms

    18 MAR

    Ep168: Why Relationships Still Beat Algorithms

    AI is producing more content than ever, but the competition for real human attention has never been fiercer, and no algorithm is going to change that. In this episode of Welcome to Cloudlandia, we open with Dean noticing a new kind of AI fatigue, the creeping discomfort of scrolling through feeds filled with emotionally manipulative, AI-generated content designed to mimic reality. Dan adds his own observation: the UN’s push to centrally control AI development, which he sees as less a threat and more an unintentional comedy. From there, the conversation gets into the economics of attention, Dean’s framing of 1,000 waking minutes per person per day as a fixed resource, and Dan’s eight years of recovered attention after cutting television (roughly 800 hours a year, or 100 full days). We then work through the distinction between capability and ability, why giving everyone access to the same tools doesn’t level the playing field, any more than putting a grand piano in every home produces Billy Joel. Dan shares a striking data point from Strategic Coach: after 36 years in business, 85% of their 800 registrations last year still came through personal referral, no technology involved. That leads Dean to a new concept he’s developing called “REAL-ationships,” the coming premium on trust built with actual people as AI-generated mimicry becomes harder to distinguish from the real thing. Dan caps it with a sharp observation: technological mimicry is not emotionally satisfying, at least not after the first time. This episode lands on a counterintuitive truth for any business owner: the more powerful AI gets at producing content at scale, the more valuable a genuine human relationship becomes. It's worth a listen. SHOW HIGHLIGHTS Dean identifies a new kind of AI fatigue—not from using it, but from being unable to escape emotionally manipulative AI-generated content in everyday feeds. Dan recovered 800 hours of attention per year—equivalent to 100 full days—simply by cutting television eight years ago. Everyone has 1,000 waking minutes per day; with roughly 450 already consumed by screen time, the real scarcity isn’t content—it’s attention. Capability vs. ability: giving everyone a grand piano doesn’t produce Elton John—the qualitative edge still belongs to the person, not the tool. After 36 years in business, 85% of Strategic Coach’s 800 annual registrations still come from personal referral—no technology involved. Dean’s new concept “REAL-ationships”: as AI mimicry becomes undetectable, the value of trust built with a real person you know is only going to increase. 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. Dan Sullivan: Mr. Jackson. Welcome to Cloudlandia Dan Sullivan: Yes. Welcome to Cloudlandia. Dean Jackson: So you know what's funny? Dan Sullivan: Is it getting congested? Dean Jackson: Oh, I realized, I think I've noticed that today or this week, I reached a level of AI fatigue that I'm noticing is a different sensation in that- Dan Sullivan: It's like the 18 mile mark of the marathon. Dean Jackson: I think that's true. I'll tell you what happened for me is that when I watch Reels or Instagram or Facebook, any of the things, what I'm noticing is the majority of the things that I'm seeing now are AI. And it's getting to where it's not as obvious that it's AI, but it is AI and you can tell that it's AI and it kind of is getting to where it's bothersome. And I realize that this is like we're seeing things, especially when they're trying to make things, they're using it now to create videos that tug on your heartstrings in a way like this family adopted this lion mother who laid her ... They fed the lion and now the lion brings back her cubs to meet the homeowners. And it's just so ridiculous. And everybody is ... Dan Sullivan: Yeah. And this is in Monica Beach, right? Yeah, exactly. It's near the Ferris wheel on Monica. Yeah. Dean Jackson: Santa Monica here. Right. Exactly. Santa Dan Sullivan: Monica. Santa Monica. Yeah. Dean Jackson: It's Just so ... So I realize now, and the fact is that most people don't realize it. I mean, there's so much engagement and you start to see now how just all of these situations where people are being confronted or having arguments or what looks like ... This is where it becomes troublesome is the propaganda ones where they're showing confrontations or arguments between two people. Angry Karen does this or confronts this person or all these things where it's like ... I don't know. It's like ... I always say how Jerry Spence talked about that our minds are putting out their psychic tentacles, testing everything for truth, and it can detect the thin clank of the counterfeit. And I think that that's true, but I worry that many people's counterfeit detectors are not as tuned in as ours are. And I could see that. Dan