Welcome to Cloudlandia
Hosted by Dean Jackson and Dan Sullivan
Dean Jackson and Dan Sullivan on business, marketing, and the shift to a digital-first world.
Dean Jackson and Dan Sullivan think out loud about business, marketing, technology, and the ongoing move of the economy into "Cloudlandia", the digital-first world layered over the physical one. Long-form, unscripted conversations between two longtime collaborators.
The Outsiders Who Built Toronto
How a handful of outsiders built modern Toronto, and why every name that comes up turns out to have something in common.
Discovering Zero
Why AI feels less like a new technology and more like the moment Europe discovered zero, when traders could do in seconds what took all afternoon.
Thirty Years of Vectors
Dan's annual London trip, AI transforming industries the way automation reshaped farming, and his MELT framework: money, energy, labor, transport.
Money, Scent, and the Art of the Did List
The most enduring business lessons often come wrapped in the most unexpected stories.
Guessing, Betting, and the AI Attention Economy
The most valuable currency in an AI-saturated world isn't data or content, it's the 1,000 minutes of attention each person has available every single day.
Rules Over Insights: Time Sense and the Decider Role
The most powerful systems aren’t built on motivation; they’re built on rules that make the right action the only option.
Secrets, Surveys, and 30-Year Bets
Protecting what you've built, revisiting where you started, and betting on the systems that have never let you down.
The Inevitability System
The most productive stretch of your life probably isn’t waiting for motivation, it’s waiting for the right constraint.
Thinking What You Think, Liking What You Like
A candid reflection on how the spread of AI is making authentic human presence feel more valuable, not less.
Arguing With Time
Every conversation has the potential to reveal something useful hidden within the ordinary, and this one delivers several of those moments.
Why Relationships Still Beat Algorithms
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.
Timing, AI, and Betting on Yourself
The entrepreneurs quietly mastering AI right now won't make headlines, they'll just quietly take market share.
The Great Yesterdays
The way you structure your time shapes everything else, including who else can reach you, and when.
Creating Yesterday to Build Tomorrow
How changing fundamental time structures unlocks the kind of behavioral transformation willpower alone can never achieve.
AI, Employment, and the Future of Human Connection
Two camps at an AI marketing conference, and why focusing on the what and the who beats getting lost in the how.
The Phone-in-the-Box Experiment and the Speed of Truth
The intersection of personal transformation and rapid global change in a technology-driven world.
Why Creating Value First Changes Everything
How Miles Copeland, manager of The Police, turned Sting's unmarketable Desert Rose into a 28-million-dollar ad campaign without spending a dime.
When AI Becomes Your Thinking Partner
AI becomes a thinking partner, not a replacement, as Dan Sullivan and Dean Jackson compare their distinct approaches to working with artificial intelligence.
AI and the Future of Creative Work
How Charlotte helps write personalized emails, what AI changes about creative work, and treating time management like a game you can win.
Unlocking the Future of Learning
The sheer volume of digital content versus traditional expertise, and whether AI disrupts universities and changes how people gain it.
AI's Role in Shaping Global Dynamics
The surprises of Ontario's geography, the nuances of tariff wars, and the timeless drive for ambition in a world technology keeps redefining.
Unveiling Toronto's Dual Identity
A wide-ranging conversation with Dan Sullivan, blending current events, history, technology and human behavior.
Convenience Versus Tradition
Google's Flow V3 making video easy, whether AI can tackle real complexity like city traffic, and how people adapt to a flood of new content.
The Allure of AI in Real Estate and Beyond
A recent trip to the UK, where London's unexpected warmth mirrored the friendliness of its black cab drivers.
From Stem Cells to Geopolitical Tensions
A Vietnamese massage therapist building a career in Canada, and the unique dynamics of minority governments in Canadian politics.
Exploring the Crossroads of Health and Technology
Living with an injury since 1975, and how medical technology is offering new answers for pain and mobility, plus AI's role in all of it.
Exploring Time Zones and Trade
A unified world clock inspired by China's single time zone, how Iceland adapts to extreme daylight, and climate narratives that miss local life.
