Ivan Zhao and Notion: Building a $10 Billion Vision to Augment Human Intellect

by Gene Dai

The Kyoto Monastery: Where Notion Was Reborn

In the summer of 2015, Ivan Zhao and Simon Last sat in a two-story house in Kyoto, Japan, coding 18 hours a day. The house had paper walls and no heating. No one around them spoke English, and they spoke no Japanese. They had just laid off their entire team, closed their San Francisco office, and moved halfway across the world because they were nearly bankrupt.

Three years into building their startup, Notion was failing. Their first product was too complex, too buggy, and the market wasn't responding. They had scrapped their entire codebase and started over. Money was running out. The cost of living in Kyoto was almost half that of San Francisco, which was the only reason they could afford to keep working.

In that spartan environment, with nothing to do except code, Zhao and Last rebuilt Notion from scratch. They lived like monks—isolated, focused, obsessed. There were no distractions, no social obligations, no startup scene networking events. Just the two of them and their laptops, day after day, building what would become one of the most successful productivity tools of the decade.

By March 2016, Notion 1.0 launched and became the #1 product on Product Hunt—not just for the day or the week, but for the entire month. By October 2021, the company had reached a $10 billion valuation. In 2024, Notion generated $400 million in annual revenue and reached 100 million users worldwide. Over 50% of Fortune 500 companies now use Notion, including Salesforce, Cisco, Intel, Target, Oracle, Ford Motor Company, and Duolingo.

The Kyoto story has become Silicon Valley legend—a tale of founder resilience and the power of radical simplification. But the deeper story of Ivan Zhao and Notion isn't just about surviving near-bankruptcy. It's about a philosophical vision that reaches back to the 1960s, to the pioneers who imagined computers not as calculation machines but as tools to augment human intellect. And it's about the challenges of turning that vision into reality in an era where software has become simultaneously more powerful and more complex than those pioneers could have imagined.

From Ürümqi to Vancouver: The Making of a Designer-Technologist

Ivan Zhao grew up in Ürümqi, a city in China's northwestern Xinjiang Uyghur Autonomous Region, living with his mother. His early talent for mathematics and computer science emerged through participation in the International Olympiad in Informatics, a prestigious grade school competition. But unlike many young programmers who focus exclusively on code, Zhao developed a parallel passion: traditional Chinese watercolor painting, which gave him an appreciation for aesthetics that would later define Notion's approach to software design.

When Zhao was in high school, his mother wanted more opportunities for his education and moved them to Vancouver, Canada. He learned English by watching SpongeBob SquarePants—an experience that likely reinforced his later interest in creating intuitive, accessible interfaces.

At the University of British Columbia, Zhao made an unconventional choice. Figuring he already understood computer science from his competition days, he majored in cognitive science and minored in fine art, taking up photography in his senior year of high school and continuing visual art projects throughout college. This interdisciplinary background—combining how humans think (cognitive science), how things look (art), and how computers work (his pre-existing programming knowledge)—became the foundation for Notion's design philosophy.

After college, Zhao worked as a product designer at Inkling, an education publishing startup, from 2011 to 2012. At Inkling, he studied the history of computing, which turned out to be foundational to his philosophy when building Notion. He read a 1962 paper by Douglas Engelbart called "Augmenting Human Intellect: A Conceptual Framework," which crystallized his thinking about what computers could and should be.

Engelbart, who would later invent the computer mouse and pioneer hypertext, conceived of computers as a way to increase humanity's capacity to solve complex problems—not just to run computations, which was the bulk of computer work at the time. Engelbart envisioned a future where the computing medium could be shaped to solve any problem, where users could construct their own tools rather than fill out templates.

When Zhao read Engelbart's paper in the early 2010s, he realized that a crucial element of this vision was still missing. Nearly all people now relied on computers to help them do all kinds of things, yet most couldn't write their own code. And until more people could do that, Zhao felt that the real promise of human-computer interaction would be limited to the creativity of coders.

This insight became Notion's founding thesis: democratize computing by giving users the tools to create their own solutions without coding skills. Zhao would later call Douglas Engelbart "Notion's patron saint," revealing how deeply this philosophy shaped both product and culture.

