How Notion Reimagined Productivity Tools | Ivan Zhao

AI Agents and the Evolution of Work

The opening trailer reveals powerful insights about where technology is heading and why most companies are missing the mark on building truly useful AI agents.

Key Predictions:

1. Agent Revolution Coming - AI agents are still a buzzword in knowledge work, but the infrastructure is finally being built
2. Consolidation Strategy - Notion's approach of consolidating contacts and tools creates the foundation for true knowledge work agents
3. The Creative Gap Problem - There's a fundamental difference between having taste, being able to describe something, and actually being able to make it

Revolutionary Insight:

Computing is just like reading and writing. It's a medium that you can shape. But until recently, computing has been by and large the medium that only the programmer class can shape.

Ivan ZhaoNotion | Founder & CEO

Why This Matters:

• Democratization of Creation: Computing is becoming accessible beyond just programmers
• Knowledge Work Evolution: The consolidation of tools enables more sophisticated automation
• Competitive Advantage: Companies that understand this shift will build better products

Timestamp: [00:00-00:41]

The Philosophy of Simplicity in Leadership

Ivan Zhao's food preferences reveal a deeper philosophy about efficiency, authenticity, and what really matters when building world-class products.

The Burrito Philosophy:

1. Efficiency Over Elegance - Why spend 3 hours on a meal when you can get everything you need in one place?
2. Transparency in Experience - "You can just see everything" - no hidden complexities or unnecessary subtlety
3. Time as Ultimate Currency - The biggest difference isn't taste, it's time investment

Cultural Contrasts:

• Personal Evolution: From college dorm room to appreciating some formality (white tablecloth at home)
• Cultural Integration: Married to Iranian wife who introduced proper dinner rituals
• Authentic Preferences: Despite cultural influences, maintains preference for bold, simple flavors over subtle cuisine

I care, but the effort-reward ratio probably isn't worth it. I'm not fancy. I like fashion, but I'm not fancy. I'm a burrito guy.

Ivan ZhaoNotion | Founder & CEO

Leadership Insights:

• Authenticity Matters: Staying true to personal preferences while evolving
• Efficiency Focus: Prioritizing what delivers the most value for time invested
• Simple Complexity: Appreciating sophistication without losing simplicity

Timestamp: [01:23-04:22]

The Intersection of Art, Fashion, and Product Design

Ivan's unique combination of science and art education, plus his attention to aesthetic details, reveals how creative backgrounds influence technology leadership.

The Art-Tech Connection:

1. Dual Education Path - Studied both science and art in college, creating unique perspective
2. Fashion as Gateway - Art people naturally gravitated toward fashion and style
3. Resourceful Creativity - Bought designer clothes on eBay during college on student budget

Attention to Detail Philosophy:

• Tactile Awareness: Touches fabrics and materials to understand quality and construction
• Material Intelligence: Can distinguish between laminated vs. solid wood tables instantly
• Environmental Consciousness: Pays attention to surroundings and how they affect experience

The Table Story:

I like to touch things. So if it's a fabric, I sometimes just like to touch it, understand it. And here you can tell, okay, this is laminated. So it's an okay table. Not the fanciest. It doesn't need to be fancy, but it could be oak. It could be wood. Proper wood will make a difference.

Ivan ZhaoNotion | Founder & CEO

Product Implications:

• Quality Without Pretension: Appreciating good materials without needing luxury branding
• Functional Aesthetics: Style serves purpose, not just appearance
• Detail Obsession: Small material choices compound into overall experience quality

Timestamp: [05:49-07:57]

Essential Insights:

1. The Creator Economy Gap - There's a fundamental difference between having taste, describing ideas, and actually building them - this gap is where opportunity lies
2. Simplicity as Strategy - Preferring burritos over Michelin dining isn't just personal preference, it's a business philosophy about efficiency and transparency
3. Art Enhances Technology - Creative backgrounds provide unique advantages in product development, from aesthetic sensibility to material awareness

Actionable Insights:

• Consolidate Before You Automate - Build integrated tool foundations before attempting AI agent implementation
• Maintain Authentic Preferences - Personal authenticity in leadership creates stronger company culture and decision-making
• Invest in Detail Awareness - Small material and design choices compound into significant competitive advantages

Timestamp: [00:00-07:57]

People Mentioned:

• Joubin Mirzadegan - Partner at Kleiner Perkins and podcast host
• Danny Fernandez - Former Slack executive who later joined Sequoia Capital, witnessed Ivan's table-touching story

Companies & Products:

• Notion - Ivan's company focused on workspace collaboration and organization tools
• Kleiner Perkins - Venture capital firm hosting the Grit podcast
• Slack - Communication platform where Danny Fernandez worked before Sequoia
• Sequoia Capital - Venture capital firm where Danny Fernandez moved from Slack

Technologies & Tools:

• Knowledge Work Agents - Emerging AI technology for automating knowledge-based tasks
• eBay - Platform Ivan used to buy designer clothes during college on student budget
• DoorDash - Food delivery service the couple uses while maintaining dining formality

Concepts & Frameworks:

• The Creator Gap Theory - The space between having taste, describing ideas, and implementing them
• Computing as Medium - Ivan's philosophy that computing should be shapeable by everyone, not just programmers
• Consolidation Strategy - Notion's approach of integrating tools before building automation

Timestamp: [00:00-07:57]

The Philosophy of Lived-In Workspaces

Ivan reveals why he believes that offices that are "too good" can actually be a warning sign for business failure, and how authentic environments drive both culture and talent acquisition.

The Craftsman Office Vision:

1. Early 1900s Craftsman Style - Wood paneling, built-in shelves for books and meaningful objects
2. Authentic Materials Over Polish - Prefers less shiny wood that feels honest and lived-in
3. Malleable Spaces - Environments where you can move things around and don't take the space too seriously

The "Too Good Office" Theory:

I believe if you have too good an office, your business goes down because you're not focused on the right thing.

Ivan ZhaoNotion | Founder & CEO

Why This Matters for Talent:

• Recruiting Secret Weapon: Candidates visit the office and see the attention to craft and detail
• Cultural Signal: The environment demonstrates care for people and quality in everything
• Authenticity Over Luxury: Honest materials and lived-in feeling trump expensive finishes

The Pragmatic Balance:

• Accept Imperfection: When the wood veneer came out shinier than desired, he chose pragmatism over perfection
• Cost-Benefit Analysis: Three floors of wood replacement wasn't worth the improvement
• Focus on What Matters: Don't let perfect become the enemy of good in non-critical areas

Timestamp: [08:04-12:30]

The Founder's Sensory Advantage in Product Development

Ivan's ability to detect tiny performance differences reveals how deep product intuition becomes second nature when you live in your own creation daily.

The Title Lag Discovery:

1. Millisecond Detection - Can feel when typing in page titles is slightly laggier than typing in page bodies
2. Technical Understanding - Knows the lag happens because titles render in multiple places simultaneously
3. Daily User Perspective - Lives in the product like living in an office, noticing subtle changes

The Three-Gap Theory:

The difference between your taste and ability to describe — there's a gap. And ability to make — there's another gap.

Ivan ZhaoNotion | Founder & CEO

Levels of Product Awareness:

• Feel Level: Random great CEO could sense something feels off but couldn't articulate why
• Describe Level: Interior designer knows why a room feels great and can explain the reasons
• Make Level: Software maker knows what causes bugs and how to fix them

The Founder Advantage:

If you're a software maker, you actually know what the bugs are. I know how things are roughly made, so I can describe it and I know how to fix it.

Ivan ZhaoNotion | Founder & CEO

Why This Matters:

• Instant Bug Detection: Founders who use their product daily catch issues others miss
• Technical Empathy: Understanding implementation helps prioritize fixes effectively
• Competitive Edge: This level of product intuition compounds over time

Timestamp: [12:38-15:08]

Understanding the Hierarchy of Creative Ability

The conversation reveals a fundamental framework for understanding why some people can appreciate quality while others can both recognize and create it.

The Creative Hierarchy:

1. Taste Level - You know when something feels right but can't explain why
2. Analytical Level - You can articulate what makes something work well
3. Creation Level - You can actually build the thing you envision

Real-World Applications:

Restaurant Experience:

• Feel: "I like this restaurant's ambiance"
• Analyze: "The lighting is warm, materials are natural, space feels intimate"
• Create: Actually design restaurants with those specific elements

Software Experience:

• Feel: "This app feels slow and clunky"
• Analyze: "The title rendering is causing lag because it updates multiple UI elements"
• Create: Architect the code to optimize rendering performance

The Unconscious Quality Detection:

When you walk into a nice room, you'll be able to feel you like a bar when walking, or when you walk into a restaurant you like the ambiance, but you cannot explain why you like it.

