Welcome to Cloudlandia Ep167: Timing, AI, and Betting on Yourself
Mar 11, 2026
01:03:22
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
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 of sense that that happened to my generation. We just got caught and it was good. And to this day, I feel that to this day, I was born into an abundant world and took advantage.
Dean:
Yeah. That's interesting, right? Because you would have been born at the tail end of the great expansion in the 20s, all that. So that's why you're saying more than enough, everybody probably ... The 20s would have probably felt like the
Dan:
80s ago. Well, I was born in 44 though. I was born.
Dean:
No, no, I get that. But I mean, the remnants of all the stuff that was created was still there because there were less ...
Dan:
Yeah. I don't pay attention to competition essentially because I didn't have any.
Dean:
Right.
Dan:
The Boomers were the competitive, the real competitive, because there was not enough for everybody, and they're fiercely, fiercely competitive.
And it's interesting. I mean, I think the talking about generations, the whole notion that there's an 18 year period, and that makes you something ... I think it's kind of hard to prove. It's one of those concepts. It's kind of hard to prove. In other words, if you were born right the first year of what they call a generation or you're born, you probably don't have that much in common with someone ... I was born in 44. I really didn't have that much in common with somebody who was, say, born in 1930. But we named things, so ...
Dean:
Yeah, exactly.
Dan:
It's
Dean:
So ...
Dan:
Yeah.
Dean:
It
Dan:
Is funny. The end of the second World War was a really big deal, and there's no question when the men came back from the service, and then there were a lot more babies.
Dean:
Imagine that.
Dan:
Yeah, imagine
Dean:
That. Imagine that. Yeah. I do take with great interest though, the demographics, like those things. You mentioned all of Silicon Valley, those people were the real founders of ... I read ... Malcolm Gladwell had a great book called Outliers.
Dan:
Did you
Dean:
Ever read that? Yeah.
Dan:
No, I didn't. I've read almost all of them, but I didn't read that one.
Dean:
Okay. So Outliers is a really fascinating thing, and it talks a little bit about what you were saying. Like you look at Steve Jobs and Bill Joy and Bill Gates, and all those guys are all the same age, right? They all arrived at just the right time in that they were ... And they had the unfair advantage of access. So Bill Gates, for instance, had unusual access to mainframe to a computer because the private school that he went to in Seattle was one of the very few schools that actually had a direct connection to a mainframe. So he had access to computing to get in his 10,000 hours of response to it. But these guys were at an age where they were ... If they were even five years or so younger, they would have gone into ... They would have been too entrenched into the mainframe world by that point to be able to be on the cusp of the personal computing
Dan:
World.
Dean:
And he talks about a lot of these things that we look at as outlier talents were really largely a factor of circumstances. Like
Dan:
He
Dean:
Starts the book with the idea that if you are aspiring to be an NHL hockey player, the
Dan:
Best- Be born in the first three months of the year.
Dean:
That's exactly right. If you're born in January, you are- January,
Dan:
February, March. If you look almost ... Because they're bigger nine months later.
Dean:
That's right. By the time ... Yeah, by the end of the year ... Yeah, they're almost a year bigger than the other ... I mean, the difference in a year when you're six or seven or 10, that's a big difference
Dan:
And
Dean:
That's when they start sorting by age group, the talent of kids. And then it becomes a self-fulfilling prophecy because they have access to better coaching and more hours of training. So by the time everything balances out when they're 15 or 16, and the difference between a 15 and a 16 year old is not that much physically, their head and shoulders are both because they had access to all the training.
Dan:
And
Dean:
I think we're going to see this in AI. We are in the cusp of this
Dan:
Right
Dean:
Now where the kids that are just coming into college age and may completely bypass college, but go into AI, that's going to be ... It's a whole different world right now. If you're starting adulthood, economic adulthood, the opportunities are like never
Dan:
Before. Yeah. It's really interesting. I read a article, I think what I'm going to tell you relates to what you just said is see if I'm skillful enough to do it.