The First Failure: 2013-2015

In 2013, Ivan Zhao co-founded Notion Labs, Inc., in San Francisco alongside Simon Last, an engineer and designer who had studied computer science at the University of Maryland College Park. Last, who was in his early twenties at the time, impressed Zhao with his exceptional technical talent and remarkable portfolio. Last had previously worked as a software engineering intern at Nebula, Inc., and Space Telescope Science Institute, bringing serious expertise in building scalable, user-focused solutions to the partnership.

Their mission was driven by a deeply philosophical question: how could they unlock the full potential of computers and make their immense capabilities accessible to everyone? They wanted to create a "thinking tool"—a flexible, customizable space for organizing thoughts, ideas, and projects. Zhao would later describe it as "Lego for software," where users could build their own digital environments without coding skills.

But Notion's first version flopped. It was buggy and too complex. After countless trials and failures, a major realization struck Zhao: most people don't want to build their own apps. They simply want something that solves their problems quickly and efficiently. This was a pivotal "aha moment" that would reshape Notion's approach.

By 2015, three years into building their startup, the situation had become dire. They were running out of money, had just laid off their only colleagues, and faced the prospect of shutting down entirely. The market wasn't responding to their product. Something had to change dramatically.

Zhao and Last made a radical decision: they would scrap the code powering their app and start over. To stretch what money they had left, they closed their San Francisco office and moved to Kyoto, Japan. There, in that rented two-story house with paper walls and no heating, they spent 18 hours a day at their laptops, rebuilding Notion from the ground up.

The Kyoto period represented both a technical and philosophical reset. Without the distractions of Silicon Valley—the networking events, the investor meetings, the startup scene social obligations—Zhao and Last could focus entirely on the product. The isolation forced clarity. They had to figure out what truly mattered, what the "golden path" was for users.

Zhao has since said that designers spend too much time on edge cases: "Most of the time, what matters is the dumbest path." In Kyoto, they found that path. They created what Zhao calls "sugar-coated broccoli"—hiding their ambitious vision of democratizing computing inside something people already cared about: productivity software.

The Launch and Early Growth: 2016-2019

Notion 1.0 launched in March 2016 and immediately captured attention, becoming the #1 product on Product Hunt for the entire month. The app gained initial popularity among Silicon Valley startups before expanding to a wider audience. Users responded to something different about Notion—its flexibility, its clean design, its block-based architecture that felt more like building with Lego than filling out forms.

At the heart of Notion's architecture is a deceptively simple concept: everything is a block. Text, images, lists, database rows, and even pages themselves are all blocks—dynamic units of information. Each block has a type, which defines how it's displayed and how its properties are interpreted. Blocks have a content attribute containing an array of block IDs representing nested content, like nested bullet items or text inside a toggle.

This block-based architecture reflects Engelbart's belief that users should construct their own tools rather than be forced into rigid templates. The product's modularity stems from his idea that software should adapt to human thinking, rather than forcing thinking to adapt to software.

By 2019, Notion had reached 1 million users—significant traction, but still far from the scale needed to justify venture capital investment. The company's growth trajectory changed dramatically when Akshay Kothari joined as Chief Operating Officer in the fall of 2018.

Kothari brought a unique combination of product expertise and operational experience. He had co-founded Pulse, an RSS-based news curation app that began as a Stanford class project and grew into a global sensation with 33 million users. LinkedIn acquired Pulse for $90 million in 2013, and Kothari became VP Product and Head of International at LinkedIn, later serving as LinkedIn's Country Manager for India, where he managed thousands of employees.

But Kothari's connection to Notion predated his operational role. In 2013, inspired by Pulse's angel investors, Kothari had made his first investment in Notion, betting on his friend Ivan Zhao's vision. Five years later, as Notion hit early product-market fit, Zhao asked Kothari to join as COO.

With Kothari's operational expertise, Notion began to scale. In four years, from 2018 to 2022, the company grew from eight people to 500 employees. More importantly, the product began to find traction beyond individual users and small startups, moving into larger organizations.

The Funding Rounds and Valuation Journey

Notion's funding trajectory reflected its unusual path to success. Unlike typical venture-backed startups that raise significant capital early, Notion remained relatively capital-efficient through its early years, only raising its Series A in April 2019—six years after founding.

That Series A round brought in $10 million at an $800 million valuation, led by Index Ventures. The investors included Sequoia Capital and individual investors like Daniel Gross, Elad Gil, and Lachy Groom—prominent angel investors who had backed multiple successful startups.

