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Dean Jackson and Dan Sullivan

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

  1. Ep175: Money, Scent, and the Art of the Did List

    2 DAYS AGO

    Ep175: Money, Scent, and the Art of the Did List

    The most enduring business lessons often come wrapped in the most unexpected stories. In this episode of Welcome to Cloudlandia, Dan and Dean kick off with a wide-ranging trip through Canyon Ranch recoveries, golf course geometry, and a viral coyote-versus-governor parable that perfectly illustrates why California and Texas have taken such different economic paths. From there, Dean shares how a podcast about restaurant scent marketing turned into a live experiment: within 24 hours he had a book concept, a cover, and leads coming in at a dollar each for a title called Smells That Sell. Dan adds color from his neighbor, a professional perfumer who revealed that Mexico ranks #1 globally for scent responsiveness while Canada sits dead last. The conversation deepens as Dan walks through David McWilliams’ book Money, tracing currency from 5,000-year-old Sumerian barley loans to Hamilton’s genius design of the U.S. dollar, and why McWilliams dismisses Bitcoin as a Ponzi scheme that only makes sense when priced in dollars. Both Dan and Dean also reflect on their personal productivity experiments: Dan at week 22 of his “looking back” daily system, and Dean six months into his “What would I like to did today?” morning ritual, with sleep anchors and a captain’s-announcement practice that—as he describes it—puts every cell in his body on alert. This one covers a lot of ground, but the thread running through all of it is the same: agency. Whether it’s scent science, ancient money systems, or a daily captain’s briefing to yourself, the practical question is always the same: what can you actually control in the next hundred minutes? Have a listen. SHOW HIGHLIGHTS Dean launched a book concept, cover, and lead-generation ad for Smells That Sell within 24 hours of hearing a podcast about restaurant scent marketing. A professional perfumer’s global data reveals Mexico as the world’s most scent-responsive market—and Canada as dead last, partly because noses freeze. Dan’s “look back” daily system at week 22: measuring only the last 24 hours eliminates the gap and gives you real agency over what you actually control. Dean’s “What would I like to did today?” morning ritual, paired with lights-out at 11 PM and phone-in-box until noon, has measurably improved his sleep and readiness scores over six months. David McWilliams argues Bitcoin fails both tests of money: it’s not stable enough to be a currency, and the first-in/last-out structure makes it a Ponzi scheme—and it can only express its value in dollars. The first named individual in recorded history was Kuzim, a Sumerian beer maker operating on a 30-month barley loan at 33% annual interest—proof that entrepreneurial hustle predates civilization as we know it. 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. Dean Jackson: There he is. Yes Dan Sullivan: Indeed. Dean Jackson: Sue Cloudlandia. I think I just realized last week that I mistakenly thought you were going to be traveling yesterday and then I saw the Dan Sullivan: Notice that Dean Jackson: You had joined in. Dan Sullivan: I had joined in, yes, yes. Didn't shatter my confidence though. Dean Jackson: Good. Because you knew that I was never going to give you up and never going to let you down and that if you tiled in next week at the appointed time, I would be there. Dan Sullivan: There I am. There I am. Dean Jackson: That's funny. Dan Sullivan: No, we were at Canyon Ranch. Dean Jackson: Okay, great. Yeah. I zoomed in for a lot of Genius Network. Yeah. Dan Sullivan: How Dean Jackson: Was your week? Dan Sullivan: Well, weather wise, the weather in Phoenix and in Tucson was spectacular. Dean Jackson: This is the time of year, right? This is while Canadians are dealing with false springs. It's the real deal in Florida and Arizona. Dan Sullivan: Yeah. There's this great podcast, YouTube podcast and Omar's talk it's called. And this guy is a tremendous communicator. And what he does, he's got sort of one perspective, one topic. He just shows the businesses, the millionaires and billionaires and many others who are leaving New York City, leaving San Francisco, leaving Los Angeles and moving to Florida or Texas, basically Texas. And he just really points out how they're on a death spiral. Seattle's another one in Seattle Dean Jackson: In Dan Sullivan: Washington. Chicago, Chicago really bad. Dean Jackson: I saw funniest real today. I was just waiting to join in here. There was a gentleman talking about why California is broke and Texas is not. And he was telling the story of how the governor was out walking his dog in California and the dog got bitten by a coyote and then the coyote bit the governor and he went through the whole thing that he started. The governor