Ivan ZhaoNotion | Founder & CEO

Why Founders Have an Edge:

• Living in the Product: Daily usage creates sensitivity to micro-issues
• Technical Understanding: Knowing how things are built enables precise problem diagnosis
• Iteration Capability: Can immediately act on insights rather than just observe them

Timestamp: [13:54-15:08]

Essential Insights:

1. The Paradox of Perfection - Offices that are "too good" signal misplaced priorities, while authentic, lived-in spaces demonstrate focus on what matters
2. Founder Product Intuition - Daily usage creates superhuman sensitivity to micro-performance issues that compound into major competitive advantages
3. The Three-Gap Framework - Understanding the hierarchy of taste, description, and creation explains why some people build better products than others

Actionable Insights:

• Use Your Own Product Daily - Founders who live in their software catch performance issues that formal testing misses
• Invest in Authentic Environments - Office design becomes a recruiting and culture tool when it demonstrates genuine care for craft
• Develop Technical Taste - Bridge the gap between feeling quality and creating it by understanding how things are made

Timestamp: [08:04-15:08]

Companies & Products:

• Notion - Ivan's company, known for design excellence and aesthetic beauty in productivity software
• Notion Office - Recently moved downtown location featuring early 1900s craftsman style design

Concepts & Frameworks:

• Three-Gap Theory - The hierarchy of taste (feeling), description (analyzing), and creation (making)
• Too Good Office Theory - Belief that overly polished offices indicate misplaced business priorities
• American Craftsman - Early 1900s architectural approach emphasizing honest materials and functional beauty
• Product Intuition Development - How daily usage of your own product creates sensitivity to micro-performance issues
• Technical Empathy - Understanding implementation details to better prioritize and fix product issues

Timestamp: [08:04-15:08]

The Strategic Philosophy of Controlled Imperfection

Ivan reveals his counterintuitive approach to product development - deliberately stopping short of perfection to maintain the right balance between craft and business utility.

The 7 Out of 10 Philosophy:

1. Sweet Spot Strategy - Happy zone is around 7.5 out of 10 in craft and detail
2. Business Balance - Pushing beyond 7-8 optimizes too much for craft, not enough for utility
3. Pride Threshold - Won't ship anything below personal pride standards, but doesn't need perfection

The Trade-off Framework:

If you push that too far — at least I believe if you push that too far — you're optimizing too much for the craft and maybe beauty, but not enough for the business and utility.

Ivan ZhaoNotion | Founder & CEO

Scientific vs. Taste Metrics:

• Scientific Measurement: Revenue and growth metrics reflect business performance
• Taste Measurement: Personal pride and aesthetic standards guide quality decisions
• Balance Point: Finding intersection where both metrics are satisfied without over-optimization

Personal Paradoxes:

• Detailed but Not Organized: Cares deeply about craft but uses simple checkbox lists in Notion
• Still Uses Paper Notebooks: Despite building digital productivity tools
• Simplicity in Complexity: Maintains simple personal systems while building sophisticated products

I'm a very detailed person, but I prefer not to do the organization. I'm just a one-page checklist. I'm not a productivity person.

Ivan ZhaoNotion | Founder & CEO

Timestamp: [15:09-17:53]

Ivan's Honest Rankings of Product Excellence

A rare insider's perspective on which companies truly prioritize craft, and why scope is the enemy of perfection in software design.

The Craft Rankings:

1. Linear (8.5/10) - Issue tracking with exceptional attention to detail, speed, and feel
2. Figma & Notion (7/10) - High craft but challenged by expanding scope and surface area
3. Apple iOS - Still among the best-crafted detailed products despite age
4. Things (German Todo App) - Only 10 features but everything feels perfect

The Surface Area Problem:

It becomes really tricky when you have to take care of a large surface area and having high craft. It's easier to create jewelry.

Ivan ZhaoNotion | Founder & CEO

Why Scope Kills Craft:

• Focused Excellence: Easy to perfect 10 features (Things app) vs. complex platforms
• Resource Allocation: More features means less attention per feature
• Maintenance Burden: Large surface areas require constant refinement across everything

Design Community Reality Check:

If you go on design Twitter, there are endless complaints about how you can make it better.

Ivan ZhaoNotion | Founder & CEO

The Entropy Challenge:

• Natural Degradation: All software becomes more complex and less elegant over time
• Microsoft Word Example: Layers upon layers of functionality packed into ubiquitous software
• Reset Necessity: Without periodic resets, simple becomes impossible

Timestamp: [17:53-21:27]

The Inevitable Entropy of Product Evolution

A sobering look at why even the best software products degrade over time, and what it takes to maintain simplicity in an ever-expanding digital world.

The Existential Question:

If Notion is still around in 50 years, will it just be uglier?

Joubin MirzadeganPartner at Kleiner Perkins | Grit Podcast Host

The Entropy Law of Software:

Entropy erodes everything, including software.

Ivan ZhaoNotion | Founder & CEO

The Microsoft Word Warning:

• Layers of Functionality: Decades of user needs packed into one tool
• Ubiquitous but Bloated: Most-used software often becomes the most complex
• Feature Creep Reality: Success leads to more requests, which leads to more complexity

The Reset Imperative:

1. Without Reset: Continue adding features → increase surface area → drop craft quality
2. With Reset: Periodically simplify → shrink surface area → maintain utility and craft
3. The Challenge: Resetting while maintaining business momentum and user satisfaction

Why Few Companies Achieve Lasting Excellence:

• Trade-off Complexity: Balancing craft, utility, and business needs over decades
• Resource Constraints: Can't maintain 8.5/10 craft across expanding feature sets
• Market Pressure: Users demand more features while also wanting simplicity

The Physical Tool Inspiration:

• Conference Room Names: iPhone, BMW 3 Series, Toshiba rice cookers, Sony transistor radio, Singer sewing machines
• Decades of Consistency: These tools found form factors that work and stuck with them
• Material Innovation: New materials enable better trade-offs without changing core function

Timestamp: [20:14-22:43]

Essential Insights:

1. The 7/10 Strategy - Deliberately stopping short of perfection maintains the optimal balance between craft and business utility
2. Surface Area is the Enemy - Expanding scope makes high craft exponentially harder to maintain across all features
3. Entropy is Inevitable - All successful software becomes more complex over time unless consciously reset

Actionable Insights:

• Set Craft Limits - Define your quality threshold (7-8/10) and resist the urge to over-optimize beyond business needs
• Prioritize Focus - Better to excel at fewer things than to be mediocre at many
• Plan for Resets - Build periodic simplification into your product roadmap to combat natural entropy

Timestamp: [15:09-22:43]

People Mentioned:

• Dylan Field - Figma CEO facing similar trade-off challenges between scope and craft

Companies & Products:

• Linear - Issue tracking software rated 8.5/10 for craft and attention to detail
• Figma - Design platform rated 7/10, similar to Notion in craft vs. scope balance
• Apple - iPhone and iOS cited as examples of sustained high craft over decades
• Things - German-made todo app with only 10 features but perfect execution
• Microsoft Word - Example of feature bloat and complexity accumulation over time
• BMW - Original 3 Series cited as example of lasting design excellence
• Toshiba - Rice cookers mentioned for changing how 100+ million people eat rice daily
• Sony - Transistor radio and Walkman as examples of breakthrough form factor innovation
• Singer - Sewing machines as example of tools that last decades without major form changes

Concepts & Frameworks:

• 7 Out of 10 Philosophy - Strategic approach to balancing craft perfection with business utility
• Surface Area Problem - How expanding feature scope makes maintaining high craft exponentially harder
• Software entropy - Natural tendency for software to become more complex and less elegant over time
• Reset Imperative - Need for periodic simplification to maintain product quality and focus
• Physical Tool Inspiration - Learning from hardware products that maintain form and function for decades

Timestamp: [15:09-22:43]

The Osmosis Effect in Company Culture

Ivan reveals how taste spreads through teams and his personal journey from having "not much taste" in China to developing refined aesthetic sensibilities through systematic cultural immersion.

The Cultural Osmosis Theory:

1. Team Influence: Notion's design team develops similar fashion preferences (Lemaire clothes)
2. Learning Speed Variables: Depends on individual capacity and surrounding culture strength
3. Environmental Impact: Culture spreads naturally through daily proximity and shared experiences

Ivan's Childhood Foundation:

• Multi-dimensional Excellence: Good at both school and sports - rare combination showing drive
• Creative Activities: Watercolor painting and Chinese calligraphy, but no fashion sense
• Natural Difference: Knew he was "a little bit different" growing up

I was born and raised in China. Not much taste there. I wouldn't say I had aesthetic sense growing up.

Ivan ZhaoNotion | Founder & CEO

The Definitive Answer:

Osmosis. I like that word a lot. So it can definitely be learned.

Ivan ZhaoNotion | Founder & CEO

Why This Matters for Building Teams:

• Hiring for Culture Fit: Taste can be developed, so focus on learning capacity and cultural alignment
• Environmental Design: Create spaces and cultures that naturally develop aesthetic sensibilities
• Leadership Influence: Founders' taste preferences will naturally spread through osmosis

Timestamp: [22:45-24:22]

The Systematic Approach to Cultural Immersion

Ivan's methodical approach to learning Western culture reveals a framework for rapidly acquiring aesthetic and cultural fluency in any new environment.

The Language Breakthrough:

1. Reading vs. Speaking Gap: Could read/write English but couldn't understand context or speak fluently
2. TV as Cultural Teacher: SpongeBob and The Simpsons for understanding humor and cultural references
3. Joke Comprehension: "Once you understand the joke, you truly understand the language and the culture"

The Music Pre-Training Method:

• AllMusic.com Strategy: Found ranking of greatest albums from past 100 years
• Five-Star Focus: Systematically listened to all highest-rated albums
• Genre Progression: Beatles → Rolling Stones → Eric Clapton → Jazz → Multiple decades of music
• Roommate Influence: Jazz-loving roommate accelerated learning in specific genres

The Film Education:

• Criterion Collection: Systematic viewing of greatest films with film major roommate
• Aesthetic Absorption: Movies taught fashion, behavior, architecture, and photography techniques
• Visual Learning: "Movies give you a lot of aesthetics... you can watch how people dress, how they behave, the details"

In some sense, it's like pre-training for yourself, going through all the great music and movies. Movies give you a lot of aesthetics... you can watch how people dress, how they behave, the details, the architecture.

