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

  1. Ep172: Secrets, Surveys, and 30-Year Bets

    4D AGO

    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

    1h 3m
  2. Ep171: The Inevitability System

    APR 8

    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

    1h 5m
  3. Ep170: Thinking What You Think, Liking What You Like

    APR 1

    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
  4. Ep169: Arguing With Time

    MAR 25

    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.

    1h 4m
  5. Ep168: Why Relationships Still Beat Algorithms

    MAR 18

    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

    1h 5m
  6. Ep167: Timing, AI, and Betting on Yourself

    MAR 11

    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, nine mile

    1h 3m
  7. Ep166: The Great Yesterdays

    FEB 18

    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 then you p

    58 min
  8. Ep165: Creating Yesterday to Build Tomorrow

    FEB 11

    Ep165: Creating Yesterday to Build Tomorrow

    In this episode of Welcome to Cloudlandia, we explore how changing fundamental time structures unlocks behavioral transformation that willpower alone can never achieve. Dean shares his 14-hour phone fasting experiment and the profound impact of creating inevitable constraints rather than relying on self-discipline. We discuss how raising decisions to the level of inevitability—physically locking your phone away—removes the constant negotiation with temptation. Dan introduces his new framework for productivity: making your purpose each day to create a great yesterday, shifting focus from anxiety-inducing future planning to confidence-building past accomplishment. We examine how AI accusations on social media reveal our default skepticism, why technology adds to life rather than eliminating existing solutions, and the critical difference between content and context in an AI-saturated world. The conversation moves through airport infrastructure decay, New York's political experiment, and why surgeons will always be humans using technology rather than replaced by it. This is a conversation about reclaiming attention, restructuring time, and recognizing that confidence comes from documented wins rather than optimistic projections. Whether you're struggling with digital distraction or seeking sustainable productivity systems, this episode offers practical frameworks grounded in real experimentation. SHOW HIGHLIGHTS Dean's 14-hour phone fasting creates inevitability through physical constraint, eliminating the need for willpower by making phone access impossible overnight. Dan's new productivity framework: "My purpose today is to create a great yesterday" shifts focus from future anxiety to past confidence. Behavioral change requires changing time structure first—Dan's 46-day experiment with creating great yesterdays eliminated his attention deficit entirely. Document accomplishments with "No did it" format to remind yourself what life would be like without each completed task. AI excels at content matching but struggles with context creation—the key differentiator for human creative and strategic thinking. Elon's management approach: weekly meetings asking "What did you accomplish?" interrogates the permanent record rather than optimistic future plans. Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com TRANSCRIPT (AI transcript provided as supporting material and may contain errors) Dean Jackson: Mr. Sullivan. Dan Sullivan: Yes, Mr. Jackson. I wonder if our calls are being recorded in China. I just wonder. I hope so. I hope so. And transcribed and transcribed. I'd like to see one of our transcriptions in Chinese idiograms. That's it. Exactly. So are you just- I would get it framed and put it on a wall. Dean Jackson: Oh, that's perfect. Are you just getting up or are you still up from the big party last night? Dan Sullivan: No, we had massage. We have a massage therapist that we've had since 1992. 1992. She comes to our house on Sundays. Yeah. Dean Jackson: Oh, that's fantastic. Dan Sullivan: Yeah. Yeah. Yeah. Well, that's great. Dean Jackson: So how was- Dan Sullivan: We don't have the ideal climate that you enjoy at the Four Seasons. Valhalla. Valhalla. But we try to make up for it with other dimensions. Dean Jackson: That's right. The little built-in spa. Dan Sullivan: Yeah. Dean Jackson: Well, that's fantastic. So the party was a big success? Dan Sullivan: That was great. Dean Jackson: Yeah. Yeah. Had Bob's birthday party. Dan Sullivan: Yeah, it was great. Yeah, we had a restaurant. We took it over for ... Restaurants will have private parties and you take over the whole restaurant. And it's right at Front and Bay Street, just almost across from Union Station. And it's Peruvian Japanese fusion. Just shows you what people are putting together these days. And it was great. It was great. And our entire involvement was just showing up. Dean Jackson: Yes. I love that. That's the best. Dan Sullivan: Yeah. And Mark Young and his son were there and David Haase and Lindsay came. And Pete Warrell was here. He came ... Yeah. Richard and Lisa. Richard and Lisa were there. And so a lot of people traveled quite a distance to get there. So it was really great. Yeah. Dean Jackson: Absolutely. Oh, that's awesome. Yeah. I was texting with Richard Rossi yesterday. Dan Sullivan: After 12:00. After 12 o'clock noon. Dean Jackson: That's exactly right. Dan, I am a converse. Dan Sullivan: You're a new man. You're a new man. You're a new man. Dean Jackson: I am. I mean, this is a new normal. It's such a ... I'm realizing