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Protecting what you've built, revisiting where you started, and betting on the systems that have never let you down.
In this episode of Welcome to Cloudlandia, Dan and Dean open with a riff on the strange new logic of secrecy in the internet age, where the best way to protect an idea may be to share it widely. Dan's story about a platform speaker who borrowed his Free Days, Focus Days, and Buffer Days framework without credit turns into a sharp point: the internet has made intellectual property both more fragile and more defensible at the same time. Dean connects this to his Nine Word Email and the way naming an idea is often the most durable form of ownership.
Dean then pulls out journal number one, dated April 1996, thirty years ago this week, and the conversation becomes a time capsule. He walks through his early real estate licensing business, Toronto and Beyond, and how the same playbook he used then to generate leads in Halton Hills is still running today in Winter Haven, Florida. Dan reflects on his own 25-year journaling project that began after a difficult 1978, and shares that his massage therapist of 34 years recently confirmed his physical condition hasn't changed since they started.
The episode closes on a larger canvas: real estate as a measure of civilization, the Louisiana Purchase at 50 cents an acre, Canadian politics, AI-driven job creation, and the quiet argument that the best protection against an uncertain future is a system that has already worked across three decades.
SHOW HIGHLIGHTS
Dan Sullivan's Free Days, Focus Days, and Buffer Days framework was stolen by a speaker mid-presentation and the audience corrected him before he finished the sentence. Seth Godin's counterintuitive take: before the internet, you kept secrets by hiding them; now you protect them by telling everyone first. Dean Jackson's Nine Word Email became famous globally and naming it was the single act that made it impossible for anyone else to claim it. The same lead-generation playbook Dean built in 1996 for Halton Hills real estate still works today, running virtually unchanged in Winter Haven, Florida. Dan's massage therapist of 34 years told him his physical condition is no different now in his 80s than when they first started working together. For every job eliminated by AI and robotics over the next 15 years, Dan estimates roughly two new jobs will be created,most of them in the legal and regulatory pushback against AI itself.
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean Jackson:
Welcome to Cloudlandia. Mr. Sullivan.
Dan Sullivan:
Yes. And AI will know about this call. Probably never.
Dean Jackson:
Probably
Dan Sullivan:
Never. It'll be scandalized. It'll be confused.
Dean Jackson:
Yes. This is the closest to analog. It's like, how did those spies meet in the trip down to our bathing suits neck deep in the ocean, having no wires, nobody listening. That's what
Dan Sullivan:
We're
Dean Jackson:
Having right now.
Dan Sullivan:
Yeah. There's a great story about Reagan, President Reagan. And when he got in, there was a particular situation where it was very clear that the Russians, the Soviets at that time,
Dean Jackson:
Were
Dan Sullivan:
Stealing American secrets.
Dean Jackson:
Very sneaky.
Dan Sullivan:
And Reagan had an interesting response to it. He said, "You know what we ought to do? Every so often, maybe every six months, we should collect every single secret in the United States and put them in 747s, cargo planes, 747 cargo planes, and fly them all to Moscow and dump them on the runway and fly off. And every six months we just dump all our secrets on the runway." He said, "The sheer confusion that that will cause will destroy the Soviet Union in a matter of a couple of years."
Dean Jackson:
That's funny, isn't it? Yeah. There's something interesting. Yeah. It's so funny, right? The things that we want to keep secret seem to be more desirable than the things we're willing to share. It's so-
Dan Sullivan:
Yeah. Just share everything. The way to destroy them. Actually, Seth Godin had a great line. He said, "Before the internet, the way to keep a secret secret was to keep it secret."
Dean Jackson:
Yes.
Dan Sullivan:
He says, "The way after the internet to protect your secrets is tell everybody your secret."
Dean Jackson:
Yeah. Oh, Dan, I can't tell you. So how many times the ... I created this thing called the nine word email. And the best thing I did was name it. And it's become known everywhere. And everybody who tries to present that idea as an original or as a, "Hey, here's this thing I've been working on. " Every single time in the comments is, "Oh, that's Dean Jackson's idea or that. " But predominantly, most people start out with the, "Here's an idea I learned from Dean Jackson." And then they talk about the nine word email.
Dan Sullivan:
Yeah. Well, I had a similar experience with the entrepreneurial time system, which is free focus and buffer days. So
There was a very famous platform speaker. This is probably 1995 and he's in, I think it's somewhere in Texas, I think San Antonio, and he's giving a talk and it's to financial advisors. It's to mainly real estate and financial advisors, couple thousand in the audience. And he said, "I want to tell you about my time system. I've created this new time system." And he says, "It's called Free Days Focus Days and Buffer Days." And the words were not even out of his mouth and about 10 hands come up and people stand up and said, "That's not your time system, that's Dan Sullivan's time system." So I have spies in the audience and we immediately get phone calls afterwards telling us about this event, this situation. And about a week later, I get a phone call from the speaker himself and he said, "Boy, you have a bunch of pit bulls for clients." And he tells me the whole story and I don't let on that I know the story.
I don't let on at all. I just say, "Oh, that's interesting." And I said, so he tells me about it and he says, "Who knows where ideas come from?" And I says, "Well, I'll give you a phone number. It's my IP lawyer and he'll tell you where this idea comes from." Yeah,
Dean Jackson:
I'll tell you
Dan Sullivan:
Where
Dean Jackson:
This one comes from.
Dan Sullivan:
Exactly. I don't know about other God origin ideas, but I can tell you where this one comes from. And he says, "Well, I'm really sorry about this. " He said, "I don't want to be in your bad books." And I said, "Well, you're not ... " I said, "Well, you're not in my bad books, but let me ask you a question. How did the rest of the speech go?
Dean Jackson:
" Exactly. Yeah, that's funny. Threw him off his game for sure.
Dan Sullivan:
And I said, "If there's 2000 people in the audience, those 2000 people are going to tell, each of them is going to tell 50 other people about what just happened." So I said, "I don't know what your marketing strategy was here, but I said, I don't think it's going in the direction you wanted it to.
Dean Jackson:
" Right. That's so funny. And now it's really ... It is interesting that everything now is kind of, we have this public record of the internet, like when somebody talks about something on a podcast that's timestamped or posts about it or publishes something and now on the blockchain even, like what Carrie Oberbrunner is doing with the instant-
Dan Sullivan:
Instant
Dean Jackson:
IP of just putting something up and at least, I don't know whether it's been tested or held up. But you look at it either way, it's certainly, it's a level of protection that has not been available. Exactly.
Dan Sullivan:
And the whole thing is that all IP law is based on timing who did it first. It's not who created it first, it's who applied for intellectual property first.
Dean Jackson:
Yes, exactly. Stick their claim to it. And that's where, kudos to Carrie for thinking that through and using a new technology of the blockchain to be able to instantly ... I mean, it's the digital equivalent or a much improved thing of mailing something to yourself with a registered letter and not opening it. That's a really ...
Dan Sullivan:
Yeah, that actually works. Yeah. That actually works. Yeah. I mean, a lot of people, I said that here's the thing, you got an idea, make a copy of it, put it in a letter, go to the post office and register the letter and have it sent to yourself and don't open it, don't open it. I mean, you can write on the outside of the letter what it relates to so you know which one. And if you present this in a legal situation, it will be accepted as timestamp proof.
Dean Jackson:
Exactly. Yeah. So I think that's pretty great. Now that's where we're headed there. I had something very interesting.
Dan Sullivan:
Can I mention something? Sure. If you're willing and we'll receive a communication, Kathy Davis, of Strategic Coach, would like to talk to you about actually being the chairperson for a panel at CoachCon.
Dean Jackson:
Oh, okay, perfect. I love it. That would be
Dan Sullivan:
Fantastic. Yeah. So I'll tell her this, I'm looking at my watch right here, it's 11:09 and on Easter Sunday that I actually passed on the word that you will receive a communication tomorrow
Dean Jackson:
From
Dan Sullivan:
Kathy Davis. And I just want to establish this proof that I actually passed out the message.
Dean Jackson:
Okay. Yeah, there we go. Timestamped. 11:10.
Dan Sullivan:
Timestamped.
Dean Jackson:
11:10 AM, Eastern Daylight Time. Yeah.
Dan Sullivan:
Yeah. So if you get a communication from her, when you get beyond noon tomorrow, you will know what it's all about.
Dean Jackson:
Oh, I can't wait. I can't wait. Yeah, I'm looking forward to it. It's coming up less than 60 days, right? Till Coach Kong. That's exciting. So I was looking, Dan, today, April 5th, yesterday was the date of the first entry in journal number one of wha
The most productive stretch of your life probably isn’t waiting for motivation, it’s waiting for the right constraint.
In this episode of Welcome to Cloudlandia, we follow Dean’s hundred-day phone fasting experiment locking his phone away from 10 AM to noon and what it revealed about the power of inevitability. Dean calls this his most consistently productive stretch ever, and Dan predicts that by the one-year mark, at least 20 other habits will have quietly shifted as a side effect. The big lesson: willpower is unnecessary when you design a system that removes the other options entirely.
Dan shares that he’s now at day 116 of his ‘Creating Great Yesterdays’ practice and is finishing a new quarterly book, Yesterday Creates Tomorrow. He also makes a sharp case for proactive health investment twice-yearly full bloodwork, AI-assisted cancer detection, and taking personal ownership of your body rather than waiting for the system to catch something at stage four. The conversation moves into the language of regret, where Dan breaks down why ‘should,’ ‘would,’ and ‘could’ are manipulation words and how reframing your past experience as a source of lessons removes its power over you.
The episode closes with a great business story from a Free Zone client: while every gas station in Washington State started charging for bathroom access, he went the other way, free bathrooms for everyone and created lineups of grateful customers who paid double out of sheer relief. It’s the kind of counterintuitive move that’s easy to describe and hard to execute, which is what makes it worth hearing about. This one’s got a few moments you’ll want to replay.
SHOW HIGHLIGHTS
Dean’s 100-day phone fasting experiment, locking his device away from 10 AM to noon, produced what he calls the most productive stretch of his entire life.
Dan’s prediction: by the one-year mark, at least 20 other habits will have changed as a quiet side effect of the phone fasting discipline.
The willpower myth, debunked: Dean’s biggest transferable lesson is that the system does the work when you engineer inevitability and remove all other options.
A Free Zone client turned Washington State’s ‘pay $20 before you can use the bathroom’ rule into a competitive advantage, by being the only gas station that didn’t charge.
Dan on why ‘should,’ ‘would,’ and ‘could’ aren’t grammar, they’re manipulation tools used to distort your relationship with the past.
AI is now detecting cancer predisposition three years before convergence happens. Dan’s case for twice-yearly blood panels: 20 extra healthy years for anyone willing to pay attention.
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean Jackson:
Welcome to Cloudlandia. Mr. Sullivan.
Dan Sullivan:
Good morning.
Dean Jackson:
Welcome to Cloudlandia.
Dan Sullivan:
Yes. I'm feeling it. I'm feeling the impact of Cloudlandia.
Dean Jackson:
I love that. There's always a home for us here in Cloudlanvia.
Dan Sullivan:
Yes. It's
Dean Jackson:
Our third
Dan Sullivan:
Space. Yeah. Well, yeah. And it's custom designed.
Dean Jackson:
That's exactly right.
Dan Sullivan:
It's custom design.
Dean Jackson:
You know when I say that, that's a really interesting thing, our third place, because that's how Starbucks, that was the intention of Starbucks when they got started as a third place between work and home, somewhere where you go to meet people and have great conversation. It's so funny because they've completely moved away from that. Now with the drive-throughs and the ... I described the interior spaces of the new coffee places as prison cafeteria style. It's like get your stuff and move along. Don't see them.
Dan Sullivan:
Yeah. Well, they went through a period, I think it's trying to think about a 10-year period where they were preaching to you, trying to make you a better person. And that didn't work. Don't have a goal in selling any product of transforming human nature. It's one of my- Observable. It's one of my firm foundational stones. Humans are going to do what humans are going to do and don't try to create a better human being. Just give them a little caffeine jolt and some sugar and they're okay.
Dean Jackson:
Observable life lessons. That's
Dan Sullivan:
Exactly right. Yeah. Yeah. Yeah.
Dean Jackson:
It's so funny.
Dan Sullivan:
Yeah. I think that's really the big thing now because this was actually ... I read an interesting book and it's called The Progressive Era in American History. And it starts kind of, I would say probably right after the Civil War. And it was a middle class. It was like people who lived in nice neighborhoods and they had nice things. And they made it their goal that their responsibility in life was to look at anywhere in America that didn't look like their neighborhood, didn't have their mindsets. And they were going to transform everyone else. And there were two presidents in particular who actually bought into this and were advocates. One was Teddy Roosevelt and the other one was Woodrow Wilson. And he was probably the biggest that I don't like human beings the way they are. I'm going to create a world where we have better human beings.
And it didn't work. It didn't work. That's what got rid of alcohol. One of the things they went after was alcohol. Prohibition.
Dean Jackson:
Yeah.
Dan Sullivan:
Prohibition. And they created sort of this whole concept of the American way of life. And it was virtuous. It was moral. You cared for your neighbors, you were charitable, and you were comfortable, but you weren't lavish. And we're going to make the whole world like this. And we're going to watch everybody scrutinize everybody's behavior and give them little nudges and perhaps even bring in laws to regulate their behavior.
Dean Jackson:
Little nudges to get them in the
Dan Sullivan:
Right direction.
Dean Jackson:
I
Dan Sullivan:
Mean, we think we're going through it now, but it was nothing compared with the beginning of the 20th century. It was really a profound, profound movement. Yeah.
Dean Jackson:
Traditional values, right? I guess labeled under all those things.
Dan Sullivan:
Yeah. Made up traditional values.
Dean Jackson:
Exactly. Yeah, yeah. Labels. That's
Dan Sullivan:
Funny.
Hollywood was the one that really created the American way of life. This was in the 30s and there was this whole series of Judy Garland and Mickey Rooney films. And the father was usually a judge. He was a judge and they had beautiful ... They had beautifully kept lawns and there was everything. And that was a pure creation of Hollywood. And the phrase, the American way of life actually doesn't date too prior to the 1930s. I mean, it wasn't there when the founders did it in the 1700s. It wasn't there in the 19th century through the 1800s. It didn't really arise until the 1930s.
Dean Jackson:
Isn't that interesting? When you think about the ... But that's when that was the multiplier of spreading a common vision,
Dan Sullivan:
Where
Dean Jackson:
You first got to see something that you could plant in the minds of many, many people asynchronously at a distance. Yeah, radioism. Yeah, because otherwise you would have had to go to a play or go to see something live to spread that out. It's very interesting. Yeah.
Dan Sullivan:
Yeah. But
Dean Jackson:
It's so funny.
Dan Sullivan:
It was something that people aspired to because they weren't actually living ... They didn't have that lifestyle. So it was an aspirational like that. It wasn't really supported by too many people who actually did that, but they had certain controls over the media.
Dean Jackson:
And that's a really good extension of what's happening now is that everybody has access to spread those visions. I've been ... Two things over the last little while, probably since last time we talked is I've consciously sort of opted out of paying attention to anything news related in any way, really. No, I'm the least aware of what's going on, just vaguely on the periphery of the things that are happening, but I'm also realizing-
Dan Sullivan:
It's good that you have me in your life so that I can give you a full report if you need
Dean Jackson:
To. Exactly. But even you, I don't get the sense that ... I mean, I don't know. Is that a part of your ... I mean, you're going to your real clear ...
Dan Sullivan:
Politics. Yeah.
Dean Jackson:
Yeah. So you are kind of keeping on top of the daily briefings or whatever. Is that an important-
Dan Sullivan:
Yeah. Well, I mean, there's some big issues which are ... It's mostly an American-centric world, like the war in Iran and of course the removal of illegal immigrants in the United States and making it difficult for people to use airports because they closed down the funding for TSA. I mean, I keep track of the latest storms and floods and everything like that. So yeah, I keep track of it, but I have sort of a contextual approach to it. I mean, it's kind of like, which way do things seem to be moving? And yeah, so there's some big shifts going, but there's always big shifts going on. If you checked in once a month, that would be sufficient.
Dean Jackson:
That's the way I'm feeling that it's ... Yeah, when you realize how little of it actually affects my day to day, it's something. And I've been ... Now this is ... I'm coming up on, I would say over a hundred days now of phone fasting of the 10 till- That's
Dan Sullivan:
Terrific.
Dean Jackson:
... till noon. Yeah. And I would say that 80%, there's certain days where there are certain exceptions like today where we talk right before noon, so it's a
Dan Sullivan:
Little
Dean Jackson:
Bit earlier. And then when I have events going on or whatever, those are outlier days. But on the days that I am in control of the things, the standard day, that's the standard routine, is the phone goes in at 10 and it comes out at noon. And it's been a game changer.
In this episode of Welcome to Cloudlandia, Dean and Dan open with a candid reflection on how the spread of AI is making authentic human presence feel more valuable, not less. From the small signal of Dean wearing an analog watch and missing the daylight savings change, to Dan observing the quiet shift happening in his own sense of discretion about how he spends his time, the conversation quickly finds its footing. They discuss how AI has democratized capability while leaving vision as the truly scarce resource, and why keeping a human in the loop between yourself and the technology may be the smartest positioning for entrepreneurs right now.
The conversation moves through a rich detour on the making of Casablanca, a film nobody wanted to make, staffed by a rotating cast of writers and second-choice actors, that became an all-time classic through trial and error. This leads Dan and Dean into a broader discussion about Rick Rubin’s approach to music production: knowing what you like and being decisive about it, without needing technical ability. Dan connects this back to Strategic Coach and the idea that his thinking tools have always been an expression of thinking about his own thinking. His upcoming quarterly book, Who We’re Looking For, promises to capture exactly that kind of self-aware entrepreneurial identity.
Dean closes with a sharp framework for evaluating the past: the distinction between “could have,” “would have,” and “should have”, and why only one of those carries real emotional charge. He ties it back to their running thread on guessing and betting, suggesting that the people who will win in the next decade are those who can look forward with clarity about what they are uniquely suited to do. This episode is a good one for any entrepreneur who wants to think more clearly about where their real advantage lies.
SHOW HIGHLIGHTS
As AI democratizes capability, vision becomes the scarce resource — and knowing what you want is worth more than knowing how to do it.
Dan’s rule for technology and teamwork: only engage if it makes you better at what you’re already uniquely good at.
Casablanca became a masterpiece by accident, rotating writers, second-choice actors, and a studio that just needed a film for Tuesday.
Rick Rubin has produced some of the most celebrated music in history without being able to play an instrument, his edge is knowing what he likes and being decisive.
Dean’s framework for evaluating past decisions: “could have” acknowledges options, “would have” shifts blame outward, and “should have” is the only one with real emotional weight.
The next decade belongs to people who think what they think, like what they like, and do what they do best, because those are the bets most likely to pay off.
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean Jackson:
Welcome to Cloudlandia. Mr. Sullivan.
Dan Sullivan:
I'm here. I'm here.
Dean Jackson:
Okay. There You go
Dan Sullivan:
I can get about 10, 15 seconds of you preparing to focus on the next hour.
Dean Jackson:
You can? Okay.
Dan Sullivan:
Yeah. Yeah. I can hear packages crumbling. I can hear ...
Dean Jackson:
Things are getting in order here, moving
Dean Jackson:
Yeah.
Dan Sullivan:
Little bit of backstage before we get the front stage. I think that adds authenticity to the podcast. Flavor. Flavor. So
Dean Jackson:
They know it's real.
Dan Sullivan:
It's
Dean Jackson:
Not AI Dan and AI Dean talking.
Dan Sullivan:
So here's a question for you. Do you notice yourself becoming more human the more AI becomes pervasive?
Dean Jackson:
Yeah. It's the way.
Dan Sullivan:
In other words, real lationship.
Dean Jackson:
Yes. I think you're absolutely right.That's what I'm really noticing. It was a very interesting thing. This morning I went over to the cafe. I have to leave a little earlier because at 11, we do our podcast, but what had happened was I put a watch on today that I is an analog watch.
Dan Sullivan:
So it didn't account for the time change.
Dean Jackson:
Daylight savings. Exactly.
Dan Sullivan:
Yeah.
Dean Jackson:
And then I got in my car and I realized, oh my goodness. I haven't accounted for the time. That's funny.