started to intervene, but then he reflected on the movie Bambi and realized that the coyote's just doing what that coyote is naturally inclined to do. And so he stopped and then they called the animal control who came and got the coyote for $500 and then took it and did testing to make sure it didn't have rabies or whatever for another $300 and it took it to the vet who charged another thing. And then the governor had to get tested for rabies for 500 and they implemented a study to see about these and awareness campaign and all like $100,000 worth of stuff. And then he said in Texas the governor was out walking his dog and the coyote- He'd Dan Sullivan: Shoot the coyote. The Dean Jackson: Dog and he shot the coyote and continued jogging and he spent Dan Sullivan: 50 Dean Jackson: Cents. That solved the problem. Dan Sullivan: So Dean Jackson: Funny. Dan Sullivan: Yeah. Well, coyotes in California come in many forms. Dean Jackson: Yes, I think you're right. Dan Sullivan: Do you have them in Florida? Dean Jackson: That's a good question. Do we have coyotes? We have Panthers. Do we have coyotes in Florida dining? Yeah, right across the street. She said there's coyotes. Yes. Yes. Dan Sullivan: Coyotes are there. I think they're in all 50 states. They're very adaptable animals. They're omnivores and they can eat anything. We have mirror. We have them within probably two or three miles, two or three miles of where I'm speaking from right now. I'm sure we have coyotes. They're everywhere. Dean Jackson: We also Dan Sullivan: Have Dean Jackson: Panthers. Dan Sullivan: Yeah. And they have Bobcats too. I was reading the Bobcats really like python meat. Oh, is that right? Dean Jackson: Okay. Dan Sullivan: So they're thriving. They're killing the pythons in the Upper Glades. Dean Jackson: Oh, Dan Sullivan: That's Dean Jackson: Great. Dan Sullivan: Yeah. It's really great. Yeah. Dean Jackson: I love it. Dan Sullivan: Just kind of let things be the way they are. Yeah. Well, the story about the governor and the coyote, that the coyote was just doing what Dean Jackson: Coyotes Dan Sullivan: Do. Yeah, that's true of cartel members too. Cartel members just do what cartel members. Dean Jackson: That's true. Dan Sullivan: Yeah. You can't fault them. It's just their nature. Dean Jackson: Yes, exactly. So how long were you at Canyon Ranch? Dan Sullivan: Well, we spent basically two weeks. We went on a Tuesday to Phoenix and then we were there until the Saturday. So we had the two days of Genius Network and then we went down to Canyon Ranch. That was Saturday afternoon. And then we left on Friday. We left on Friday. We came back just a couple of days ago. Yeah. But it was nice. It was just a really very laid back, read lots of murder mysteries and did a lot of walking. I'm doing more walking than I have in three or four years, so it's pretty good. Dean Jackson: Are you Dan Sullivan: Getting Dean Jackson: Your step count up? Dan Sullivan: Yeah. I averaged about ... I'm not like some people who are Olympic level, but I'm 8,000 steps. Dean Jackson: Well, Dan Sullivan: That's the Dean Jackson: Optimal I've read. Is that Dan Sullivan: Right? It's not 10 anymore. It's not 10 anymore. Dean Jackson: No, I think that that's the reality that the diminishing return is there's no extra benefit to 10,000 or 15,000 over there. There's Dan Sullivan: Status. Dean Jackson: Right. Dan Sullivan: No, you always have to factor in status. Does your no good, but there is status. Dean Jackson: Yeah. But 8,000 is like the peak all the benefit stuff you get. What are they called? Dan Sullivan: What's the round of golf gift? Do you do nine or 18 when you're playing? Dean Jackson: Well, normally I'll do 18 but you're driving a cart, but even in a cart, it's 6,000 steps or something. And I think it would be probably 15,000 if you walked the whole course. Yeah. Okay. Dan Sullivan: So let me ask you a question. Dean Jackson: That's DJ. Dan Sullivan: Yeah. If your drives were always down the middle, right online with a hole and your approach shots were always right where they're supposed to be and your puts are right there, 6,000 or you accounting for little side Dean Jackson: Trips that Dan Sullivan: You have to- Dean Jackson: Yeah, little side trips. Like some places you're not allowed to ride on the cart. But if you take, let's say that an average, let's say the golf course 6,800 yards divided by three, 20 ... Oh no, Dan Sullivan: 6,800 Dean Jackson: Yards. Dan Sullivan: We're talking about steps. We're talking about- Dean Jackson: Yeah, so 6,800 yards times three, 20,400 feet divided by thousand roughly. So it's just the straightest path is four miles, which would be probably, I don't know how many steps in a mile, but- Dan Sullivan: 8,000 steps, 8,000 steps. Dean Jackson: So about 24,000. Dan Sullivan: Oh, 24,000. Yeah. Dean Jackson: Steps? Dan Sullivan: When I was 16, I was a caddy and one weekend I double bagged so I had- Oh Dean Jackson: My goodness