A Journey Through Technology and Personal Growth
The unpredictable nature of Toronto's weather, and its amusing impact on the city's arrival of spring.
Unexpected Skies and Local Legends
Spam Man at the Hazleton Hotel, real estate in Toronto, and how cities evolve both physically and culturally.
Unexpected Snow in the Sunshine State
A surprising Florida cold snap opens a conversation on climate variability, with Dan's temperature swings between Phoenix and Edmonton.
Cultural Ripples and Modern Innovations
Communication moving from text to video and AI's emerging role, using the progression of airliners to understand technological change.
The Tides of Media and Innovation
Written communication from Sumerian pictographs to Gutenberg, steam presses to the first email in 1971, and what each breakthrough changed.
Finding Balance in a High-Tech World
A cold and a back spasm in Canada, a limo driver discovering the heated driveway, and Canyon Ranch conversations about technology's role.
Exploring Judicial Systems and Economic Models
Thomas Sowell on US government land value, Toronto's LCBO real estate deals, and Chicago's parking meter agreement with a Saudi entity.
From Burnout to Breakthrough
How organizations can balance productivity with employee well-being, through structured breaks and strategic planning.
Unveiling the Mysteries of Modern Media
Drone sightings over New Jersey as a metaphor for a world where information and imagination intersect, plus Mr Beast, Kylie Jenner and influence.
From Childhood Snow to Cutting-Edge Networks
The growth of the coaching program, from modest beginnings in 1994 to 18 associate coaches providing 600 coaching days a year.
Endless Pursuits of Progress and Purpose
A journey from Buenos Aires to Toronto, exploring the intersections of personal health and digital technology.
Exploring Innovation and Networking
An intimate look at the Genius Network annual event in Scottsdale, with conversations featuring Bobby Kennedy, Jordan Peterson and Tucker Carlson.
Mastering Time and Embracing Happy Accidents
In our latest episode of Welcome to Cloudlandia, we take a fresh look at time management and productivity through a historical lens.
Harnessing Innovation and Collaboration
Travels through Nashville and Chicago, the growth of both cities, and a celebration at the Maxwell Clinic.
Surviving Storms and Sparking Innovation
Living in hurricane-prone areas, and the looming threat of Hurricane Milton in Florida.
Hurricanes, Health, and the Role of AI
The impact of natural disasters like hurricanes, their unpredictable effects, and the challenges of recovery in the areas they hit.
Navigating Personal Bonds and Political Views
Mingling with Joe Polish and Evan Carmichael in Toronto, and using Taylor Swift to ask whether you keep the domains of your life separate.
Transforming Tranquility into Financial Growth
Humanity's relationship with money through storytelling and belief, plus pricing, qualified leads, and attracting clients using books.
Unlocking Literary and Entrepreneurial Secrets
Insights into writing method, contrasting Stephen King's solo approach with James Patterson's collaborations.
Screen Time Evolution and Digital Dynamics
Television from Romper Room to the first color programs, limited choice then versus unlimited streaming now, and managing screen time.
Weathering Change and Creative Evolution
How weather predictions and media sensationalism shape public views, especially around storms like the impending Tropical Storm Debbie.
The Digital Economy and Its Impact on Productivity
Juniper, a voice AI that writes and codes, the attention economy where value appears without physical cost, and what Mr Beast's success shows.
CoachCon and the Art of Growing Older
The successful launch of the inaugural CoachCon, which brought 350 members of the Strategic Coach community together in Nashville.
Balancing Health and Habit
Looking back at the Cloudlandia conference at Canyon Ranch in Tucson, facilitated by the legendary Joe Polish.
Strategies for Enhanced Productivity
The Crucial ABC Questions, the 80/20 rule, and why standing still can be the strongest move you make. Strategic scheduling as liberation.
Dissecting the Fabric of Time, Commerce, and Personal Growth
Time, commerce and personal growth, and why four unavoidable costs mean a standardized global version of reality can never quite exist.