Dan Sullivan:
Yeah, you're-
Dean Jackson:
How would we know, right? Our bodies don't know. It's so ...
Dan Sullivan:
Yeah. Well, I noticed coming to Chicago, so I'm in Chicago today. And I really noticed the impact of daylight savings time because Chicago is right at the beginning, the new time zone. I mean, the time zone I'm in all the way for Chicago and Dallas are in the same time zone. Yeah. But Dallas would be very, very late in the time zone. Chicago's very early. So I noticed it. I don't notice it that much in Toronto because Toronto is more in the second half of the Eastern time zone. And so I don't notice the difference, but I was really struck. There's two things. One is you wake up. We slept in almost till seven this morning, seven o'clock, which would have been eight o'clock in Toronto. But on a travel day, my end of day sense of time gets a little bit screwed up, especially when I've moved from one time zone to the other.
So we usually get to bed later. So we didn't get to bed till 10:30 Chicago time. And we went eight and a half hours. I slept eight. I was in bed eight and a half hours. I never sleep eight and a half hours.
But boy, it was really bright. But then the jets start taking off and landing at seven
Dean Jackson:
O'clock.
Dan Sullivan:
And we're right in the flight zone for O'Hare. They literally come right over our house. Yeah.
Dean Jackson:
Well, it's
Dan Sullivan:
So
Dean Jackson:
Convenient for Strategic Coach, but ...
Dan Sullivan:
Oh yeah.
Dean Jackson:
Yes. I get it. Not so good
Dan Sullivan:
For
Dean Jackson:
Morning sleeping.
Dan Sullivan:
That was a series of happy accidents actually. We had been looking ... When we first got here, we used hotels, but they've got to the point where we had ... When you reach about 400 quarterly, you have 400 people come. Yeah. 400 coming. Then you want to switch over from paying for hotels to having your own conference center. So that's our number is about 400. And for example, we're not there yet in Los Angeles. We're not to the 400 mark. And there's no good solution to Los Angeles because the state taxes you, the county taxes you. Oh
Dean Jackson:
Yeah.
Dan Sullivan:
And where we do our workshops in Los Angeles, it's the division between two municipalities. Part of the hotel is in Venice, and the other part of the hotel is in Santa Monica, and they both tax you.
Dean Jackson:
Yeah, that's crazy.
Dan Sullivan:
Yeah. Yeah. So we would never have-
Dean Jackson:
Where
Dan Sullivan:
Is that? Where is it?
Dean Jackson:
Yeah. Where is the hotel in Santa Monica?
Dan Sullivan:
Well, it's right on Ocean Boulevard. So it's on the main drag in Ocean Boulevard, but we're ... You know where sort of the park is that has all the palm trees? Yeah. Yeah. Well, we're further south than that. We're probably a quarter of a mile south of the ...
Dean Jackson:
Like the Lowe's hotel there?
Dan Sullivan:
Just one hotel further, one for hotel further Lowe's. And so anyway, but it's really interesting. I mean, first of all, California being what it is right now, we would never have an office in Los Angeles like we have in Chicago because for lots of reasons. Chicago really works because we're right across from the runways at O'Hare, so it works really well. And our home, we're about 15 minutes from the airport from our home, so it's good. Yeah. Yeah. But we're right in the flight path and not much you can do about flight paths.
Dean Jackson:
That's true. Unless you're Donald Trump, get them diverted.
Dan Sullivan:
Well, they don't fly over his home in-
Dean Jackson:
It was an interesting joke.
Dan Sullivan:
It wasn't a joke. It wasn't a joke. It was a real thing.
Dean Jackson:
Oh, okay.
Dan Sullivan:
Yeah. Conrad Black told the story.
Dean Jackson:
What's the official story then? Because I've heard-
Dan Sullivan:
Well, the story is when he moved into Mar-a-Lago and it took him a long time to get ... That was contested because the people of Palm Beach, whoever, the influential people in Palm Beach, they did not want Donald Trump in Palm Beach. So I think it took him ... I'd just be picking a number out of the air here, but I think it was five or six years before he could actually get ownership. And the other thing is it was ... Mar-Lago was something that was going to be torn down and divided into a lot of different new homes because it's like a hundred rooms in Mar-a-Lago and it's from the early 20th century. And so- The
Dean Jackson:
Gilded age. Yeah.
Dan Sullivan:
Yeah. Yeah. It was a gilded age mansion. And so they disagreed with that because a lot of them are invested in real estate themselves. And that, I mean, the value of that property, because it goes from the inner waterway, what's that called? To
Dean Jackson:
The ocean, the inner coastal.
Dan Sullivan:
So it goes right from the intercoastal right across the main street and it has the beach too that goes right to the Atlantic. So I mean, just a prime piece of property. I mean, what that property would be worth is enormous. And so he got it, and then he noticed when he finally moved in, that planes from the local airport would fly right across his house. And he says, "Well, we got to stop that. I want to get a ruling that they can't fly over my house." And they said, "That's the flight path, that's the flight path." And he says, "Well, how could I stop that being the flight path?" And they said, "Well, you could be elected president of the United States."
Dean Jackson:
Okay, done.
Dan Sullivan:
Note to self.
Dean Jackson:
Hold my beer, as they
Dan Sullivan:
Say. Yeah.
Dean Jackson:
Okay. Hold my beer. I'll be right back.
Dan Sullivan:
Yeah. It's like the president of Venezuela sa
Every conversation has the potential to reveal something useful hidden within the ordinary, and this one delivers several of those moments.
In this episode of Welcome to Cloudlandia, we catch up after Dan's 11th trip to Buenos Aires for his ongoing stem cell treatments, where he shares a remarkable milestone: a 12% increase in brain volume over three years, roughly equivalent to reversing 30 years of cognitive decline. The conversation flows naturally into Dean's growing practice of "phone fasting" and constraining his available hours, and how that's led to a heightened clarity about where attention actually goes each day.
We then dig into the idea of "creating a better past", the practice of making today worth remembering tomorrow, and how this connects to calendar structure, scheduling disciplines, and the real cost of vague future planning. Dan shares why he treats his schedule as a commitment rather than a suggestion, and why words like "should," "would," and "could" are blame-shifting words that quietly block learning and behavior change. Dean's shift to locking in six months of workshops in advance gives a concrete example of how structure actually creates freedom.
The episode closes on a thought worth sitting with: Dan's observation that at the bottom of all unhappiness, there's an argument with time. The conversation between these two has a way of making the abstract feel immediately actionable, worth your full attention.
SHOW HIGHLIGHTS
Dan increased his brain volume by 12% in three years through stem cell treatments, equivalent to reversing roughly 30 years of cognitive decline.
Only 0.05% of people are proactively using AI to create output, meaning the competitive advantage window for early adopters remains wide open.
Strategic Coach's 250 thinking tools stay permanently "upstream" from AI, because AI can only work with what humans have already created and published.
Dan eliminated "should," "would," and "could" from his vocabulary entirely, calling them blame-shifting words that signal complaint without any intention to change behavior.
Dean locked in six full months of workshops in advance for the first time, discovering that visible structure on the calendar creates bookings, and momentum that vague future planning never could.
Dan's rule for unhappiness: at the bottom of every persistent dissatisfaction, you'll find someone having an unwinnable argument with time.
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean:
Welcome to Claudelandia. Mr. Sullivan. There he is. Are you in Argentina?
Dan:
Nope, nope.
Dean:
No, I'm
Dan:
Back in Toronto. No, we arrived about noon yesterday. We got back. Yeah.
Dean:
Okay. Joe is on his way.
Dan:
Yep. Yep. He left last night.
Dean:
Well, he didn't leave last night actually. Well, he missed his connection. So that's a problem. Yeah, hopefully he figured it out, but he was definitely on the ... We're not happy till you're not happy airline experience program.
Dan:
Yeah.
Dean:
So Garnet and Shirley, they were on the flight that took off. He was so frustrated. Yeah, he was so frustrated because he was on the runway or on the ramp and they were just taken off, so he missed just barely.
Dan:
You know, people are not necessarily talk about Joe, but I noticed a lot of people are throughout their entire life, they're about three hours late.
Dean:
Oh, just missed. Yeah, exactly.
Dan:
Yeah. Yeah. And if they just take one future event or one present event out of their life, they'd be on time, but there's always one thing that makes them three hours late.
Dean:
That's funny.
Dan:
Yeah.
Dean:
So you're in Toronto now?
Dan:
Yeah, just got back. Yeah. Yeah.
Dean:
Perfect.
Dan:
And the snow is starting to melt.
Dean:
Okay. That's what I hear.
Dan:
That's
Dean:
What I hear. You can see the light at the end of the tunnel.
Dan:
Yeah. Yeah. The power went out in our neighborhood last night. Suddenly it was just completely black, but at our house, five seconds later, the generator kicked in and we had full lights, electricity. Everything was working.
Dean:
Oh, see?
Dan:
Yeah.
Dean:
That's why you get a generator, right?
Dan:
Yep. Yep. Yep. Yep. Yep.
Dean:
Because that's like doing an experience transformer in advance.
Dan:
Yeah.
Dean:
Looking forward.
Dan:
I remember a New Yorker cartoon a long time ago, 30, 35 years. And it shows this elderly couple standing at a corner in New York City, a street corner. And right in the middle of the intersection is a dead elephant.
Dean:
Oh my.
Dan:
And the wife, the older lady is saying to her husband, "Elmer, I'm never going to complain about you bringing that elephant gun with you on a date."
Dean:
Oh my goodness. That's so funny. Better, safe than sorry.
Dan:
You never know when the elephant's going to show up.
Dean:
That's exactly right. Better to have the gun and not need it. Oh
Dan:
Yeah. Yeah. Yeah. It may be socially awkward, but you never know when you're going to need that elephant gun.
Dean:
I love it. So this is-
Dan:
This is our 11th trip to Buenos Aires.
Dean:
So what's the progress report?
Dan:
Yeah. Well, it's interesting because I'm the oldest patient that they've ever had at this clinic who's doing this procedure where you're replacing a cartilage and it's completely back. But what they've discovered is that it's a very young cartilage. It's an early life cartridge, which is okay if you're 13 pounds.
Dean:
Right.
Dan:
Yeah. But I weigh more than 13 pounds. And so it's a brand new cartilage. It's completely back. So if I do an MRI lying down, it's completely back. But if I do an MRI with me standing with my full weight, it's as if nothing's happened yet.
Dean:
Oh, really? And that's ... Well, what's the protocol for that too?
Dan:
It's kind of a gelatin that they put into the knee now, and it gradually kind of creates a structure in there. I think this is from the cosmetic world, where they put this in people's
Dean:
Cheeks or they- Wharton's jelly or whatever. Is that what you're talking about or is that
Dan:
Something that- Yeah, something like that. But gradually it'll reinforce the growth. My cartilage is growing at a much faster pace than a six month old baby would be. Yeah. And the pain is less. I
Dean:
Was just going to say, what's the practical thing?
Dan:
I would say if I compare to a week now, a seven day experience to seven days before I went for my first treatment, which was November of 19 to 2023, so it's two and a half years, basically. My pain is down somewhere between 80 and 90%.
Dean:
Oh, that's awesome. And that's really-
Dan:
Yeah. Yeah. I mean, pain is the problem.
Dean:
Well, there you go.
Dan:
Well,
Dean:
That's
Dan:
Just the knee, but the big
Dean:
One
Dan:
Has been the brain. I mean, by far the biggest impact because they do it on my knee for cartilage purposes. They do it on both my ankles because I have Achilles tendons, broken Achilles tendons in both of my ankles, and they're good. They're good. They're better. There's more flexibility, more push off. But the big one has been the stem cells to the brain, and I've increased my brain volume by 12% in three years.
Dean:
12%.
Dan:
12%. I mean,
Dean:
That's great. And
Dan:
That's about 30 years. That's equal to about 30 years of decline.
Dean:
Wow.
Dan:
So I would be ...
Dean:
Basically,
Dan:
I'm back where I was when I was 52.
Dean:
Brain wise.
Dan:
Being 82 right now. And I notice it. I notice it too.
Dean:
You do? What do you notice? Like your brain feels more limber and alive?
Dan:
No, the biggest thing is that the world makes sense.
Dean:
Okay. Okay. That's
Dan:
Interesting. The entire world now is suffering from Trump to arrangement syndrome.
Dean:
Oh my goodness. Yeah. It's so ... Yeah, it really is. I think consciously-
Dan:
He's taken on a historically unique role where there's nobody who's indifferent to him.
Dean:
Right. Exactly.
Dan:
There's no in between.
Dean:
Yeah. I mean, it's really ... Yeah, this is ... It's funny because with my phone fasting and my zone of my 12:00 PM till 6:00 PM is really because I'm constraining the available time that I have to meet with people, that those times are filling up. So I really have very little time to pay attention to what's going on. Like just at a tippy top level, I know that we've bombed Iraq or Iran, sorry. But that's really ... I have not ... I've escaped really all of the other ... Just cursorily or peripherally, I've seen things about Dubai and the Emirates and stuff
Dan:
Like that. Well, I think because it was a war, it's a war. So people say, "Well, he's causing a war." Actually, the war has been going on for 49 years, but it's only been from one side. So the Iranians, the Mulas, the whatever they are, declared war on the United States in 1979, but it was only
Dean:
In
Dan:
2026 that an American president noticed it. And he said, "Oh, you can't do that.
Dean:
" Yeah. Wait a minute.
Dan:
Wait a minute. Yeah. I knew I had an itch there. I didn't know what it was. So why don't we make this quick? We'll just destroy your entire leadership in the first half hour.
Dean:
Okay. There we go. Reset.
Dan:
There we go. There we go. You tried to get our attention. It took you 49 years, but you got our attention and here it is. Yeah.
Dean:
Yeah. So I look at that for me as ...
Dan:
Sure.
Dean:
That's been a noticeable difference is just- Well, that's
Dan:
Great.
Dean:
... general awareness.
Dan:
And I don't think you've deprived the world of anything by not paying attention to it.
Dean:
No, because I think you said it when you gave up TV, you made the observation that there's a lot better things going on in your brain than our in that. And for me, I'm realizing that exact same thing. I've been really loading up a large language model in my brain of being exposed to so much stuff now. And yeah, so now it's really building the interface to tap into it. That's in the
AI is producing more content than ever, but the competition for real human attention has never been fiercer, and no algorithm is going to change that.
In this episode of Welcome to Cloudlandia, we open with Dean noticing a new kind of AI fatigue, the creeping discomfort of scrolling through feeds filled with emotionally manipulative, AI-generated content designed to mimic reality. Dan adds his own observation: the UN’s push to centrally control AI development, which he sees as less a threat and more an unintentional comedy. From there, the conversation gets into the economics of attention, Dean’s framing of 1,000 waking minutes per person per day as a fixed resource, and Dan’s eight years of recovered attention after cutting television (roughly 800 hours a year, or 100 full days).
We then work through the distinction between capability and ability, why giving everyone access to the same tools doesn’t level the playing field, any more than putting a grand piano in every home produces Billy Joel. Dan shares a striking data point from Strategic Coach: after 36 years in business, 85% of their 800 registrations last year still came through personal referral, no technology involved. That leads Dean to a new concept he’s developing called “REAL-ationships,” the coming premium on trust built with actual people as AI-generated mimicry becomes harder to distinguish from the real thing. Dan caps it with a sharp observation: technological mimicry is not emotionally satisfying, at least not after the first time.
This episode lands on a counterintuitive truth for any business owner: the more powerful AI gets at producing content at scale, the more valuable a genuine human relationship becomes. It's worth a listen.
SHOW HIGHLIGHTS
Dean identifies a new kind of AI fatigue—not from using it, but from being unable to escape emotionally manipulative AI-generated content in everyday feeds.
Dan recovered 800 hours of attention per year—equivalent to 100 full days—simply by cutting television eight years ago.
Everyone has 1,000 waking minutes per day; with roughly 450 already consumed by screen time, the real scarcity isn’t content—it’s attention.
Capability vs. ability: giving everyone a grand piano doesn’t produce Elton John—the qualitative edge still belongs to the person, not the tool.
After 36 years in business, 85% of Strategic Coach’s 800 annual registrations still come from personal referral—no technology involved.
Dean’s new concept “REAL-ationships”: as AI mimicry becomes undetectable, the value of trust built with a real person you know is only going to increase.
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean Jackson:
Welcome to Cloudlandia. Mr. Sullivan.
Dan Sullivan:
Mr. Jackson. Welcome to Cloudlandia
Dan Sullivan:
Yes. Welcome to Cloudlandia.
Dean Jackson:
So you know what's funny?
Dan Sullivan:
Is it getting congested?
Dean Jackson:
Oh, I realized, I think I've noticed that today or this week, I reached a level of AI fatigue that I'm noticing is a different sensation in that-
Dan Sullivan:
It's like the 18 mile mark of the marathon.
Dean Jackson:
I think that's true. I'll tell you what happened for me is that when I watch Reels or Instagram or Facebook, any of the things, what I'm noticing is the majority of the things that I'm seeing now are AI. And it's getting to where it's not as obvious that it's AI, but it is AI and you can tell that it's AI and it kind of is getting to where it's bothersome. And I realize that this is like we're seeing things, especially when they're trying to make things, they're using it now to create videos that tug on your heartstrings in a way like this family adopted this lion mother who laid her ... They fed the lion and now the lion brings back her cubs to meet the homeowners. And it's just so ridiculous. And everybody is ...
Dan Sullivan:
Yeah. And this is in Monica Beach, right? Yeah, exactly. It's near the Ferris wheel on Monica. Yeah.
Dean Jackson:
Santa Monica here. Right. Exactly. Santa
Dan Sullivan:
Monica. Santa Monica. Yeah.
Dean Jackson:
It's
Just so ... So I realize now, and the fact is that most people don't realize it. I mean, there's so much engagement and you start to see now how just all of these situations where people are being confronted or having arguments or what looks like ... This is where it becomes troublesome is the propaganda ones where they're showing confrontations or arguments between two people. Angry Karen does this or confronts this person or all these things where it's like ... I don't know. It's like ... I always say how Jerry Spence talked about that our minds are putting out their psychic tentacles, testing everything for truth, and it can detect the thin clank of the counterfeit. And I think that that's true, but I worry that many people's counterfeit detectors are not as tuned in as ours are. And I could see that.
Dan Sullivan:
Well, there's an old phrase that nobody was ever seduced to wasn't looking for sex.
Dean Jackson:
That's true. Yeah.
Dan Sullivan:
In other words, you've got to be looking for ... For them to have any impact, you have to be looking for ... I mean, to a certain extent, you're only subject to propaganda if you're looking to be propagandized. I
Dean Jackson:
Don't know.
Dan Sullivan:
It's kind of funny. I had a different AI experience this week, and I think mine is more a source of humor than yours is. Tell me. And that is that the Secretary General of the UN says now that the UN has to be in control of the development and the expansion and the use of AI to guarantee that there needs to be a centralized bureaucratic control AI, otherwise it will be misused. It will be misused. And I said, "If the right team of comedians will just sort of get on this UN thing of trying to control the AI, I think there's ... At least in the short term, there's some real humor here. You can get some real
Dean Jackson:
Humor
Dan Sullivan:
Of the UN as a thought and AI as a thought." I think if you put those two together, there's immediate jokes that you can come up with. They want three billion. Now, which country has three billion to get to the UN?
Dean Jackson:
I know one.
Dan Sullivan:
Anyway, because they want to distribute it, distribute, which requires bureaucrats to third world nations, so to make sure that they can bring themselves up to speed on AI. So I think this has got some comic possibilities.
Dean Jackson:
Oh, man. Yeah.
Dan Sullivan:
Where's Monty Python when we need them?
Dean Jackson:
Exactly. They've been canceled. They were canceled. That's what happens. We cancel everybody who's got common sense. I think I mentioned that I saw-
Dan Sullivan:
Can I ask you a question? Are you surprised that this is happening?
Dean Jackson:
I'm not surprised. I mean, if you look at it that we're not even two and a half years into it right now, and when you see the stuff that is escalating, like now the Claude bots are this becoming agentic AI, that's the new buzzword, that it acts on its own and can do ... It's like becomes an army of who's. It's like if you just track the trajectory of where this actually goes, like if you're really ... If we're at a point right now where video and audio is already there, but if you get to a point where video is indistinguishable, like undetectable difference, that's coming. We're moments away from that. And I have a friend who was just saying she had a call from a bot, like an AI thing that's calling realtors and the ... Shortly into the conversation asked ... Caleb was the guy who was talking.