    1hr 4min
  2. Ep174: Guessing, Betting, and the AI Attention Economy

    13 MAY

    Ep174: Guessing, Betting, and the AI Attention Economy

    The most valuable currency in an AI-saturated world isn't data or content, it's the 1,000 minutes of attention each person has available every single day. In this episode of Welcome to Cloudlandia, Dan shares a new thinking tool he's been developing with entrepreneurs: Intentional Times Accidental, a framework for distinguishing between results you planned for and opportunities you simply recognized and seized. The conversation connects naturally to a powerful quote Dean encountered, "You don't get what you want, you get what you are", and how that idea links to Dan's work on creating a better past. We also hear how Angus Fletcher trains elite special forces operators not by scripting their responses, but by deepening their personal story so they can make sound decisions in chaotic, unpredictable situations. From there, Dan and Dean trace the same pattern into global affairs, examining how recent moves in the Straits of Hormuz reflect high-stakes guessing and betting under pressure. The conversation shifts to AI's financial sustainability problem, the gap between what AI companies are spending on infrastructure and what the market will realistically pay, and why Dean believes AI-generated content faces a fundamental ceiling in a world where human attention is fixed and finite. Dan observes a cultural blowback already forming, with young people pushing back against AI predictions that threaten their futures, and a surprising surge in religious interest as a counter-reaction to tech-driven culture. This episode finds Dan and Dean at their most candid, trading observations about Perplexity's flattery, Dean's 40 Hz brain-stimulating Beacon light, a dog-calming gadget called PetGentle, and a Henry Kissinger story that perfectly captures what's happening on LinkedIn right now. Listen in for a conversation that moves fast, thinks wide, and lands on ideas you'll be turning over for days. SHOW HIGHLIGHTS The global attention budget is fixed: 8 billion people × 1,000 minutes daily, AI-generated content must compete within that hard ceiling. Dan's new Intentional Times Accidental tool helps entrepreneurs separate planned breakthroughs from lucky ones they simply recognized and seized. Elite special forces operators are trained not with scripts but by deepening their personal story so they can decide well in chaotic, unplanned situations. Dan believes OpenAI cannot legally convert from nonprofit to for-profit mid-streamand predicts the dispute will reach the US Supreme Court. A fake AI-generated scientist published 13 bestselling books over the past year and doesn't exist, Dan's verdict: only dangerous if you believe it. Young people are opting out of AI adoption and turning toward religion in growing numbers, a cultural blowback Dan says is entirely predictable and already underway. 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: Hello there, Mr. Jackson. Dean Jackson: There he is. Are you in Chicago or Toronto today? Dan Sullivan: Toronto. Dean Jackson: Okay. Dan Sullivan: Well, it's very cold. It's very cold. Dean Jackson: Somebody told me that they've had their ninth false spring and it's coming into back to winter. Dan Sullivan: Yeah. It's overcast. It's gray. It's damp. It's cold. Dean Jackson: Oh boy. Oh boy. Oh boy. Well, it seems like you have- Welcome to Cloudlandia. Welcome to Cloudlandia. Are you in Chicago or Toronto today? Okay. Dan Sullivan: Well, it's very cold. It's very cold. Dean Jackson: Somebody told me that they've had their ninth false spring. Back to winter. Dan Sullivan: Yeah. It's overcast. It's gray. It's damp. It's cold. Dean Jackson: Oh boy. Well, it seems like you had a great week in Chicago talking to Chad. Dan Sullivan: You've been talking to Spice. Dean Jackson: I've been talking to Spies. I got my men on the inside. Yeah. So good times? Dan Sullivan: Yeah. I had a really good time. I created a new tool which is called Intentional Times Accidental. And I just have the entrepreneurs in the room take a look at what results they got, breakthrough results, Dan Sullivan: Where it Dan Sullivan: Was intentional. They intended to get that breakthrough. They put a plan in place and they got the result and compared to things that just happened to them and they took advantage of it. Dean Jackson: That's an interesting distinction. I just had a great quote that I heard just this morning and I thought, what a perfect timing. The quote was, let me get it right because it's ... Oh yeah, you don't get what you want. You get what you are. That totally fits with our creating a better past because you are what you did. And what you did is created a better past. Dan Sullivan: Or a better you, maybe. Dean Jackson: A Dan Sullivan: Better Dean Jackson: You. Yeah. But that context of everything we've been talking about that really fit well, you don't get what you want, you get what you are and you are, I'm adding this, but what you are is the collection of what you've done. Dan Sullivan: Did, what you did. Oh, what you did, Dean Jackson: Yeah. Dan Sullivan: Yeah. Yeah. Yeah. And that requires a totally different approach. Dean Jackson: Yeah. It's like it's the inverse of what people ... There's a difference in what you're going to do and intending to do and what you did because that's the only thing. Yeah. What you did is what makes you what you are. Yeah. Dan Sullivan: Yeah. Angus Fletcher who's coming to talk to us in Orlando. First week of June, he talks about the special forces, the Delta Force, Navy SEALs, Green Berets. There's a lot of these different kind of special operators, they're called special operators. And he said that what they train them is how not to ... They don't tell them how to handle situations. They constantly work with them to tell their story. When you were in this situation, what did you do? When you were in this situation, what did you do? How did you handle this? And because they're put into situations that are chaotic, Dan Sullivan: Sort Dan Sullivan: Of chaotic situations, all guesses and bets and they don't have a lot of information being in the chaotic situation, but they have to make good decisions and how do you do that? And he said, "It all depends on the story that you tell yourself. What's the story? What's the story? How have you handled this? How have you handled that? " It's a lot of experienced transformers, to use the coach term. "You did this, this part of it worked, this part of it didn't work, and because of what you know worked and didn't work, how do you handle this similar situation going forward? Dean Jackson: "So you're saying like his whole thing is activating the part that so that you ... Well, how do they use that? To what end is that? How do they train people? Dan Sullivan: Well, they put them into all sorts of practice situations and that you can't prepare for. So they have these vast bases, a lot of them in North Carolina and they put them ... Usually it's dark and something happens, they're given an objective. They have to go and do something and then they're presented with all sorts of unpredictable situations and how do they actually achieve the mission where they have to make it up on the spot. Dean Jackson: And Dan Sullivan: They do this over and over and over again. And the big thing is they have to know what their story is because they can't know what the conditions are because that's not available to them. So they have to fall back on previous successful and unsuccessful experiences. They have to go back and say," How did I do this before? Okay, this is what I have to do. "Yeah, Dean Jackson: Whatever you don't do this. Dan Sullivan: They have to go back to what they are. They have to go back to link this idea up with the idea of great quote. That's a really great quote. Dean Jackson: And I think that then once you've had an experience of something when it comes up, if you know what the right thing to do is, that helps. I find that even in our marketing things, that's one of the progression that we talk about in the VCR formula, vision plus capability multiplied by reach is the vision thing starts as a proposition, moves to proof that once you say ... And imagine it's the same kind of thing there, right? That you look at a situation that a soldier might be put in, they have a proposition based on, well, this is similar to this or whatever, but the next level is proof that this worked and then it moves to be a protocol that now when you reliably have proven that in this situation, if you do this, that this is the outcome and then that becomes property and that Dan Sullivan: Becomes- Dean Jackson: That's an interesting Dan Sullivan: Thing. It doesn't always work. It doesn't always work. Dean Jackson: That's the whole- Dan Sullivan: There's a recent example in world affairs on 28th of 28th of March, Dean Jackson: 20th, Dan Sullivan: I forget when they bombed Iran. I think it's the 25th of- February. February. February. Yeah. And the Ayatollah, the head guy said," We're going to have a meeting on a Saturday morning and that's safe because it's the Sabbath for the Jews so the Israelis won't do anything on Saturday and the Americans only do things at night. So you can feel safe. Say they all gathered at one spot and the Israelis decided to do something on the Sabbath and the Americans decided to do something in the daycare. Dean Jackson: During the day. Dan Sullivan: During the day and they lost 47, 48, 49, I forget the number. They lost 49 of their top leaders in about the first five minutes of the bombing career and they're making a whole series of really bad guesses and bets. On the one hand, we'll cut off all the shipping that comes out of the straight format. We just locked down and the Americans said, "Well, we'll be just