But they were talking about why the sudden interest in the 20s generation, basically the 20s generation in socialism. And the thesis is that because the connection between university education and high paid employment has been broken over the last 15 years, I'd say over the last 15 years, but it had a lot of momentum. And so the universities can say, doesn't matter how much money you borrow, doesn't matter what matters, you're automatically going to go into an employment track after your four years. And it actually started to fall apart in the 08, 09, they're looking more and more at the subprime loan crisis in the United States, because we're talking about American examples here, not other countries. And it started to happen that first of all, there weren't as many jobs. There were more students, but there weren't as many jobs. And then the other thing was that the nature of college education really changed.
It became much more political. It became much more cultural and not so much on hard skills. So, I'm sure that the STEM, science, technology, engineering and mathematics and that, it didn't affect them, but a lot of the others became very soft subjects. And so you were given credit for being in four years university, but not once during the four years did you actually take something that was useful in the marketplace, but it really has ... I think COVID was the real hammer that came down on that. And AI, immediately, how are people adapting AI? They're going high and low with ... If you're a company, I'm talking about corporation or big company, you're seeing what the entry level people do and you're just saying, "We're going to use AI for all the entry level." And that would be summer work too. It would be like where people can do summer work or they can do evening work or they can do weekend work.
They say, "No, we're just going to use AI." But the other thing that's going very high that actually your white collar, first of all, we're talking about white collar. We're not talking about blue collar, we're talking about white claw color, and it's mostly meetings. It's mostly meetings and AI is really good at all the stuff for the scheduling, the agenda. So the top and bottom of the employment market is being taken away, seems to be right now. Yeah.
Yeah. And the other thing is that every 20 year old can make up its own mind. I mean, and some people notice, like college education, I can just see, you know, I talked to others in their 20s and they don't seem to be ... They're getting a degree, but the degree isn't worth much. Right.
Dean:
Well, I mean, you look at ... If you started, even if you look at where we are with AI, if you go back to November of 2023 when ChatGPT first came-
Dan:
22.
Dean:
Was it 22? Yeah.
Dan:
23 and I think so. Yeah.
Dean:
So we're three and a half years in, and it's a completely different ... I mean, every single
Dan:
Quarter- You may be right, and I'm wrong. I think it was 23. Yeah,
Dean:
Okay.
Dan:
November 30th, 23. Yeah.
Dean:
Yeah. So two and a half years, you're about halfway through getting a degree, and it's already a completely different world than it was in 2023. And you look at ... And just the constant layering on top of it that the AIs are getting better at creating and coding even better AIs, that self-improvement thing. So in four years, if you extend it now, another to November 2027, let's say, at the four year mark, imagine if you had started university in September of 23, whatever you're coming out with four years later, it's going to be a completely different world. I just saw somebody had a friend who went through a drive-through and all the orders are now being taken and done with AI. And I've seen the videos, I haven't seen it in person, of other kiosks, like the front counter where you're ordering as you're talking to a screen, where you're talking with somebody from the Philippines who you're seeing a real person taking your order and doing your things, but they are in the Philippines and you're at the counter.
So you see where the-
Dan:
Yeah. Well, here's the thing, the Marxism thing that I want to talk about is that you can really see it with the election of Mom Donnie, the mayor of New York,
That his real supporters were all college students and college graduates that they weren't ... He says the poor ... It wasn't the poor people at all. It was the highly educated, actually kind of privileged, privileged people, but their opportunity, their employment opportunity has been taken away and it's an insult to the status that they think they have that look, you know, I really bore down to do all the tests in grade school and high school and the ACTs and everything to get into the right university that if I got a diploma from that unit, that gave me high status in society and that status means nothing now in the world. And this is a profoundly unfair world and I feel oppressed,
Dean:
I
Dan:
Feel oppressed. And when people who think they're better than the marketplace does and feel enormously insulted or feel enormously cheated, Marxism, like Marxism and socialism is an attractive political agenda.