Innovative Habits for Personal Achievement
How speakers get chosen and messages get crafted, and how habits shape everything from personal growth to organizational culture and nations.
The Fusion of Innovation and the Natural World
Serenity in nature and in technology, drawing a parallel between Cloudlandia and meticulously raked sand.
Intellectual Property in the Era of Innovation and Adaptation
Whether modern life is really harder than the 1950s, what stays constant in the human condition, and how to leverage intellectual property.
Mastering Time Management
The lost art of letter writing, and how corresponding through history shaped the way these podcast conversations happen across time.
Weathering Politics and the Evolution of American Homes
How weather shapes both mood and architecture, and whether neighborhoods end up embracing nature or ignoring it entirely.
Observations on Perception
The hidden economic forces behind pivotal history, whether these are the best or worst of times, and how addictive media pulls you back in.
Creative Investing and the Search for Wellness
Dan's stem cell recovery, AI and DNA merging in diagnostics, and Indify's venture model for investing in independent artists.
Creating Conversations That Drive Business Forward
Why small workshops create a richer exchange, and the difference between self-promotion and actually understanding your clients.
The Art of Self-Management
Dean's blood and fat cells turned into new cartilage and flown across continents, and whether regenerative medicine makes 156-year lifespans real.
Revolutionizing Health, Wealth, and Tech
Dan's experience with stem cell treatments, from the different injections to increased energy and improved brain function.
The Hidden Links Between AI and Media Evolution
Converting text into a speech structure that aligns with your own heartbeat, plus where marketing education is heading next.
The Black Plague, Roman Empire, and COVID-19
The shift to Zoom and Cloudlandia set against the Black Plague and the Roman Empire, and the opportunities that emerge from unexpected times.
Discovering True Value in an Age of Convenience
An immortality gene's potential, a Buenos Aires stem cell trip, and the Working Genius model's six elements, from Wonder through to Enablement.
The Digital Revolution
The story of how Toronto transformed over the decades, thanks to the pivotal work of urban theorist Jane Jacobs.
Navigating the Labyrinth of Information: Past, Present, and Future
How radio and television first connected the world, the 1950s industries that shaped society, and how technology, energy, money and labor redefine it.
The Impact of Urbanization: Toronto's Tale and Personal Growth
Toronto's geography next to America's NFL cities, and how 20th-century developments from the GI Bill to national television still shape it.
Discovering the Power of Imagination in Shaping Our Reality
From traffic rules to sacred texts, the world we live in is entirely constructed by people like us. On imagination as the thing that shapes reality.
Ep102_Unlocking the Secrets of Success, from Cottages to Cloudlandia
Cottage renovations, the landscapes of North America, and decoding the power of vision and reach in building successful ventures.
From Enhancing Productivity to Breaking Dependencies
The power of mental images, and harnessing imagination to overcome trauma and achieve what you set out to do.
Unlocking Profit Activators for Business Success
Why making bets and guesses matters in a shifting environment, and how the eight profit activators form the foundation of any successful business.
Exploring the Power of Internal Realms and Perfection
Existing in multiple zones at once, moving beyond the binary, and discovering a third space: the Free Zone.
The Intersection of Da Vinci's Genius and the Digital Age
The intersection points of Da Vinci's genius and the current digital age, exploring the origins of technology and its impact on society.
Your Future is Guessing and Betting
Everybody says AI and big data make the future predictable, but nothing predicted Trump, Brexit or COVID. Why your future is guessing and betting.
A General Intelligence Smarter Than All Humans
How global intelligence is smarter than every human that exists, and why the idea of generic intelligence is untrue.
The wealthiest generation in the world
Building a knowledge base in ChatGPT for a network of people who can reuse it for the foreseeable future.
Thinking About Your Thinking
How durable the concept of thinking about your thinking is, why that's your best thinking, and the quality of decisions that come out of it.
The Digital Age vs Mainland Age
The collision of Cloudlandia's capabilities multiplying exponentially, while the mainland stays largely unchanged in reality.
Designing for Industry Transformation
The story of four industry transformers who are big on customer-centeredness, and why the intersection of it all is the design part of everything.