    1hr 6min
  3. Ep173: Rules Over Insights: Time Sense and the Decider Role

    22 APR

    Ep173: Rules Over Insights: Time Sense and the Decider Role

    The most powerful systems aren’t built on motivation; they’re built on rules that make the right action the only option. In this episode of Welcome to Cloudlandia, we follow Dean’s ongoing experiment with structured daily rhythms, phones locked from 10 PM to noon, meals pre-ordered the night before, and two daily golf sessions anchoring his mornings. He’s framing it not as discipline but as finally becoming a “law-abiding citizen” after 30 years of trying to be a maverick. The bigger discovery: for someone with ADHD, freedom lies within structure, not outside it. Dan shares a quiet but significant shift in his Strategic Coach tools, replacing the prompt “What are your three biggest insights?” with “What are your three biggest rules?” Insights are just thoughts. Rules are decisions with direction. He also returns to a theme from his 130-day “Creating Great Yesterdays” practice: that your past isn’t a fixed record of what happened, it’s your interpretation of it, and that interpretation is entirely yours to change. The episode closes with a wide-ranging discussion on AI, technological revolutions, and who actually profits when the world changes, spoiler: it’s rarely the builders. Dan’s historical read on railroads, radio, and automobiles applies just as cleanly to what’s happening now. This one rewards a second listen, especially the segment on time sense and what it means for how you take action. SHOW HIGHLIGHTS Dean’s new rule: phone locked from 10 PM to noon daily, not as willpower, but as a structure that makes the right choice the only choice. Dan replaced “What are your three biggest insights?” with “What are your three biggest rules?” on his thinking tools, and the difference in entrepreneurial traction was immediate. Your past isn’t a fixed record, it’s your interpretation of what happened, and that interpretation is yours to change at any time. In every major technological revolution, railroads, radio, automobiles, only about 5% of builders profit. The real winners are the consumers who apply the technology to their most productive opportunities. ADD and future-thinking may be deeply linked: Dan’s observation that spending today’s attention on things that don’t yet exist is what creates the paralysis most entrepreneurs experience. Dean’s “Decider” role: the bottleneck in any creative system isn’t ideas or energy, it’s the decision about what actually makes it into the real world. 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. Dean Jackson: Well, here we are. Dan Sullivan: Here we are. Here we are. I was listening to the actual words of the song that you have introducing our podcast. And my feeling is that the guy who's singing is lying. Dean Jackson: Well, let's Dan Sullivan: Break it down. He's actually doing all those things and he's actually going to do all those things that he's saying. And I'm just wondering if all songs of that nature is that the singer is actually expressing something that's not true. Dean Jackson: Shadow. Some shadow. Dan Sullivan: Shadow. Shadow. This is the Dean Jackson: Challenge. The shadow side of it. I'm never going to give you up. I'm never going to let you go. Dan Sullivan: He's letting her go. Dean Jackson: Yeah. Oh my goodness. Dan Sullivan: Forget you. I'm Dean Jackson: Never going to Dan Sullivan: Forget. Well, I'm not sure of the gender that he's actually talking about. There we go. These days, you can't be sure. Dean Jackson: That is so funny, Dan. I love ... This is true. Yeah, you've been the first one to dial in. We should let people know the conference service that we use. We have it set up so that there's music playing when the first person arrives and the song is Rick Astley Never Going to Let You Go. Yeah, yeah. So you've been treated to some contemplative time with the lyrics of the song. Dan Sullivan: Yeah. Yeah. My whole feeling is that anything that people are singing about kind of tells you that they're not actually that kind of person. Dean Jackson: I saw there was a- Dan Sullivan: If you have to say it, if you have to sing it, you're not doing it. Dean Jackson: Yeah. I saw a t-shirt that had an image on the front. It said, "Things Rick Assley will never do. " And then it was check boxes. Let you go, give you up, forget you. Check, check, check. Dan Sullivan: Or it's the reverse. That person is doing all those things to Rick. Yeah. Yeah. It's kind of funny. The happiest people in the world are probably not talking about it. Dean Jackson: That's it. Every action has an equal and opposite reaction, right? Dan Sullivan: Yeah. Yeah. Well, what's up? What's up? Dean Jackson: Well, I'll tell you what, it's been another adventure in Club Landia, another week of being in one place geographically on my six month stay radical, let's call it. And I've really been embracing the locking in the big pieces. I've come to see now and suspected it all along that life is really a series of rhythmic patterns that are persistent and are never changing. Trying to align myself with those so that it feels downstream. And I'm really gamifying a lot. I have completely locked in the 10:00 PM till noon, no phone. I feel so much freer with that. Walking in, I think I'm trying to gamify. I'm really learning about my flavor of ADHD, which is really an executive function outside. So for me, that is embracing structure and just kind of realizing that the freedom is in the structure for me. And as much as we try and resist it, it's embracing it is the freedom rather than resisting it. And so I've been setting up my life into zones and that 10:00 PM starts the kind of wind down process. My little gamification lights out by 11:00 PM, that's kind of the thing because otherwise I can kind of just scroll into things. So I'm just setting up little ... If you're imagining skiing down a mountain, it's like I've got little gates that I try and get around. So it's like I've got the 10 o'clock, the phone goes off and I start the wind down practice of getting my day prepared. This last few weeks, I've been choosing my meals for tomorrow in the spirit of creating a better past. I've been choosing my meals using the pre-order function of ... I use Grubhub and DoorDash and Uber Eats. I've got a series of meals that are good. And I pick them the night before so that I don't have to ever make the decision. I look at my day and I figure when would be the right time for them to be delivered. And so that's a great thing. I make it my aim. The other gamification gate wheels up at eight o'clock, meaning I'm up and dressed and out the door and in my car, wheels up at 8:00 AM. And that's a fun thing. I've got the first stop honeycomb, and then I read and have breakfast, and then I'm over at Concord, and I've got two hours of focus times of my golf. I've been golfing. Of course, my analogy is the golf is having a goal, an optimal environment, limited distractions at a fixed timeframe. So those two golf sessions before noon, and then I'm back home, and my phone unlocks at noon, and I spend the first little time catching up, seeing what I've missed, all my appointment, all my time, obligations of talking to people are in Tuesday, Wednesday, Thursday, one o'clock till six o'clock. And yeah, it's a fun, really learning to embrace the freedom and creativity within the framework of what's reality. Dan Sullivan: So what you're telling me is that after almost 60 years, you've become a law-abiding citizen. Dean Jackson: Well, what I've realized is, yeah, you're absolutely right. I think it's perfectly suited that the ... I really started ... I turned pro on the journaling at 30, and I've observed now those 30 years. I'll be 60 next month, and I've realized in looking back at all of those journals, what a gift it is, but it's still been 30 years of sort of not being a law-abiding citizen, trying to be a maverick. And so now it's like I might as well experiment with living within the law. Dan Sullivan: The interesting thing that I've been ... I made a switch in the tools about two months ago, and so you know all the thinking tools we have in Strategic Coach, but at the bottom of every thinking tool, when you've done everything else, you've done the first sheet, which is a new concept, and then you do the triple play, and then you come back and you finish it. And at the bottom, I always had, "What are your three biggest insights from doing this Dean Jackson: Thinking?" Dan Sullivan: And I don't quite know why I did this, but there was a tool and I said, "I don't think we're looking for insights. I think we're looking for rules Dean Jackson: Here." Dan Sullivan: So instead of your three biggest insight, what are your three biggest rules? And it's made a profound difference on the entrepreneurs. And usually, I do all my testing of new tools with the two hour connector Dean Jackson: Calls. Dan Sullivan: And for example, if I do, I do a new free zone workshop every quarter, but I've tested about four or five different tools to determine what's the best structured particular quarter, but I've done tools. I've done rules for the tools. I've done rules to it, and it makes a profound difference because an insight is just a thought. It's just there's no traction, there's no commitment, there's no decision whatsoever. You just had a thought. It's brainstorming. Basically, it's just brainstorming. But rules are a decision that you're going to go in this direction and not that direction. I see that my focus and my activity has to be doing then, therefore, I have to get rid of everything else. And we had a discussion on Friday, on Friday, two days. And I said, "If you talk to any entrepreneur, they don't like following other people's rule