Ivan ZhaoNotion | Founder & CEO

The Photography Connection:

• Technical Skills: Learning composition and technique from movie cinematography
• Aesthetic Development: Picking up visual sensibilities from carefully curated film experiences

Why This Approach Worked:

• Systematic Coverage: Comprehensive rather than random cultural exposure
• Quality Curation: Starting with "greatest of all time" lists ensured high-quality input
• Multi-Modal Learning: Music, film, and visual arts provided different aesthetic dimensions
• Social Learning: Roommates accelerated learning through shared experiences and expertise

Timestamp: [24:22-26:46]

From No English to Billion-Dollar Startup in 13 Years

Ivan's immigration and career trajectory reveals an almost impossibly focused approach to achieving a specific entrepreneurial vision against significant odds.

The Audacious Plan:

1. Move to Canada at 17 with limited English proficiency
2. Complete education while systematically learning Western culture
3. Move to Silicon Valley to start a specific company vision
4. Use employment strategically to solve visa challenges while building network

The Inkling Strategy:

• Portfolio on Hacker News: Put his work public to attract opportunities
• Strategic Company Selection: Chose Inkling because it was "closest to Notion"
• Transparent Intentions: Told Matt MacInnis upfront about starting his own company
• Visa Solution: Used employment to solve immigration challenges while preparing

The Silicon Valley Pay-It-Forward Culture:

Matt put the first check into Notion. He introduced me to all the investor connections. You really understand how Silicon Valley works — people just pay it forward.

Ivan ZhaoNotion | Founder & CEO

The Unwavering Focus:

The intention is never to join a company or start a company. The intention is to build a thing that doesn't quite exist. That's the intent, and the only way to do it is to start your company.

Ivan ZhaoNotion | Founder & CEO

Host's Amazement:

It strikes me as a little bit strong-willed to move from China, not speaking English, learn our culture through movies and music basically, then put your flag in the ground that you're going to start this company and stick to your word.

Joubin MirzadeganKleiner Perkins | Partner

Why This Approach Was Remarkable:

• Single-Minded Purpose: Never deviated from the core mission despite attractive alternatives
• Strategic Patience: Willing to spend 1.5 years solving visa issues rather than abandoning the plan
• Cultural Intelligence: Recognized the need to deeply understand Western culture before succeeding in it
• Network Building: Understood that Silicon Valley success requires relationship cultivation
• Transparency Advantage: Being honest about intentions created unexpected allies

Timestamp: [26:46-30:41]

Essential Insights:

1. Taste is Learnable Through Osmosis - Cultural and aesthetic sensibilities spread naturally through team proximity and shared experiences
2. Systematic Cultural Pre-Training Works - Methodically consuming the "greatest hits" of music, film, and art accelerates cultural fluency
3. Unwavering Vision Beats Flexibility - Having a specific, unchanging goal and adapting tactics around it can overcome seemingly impossible obstacles

Actionable Insights:

• Curate Team Culture Deliberately - Since taste spreads through osmosis, be intentional about the cultural influences in your environment
• Use "Greatest Of" Lists for Rapid Learning - When entering new domains, start with curated collections of the highest-quality examples
• Build Strategic Relationships with Transparency - Being honest about your ultimate goals can create unexpected allies and mentors

Timestamp: [22:45-30:41]

People Mentioned:

• Matt MacInnis - Ivan's first and only boss at Inkling, now COO of Replay, provided first investment in Notion
• College Roommates - Jazz enthusiast who introduced Ivan to jazz albums, and film study major who guided him through Criterion Collection

Companies & Products:

• Notion - Ivan's company, originally conceived during last year of college
• Inkling - Matt MacInnis's desktop publishing company where Ivan worked for visa purposes
• Rippling - Where Matt MacInnis currently serves as COO
• University of British Columbia (UBC) - Vancouver university where Ivan completed his education
• Hacker News - Platform where Ivan posted his portfolio to attract job opportunities

Companies & Products Referenced for Cultural Learning:

• AllMusic.com - Website with rankings of greatest albums used for systematic music education
• Criterion Collection - Curated collection of greatest films used for cinematic education
• Lemaire - Fashion brand that Notion's design team gravitates toward

Technologies & Cultural References:

• SpongeBob SquarePants and The Simpsons - TV shows used to understand American humor and cultural context
• The Beatles, Rolling Stones, Eric Clapton - Classic rock artists in systematic music education
• Jazz Albums - Genre explored through roommate's expertise and five-star rating system

Concepts & Frameworks:

• Cultural Osmosis Theory - How taste and aesthetic preferences spread naturally through team proximity
• Pre-Training Approach - Systematic consumption of curated "greatest of all time" content for rapid cultural fluency
• Strategic Employment - Using jobs to solve specific problems (visa, network) while maintaining entrepreneurial focus
• Silicon Valley Pay-It-Forward Culture - How established entrepreneurs help newcomers succeed

Timestamp: [22:45-30:41]

The Lost Origin Story of Silicon Valley

Ivan reveals the hidden history that most tech workers don't know - how the psychedelic generation of the 1960s transformed room-sized calculators into the interactive medium that powers today's trillion-dollar industry.

The Forgotten Genesis:

1. Hippie Generation Innovation - 1960s-70s San Francisco/Stanford area counterculture applied psychedelic thinking to computing
2. Room-Sized Calculator Problem - Computers were only used for calculating taxes and missile trajectories
3. The Revolutionary Insight - Adding monitors and interactivity could create an entirely new medium

The Original Vision vs. Reality:

Their intent was computing is just like reading and writing. It's a medium that we can pick up. We can shape it just like you can write out your English sentences. Computing could be a medium that everyone can shape too.

Ivan ZhaoNotion | Founder & CEO

What Most Tech Workers Don't Know:

Most people working in tech don't know where modern tech comes from. Modern tech comes from this group of people — the hippie generation of the 60s and 70s. Those are the people who took drugs and psychedelics, and that same generation applied the same thinking to this device we call computing.

Ivan ZhaoNotion | Founder & CEO

The Betrayed Promise:

• Original Intent: Everyone should be able to shape computing like writing
• Current Reality: Only programmers can truly create - they're "the scribes of the modern era"
• Lost Innovation: Computing became an "application prison" instead of malleable medium

Why This History Matters:

• Industry Understanding: Knowing the roots helps see where technology should evolve
• Product Philosophy: Guides building tools that democratize creation rather than limit it
• Revolutionary Potential: The original vision is still largely unrealized

Timestamp: [30:47-34:35]

The Three Technologies That Could Have Changed Everything

Ivan explains how Steve Jobs saw revolutionary technology at Xerox PARC but missed the most transformative element - the one that could have prevented today's "application prison."

The Three PARC Demonstrations:

1. Graphical User Interface - Jobs saw it, loved it, took it for Mac/Lisa
2. Computer Networking - Jobs missed it, created standalone floppy-based systems
3. Object-Oriented Environment - Jobs missed the most important one

The Missed Revolution:

The most nuanced one is object or environment — allow computer to be like Lego, like object-like people can take apart, put it back together without being programmers. He didn't see that one.

Ivan ZhaoNotion | Founder & CEO

The Historical Consequence:

Steve Jobs and Bill Gates' generation popularized computers by putting PCs on every desk at home, but they locked computing, locked software into this application prison that's easier for people to understand in some ways, but a lot more rigid, capping the ceiling of how far you can go with your software.

Ivan ZhaoNotion | Founder & CEO

The Dual Class System Created:

• Application Software Makers: Programmers who can create
• Application Users: Everyone else who can only consume

Why This Matters Today:

• Ceiling Problem: Current software architecture limits how far non-programmers can customize
• Class Division: Technology reinforces rather than eliminates creative inequality
• Missed Opportunity: We could have had democratized computing 40+ years ago

The Lego Vision:

• Modular Computing: Users should be able to assemble computing components like building blocks
• No Programming Required: Complex functionality through visual composition
• Unlimited Ceiling: No artificial limits on what users can create

Timestamp: [34:35-37:10]

The Pattern of Medium Transitions Throughout History

Ivan and Joubin explore why we always use new technologies like old ones, and whether AI represents a revolution as significant as computing itself.

The Historical Pattern of Medium Transitions:

1. Television - Early broadcasters just did radio speeches on TV
2. Telephone - Initially used only for formal, telegram-like short messages
3. Automobiles - Required a person with a flag walking in front

The AI Parallel:

If you put together ChatGPT's UI next to a Google UI, it's kind of similar — search box and gives you some answers. But there's way more you can do with the language model, with AI. We just haven't fully figured out how yet.

Ivan ZhaoNotion | Founder & CEO

Why This Happens:

We tend to use the new medium like the old medium in the beginning. And the best way we can do that is through the lens of the old medium.

Ivan ZhaoNotion | Founder & CEO

The Magnitude Question:

This language model started the AI medium. It's probably as revolutionary as the computing medium. They're close to the same order of magnitude, and they're different.

Ivan ZhaoNotion | Founder & CEO

The Cloud Computing Analogy:

In the beginning, it was the same feeling of 'oh my god, look at all the advantages that we can get as a business,' but everybody was porting their pre-existing applications with all of those dependencies and trying to shove them into AWS. Eventually folks kind of realized, 'oh, we need to rewrite these things from the ground up.'