She's like, "Caleb, are you a bot?" And then he admitted that he was a bot and then she kept him on the phone for 20 minutes because they hadn't safeguarded him. So she's getting all the, what he's trained to do, like how many and like 30% of the people don't clue in that he's a bot. And that's the truth. His mission was to call these agents, to have the conversation with them just to get the interest to book an appointment with the real person, right? So these are appointment setting bots. And he said that 30% of the people that they talk to don't clue in that it's an AI and they happily set an appointment. And then on the appointment, the human then is pitching this service of, "You didn't know it was a bot, so this is like you want to use this for your business." And I thought, wow, it's very ... Yeah, it's really, it's something where we are.
So I really don't know. And you and I, you and I are kind of once removed.
Dan Sullivan:
It's interesting. I put together an article and I actually sent it to Jeff Madoff and I said 10 AI issues that are going to become very quickly political and how each of the parties, the Democratic Party and the
Dean Jackson:
Republican
Dan Sullivan:
Party would respond to it. And once the interesting thing is that with all 10, they would respond differently. So it's going to be ... And they'll ... So they're going to have a different point of view. But I think that the moment that it becomes political, then it'll be like any other technology. It'll be like industrialization,
Dean Jackson:
It'll
Dan Sullivan:
Be like television, it'll be like radio. The moment it gets fully ... The political sector of society immediately engages with it, then you'll see that it'll become even more complicated and confusing and complex than it is right now because each of the parties is going to want to utilize AI for its own electoral reasons and to get information out. The one factor though is that our brain still can't concentrate on more than one thing at a time
Dean Jackson:
And
Dan Sullivan:
I don't think AI is going to make the least bit of difference of making humans be able to engage with more than one thing at a time.
Dean Jackson:
Oh yeah, yeah. No, that's the thing. I said that. I was having a conversation-
Dan Sullivan:
No, the speed of
The entrepreneurs quietly mastering AI right now won't make headlines, they'll just quietly take market share.
In this episode of Welcome to Cloudlandia, we trace how birth timing, access, and circumstance shape who becomes an outlier from Malcolm Gladwell's hockey birthday effect to how Bill Gates got his 10,000 hours on a mainframe. Dan connects those dots to today's college graduates, whose degrees have been quietly devalued as AI handles both entry-level tasks and executive scheduling. The generation that sidesteps that broken system and goes straight to mastering AI, Dan argues, is the Andre Agassi of our moment, getting an unfair head start while everyone else is still in line.
We shift into the mechanics of entrepreneurial success, where Dan introduces a new Free Zone tool: separating intentional wins from accidental ones. Some of your biggest breakthroughs, like Dean switching from professional tennis to real estate after watching a 15-year-old Andre Agassi dismantle a field, weren't planned, they were recognized in the moment. Dan also shares Day 75 of his 'Creating Great Yesterdays' practice, and how reframing ADD as emotional commitment to too many future possibilities at once finally gave him a way to work with it rather than against it.
What ties this conversation together is a quiet argument for building inevitability into your environment. Whether it's locking your phone in a box, structuring a Free Zone summit around a single tool, or recognizing when the game you're in no longer matches who you're becoming, the clearest wins come from making the right behavior the only option. This episode rewards multiple listens.
SHOW HIGHLIGHTS
The entrepreneurs quietly mastering AI won't complain — they'll just take market share while others are shouting about fairness.
Dan's "Creating Great Yesterdays" practice — now at day 75 — may be the most practical ADD hack you've never heard of.
Dean switched from professional tennis to real estate at 21 after watching Andre Agassi win his first pro tournament — timing changed everything.
Dan ran an entire Free Zone Summit day using just one tool — Guesses, Bets, and Payoffs — and calls it the best he's ever pulled off.
History isn't a roadmap — it's a record of everything people didn't expect. Dan on why anyone claiming to predict the future is probably selling something.
The Mr. Beast $400,000 weight-loss experiment and what it reveals about designing environments where success becomes inevitable, not optional.
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean:
Welcome to Cloudlandia. Mr. Sullivan.
Dan:
Mr. Jackson. Quality training. Quality training. I guess-
Dean:
For quality
Dan:
Purposes.
Dean:
That's why
Dan:
Everything
Dean:
Is recorded, right?
Dan:
I guess we need more of that, don't we? Quality training. Yeah.
Dean:
So you made it back?
Dan:
Yeah. It was unbelievable how we got back. Everything was exactly on time.
Dean:
Oh my goodness.
Dan:
Yeah. I put that date in the calendar.
Dean:
So they've abandoned their, we're not happy till you're not happy policy.
Dan:
Yeah. And in San Diego, they have this brand new terminal, which for a while anyway, is just devoted to Air Canada and Southwest Airlines. Oh, goodness.
Dean:
Wow.
Dan:
Yeah. Yeah. It's beautiful. I mean, beautifully designed.
Dean:
This is in San Diego? They have an Air Canada terminal?
Dan:
No, it's a brand new terminal. And for now, the only airlines are Air Canada and Southwest Airlines.
Dean:
Oh, okay. And this is in Toronto? No,
Dan:
San Diego.
Dean:
Oh, in San Diego. Yeah, yeah. Okay. That's surprising that the ...
Dan:
Yeah, it opened about six months ago. Oh,
Dean:
I like that.
Dan:
It's an extension of the main terminal, but for now. And for a moment in history, I don't know how long, but you just arrive and you walk in and Air Canada is right there. That's great.
Dean:
They
Dan:
Take the bags and then you just go to the left a little. And the clear line is we have clearer. And we walked straight through. Bags went straight through and really nice, very nice terminal. But the gate where we needed to be was right there. And the plane arrived on time and we got on time. It took off on time. And we got home a half hour early. I guess the jet stream was more powerful that night. And
Dean:
Everything is working. That's almost like just a few more of those and not going to erase the taste of your other
Dan:
Experience. Oh no, that was gone and then that was gone. Oh,
Dean:
Good. There you go.
Dan:
That was gone. I don't really hold onto it. I've
Dean:
Always
Dan:
Loved the- But I had been playing with a thought recently of not complaining when things don't work, but being excited when things do work. I think my chances of having things work are diminishing, big systems falling apart. And so I said, "I'm just going to take the attitude of anytime something does work, I'm just going to be excited about it.
Dean:
" That's great.
Dan:
Yeah.
Dean:
You're looking ... It's the Pigmalian effect. It's the positive expectation. That's good.
Dan:
Yeah. You
Dean:
Know what's ... The location-
Dan:
I don't understand Pygmalion. I'm thinking about my Fair Lady.
Dean:
Oh, well, there's a psychological principle called the Pygmalion Effect. And it was a study that they did with teachers where they would
Dan:
Tell
Dean:
The teacher that, "Oh, you've got Danny Sullivan, he's gifted. He's like really going places." And the teachers would subconsciously treat you like you're special and you've got real potential. And then they would tell other teachers that you are trouble and don't let you get away. You got to keep your eye on that, Danny Sullivan. He's a problem. Don't let him get away with anything. And in the studies, just subconsciously, the way the teachers treated you, you would outperform if you were treated like you're special and you would underperform if they thought you were a problem. And of course you just poor innocent Danny Sullivan, you weren't aware of it and you weren't doing anything different than you normally do, but the expectation of what your outcome was going to be was affected by the teachers. And I think that that's a good way to look at life.
It's along your lines of your eyes only see and your ears only hear what you're looking for, right?
Dan:
Yeah. Yeah. Yeah. Yeah. I don't think I ever had a difficult teacher. I had some really supportive ones. I can think about four over the 12 years that I was in school that zeroed in. Yeah. Yeah.
Dean:
I remember, so Mrs. Jefferson, my third grade teacher, if I look back on it, she was the one that identified that Dean is able to achieve excellent results with what seems like little effort. Imagine if he applied himself. She had a really smart way of doing things because she would ... I would get the work done quickly and then I would be talking to the other kids and she was ... One of the other comments was that I was a disturbing influence in the class, distracting the other kids when I was done. So she made me the ... I call it, she assigned me the role of the poet laureate for the class or whatever, but she would allow me, whenever I was done my work, she would give me one of these ... I remember the index card, like a nice size card print thing and these markers.
And she would allow me to draw and create something after I was done in exchange for not talking to the other kids. And I thought, wow, that was an interesting exchange. Giving me some other creative outlet without any expectation or whatever, here I am, that's 50 years later and I still,
That's a standout moment in my education.
Dan:
Yeah. Yeah. I think it's important to have one or two adults. I think one of the things that child psychology, that there's one or two adults that zero in on you as a child and takes interest and shows that they think you've got a big future coming. Yeah. I think that's important.
Dean:
Who was that for you?
Dan:
Well, I had a third grade teacher also. It was Ms. Miller who broke my heart because the next year she came back as Mrs. McConnell and I lost her. I lost her.
Dean:
Boy, oh boy.
Dan:
And then I think there was a seventh grade teacher and then there was an English teacher in high school and actually the school principal actually took a real interest in me. And that was important because ... I mean, in 1950s and '60s, college wasn't a big thing. It wasn't like you're getting your high school students ready for college.
And first of all, I was born in the generation that was smaller than the previous generations, and that was the first one. I was in the first American generation. It went from 28 to 46, 1928 to 1946. And consequently, there was more than enough of everything when you got to school. There was more than enough personal attention. When you got into out of school and you went into the marketplace, there was more than enough jobs, there was more than enough everything. So I think I had history, wasn't particular individuals. It was just the historical period. And if you look, basically that generation from achievement wealth ... Silicon Valley was actually created by that generation. Everybody talks about the baby boomers, but it was actually that generation that created Silicon Valley. It was the people who had been born because they were mostly too young to go into the war, the Second World War.
Like if you were born in 1928, when the war started, you were 13, so you didn't go into the war. And then they had that big expansion of college education with the GI Bill. And so there was a lot of emphasis on education and you just ... It was ... Remember the cartoon movie, Remembering Nemo, Finding Nemo. Yeah.
Dean:
Finding
Dan:
Nemo. Yeah. Yeah. There's that stream off east coast of Australia where if you get into the stream, you go like eight, nine miles an hour underwear. I kind
The way you structure your time shapes everything else, including who else can reach you, and when.
In this episode of Welcome to Cloudlandia, we get into two parallel time experiments that Dan and Dean are running, Dan's 70-day practice of using each day to "create a great yesterday," and Dean's intermittent phone fasting that divides the day into clear, protected zones. Dan traces the origin of his approach to a story from Leora Weinstein, who shifted his focus entirely from the uncertain future to building a reliable past, one day at a time. The result? His most productive December and January on record, and a measurable shift away from last-minute scrambling.
They also explore how abundance, whether it's 14 kinds of corn flakes or an infinite choice of tasks, can paralyze decision-making rather than free it. The conversation moves through Dan's "Upping Your Game" tool (an evolution of the A/B/C model), AI bots taking on their creators' personalities, the surprising legal and real estate ripple effects of data centers, and a listener book recommendation about the history of money. Dan makes the case that the real cure for future anxiety isn't better planning, it's higher consciousness in the present.
There's something almost game-like about committing to a better past each morning, and both Dan and Dean are finding that the scoreboard doesn't lie. This one's worth your time.
SHOW HIGHLIGHTS
Dan's 70-day "great yesterday" practice turned December and January into his most productive months ever.
Dean's intermittent phone fasting from 10 PM to noon creates four protected daily zones for deeper focus.
Future anxiety may simply be a symptom of low present consciousness, not a problem that better planning solves.
Dan's upgraded "Upping Your Game" tool helps identify which activities to eliminate, tolerate, or expand and where AI can step in as the "who."
An East German twin's paralysis in front of 14 varieties of cornflakes illustrates how abundance without criteria leads to retreat, not freedom.
AI chatbots tend to reflect the personality of the person who created them, including their blind spots and biases.
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean Jackson:
Welcome to Cloud Landia, Mr. Sullivan. Hello there. There he is. From the West Coast.
Dan Sullivan:
Yes, I am straight
Dean Jackson:
To Cloud Landia. Cloud Landia is accessible from all points.
Dan Sullivan:
Yes, yes. But where you're sending from does make a difference. So I had a question for you.
Dean Jackson:
Tell me
Dan Sullivan:
From your experience, because you've had both, what's worse, 23 degrees Fahrenheit in Orlando, or minus 10 degrees in Toronto?
Dean Jackson:
Well, I will tell you this, that it came to the point last week that I actually had to wear pants one day. And so yeah, there's that, which I don't prefer, but today is a beautiful, we're right back now up to, let's see, it's 71 and sunny, probably similar to what you have right this moment.
Dan Sullivan:
Yeah, we're probably there. Yeah, the door is open. I'm looking out at, it's a nice place. I don't know if you've ever been here. Which one? La Jolla. Estancia.
Dean Jackson:
Yes. I've been to Estancia. Yeah, it's very
Dan Sullivan:
Nice. Nice place. Yeah. Yeah. We gotten in here just about this time yesterday, just a casual afternoon. Went to a really nice place, Maxima, who was with you last week? Maxima. And we went to an old hotel called the Empress Hotel.
Dean Jackson:
I know where that is.
Dan Sullivan:
Really nice restaurant.
Dean Jackson:
Oh, that's great.
Dan Sullivan:
Yeah, it's good.
Dean Jackson:
So the crowd is gathering.
Dan Sullivan:
I don't know if any of the clients are in yet. Our team just came in. I was sitting in the lobby. Lobby. And so half our team. Yes,
Dean Jackson:
Please. When is the actual, so you are in La Jolla, California for the Free Zone Summit, and that is on Tuesday is the actual day?
Dan Sullivan:
Well, it really starts
Dean Jackson:
Monday night.
Dan Sullivan:
Well, it starts Monday afternoon because Mike Kix is going to put on an AI from three to five o'clock. And then,
Dean Jackson:
Oh, there you go.
Dan Sullivan:
Then the Pacific
Dean Jackson:
Starts right in his backyard.
Dan Sullivan:
Yeah. Pretty well. Pretty well. And he's going to use one of our tools for part of his presentation. We have, I don't know if you remember an old tool. It was called the A BC model, and the A represented activities that you find really irritating. You hate them.
Dan Sullivan:
Yes.
Dan Sullivan:
And B represents okay activities that you don't hate them, you don't love them, you're just doing them more or less as a matter of habit. But it takes up your time and attention, and then they see as fascinating and motivating. And then you apportion what amount of time do you think you're spending on A and also B, and also C right now, and then a year from now, where would you want your time allocation? But I changed it, upgraded it, and it's called Upping Your Game. And then you brainstorm for each of the three categories, and then you talk about the top three changes you're going to make with a top three for B and top three with C. And then Mike's going to show how that relates to ai, where AI is the who. Oh, I like that. Yeah. Yeah. So
Dean Jackson:
I like that. I mean, yeah, that's great. I always had to mix in my mind, we're used to A being the good thing and C being the less than thing. So I had to always flip that in my mind that the C is actually the good thing in this model, but the sentiment of it I love, and it's similar. It's like you could overlay the unique ability, unique ability, and the things you you're excellent at and the things you're,
Dan Sullivan:
And in some ways, that's almost the essence of coach. And so it's been a couple, it's simple, but not necessarily easy.
Dean Jackson:
That's the truth. That is the truth.
Dan Sullivan:
Simple. But not necessarily could be easy, but not necessarily.
Dean Jackson:
Yeah, it's easy. Yeah. It's nice when you look at it just to be crystal clear, right? That fits with your, I've been using your model of is there any way for me to get this result without doing anything? That would be the A plus for me of these. Right? And then, yeah, what's the least amount
Dan Sullivan:
That I, that's a model that's a little closer to where I am right now, that the a c model, I think the A, b, C model is about 15 years old. And the question, the three questions, I think is about two years. So one of them is repair of the past. The other one is it's sort of I'm not going to do anything in the future. Right, right, right. Yeah. I'm going to expand and grow and jump without me doing anything at all.
Dean Jackson:
That's even better with your mind. With your mind, yes. Prompting.
But I think that's the magic of that is knowing what you want, knowing that this is what I want, but is there any way for me to get it without doing anything? I think that's fantastic. So Max was here in Orlando at Celebration last week. We had a breakthrough blueprint, and we actually, we had about a half size group. We lost people that were stranded in North Carolina, the freeze in New Jersey, the deep freeze or whatever. One of they showed me it was a hundred car pile up in Charlotte, a hundred car pile up. I mean, you could see that's like the ice. Everybody's sliding into each other. That's kind of crazy. I don't prefer it. Every time that kind of stuff happens, it makes me more resolute in my snow free millennium
Dan Sullivan:
Commitment.
Dean Jackson:
I'm quite enjoying that. That's the right way to do it.
Dan Sullivan:
Yeah. Well, I think people are really built differently, but I so love the change of seasons that I wouldn't be tempted like La Jolla here. I mean, there isn't much here that would give you the kind of resistance that you would actually develop character.
Dean Jackson:
Well, the only thing Dan would be the traffic. The traffic trying to get out of La Jolla at any time in rush hour. But other than that, you don't have to leave La Jolla or get into it. It's perfection. Yeah,
Dan Sullivan:
I, I don't feel any of Newton's third law here, third law for every action, there's an opposite and equal. I'm just not getting the equal reaction here. It's just all easy. I mean, how can you develop character when everything's
Dean Jackson:
Just, well, you have to develop. What you have to do is develop the character in order to get to be there. That's the real thing. Somebody said that San Diego, especially LA and the coastal areas have gotten unreachable for average Americans or the things, and it's like my first thought was, well try harder. I mean, that's not, LA Jolla doesn't owe anybody anything to be affordable. Why
Dan Sullivan:
Now would you count $40 for bagel and Lve? Exactly. Choice. That was my choice. This morning. I said, I'd like to have the bagel and locks,
Dan Sullivan:
And
Dan Sullivan:
They said, well, it's a buffet. You can put together your own bagel and locks. But what if I just want the bagel and locks?
Dan Sullivan:
Doesn't matter
Dan Sullivan:
How much is, well, first of all, how much is the buffet? It's $40. And I says, well, what if I just want the bagel and Lux? It's 40.
Dean Jackson:
Right, exactly.
Dan Sullivan:
And it's not even bagel, it's actually Bagel Crisps. So they've taken a bagel and they've cut it into 10 pieces and crisp it.
Dean Jackson:
Okay.
Dan Sullivan:
But it's actually quite good. It's actually
Dean Jackson:
Good Melba toast in a way.
Dan Sullivan:
Yeah. It's like Melba toast, but it's bagel. It's got a nice taste to it. So I had five of them. I had five of them
Dean Jackson:
Get your money's worth.
Dan Sullivan:
I wasn't heavy on the locks. I had a big let or whatever they call 'em, a crisp. I had one of those. And then you put on the crea
In this episode of Welcome to Cloudlandia, we explore how changing fundamental time structures unlocks behavioral transformation that willpower alone can never achieve.
Dean shares his 14-hour phone fasting experiment and the profound impact of creating inevitable constraints rather than relying on self-discipline. We discuss how raising decisions to the level of inevitability—physically locking your phone away—removes the constant negotiation with temptation. Dan introduces his new framework for productivity: making your purpose each day to create a great yesterday, shifting focus from anxiety-inducing future planning to confidence-building past accomplishment.
We examine how AI accusations on social media reveal our default skepticism, why technology adds to life rather than eliminating existing solutions, and the critical difference between content and context in an AI-saturated world. The conversation moves through airport infrastructure decay, New York's political experiment, and why surgeons will always be humans using technology rather than replaced by it.
This is a conversation about reclaiming attention, restructuring time, and recognizing that confidence comes from documented wins rather than optimistic projections. Whether you're struggling with digital distraction or seeking sustainable productivity systems, this episode offers practical frameworks grounded in real experimentation.
SHOW HIGHLIGHTS
Dean's 14-hour phone fasting creates inevitability through physical constraint, eliminating the need for willpower by making phone access impossible overnight.
Dan's new productivity framework: "My purpose today is to create a great yesterday" shifts focus from future anxiety to past confidence.
Behavioral change requires changing time structure first—Dan's 46-day experiment with creating great yesterdays eliminated his attention deficit entirely.