    56 min
  4. Ep172:  Secrets, Surveys, and 30-Year Bets

    15 APR

    Ep172: Secrets, Surveys, and 30-Year Bets

    Protecting what you've built, revisiting where you started, and betting on the systems that have never let you down. In this episode of Welcome to Cloudlandia, Dan and Dean open with a riff on the strange new logic of secrecy in the internet age, where the best way to protect an idea may be to share it widely. Dan's story about a platform speaker who borrowed his Free Days, Focus Days, and Buffer Days framework without credit turns into a sharp point: the internet has made intellectual property both more fragile and more defensible at the same time. Dean connects this to his Nine Word Email and the way naming an idea is often the most durable form of ownership. Dean then pulls out journal number one, dated April 1996, thirty years ago this week, and the conversation becomes a time capsule. He walks through his early real estate licensing business, Toronto and Beyond, and how the same playbook he used then to generate leads in Halton Hills is still running today in Winter Haven, Florida. Dan reflects on his own 25-year journaling project that began after a difficult 1978, and shares that his massage therapist of 34 years recently confirmed his physical condition hasn't changed since they started. The episode closes on a larger canvas: real estate as a measure of civilization, the Louisiana Purchase at 50 cents an acre, Canadian politics, AI-driven job creation, and the quiet argument that the best protection against an uncertain future is a system that has already worked across three decades. SHOW HIGHLIGHTS Dan Sullivan's Free Days, Focus Days, and Buffer Days framework was stolen by a speaker mid-presentation and the audience corrected him before he finished the sentence. Seth Godin's counterintuitive take: before the internet, you kept secrets by hiding them; now you protect them by telling everyone first. Dean Jackson's Nine Word Email became famous globally and naming it was the single act that made it impossible for anyone else to claim it. The same lead-generation playbook Dean built in 1996 for Halton Hills real estate still works today, running virtually unchanged in Winter Haven, Florida. Dan's massage therapist of 34 years told him his physical condition is no different now in his 80s than when they first started working together. For every job eliminated by AI and robotics over the next 15 years, Dan estimates roughly two new jobs will be created,most of them in the legal and regulatory pushback against AI itself. 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: Yes. And AI will know about this call. Probably never. Dean Jackson: Probably Dan Sullivan: Never. It'll be scandalized. It'll be confused. Dean Jackson: Yes. This is the closest to analog. It's like, how did those spies meet in the trip down to our bathing suits neck deep in the ocean, having no wires, nobody listening. That's what Dan Sullivan: We're Dean Jackson: Having right now. Dan Sullivan: Yeah. There's a great story about Reagan, President Reagan. And when he got in, there was a particular situation where it was very clear that the Russians, the Soviets at that time, Dean Jackson: Were Dan Sullivan: Stealing American secrets. Dean Jackson: Very sneaky. Dan Sullivan: And Reagan had an interesting response to it. He said, "You know what we ought to do? Every so often, maybe every six months, we should collect every single secret in the United States and put them in 747s, cargo planes, 747 cargo planes, and fly them all to Moscow and dump them on the runway and fly off. And every six months we just dump all our secrets on the runway." He said, "The sheer confusion that that will cause will destroy the Soviet Union in a matter of a couple of years." Dean Jackson: That's funny, isn't it? Yeah. There's something interesting. Yeah. It's so funny, right? The things that we want to keep secret seem to be more desirable than the things we're willing to share. It's so- Dan Sullivan: Yeah. Just share everything. The way to destroy them. Actually, Seth Godin had a great line. He said, "Before the internet, the way to keep a secret secret was to keep it secret." Dean Jackson: Yes. Dan Sullivan: He says, "The way after the internet to protect your secrets is tell everybody your secret." Dean Jackson: Yeah. Oh, Dan, I can't tell you. So how many times the ... I created this thing called the nine word email. And the best thing I did was name it. And it's become known everywhere. And everybody who tries to present that idea as an original or as a, "Hey, here's this thing I've been working on. " Every single time in the comments is, "Oh, that's Dean Jackson's idea or that. " But predominantly, most people start out with the, "Here's an idea I learned from Dean Jackson." And then they talk about the nine word email. Dan Sullivan: Yeah. Well, I had a similar experience with the entrepreneurial time system, which is free focus and buffer days. So There was a very famous platform speaker. This is probably 1995 and he's in, I think it's somewhere in Texas, I think San Antonio, and he's giving a talk and it's to financial advisors. It's to mainly real estate and financial advisors, couple thousand in the audience. And he said, "I want to tell you about my time system. I've created this new time system." And he says, "It's called Free Days Focus Days and Buffer Days." And the words were not even out of his mouth and about 10 hands come up and people stand up and said, "That's not your time system, that's Dan Sullivan's time system." So I have spies in the audience and we immediately get phone calls afterwards telling us about this event, this situation. And about a week later, I get a phone call from the speaker himself and he said, "Boy, you have a bunch of pit bulls for clients." And he tells me the whole story and I don't let on that I know the story. I don't let on at all. I just say, "Oh, that's interesting." And I said, so he tells me about it and he says, "Who knows where ideas come from?" And I says, "Well, I'll give you a phone number. It's my IP lawyer and he'll tell you where this idea comes from." Yeah, Dean Jackson: I'll tell you Dan Sullivan: Where Dean Jackson: This one comes from. Dan Sullivan: Exactly. I don't know about other God origin ideas, but I can tell you where this one comes from. And he says, "Well, I'm really sorry about this. " He said, "I don't want to be in your bad books." And I said, "Well, you're not ... " I said, "Well, you're not in my bad books, but let me ask you a question. How did the rest of the speech go? Dean Jackson: " Exactly. Yeah, that's funny. Threw him off his game for sure. Dan Sullivan: And I said, "If there's 2000 people in the audience, those 2000 people are going to tell, each of them is going to tell 50 other people about what just happened." So I said, "I don't know what your marketing strategy was here, but I said, I don't think it's going in the direction you wanted it to. Dean Jackson: " Right. That's so funny. And now it's really ... It is interesting that everything now is kind of, we have this public record of the internet, like when somebody talks about something on a podcast that's timestamped or posts about it or publishes something and now on the blockchain even, like what Carrie Oberbrunner is doing with the instant- Dan Sullivan: Instant Dean Jackson: IP of just putting something up and at least, I don't know whether it's been tested or held up. But you look at it either way, it's certainly, it's a level of protection that has not been available. Exactly. Dan Sullivan: And the whole thing is that all IP law is based on timing who did it first. It's not who created it first, it's who applied for intellectual property first. Dean Jackson: Yes, exactly. Stick their claim to it. And that's where, kudos to Carrie for thinking that through and using a new technology of the blockchain to be able to instantly ... I mean, it's the digital equivalent or a much improved thing of mailing something to yourself with a registered letter and not opening it. That's a really ... Dan Sullivan: Yeah, that actually works. Yeah. That actually works. Yeah. I mean, a lot of people, I said that here's the thing, you got an idea, make a copy of it, put it in a letter, go to the post office and register the letter and have it sent to yourself and don't open it, don't open it. I mean, you can write on the outside of the letter what it relates to so you know which one. And if you present this in a legal situation, it will be accepted as timestamp proof. Dean Jackson: Exactly. Yeah. So I think that's pretty great. Now that's where we're headed there. I had something very interesting. Dan Sullivan: Can I mention something? Sure. If you're willing and we'll receive a communication, Kathy Davis, of Strategic Coach, would like to talk to you about actually being the chairperson for a panel at CoachCon. Dean Jackson: Oh, okay, perfect. I love it. That would be Dan Sullivan: Fantastic. Yeah. So I'll tell her this, I'm looking at my watch right here, it's 11:09 and on Easter Sunday that I actually passed on the word that you will receive a communication tomorrow Dean Jackson: From Dan Sullivan: Kathy Davis. And I just want to establish this proof that I actually passed out the message. Dean Jackson: Okay. Yeah, there we go. Timestamped. 11:10. Dan Sullivan: Timestamped. Dean Jackson: 11:10 AM, Eastern Daylight Time. Yeah. Dan Sullivan: Yeah. So if you get a communication from her, when you get beyond noon tomorrow, you will know what it's all about. Dean Jackson: Oh, I can't wait. I can't wait. Yeah, I'm looking forward to it. It's coming up less than 60 days, right? Till Coach Kong. That's exciting. So I was looking, Dan, today, April 5th, yesterday was the date of the first entry in journal num