Dean:
And it goes back to even their parents think about what their parents went through to get them in the right preschool, so they had a good chance to get into the right elementary
Dan:
School. Yeah. And the thing is, they're very conformist. These are not innovative kids.
And by the same token, the kids that we don't hear about are the ones who they put their finger up and they tested the win and said, "Forget what everybody else is doing. I'm going to take a separate..." So what you have, and it hasn't surfaced yet, but you have an amazingly innovative group in the same generation who haven't complained or anything. They just went about mastering AI and creating an entirely new path to the future with AI, but it won't show up right away. That won't show up right away. They're not the shouters, they're not the complainers, they're busily getting market share.
Dean:
Yeah. Yeah.
Dan:
They're listening to I love marketing.
Dean:
That's exactly right. That's the place to be.
Dan:
They're looking for their profit multipliers.
Dean:
Yeah, exactly. And I think that's the great thing is that the psychology of understanding human behavior, that's really what it is, is it's behavior engineering of-
Dan:
Well, yeah, it's behavior engineering, but each individual, I mean, the ones who win are the people who engineer their own behavior. I mean, your little checklist for yourself, "I know I'll be happy when." I
Dean:
Know I'm being
Dan:
Successful,
Dean:
Yeah.
Dan:
Is behavior engineering. I mean, you did that yourself. It's kind of funny, I'm just putting together tools for the next quarter of-
Dean:
Workshop.
Dan:
Free zone. The one I'm working right now is intentional times accidental, and you have two columns, and you have the achievements that you have that were intentional. In other words, you did some thinking, and you analyzed a way ahead, and you did it, and it was successful. And the other one is an opportunity just visited you and happened to you, and everything, but it's both. Entrepreneurial success is not one or the other. It's actually both multiplying each other, but you can't be so intentional that you screen out the accidental.
Dean:
Yeah. I've been thinking a lot about your certainty and uncertainty, and that's really ... Because I've been thinking about it in the context of looking back, and you don't need much of a runway, go And backwards to completely change a trajectory. Even if you had a year or less even, sometimes just seeing where things- I think three years
Dan:
Is the
Dean:
Maximum.
Dan:
I think three years is the maximum. We're sitting at the beginning of 26. If you go back to the beginning of 23, that's enough history to figure out almost anything that you need to do over the next three
Dean:
Years.That's an interesting take. So say more about that because that's ... I know we did a- Well, first of all, there's a tool, right? We did a tool about that, three years.
Dan:
Yeah. Well, your six year framework. So three years back, three years forward. It's part of the book, always more ambitious.
Dean:
Right.
Dan:
And my set is that I think it's capability that creates the ambition. And I said, "So if you go back over the last three years and very consciously look at the gains that you've made, the gains and go a little bit deeper." Some of them were intentional and some of them were accidental. Accidental in the sense that it just showed up for you. You met someone. I mean, number one for me is just meeting Babs in my whole life, just meeting her. And it was because I was late. There was a business conference, the room was filled except for one seat and I sat down and Babs was sitting next to me. I wasn't even sure I was going to go to this weekend event and I did ride late, just one seat left. I sat down and the rest is history.
Dean:
What
Dan:
Are you looking
Dean:
At?
Dan:
Yeah. What are you looking at? You. And so that was a big and.
Dean:
Exactly.
Dan:
Yeah. Yeah. But I think it's important for entrepreneurs to give equal importance to both. There's things that you intend and the things that ... Yeah, they just happen and you take advantage of them.
Dean:
Yeah. And there's
Dan:
So very few. Yeah. But going back to your ... If I can identify one thing that I think entrepreneurs are really weak at their past, they tend to want to get away from their past. In other words, they're always creating a bigger future because they're kind of unhappy with their ... They're kind of unhappy with their past. But all the gold is in the past.