Sullivan: Well, there's an old phrase that nobody was ever seduced to wasn't looking for sex. Dean Jackson: That's true. Yeah. Dan Sullivan: In other words, you've got to be looking for ... For them to have any impact, you have to be looking for ... I mean, to a certain extent, you're only subject to propaganda if you're looking to be propagandized. I Dean Jackson: Don't know. Dan Sullivan: It's kind of funny. I had a different AI experience this week, and I think mine is more a source of humor than yours is. Tell me. And that is that the Secretary General of the UN says now that the UN has to be in control of the development and the expansion and the use of AI to guarantee that there needs to be a centralized bureaucratic control AI, otherwise it will be misused. It will be misused. And I said, "If the right team of comedians will just sort of get on this UN thing of trying to control the AI, I think there's ... At least in the short term, there's some real humor here. You can get some real Dean Jackson: Humor Dan Sullivan: Of the UN as a thought and AI as a thought." I think if you put those two together, there's immediate jokes that you can come up with. They want three billion. Now, which country has three billion to get to the UN? Dean Jackson: I know one. Dan Sullivan: Anyway, because they want to distribute it, distribute, which requires bureaucrats to third world nations, so to make sure that they can bring themselves up to speed on AI. So I think this has got some comic possibilities. Dean Jackson: Oh, man. Yeah. Dan Sullivan: Where's Monty Python when we need them? Dean Jackson: Exactly. They've been canceled. They were canceled. That's what happens. We cancel everybody who's got common sense. I think I mentioned that I saw- Dan Sullivan: Can I ask you a question? Are you surprised that this is happening? Dean Jackson: I'm not surprised. I mean, if you look at it that we're not even two and a half years into it right now, and when you see the stuff that is escalating, like now the Claude bots are this becoming agentic AI, that's the new buzzword, that it acts on its own and can do ... It's like becomes an army of who's. It's like if you just track the trajectory of where this actually goes, like if you're really ... If we're at a point right now where video and audio is already there, but if you get to a point where video is indistinguishable, like undetectable difference, that's coming. We're moments away from that. And I have a friend who was just saying she had a call from a bot, like an AI thing that's calling realtors and the ... Shortly into the conversation asked ... Caleb was the guy who was talking. She's like, "Caleb, are you a bot?" And then he admitted that he was a bot and then she kept him on the phone for 20 minutes because they hadn't safeguarded him. So she's getting all the, what he's trained to do, like how many and like 30% of the people don't clue in that he's a bot. And that's the truth. His mission was to call these agents, to have the conversation with them just to get the interest to book an appointment with the real person, right? So these are appointment setting bots. And he said that 30% of the people that they talk to don't clue in that it's an AI and they happily set an appointment. And then on the appointment, the human then is pitching this service of, "You didn't know it was a bot, so this is like you want to use this for your business." And I thought, wow, it's very ... Yeah, it's really, it's something where we are. So I really don't know. And you and I, you and I are kind of once removed. Dan Sullivan: It's interesting. I put together an article and I actually sent it to Jeff Madoff and I said 10 AI issues that are going to become very quickly political and how each of the parties, the Democratic Party and the Dean Jackson: Republican Dan Sullivan: Party would respond to it. And once the interesting thing is that with all 10, they would respond differently. So it's going to be ... And they'll ... So they're going to have a different point of view. But I think that the moment that it becomes political, then it'll be like any other technology. It'll be like industrialization, Dean Jackson: It'll Dan Sullivan: Be like television, it'll be like radio. The moment it gets fully ... The political sector of society immediately engages with it, then you'll see that it'll become even more complicated and confusing and complex than it is right now because each of the parties is going to want to utilize AI for its own electoral reasons and to get information out. The one factor though is that our brain still can't concentrate on more than one thing at a time Dean Jackson: And Dan Sullivan: I don't think AI is going to make the least bit of difference of making humans be able to engage with more than one thing at a time. Dean Jackson: Oh yeah, yeah. No, that's the thing. I said that. I