    1hr 3min
  5. Ep171: The Inevitability System

    8 APR

    Ep171: The Inevitability System

    The most productive stretch of your life probably isn’t waiting for motivation, it’s waiting for the right constraint. In this episode of Welcome to Cloudlandia, we follow Dean’s hundred-day phone fasting experiment locking his phone away from 10 AM to noon and what it revealed about the power of inevitability. Dean calls this his most consistently productive stretch ever, and Dan predicts that by the one-year mark, at least 20 other habits will have quietly shifted as a side effect. The big lesson: willpower is unnecessary when you design a system that removes the other options entirely. Dan shares that he’s now at day 116 of his ‘Creating Great Yesterdays’ practice and is finishing a new quarterly book, Yesterday Creates Tomorrow. He also makes a sharp case for proactive health investment twice-yearly full bloodwork, AI-assisted cancer detection, and taking personal ownership of your body rather than waiting for the system to catch something at stage four. The conversation moves into the language of regret, where Dan breaks down why ‘should,’ ‘would,’ and ‘could’ are manipulation words and how reframing your past experience as a source of lessons removes its power over you. The episode closes with a great business story from a Free Zone client: while every gas station in Washington State started charging for bathroom access, he went the other way, free bathrooms for everyone and created lineups of grateful customers who paid double out of sheer relief. It’s the kind of counterintuitive move that’s easy to describe and hard to execute, which is what makes it worth hearing about. This one’s got a few moments you’ll want to replay. SHOW HIGHLIGHTS Dean’s 100-day phone fasting experiment, locking his device away from 10 AM to noon, produced what he calls the most productive stretch of his entire life. Dan’s prediction: by the one-year mark, at least 20 other habits will have changed as a quiet side effect of the phone fasting discipline. The willpower myth, debunked: Dean’s biggest transferable lesson is that the system does the work when you engineer inevitability and remove all other options. A Free Zone client turned Washington State’s ‘pay $20 before you can use the bathroom’ rule into a competitive advantage, by being the only gas station that didn’t charge. Dan on why ‘should,’ ‘would,’ and ‘could’ aren’t grammar, they’re manipulation tools used to distort your relationship with the past. AI is now detecting cancer predisposition three years before convergence happens. Dan’s case for twice-yearly blood panels: 20 extra healthy years for anyone willing to pay attention. 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: Good morning. Dean Jackson: Welcome to Cloudlandia. Dan Sullivan: Yes. I'm feeling it. I'm feeling the impact of Cloudlandia. Dean Jackson: I love that. There's always a home for us here in Cloudlanvia. Dan Sullivan: Yes. It's Dean Jackson: Our third Dan Sullivan: Space. Yeah. Well, yeah. And it's custom designed. Dean Jackson: That's exactly right. Dan Sullivan: It's custom design. Dean Jackson: You know when I say that, that's a really interesting thing, our third place, because that's how Starbucks, that was the intention of Starbucks when they got started as a third place between work and home, somewhere where you go to meet people and have great conversation. It's so funny because they've completely moved away from that. Now with the drive-throughs and the ... I described the interior spaces of the new coffee places as prison cafeteria style. It's like get your stuff and move along. Don't see them. Dan Sullivan: Yeah. Well, they went through a period, I think it's trying to think about a 10-year period where they were preaching to you, trying to make you a better person. And that didn't work. Don't have a goal in selling any product of transforming human nature. It's one of my- Observable. It's one of my firm foundational stones. Humans are going to do what humans are going to do and don't try to create a better human being. Just give them a little caffeine jolt and some sugar and they're okay. Dean Jackson: Observable life lessons. That's Dan Sullivan: Exactly right. Yeah. Yeah. Yeah. Dean Jackson: It's so funny. Dan Sullivan: Yeah. I think that's really the big thing now because this was actually ... I read an interesting book and it's called The Progressive Era in American History. And it starts kind of, I would say probably right after the Civil War. And it was a middle class. It was like people who lived in nice neighborhoods and they had nice things. And they made it their goal that their responsibility in life was to look at anywhere in America that didn't look like their neighborhood, didn't have their mindsets. And they were going to transform everyone else. And there were two presidents in particular who actually bought into this and were advocates. One was Teddy Roosevelt and the other one was Woodrow Wilson. And he was probably the biggest that I don't like human beings the way they are. I'm going to create a world where we have better human beings. And it didn't work. It didn't work. That's what got rid of alcohol. One of the things they went after was alcohol. Prohibition. Dean Jackson: Yeah. Dan Sullivan: Prohibition. And they created sort of this whole concept of the American way of life. And it was virtuous. It was moral. You cared for your neighbors, you were charitable, and you were comfortable, but you weren't lavish. And we're going to make the whole world like this. And we're going to watch everybody scrutinize everybody's behavior and give them little nudges and perhaps even bring in laws to regulate their behavior. Dean Jackson: Little nudges to get them in the Dan Sullivan: Right direction. Dean Jackson: I Dan Sullivan: Mean, we think we're going through it now, but it was nothing compared with the beginning of the 20th century. It was really a profound, profound movement. Yeah. Dean Jackson: Traditional values, right? I guess labeled under all those things. Dan Sullivan: Yeah. Made up traditional values. Dean Jackson: Exactly. Yeah, yeah. Labels. That's Dan Sullivan: Funny. Hollywood was the one that really created the American way of life. This was in the 30s and there was this whole series of Judy Garland and Mickey Rooney films. And the father was usually a judge. He was a judge and they had beautiful ... They had beautifully kept lawns and there was everything. And that was a pure creation of Hollywood. And the phrase, the American way of life actually doesn't date too prior to the 1930s. I mean, it wasn't there when the founders did it in the 1700s. It wasn't there in the 19th century through the 1800s. It didn't really arise until the 1930s. Dean Jackson: Isn't that interesting? When you think about the ... But that's when that was the multiplier of spreading a common vision, Dan Sullivan: Where Dean Jackson: You first got to see something that you could plant in the minds of many, many people asynchronously at a distance. Yeah, radioism. Yeah, because otherwise you would have had to go to a play or go to see something live to spread that out. It's very interesting. Yeah. Dan Sullivan: Yeah. But Dean Jackson: It's so funny. Dan Sullivan: It was something that people aspired to because they weren't actually living ... They didn't have that lifestyle. So it was an aspirational like that. It wasn't really supported by too many people who actually did that, but they had certain controls over the media. Dean Jackson: And that's a really good extension of what's happening now is that everybody has access to spread those visions. I've been ... Two things over the last little while, probably since last time we talked is I've consciously sort of opted out of paying attention to anything news related in any way, really. No, I'm the least aware of what's going on, just vaguely on the periphery of the things that are happening, but I'm also realizing- Dan Sullivan: It's good that you have me in your life so that I can give you a full report if you need Dean Jackson: To. Exactly. But even you, I don't get the sense that ... I mean, I don't know. Is that a part of your ... I mean, you're going to your real clear ... Dan Sullivan: Politics. Yeah. Dean Jackson: Yeah. So you are kind of keeping on top of the daily briefings or whatever. Is that an important- Dan Sullivan: Yeah. Well, I mean, there's some big issues which are ... It's mostly an American-centric world, like the war in Iran and of course the removal of illegal immigrants in the United States and making it difficult for people to use airports because they closed down the funding for TSA. I mean, I keep track of the latest storms and floods and everything like that. So yeah, I keep track of it, but I have sort of a contextual approach to it. I mean, it's kind of like, which way do things seem to be moving? And yeah, so there's some big shifts going, but there's always big shifts going on. If you checked in once a month, that would be sufficient. Dean Jackson: That's the way I'm feeling that it's ... Yeah, when you realize how little of it actually affects my day to day, it's something. And I've been ... Now this is ... I'm coming up on, I would say over a hundred days now of phone fasting of the 10 till- That's Dan Sullivan: Terrific. Dean Jackson: ... till noon. Yeah. And I would say that 80%, there's certain days where there are certain exceptions like today where we talk right before noon, so it's a Dan Sullivan: Little Dean Jackson: Bit earlier. And then when I have events going on or whatever, those are outlier days. But on the days that I am in control of the things, the standard day, that's the standard routine, is the