Dean:
Yeah. Yeah. Yeah. I'm always amazed. We talk about these inflection points, right? Whenever we do the exercises of going back at your 10 times inflections. And when I look back over my adult life, there's only a very few really pivotal inflection vector changers that made a difference. Like you talking about meeting Babs, if I just look at ... I think it begins with Lars Echtall, the guy that was the inspiration for me switching from tennis to business as getting in that direction.
Dan:
How old were you when
Dean:
You did that? So I was 21 and we had just was playing these were called satellite tournaments for tennis, like minor league baseball equivalent kind of thing. And had just come from this tournament in Florida that Andrea Agassi won. It was his first pro tournament. This would have been in like March of 87. And he was this 15 year old blue haired kid with this rocket, forehands, and he just was head and shoulders above people. And I was looking in the satellite events, there were ... I was 21 at the time, and there were guys that were late 20s, early 30s that were still out playing the satellite circuit. I realized that's not ... If I push the accelerator pedal, I don't want to be that. And I realized that I was a little bit late as a 21 year old to be ... Because I was playing at a very high level, but I had been at the tennis academy where the 16 year old kids and stuff, like the phenoms, the top talents in the country were all at my level or better.
And it was just an interesting thing because Lars had been a professional tennis player. He got to 180 in the world and had a knee injury. He was 26. And he had time off to recover. And in a moment of reflection, was thinking to himself, "I got this knee injury. I'm 26 years old. There's theoretically only 179 people in the world that are better than me at what I do. And I maybe have ... I've got a limited runway for this. I'm
Getting older." And his thought was, "I wonder what the 180th ranked businessman in the world is making right now." And he immediately switched games. And my thought was how I interpreted that was that if I switched to business, like at 21, I could be Andre Agassi in business, that I would be young, I would have a head start because all my cohorts were still two years away from graduating college, my peer group. And if I went back and started in business, I would have a head start and that's exact because I could take all my things that I had developed as a tennis player, competitiveness, that dinner, that conversation ... There he is. Oh.
Dan:
Your last word was competitiveness.
Dean:
Oh, competitiveness. Yeah. So I would have my ... At 21, I had all the advantages of that, of competitiveness and energy and strategy, all of that stuff. I felt like I had a really good thing and personality. I had a lot of stuff going for me. And Lars was in the real estate business and that's what ... So he had everything that I wanted. He had the Porsche 911. He had the great house. He had the great life. And so I thought that's real estate. What I really liked about real estate too was that it was a meritocracy. It was a meritocracy. It was real. Yeah, yeah, exactly. But it was more importantly, there was nobody stopping ... You could be as good as you could be, and you were personally rewarded for doing stuff. So that was ... I look at that vector change as an amazing thing.
But I think if we look back from the future, looking back to now, I think we're going to see the AI. I mean, it's a civilizational ... I don't know that there's ever been anything as big as this, as a shift in
Dan:
... Yeah. I mean, printing was very definitely one of these that if you could read, you could read and write. I mean, it pretty well sorted out the literate from the illiterate really quickly, but it actually ... Within 30 years after Gutenberg, there were 30,000 printing presses all across Europe, Northern Europe.
Dean:
How many
Dan:
Years? 30,000. In 30 years, there were 30,000 printing presses. And I mean, smaller population, bigger distances, I mean, you have to take that into account, but it had a profound impact. And it just created havoc in society over the next 150 years. I mean, it would just turn things on their head. But I mean, AI is coming as a result of all the breakthroughs that happened before it. I mean, there's probably a thousand different technologies that have each been developed. Each of them was important that goes into AI. Yeah.
Dean:
Yeah. I just think, boy,
Dan:
Is- If you hadn't had the experience of the internet for the last 20 years, AI would just be something happening in somebody's lab. It wouldn't have the social impact. Yeah.
Dean:
I think it's going to be an accelerated impact though. I think that you're saying 30 years basically is when the consumer internet basically started, right? 96 when AOL started blanketing, trying to get everybody online. It just feels, Dan, that 30 years from now, we're not even going to recognize what ...