what a difference this phone fasting is. It's the best thing that I've ever done for productivity and just the ... I don't know. It's like the brain chemistry. I can feel it renewing. It's something like it's probably not unlike chronic inflammation from dopamine dripping constantly to the repairing of that from now the slow ... I'm manufacturing my own dopamine by really getting into my own brain. Dan Sullivan: Yeah. It's really interesting. I mean, over the years, because I've been continually creating thinking tools for entrepreneurs to look at things from a different perspective. But my feeling is that you can't make other behavioral changes unless you change a time structure, that there has to be a fundamental change of a time structure. And if you change a time structure, then all sorts of things can happen just because of that fact. And you've changed a 14 hour time structure in your life. Dean Jackson: Yeah. Give me some other examples because that's the first time I've heard you say that. So when you say the changing the time structures, what- Dan Sullivan: Yeah. Well, a simple example would just be that you have three different kinds of days. You have free days days and buffer days. And that immediately changes how you'd get work done. It changes what was sort of an off day. People say, "Yeah, well, I'm taking a day off." But in fact, they did business on their day off. I used to give this example. I said, everybody probably has come across the concept of Neapolitan ice cream. They used to come in the square package Dean Jackson: And then Dan Sullivan: You- Dean Jackson: Yeah, it's one of my favorites. Yeah. Dan Sullivan: And then if you took the cardboard away that protected, it was just this beautiful block. There was chocolate, vanilla, and strawberry. And then for some reason you forgot about it and you went away for three or four hours and you came back and it was just neopolitan soup. And which turns out to be chocolate. All things default to chocolate. Like if strawberry and vanilla and chocolate melt, what you have is a lighter shade of chocolate. Dean Jackson: Okay. That's interesting. Dan Sullivan: And everything gets mixed up with everything else and there's no structure, there's no distinction among your days. And I think you don't get rejuvenated. You're not very productive. And I just think everything falls apart when you mix different kinds of time structure, but you've created a very fundamental 14 hour structure right in from the end of one day to the middle of the next day. And so your brain just reorganizes everything just because you created that structure. Dean Jackson: Yes. I'm noticing it for sure. And yeah, it's a profound change. So I'm very excited about that. That's a good progress. Like that's one of my main things that I see looking at. What I've discovered in that, in reflecting on it, like why that works so well is that I've raised it to the level of inevitability. And we talk about that as like the apex ... That's the apex predator of certainty, is that when I put my phone in the lockbox, I've created an environment where it's inevitable that I'm not going to look at my phone for 14 hours because I can't. It's physically not possible for me to look at my phone because it's in the box. So I've eliminated the option, no willpower required. Like if I brought it and I put it in my bag and I went to the cafe or I went to whatever I'm sitting in the courtyard here and I had the phone inside the door in another room, there's still the siren song of the promise of dopamine or the fear of missing out or the something would draw me inevitably to check the phone and then you've reset the ... Dan Sullivan: A growling or a whimpering dog Dean Jackson: In Dan Sullivan: The next room. Dean Jackson: Yep. Dan Sullivan: Yeah. Dean Jackson: That's exactly right. Dan Sullivan: And you can't concentrate on anything else because it's drawing your attention. Yeah. Dean Jackson: Yeah. Dan Sullivan: Yeah. And maybe I could just look for five minutes, maybe Dean Jackson: .That's what I say. You start rationalizing, right? Yeah. Dan Sullivan: Yeah. Dean Jackson: You start rationalizing and negotiating the things. There's something to it because I was overlaying that with the thought of creating a better past and that- Dan Sullivan: So I've got a question for you and this is a big idea that I'm presenting. What if tomorrow the whole world decided to do what you're doing and that- How great would that be? No, but what would happen to the world economy? Dean Jackson: I wonder. I wonder. I mean, I guess it would ruin my breakfast plans. What? If I couldn't go to Honeycomb and get breakfast, if everybody else is closed. No, Dan Sullivan: Not closed. Their phone was off for breaking hours. Oh, I think that's it. Not that they weren't doing everything else, it's just that they're phone. Oh, got it. What do you think? Dean Jackson: I mean, I think it would be- It Dan Sullivan: Would certainly change online marketing. Dean Jackson: Yeah, absolutely it would. But I think that then people would ... I think it just condenses it. I look at the first thing, within 10 minutes of turning on my phone, by 12:10, I'm completely caught up on anything that I missed. First of all, I check my text messages. That's the thing that you'll see the notif

    1h 2m
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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
    166
  • Rating
    Explicit
  • Copyright
    © 2026 Welcome to Cloudlandia
  • Show Website
    Welcome to Cloudlandia

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