Episodes

  • Ep176: Thirty Years of Vectors

    Ep176: Thirty Years of Vectors
    Jun 17 2026
    In this episode of Welcome to Cloudlandia, these two longtime collaborators trace how small decisions compound over decades to build momentum. In this episode of Welcome to Cloudlandia we open with Dan's annual London trip and a look at how AI is quietly transforming entire industries the way automation once reshaped farming, freeing up labor for higher-value work decade after decade. Dan connects this to his MELT framework, the idea that money, energy, labor, and transportation are where AI's real impact lands rather than entertainment. The conversation moves naturally from continents to careers, showing how economic shifts and personal turning points follow surprisingly similar patterns. Dean shares the experience of rereading 30 years of personal journals, starting from entry number one in April 1996, months before he ever met Dan. He describes "vector changes," the moments a single conversation redirected his career path, from tennis to real estate to building a multimillion-dollar coaching business with his mentor Joe Stump. Dan adds his own distinction between guessing and betting, pointing out how rarely people back their predictions with actual stakes, a useful filter for evaluating advice in any business. I was struck by how a journal that started with no plan became, thirty years later, documented proof of patterns worth studying. Listen for the moment Dean finally explains what a vector really is. SHOW HIGHLIGHTS Dan argues AI's real economic impact isn't entertainment, it's reshaping money, energy, labor, and transportation, his "MELT" framework. Dean started journaling in April 1996, and on page 22 of journal number one, met Dan Sullivan for the first time. Dan's test for any prediction: ask if there's real money on the table. Most people are confident guessers but unwilling bettors. Cyrus McCormick's mechanical reaper let one farmer and a horse do the work of 14 men, a preview of what AI may do today. Dean calls career-changing conversations "vector changes" single moments that redirected him from tennis to real estate to coaching. Dean's partnership with mentor Joe Stumpf took their combined coaching business from a few million dollars a year to many times that. 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** Back from **Dan Sullivan** London. **Dean Jackson** Across the pond, yes. How was your trip? **Dan Sullivan** We had a terrific time. Yeah, we were gone from Sunday of one week until Thursday of the next. **Dean Jackson** Wow. **Dan Sullivan** So pretty good. **Dean Jackson** What annual trip is this? Because I know you go every year in May. **Dan Sullivan** Probably 19, 19 years. **Dean Jackson** Wow. **Dan Sullivan** Yeah. **Dean Jackson** Look at that. Well, there you go. Is it as you remember? It's pretty interesting because London, like all the cities has gone through a lot of change over the 19 years for sure. **Dan Sullivan** Yeah, but it's got 2000 years of history. It's the one thing that you're reminded of when you go to London. It's been a very important city for 20 centuries. I mean from the beginning it's because of its location and on the river, the Thames. And the Thames is a tidal river so the tide changes twice a day. It goes one way and then it goes the other way and that saved a lot of manpower, saved a lot of probably- All right. Hurry **Dean Jackson** Up, get it on, get it on the train. **Dan Sullivan** Yeah. It's just interesting. It's funny about five years ago, Babson and I did one of those hereditary tests where you're **Dean Jackson** Just coming from- I know, the DNA **Dan Sullivan** Test. Yeah. 23 and Me was, there's a number of them, but 23andMe was the one that we used. And growing up in my family, I mean we're all immigrants being Americans and we were told that we were equal quarters German, French, English and Irish. **Dean Jackson** Wow. **Dan Sullivan** When the test came back, it was 55% from London. **Dean Jackson** Oh, wow. **Dan Sullivan** Yeah. Which could have been German, French, Irish and English. **Dean Jackson** Right, right, exactly. **Dan Sullivan** It basically said that the biggest influence was from London and I went there 62 years ago and first time that I ever went to London was November of 64 where I made my outward bound trip. So that was in Scotland, but I spent two or three weeks in London before I went north. And it was a really dirty city back then because they were still recovering even 20 years later they were still recovering from the war. There was vast sections of the city that had to be completely rebuilt and they hadn't gotten around to cleaning anything up. So Whitehall was Black Hall. Oh **Dean Jackson** Boy, yes. **Dan Sullivan** All the government buildings were really dark and ...
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    59 mins
  • Ep175: Money, Scent, and the Art of the Did List

    Ep175: Money, Scent, and the Art of the Did List
    May 20 2026
    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 ...
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    1 hr and 4 mins
  • Ep174: Guessing, Betting, and the AI Attention Economy

    Ep174: Guessing, Betting, and the AI Attention Economy
    May 13 2026
    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 ...
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    1 hr and 6 mins
  • Ep173: Rules Over Insights: Time Sense and the Decider Role

    Ep173: Rules Over Insights: Time Sense and the Decider Role
    Apr 22 2026
    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 ...
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    56 mins
  • Ep172: Secrets, Surveys, and 30-Year Bets

    Ep172: Secrets, Surveys, and 30-Year Bets
    Apr 15 2026
    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 ...
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    1 hr and 3 mins
  • Ep171: The Inevitability System

    Ep171: The Inevitability System
    Apr 8 2026
    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...
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    1 hr and 5 mins
  • Ep170: Thinking What You Think, Liking What You Like

    Ep170: Thinking What You Think, Liking What You Like
    Apr 1 2026
    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 ...
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    54 mins
  • Ep169: Arguing With Time

    Ep169: Arguing With Time
    Mar 25 2026
    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...
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    1 hr and 4 mins