Document accomplishments with "No did it" format to remind yourself what life would be like without each completed task.
AI excels at content matching but struggles with context creation—the key differentiator for human creative and strategic thinking.
Elon's management approach: weekly meetings asking "What did you accomplish?" interrogates the permanent record rather than optimistic future plans.
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean Jackson:
Mr. Sullivan.
Dan Sullivan:
Yes, Mr. Jackson. I wonder if our calls are being recorded in China. I just wonder. I hope so. I hope so. And transcribed and transcribed. I'd like to see one of our transcriptions in Chinese idiograms. That's it. Exactly. So are you just- I would get it framed and put it on a wall.
Dean Jackson:
Oh, that's perfect. Are you just getting up or are you still up from the big party last night?
Dan Sullivan:
No, we had massage. We have a massage therapist that we've had since 1992. 1992. She comes to our house on Sundays. Yeah.
Dean Jackson:
Oh, that's fantastic.
Dan Sullivan:
Yeah. Yeah. Yeah. Well, that's great.
Dean Jackson:
So how was-
Dan Sullivan:
We don't have the ideal climate that you enjoy at the Four Seasons. Valhalla. Valhalla. But we try to make up for it with other dimensions.
Dean Jackson:
That's right. The little built-in spa.
Dan Sullivan:
Yeah.
Dean Jackson:
Well, that's fantastic. So the party was a big success?
Dan Sullivan:
That was great.
Dean Jackson:
Yeah. Yeah. Had Bob's birthday party.
Dan Sullivan:
Yeah, it was great. Yeah, we had a restaurant. We took it over for ... Restaurants will have private parties and you take over the whole restaurant. And it's right at Front and Bay Street, just almost across from Union Station. And it's Peruvian Japanese fusion. Just shows you what people are putting together these days. And it was great. It was great. And our entire involvement was just showing up.
Dean Jackson:
Yes. I love that. That's the best.
Dan Sullivan:
Yeah. And Mark Young and his son were there and David Haase and Lindsay came. And Pete Warrell was here. He came ... Yeah. Richard and Lisa. Richard and Lisa were there. And so a lot of people traveled quite a distance to get there. So it was really great. Yeah.
Dean Jackson:
Absolutely. Oh, that's awesome. Yeah. I was texting with Richard Rossi yesterday.
Dan Sullivan:
After 12:00. After 12 o'clock noon.
Dean Jackson:
That's exactly right. Dan, I am a converse.
Dan Sullivan:
You're a new man. You're a new man. You're a new man.
Dean Jackson:
I am. I mean, this is a new normal. It's such a ... I'm realizing what a difference this phone fasting is. It's the best thing that I've ever done for productivity and just the ... I don't know. It's like the brain chemistry. I can feel it renewing. It's something like it's probably not unlike chronic inflammation from dopamine dripping constantly to the repairing of that from now the slow ... I'm manufacturing my own dopamine by really getting into my own brain.
Dan Sullivan:
Yeah. It's really interesting. I mean, over the years, because I've been continually creating thinking tools for entrepreneurs to look at things from a different perspective. But my feeling is that you can't make other behavioral changes unless you change a time structure, that there has to be a fundamental change of a time structure. And if you change a time structure, then all sorts of things can happen just because of that fact. And you've changed a 14 hour time structure in your life.
Dean Jackson:
Yeah. Give me some other examples because that's the first time I've heard you say that. So when you say the changing the time structures, what-
Dan Sullivan:
Yeah. Well, a simple example would just be that you have three different kinds of days. You have free days days and buffer days. And that immediately changes how you'd get work done. It changes what was sort of an off day. People say, "Yeah, well, I'm taking a day off." But in fact, they did business on their day off. I used to give this example. I said, everybody probably has come across the concept of Neapolitan ice cream. They used to come in the square package
Dean Jackson:
And then
Dan Sullivan:
You-
Dean Jackson:
Yeah, it's one of my favorites. Yeah.
Dan Sullivan:
And then if you took the cardboard away that protected, it was just this beautiful block. There was chocolate, vanilla, and strawberry. And then for some reason you forgot about it and you went away for three or four hours and you came back and it was just neopolitan soup. And which turns out to be chocolate. All things default to chocolate. Like if strawberry and vanilla and chocolate melt, what you have is a lighter shade of chocolate.
Dean Jackson:
Okay. That's interesting.
Dan Sullivan:
And everything gets mixed up with everything else and there's no structure, there's no distinction among your days. And I think you don't get rejuvenated. You're not very productive. And I just think everything falls apart when you mix different kinds of time structure, but you've created a very fundamental 14 hour structure right in from the end of one day to the middle of the next day. And so your brain just reorganizes everything just because you created that structure.
Dean Jackson:
Yes. I'm noticing it for sure. And yeah, it's a profound change. So I'm very excited about that. That's a good progress. Like that's one of my main things that I see looking at. What I've discovered in that, in reflecting on it, like why that works so well is that I've raised it to the level of inevitability. And we talk about that as like the apex ... That's the apex predator of certainty, is that when I put my phone in the lockbox, I've created an environment where it's inevitable that I'm not going to look at my phone for 14 hours because I can't. It's physically not possible for me to look at my phone because it's in the box. So I've eliminated the option, no willpower required. Like if I brought it and I put it in my bag and I went to the cafe or I went to whatever I'm sitting in the courtyard here and I had the phone inside the door in another room, there's still the siren song of the promise of dopamine or the fear of missing out or the something would draw me inevitably to check the phone and then you've reset the ...
Dan Sullivan:
A growling or a whimpering dog
Dean Jackson:
In
Dan Sullivan:
The next room.
Dean Jackson:
Yep.
Dan Sullivan:
Yeah.
Dean Jackson:
That's exactly right.
Dan Sullivan:
And you can't concentrate on anything else because it's drawing your attention. Yeah.
Dean Jackson:
Yeah.
Dan Sullivan:
Yeah. And maybe I could just look for five minutes, maybe
Dean Jackson:
.That's what I say. You start rationalizing, right? Yeah.
Dan Sullivan:
Yeah.
Dean Jackson:
You start rationalizing and negotiating the things. There's something to it because I was overlaying that with the thought of creating a better past and that-
Dan Sullivan:
So I've got a question for you and this is a big idea that I'm presenting. What if tomorrow the whole world decided to do what you're doing and that- How great would that be? No, but what would happen to the world economy?
Dean Jackson:
I wonder. I wonder. I mean, I guess it would ruin my breakfast plans. What? If I couldn't go to Honeycomb and get breakfast, if everybody else is closed. No,
Dan Sullivan:
Not closed. Their phone was off for breaking hours. Oh, I think that's it. Not that they weren't doing everything else, it's just that they're phone. Oh, got it. What do you think?
Dean Jackson:
I mean, I think it would be- It
Dan Sullivan:
Would certainly change online marketing.
Dean Jackson:
Yeah, absolutely it would. But I think that then people would ... I think it just condenses it. I look at the first thing, within 10 minutes of turning on my phone, by 12:10, I'm completely caught up on anything that I missed. First of all, I check my text messages. That's the thing that you'll see the notifications come on. You
In this episode of Welcome to Cloudlandia, Dean and Dan explore the rapid transformation happening at the intersection of AI, work, and human relationships. Dean shares insights from an AI marketing conference where attendees split into two camps—those excited by technical possibilities and those overwhelmed by the pace of change. The key insight? Focus on the "what" and "who" rather than getting lost in the "how," treating AI as a tool that handles the backstage work while humans shine in front-stage interactions.
The conversation takes a sobering turn as they examine how AI is fundamentally reshaping employment markets. Entry-level jobs are vanishing as companies choose AI over inexperienced workers, and the educational system continues training students for positions that may no longer exist. Dan shares a fascinating study showing how teachers' cognitive profiles have shifted dramatically toward fact-finding and rule-following—exactly the skills AI now replicates—while entrepreneurial thinking remains uniquely human.
They discuss the growing value of authenticity in an increasingly automated world, from the appeal of live podcasts to the irreplaceable nature of genuine human hospitality. Dan shares his successful framework for using strategic thinking in political campaigns, demonstrating how human connection and listening remain the foundation of influence. The episode concludes with a powerful observation: as AI attempts to take center stage, the real response will be a return to valuing live, in-person human experiences more than ever.
SHOW HIGHLIGHTS
Why creatives should focus on making the milk and let others handle the farming—how AI frees you to do only what you do best.
How AI is eliminating traditional first jobs and why the education system is preparing students for a future that no longer exists.
Dan's theater approach to AI—automating predictable backstage work to make human front-stage interactions more valuable and authentic.
How Ted Budd used Strategic Coach's Dangers, Opportunities, and Strengths framework to win a Senate seat, swinging the vote by 14 points
Why live podcasts and human hospitality are becoming more valuable as AI proliferates—people can detect "the thin clank of the counterfeit"s.
Dean's evolved creative process using AI to handle everything except the actual thinking—writing five thoughts weekly with minimal friction.
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. Hello there. There he is. How are you?
Dan Sullivan:
Good, good.
Dean Jackson:
There we go. Well, you are in Chicago now?
Dan Sullivan:
I'm in Chicago, yeah. Reasonably mild for this time of year. It's just a little bit above phrasing, still not too bad. Not too bad. Well,
Dean Jackson:
It's reasonably perfect here, just exactly at room temperature in the courtyard. Yeah. So there we go. You had a great week with the live 10 times talk podcast with Joe this week. That was good.
Speaker 3:
I think
Dean Jackson:
That there's a real pendulum swing right now in live, craving live and authentic and real stuff. It's a pretty interesting juxtaposition this week because I spoke at a conference on Monday and AI bought/marketing conference that Perry Belcher was holding in Orlando. So about 650 people there and it was just speaker after speaker sharing all the amazing things that are coming, that they're doing with generative AI and agentic AI, all the things. And we had a panel at the end of the day with all the speakers and I noticed two types of questions. It was open for Q&A. So people would come up to the mic and I noticed that there were technical people asking technical questions about the mechanics of how do you string together these syntax and using all this language of what the behind the scenes, the things that are making things happen.
Dean Jackson:
And then there were other people who came and were sort of like deer in headlights caught with feeling overwhelmed that they're in the wrong room, that they're so far behind, they'll never catch up. And it was really what struck me is it was, I said, the best thing if you're a creative person, a visionary in this, is the best thing you could really do is just pay attention to what they're doing, what's actually possible to get an idea of what the actual applications are and how you would see this working for you because that's what your strength is. And note who is doing these things and just focus on the what and the who and just completely bypass the how. Don't worry about how to do any of this. I said, this room is full of people who are ready and will do, which is see how it could apply.
Dean Jackson:
And that's a ...
Dan Sullivan:
I talked about about- Could you restate that? You blacked out for about five seconds there. Oh,
Dean Jackson:
Really? Okay. So
Dan Sullivan:
We didn't. It's what you said, the room is filled with people who know the how. You don't have to worry about the how.
Dean Jackson:
Yeah, that's exactly right. And I said, the thing is that I talked about the self-milking cow, that the biggest frustration is that sometimes the creatives are worrying about having to be a self-milking cow where they have to milk themselves and pasteurize it and package it and take it to market, all the things. Where if you just focus on making the milk, you can surround yourself by farmers and do all of that other stuff and just free yourself to be a cow. It was funny to see just the shoulders relax and you could hear the collective for those people, for the people in the room that were in that situation.
Dan Sullivan:
Yeah. Yeah. I've had the same experience talking to strategic coach clients. And I have it in the workshops, but not so much because the people in the workshops are there to think about their thinking about what they've been doing and what they're doing next. But when I'm in a more social setting, and in my case, it would be when I'm in one of our two main offices, Toronto or Chicago, and it's lunchtime and there are other coaches coaching the client. Then at lunchtime, I'm in the cafe and as many as eight or nine other people will come and join me for lunch. But the last three times that I did that, that was probably in December. The entire topic for the entire lunchtime hour was AI, which is interesting. I mean, to compare it a year back, it wouldn't have been that way a year ago.
Dan Sullivan:
So it's a topic that's grown in importance over the last year. And one of the groups was a first year group. They were just in their first year of strategic coach. And a woman asked me, she said, "How are you looking at this? " And I said, "Well, I take a theater approach to entrepreneurism, and that is that there's a backstage and there's a front stage." And I said that, "I think that what AI is allowing us to do is to increase the automation in the backstage so that we can make the front stage more and more human." So it's actually freeing humans up to be in the front stage and because there's so much that AI does, which is sort of predictable and repetitive work that's now using up the time and effort of backstage people and so we can free them up. So we put our emphasis on the interaction of engaging with people and that's largely unpredictable.
Dan Sullivan:
So unpredictable front stage, more predictable backstage. So that's been my approach to it so far. And it seems, first of all, it also has that relaxing impact that you talked about. I mean, it is amazing, but if everything's amazing, it stops being amazing.
Dean Jackson:
I think you're right. And the question I've been asking now, whenever I see these things or I hear people talking about their rather ... And people take pride in the way they've strung together all these agentic bots doing these complex workflows of things. But the question I've been asking both to myself and to them is to what end? That's the thing is I always have to think like, to what end is this? What is the outcome that we're attaching this to? Because a lot of it's just activity for activity's sake, content for content's sake, without really understanding like, how is this making the boat go faster? Is it improving the ability to get a result? And it's a very interesting thing when you work backwards from the outcome that you're looking for, as opposed to just working at the workflow. Everybody immediately assumes that more content is better and that more having ... I've noticed that the proliferation of clones, that's the big thing now, setting up your AI clone to create these videos for almost you.
Dean Jackson:
As Jerry Spence would say, we can all detect the thin clank of the counterfeit. And so it's not exactly as ... If you've got the chance to watch or to give your real life attention units to something that is not authentic, or you can be on a live 10 times talk podcast with you and Joe where you know 100% that it's real and it's you guys and there's like a real gathering of humans. There's a different energy to it.
Dan Sullivan:
Yeah. Yeah. I get that feeling. And the other thing for the people who are straining things together right now in January of 2026, how's it going to be any different in 2027? They're still going to be straining new things together, but have they produced everything to be different- Have they produced any breakthrough impact by their straining things together?
Dean Jackson:
Yeah. What's the result? That's the exact, that's the thing. That's what I always look at is that, to what end is this going to actually make a difference? I shared with you my new ... The process now of creating my five new thoughts a week of brainstorming the ... Today is come up with the idea day, and then through the week I'll write the five thoughts. And I'm finding this ... I'm just relaxing
In this episode of Welcome to Cloudlandia, Dan and Dean explore the intersection of personal transformation and rapid global change in our technology-driven world.
Dean reveals the profound results of his eight-week phone-in-the-box experiment, sharing how reclaiming 14 hours daily has restored his ability to read for extended periods and revolutionized his creative process. He discusses developing systematic approaches to manage ADHD, including mastering 50-minute focus sessions that consistently produce two fully-formed thought pieces. With Charlotte, his AI partner who can read his handwriting, Dean has created a sustainable rhythm for generating hundreds of insights annually.
Dan shares unexpected breakthroughs from his stem cell treatments—while the 50-year-old knee injury heals slowly, his cognitive testing has improved 90% and his reflexes have returned to levels he hasn't experienced in decades. He discusses upcoming book launches, including The Greater Game with John Bowen, featuring original entrepreneurial research and interactive dashboards, plus the innovative four-by-four casting tool being developed as their first licensed internet product.
The conversation shifts to examining how individual action amplified by technology can expose truth at remarkable speed. From Venezuela's Maduro being extracted to a Brooklyn jail cell to a lone citizen journalist uncovering $112 million in daycare fraud with just his phone and one day of investigation, we explore how Cloudlandia enables rapid revelation of hidden realities.
We close by reflecting on the philosophical nature of AI use—how billions of people are each creating entirely unique cognitive signatures with their AI tools, as distinctive as fingerprints yet largely invisible to the world. It's a fascinating look at how technology simultaneously democratizes capability while making individual creative processes more private than ever.
SHOW HIGHLIGHTS
Dean shares eight weeks of results from his daily experiment, revealing how eliminating phone access for 14 hours has fundamentally restored his ability to focus, dramatically improved his sleep scores, and brought back the hours-long reading sessions he thought he'd lost forever..
Dan reveals the surprising results from eight stem cell treatments—while his 50-year-old knee injury progresses slowly, his brain health has skyrocketed with 90% improvement in cognitive testing.
The remarkable story of Venezuela's Maduro—executed flawlessly in 30 minutes by Delta Force with 120 planes, no American casualties, and no equipment left behind.
Dan's theory that if you interviewed half the world's population, you'd find four billion people working on four billion different things with AI—each creating cognitive signatures as unique as fingerprints, largely undetectable and fundamentally private despite the connected world we inhabit.
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.
Dan Sullivan:
Mr. Jackson. How are you? Good, good. Had a great trip to London for-
Dean Jackson:
I didn't know you were going to London.
Dan Sullivan:
Yeah. Yeah. We just decided at the last moment, unfortunately, we got good flights and good rooms and some friends of ours from the DC area, they went and Steven Palter and his family were there. Oh,
Dean Jackson:
Nice.
Dan Sullivan:
So lots of great meals, lots of great place. Two out of three, which is good batting average. That gets you into Hall of Fame if you get two out of three. Exactly. Actually, if you get three out of 10, you've got a good chance.
Dean Jackson:
That's right.
Dan Sullivan:
If you play 20 years and have a 300 batting average, probably you're in consideration depending on
Dean Jackson:
Venture capital.
Dan Sullivan:
When the hits actually happened.
Dean Jackson:
Yeah. I got Babs texted on New Year's Eve and you guys were back from ... I didn't realize you were gone. Were you there for Christmas or after Christmas you went?
Dan Sullivan:
Yeah, we left on Christmas day night and flew overnight to London. And then boy, it was buzzing. London downtown doesn't matter what day it is, it's buzzing. Yeah. I just saw a video last night and it's one of these new AI films, which I think is really great where they'll take a sketch that was made of London 2000 years ago and then they'll animate it. And
Speaker 3:
It's
Dan Sullivan:
Really terrific. It's really terrific. For history buffs, it's terrific. I think this AI thing has uses. What do you think? I mean, are you noticing things that you wish you could have done five years ago more quickly? They're happening more quickly.
Dean Jackson:
Yeah. I'm working today on creating a better past. And the better past involves AI. Yeah. That's a really interesting thing. I watched over Christmas, there's a new series called Pluribus.
Dan Sullivan:
You described it on a previous session.
Dean Jackson:
Yeah. I was just fascinated. It wrapped up Christmas Eve.
Dan Sullivan:
What is it? A final six or a final 12? What's the numbers of humans?
Dean Jackson:
Oh yeah, there was 12 humans that were- Weren't taken
Dan Sullivan:
Over. We're not taking over.
Dean Jackson:
In the joining. I thought what a really interesting ...
Dan Sullivan:
In my lifetime, I've discovered about five of them. You're one of them.
Dean Jackson:
Okay. Yeah. The interesting thing is it was a really interesting ... If you think about the joining the many at Pluribus as the physical embodiment of AI, the large language model, that was what was very interesting. What I found really was that one of the 12, one of the people who was unaffected by it very quickly learned on that anything is possible. And so they were Carol, the lead character, she summoned ... The many are responsible for delivering whatever Carol wants kind of thing. They're at her service. And so she arranges a meeting. She wants to meet the 12. And so they set it up for South of France or somewhere. And one of the gentlemen realized that he has access to everything. So he insisted on being flown on Air Force One, that that's available to him, that whatever is available is available to you.
And I thought it was a really interesting thing of how some people put limits on themselves, even when everything is available to you. That this guy was thinking without limits, like, "What's the thing? I want Air Force One to come and why me to meet with them." And it was really ... I thought it's the same. It's very interesting to see
Dan Sullivan:
How- So are they immortal too?
Dean Jackson:
That's a great question. I don't know that whether they're immortal, but ...
Dan Sullivan:
Yeah, because if not, then they're limited by time.
Dean Jackson:
Yeah. It's unclear to me right now whether they are immortal.
Dan Sullivan:
Well, you can only push a plat so far. It's like metaphors. Metaphors are very useful up to a point. Yeah. Yeah.
Dean Jackson:
Unless you're a self-miller.