    1hr 5min
  3. Ep167: Timing, AI, and Betting on Yourself

    11 MAR

    Ep167: Timing, AI, and Betting on Yourself

    The entrepreneurs quietly mastering AI right now won't make headlines, they'll just quietly take market share. In this episode of Welcome to Cloudlandia, we trace how birth timing, access, and circumstance shape who becomes an outlier from Malcolm Gladwell's hockey birthday effect to how Bill Gates got his 10,000 hours on a mainframe. Dan connects those dots to today's college graduates, whose degrees have been quietly devalued as AI handles both entry-level tasks and executive scheduling. The generation that sidesteps that broken system and goes straight to mastering AI, Dan argues, is the Andre Agassi of our moment, getting an unfair head start while everyone else is still in line. We shift into the mechanics of entrepreneurial success, where Dan introduces a new Free Zone tool: separating intentional wins from accidental ones. Some of your biggest breakthroughs, like Dean switching from professional tennis to real estate after watching a 15-year-old Andre Agassi dismantle a field, weren't planned, they were recognized in the moment. Dan also shares Day 75 of his 'Creating Great Yesterdays' practice, and how reframing ADD as emotional commitment to too many future possibilities at once finally gave him a way to work with it rather than against it. What ties this conversation together is a quiet argument for building inevitability into your environment. Whether it's locking your phone in a box, structuring a Free Zone summit around a single tool, or recognizing when the game you're in no longer matches who you're becoming, the clearest wins come from making the right behavior the only option. This episode rewards multiple listens. SHOW HIGHLIGHTS The entrepreneurs quietly mastering AI won't complain — they'll just take market share while others are shouting about fairness. Dan's "Creating Great Yesterdays" practice — now at day 75 — may be the most practical ADD hack you've never heard of. Dean switched from professional tennis to real estate at 21 after watching Andre Agassi win his first pro tournament — timing changed everything. Dan ran an entire Free Zone Summit day using just one tool — Guesses, Bets, and Payoffs — and calls it the best he's ever pulled off. History isn't a roadmap — it's a record of everything people didn't expect. Dan on why anyone claiming to predict the future is probably selling something. The Mr. Beast $400,000 weight-loss experiment and what it reveals about designing environments where success becomes inevitable, not optional. Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT (AI transcript provided as supporting material and may contain errors) Dean: Welcome to Cloudlandia. Mr. Sullivan. Dan: Mr. Jackson. Quality training. Quality training. I guess- Dean: For quality Dan: Purposes. Dean: That's why Dan: Everything Dean: Is recorded, right? Dan: I guess we need more of that, don't we? Quality training. Yeah. Dean: So you made it back? Dan: Yeah. It was unbelievable how we got back. Everything was exactly on time. Dean: Oh my goodness. Dan: Yeah. I put that date in the calendar. Dean: So they've abandoned their, we're not happy till you're not happy policy. Dan: Yeah. And in San Diego, they have this brand new terminal, which for a while anyway, is just devoted to Air Canada and Southwest Airlines. Oh, goodness. Dean: Wow. Dan: Yeah. Yeah. It's beautiful. I mean, beautifully designed. Dean: This is in San Diego? They have an Air Canada terminal? Dan: No, it's a brand new terminal. And for now, the only airlines are Air Canada and Southwest Airlines. Dean: Oh, okay. And this is in Toronto? No, Dan: San Diego. Dean: Oh, in San Diego. Yeah, yeah. Okay. That's surprising that the ... Dan: Yeah, it opened about six months ago. Oh, Dean: I like that. Dan: It's an extension of the main terminal, but for now. And for a moment in history, I don't know how long, but you just arrive and you walk in and Air Canada is right there. That's great. Dean: They Dan: Take the bags and then you just go to the left a little. And the clear line is we have clearer. And we walked straight through. Bags went straight through and really nice, very nice terminal. But the gate where we needed to be was right there. And the plane arrived on time and we got on time. It took off on time. And we got home a half hour early. I guess the jet stream was more powerful that night. And Dean: Everything is working. That's almost like just a few more of those and not going to erase the taste of your other Dan: Experience. Oh no, that was gone and then that was gone. Oh, Dean: Good. There you go. Dan: That was gone. I don't really hold onto it. I've Dean: Always Dan: Loved the- But I had been playing with a thought recently of not complaining when things don't work, but being excited when things do work. I think my chances of having things work are diminishing, big systems falling apart. And so I said, "I'm just going to take the attitude of anytime something does work, I'm just going to be excited about it. Dean: " That's great. Dan: Yeah. Dean: You're looking ... It's the Pigmalian effect. It's the positive expectation. That's good. Dan: Yeah. You Dean: Know what's ... The location- Dan: I don't understand Pygmalion. I'm thinking about my Fair Lady. Dean: Oh, well, there's a psychological principle called the Pygmalion