Joubin MirzadeganKleiner Perkins | Partner

Current AI Transition Challenges:

• Search Box Thinking: Most AI interfaces still mimic traditional search
• Old Dependencies: Existing applications trying to "shove" AI features in
• Rewriting Necessity: Fundamental rebuilding required, not incremental updates
• Timeline Reality: "Maybe take us half a decade a decade to figure out how to use this"

The Entrepreneurial Paradox:

There is more entrepreneurship and excitement about starting new companies, and on the other hand there is more fear that you're going to be one of those old applications that's about to be rewritten.

Joubin MirzadeganKleiner Perkins | Partner

Timestamp: [37:10-42:36]

Essential Insights:

1. The Lost Computing Vision - The original 1960s intent was for computing to be as accessible as reading and writing, but we created an "application prison" instead
2. Steve Jobs' Missed Opportunity - By not seeing the object-oriented environment at Xerox PARC, we lost 40+ years of democratized computing
3. AI as Medium Transition - We're using AI like old mediums (search boxes) when it could be as revolutionary as computing itself

Actionable Insights:

• Build for the Lego Vision - Create tools that let users compose functionality without programming
• Anticipate Medium Transition Patterns - New technologies are initially constrained by old thinking patterns
• Prepare for Fundamental Rebuilding - AI revolution will require ground-up rewrites, not incremental updates

Timestamp: [30:47-42:36]

People Mentioned:

• Alan Kay - Inventor of object-oriented programming and one of the creators of the first personal computers
• Douglas Engelbart - Inventor of the computer mouse and pioneer of human-computer interaction
• Steve Jobs - Apple co-founder who visited Xerox PARC and adapted GUI technology for mass market
• Bill Gates - Microsoft co-founder who helped popularize personal computing

Companies & Products:

• Xerox PARC - Research center where graphical user interface, networking, and object-oriented computing were developed
• Apple - Company that commercialized GUI technology in Lisa and Macintosh computers
• Microsoft - Co-creator of the PC revolution alongside Apple
• Amazon Web Services (AWS) - Cloud computing platform referenced in medium transition analogy
• ChatGPT - AI interface that still resembles traditional search boxes
• Google - Search interface pattern that AI tools are currently mimicking

Technologies & Tools:

• Macintosh - One of the first mass-market graphical user interface computers
• Apple Lisa - Apple's earlier GUI-based computer that preceded the Macintosh
• Computer Mouse - Input device invented by Douglas Engelbart for interactive computing
• Language Models - AI technology representing new medium for human-computer interaction

Concepts & Frameworks:

• Application Prison - Steve Jobs and Bill Gates' model that locked software into rigid, programmer-only creation paradigm
• Object-oriented programming - Xerox PARC's vision of modular, Lego-like computing that users could reconfigure
• Medium Transition Pattern - Historical tendency to use new technologies through the lens of old mediums
• Computing as Medium - 1960s hippie generation's vision of computing as malleable creative tool like writing
• Dual Class System - Division between application makers (programmers) and application users (everyone else)

Timestamp: [30:47-42:36]

Notion's Strategic Response to Existential Technological Change

Ivan reveals how Notion's five-year consolidation strategy has created an unexpected competitive advantage in the AI era, and why their approach differs fundamentally from traditional SaaS companies.

The Existential Question:

If the world continued to exist three years ago in the same way that it did, there wouldn't be an existential risk for Notion of somebody building the entire stack from the ground up. Now, can you refactor yourself?

Joubin MirzadeganKleiner Perkins | Partner

Notion's Unique Starting Position:

1. Different Intent: Inspired by early computing pioneers to make software malleable for end users
2. Consolidation Strategy: Spent 5+ years consolidating vertical SaaS tools into one platform
3. Lego Block Approach: Document editing, knowledge management, project management, calendar, mail all in one place

The AI Context Advantage:

It turned out this is really good for AI because AI needs the context and tools to be together. We've spent five-plus years consolidating this into one place. Now it allows us to build automated knowledge work agents that actually do the work for them.

Ivan ZhaoNotion | Founder & CEO

Why Knowledge Work Agents Haven't Emerged Yet:

• Scattered Tools: Most knowledge work happens across dozens of different apps
• Context Fragmentation: Information and tools are spread out, making automation difficult
• Integration Complexity: Unlike coding (GitHub repos, plain text files), knowledge work lacks unified context

Notion's Head Start:

Notion is one of the few companies in the past five-plus years that has actually been consolidating those contexts and tools. This allows us to build knowledge work agents, and this is what we're working on right now, and it gives us quite a good head start.

Ivan ZhaoNotion | Founder & CEO

Timestamp: [42:37-46:22]

The Technical Barriers That Make Office Automation So Much Harder Than Coding

Ivan explains why AI agents conquered customer support and coding but struggle with knowledge work, and how tool consolidation creates the foundation for breakthrough automation.

Agent Success Stories So Far:

1. Customer Support - First vertical where agents succeeded
2. Coding Agents - Recent breakthrough in development workflows
3. Knowledge Work - Still largely unrealized potential

Why Coding Agents Work:

Tools and context for coding is actually fairly self-contained. Most coding agents, all the contexts are in the GitHub repos in one place. Plain text files are easy to read and write, and the tools it needs to use are reading and writing those files.

Ivan ZhaoNotion | Founder & CEO

The Knowledge Work Challenge:

It's extremely difficult to create knowledge work agents because knowledge work today consists of a dozen different tasks that you and I do across a dozen different apps.

Ivan ZhaoNotion | Founder & CEO

The Integration Solution:

• Enterprise Search Product: Recently launched integration with 10+ external contexts
• Cross-Platform Capability: Works with Google stack, Microsoft stack, Atlassian stack
• Unified Operations: Search, aggregate, and perform knowledge work across all platforms

The Network Effect:

You no longer need to go to different places to do the different things. All the Lego blocks are in one place.

Ivan ZhaoNotion | Founder & CEO

Competitive Moat Creation:

• Context Consolidation: Five years of tool integration creates data advantage
• Agent-Ready Infrastructure: Platform designed for automation from the start
• External Integration: Not limited to Notion-only ecosystems

Timestamp: [44:48-47:01]

The Fundamental Shift in Software Development Philosophy

Ivan introduces a powerful analogy that explains why traditional software development approaches fail with AI, and how successful companies must completely reimagine their building process.

The Traditional Bridge Method:

1. Total Control: "You can pretty much build anything in your Figma file"
2. Predictable Timeline: "Maybe it take three months, might take six months, but you can get there"
3. Engineering Certainty: Build exactly what you design

The Two Classic Approaches That No Longer Work:

• Y Combinator Style: Follow customer feedback and iterate
• Steve Jobs Style: Have a vision, don't listen to customers because you know better

The Beer Brewing Reality:

Language models actually work differently. You cannot build everything you can imagine. Often times it takes you 70-80% there and never closes that gap of the remaining 20%.

Ivan ZhaoNotion | Founder & CEO

Why AI Development Is Organic:

The beer analogy means it's organic. Therefore, you don't fully control it. You cannot tell the yeast, 'hey yeast, please taste that way.' You cannot force it. You have to channel the model.

Ivan ZhaoNotion | Founder & CEO

The New Development Process:

1. Experimentation Focus: "You have to experiment a lot"
2. Integrated Teams: "Put design engineer side by side together"
3. Context-Driven: Work "with the data with the right context"
4. Trial and Error: "Just keep trying things and see what sticks"

Notion's Hard-Learned Lesson:

We tried to build a knowledge work agent a year and a half ago. We had all the ingredients there on the Notion Lego side, but the language model wasn't fully ready. You can't really force it.

Ivan ZhaoNotion | Founder & CEO

The Product Reality Gap:

If you go on Twitter, there are so many cool demos, but it's now harder to find real products because to be a real product, you need to close the gap of the remaining 20-30%.

Ivan ZhaoNotion | Founder & CEO

Organizational Challenges:

• Large Company Difficulty: "Really hard for them to once the company gets large hard to shift this way of building software"
• Process Relearning: Companies must abandon waterfall-style development
• Mindset Shift: From controlling outcomes to channeling capabilities

Timestamp: [47:15-50:24]

Essential Insights:

1. Context Consolidation Creates AI Advantage - Five years of tool integration positioned Notion perfectly for the agent era when most knowledge work remains fragmented
2. AI Development Is Organic, Not Engineered - Traditional software development approaches fail with AI because you can't force language models to deliver specific outcomes
3. The 20% Gap Problem - AI can get you 70-80% there but closing the final gap to real products is exponentially harder than demos

Actionable Insights:

• Consolidate Before You Automate - Build integrated platforms first, then layer AI agents on top of unified context
• Embrace Experimental Development - Replace waterfall planning with rapid experimentation and iteration cycles
• Channel Don't Force - Work with AI capabilities rather than trying to engineer precise outcomes

Timestamp: [42:37-50:24]

Companies & Products:

• Notion - Platform that consolidated knowledge work tools over 5+ years, now building AI agents
• Y Combinator - Startup accelerator known for customer-driven development approach
• GitHub - Code repository platform that provides self-contained context for coding agents
• Google Workspace - Productivity suite integrated with Notion's enterprise search
• Microsoft 365 - Office productivity stack integrated with Notion
• Atlassian - Software development and collaboration tools integrated with Notion
• Figma - Design tool mentioned as example of traditional software development planning

People Mentioned:

• Steve Jobs - Apple co-founder cited for vision-driven development approach that doesn't work with AI

Technologies & Tools:

• Knowledge Work Agents - AI systems that automate complex office tasks across multiple applications
• Enterprise Search Product - Notion's recently launched integration platform for external content
• Language Models - AI technology that requires organic development approaches rather than traditional engineering
• Coding Agents - AI systems that successfully automate software development tasks

Concepts & Frameworks:

• Tool Consolidation Strategy - Notion's approach of bringing vertical SaaS tools into one platform
• Context Integration - Unifying scattered information and tools to enable AI automation
• Beer vs. Bridge Development - Organic experimentation approach vs. traditional engineering methodology
• The 20% Gap Problem - Difficulty of closing final quality gap between AI demos and production products
• Agent-Ready Infrastructure - Platform architecture designed to support AI automation from the ground up

Timestamp: [42:37-50:24]

The Fundamental Shift from Selling Tools to Providing Human Work

Ivan reveals the most profound transformation in software history - the transition from tools that help humans work to AI that actually does the work itself.