The gap between us and the next level of intelligence
How exponential improvements in AI and technology can fundamentally affect the elements of creating a uniquely successful life.
Life during techno fascism
How fascism in politics changed history, and how techno-fascism could work to boost productivity in life and creativity in entrepreneurs.
Advanced Learning for Development
The dying importance of geography, the power shifts of mainland success, and why the elements of that success matter less and less.
Everything Is All Made Up
Some rules for life and how to apply them, plus a thought that sticks: you need something you can already measure with to make a new one.
Learning about AI learning
Conversing with AI and watching it learn, including asking a Socrates character where it stands on intellectual property.
Be a Market Maker
Today we're going to talk about a simple email strategy to turn a thought into a referral-getting opportunity.
How do you price yourself in the marketplace?
This week Dean Jackson and Dan Sullivan talk about how one can price themselves in the marketplace by looking at some possible reasons why Mr.
Identifying correlations in collaborations
How different entities can collaborate by comparing their value and recognizing the relationship between what each of them is already doing.
The Power of Collaboration
A Freezone session recap and the power of collaboration, including how Kohl's partnership with Amazon brought in 2 million more customers.
Transitioning from Imagination to Reality
What it takes to create a convincing, compelling offer by filling your prospect's imagination with your vision of the outcome.
Making decisions for success - Hurricane Edition
How Cloudlandia survived the last hurricane, the types of decision-makers there are, and how to make the decisions that help you succeed.
Redefining Focus and Structure
Fresh thinking on focus and structured behavior, starting from a calendar where nothing lands on it that you didn't choose to put there.
Shortcuts Through CloudLandia
The shortcuts Cloudlandia opened up over a decade, and why a newspaper that prints its readers' objections is now the unusual one.
Overcoming Old Barriers
Overcoming old barriers with modern technology, and thinking about content as an asset you build at a budget per recorded hour.
Maintaining Your Meat Robot
How Cloudlandia and modern technology help us stay healthy and take care of our bodies, or as Dan and Dean call them, our meat robots.
Connecting The Mainland To The Cloud
How Cloudlandia makes the real world easier to navigate, and audiences falling from I Love Lucy's 80 million to American Idol's 30.
Expanding Perception Through Technology
How technology is expanding our perception and enhancing our experiences, and making life in Cloudlandia more useful day to day.
Procrastinating Your Way To Success
How Cloudlandia and VR let entrepreneurs procrastinate productively, set priorities, and still leave free space for their minds to roam.
Compelling vs Convincing
How the cloud moved selling from convincing to compelling, with a first-time homebuyer show on public access cable as the proof.
Diversifying Through the Cloud
Dean and Dan discuss the unique diversification opportunities afforded by building businesses around Cloudlandia and cloud technology as a whole.
The Cloud Meets The Real World
Where Cloudlandia meets physical technology, including the prediction that big shopping centers get retrofitted into production hubs.
Reactive vs Creative
Ditching a default reactive nature for a more rewarding creative one, and how to use Cloudlandia and the digital age to increase your creativity.
Experimenting with Digital Freedom
Experimenting in the modern age, using the freedoms granted by Cloudlandia and an ever-expanding digital revolution.
The Economic Value of Ideas
How Cloudlandia and the digital revolution gave people the ability to monetize and capitalize on their own ideas like never before.
The Centerpiece of Modern Life
The merits and the challenges of rapidly advancing technology, and the limitless possibilities Cloudlandia opens up.
Virtual Reality in The Future
The possibilities of virtual reality and landscapes like Cloudlandia, from the future of entertainment to the hardware that will make it possible.
Modern Mass Production
The dynamics of modern mass production, the effect of virtual popularity on ROI, and why a strong presence in Cloudlandia is a long-term investment.
Digital Convenience
How the convenience of the digital age opened up opportunities for everyone, and let monumental achievements get documented that would have gone unknown.
The Crossover Zone
How understanding both the digital and analogue worlds gets you the best of both, and the best use out of Cloudlandia.