Dan:
What does that become? Well, I mean, it's interesting. I was having a conversation and people said ... I said, "It's all a surprise." I said, "If we were having a discussion on the 10th of September and 10th of September in 2001, you'd have all sorts of plans that was going to happen and everything else." And the next day changed everything, nine eleven changed everything and same thing. History is the record of everything that people weren't expecting.
Dean:
That's exactly right. Yeah.
Dan:
They don't record the stuff that they were expecting. They only record the stuff they weren't expecting, but we keep saying, "Well, it's very clear where history's going. " It's never clear where history's going, because history doesn't go anywhere. History follows behind.
Dean:
It's just the record. It's creating a better past. That's right.
Dan:
The
Dean:
History is what actually happened.
Dan:
Yeah. Yeah. People who think that they can predict the future. I mean, you know right off the bat that it's a sales pitch. They're selling something and you want to get in early on this because the window's going to close and you're not going to have a chance to do that. I would say this, but I think that making AI useful for yourself is the same as learning arithmetic and learning, reading and writing in the first grade when you get in, when I got into first grade. These are very, very important. This is a very important skill to get on board with as soon as you can.
Dean:
Yeah. I really like durable context. I think thinking about your thinking is going to be as valuable, like our brains aren't going to change. We're taking our brains with us and thinking about your thinking is going to be an amazingly adaptive skillset and that's what all these tools that we do in Strategic Coach and Free Zone are about. And I think that I'm really looking at the VCR formula as a durable context that it's not going to ... Envision, capability and reach are the durable contexts that are going to carry on, but the things that will fit underneath those and are access to, especially to capabilities is ...
Dan:
Yeah. Yeah. Yeah. And we had a really terrific ... I don't know if you've talked to anybody, but we had a really terrific free zone summit last Tuesday and I did it all with one tool. I did the whole day with one tool and it was just guessing, betting, and payoffs. Oh man, I love
Dean:
That. Yeah.
Dan:
Yeah. And it's a tool that we've taken in one of the quarters. I think it was last year, about this time last year. So everybody was there. We had 150 if you include both. No, there was about 30 that weren't there, about 300 free centers that weren't there. We had about 80. We're at about 110 right now,
And they brought guests. So there was about 70 guests, and so I just started off and I said, "Look, we're going to do a little thinking exercise here." And I brainstormed, "What are the best guesses and bets that produced a payoff that you had?" And everybody brainstormed for a couple minutes. I said, "Okay, so let's take five of them." And I had my example and they looked at it and everything and we got that all finished in about five minutes. They got it all filled in and then they went into breakout groups and then they came back and I said, "Okay, that gets you started for the day. Now we're going to have six people and you have their sheets." So I had John Bowen, I had Chad Jenkins, I had Mike Wandler, I had Jerry Browder, I had John Kissel, and I had Ted Kerr, and they had filled in their forms previously, and then they just came up 20, 25 minutes each and I just interviewed them, biggest guests and bet that got you to where you are today, next biggest guess and bet.
And then we just talked and did three of them in the morning, did three of them in the afternoon, and then we had a panel of all six of them. Oh,
Dean:
That's great.
Dan:
Yeah. And then at the end of the day, everybody filled in the rest of their sheet, next guesses. I've never pulled off an entire day with one tool, and that was really great. But I think there's just something unusual about that tool in the sense that it gives you a language right at the end. There's guesses, guesses are just thoughts. Bets, you're taking a risk with- What are you going to do? Yeah. You're not taking a risk with a guest, you're taking a risk with the
Dean:
Better
Dan:
Because it's money, it's time, it's attention, and then there's all the other things that you're saying you're not paying attention to while you're betting, and then you get a payoff. So I think what held it together was the fact that everybody had this guest bet and pay off during the day, and I think that really pulled it off. Yeah. But it was great. Beautiful, beautiful resort. It was really nice, and the weather was great, and yeah.
Dean:
What were the two or three highlights of what people's guesses and bets? Any standouts?