The Revolutionary Capability:

When you play with this language model, the underlying capability is so different. There's a human in there. It can do more and more of the things that we do.

Ivan ZhaoNotion | Founder & CEO

The Business Model Revolution:

This is the largest shift for all software companies, like SaaS cloud software companies. It's transitioning from selling tools to facilitate work to providing the work itself.

Ivan ZhaoNotion | Founder & CEO

Traditional vs. AI-Era Software:

• Traditional Tools: Provide instruments for humans to use for business needs
• AI-Era Software: Package the human capability along with the tool
• Fundamental Change: Not making people more efficient, but replacing their work entirely

Evidence Across Industries:

1. Customer Support: "It's no longer just make your support agents more efficient. It's actually doing the support"
2. Coding Agents: "It's no longer just like IDE to help your developer tap completion but actually to provide a final output"
3. Knowledge Work: Still emerging but following the same pattern

The Capability Evolution:

The capability — the funny thing is the capability gets better every three-ish months. I don't see any chance of it stopping.

Ivan ZhaoNotion | Founder & CEO

Why Progress Will Be Slower Than Expected:

• Tooling Development: Building the stack around AI capabilities
• Organizational Adoption: Helping customers understand and evolve for AI
• Go-to-Market Challenges: Teaching new ways of working with AI-provided work

Timestamp: [50:28-53:33]

The Compounding Advantage of Consolidated Building Blocks

Ivan demonstrates how five years of tool consolidation enabled Notion to ship best-in-class AI products at unprecedented speed.

The Three AI Products Launched:

1. Enterprise Search - No need to read 20 articles, AI generates answers from your content
2. Research & Reports - AI drafts reports from internal content and data in 5 minutes vs. hours
3. Meeting Notes - AI creates better notes than humans by combining calendar, documents, transcription, and summary

The Building Block Advantage:

We built a product in two months because we already have the building blocks for this. We have a collaborative document surface area. We have a calendar product. Now we can bring in the building block of AI transcription and AI summary.

Ivan ZhaoNotion | Founder & CEO

Why Speed Matters:

• Existing Infrastructure: Core collaboration and calendar systems already built
• Context Integration: All company knowledge already lives in Notion
• Seamless Experience: Products work together rather than requiring new learning

The Compounding Effect Example:

After you finish the meeting or during your meetings, you can ask questions like 'hey, what did someone talk about in the previous meeting?' You can do that again. It compounds.

Ivan ZhaoNotion | Founder & CEO

Real Customer Impact:

• Ramp Case Study: Fully moved to Notion, reduced tooling costs by 70%
• Speed Advantage: Company can ship things much faster
• AI Agent Access: Each employee gets three-four AI agents out of the box

The Productivity Multiplication:

Imagine each employee at Ramp has those three or four AI agents out of the box. All work seamlessly with the rest of Notion and each employee. That's a lot of productivity gain.

Ivan ZhaoNotion | Founder & CEO

Timestamp: [53:39-56:23]

The Technical Reason Behind Notion's Strategic Advantage

Ivan explains why AI fundamentally prefers consolidated platforms over fragmented tools, and how this creates an insurmountable moat for integrated systems.

The Context Window Imperative:

It's no longer just that human business buyers prefer this. The model itself — we keep hearing the term 'context window' — because language models want the context to be together so they can start thinking and problem-solving for you together.

Ivan ZhaoNotion | Founder & CEO

The Fragmentation Problem:

If the context is fragmented like the SaaS era, it sort of works because humans are the glue. You go to your Slack, read some snippet messages, go to your Notion, go to your Google Docs, go to your Jira, and go to your email back and forth. All the context is stored in your brain.

Ivan ZhaoNotion | Founder & CEO

Why AI Can't Handle Fragmentation:

It's really hard for AI to do that. Humans barely get it to work, so if anything, AI prefers the context to be together, tools to be together.

Ivan ZhaoNotion | Founder & CEO

Notion's Unique Position:

We have the context and tools together. We're one of the few platforms out there that can do this. That's why I'm saying we're quite well positioned to build the knowledge organization that has yet to exist.

Ivan ZhaoNotion | Founder & CEO

The SaaS Era vs. AI Era:

• SaaS Era: Humans serve as the glue between fragmented tools
• AI Era: Models need integrated context to function effectively
• Strategic Advantage: Platforms with consolidated context become exponentially more valuable

The Technical Reality:

• Human Capability: Can mentally connect scattered information across tools
• AI Limitation: Struggles with context switching and information fragmentation
• Solution Requirements: Unified platforms where AI can access all relevant information

Timestamp: [56:29-57:39]

The Challenge of Transformation at Scale

The conversation turns to Notion's origin story and whether having 1,000 employees and a $10 billion valuation makes it harder to achieve the radical transformation that AI demands.

The Origin Story Parallel:

• Early Struggle: 4-5 years searching for product-market fit
• Team Reset: Had to fire the team and start over
• Japan Isolation: Two founders spent two years rebuilding in an apartment
• Complete Rebuild: Went from "crappy" version to what became Notion

The Current Challenge:

When you went back to Japan, did you feel like 'do I need to do that again?' Like 'do I need to... how do I find clarity?' Especially now when you know you raised at whatever $10 billion, you have thousands of employees, there's more to lose now.

Joubin MirzadeganKleiner Perkins | Partner

The Scale Difference:

• Then: Two people in an apartment with nothing to lose
• Now: Close to 1,000 employees and massive valuation
• Question: How do you reinvent when the stakes are exponentially higher?

The Existential Moment:

Do you agree it feels like a completely different step function moment in time for the company to move through?

Joubin MirzadeganKleiner Perkins | Partner

Why This Matters:

• Historical Precedent: Notion's biggest breakthrough came from radical isolation and rebuilding
• Current Requirements: AI transformation may require similar boldness
• Risk Management: Balancing innovation needs with responsibility to stakeholders
• Leadership Challenge: Finding clarity amid complexity and high stakes

Timestamp: [57:44-59:26]

Essential Insights:

1. "There's a Human in There" - AI represents the shift from tools that help humans work to systems that actually do the work, fundamentally changing software business models
2. Context Consolidation is AI's Requirement - Language models need integrated context to function effectively, making fragmented SaaS tools obsolete
3. Building Block Advantage Compounds - Five years of tool consolidation enabled Notion to ship three AI products in two months that would take others much longer

Actionable Insights:

• Transition Business Models - Shift from selling tools to providing completed work through AI-human hybrid systems
• Prioritize Context Integration - AI era success requires consolidated platforms rather than best-of-breed fragmented tools
• Prepare for Reinvention Challenges - Large successful companies must find ways to transform radically despite having more to lose

Timestamp: [50:28-59:26]

People Mentioned:

• Andrej Karpathy - AI researcher who predicted self-driving cars would take 10 years to solve corner cases and bureaucratic challenges

Companies & Products:

• Notion - Platform that consolidated tools over 5+ years, now launching AI products
• Ramp - Financial management company that fully moved to Notion, reducing tooling costs by 70%
• Slack - Communication platform mentioned as example of fragmented context
• Google Docs - Document platform representing fragmented SaaS tools
• Jira - Project management tool in the fragmented context example

Technologies & Tools:

• Enterprise Search - Notion's AI product that generates answers from internal content
• AI Research & Reports - Tool that drafts reports from internal data in minutes
• AI Meeting Notes - System combining calendar, documents, transcription, and summary
• Context window - AI technical concept referring to how much information language models can process
• IDE (Integrated Development Environment) - Traditional coding tools being replaced by AI agents

Concepts & Frameworks:

• Tools vs. Work Transition - Shift from providing tools to providing completed human work
• Context Consolidation Strategy - Bringing scattered information into unified platforms for AI effectiveness
• Building Block Methodology - Using existing components to rapidly build new AI products
• Human as Glue Problem - How humans currently connect fragmented SaaS tools that AI cannot handle
• Step Function Transformation - Radical business model changes required for AI era success

Timestamp: [50:28-59:26]

From SaaS Predictability to AI's Fog of War

Ivan reveals how the AI revolution has transformed software development from a predictable, steady process into an exciting game with infinite possibilities and unknown outcomes.

