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Welcome to Cloudlandia

Welcome to Cloudlandia

By: 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.© 2026 Welcome to Cloudlandia
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
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