Dan:
I think Mike Wandler surprised everybody because he's really into nuclear and everybody's sort of ... And he's got a head start on everybody because he can actually manufacture this stuff. He's doing the ... They're bringing back a hundred nuclear plants around the ... I mean, the whole country is, but Mike is in on the ground floor with us and they've been shut down some of them for 20, 30 years, so they need all entirely new materials and Mike can manufacture it and everything. But I think that really wowed people, that really wowed people. And I think the second thing is just how well the tool worked, how well the tool worked. And number three, I think Chad Jenkins caught everybody's attention, and I think he had a lot of people come up to him afterwards and said, "When is this conference of yours? And what's the software you've created?" And everything like that.
So I think that would be the three top ones.
Dean:
Yeah. I'm bullish on the VCR formula as a collaboration platform. I just see it guessing and betting that's the way. And I think the whole ... Yeah, and our access to capabilities is really in a way that allows us to stay in our unique abilities, that's where everybody's at there. That's the jet stream, right? It's only when people are forced outside of their unique ability that there's friction. And to
Dan:
The
Dean:
Extent you can surround yourself with other jet stream enabled unique abilities that in collaboration, that's a
Dan:
Fantastic thing. It's funny, the day before Mike, Mike Koenigs put on the 3R AI and he asked me to do a tool, so I did it. And I did up in your game where you take a look at all your activities, doing activity inventory, and there's the activities that the ones that irritate you, then there's okay activities. They don't irritate you, but they don't excite you either. They're just activity. And then third one is fascinating, but what happened, Mike talked for about an hour and a half, and he just wowed them what he can do in 20 minutes, take other people six months to do, and he can do it in 20 minutes. And so we took a break and I came back and I said, "Okay, now I'm going to give you a thinking process where you can just avoid everything that Mike is talking about.
" And you can get smart humans between you and the technology. I said, "What you want is smart humans."
Dean:
Yes,
Dan:
That
Dean:
Is
Dan:
Exactly
Dean:
Right.
Dan:
So Mike's a real smart human. You'd want Mike between you and the technology.
Dean:
Yes, exactly.
Dan:
Because
Dean:
There's no way you're going to compete with that. I mean, it's who, not how.That's the thing, right?
Dan:
Well, he's Andre Agassi. Yes,
Dean:
You're
Dan:
Exactly
Dean:
Right.
Dan:
Yeah. In one minute, I'll tell you an experience I had when I was in the army, we took care of the entertainment of half of South Korea in the eighth army. And one of our entertainers was Doreen Tracy, who was one of the original mousketeers. And so I spent three days, I was just chatting with her because we were bus riding to about five different bases. And anyway, she really impressed me because she was, at that point, she was like 20, she would have been maybe 22 years old. And she said, "This is the last time I'm ever going to be entertaining in my life. This is my last gig." And she said, "I'm only a featured entertainer because of who I was when I was 13 years old." And she said, "I'm not any better than I was when I was 13." I was way better than other 13 years old, but I'm not any better than I was when I was 13.
She said, "That can't be my career." And she said, "I have to go back and start over again." But it's like you switching from tennis to real estate. She just had this sense, she said, "There's a lot of sad stories of people trying to be in their 40s who they were when they were a child star." And she said, "I can't do that. " She went back and she became a talent manager for Warner Brothers and spent 40 years as a top talent manager in Hollywood.
Dean:
Which is such a great awareness and shift, right? Yeah.
Dan:
Very positive and pleasant person to meet. I mean, she was very, very ... I mean, she was total extrovert. She was just totally extroverted. Yep. She said, "You just got to see the writing on the wall." And she said, "I know that ... " She said, "I know I got a shift." And that was the last time I saw her. And I didn't really think of her and I didn't look at her until the internet came in and she had done her 40 years and then she created a jazz and jazz and blues club in Hollywood, but she had a lot of famous, a lot of people that she was managing Frank Zappa, she had Frank Zappa was- Oh, wow. Yeah. Yeah.
Dean:
That's crazy.
Dan:
Yeah.