The Nintendo Trip Full Circle Moment:

Kyoto was the city that Sam and I spent two summers in, and the Kyoto mayor heard about our story. So they set up a tech conference, then we did a fireside chat with the mayor. If you asked me one day I'll be meeting the mayor and talking about that story, I would say 'wow, that would be crazy,' but here we are.

Ivan ZhaoNotion | Founder & CEO

SaaS Era vs. AI Era:

• SaaS Era: "Very boring very steady... you figure out your product market fit you figure out your go to market hire our sales team done"
• AI Era: "There's a lot of fog of war and that make the game a lot more fun, a lot more exciting"

The Excitement of Unknown Territory:

You can go in all dimensions. Nobody knows what the right answer is. We have one of the most unique hands of cards because what we did in the SaaS era by consolidating allows us to do something really unique.

Ivan ZhaoNotion | Founder & CEO

The Builder's Joy Returns:

It's really rewarding for myself in a sense to think about what you can build with this — all the Legos in the SaaS era and this new type of Legos as AI.

Ivan ZhaoNotion | Founder & CEO

The Founder Fatigue Problem:

You probably can't admit this to me, but like you know pre AI you're 8 years in. It's a slog. Like 8 years of doing anything basically your entire adult life. You're probably tired... it was kind of boring.

Joubin MirzadeganKleiner Perkins | Partner

Why AI Revitalizes Builders:

• New Ingredients: "When the ingredient changes there's just so much excitement like what new thing can you build"
• Previously Impossible: "A lot of things become really was really hard impossible before"
• Builder Fulfillment: "That's a lot of fulfillment for people who build tools"

Timestamp: [59:33-1:03:06]

The Cancun GPT-4 Sprint That Launched Before ChatGPT

Ivan shares the incredible story of how he and his co-founder skipped their entire company retreat to build Notion's first AI product, launching a month before ChatGPT made AI mainstream.

The Early Access Advantage:

Sam and I were friends with OpenAI folks and we got early access to GPT-4, and that was late 2022, and what we saw is like the world will be very different. There's a human packaged inside of this.

Ivan ZhaoNotion | Founder & CEO

The Cancun Isolation:

We actually locked ourselves into a hotel room in Mexico for a week and a half and built the first version of the AI product, and we actually launched a month before ChatGPT happened.

Ivan ZhaoNotion | Founder & CEO

The Company Retreat Sacrifice:

The company is doing dinners, lunches, probably like awards and celebrations and you and your co-founder are nowhere to be found?

Joubin MirzadeganKleiner Perkins | Partner

The Racing Mindset:

Whole company was there for the week to do a retreat and we skipped all the events except the opening keynote. We thought everybody else got early access to GPT-4 too, like 'Holy [ __ ], the race is on. Let's just get out as fast as possible.' It turns out, no, we were one of the first ones to get access.

Ivan ZhaoNotion | Founder & CEO

The Dedication Level:

• Minimal Social Participation: "I did a keynote... and I did a closing dinners toast, but besides that, we're just coding for the entire week"
• Extended Stay: "We actually stayed longer because we want to finish the prototype"
• Water Bottle Evidence: "There's a entire table packed water bottle at the end of it. Then we take a photo because it's so amusing"

The Conviction Behind the Sprint:

Once you see language model level 4, it's just — the world will be different. And that's the excitement. That's incredible. It's fun to build things with this.

Ivan ZhaoNotion | Founder & CEO

Timestamp: [1:03:06-1:05:31]

The Nomadic Rebuilding Years and Finding Flow State

Ivan reveals the personal story behind Notion's transformation, including how his co-founder's love of swimming shaped their travel-while-building lifestyle.

The Team Evolution:

1. Started Solo: Ivan began by himself after leaving Inkling
2. Mom's Support: "My mom actually helped with initial funding to get the visa"
3. Toby Joined: Second team member who left after a year
4. Simon Partnership: Core duo that rebuilt Notion
5. Team Fluctuation: "Went up to fiveish people, went back to to then me and Simon"

The Nomadic Building Period:

We traveled to Kyoto, Sicily, Hawaii. Simon loves to swim, so we usually go to places where he can swim, Cancun included. We did that for like a year and a half to two years and finished rebuilding Notion.

Ivan ZhaoNotion | Founder & CEO

The Deep Work Flow State:

If you look at Spotify annual reports — if I look at mine and the years that I was coding and designing in the weeds with Simon during those Kyoto Japan years, I spent so much time listening to music because I would just be coding and listening to music.

Ivan ZhaoNotion | Founder & CEO

The Contrast with Leadership:

Nowadays, when you run a company, you have to be in meetings all the time. So that bar is actually a lot lower. Different types of flow states.

Ivan ZhaoNotion | Founder & CEO

The Joy of Building:

First of all, it has to exist. So if it doesn't exist, there's a joy and focus to help you just working in that thing. It's fun building things, but you get lost in the flow state. It's somewhat repetitive, but it's also really fun.

Ivan ZhaoNotion | Founder & CEO

Craving the Deep Work:

Do you find yourself craving the flow state of what it was like listening to music?

Joubin MirzadeganKleiner Perkins | Partner

Oh, definitely do! Yeah, I haven't properly co-worked design for many years now. I think it's easier to get in flow step when you're coding. But I'm better at design.

Ivan ZhaoNotion | Founder & CEO

Timestamp: [1:05:41-1:08:36]

Personal Life Decisions at the Peak of Professional Success

The conversation turns personal as Ivan discusses future family plans and the trade-offs between deep work and life expansion.

The Company as Child Analogy:

I don't have kids. People say when you have kids it might be interruptive to your flow state, but it's very gratifying when you see — when you're zooming out a little bit — building a company is probably like having kids.

Ivan ZhaoNotion | Founder & CEO

The Family Decision:

Do you want kids?

Joubin MirzadeganKleiner Perkins | Partner

Oh,Yeah. We're going to have kids.

Ivan ZhaoNotion | Founder & CEO

The Support System:

Do you worry about the trade-off of what that means for the company, for your first kid?

Joubin MirzadeganKleiner Perkins | Partner

I have a really capable wife. We'll figure stuff out.

Ivan ZhaoNotion | Founder & CEO

The Efficiency Theory:

People say you get more efficient, more focused, right?

Ivan ZhaoNotion | Founder & CEO

The Gratification Balance:

There are a lot of things coming at you, but in aggregate that thing is really fulfilling.

Ivan ZhaoNotion | Founder & CEO

Why This Matters:

• Life Integration: How successful entrepreneurs balance peak professional demands with personal growth
• Support Systems: The importance of capable partnerships in handling multiple life expansions
• Efficiency Gains: How constraints can actually improve focus and productivity
• Long-term Perspective: Seeing both company building and family as fulfilling aggregate experiences

Timestamp: [1:08:47-1:09:24]

Essential Insights:

1. AI Transforms Boring Industries - The shift from predictable SaaS development to AI's "fog of war" makes building exciting again for veteran founders
2. Timing and Access Create Exponential Advantages - Getting early GPT-4 access enabled Notion to launch AI features before ChatGPT made the technology mainstream
3. Deep Work Flow States Are Addictive - Founders who've experienced pure building mode crave returning to that state despite leadership responsibilities

Actionable Insights:

• Embrace Technological Fog of War - New paradigms create opportunities for those willing to experiment in unknown territory
• Prioritize Deep Work Sprints - Sometimes the most important breakthroughs require complete isolation from normal business operations
• Design for Builder Joy - Sustainable innovation requires maintaining connection to the fundamental joy of creating

Timestamp: [59:33-1:09:24]

People Mentioned:

• Mayor of Kyoto - Japanese city official who invited Ivan for a fireside chat about Notion's story
• Sam (Simon) - Ivan's co-founder who loves swimming and traveled globally while rebuilding Notion
• Toby - Early Notion team member. left after one year
• Matt MacInnis - Ivan's former boss at Inkling, first investor in Notion
• OpenAI Team - AI company that gave Ivan and Sam early access to GPT-4 in late 2022

Companies & Products:

• Nintendo - Gaming company referenced in context of Ivan's return trip to Japan
• OpenAI - AI company that developed GPT-4 and later ChatGPT
• ChatGPT - AI product that launched after Notion's AI features
• Spotify - Music streaming service with annual listening reports that Ivan references
• Inkling - Matt MacInnis's company where Ivan worked before starting Notion

Technologies & Tools:

• GPT-4 - Advanced language model that Ivan accessed early through OpenAI connections
• Notion AI - First AI product built during the Cancun hotel room sprint

Locations & Travel:

• Kyoto, Japan - City where Ivan and Simon spent two summers rebuilding Notion
• Cancun, Mexico - Location of company retreat where Ivan and Simon built first AI product
• Sicily, Italy - One of the travel destinations during nomadic building period
• Hawaii - Another destination chosen for Simon's swimming preference
• Vancouver, Canada - Ivan's previous location before moving to Silicon Valley

Concepts & Frameworks:

• Fog of War - Ivan's metaphor for the uncertainty and excitement of AI-era software development
• SaaS Era vs AI Era - Comparison between predictable software business models and experimental AI development
• Flow State - Deep work state achieved during intensive coding and design sessions
• Builder Joy - The fundamental satisfaction that comes from creating new tools and products
• Company as Child Analogy - Comparison between building companies and raising children

Timestamp: [59:33-1:09:24]

The Self-Sufficient Builder Philosophy

Ivan reveals his unconventional approach to starting a company - beginning solo because he could handle all the essential functions himself, and how this shaped Notion's unique hiring philosophy.