Predicting The Digital Future
Using the last 30 years of technology to predict the next 30, and how digital communication in places like Cloudlandia shapes what comes next.
The World In Your Headset
The merits of virtual communication over in-person, and the advantages Cloudlandia holds over real life.
Accessing More Time
What the digital revolution did to our concept of time, and why time in Cloudlandia gets used markedly more efficiently.
The Power of Attention
How Cloudlandia reveals the power of attention: the impact of attention patterns on culture, media production and censorship trends.
The Certainty of the Cloud
How rising real-world uncertainty throws the certainty of Cloudlandia into relief, and planning a year that could still go either way.
Intellectual Shortcuts
The intellectual shortcuts Cloudlandia makes possible, and assessing your Vision, Capability and Reach with a genuinely critical eye.
Virtual Communication
The advantages of Cloudlandia interactions over in-person ones, and a hard history lesson about prosperity that has to be forced.
Utilizing Imagination
How Cloudlandia uses imagination to let you build a vision, and the moment someone else's skill tells you a choice is in front of you.
Thinking About Thinking
Dan and Dean on how Cloudlandia lets you structure your environment, giving you more room to explore yourself and adjust the way you think.
Digital Life and Analogue Thought
Practical uses for digital landscapes judged by an analogue value system, and why a company with no hardware could never have built stores.
Evolution of the Longevity Arena
How the whole longevity arena is changing, and why the people with the motivation for it generally turn out to have the means as well.
The Future Of Economics
The future of economics in Cloudlandia, tracing digital economics from the 1950s to now, and the reality one generation can't yet see.
Achieving Goals Using Attitude
How adjusting your attitude makes goals more achievable, plus a tool for seeing certainty and uncertainty across a whole network.
Increasing Focus
How the digital landscape hinges on shifting your focus, why attention became free, and why curation is about to matter.
Vision & Mindset
Developing a good vision and a free mindset, and the conversation the whole Unique Ability concept came out of.
Technology
The impact of new technology on Cloudlandia, and why you write the book for one person: you do the selecting, not the hoping.
Brands
The value of brands, and how fast a leader can fall when what people want them to talk about shifts underneath them.
Life Extension
Life extension on the Mainland, and the doctor who describes a placenta the way you'd describe crude oil: energy is one use of thousands.
The Desire for Progress
The ongoing desire for progress, and the frustration loops people got caught in when every available option felt like the wrong one.
Observing What's Happening
Observing what's actually happening as capability grows, and why remarkable skill on its own is never the multiplier people assume it is.
The Cloudlandia Advantage
Why Cloudlandia held all the advantages, and how sidestepping the how by finding the right who, or the right technology, changes the what.
Credibility Habits
Credibility habits on the Mainland and in Cloudlandia, plus the year the American frontier officially closed and why franchising followed.
The In-between Times.
The benefits of the in-between times on the Mainland, and why what's lost in a virtual meeting is qualitative, not functional.
Adopting New Capabilities
How the last year sped up the adoption of new technology, and why none of it looks likely to eliminate people any time soon.
Global Creator Class
The new Global Creator Class, and what happens when you free up 800 hours a year and fill them with thinking about your thinking.
Cloudlandia Efficiencies
The efficiencies of being in Cloudlandia, and the I Love Marketing archives holding the first mention of More Cheese Less Whiskers.
Eating Out, Staying In
Eating out while staying in, plus the hidden gems nobody visits because Ontarians all head north instead.
Going Live
Live events returning to the Mainland, with a detour into how the census rejigs 435 congressional seats and the votes that follow.
Another Year
Birthdays marking another year, and an economy where selling a digital book makes real money that never shows up in GDP or trade figures.
Springtime in Cloudlandia
Springtime in Cloudlandia, a look back at the year, and how people vote with their feet when a state stops being the one to be in.
Recommended For You
The recommendation rabbit hole, and why a page of open-ended questions lets thousands of people build a workshop from their own content.
Communication Technologies
Communication technologies, and Dan on fifty years in Toronto and the moment he felt the authorities had pushed things too far.
