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  • Ep172: Secrets, Surveys, and 30-Year Bets

    Ep172: Secrets, Surveys, and 30-Year Bets
    2026/04/15
    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 時間 3 分
  • Ep171: The Inevitability System

    Ep171: The Inevitability System
    2026/04/08
    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 時間 5 分
  • Ep170: Thinking What You Think, Liking What You Like

    Ep170: Thinking What You Think, Liking What You Like
    2026/04/01
    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 分
  • Ep169: Arguing With Time

    Ep169: Arguing With Time
    2026/03/25
    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 時間 4 分
  • Ep168: Why Relationships Still Beat Algorithms

    Ep168: Why Relationships Still Beat Algorithms
    2026/03/18
    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...
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    1 時間 5 分
  • Ep167: Timing, AI, and Betting on Yourself

    Ep167: Timing, AI, and Betting on Yourself
    2026/03/11
    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 ...
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    1 時間 3 分
  • Ep166: The Great Yesterdays

    Ep166: The Great Yesterdays
    2026/02/18
    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 ...
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    58 分
  • Ep165: Creating Yesterday to Build Tomorrow

    Ep165: Creating Yesterday to Build Tomorrow
    2026/02/11
    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 ...
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