Dan Sullivan:
I mean, is it driving them crazy or what's happening to
Dean Jackson:
Them? Well, it's very ... So Carol is set on undoing the joining because she feels that everybody has this right to be an individual with their own autonomy and agency and whatever it is, rather than just blending in and becoming the group mind. And so there's another gentleman from Ecuador or somewhere in some Spanish speaking he is, and he
Dan Sullivan:
Wants to- Not Venezuela.
Dean Jackson:
Not Venezuela. He wants to do the same thing. No, not Venezuela, luckily.
Dan Sullivan:
Yeah. Yeah. Yeah. Yeah, because Nicholas Maduro's ... Things were just normal on Saturday and on Brooklyn. And then 24 hours later, he was in a jail cell in Brooklyn. And I mean, that's quite a shift in one day.
Dean Jackson:
So tell me the ... I know all those words that you just said, but I don't know the actual ... Can you give me the synopsis of-
Dan Sullivan:
Well, it would happen when your phone was in the box.
Dean Jackson:
Yeah.
Dan Sullivan:
Yeah. Yeah. First of all.
Dean Jackson:
Overnight.
Dan Sullivan:
So Trump couldn't call you to let you know because check your back calls. Maybe Trump maybe Trump dropped a call. Yeah. In 30 minutes, they got in and got out. They went in and they found him and his wife in his bedroom and they packed him up and brought him by helicopter to a carrier in the Mediterranean ... Not Mediterranean, in the Caribbean. And then they flew him to New York and he's now in a jail cell in Brooklyn. Yeah, the two of them. Yeah. Yeah. And that's because he said he wouldn't stop sending drugs to the United States.
Dean Jackson:
Okay. Okay.
Dan Sullivan:
They brought him to the United States.
Dean Jackson:
Okay. There you go.
Dan Sullivan:
Yeah.
Dean Jackson:
And how do people in Venezuela feel about that?
Dan Sullivan:
Apparently there are celebrations all over. I mean, first of all, there's two types of people in Venezuela, those who are joyous and celebrating, and those who are confused and pissed off. And I mean, you never get complete consensus on something like this.
And so anyway, it's apparently really well planned, really well executed and really well. No American lives lost, no equipment left behind. They went in with 120 planes, knocked out all the power and Karakas, knew exactly where to go, flew in. Now, there's no report of casualties. I suspect there's some casualties because he had Cuban security pretty troops because Cuba depends upon Venzauela for its oil. And so that stopped about two weeks ago. They stopped the oil to Vince or to Cuba just by stopping the ships and now just decided that to move things forward, they just put him in a jail cell in Brooklyn and then see how the negotiations go after that.
Dean Jackson:
Wow. And now, so that will affect the South American stuff. Wasn't he the nexus for funding?
Speaker 3:
Yeah.
Dan Sullivan:
Yeah. Yeah. Yeah
In this episode of Welcome to Cloudlandia, we explore how Miles Copeland, manager of The Police, turned Sting's unmarketable song "Desert Rose" into a 28-million-dollar advertising campaign without spending a dime. The story reveals a powerful principle most businesses miss—the difference between approaching companies at the purchasing department versus the receiving dock.
Dan introduces his concept that successful entrepreneurs make two fundamental decisions: they're responsible for their own financial security, and they create value before expecting opportunity. This "receiving dock" mentality—showing up with completed value rather than asking for money upfront—changes everything about how business gets done.
We also explore how AI is accelerating adaptation to change, using tariff policies as an unexpected example of how quickly markets and entire provinces can adjust when forced to. We discuss the future of pharmaceutical TV advertising, why Canada's interprovincial trade barriers fell in 60 days, and touch on everything from the benefits of mandatory service to Gavin Newsom's 2028 positioning. Throughout, Charlotte (my AI assistant) makes guest appearances, instantly answering our curiosities.
SHOW HIGHLIGHTS
How Miles Copeland got $28M in free advertising for Sting by giving Jaguar a music video instead of asking for payment.
Why approaching the "receiving dock" with completed value beats going to the "purchasing department" with requests.
Dan's two fundamental entrepreneur decisions: take responsibility for your financial security and create value before expecting opportunity.
How AI is accelerating adaptation, from tariff responses to Canada eliminating interprovincial trade barriers in 60 days.
Why pharmaceutical advertising might disappear from television in 3-4 years and what it means for the industry.
Charlotte the AI making guest appearances as the ultimate conversation tiebreaker and Google bypass.
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:
Good morning. Good morning.
Dean Jackson:
Good morning. Good morning. Our best to you this morning. Boy, you haven't heard that in a long time, have you?
Dan Sullivan:
Yeah. What was that?
Dean Jackson:
KE double LO Double G, Kellogg's. Best to you.
Dan Sullivan:
There you go.
Dean Jackson:
Yes,
Dan Sullivan:
There you go.
Dean Jackson:
I thought you might enjoy that as
Dan Sullivan:
An admin, the advertise. I bet everybody who created that is dead.
Dean Jackson:
I think you're probably right.
Dan Sullivan:
Yeah. I was just noticing that. Jaguar, did you follow the Jaguar brand change?
Dean Jackson:
No. What happened just recently?
Dan Sullivan:
Yeah. Basically maybe 24. They decided to completely rebrand. Since the rebranding, they've sold almost no cars and they fired their marketing. That's problem. Problem. Yeah. You can look it up on YouTube. There's about 25 P mode autopsies.
Dean Jackson:
Wow.
Dan Sullivan:
Where
Dean Jackson:
People are talking mean must. It's true. Because they haven't, there's nothing. It's pretty amazing, actually, when you think about it. The only thing, the evidence that you have that Jaguar even exists is when you see the Waymo taxis in Phoenix.
Dan Sullivan:
Is that Jaguar?
Dean Jackson:
They're Jaguars. Yeah.
Dan Sullivan:
I didn't know that. Yeah. Well, yeah, they just decided that they needed an upgrade. They needed to bring it into the 21st century. Couldn't have any of that traditional British, that traditional British snobby sort of thing. So yeah, when they first, they brought out this, I can't even say it was a commercial, because it wasn't clear that they were selling anything, but they had all these androgynous figures. You couldn't quite tell what their gender was. And they're dressed up in sort of electric colors, electric greens and reds, and not entirely clear what they were doing. Not entirely clear what they were trying to create, not were they selling something, didn't really know this. But not only are they, and then they brought out a new electric car, an ev. This was all for the sake of reading out their, and people said, nothing new here. Nothing new here. Not particularly interesting. Has none of the no relationship to the classic Jaguar look and everything. And as a result of that, not only are they not selling the new EV car, they're not selling any of their other models either.
Dean Jackson:
I can't even remember the last time you saw it. Betsy Vaughn, who runs our 90 minute book team, she has one of those Jaguar SUV things like the Waymo one. She is the last one I've seen in the wild. But my memory of Jaguar has always, in the nineties and the early two thousands, Jaguar was always distinct. You could always tell something was a Jaguar and you could never tell what year it was. I mean, it was always unique and you could tell it wasn't the latest model because they look kind of distinctly timeless.
And that was something that was really, and even the color palettes of them were different. I think about that green that they had. And interesting story about Jaguar, because I listened to a podcast called How I Built This, and they had one of my, I would say this is one of my top five podcasts ever that I've listened to is an interview with Miles Copeland, who was the manager of the police, the band. And in the seventies when the police were just getting started, miles, who was the brother of Stuart Copeland, the drummer for the police. He was their manager, and he was new to managing. He was new to the business. He only got in it because his brother was in the band, and they needed a manager. So he took over. But he was very, very smart about the things that he did. He mentioned that he realized on reflection that the number one job of a manager is to make sure that people know your band exists. And then he thought, well, that's true. But there are people, it's more important that the 400 event bookers in the UK know that my band exists. And he started a magazine that only was distributed to the 400 Bookers. It looked like a regular magazine, but he only distributed it to 400 people.
And it was like the big, that awareness for them. But I'll tell you that story, just to tell you that in the early two thousands when Sting was a solo artist, and he had launched a new album, and the first song on the album was a song called Desert Rose, which started out with a Arabic. It was collaboration with an Arabic singer. So the song starts out with this Arabic voice singing Arabic, an Arabic cry sort of thing. And this was right in the fall of 2001. And
Speaker 1:
Yeah, that's a good,
Dean Jackson:
They could not get any airplay on radio airplay. You couldn't get American airplay of a song that starts out with an Arabic wailing Arabic language. And so they shot a video for this song with Chebe was the guy, the Che Mumbai, I guess is the singer. So they shot a video and they were just driving through the desert between Palm Springs and Las Vegas, and they used the brand new Jaguar that had just been released, and it was really like a stunning car. It was a beautiful car that was, I think, peak Jaguar. And when Miles saw the video, he said, that's a beautiful car. And they saw the whole video. He thought you guys just made a car commercial. And he went to Jaguar and said, Hey, we just shot this video, and it's a beautiful, highlights your car, and if you want to use it in advertising, I'll give you the video.
If you can make the ad look like it's an ad for Sting's new album. I can't get airplay on it now. So Jaguar looked at it. He went to the ad agency that was running Jaguar, and they loved it, loved the idea, and they came back to Miles and said, we'd love it. Here's what we edited. Here's what we did. And it looks like a music video. But kids, when was basically kids dream of being rock stars, and what do rock stars dream of? And they dream of Jaguars, right? And it was this, all the while playing this song, which looked like a music video with the thing in the corner saying from the new album, A Brand New Day by Sting. And so it looked like a music video for Sting, and they showed him an ad schedule that they were going to purchase 28 million of advertising with this. They were going to back it with a 28 million ad spend. And so he got 28 million of advertising for Stings album for free by giving them the video. And I thought, man, that is so, it was brilliant. Lucky, lucky. It was a VCR. Yeah. Lucky,
Dan Sullivan:
Lucky, lucky.
Dean Jackson:
It was a VCR collaboration. Perfectly executed.
Dan Sullivan:
Yeah. Yeah. It just shows that looking backwards capability, what I can say something that was just lucky looks like capability.
Dean Jackson:
Yeah, the whole,
Dan Sullivan:
I mean, basically it saved their ass.
Dean Jackson:
It saved Sting and Yeah. Oh yeah. But I think when you look in the,
Dan Sullivan:
No, it was just lucky. It was just lucky. I mean, if there hadn't been nine 11, there's no saying. There's no saying it would've gone anywhere.
Dean Jackson:
Right, exactly.
Dan Sullivan:
Well, the album would've gone, I mean, stain was famous.
Speaker 1:
It would've
Dan Sullivan:
Gone, but they probably, no, it's just a really, really good example of being really quick on your feet when something,
Dean Jackson:
I think, because there's other examples of things that he did that would lead me to believe it was more strategic than luck. He went to the record label, and the record label said, he said he was going to give the video to Jaguar, and they said, you're supposed to get money for licensing these things. And then he showed them the ad table that the media buy that they were willing to put behind it. And he said, oh, well, if you can match, you give me 28 million of promotion for the album, I'll go back and get some money fr
AI becomes a thinking partner, not a replacement, as Dan Sullivan and Dean Jackson compare their distinct approaches to working with artificial intelligence.
In this episode of Welcome to Cloudlandia, we explore how Dan uses Perplexity to compress his book chapter creation from 150 minutes to 45 minutes while maintaining his unique voice. Dean shares his personalized relationship with Charlotte, his AI assistant, demonstrating how she helps craft emails and acts as a curiosity multiplier for instant research. We discover that while AI tools are widely available, only 1-2% of the global population actively uses them for creative and profitable work.
The conversation shifts to examining how most human interactions follow predictable patterns, like large language models themselves. We discuss the massive energy requirements for AI expansion, with 40% of AI capacity needed just to generate power for future growth. Nuclear energy emerges as the only viable solution, with one gram of uranium containing the energy of 27 tons of coal.
Dan's observation about people making claims without caring if you're interested provides a refreshing perspective on conversation dynamics. Rather than viewing AI as taking over, we see it becoming as essential and invisible as electricity - a layer that enhances rather than replaces human creativity.
SHOW HIGHLIGHTS
Dan reduces his book chapter creation time from 150 to 45 minutes using AI while maintaining complete creative control
Only 1-2% of the global population actively uses AI for creative and profitable work despite widespread availability
Nuclear power emerges as the only viable energy solution for AI expansion, with one gram of uranium equaling 27 tons of coal
Most human conversations follow predictable large language model patterns, making AI conversations surprisingly refreshing
Dean's personalized AI assistant Charlotte acts as a curiosity multiplier but has no independent interests when not in use
40% of future AI capacity will be required just to generate the energy needed for continued AI expansion
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Speaker 1:
Welcome to Cloud Landia,
Speaker 2:
Mr. Sullivan?
Speaker 1:
Yes, Mr. Jackson.
Speaker 2:
Welcome to Cloud Landia.
Speaker 1:
Yes. Yeah. I find it's a workable place. Cloud Landia.
Speaker 2:
Very, yep. Very friendly. It's easy to navigate.
Speaker 1:
Yeah. Where would you say you're, you're inland now. You're not on
Speaker 2:
The beach. I'm on the mainland at the Four Seasons of Valhalla.
Speaker 1:
Yes. It's hot. I am adopting the sport that you were at one time really interested in. Yeah. But it's my approach to AI that I hit the ball over the net and the ball comes back over the net, and then I hit the ball back over the net. And it's very interesting to be in this thing where you get a return back over, it's in a different form, and then you put your creativity back on. But I find that it's really making me into a better thinker.
Speaker 3:
Yeah.
Speaker 1:
Yeah. I've noticed in, what is it now? I started in February of 24. 24, and it's really making me more thoughtful. Ai.
Speaker 2:
Well, it's interesting to have, I find you're absolutely right that the ability to rally back and forth with someone who knows everything is very directionally advantageous. I heard someone talking this week about most of our conversations with the other humans, with other people are basically what he called large language model conversations. They're all essentially the same thing that you are saying to somebody. They're all guessing the next appropriate word. Right. Oh, hey, how are you? I'm doing great. How was your weekend? Fantastic. We went up to the cottage. Oh, wow. How was the weather? Oh, the weather was great. They're so predictable and LLME type of conversations and interactions that humans have with each other on a surface level. And I remember you highlighted that at certain levels, people talk about, they talk about things and then they talk about people. And at a certain level, people talk about ideas, but it's very rare. And so most of society is based on communicating within a large language model that we've been trained on through popular events, through whatever media, whatever we've been trained or indoctrinated to think.
Speaker 1:
Yeah, it's the form of picking fleas off each other.
Speaker 2:
Yes, exactly. You can imagine that. That's the perfect imagery, Dan. That's the perfect imagery. Oh, man. We're just, yes.
Speaker 1:
Well, it's got us through a million years of survival. Yeah, yeah. But the big thing is that, I mean, my approach, it's a richer approach because there's so much computing power coming back over, but it's more of an organizational form. It's not just trying to find the right set of words here, but the biggest impact on me is that somebody will give me a fact about something. They read about something, they watch something, they listen to something, and they give the thought. And what I find is rather than immediately engaging with the thought, I said, I wonder what the nine thoughts are that are missing from this.
Speaker 3:
Right?
Speaker 1:
Because I've trained myself on this 10 things, my 10 things approach. It's very useful, but it just puts a pause in, and what I'm doing is I'm creating a series of comebacks. They do it, and one of them is, in my mind anyway, I don't always say this because it can be a bit insulting. I said, you haven't asked the most important question here. And the person says, well, what's the most important question? I said, you didn't ask me whether I care about what you just said. You care. Yeah. And I think it's important to establish that when you're talking to someone, that something you say to them, do they actually care? Do they actually care?
Speaker 1:
I don't mean this in that. They would dismiss it, but the question is, have I spent any time actually focused on what you just told me? And the answer is usually if you trace me, if you observed me, you had a complete surveillance video of my last year of how I spent my time. Can you find even five minutes in the last year where I actually spent any time on the subject that you just brought up? And the answer is usually no. I really have, it's not that I've rejected it, it's just that I only had time for what I was focused on over the last year, and that didn't include anything, any time spent on the thing that you're talking about. And I think about the saying on the wall at Strategic Coach, the saying, our eyes only see, and our ears only here what our brain is looking for.
Speaker 2:
That's exactly right.
Speaker 1:
Yeah. And that's true of everybody. That's just true of every single human being that their brain is focused on something and they've trained their ears and they've trained their eyes to pick up any information on this particular subject.
Speaker 2:
The more I think about this idea of that we are all basically in society living large language models, that part of the reason that we gather in affinity groups, if you say Strategic coach, we're attracting people who are entrepreneurs at the top of the game, who are growth oriented, ambitious, all of the things. And so in gatherings of those, we're all working from a very similar large language model because we've all been seeking the same kind of things. And so you get an enhanced higher likelihood that you're going to have a meaningful conversation with someone and meaningful only to you. But if we were to say, if you look at that, yeah, it's very interesting. There was, I just watched a series on Netflix, I think it was, no, it was on Apple App TV with Seth Rogan, and he was running a studio in Hollywood, took over at a large film studio, and he started
Speaker 1:
Dating. Oh yeah, they're really available these days.
Speaker 2:
He started dating this. He started dating a doctor, and so he got invited to these award events or charity type events with this girl he was dating. And so he was an odd man out in this medical where all these doctors were all talking about what's interesting to them. And he had no frame of reference. So he was like an odd duck in this. He wasn't tuned in to the LLM of these medical doc. And so I think it's really, it's very interesting, these conversations that we're having by questioning AI like this, or by questioning Charlotte or YouTube questioning perplexity or whatever, that we are having a conversation where we're not, I don't want to say this. We're not the smartest person in the conversation kind of thing, which often you can be in a conversation where you don't feel like the person is open to, or has even been exposed to a lot of the ideas and things that we talk about when we're at Strategic Coach in a workshop or whatever. But to have the conversation with Charlotte who's been exposed at a doctoral level to everything, it's very rewarding.
Speaker 1:
She's only really been exposed to what Dean is interested in.
Speaker 2:
Well, that's true, but she, no, I'm tapping into it. I don't know if that's true. If I asked her about she's contributing, her part of the conversation is driven by what I'm interested in, but even though I'm not interested in the flora and fauna of the Sub-Saharan desert, I'm quite confident that if I asked her about it, she would be fascinated and tell me everything she knows, which is everything about Sub-Saharan flora and fauna.
Speaker 1:
How would you even know that?
Speaker 2:
I could ask her right now, because
Speaker 1:
She's been exposed to ask her, here's a question for Charlotte. When she's not with you, is she out exploring things on her own? Does she have her own independent? Does she have her own independent game? And that she's thankful that you don't use up all of her time every day because sh
In this episode of Welcome to Cloudlandia, we discuss our experiences working alongside an AI assistant named Charlotte. We explore how Charlotte helps us create personalized emails, enhancing our creativity and productivity. Through funny stories and thoughtful discussions, we see how AI is changing professional and creative landscapes.
We also talk about the art of time management. The idea is to treat life like a game, where the goal is to achieve personal milestones within the time you have each day. By focusing on three main tasks and celebrating small victories, you can feel more accomplished.
The conversation shifts to self-awareness and leadership in a virtual world. We discuss the importance of breaking away from predictability and using mental frameworks to capture and apply new ideas.
The episode ends with a look at evolving creative partnerships, emphasizing the power of collaboration and being present with your audience.
SHOW HIGHLIGHTS
In this episode, Dan and I discuss the revolutionary impact of AI on creativity and productivity, highlighting how our AI assistant, Charlotte, crafts personalized emails that reflect our personalities.
We explore the concept of time management as a game, where achieving daily goals brings a sense of accomplishment and managing time effectively can alter our perception of time itself.
The conversation touches on the balance between digital engagement and real-world experiences, emphasizing the impact of excessive screen time on teenagers' mental health.
We delve into the importance of self-awareness and leadership in a virtual world, using a mental framework to navigate internal dialogues and embrace creativity.
There's a fascinating discussion on the role of virtual platforms like Zoom during the pandemic, which have reshaped brainstorming and productivity by facilitating more focused and reflective sessions.
Our guests share their experiences of evolving creative partnerships, emphasizing the shift from idea curation to output command, and the benefits of structured playfulness in enhancing creative capabilities.
Finally, I reflect on the potential of AI to deepen personal and professional growth, highlighting the anticipation of continued collaboration with Charlotte for fresh insights and experiences.
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean: Mr Sullivan.
Dan: Mr Jackson, it's always good to hear your voice.