The Solo Start Rationale:

I had an idea already. I can code and I can design. I can write a business plan to get my visa. So I can do most things. I don't need other people.

Ivan ZhaoNotion | Founder & CEO

The Power of Two:

Sometimes Simon and I, the two of us, can do most things a company needs. So that allows Notion to stay really small, and we sort of hire people in that shape.

Ivan ZhaoNotion | Founder & CEO

The Holistic Hiring Philosophy:

Our designer can code because we want people to make holistic trade-offs in their head — both the design context and engineering context.

Ivan ZhaoNotion | Founder & CEO

Why This Approach Works:

• Complete Self-Sufficiency: Technical skills, design ability, and business acumen in one person
• Reduced Dependencies: No need to coordinate with co-founders on core product decisions
• Quality Control: Direct oversight of all critical product elements
• Resource Efficiency: Small team can accomplish what large teams struggle with

The Scaling Strategy:

• Stay Lean: "Help the company to stay lean and stay small"
• Hire Multipurpose Talent: People who can bridge multiple disciplines
• Maintain Quality: "We're not thousands of people or a thousand people"

The Trade-off Philosophy:

• Holistic Decision Making: Team members who understand both design and engineering contexts
• Integrated Thinking: Avoid siloed thinking that leads to suboptimal products
• Efficiency Focus: Smaller teams making better decisions faster

Timestamp: [1:09:27-1:10:23]

From Software to Physical Architecture

Ivan reveals his post-Notion dreams and maintains his obsessive attention to detail even in customer support processes.

The Architecture Dream:

I would get bored, but what do you think you would do to fill your time? I might do architecture. I would love to build buildings. Creating physical products would be fun. Probably architecture.

Ivan ZhaoNotion | Founder & CEO

The Design Evolution:

Like my wife and I love interior design for our offices or for our home. Architecture is like a more adult version of that.

Ivan ZhaoNotion | Founder & CEO

The Customer Support Obsession:

I read somewhere that you get support tickets sent to your phone. Does that still happen?

Joubin MirzadeganKleiner Perkins | Partner

Yeah, it's on my phone.

Ivan ZhaoNotion | Founder & CEO

The Ambient Awareness System:

When you open your phone, there'll be one-ish thing on the very top. So I get a rough impression of what's going on. It's like ambient — you care about your office, you care about your customer, you let the ambient thing come at you.

Ivan ZhaoNotion | Founder & CEO

Why This Matters:

• Physical Creation Interest: Natural progression from digital to physical building
• Design Consistency: Same aesthetic principles applied across mediums
• Customer Connection: Direct, real-time awareness of user experience
• Ambient Monitoring: Passive but constant connection to product health

The Philosophy Behind Support Monitoring:

• Non-Intrusive: "It wouldn't bother me. It wouldn't buzz my watch"
• Contextual Awareness: Getting a sense of customer sentiment
• Care Demonstration: Physical manifestation of caring about users

Timestamp: [1:10:23-1:12:04]

Ivan's Human-First Hiring Philosophy

Ivan reveals his interview approach that prioritizes authentic human connection over formal evaluation, treating hiring as one of his core crafts.

Hiring as Craft:

I do spend a lot of effort with interviewing. That's something I care about and treat as one of my crafts.

Ivan ZhaoNotion | Founder & CEO

The Business Jacket Concept:

Usually people come to interviews — we call it a business jacket is on. You need to take off their virtual business jacket. You make sure the other person understands you are a human and you see them as a human.

Ivan ZhaoNotion | Founder & CEO

The Match Philosophy:

You are here to find a match. It's not here to judge. It's not here to critique or examine. Fundamentally it's a match — you have your value, you have your skill, we have company has a value and company has to craft a skill for that role. You figure out a match.

Ivan ZhaoNotion | Founder & CEO

The Honest Approach:

The best thing is to be very honest with each other, both take out the business jacket and spend an hour to find a match.

Ivan ZhaoNotion | Founder & CEO

Why Formal Interviews Fail:

One hour, or you have a panel of four or five people — that's only four or five hours. It's very like a blind person touching an elephant. You can't get the full picture.

Ivan ZhaoNotion | Founder & CEO

The Back Channel Solution:

If you have back channels, those people spend years with the other candidate, you have a better picture.

Ivan ZhaoNotion | Founder & CEO

The Flexible Approach:

• Craft vs. Values: Different questioning approaches based on role requirements
• Non-Procedural: "It's usually just a bag of different questions or tricks"
• Authenticity Focus: "You don't get a realness out of it" with checklists

The Podcast Parallel:

People walk in with a business jacket and the goal is to take that off as quickly as possible, but actually have a normal conversation.

Joubin MirzadeganKleiner Perkins | Partner

Timestamp: [1:12:04-1:15:16]

Using Historical Knowledge to Navigate Medium Transitions

Ivan reveals how studying philosophy and history with his wife provides frameworks for understanding the AI revolution and building in new technological paradigms.

The Learning Ritual:

We had a philosophy tutor during COVID. Every weekend if we're not working, we usually read books in history or philosophy. She's actually spent so much time in philosophy nowadays. She's almost like taking a master's or PhD on it on her own.

Ivan ZhaoNotion | Founder & CEO

The Medium Transition Framework:

We're in this bridging period from one type of medium, which is classic software, classic computing, to this new AI-powered computing. You can read about how the past mediums — like I talk about the telephone, telegram of the world transition.

Ivan ZhaoNotion | Founder & CEO

The Front Row Seat Advantage:

And now by building Notion, I have a front row seat to experiment, to see what happens and to see what sticks.

Ivan ZhaoNotion | Founder & CEO

Why Philosophy Matters for AI:

Going back to why AI is so fascinating — like philosophy or history, the overlapping ground of both.

Ivan ZhaoNotion | Founder & CEO

The Practical Application:

My interest or learning in the history and philosophy of the past allows you to apply that a little bit, not fully, otherwise it would be too much like armchair philosophy.

Ivan ZhaoNotion | Founder & CEO

The Builder's Satisfaction:

I find that really satisfying. Going back to your question — does AI make you be a different type of builder? Yes, because it's finally we have this shift from old medium to new medium, and you can build with a new medium.

Ivan ZhaoNotion | Founder & CEO

Why This Approach Works:

• Historical Patterns: Understanding how past medium transitions unfolded
• Philosophical Frameworks: Deep thinking tools for complex technological changes
• Practical Experimentation: Combining theory with real-world building experience
• Shared Learning: Partner engagement creates deeper understanding
• Long-term Perspective: Seeing current changes in broader historical context

Timestamp: [1:15:21-1:17:10]

Essential Insights:

1. Self-Sufficiency Enables Independence - Starting alone with full-stack capabilities creates more control and faster decision-making than traditional co-founder models
2. Hiring for Holistic Thinking - Recruiting people who can bridge multiple disciplines (design + code) creates more efficient and aligned teams
3. Philosophy Provides AI Navigation - Studying historical medium transitions gives frameworks for understanding and building in the AI era

Actionable Insights:

• Develop Full-Stack Capabilities - Being able to execute across disciplines reduces dependencies and increases startup speed
• Remove Interview Formality - Creating authentic human connections in hiring leads to better cultural and skill matches
• Study Historical Transitions - Understanding how past technological shifts unfolded provides valuable guidance for current AI transformation

Timestamp: [1:09:27-1:17:10]

People Mentioned:

• Simon Last - Ivan's co-founder, referenced as the other half of the "two of us can do most things a company needs"
• Philosophy Tutor - Weekend instructor who helps Ivan and his wife study philosophical frameworks
• Ivan's Wife - Iranian partner who shares interior design interests and philosophical studies, pursuing advanced self-directed philosophy education

Companies & Products:

• Notion - Company built with minimal team using holistic hiring approach
• Support Ticket System - Customer service tool that Ivan monitors directly on his phone

Concepts & Frameworks:

• Business Jacket Concept - Ivan's metaphor for formal interview personas that need to be removed for authentic connection
• Holistic Trade-off Thinking - Hiring philosophy of finding people who understand multiple disciplines simultaneously
• Match Philosophy - Treating interviews as mutual fit assessment rather than one-sided evaluation
• Back Channel References - Using informal networks to understand candidates beyond formal interview hours
• Medium Transition Theory - Framework for understanding shifts from one technological paradigm to another
• Ambient Awareness - Passive monitoring approach that provides context without creating interruption
• Full-Stack Founder Approach - Starting companies with complete technical and business capability in one person

Academic Interests:

• Philosophy Study - Regular weekend learning focused on frameworks for understanding technological change
• History Research - Studying past technological transitions to inform current AI strategy
• Architecture Interest - Ivan's post-Notion aspiration to create physical buildings and spaces

Timestamp: [1:09:27-1:17:10]

The Surprisingly Simple Routine of a Tech Visionary

Ivan reveals his refreshingly straightforward daily routine that prioritizes deep work, physical activity, and continuous learning while maintaining the "burrito over Michelin star" philosophy.

The Daily Schedule:

• Wake Up: 6:30-7:00 AM
• Sleep: 11:30 PM (7 hours total)
• Morning Ritual: Make tea for himself, coffee for his wife
• Priority Work: Writing and thinking before checking communications

The Communication Philosophy:

I try not to let my Slack notifications — I turn off notifications on my Slack and emails. I go to them. Don't let them come to me. A really important thing will come to my text messages.