    1hr 5min
  6. Ep170: Thinking What You Think, Liking What You Like

    1 APR

    Ep170: Thinking What You Think, Liking What You Like

    In this episode of Welcome to Cloudlandia, Dean and Dan open with a candid reflection on how the spread of AI is making authentic human presence feel more valuable, not less. From the small signal of Dean wearing an analog watch and missing the daylight savings change, to Dan observing the quiet shift happening in his own sense of discretion about how he spends his time, the conversation quickly finds its footing. They discuss how AI has democratized capability while leaving vision as the truly scarce resource, and why keeping a human in the loop between yourself and the technology may be the smartest positioning for entrepreneurs right now. The conversation moves through a rich detour on the making of Casablanca, a film nobody wanted to make, staffed by a rotating cast of writers and second-choice actors, that became an all-time classic through trial and error. This leads Dan and Dean into a broader discussion about Rick Rubin’s approach to music production: knowing what you like and being decisive about it, without needing technical ability. Dan connects this back to Strategic Coach and the idea that his thinking tools have always been an expression of thinking about his own thinking. His upcoming quarterly book, Who We’re Looking For, promises to capture exactly that kind of self-aware entrepreneurial identity. Dean closes with a sharp framework for evaluating the past: the distinction between “could have,” “would have,” and “should have”, and why only one of those carries real emotional charge. He ties it back to their running thread on guessing and betting, suggesting that the people who will win in the next decade are those who can look forward with clarity about what they are uniquely suited to do. This episode is a good one for any entrepreneur who wants to think more clearly about where their real advantage lies. SHOW HIGHLIGHTS As AI democratizes capability, vision becomes the scarce resource — and knowing what you want is worth more than knowing how to do it. Dan’s rule for technology and teamwork: only engage if it makes you better at what you’re already uniquely good at. Casablanca became a masterpiece by accident, rotating writers, second-choice actors, and a studio that just needed a film for Tuesday. Rick Rubin has produced some of the most celebrated music in history without being able to play an instrument, his edge is knowing what he likes and being decisive. Dean’s framework for evaluating past decisions: “could have” acknowledges options, “would have” shifts blame outward, and “should have” is the only one with real emotional weight. The next decade belongs to people who think what they think, like what they like, and do what they do best, because those are the bets most likely to pay off. 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: I'm here. I'm here. Dean Jackson: Okay. There You go Dan Sullivan: I can get about 10, 15 seconds of you preparing to focus on the next hour. Dean Jackson: You can? Okay. Dan Sullivan: Yeah. Yeah. I can hear packages crumbling. I can hear ... Dean Jackson: Things are getting in order here, moving Dean Jackson: Yeah. Dan Sullivan: Little bit of backstage before we get the front stage. I think that adds authenticity to the podcast. Flavor. Flavor. So Dean Jackson: They know it's real. Dan Sullivan: It's Dean Jackson: Not AI Dan and AI Dean talking. Dan Sullivan: So here's a question for you. Do you notice yourself becoming more human the more AI becomes pervasive? Dean Jackson: Yeah. It's the way. Dan Sullivan: In other words, real lationship. Dean Jackson: Yes. I think you're absolutely right.That's what I'm really noticing. It was a very interesting thing. This morning I went over to the cafe. I have to leave a little earlier because at 11, we do our podcast, but what had happened was I put a watch on today that I is an analog watch. Dan Sullivan: So it didn't account for the time change. Dean Jackson: Daylight savings. Exactly. Dan Sullivan: Yeah. Dean Jackson: And then I got in my car and I realized, oh my goodness. I haven't accounted for the time. That's funny. Dan Sullivan: Yeah, you're- Dean Jackson: How would we know, right? Our bodies don't know. It's so ... Dan Sullivan: Yeah. Well, I noticed coming to Chicago, so I'm in Chicago today. And I really noticed the impact of daylight savings time because Chicago is right at the beginning, the new time zone. I mean, the time zone I'm in all the way for Chicago and Dallas are in the same time zone. Yeah. But Dallas would be very, very late in the time zone. Chicago's very early. So I noticed it. I don't notice it that much in Toronto because Toronto is more in the second half of the Eastern time zone. And so I don't notice the difference, but I was really struck. There's two things. One is you wake up. We slept in almost till seven this morning, seven o'clock, which would have been eight o'clock in Toronto. But on a travel day, my