Dean: Always wonderful, and it seems like this week went fast, faster than usual. But we all know, dan, it actually moved at the speed of reality, the speed of reality 60 minutes per hour. Speed of reality moved at the speed of reality, the speed of reality 60 minutes per hour.
Dan: Speed of reality is like the law of gravity. That is the truth.
Dean: Yeah, charlotte made me laugh out loud today.
Dan: That's a good sign.
Dean: actually, I'll tell you what I asked Charlotte this morning. I said what are the top 10 impacts you could have in my life? And she said here's a prioritized list of the top 10 impacts I can have, mapped by impact versus effort, with examples from your world. And it was so funny. She listed all these things. You know daily email companion. You know you talk, I type, I shape, title and polish. You know all of these things curate and repackage your IP, brainstorming and naming partner. You know all these high insight leverage.
Dan: Then she started I said tell me more about that. Sounds to me like Charlotte wants this to be lifetime a lifetime relationship.
Dean: I agree, and it's so funny.
Dan: She included herself in all of your impact.
Dean: Oh, yeah, and. But she referred back to all of our history. Right, I said tell me more about number one, right, my daily email companion. And she said you know you talk. I go straight. This is the highest impact, lowest friction thing we can do, because you already generate so many brilliant observations, frameworks, stories and examples just by being Dean Jackson. You live in a state of constant insight. My job is to harvest that in real time and shape it into daily emails that strengthen your relationship with your list, cement your authority as the world's most interesting marketer, create a growing archive of evergreen content, seed future books, offers, talks and more Boy.
Dan: I mean Boy talk about a plug for online dating. I mean really types of emails we can create.
Dean: an example that made me laugh out loud was, you know, personal notes, observations, story based personal notes, and the subject she had for that was I had eggs, bacon and clarity this morning Eggs, bacon and clarity.
Dan: Yeah, eggs, bacon and clarity.
Dean: Like that is legitimately funny Dan.
Dan: I mean it's so like that is legitimately funny. Then, yeah, well, she's. You know. They say that I want you to take this in the right way, but that dogs take on the personality of their owner, you know.
Dean: I mean it's so funny. Every email?
Dan: No, I think you know, I find it really, really interesting. I mean that my sense is that you're that Charlotte is a medium that enables you to get in touch with you at your best.
Dean: She said why this works so well for you. Because, one, you don't need to sit down and write. Two, you're naturally prolific. This just catches the water from your stream. Three, you already have an audience who loves hearing from you. And four, you're building a library, not just sending one-offs.
Dan: Yeah, it's very interesting. I mean I, charlotte is several levels higher than Charlotte is several levels higher than my current confidence with AI. I mean what you're doing, Because I do other things during the day. Do you know that, Dean?
Dean: I mean, I do Wait a minute, your week isn't just going around getting observations and sharing them with me on Sundays. Come on.
Dan: That's all I can do. But the thing is just from the perplexity interchange. It's really interesting what I'm learning about my ambitions and my intentions, which you're doing too, of course. But I just move on to the next capability and I think that probably you're in a real steady flow of that. But, for example, I had 45 minutes before I was coming on with you this morning. I said let's just write a chapter of a book.
Dean: And.
Dan: I do it with a fast filter and seven minutes ago it's complete. I have it with a fast filter and seven minutes ago it's complete. I have a complete. So what that means is that I have a fast filter that. I can sit down with Shannon Waller who interviews me on it then it gets, then it gets transcribed, mm-hmm, and then it goes to the writer editor team who put it into a complete chapter. But I've completed my, except for being interviewed on it, which is all this stuff and so yeah.
So I mean that would be something that, previous to perplexity, I would think about for about a week and then. I would have a deadline staring me in the face and I'd have to get it done. And I do a good job. You know, I do a good job and yeah but here it's just how much is deadline?
Dean: do you think is the catalyst?
Dan: oh, yeah, yeah.
Dean: A hundred percent.
Dan: But the deadline is Thursday for this and I would be doing it Wednesday night. Here I said I know I can knock this off before I talk to Dean. I said I know just from my experience. So you know that was like 28 minutes. I had a complete chapter where, well, if you include the not getting to it with actually getting to it, it's probably about five hours.
Dean: About a four to one ratio. Yeah, exactly, no, no.
Dan: But I used to do this with the in the early days. I had a lot of life insurance agents.
Like you have a lot of real estate, real estate agents, and I said, those big cases, those big cases, some of the big cases you have, and the problem with the life insurance industry is that you put in an enormous amount of work before you even know if there's a possibility of a payoff. So they said, well, those big cases, I had one once. It took me two years. The person said it took me two years and I said, boy, it took a long time. I said actually no, I said the actual result was instantaneous.
Dean: It was not getting the result.
Dan: that took two years, and I think that this really relates to what AI does. We've put time estimates on things where it all depended upon us. And we say well, that'll take me five hours to get to that result. And this morning. It took me 28 minutes to do it and I was, you know, and it just flowed there. There was no problem. It was in my style and had my voice. You know the way I write things, so it's really, really interesting. Our time estimation is what's changing.
Dean: I agree, because the base reality of time is constant. You know what I've been likening.
Dan: You're either in the river, you're either in the water or you're not in the water.
Dean: That's exactly right. You're exactly right.
Dan: Should I jump? What's it going to feel like when I get there, exactly?
Dean: Have you seen? There's a video game called Guitar Hero and it's on, you know, xbox or any of these other ones, and they have a guitar and instead of strings it has buttons yellow, blue, green, red and you are on a. You're standing at the base of what it looks like a guitar bridge with the strings there, and when you start the game, the music starts moving towards you, like you are in a Tetris game or something right it's coming towards you.
Dan: When you said that, I just thought of Tetris.
Dean: Okay, yeah, exactly so it's coming towards you like Tetris, and then it's showing you what you need to press, right at the moment. When it hits the line, the horizon, right where it meets you, you have to be, you press. You know red and then green and then blue, and you have. The game is that you are concentrating and you'r
In this episode of Welcome to Cloudlandia, we explore the shifting landscape of expertise in the digital age. Our discussion starts by examining the sheer volume of digital content and how it challenges traditional learning and expertise. With AI playing a significant role, we consider how this technology might disrupt long-established institutions like universities, allowing individuals to gain expertise in new ways.
We then take a historical journey back to the invention of the printing press, drawing parallels between past and present innovations. Using AI tools like ChatGPT, we uncover details about Gutenberg's early legal challenges, showcasing how AI can offer new insights into historical events. This approach highlights how asking the right questions can transform previously unknown areas into fields of expertise.
Next, we discuss the changing role of creativity in an AI-driven world. AI democratizes access to information, enabling more people to create and innovate without needing institutional support. We emphasize that while AI makes information readily available, the challenge of capturing attention remains. By using AI creatively, we can enhance our understanding and potentially redefine what it means to be an expert.
Finally, we consider the impact of rapid technological advancements on daily life. With AI making expertise more accessible, we reflect on its implications for traditional expert roles. From home renovation advice to navigating tech mishaps, AI is reshaping how we approach problems and solutions. Through these discussions, we gain a fresh perspective on the evolving landscape of expertise and innovation.
SHOW HIGHLIGHTS
We discuss the overwhelming volume of digital content and how it challenges the utility and comprehension of information in the modern age.
Dean talks about the potential impact of artificial intelligence on traditional educational institutions, like Harvard, and how AI might reshape our understanding of expertise.
Dan describes the intersection of historical innovation and modern technology, using the invention of the printing press and its early legal battles as a case study.
We explore how AI democratizes access to information, enabling individuals to quickly gather and utilize knowledge, potentially reducing the role of traditional experts.
Dean shares humorous thought experiments about technological advancements, such as the fictional disruption of electric cars by the combustion engine, highlighting the societal impacts of innovation.
Dan critically examines energy policies, specifically in New York, and reflects on creative problem-solving strategies used by figures like Donald Trump and Elon Musk.
We reflect on the evolving landscape of expertise, noting how AI can enhance creativity and transform previously unexplored historical events into newfound knowledge.
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean: Mr Sullivan.
Dan: But who's going to listen to all the transcriptions? That's what I want to know. Who's going to read them yeah, but what are they going to do with them? I don't know, I think it's going to confuse them actually.
Dean: They're on to us. They're on to us. They're on to us and we're on to them.
Dan: Yeah but it's a problem. You know, after a while, when you've overheard or listened to 3 million different podcasts, what are you doing with it? I know, is it going anywhere? Is it producing any results? You know, I just don't know that's really.
Dean: It's funny that you say that right. Like there's, I and you have thousands of hours of recorded content in all of the podcasts. Like between you know, podcasting is your love language. How many five or seven podcasts going on at all time. And I've got quite a few myself.
Dan: I have eight series.
Dean: You've got eight series going on regularly 160 a year times, probably 13 years. Yeah, exactly.
Dan: Let's say but there's 1,600. Let's say there's 1,600 and it adds up.
Dean: Let's call that. We each have thousands of hours of on the record, on the record, on your permanent record in there. Yeah, because so many people have said uh you know, you think about how much people uh talk, you think about how much people talk without there being any record of it. So that body of work. I've really been trying to come to terms with this mountain of content that's being added to every day. Like it was really kind of startling and I think I mentioned it a few episodes ago that the right now, even just on YouTube, 500 hours a minute uploaded to YouTube into piling onto a mountain of over a billion available hours.
Dan: It's more than you can. It's really more than you can get to.
Dean: And that's when you put it in the context of you know, a billion. I heard somebody talk about. The difference between a million and a billion is that if you had,1 a second each second, for if you ran out, if you're spending that $1 a second, you would run out if you had a million dollars in 11 and a half days, or something like that and if you had a?
billion dollars, it would be 30 be 11 000, 32 years, and so you think about if you've got a million hours of content it would take you know it's so long to consume it.
Dan: You know it's funny. I was thinking about that because you know there's a conflict between the US government and Harvard University. I don't know if you follow this at all. No, government and Harvard University. I don't know if you follow this at all. Because no? Yeah, because they get about. You know they get I don't know the exact number, but it's in the billions of dollars every year from the US government, harvard does you know? Harvard does you?
know, and and. But they, you know they've got some political, the DEI diversity, and the US basically is saying if you're, if you have a DEI program which favors one race over another, we're not going to give. We're not going to give you any more money, we're just not going to give you any more money. I mean unless it's if you favor one racial group over another, you don't get the. You don't get US tax money. So they were saying that Harvard has $53 billion endowment.
And people say, well, they can live off their endowment, but actually, when you look more closely at it, they can't, because that endowment is gifts from individuals, but it's got a specific purpose for every. It's not a general fund, it's not like you know.
We're giving you a billion dollars and you can spend it any way you want Actually it's very highly specified so they can't actually run their annual costs by taking, you know, taking a percentage, I think their annual cost is seven or eight billion dollars to run the whole place billion to run the whole place. So if the US government were to take away all their funding in eight, years they would go bankrupt.
The college would go, the university would just go bankrupt, and my sense is that Trump is up to that. The president who took down Harvard. The president who took down Harvard. It wouldn't get you on Mount Rushmore, but there's probably as many people for it as there are against it.
Dean: Well, you never know, by the end it might be Mount Trump. We've already got the gulf of america who named it?
Dan: anyway, yeah it's so, it's, yeah, it's so funny because, um you know, this was a religious college at one time.
You know, harvard, harvard college was once you know, I I'm not sure entirely which religion it was, but it was a college. But it's really interesting, these institutions who become. You say, well, you know they're just permanent, you know there will never be. But you know, if a college like a university, which probably, if you took all the universities in the world and said which is the most famous, which is the most prominent, harvard would you know, along with Cambridge and Oxford, would probably be probably be up and you know what's going to take it down.
It is not a president of the United States, but I think AI might take down these universities. I'm thinking more and more, and it has to do with being an expert. You know, like Harvard probably has a reputation because it has over, you know, 100 years, anyway has hundreds of experts, and my sense is that anybody with an AI program that goes deep with a subject and keeps using AI starts acquiring a kind of an expertise which is kind of remarkable, kind of an expertise which is kind of remarkable.
You know, like I'm, I'm beginning that expert expertise as we've known it before november of 2022 is probably an ancient artifact, and I think that that being an expert like that is going to be known as an expert, is probably going to disappear within the next 20 years. I would say 20 years from now 2045,. The whole notion of expert is going to disappear.
Dean: What do you? Think I mean you think, I think yeah, I have been thinking about this a lot.
Dan: You'll always be the expert. You'll always be the expert of the nine-word email. That's true, forever, I mean on the. Mount Rushmore of great marketing breakthroughs. Your visage will be featured prominently. That's great. I've cemented my place in this prominently.
Dean: That's great. I've cemented my place. Yeah, that's right. Part of that is, I think, dan, that what I am concerned about.
Dan: That would be the highest mountain in Florida, that's right, oh, that's right. Oh, that's funny, you'd have to look at it from above.
Dean: That's right. The thing that I see, though, is exactly that that nobody is doing the work. I think that everybody is kind of now assuming and riding on the iterations of what's already been known, because that's what that's really what AI is now the large? Language.
That's exactly it's taking everything we know so far, and it's almost like the intellectual equivalent of the guy who famously sa
Today on Welcome to Cloudlandia, Our discussion unravels the surprises of Ontario's geography, the nuances of tariff wars, and the timeless drive for ambition, ensuring you're well-equipped with insights into how technology continues to redefine the global landscape.
Discover how NuCom's innovative app is revolutionizing sleep and relaxation. We dive into the specifics of how its unique audio tracks, like "Summer Night," are enhancing REM and deep sleep, all while adding a humorous twist with a comparison to Italian driving laws. With separate audio for each ear and playful suggestions for use, you'll learn how this app is setting new standards for flexibility and effectiveness in achieving tranquility.
Finally, we ponder the evolving nature of trust in a world increasingly dominated by AI and digital interactions. Drawing inspiration from thinkers like Jacques Ellul and Thomas Sowell, we discuss the societal shifts driven by technological advances and the potential need for encryption to verify digital identities.
SHOW HIGHLIGHTS
<li>We discuss the intriguing journey from Ontario's cottages to the realm of international trade, focusing on how AI is reshaping trade agreements and challenging the predictability of global politics.</li>
<li>Dean explores NuCom's innovative app designed to improve sleep and relaxation through unique audio tracks, highlighting its effectiveness in enhancing REM and deep sleep.</li>
<li>We ponder the evolving nature of trust in a digital world increasingly dominated by AI, exploring how we can maintain authentic human interactions amid rapidly advancing generative tools.</li>
<li>Dan shares a humorous story of two furniture companies' escalating marketing claims, setting the stage for a discussion on capitalism and the importance of direct referrals in business.</li>
<li>We delve into the impact of technology on society, drawing insights from Jacques Ellul and Thomas Sowell, and compare AI's transformative potential to historical technological advancements like the printing press.</li>
<li>Dean highlights the importance of personalized market strategies, exploring how personal solutions can evolve into valuable products for a wider audience.</li>
<li>We explore the concept of ambition and agency, discussing how adaptability and a forward-looking mindset can help navigate new realities and unpredictable changes in the world.</li>
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean: Mr Sullivan.
Dan: Ah, Mr Jackson. General Jackson. General Jackson. Dictator Jackson
Dean: Now there's two thoughts that are hard to contain in the brain at the same time. Are you in Toronto or at the cottage today? At the cottage, look at you, okay.
Dan: Yeah, all is well, very nice day, yeah, except our water went out and so we can't get it fixed until tomorrow morning because it's cottage country. Till tomorrow morning because it's cottage country. And you know, this is not one of those 24-7 everybody's available places on the planet.
Dean: Where do people in cottage country go to get away from the hustle and bustle of cottage country on the weekends?
Dan: Yeah, it's a good question. It's a good question. It's a good question they go about two hours north.
Dean: It feels like that's the appropriate amount of distance to make it feel like you're getting away.
Dan: In the wild.
Dean: Yeah.
Dan: So we're having to use lake water for priming the vital plumbing.
Dean: The plumbing you have to do.
Dan: You have to have pails of water to do that and we'll do. Even though it feels like a third world situation, that's actually a first world problem.
Dean: You're right, you're exactly right.
Dan: Yeah, yeah, beautiful day, though. Nice and bright, and the water is surprisingly warm because we had a cold winter and the spring was really cold and we have a very deep lake. It's about um the depth meters on the boats go down to 300 feet, so that's a pretty deep lake that's a deep lake.
Yeah, yeah, so here we are here's a factoid that blew my mind. The province of Ontario, which is huge it's 1,000 miles north to south and it's 1,200 miles east to west has 250,000 freshwater lakes, and that's half the freshwater lakes on the planet. Isn't that amazing?
Dean: Yeah, I heard a little. There's some interesting Ontario facts. I remember being awed when I found out that you could drive the entire distance from Toronto to Florida north and still be in Ontario.
Dan: Yeah.
Dean: Yeah, yeah.
Dan: Yeah, If you go from the furthest east, which is Cornwall a little town called Cornwall to the furthest west, which is a town called Kenora Right, kenora to the furthest west, which is a town called canora right, uh, canora. It's the same distance from that as from washington dc to kansas city. Oh, that's amazing yeah I had a good.
Dean: I had a friend who was from canora. He was an olympic decathlete, michael sm. He was on the Olympic decathlon team and that's where he was from Kenora, kenora.
Dan: Mm-hmm. Yeah, yeah, it's a lot of big. I mean most of it's bugs, you know most of it's bugs. It's not, you know, the 90% of the Ontario population lives within an hour 100 miles of the? U, lives within an hour a hundred miles of the US. Yeah, yeah, you know, I mean that's it's if you go from the east coast to the west coast of Canada. It's just a 3,200 mile ribbon, about a hundred miles high that's really can't. From a human standpoint, that's really Canada. Everything else is just bugs yeah.
Dean: So it's very. I guess you've been following the latest in the tariff wars. You know again Canada with the oh yeah, well, we're going to tax all your digital things, okay.
Dan: Okay, yeah, okay we're done. Yeah, we're done. That's it Good luck Stay tuned.
Dean: We'll let you know how much we're going to charge you to do business. I mean, where does this posturing end, you know? Where do you see this heading?
Dan: Well, when you say posturing, you're Well.
Dean: I don't think I mean it's.
Dan: There's a no. It's the reworking of every single trade agreement with every single country on the planet, which they can do now because they have AI. Yeah, I mean, you could never do this stuff before. That's why using past precedents of tariffs and everything else is meaningless.
Dean: Well, here's an example.
Dan: If the bombing of Iran, which happened in recent history, iran which happened in recent history, if that had happened 30 years ago, you would have had a real oil and gas crunch in the world.
Everything would crunch, but because people have instant communications and they have the ability to adjust things immediately. Now, all those things which in the past they said well, if you do that, then this is going to happen. Now I don't think anything's going to happen, Everybody's just going to adjust. First of all, they've already built in what they're going to do before it happens. You know, if this happens, then this is what we're going to do.
And everybody's interconnected, so messages go out, you know they drop the bomb, the news comes through and in that let's say hour's time for everybody involved. Probably you know 10 billion decisions have been made and agreed on and everybody's off and running again. Yes, yeah.
Dean: Yeah, it's amazing how this everything can absorb.
Dan: I think the AI changes politics. I think it changes, I think it changes everything. Mm-hmm, mm-hmm.
Dean: Agreed, yeah, but, but, but not necessarily in any predictable way, mm-hmm. Right, exactly.
Dan: Yeah.
Dean: But meanwhile we are a timeless technology.
Dan: We are.
Dean: I was rereading you Are a Timeless Technology. Yeah, these books, Dan, are so good oh thank you. Yeah, I mean, they really are, and it's just more and more impressive when you see them all you know lined up 40 of them, or 44 of them, or whatever. I'm on 43.
Dan: I'm on 43. 43 of them yeah, I'm on 43. I'm on 43. 43 of them, yeah, yeah, yeah, yeah. This one's called Always More Ambitious, and we talked about this in the recent In the free zone yeah. In the free zone that I'm seeing ambition as just the capability platform for all other capabilities.
Dean: Yes, you know, you have ambition and you know or you don't.
Dan: And then agency goes along with that concept that, depending on your ambition, you have the ability to adjust very, very quickly to new things. For example, getting here and, uh, it was very interesting. We got here yesterday and, um, we had an early dinner. We had an early steak dinner because we were going to a party and we didn't think that they would have the kind of steak at the party that we were right, they didn't have any steak at all.