Dean:
But think about at 22, that's pretty good insight on her part to have that awareness.
Dan:
Pretty self-aware tremendously. It always impressed me. I said that person tells themselves the truth, but it's kind of like she didn't have our identity tied up with ... I mean, people, you know, athletes who live off five years of their life, for the rest of their life, they live off a five year period of their
Dean:
Life.
Dan:
Yes,
Dean:
Very true.
Dan:
Yeah.
Dean:
I love it.
Dan:
Yeah.
Dean:
Yeah. So a quick update on the inevitability experiments that this putting the phone in the lockbox has become a locked in behavior now. It's like I've done it enough that it's the go- to and locked in. So now I can move on to other things, but I think moving towards ... I really see this moving towards inevitability is the ... That's the thing that can
Dan:
Ensure
Dean:
What you want to have happen happens. And even with ...
I look at ... I was up sharing with Joe Polish. I was telling him about Mr. Beast had a experiment, a video where I had a guy, they built this building that had a gym and living quarters and kitchen and a track around the outside of it and a basketball court and all the equipment and everything. And the challenge was that you move in to the building and you lose a hundred pounds or leave. And if you lose a hundred pounds, you win $250,000, right? Wow. Yeah, yeah. And so it was like he completely under ... In an environment that was a hundred percent conducive to what the goal was. And he had a personal trainer. He had all the food, like a whole grocery store basically in the thing of all of the whatever food he wanted
Dan:
To
Dean:
Cook the food. So they removed any outside distraction that added inevitability to it. And in six months, he lost the hundred pounds. And it's an interesting-
Dan:
This is Mr. Beast who did it?
Dean:
Mr. Beast set up the environment, but it was
Someone ... He did the video. It was his challenge, right? So he did that same thing. He's got a lot of his videos have a pattern where it's like a hundred days where you have to To stay in this thing for a hundred, you're artificially constraining outside influences. And that's where I think that that's inevitability. If the only food you have access to is healthy, good food, and you've got a chef there to prepare it for you and there's nothing to do but work out or play basketball or walk around the track or whatever the things, all the healthy behaviors. It's no wonder it works out.
Dan:
I mean, plus there's 250,000 too.
Dean:
Well, that's exactly right. And by the time he won, because he kept adding additional challenges on it. So in the six months he won $400,000.
Dan:
That's cool. That's really cool. Yeah. Yeah. Yeah. This is day 75 of my creating great yesterdays.
Dean:
I love it. Yeah. It's such a great-
Dan:
Best three months of my life.
Dean:
Oh, that's great. Leor will be happy to hear that.
Dan:
Yeah. No, I talked to Leor. I talked to Leo about it. Yeah. Yeah. It's really interesting because I've sort of cracked the code on ADD.
Dean:
Well, yeah. I'm excited to hear that.
Dan:
Yeah. Well, ADD is where you emotionally commit to a future possibility that doesn't exist. It would be okay if it was one of them, but it's 10 of them.
Dean:
Yeah, that's exactly right. That
Dan:
They're all modeling. They're all in competition with your present attention.
Dean:
Yes. Yes. That's the truth. And so what-
Dan:
I haven't done that for 75 days and it's really cool. It's just talk to Dean at 10:00. I got Jeff Madoff at one o'clock. I've got a couple tasks to do. I emptied the dishwasher, put all the dishes away. I had a massage this morning. I've got 10 things that are available today to have a great yesterday.
Dean:
Are you in Chicago or Toronto?
Dan:
Toronto. Toronto.
Dean:
Yeah. Oh, that's great. I
Dan:
Love that. Anyway, it's going to be 1:47. Let's
Dean:
Explore that more. I'm going to commit to ... That'd be my thing is I'm going to experiment with that to make seven days
Dan:
Of
Dean:
Creating a better past. And I'll report next week.
Dan:
All right.
Dean:
Thanks, Dan.
Dan:
Talk to you next week. Bye.
Dean:
Okay. Bye.