Ivan ZhaoNotion | Founder & CEO

Example Morning Flow:

1. Wake up and make beverages for both partners
2. Writing session - "This morning I was trying to do some writing. I flushed out some of this ideas we just talked about"
3. Communication check - Slack and emails on his schedule
4. Exercise - "Ran for two and a half miles"
5. Preparation - Shower and head to meetings

The Philosophy Behind Simplicity:

It's not too fancy. I'm more on the burrito side than the Michelin star side.

Ivan ZhaoNotion | Founder & CEO

Evening Learning Ritual:

Usually I'm on my phone all the time. I try to read before I go to bed. Last night we were learning about this Japanese woodcut master from the early 1900s. So how woodcut blocks are made. We talk about it, then we fall asleep.

Ivan ZhaoNotion | Founder & CEO

Why This Approach Works:

• Control Over Information Flow: Accessing communications proactively rather than reactively
• Deep Work Protection: Writing and thinking before the day's interruptions
• Physical Foundation: Regular exercise supporting mental performance
• Continuous Learning: Evening exploration of crafts and techniques with his wife

Timestamp: [1:17:16-1:19:30]

The Uneven Distribution of Technological Adoption

Ivan and Joubin explore the fascinating reality that cutting-edge AI tools remain largely unknown just miles away from their epicenter, and what this means for the future of work.

The East Coast Reality Check:

I was in the east coast for the 4th of July... one afternoon some question came up and I opened up ChatGPT and I just started talking to it and everyone's like what are you doing? And they're like, So I can just talk to, I'm like, Yeah!

Joubin MirzadeganKleiner Perkins | Partner

The Outer Body Experience:

And I just had a almost like an outer body experience, no pun intended, because sometimes you forget what kind of world we live in this seven miles of a city.

Joubin MirzadeganKleiner Perkins | Partner

The Technology Distribution Law:

Well, technologies never distribute evenly. They dissipate, and the epicenter is here, and we are people who self-select to be living in this region, so they tend to pick up new things quickly.

Ivan ZhaoNotion | Founder & CEO

The Simon Coding Agent Example:

Simon, my co-founder, in the past few months — he hasn't coded for a few months now. So if you walk by his desk, he's kind of like managing five, six different windows of coding agents doing the work for him.

Ivan ZhaoNotion | Founder & CEO

The Relationship Evolution:

Our relationship with information, with work, is changing, evolving towards that — like you no longer do the work, but you're managing agents to do the work.

Ivan ZhaoNotion | Founder & CEO

The Scale Transformation:

I think the bigger part is the scale that information and work can go through a person and company will also increase. It's almost like — you go into a very packed European city like Florence versus a larger city like Dallas or Houston, it's made for cars. Scale and speed is much grander.

Ivan ZhaoNotion | Founder & CEO

The Global Adoption Timeline:

This region is probably the first to realize that, and coding is probably one of the first to realize that too. It will go to your friends on the east coast working in different industries, different sectors. How long that takes, I don't think anybody knows, but it's the shape of things to come.

Ivan ZhaoNotion | Founder & CEO

Timestamp: [1:19:30-1:24:48]

The Paradox of Silicon Valley Innovation Speed

The conversation explores whether Silicon Valley's rapid adoption of new technologies is an advantage or creates dangerous gaps with the rest of the world.

The Timing Paradox:

This is why I think timing matters so much and so often things can be right but mistimed. You thought oh my god I'm late. So he spent a week and a half in Cancun. Hold up. You realize not only are you late nobody even has access to this thing yet.

Joubin MirzadeganKleiner Perkins | Partner

The Early Realization:

You know, and so it is a good reminder that boy are we early. We're still so so early.

Joubin MirzadeganKleiner Perkins | Partner

The Forest and the Tree Problem:

And so many of these tools like like a whatever the expression is, the redwood falls in a forest and nobody hears it. Better make sure that when the tools people are ready when the tools are ready.

Joubin MirzadeganKleiner Perkins | Partner

The Bureaucracy Buffer:

Well, if people are not ready, and sometimes bureaucracy is a good thing because it can slow down things, allow the rest of the world to digest, to take time.

Ivan ZhaoNotion | Founder & CEO

Silicon Valley's Adoption Pattern:

Silicon Valley people are so open-minded. Hippie culture starts here, tech boom starts here. We're just taking the new things like there's no tomorrow. But that might not be the best thing.

Ivan ZhaoNotion | Founder & CEO

The Natural Resistance:

It's like by the time you are 20-some, 25 years old, you sort of don't want to learn new things, and that could be good, could be bad. But all organizations, all personal things need to adopt new tools going through this. Things have personal system bureaucracy against new things.

Ivan ZhaoNotion | Founder & CEO

The Unknown AI Impact:

I think with this AI wave, we don't know, but it could slow things down a little bit, but it might be necessary.

Ivan ZhaoNotion | Founder & CEO

Timestamp: [1:24:48-1:26:37]

Global Expansion to Match International Customer Base

Ivan reveals Notion's ambitious international hiring plans driven by their predominantly international customer base.

Current Office Locations:

• Product/Engineering/Design: San Francisco, New York, Hyderabad (India)
• Sales Offices: Dublin (Ireland), Sydney (Australia), Tokyo (Japan)

2024 Expansion Plans:

We're opening Paris, Munich, and London this year, too, for sales.

Ivan ZhaoNotion | Founder & CEO

The International Customer Reality:

Our customer base is 80% international, so that's why we have to travel a lot to meet them.

Ivan ZhaoNotion | Founder & CEO

Hiring Philosophy:

Yeah, always hiring.

Ivan ZhaoNotion | Founder & CEO

Why This Matters:

• Customer Proximity: Following customers globally rather than remaining US-centric
• Time Zone Coverage: Supporting international users with local teams
• Cultural Understanding: Building products for diverse global markets
• Talent Access: Tapping into global talent pools for specialized roles

Timestamp: [1:26:37-1:27:25]

The Compounding Power of Persistence

In the final moments, Ivan defines grit in a way that captures the essence of long-term value creation and the patience required for meaningful innovation.

Ivan's Definition:

I really like the work rate. It's generally a positive human characteristic. Like you go through things, doesn't matter the ups and downs, you allow whatever you believe to compound.

Ivan ZhaoNotion | Founder & CEO

The Time Element:

Usually takes many years, a long time to compound and create something unique out of the other end.

Ivan ZhaoNotion | Founder & CEO

The Core Characteristic:

Grit is the characteristic to allow that to happen, to allow compounding, and compounding creates something beautiful, usually useful.

Ivan ZhaoNotion | Founder & CEO

Why This Definition Matters:

• Beyond Persistence: Not just pushing through, but allowing belief to compound over time
• Long-term Orientation: Accepting that meaningful creation takes years, not months
• Compound Thinking: Understanding that small consistent efforts create extraordinary outcomes
• Beauty and Utility: The end result serves both aesthetic and practical purposes

The Podcast Conclusion:

I love that answer. I love this. I love this conversation.

Joubin MirzadeganKleiner Perkins | Partner

Timestamp: [1:27:25-1:28:26]

Essential Insights:

1. Simple Routines Enable Complex Work - Ivan's straightforward daily structure (7 hours sleep, morning writing, controlled communication) supports building revolutionary products
2. Technology Distribution is Extremely Uneven - Cutting-edge AI tools remain unknown just miles from Silicon Valley, creating both opportunities and timing challenges
3. Grit is About Compounding Belief - True persistence means allowing your convictions to compound over years until they create something beautiful and useful

Actionable Insights:

• Control Your Information Diet - Proactively access communications rather than letting them interrupt deep work
• Prepare for Uneven Adoption - Build products knowing that most users will be years behind the technological frontier
• Invest in Long-term Compounding - Focus on beliefs and practices that grow stronger over time rather than quick wins

Timestamp: [1:17:16-1:28:26]

People Mentioned:

• Simon Last - Ivan's co-founder who now manages multiple coding agents instead of coding directly
• Joubin Mirzadegan - Kleiner Perkins partner and podcast host
• Ivan's Wife - Partner who shares evening learning sessions about crafts like Japanese woodcutting

Companies & Products:

• Notion - Company with 80% international customer base, expanding globally
• ChatGPT - AI tool that remains largely unknown outside tech centers
• Slack - Communication platform that Ivan accesses on his schedule rather than through notifications
• Kleiner Perkins - Venture capital firm producing the Grit podcast

Locations:

• San Francisco - Headquarters for product, engineering, and design teams
• New York - Additional office for product development roles
• Hyderabad, India - Engineering and design office location
• Dublin, Ireland - Sales office location
• Sydney, Australia - Recently opened sales office
• Tokyo, Japan - Sales office (not Kyoto as Ivan clarified)
• Paris, Munich, London - New sales offices opening in 2024

Technologies & Tools:

• Coding Agents - AI systems that Simon uses to manage multiple programming tasks simultaneously
• Japanese Woodcut Techniques - Traditional craft that Ivan and his wife study for evening learning

Concepts & Frameworks:

• Technology Distribution Theory - How innovations spread unevenly from epicenters like Silicon Valley
• Agent Management Paradigm - Shift from doing work to managing AI agents that do the work
• Compounding Grit - Definition of persistence as allowing beliefs to compound over years
• Florence vs Dallas Analogy - Comparison between dense, walkable systems and sprawling, car-dependent scale
• Bureaucracy as Buffer - How organizational resistance can provide useful adoption time for new technologies

Timestamp: [1:17:16-1:28:26]