Oh, boy, and they had everything that I'm eating steak. The reason I'm eating steak is not to eat the stuff that's at the party. Right, exactly, yes, I mean, I'm just following in the paths of the mentor here, of the mentor here, anyway, anyway, um, so you know, all the water was working and everything, and when we went to the party we came home and the water didn't work and it's some electrical connection you know, that in the related to the pump and um and anyway, and I just adjusted.
you know, it was still light out, so I got a bucket and I went down to the lake and I got a bucket full of water and I brought it up and you know, and I was really pleased with OK. Ok, scene change.
Dean: Yeah right, Exactly yeah. Scene change.
Dan: Ok, you, you gotta adjust to the new one, and I'm new reality, right yeah, new reality.
Okay, what you thought was going to happen isn't going to happen. Something is going to happen and that's agency. That's really what agency is in the world. It's your ability to switch channels that there's a new situation and you have the ability not to say, oh, I'm, oh, why, jane? You know, and you k
In this episode of Welcome to Cloudlandia, I reconnect with Dan Sullivan for another wide-ranging conversation that blends current events, history, technology, and human behavior.
We start by reflecting on the safety and comfort of life in Canada while discussing the news of missile strikes in Israel. From there, we explore the idea that innovation often advances when entrenched leaders move on—whether in science, business, or geopolitics. Dan brings up Thomas Kuhn’s idea that progress happens after the old guard exits, creating room for new ways of thinking.
Our conversation shifts into the role of AI as a horizontal layer over everything—similar to electricity. We compare this shift to earlier transitions like the printing press and the rise of coffee culture. Dan shares his belief that while AI will transform systems, the core of human life will still revolve around handled needs and personal desires.
We wrap by talking about convenience as the ultimate driver of progress. From automated cooking to frictionless hospitality, we recognize that people mostly want things to be “handled.” Despite how fast technology evolves, it’s clear that unless something is of deep personal interest, most people will let it pass by. As always, the conversation leaves room for reflection and humor, grounded in the reality that technological change doesn’t always mean personal change.
SHOW HIGHLIGHTS
Dan and I explore the complexities of living in a "world-class" city like Toronto, discussing its cultural vibrancy against the backdrop of global geopolitical tensions.
Dan delves into Toronto's significant role as a financial and technological hub, emphasizing its strategic importance in trade with the United States, where a substantial portion of Canadian exports cross the border.
We discuss the transformative potential of AI in today's digital revolution, drawing parallels with historical innovations like Gutenberg's printing press, and how these advancements continuously redefine our society.
We examine the evolution of Starbucks, from a unique third space with artisanal baristas to a more automated environment, and ponder the implications of this shift on quality and customer experience.
The conversation shifts to the rise of independent coffee shops, highlighting how they meet the demands of discerning customers by offering premium experiences.
Dean reflects on our relentless pursuit of convenience in modern urban life, where technological advancements shape our daily routines and enhance our quality of life.
We conclude with a discussion on habit formation and the role of technology in reinforcing existing habits, while considering the balance between maintaining old routines and embracing new ones.
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean: Mr Sullivan,
Dan: Mr Jackson, I hope the rest of your day yesterday went well.
Dean: Oh, delightful, I learned stuff yesterday. That was a very nice day, beautiful, beautiful weather today. You know what, dan, if you could, as an option at the Hazleton, upgrade to include your perfect weather for $1,000, this is what you'd order, it's this kind of day. Yeah, mid-70s perfect white fluffy clouds. Yes, it's why.
Dan: Living in a safe, globally unimportant country.
That's exactly right. Holy cow, I don't know if you've seen, yeah, what's uh? I woke up like literally just a few minutes ago seeing all the, uh, the raining missiles on israel right now from Iran. Have you seen that this morning?
Dean: Oh yeah, there's a lot of them. Most of them don't hit anything and most of them are shot down, but still it puts some excitement in your day.
Dan: I mean really, yeah, these ones look like. They're something unique about these ones that they're supersonicersonic and many of them are hitting, yeah, different than what we've normally seen. Like normally, when you see it, it's the, the iron dome or whatever is, you know, intercepting them, which is always interesting, but these ones are like Direct, like you can see them hitting in inrael that's. I mean, could you imagine, dan, like you, just look at how geographically we are. You know we've won the geographic lottery in where we're positioned here, you know, just realizing that's never. Even though you can, all you know you always take precautions with the umbrella above us, over the outside.
Dean: But I mean still that today. I've lived in Toronto for 54 years now, just past the anniversary, the 54th anniversary and I think that, first of all, when you have a really large city like Toronto, the center of a lot of things that go on in Canada, A world-class city like Toronto. Well, it's not a world-class city. But yeah, they have to go five years. I'm putting a new rule in for world-class cities. You have to go five years without ever saying the words.
Dan: Yeah, we're a world-class city.
Dean: We're a world-class city. And that takes you to stage one probation.
Dan: Yeah.
Dean: No, that takes you to stage two, probation, and then stage three probation is where all the people who've been saying it's a world-class city have either died or moved, and then it's sort of like science. There was a famous he wasn't a scientist, but he was a, I think, a science historian. Thomas Kuhn K-U-H-N if you ever came across that name wrote in the 1960s and he wrote a very influential book which is called the Structure of Scientific Revolutions, and he was asked many times when you have a sudden series of scientific breakthroughs and we really haven't had any for quite a long time, it's been mostly almost a century since we've had any real scientific revolutions. So all the progress we've made over the last century were for discoveries in physics and magnetism and electricity and uh, you know nuclear but they had already worked out how that was going to happen in the by the 1920s.
and he said what when, all of a sudden, when you get a breakthrough, let's say, for example, they discover a new hydrogen atom and it essentially gives everybody free energy? That would be a scientific breakthrough. Do you think that I mean? Would you think?
Dan: that would be.
Dean: Yeah, yeah. In other words, energy just didn't cost anything anymore, you know, and the price of energy would go down.
Dan: That would free up a lot of that, free up a lot of other things energy would go down that would free up a lot of that'd free up a lot of other things, and, uh, and, and he said, the single biggest cause for scientific breakthroughs is the funerals of old scientists. Oh who everybody defers to that you can't first them.
Dean: Yeah, well, defers to, but they control promotion of young scientists. They control where the money goes for a scientist and then they die and their control loosens up and to the degree that control disappears. Now you get new.
Dan: Yes.
Dean: Yeah, so that's a long way around. But I think that in the world today there are people who are basically in control of geopolitical systems, economic systems, you know, cultural systems, and in the next 10 years, I think, a lot of the controllers are going. They'll either die or people will think they've already died. They don't have to actually die, they just have to be in a room somewhere and no one's heard, and no one's heard anything from them recently, and uh and uh, you know, and everything like that, and then things change and then things really shifted. But my sense about Toronto is that it's going to be the Geneva of the Western Hemisphere.
Dan: Okay, that's interesting.
Dean: Switzerland from a geopolitical standpoint really. I mean, nobody ever talks about well, what do the Swiss think about this? But lots of stuff happens in Geneva. People meet in Geneva. There's tons of money that goes through Geneva and you know, when you know people who hate each other want to talk to each other and feel safe about it, they do it in Geneva that's interesting.
Dan: How did Switzerland become its neutrality known for? Is that just because of its positioning between Austria?
Dean: and Germany mountains.
Yeah, the uh, the germans had given some thought during the second world war to invade switzerland, and switzerland can put into the field in a very short period of time a very big army. I don't know what the numbers are. But the other thing is, uh, for the longest period I know maybe a century long they've been howling out the mountains. So they've got, you know, they've got secret bases inside the mountains, but there's also they've created lots of dams with big reservoirs and if there was ever an invasion they would just blow up the dams and they would flood the entire lowlands of.
You know, people are told to the mountains, the entire lowlands of you know, people are told to the mountains, get to your bunker. You know everybody's got a bunker and they've all got guns and they do it. You know they just want to. They're in the middle of one of the most warfare inclined continents in human history. Europe is very warlike. It's always been warlike.
Dan: Europe is very warlike. It's always been warlike, but they haven't wanted to be part of the wars, so they've taken the other approach.
Dean: Yeah, and Canada is kind of like that, but the US is very uniquely positioned, because a lot of people don't know this. I mean, you come to Toronto and it's big skyscrapers, yeah, you know, and it's a financial center. It's very clearly a big financial center, it's a big communication center, it's a big tech center. But a lot of people don't know it's a big manufacturing center. There's the airport here.
Dan: Oh yeah, All around the airport.
Dean: Mile after mile of low-rise manufacturing Industrial yeah, all around the airport Mile after mile of low-rise manufacturing Industrial. Yeah Actually, sasha Kurzmer, who yo
In this episode of Welcome to Cloudlandia, Dan and I talk about how much AI is reshaping everyday life. I share how new tools like Google’s Flow V3 are making it easier than ever to create video content, while Dan explores how AI could tackle complexity—like managing city traffic or enhancing productivity—when it's applied intentionally.
We also look at how people are adapting to the massive increase in content creation. I ran some numbers: Americans spend around 450 minutes per day on screens, but YouTube alone sees 500 hours of content uploaded every minute. So while AI makes it easier to create, attention remains limited—and we’re all competing for it.
Another theme is “agency.” We discuss how autonomous vehicles, digital payments, and convenience tools reduce friction, but can also make people feel like they’re giving up control. Dan points out that even if the technology works, not everyone wants to let go of driving, or of how they interact with money.
Lastly, we reflect on what it really means for tools to be “democratized.” I talk about Hailey Bieber’s billion-dollar skincare brand and the importance of vision, capability, and reach. The tools might be available to everyone, but outcomes still depend on how you use them. We end with thoughts on tangibility and meaning in a world that’s becoming more digital by the day.
SHOW HIGHLIGHTS
In this episode, we delve into Canada's evolving identity, sparked by significant events such as the King's visit and U.S. tariffs, which have prompted provinces to reevaluate internal trade barriers.
Dan explores the challenges and comparisons between Canada and the U.S., particularly in areas like cannabis legalization and its broader implications on issues such as prison reform.
We discuss the health concerns surrounding the rise of vaping, particularly its impact on youth, and how it is becoming a focal point in societal discussions.
We navigate the transformative role of energy innovation and artificial intelligence, examining their impact on industries and economic power, particularly in the context of U.S. energy consumption.
Dean shares personal experiences to illustrate AI's capabilities in reshaping information consumption, emphasizing technology as a powerful change agent.
The intersection of technology and consumer behavior is dissected, with a focus on convenience trends, including the selective demand for electric vehicles and limousine services in luxurious locales.
We conclude with a humorous anecdote about students using tape-recorded lectures, reflecting on the broader implications of convenience and technology in education.
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean: Mr Sullivan.
Dan: How are things in Florida Hot?
Dean: Hot, it's hot.
Dan: It's hot.
Dean: They're heated up.
Dan: It's normal.
Dean: Yeah, no, this is like it's unusual. It went from perfect to summer, All just overnight. I'm looking forward to coming to. I'm looking forward to coming to Toronto, to coming to. I'm looking forward to coming to Toronto Two weeks right, Two weeks here.
Dan: Friday. I'm actually uh, You're going to spend a week.
Dean: Yeah, I'm in.
Dan: Chicago. I'm in Chicago next week.
Dean: Yeah, I'm in. So I'm. Yeah, I'm coming for three weeks.
Dan: You're holding court. You're holding court.
Dean: I'm holding court every which way I arrive on Friday, the 6th, and I leave on the 29th, so there. So you are going to be in Chicago next Saturday.
Dan: Next Saturday you're in Chicago, yeah, until the Friday and then back home and we'll have our. Whether it's table 9 or not, it's going to be table 9. Let's just call it table 1, because it'll be at restaurant one.
Dean: That's exactly right.
Dan: It'll probably be nice to maybe even sit outside, which is a very good restaurant. Yes, on the patio. Yeah, yeah, that's great. Well, canada is going through profound changes.
Dean: That's what I hear, so prepare me. I'm already prepared that I will be ordering Canadians with breakfast instead of Americanos.
Dan: They've already conditioned me for that. I've been here 54 years in Toronto 54 years and over 54 years I've never gotten a good answer about what a Canadian is.
Dean: Okay.
Dan: Okay, except that we're not Americans. We're not Americans. And to prove it, and to prove it, they brought the King of England over to tell them Okay, ah that's funny.
Dean: I didn't see anything about that. Is that just that yeah?
Dan: we came over. They have a thing called the throne speech. When parliament resumes after an election, it's called the throne speech.
Dean: Okay, just a reminder.
Dan: Yeah, and so just to tell you that we're an independent, completely independent country, we got the King of England to come over and talk to his subjects.
Dean: And.
Dan: I guess that's what caused the division in the first place, wasn't it?
Dean: was the King of.
Dan: England. So nothing's changed in 236 years. It's all been. You know the royalty. They brought the royalty over to put some muscle into the Canadian identity, anyway. But there is a profound change and I don't know if you knew this, but there's tremendous trade barriers between the provinces in Canada.
Dean: Yeah, it's funny how Canada has really always sort of been more divisive kind of thing, with the West and the Maritimes and Quebec and Ontario.
Dan: But they have trade barriers. Like they're separate countries, they have trade barriers and Trump's pressure putting tariff on has caused all the provinces to start talking to each other. Maybe we ought to get rid of all the trade barriers between the provinces it's just that pressure from the south that is causing them to do that, and they would never do this voluntarily. Yeah, but it's putting such pressure on the canadian economy, in the economy of the individual provinces, that they're now having to sit down and actually maybe we shouldn't have barriers between you know and the.
US has never had this. You know the US straight from the beginning was a trade free country. You know the states don't have trade barriers.
Dean: Right right.
Dan: I mean they have laws that have not been entirely in sync with each other, for example, alcohol, you know, Some of the states were dry, and so it wasn't that we won't allow you to compete with our alcohol. We don't have any alcohol and we won't allow you to bring your alcohol in Fireworks. You couldn't have fireworks. Some states you could have Citizens could buy fireworks. I remember Ohio. You could never buy fireworks but you had to go to Michigan to buy them.
Dean: Is cannabis now nationally legal in Canada?
Dan: What's that fireworks?
Dean: No cannabis.
Dan: Fireworks, no, just the opposite. Cannabis, yeah, exactly. Yeah, yeah, it's national, and that's another thing. The US, generally, when there's a contentious subject, they don't. Well, they did do it. They did it with Roe versus Wade, and then, of course, roe versus Wade got reversed. The way that American tradition is one state does it, then another state does it, and that gets to a point where it's like 50% of the states are doing, and then it elevates itself to a national level where the Congress and the Supreme Court they start, you know.
Dean: Florida. Florida just rejected it again. Every time it's on the ballot it gets rejected in Florida.
Dan: What's that?
Dean: Cannabis. Oh yeah, it's a state issue. Yeah.
Dan: Yeah, and I don't think it's ever going to be national, because there's enough bad news about cannabis that probably they won't go for it. I mean the impact.
Dean: Well, think about all the people that they would have to release from prison that are in prison right now for cannabis violations. You know it's interesting. That's one of the things that has been the discussion here.
Dan: You know is you can't legalize it, and then all of a sudden yeah. They'd have to get a whole new workforce for the license plates Right.
Dean: Well, the robot.
Dan: Yeah, robots.
Dean: Well, the robots, the robots.
Dan: The robots can smoke the cannabis, yeah, yeah, but it's. I don't see it ever being national in the US, because there's as much argument there is for it, there's as much argument that there is against it. And you know, especially with young people, especially with you know it's a gateway drug. They know that if someone in their teens starts smoking cannabis, they'll go on to higher-grade drugs.
Dean: That's interesting.
Dan: That's pretty well established Actually smoking is the first. Tobacco, first then cannabis. The big issue down here now is vaping.
Dean: Vaping.
Dan: I've never quite understood. What is it exactly? I see that we have some stories here yeah, what is vaping?
Dean: what is vaping? It's just like a chemical you know way of getting nicotine, you know and it's pure chemicals that people are sucking into their lungs. It's crazy no smoke no smoke. It's because in most cases you know you can vape in places that would be otherwise smoke free. This is just vapor, you know, so it's not intrusive, you know?
Dan: what's funny is, I haven't tell you how up to tells you how up to date I am right I'm getting my news about vaping from dean jackson. Yeah, that tells you how up to date I am right. Oh yeah, I'm getting my news about vaping from.
Dean: Dean Jackson. Yeah, exactly.
Dan: That tells you how out of touch I am.
Dean: That's right, I stay in touch with what the kids are doing. Dan, I'll tell you. I keep you up to date.
Dan: That's so funny. Kids, yeah, how much less than 80 does childhood start?
Dean: I don't know I'm hanging in there. I just turned 40, 19. So let's see Keep that. We'll keep it going, keep it alive.
Dan: Yeah.
Dean: So it's been an interesting week.
Now we're coming up on like 10 da
In this episode of Welcome to Cloudlandia, we kick off by reflecting on a recent trip to the UK, where London's unexpected warmth mirrored the friendliness of its black cab drivers. Our visit coincided with the successful launch of the 10 Times program in Mayfair, which attracted participants from various countries, adding a rich diversity to the event.
Next, we delve into the advancements in AI technology, particularly those related to Google Flow. We discuss how this technology is democratizing creative tools, making it easier to create films and lifelike interactions. This sparks a conversation about the broader implications of AI, including its potential to transform industries like real estate through AI-driven personas and tools that enhance market operations.
We then shift our focus to the political arena, where we explore the Democratic Party's attempt to create their own media influencers to match figures like Joe Rogan. The discussion centers on the challenges of capturing consumer attention in a world overflowing with digital content, and the need for meaningful messaging that resonates with everyday life.
Finally, we touch on aging, longevity, and productivity. We emphasize the importance of staying engaged and productive as we age, inspired by remarkable individuals achieving significant milestones beyond 60.
SHOW HIGHLIGHTS
In our recent trip to the UK, we experienced the unexpected warmth of London and engaged with the local culture, which included charming interactions with black cab drivers. This atmosphere set the tone for a successful event launch in Mayfair with global participants.
We discussed the sparse historical records left by past civilizations, such as the Vikings, and how this impacts our understanding of history, drawing a parallel to the rich experiences of our recent travels.
AI advancements, particularly Google Flow, are revolutionizing the creative landscape by democratizing filmmaking tools, allowing for lifelike scenes and interactions to be created easily and affordably.
The potential of AI in the real estate market was explored, using the example of Lily Madden, an AI-driven persona in Portugal, which highlights the challenge of consumer attention in an ever-saturated digital content environment.
We analyzed the Democratic Party's approach to media influencers in the 2024 election, noting the need for genuine engagement with voters' lives amidst fierce competition for attention in today's media landscape.
The discussion shifted to aging and longevity, focusing on productivity and engagement in later years. We emphasized the importance of remaining active and contributing meaningfully past the age of 60.
We wrapped up the episode with excitement about future projects, including a new workshop and book, highlighting our commitment to staying creatively engaged and inviting listeners to join us in future discussions.
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean: Mr sullivan it has to be recorded because it's uh historic thinking it's historic thinking in a historic time things cannot be historic if they're not recorded, that is true, it's like if, uh, yeah, if a tree falls in the forest yeah, it's a real.
Dan: It's a real problem with what happened here in the Americas, because the people who were here over thousands of years didn't have recordings.
Dean: They didn't write it down. They didn't write it down.
Dan: No recordings, I mean they chipped things.
Dean: They didn't write it down.
Dan: They didn't write it down no recordings, no recordings. Yeah, I mean, they chip things into rock, but it's, you know, it's not a great process really.
Dean: I think that's funny, you know, because that's always been the joke that Christopher Columbus, you know, discovered America in 1492. But meanwhile they've been here. There have been people, the sneaky Vikings, and stuff. How do you explain that in the Spaniards?
Dan: Yep.
Dean: Yeah.
Dan: Yeah Well, writing. You know, writing was an important thing.
Dean: Yeah, yeah.
Dan: We don't know much. We don't, yeah, we really don't know much about the Vikings either, because they didn't they weren't all that great at taking notes. I mean, all the Vikings put together don't equal your journals.
Dean: That's true. All the Viking lore's the not what's happening. So it's been a few weeks yeah I was in the uk, we were in the uk for a couple weekends for uh-huh okay, it was great, wonderful weather, I mean we had the very unusual.