Effect. And it was a study that they did with teachers where they would Dan: Tell Dean: The teacher that, "Oh, you've got Danny Sullivan, he's gifted. He's like really going places." And the teachers would subconsciously treat you like you're special and you've got real potential. And then they would tell other teachers that you are trouble and don't let you get away. You got to keep your eye on that, Danny Sullivan. He's a problem. Don't let him get away with anything. And in the studies, just subconsciously, the way the teachers treated you, you would outperform if you were treated like you're special and you would underperform if they thought you were a problem. And of course you just poor innocent Danny Sullivan, you weren't aware of it and you weren't doing anything different than you normally do, but the expectation of what your outcome was going to be was affected by the teachers. And I think that that's a good way to look at life. It's along your lines of your eyes only see and your ears only hear what you're looking for, right? Dan: Yeah. Yeah. Yeah. Yeah. I don't think I ever had a difficult teacher. I had some really supportive ones. I can think about four over the 12 years that I was in school that zeroed in. Yeah. Yeah. Dean: I remember, so Mrs. Jefferson, my third grade teacher, if I look back on it, she was the one that identified that Dean is able to achieve excellent results with what seems like little effort. Imagine if he applied himself. She had a really smart way of doing things because she would ... I would get the work done quickly and then I would be talking to the other kids and she was ... One of the other comments was that I was a disturbing influence in the class, distracting the other kids when I was done. So she made me the ... I call it, she assigned me the role of the poet laureate for the class or whatever, but she would allow me, whenever I was done my work, she would give me one of these ... I remember the index card, like a nice size card print thing and these markers. And she would allow me to draw and create something after I was done in exchange for not talking to the other kids. And I thought, wow, that was an interesting exchange. Giving me some other creative outlet without any expectation or whatever, here I am, that's 50 years later and I still, That's a standout moment in my education. Dan: Yeah. Yeah. I think it's important to have one or two adults. I think one of the things that child psychology, that there's one or two adults that zero in on you as a child and takes interest and shows that they think you've got a big future coming. Yeah. I think that's important. Dean: Who was that for you? Dan: Well, I had a third grade teacher also. It was Ms. Miller who broke my heart because the next year she came back as Mrs. McConnell and I lost her. I lost her. Dean: Boy, oh boy. Dan: And then I think there was a seventh grade teacher and then there was an English teacher in high school and actually the school principal actually took a real interest in me. And that was important because ... I mean, in 1950s and '60s, college wasn't a big thing. It wasn't like you're getting your high school students ready for college. And first of all, I was born in the generation that was smaller than the previous generations, and that was the first one. I was in the first American generation. It went from 28 to 46, 1928 to 1946. And consequently, there was more than enough of everything when you got to school. There was more than enough personal attention. When you got into out of school and you went into the marketplace, there was more than enough jobs, there was more than enough everything. So I think I had history, wasn't particular individuals. It was just the historical period. And if you look, basically that generation from achievement wealth ... Silicon Valley was actually created by that generation. Everybody talks about the baby boomers, but it was actually that generation that created Silicon Valley. It was the people who had been born because they were mostly too young to go into the war, the Second World War. Like if you were born in 1928, when the war started, you were 13, so you didn't go into the war. And then they had that big expansion of college education with the GI Bill. And so there was a lot of emphasis on education and you just ... It was ... Remember the cartoon movie, Remembering Nemo, Finding Nemo. Yeah. Dean: Finding Dan: Nemo. Yeah. Yeah. There's that stream off east coast of Australia where if you get into the stream, you go like eight, nin

    1hr 3min
  4. Ep166: The Great Yesterdays

    18 FEB

    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
  5. Ep165: Creating Yesterday to Build Tomorrow

    11 FEB

    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

    1hr 2min
  6. Ep164: AI, Employment, and the Future of Human Connection

    28 JAN

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

    21 JAN

    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
  8. Ep162: Why Creating Value First Changes Everything

    14 JAN

    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
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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
    163
  • Rating
    Explicit
  • Copyright
    © 2026 Welcome to Cloudlandia
  • Show Website
    Welcome to Cloudlandia

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