Developments
Developments back on the Mainland, including the sleep device Dan describes as Ambien without the drug, and seven hours on night one.
Traveling Without Moving
The benefits of traveling in Cloudlandia, plus the story of the graphic user interface and Apple's two Steves in a garage.
The Most Important Piece
The most important piece of any idea, and the question underneath it: when you hit a goal, what are you measuring it against?
Freedoms in Cloudlandia
The freedoms of living in Cloudlandia, traced back through MP3s and magnetic tape to when music stopped needing a physical object.
Packaging the Message
How the packaging of a message changes everything, and what baseball's biggest ever contract provoked in a room full of entrepreneurs.
Cloudlandia from Wherever
Freeing yourself from geographic constraints, with an Orwell detour into what happens when the past gets quietly edited.
Creating Cloudlandia Experiences
How people create experiences in Cloudlandia, including the global entrepreneur who takes a workshop at 3am rather than fly 23 hours.
Heading to the Clubhouse
The Cloudlandia Clubhouse, and seeing Strategic Coach not as a slope you climb but a circle with Who Not How at the bullseye.
Your Future is Always Normal
Why your future is always normal and it's your past that gets better or worse, plus swapping a television habit for a lifetime of novels.
Abundance
Live streaming Abundance 360, plus the hedge fund that lost three billion dollars and what the jungle does with a predator that goes too far.
VCR - Vision, Capability, Reach
Vision, Capability and Reach, and what Charles Schwab arriving in the 1980s showed about a genuine breakthrough in access.
Meeting in Cloudlandia
The efficiencies of meeting in Cloudlandia, and what food delivery replacing a phone call to each restaurant says about convenience.
Taking a Timeout
Taking a timeout in Cloudlandia, and why a conceptual product built from modular ideas travels so well in a virtual world.
Cloud Burgers
Delivering burgers from the cloud, and running across time zones where Greenwich, New York and Los Angeles cover most of the planet.
The Well of Ideas
Marketing plans pulled from the Well of Ideas, plus what a Rubik's cube and an Indiana Jones fight scene reveal about what you train for.
Building Trust in Couldlandia
Building trust and relationships in Cloudlandia, starting with one habit: before you believe an article, work out how its author gets paid.
Developing in Cloudlandia
The speed and access of personal development in Cloudlandia, and why a preference for discovering things changes what you build.
Taking Cloudlandia by Storm
Life moving fast in Cloudlandia, and how something as ordinary as a face mask reads completely differently depending where you grew up.
Boundaries in Cloudlandia
Why Cloudlandia has no boundaries built into it, and what diamond districts, auto malls and restaurant rows teach about clustering.
Who's in Cloudlandia
Finding the right people at scale, Dan's book Who Not How, and why you would map Mars with a hundred satellites before ever landing on it.
A Downpour of New Ideas
Embracing the downpour of new ideas in Cloudlandia, and the trick behind a video that only looks like it is responding to you live.
Thinking About Cloudlandia
The thinking behind Cloudlandia, and how a podcast brings people in from all over the world to one central hub.
Capability Factories
The possibilities that open up when you use other people's capability factories, and the skills quietly bypassing the establishment.
Time is Elastic
How elastic time becomes between Cloudlandia and the Mainland, when you can get exactly what you need at the moment you need it.
Connections
Making connections back to the Mainland, and intellectual shortcuts like More Cheese Less Whiskers that hold a century of marketing in a phrase.
Just in Time
How Cloudlandia makes a just-in-time lifestyle possible, and what counts as a job when millions of new ones appeared during COVID.
All-in on Cloudlandia
What being all-in on Cloudlandia reveals, including finding capability in software and AI, not only in people.
Getting to Cloudlandia
How Cloudlandia came to exist, and Dan's argument that the world's biggest problems get solved by millions of people simply creating what they want.
Checking in on the Mainland
Checking in on the Mainland, and why neither of them has done any socializing for business purposes in fifty years.
Welcome to Cloudlandia
Dean and Dan open the show: what Cloudlandia is, and how Zoom dissolved the boardrooms and workshop space a business used to need.
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