end of day sense of time gets a little bit screwed up, especially when I've moved from one time zone to the other. So we usually get to bed later. So we didn't get to bed till 10:30 Chicago time. And we went eight and a half hours. I slept eight. I was in bed eight and a half hours. I never sleep eight and a half hours. But boy, it was really bright. But then the jets start taking off and landing at seven Dean Jackson: O'clock. Dan Sullivan: And we're right in the flight zone for O'Hare. They literally come right over our house. Yeah. Dean Jackson: Well, it's Dan Sullivan: So Dean Jackson: Convenient for Strategic Coach, but ... Dan Sullivan: Oh yeah. Dean Jackson: Yes. I get it. Not so good Dan Sullivan: For Dean Jackson: Morning sleeping. Dan Sullivan: That was a series of happy accidents actually. We had been looking ... When we first got here, we used hotels, but they've got to the point where we had ... When you reach about 400 quarterly, you have 400 people come. Yeah. 400 coming. Then you want to switch over from paying for hotels to having your own conference center. So that's our number is about 400. And for example, we're not there yet in Los Angeles. We're not to the 400 mark. And there's no good solution to Los Angeles because the state taxes you, the county taxes you. Oh Dean Jackson: Yeah. Dan Sullivan: And where we do our workshops in Los Angeles, it's the division between two municipalities. Part of the hotel is in Venice, and the other part of the hotel is in Santa Monica, and they both tax you. Dean Jackson: Yeah, that's crazy. Dan Sullivan: Yeah. Yeah. So we would never have- Dean Jackson: Where Dan Sullivan: Is that? Where is it? Dean Jackson: Yeah. Where is the hotel in Santa Monica? Dan Sullivan: Well, it's right on Ocean Boulevard. So it's on the main drag in Ocean Boulevard, but we're ... You know where sort of the park is that has all the palm trees? Yeah. Yeah. Well, we're further south than that. We're probably a quarter of a mile south of the ... Dean Jackson: Like the Lowe's hotel there? Dan Sullivan: Just one hotel further, one for hotel further Lowe's. And so anyway, but it's really interesting. I mean, first of all, California being what it is right now, we would never have an office in Los Angeles like we have in Chicago because for lots of reasons. Chicago really works because we're right across from the runways at O'Hare, so it works really well. And our home, we're about 15 minutes from the airport from our home, so it's good. Yeah. Yeah. But we're right in the flight path and not much you can do about flight paths. Dean Jackson: That's true. Unless you're Donald Trump, get them diverted. Dan Sullivan: Well, they don't fly over his home in- Dean Jackson: It was an interesting joke. Dan Sullivan: It wasn't a joke. It wasn't a joke. It was a real thing. Dean Jackson: Oh, okay. Dan Sullivan: Yeah. Conrad Black told the story. Dean Jackson: What's the official story then? Because I've heard- Dan Sullivan: Well, the story is when he moved into Mar-a-Lago and it took him a long time to get ... That was contested because the people of Palm Beach, whoever, the influential people in Palm Beach, they did not want Donald Trump in Palm Beach. So I think it took him ... I'd just be picking a number out of the air here, but I think it was five or six years before he could actually get ownership. And the other thing is it was ... Mar-Lago was something that was going to be torn down and divided into a lot of different new homes because it's like a hundred rooms in Mar-a-Lago and it's from the early 20th century. And so- The Dean Jackson: Gilded age. Yeah. Dan Sullivan: Yeah. Yeah. It was a gilded age mansion. And so they disagreed with that because a lot of them are invested in real estate themselves. And that, I mean, the value of that property, because it goes from the inner waterway, what's that called? To Dean Jackson: The ocean, the inner coastal. Dan Sullivan: So it goes right from the intercoastal right across the main street and it has the beach too that goes right to the Atlantic. So I mean, just a prime piece of property. I mean, what that property would be worth is enormous. And so he got it, and then he noticed when he finally moved in, that planes from the local airport would fly right across his house. And he says, "Well, we got to stop that. I want to get a ruling that they can't fly over my house." And they said, "That's the flight path, that's the flight path." And he says, "Well, how could I stop that being the flight path?" And they said, "Well, you could be elected president of the United States." Dean Jackson: Okay, done. Dan Sullivan: Note to self. Dean Jackson: Hold my beer, as they Dan Sullivan: Say. Yeah. Dean Jackson: Okay. Hold my beer. I'll be right back. Dan Sulliv

    54 min
  7. Ep169: Arguing With Time

    25 MAR

    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 into it.

    1hr 4min
  8. 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 was h

    1hr 5min

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