Dan: It was great, wonderful weather.
Dean: I mean we had the very unusual weather for May. It was, you know, unseasonably warm 75, 80, nice bright oh my goodness.
Dan: Yeah, really terrific. And boy is the city packed. London is just packed.
Dean: And getting packed dirt, huh.
Dan: Yeah, yeah, just so many people on the street.
Dean: I always, I always laugh, because one time I was there in June which is typically when I go, and it was. It was very funny because I'd gotten a black cab and just making conversation with the driver and he said so how long are you here? And I said I'm here for a week. He said, oh, for the whole summer, because it was beautifully warm here for the whole summer. Yeah, that's so funny, I hear hear it's not quite.
Dan: They're fun to talk to.
Dean: Oh man for sure.
Dan: Yeah, they know so much.
Dean: Yes, I hear Toronto. Not quite that warm yet, but get in there I think today is predicted to be the crossover day we had just a miserable week.
Dan: It was nonstop rain for five days. Oh my goodness, Not huge downpour, but just continual, you know, just continual raining.
Dean: But it speeded up the greening process because I used to have the impression that there was a day in late May, maybe today like the 25th, when between last evening and this morning, the city workers would put all the leaves on the trees like yesterday there were no leaves, and but actually there were.
Dan: We're very green right now because of all the rain.
Dean: Oh, that's great yeah. Two weeks I'll be there in. I arrived 17th.
Dan: Yeah, yeah, I'm trying to think of the date I'm actually arriving.
Dean: I'm arriving on the 6th A strategic coach, you're going to be here, yeah we're doing on Tuesday. This month is Strategic Coach.
Dan: Yeah, because of fathers.
Dean: Right, right, right right, so we're doing. Yeah, so that Tuesday, that's exciting.
Dan: Tuesday, Wednesday, Of course, our week is 19th, 18th, I think it's the 17th 17th is the workshop day and we have a garden party the night before and the day I know we have two parties.
Dean: Yeah, I love I can't go wrong yeah and hopefully we'll have our table 10 on the. Uh well, we'll do it at the one, we'll do it at the one, that's great. You've been introduced to the lobster spoons. I hear.
Dan: It's been good, that's a great little spot. I didn't overdo it, but I did have my two. I had two lobster spoons Okay, they're perfect.
Dean: I took one of my teams there about uh, six weeks ago, and we, everybody got two we got two lobster spoons and it was good, yeah, but the food was great service with service was great.
Dan: Yeah, yeah, yeah all right.
Dean: Well then, we got something I'm excited about. That's great. So any, uh, anything notable from your trip across the pond no, uh, we um jump things up um.
Dan: Last October we introduced the 10 times program in London so uh 25 to 30. I think we have 25 to 30 now and uh, so when I was there um last two weeks, it'll be, um, um two weeks or last week no, it was last week. Um, I'm just trying to get my, I'm just trying to get my bearings straight here. When did I get home? I think I got home just this past Tuesday.
Dean: This past Tuesday.
Dan: So it would have been the previous Thursday. I had a morning session and afternoon session, and in the morning it was just for 10 times and in the afternoon it was just for 10 times and in the afternoon it was for everybody. So we had about 30 in the morning and we had about 120 in the afternoon.
Dean: Oh, very nice yeah.
Dan: And you know a lot of different places. We had Finland, estonia, romania, dubai, South Africa quite a mix. Quite a mix of people from. You know all sorts of places and you know great getting together great. You know couple of tools. You know fairly new tools A couple of tools, you know fairly new tools and you know good food good hotel, it's the Barclay, which is in.
Mayfair. Okay, and it's a nice hotel, very nice hotel. This is the third year in a row that we've been there and you know we sort of stretched their capacity.
Dean: 120 is about the upper limit and what they've been to the the new four seasons at uh, trinity square, at tower bridge. It's beautiful, really, really nice, like one of my favorites no, because the building is iconic. I mean Just because the building is iconic. I mean that's one of the great things about the.
Dan: Four Seasons.
Dean: Yeah, and about London in specific, but I mean that. Four Seasons at.
Dan: Trinity it's beautiful, stunning, love it. Yeah, we had an enjoyable play going week um we did four, four, four musicals, actually four, four different. Uh, musicals we were there one not good at all probably one of the worst musicals I've seen um and uh, but the other three really terrific. And boy, the talent in that city is great. You know just sheer talent.
Dean: What's the latest on your Personality? Yeah, personality.
Dan: Yeah, the problem is that London's a hot spot right now and there's a queue for people who want to have plays there. Oh okay, Actually they have more theaters than Broadway does Is that right On the West End yeah, west End, but they're all lined up. Problem is it's not a problem, it's just a reality is that you have some plays that go for a decade. You know,
In this episode of Welcome to Cloudlandia, we start with Dan’s recent experience with stem cell injections, a journey filled with both challenges and relief. This discussion transitions into the inspiring story of a Vietnamese massage therapist who built her career in Canada, highlighting the diverse paths in the healing professions.
Our conversation then shifts to the political landscape of Canada. We analyze the unique dynamics of minority governments and consider the influence of international figures like Trump on Canadian politics. We also discuss the role of central banking figures in political negotiations and reflect on the contrasts between Canadian and American electoral perspectives.
Next, we explore the parallels between political and economic systems, examining the shift from traditional hierarchies to modern digital frameworks. The conversation covers the challenges faced by third-party candidates in the U.S., with a focus on Robert F. Kennedy's independent run, and delves into the economic tensions between China and the U.S., considering their impact on global trade relations.
Finally, we reflect on the importance of creative consistency and the power of legacy. Whether it's maintaining a long-term streak of publishing or creating innovative tools, we emphasize the value of continuously producing impactful content.
SHOW HIGHLIGHTS
We explore the intricacies of stem cell treatments and discuss my personal experience with multiple injections, sharing insights on the healing journey alongside Mr. Jackson.
The conversation transitions to Canadian politics, where we delve into the complexities of a minority government and the influence of international figures like Trump on Canadian political dynamics.
We examine the parallels between political and economic systems, focusing on the evolution from hierarchical structures to digital frameworks, and discuss the challenges faced by third-party candidates in the U.S. electoral system.
The geopolitical dynamics between China and the United States are analyzed, highlighting the differing geographical and demographic challenges and the economic tensions resulting from tariffs and trade negotiations.
We reflect on the value of maintaining a long-term creative streak, discussing the importance of consistent output and deadlines in driving productivity and ensuring a legacy of impactful content.
The discussion touches on the strategic importance of filling the future with new and exciting projects to ensure personal growth and innovation, contrasting past achievements with future aspirations.
We explore the significance of creativity in producing meaningful content across various platforms, from books and workshops to podcasts, emphasizing the role of personal reputation and motivation in maintaining a steady output.
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean: Mr Sullivan,
Dan:Mr Jackson,
Dean: there he is. How are things in your outpost of the?
Dan: mainland. Well good, I had a convalescence week. They really packed me full of new stem cells. And the procedure is things aren't good if I'm not feeling bad.
Dean: That's what I'm saying. It's along the lines of we're not happy until you're not happy.
Dan: How's that for a closing argument?
Dean: That's good, that's good.
Dan: Yeah.
Dean: Things aren't good if you're not feeling bad.
Dan: I got the procedure on the Thursday of last week, not the week we're just finishing, but the week. So Thursday, friday, saturday and it was almost one week later, exactly on Thursday, almost the same time of day, and all of a sudden the pain went away.
Dean: Okay, how long was it Acute onset? Did you have to travel in pain?
Dan: Yeah, well, I did, but they drugged me out. Yeah, they had sedatives Right when they were doing the procedure and then you had takeaways.
Dean: Yeah, A goody bag.
Dan: Nothing like a good drug. Yeah, exactly, especially a pa pain killing drug and and they're real big on this but went full force this time I had eight different injections, both ankles, both knees, even the knee. That's good they do it to reinforce what's already there. Reinforce what's already there. And then tendons the tendons in the calf, tendons in the hamstring, tendons in the quadriceps and then on both hips, both hips, so the left leg is the.
You know in the spotlight here and when you're it's like you're experiencing inflammation in the ankle, in the calf, in the knee, in the upper leg and then the hip at the same time the leg doesn't want to, the leg doesn't want to work, right exactly yeah yeah, so that's the big problem, but actually I'm feeling pretty chipper today that's great, so that.
Dean: So it took a week to get that. Is that usual or was this an unusual? Because I don't think I've ever heard you mention the pain.
Dan: Usually it was a couple of days, but they got me while they had me.
Dean: Well, that's good, and today you feel noticeably better.
Dan: Now, yeah, I was noticing that we have a long-term massage therapist who comes to our house.
Dean: Oh, my goodness.
Dan: She's been coming for 33 years. Vietnamese Wow A boat person, actually, someone who escaped on a boat when she was a teenager, actually someone who escaped on boat when she was a teenager. And you know, really, she grew up, her grandmother was. They didn't have things like registered massage therapists, everybody just did massage, you know grandmothers especially, and so she learned from her grandmother.
You know, even before she was 10 years old and so she's you, she's 60 now, 60 now. So she's been at this for about 50 years and she's availed herself of almost every kind of therapy training that there is. I mean, it was she was working till she was 45, from teenagers to 45 you know, paid for it before she ever got registered, she ever got.
oh, oh my goodness, yeah, and I asked her about that. And the licensing is only really needed if the patient is claiming insurance money yeah. So they won't give me a patient any? Well, I never asked for it, I mean. I find I'm trying to get through my entire lifetime by having as little direct contact with government as possible.
Dean: That's the best. I love that. Yes, that's great.
Dan: I know they exist and as far as garbage being picked up, streets being repaired, police stopping crime. I have no complaints about paying for that, but I know I have to have some involvement but I don't try to expand it.
Dean: That's so funny. What's the tone in Canada? Now here we are, you know, a week after the big debacle.
Dan: Well, I don't know the debacle. They basically first of all didn't really decide anything because they had a minority government before for Americans. Americans only have winners and losers, but in Canada you can have someone who's half and half.
Dean: They're half winners and half loser.
Dan: Yeah, they're like. You know. It's that less than half the country voted for the winner. That's right. But the winner got more votes than the second place because there's more than one party. You know, americans don't believe in anything. That's not a winner or a loss. You know. That's one thing. I've learned since I've been in Canada. Americans, there's only two possibilities You're a winner or you're a loser. There's no halfway. There's no participation prize for showing up and being engaged, I think, the prime minister.
He's an economist and we have a thing that it would be like the head of the Federal Reserve. In the United States you have a central bank which is called the Federal Reserve, and in Canada it's called the Bank of Canada, and then in the UK they have the Bank of England, and this man was both governor of the Bank of Canada and the governor of the Bank of England. He's a lifetime bureaucrat. He's never been anything except a bureaucrat and his first job is to negotiate with Trump.
Right exactly, and nothing in his background has prepared him for this experience.
Dean: Yeah, that's so. It is true, isn't it? I mean the whole, I think it feels like from this view.
Dan: They kicked a can both the US and Canada.
Dean: And the you know. The very interesting thing is that this vote definitely feels like a not Trump type of sentiment. You know more than it did yes.
Dan: There's no question in my I mean there's no question in anyone's mind that Trump was the issue.
Dean: Yeah, yeah, Pierre Polyev's probably going. I was so close. If that election had happened any time between November and January, it would have been a whole different story, you know.
Dan: Yeah, yeah, yeah, that was. I think. Yeah, I don't know. Yeah, I think it was that the you know. Yeah, yeah, yeah, that was. I think. Yeah, I don't know. Yeah, I think it was that the you know Trump actually putting his gaze on Canada, really, didn't happen until after, you know, after he was inaugurated after he became president, I think you're totally correct. It was from November 5th to January 20th, yeah that would have been Kaliev's window. Yeah, but yeah well, you know there's a little history to this.
A lot of people don't know it, but Canada was a major country you know in world affairs pretty well for most of the 20th century, pretty well for most of the 20th century, and part of the reason is that they were the big backup to the British Empire, like in the First World War and the Second World War. The major supplier of manpower and armaments and everything else came from Canada that backed up the British. I mean, the British were really in the eye of the storm for both of the wars, but their number one ally right from the start of the two wars was Canada. Canada was the big player. As a matter of fact, in 1945, the end of the Second World War, Canada had the third largest navy in the world and they had
In this episode of Welcome to Cloudlandia, I chat with Dan about his recent journey to Buenos Aires for stem cell therapy on his knee. After living with an injury since 1975, he shares how advancements in medical technology are providing new solutions for pain and mobility. We discuss the challenges of recovery and the impressive potential of these therapies, along with vivid stories from his experience in this vibrant city.
We also touch on the role of AI in our modern landscape, questioning its reliability and pondering whether it enhances creativity or simply recycles existing ideas.
As we explore the implications of AI, we consider how it can assist in achieving desired outcomes without requiring individuals to develop new skills themselves. Sullivan emphasizes the importance of meaningful work and the balance between utilizing technology and fostering genuine human creativity.
Our conversation wraps up by highlighting the ongoing journey of personal growth and the need for continuous improvement in an ever-evolving world.
SHOW HIGHLIGHTS
Dan shares his personal journey to Buenos Aires for stem cell therapy to rejuvenate his knee cartilage, highlighting advancements in medical technology and the promising future of these treatments.
We explore the historical significance of technological revolutions, from steam power to the creation of the alphabet and Arabic numbers, and their impact on communication and societal progress.
The discussion delves into the rapid advancements in AI technology, questioning its role in creativity and entrepreneurship, and examining its potential for convenience and efficiency.
Dan and I consider the distinction between ability and capability, reflecting on how current technological advancements like AI have amplified capabilities while individual aspirations may lag.
We discuss the integration of AI in creative processes, highlighting how it can enhance productivity and creativity without diminishing human input.
The conversation touches on the importance of efficiency and prioritization in personal growth, exploring strategies for optimizing tasks and delegating effectively.
We conclude by reflecting on the ongoing nature of personal and technological growth, emphasizing the value of continuous improvement and collaboration in achieving success.
Links: WelcomeToCloudlandia.com StrategicCoach.com DeanJackson.com ListingAgentLifestyle.com
TRANSCRIPT
(AI transcript provided as supporting material and may contain errors)
Dean: Mr. Sullivan.
Dan: Mr Jackson, it's been a while, it's been a while.
Dean: And yet here we are. Like no time has passed.
Dan: Yes.
Dean: Because it's now.
Dan: But I've put on a lot of bear miles since I saw you last.
Dean: Yeah, tell me about your journeys.
Dan: Yeah well, buenos Aires. Yep Just got back yesterday and am in considerable pain. Oh really what happened. Well, they give you new stem cells. So now, they're going after. They're going still on the knee, but now they're going after tendons and ligaments, yeah, and so this may seem contrarian, but if you're in pain, it means that they're working.
Dean: Oh, okay.
Dan: How's that? For a compelling offer If you feel really bad about this, it means that what I'm offering you is a great solution.
Dean: Yeah, with a name like Smuckers, it's got to be good, right yeah? What was that cough syrup that was known to taste so bad? Buckley's, buckley's.
Dan:
Tastes so bad. Tastes awful Works great.
Dean: Yeah, that's right. That's the perfect thing. Tastes awful, works great. So were they completely pleased with your progress.
Dan: it's, yeah, I think that the from what I can tell from they. They show you pictures of other complete cartridges. You know, okay, with other people and my left this is my left knee an injury from 1975. 1975, uh-huh, so 50 years, and it progressively wore down.
It was a meniscus tear and in those days they would remove the torn part of the meniscus, which they don't do anymore. They have new surgical glue and they just glue it back together again. But this is the. This is one of the cost of living in over a period of history where things get better and so, as a result, I have a cartilage today which is equal and capability as it was before I tore it in 1975.
However, all the adjustments my left leg and my head to make, 50-year period of adjusting to a deteriorating capability in my left there was a lot of calcification and stresses and strains on the tendons. So now that they can see the complete cartilage back, they can know exactly what they have to do with the otherons. So now that they can see the complete cartilage back, they can know exactly what they have to do with the other things. So they still reinforce it. So I get new stem cells for the cartilage because it has to be reinforced and so it's a good thing. I'm planning to live another 75 years because I think every quarter over that period I'm going to be going to Argentina.
Dean: Oh boy, this is great.
Dan: Or Argentina, is coming to me. They're going through their FDA phases right now and he's getting the doctor scientist who created this is getting his permanent resident card in the United States. So I think probably five years five years it'll be available to others. You know they don't have to make the trip.
Dean: Well, that's great so now you've got the knee cartilage of a preteen Swedish boy. We were bouncing around the mountains.
Dan: Yeah, something like that, yeah, something like that, something like that it's interesting that it wasn't 1975 when the $6 million man started out.
Dean: That's what you're going to end up as the $6 million man. We can rebuild. We'll see.
Dan: Yeah, but I had. While we were there, we had a longtime client from Phoenix was down. He was working on knees and rotator cuffs in his shoulders.
Dean: And.
Dan: I was able to say does it hurt? And he says yes, it does, and I said that means it's working.
Dean: That means it's working.
Dan: Yeah, and I said. He said you didn't tell me about the pain part before you encouraged me to come down here and I said, well, why? You know? Why, pull around with a clear message.
Dean: And I said well, why, you know why fool around with a clear message, Right, I remember when Dave Astry had he had, like you know, a hundred thousand dollars worth of all of it done, all the joints, all the like full body stuff, and he was just in such pain afterwards for a little while. But how long does the pain last?
Dan:
Imagine it's like getting well, if I go by the previous trips, which were not equal in intensity to this one, there was about three or four days. Three or four days and then you know, you're, you're up and around. Yeah, as a result of this, I'm not going to be able to make my Arizona trip, because this week for genius Right, because? I'm going to have to be in wheelchairs and everything. And if there's one place in the world you don't want to be not able to walk around, it's Phoenix.
Because, it's all walking. That's the truth. Yeah, up and down. So we're calling that off for now, and yeah, so anyway, and anyway. But they're really thriving down there. They're building a new clinic in a different part of the city, which is a huge city. I never realized how big Buenos Aires is. It's along the same size as London, you know London.
Dean: England. Yeah right, you know how big London is. How long are you go on each trip? How long are you there?
Dan: We arrive on a Sunday morning and we leave on a Friday night. Okay, so the whole week. Yeah, yeah, it's about eight days, eight travel days, because on Saturday we have to go to Atlanta to catch the next plane.
Dean: Yeah.
Dan: That's either a dog or a monkey. Which do you have there?
Dean: That was a dog, my neighbor's. I'm sitting out in my courtyard. That was my neighbor's dog. It's an absolutely beautiful Florida morning today, I mean it is room temperature with a slight breeze. It's just so peaceful out here in my courtyard aside from working out Well.
Dan: you're close to the Fountain of Youth. That's exactly right. How many? 100 miles? 100 miles to the north, st Augustine, that's right. That's exactly right.
Dean: Yeah, this whole. Just look at.
Dan: The De Leon. That's right yeah.
Dean: This whole just look at the day.
Leon, yeah, I know my I think we're going to look back at this time. You know like what? You are on the leading edge of big advantage of these treatments. You know the things that are available medically, medical science wise to us, and you realize how.
I was having a conversation with Charlotte this morning about the I want to layer in you know the benchmarks technologically around the things that we've been talking about in terms of text and pictures and audio and video and seeing them as capabilities where it all started. You know, and it's amazing that really all of it, aside from the printing press with gutenberg, is really less than 150 years old, all of it, because she asked about the benchmarks along the way and if you went from Gutenberg to different evolutions of the press, to the typewriter, to the word processors in personal computing and digital, you know PDFs and all of that stuff and distribution has really only started. You know full scale in 150 years, along with the phonograph in the mid-1800s, the, you know, photography and moving pictures all kind of happened in that one 1850 to 1900 period. You know, but the big change of course, yeah, 1900 to 1950.
Dan: Well, you know it's interesting because it's built like the question of what are the tallest mountains on the planet, and the answer is not Mount Everest. The tallest mountains on the planet are the Hawaiian Islands.
Dean: Oh, okay.
Dan: You know, the big one, the big island, I think the top peak there, Mauna Loa. I think Mauna Loa is a name of it and it's about 30,. Everest is 20, 29,000 and change, but Mauna Loa is