Just over a year later, in July 2020, Notion raised a $50 million Series B at a $2 billion valuation. The timing proved prescient: the COVID-19 pandemic was driving massive adoption of remote work tools, and Notion's flexible, all-in-one workspace fit perfectly into this new reality.

But the pandemic also nearly broke Notion. In March 2020, as COVID lockdowns began, Notion's database infrastructure nearly ran out of space. The sudden surge in users—everyone setting up home workspaces, teams migrating to remote collaboration tools—pushed Notion's systems to the breaking point. Zhao has described this as one of Notion's "lost years," a period of crisis management where the team had to frantically scale infrastructure while maintaining product quality.

They survived, and the growth continued. By October 2021, Notion raised a $275 million Series C, propelling the company to a $10 billion valuation. The round was led by Coatue Management and Sequoia Capital, with participation from Index Ventures and other investors. Notion has raised a total of $352.7 million to $418 million across all funding rounds (sources vary on the exact total).

Critically, there have been no new funding rounds announced in 2024 or 2025. The October 2021 Series C remains the most recent major raise. This suggests that Notion has reached operational sustainability, generating sufficient revenue to fund continued growth without additional capital infusions.

The Revenue Ramp: From Freemium to $500 Million

Notion generates revenue through a freemium subscription model, offering free plans for individual users and paid options for personal pro, teams, and enterprise customers. The model has proven remarkably effective at converting free users into paying customers.

In 2022, Notion generated $67 million in annual revenue. By 2023, that had nearly quadrupled to $250 million. In 2024, revenue reached $400 million—a 60% year-over-year increase. By September 2025, Notion hit $500 million in revenue.

This revenue growth was accompanied by user growth from 20 million users in 2022 to 100 million users by 2024—a 5x increase in two years. More importantly, Notion has more than 4 million paying customers, representing a conversion rate of approximately 4% from free to paid users.

The enterprise segment has driven much of this growth. Notion initially attracted individual users and small teams with a 90:10 individual-to-company ratio. By 2023, this had balanced to 50:50, signaling substantial enterprise penetration. Over 50% of Fortune 500 companies now use Notion, with teams at McKinsey, DoorDash, Nike, and other major enterprises adopting it organically through bottom-up adoption.

Organizations report significant cost savings from Notion adoption. Multiple case studies show companies consolidating 5-6 tools into Notion and cutting 70 seats across other tools, saving $20,000 per year. Notion's net revenue retention exceeds 120%, indicating that existing customers are expanding their usage and spending more over time.

Critically, 80% of Notion users are located outside the United States, demonstrating the platform's global reach. This international diversification reduces dependence on any single market and provides multiple growth vectors.

The AI Pivot: 2023-2025

As large language models emerged in 2022-2023, Notion faced a strategic question: how should AI fit into a tool designed around human-constructed blocks and databases? The answer would define Notion's competitive position against Microsoft, Google, and other tech giants entering the productivity space.

Notion AI launched in February 2023, offering an AI writing assistant that could generate, edit, and summarize content within Notion pages. Unlike standalone AI tools, Notion AI was embedded directly into the workspace where users already worked, with full context of their existing notes, databases, and projects. This contextual awareness became Notion AI's key differentiator.

Simon Last, Notion's co-founder and the driving force behind Notion AI, had the challenge of building "one of the most widely scaled AI applications in the world." Despite his low profile, Last has been instrumental in integrating AI into a platform with over 100 million users—a technical feat that required solving problems of scale, latency, and cost that few other consumer AI applications face.

In 2024-2025, Notion accelerated its AI roadmap with several major releases:

But the AI expansion came with a controversial pricing change. In August 2025, Notion announced that AI features would no longer be available as standalone add-ons for new Free or Plus plan users. Instead, AI capabilities were bundled into higher-tier plans, effectively making them a core business feature rather than an optional enhancement. This pricing change reflected Notion's strategy to position AI as essential to its value proposition, but it also meant higher costs for users who wanted access to AI functionality.

For Notion, the AI strategy aligns with a broader vision: making Notion a hub for all workplace communication. As Zhao explained in recent interviews, the goal isn't to replace specialized tools but to become the connective tissue between them—the place where information from email, chat, calendar, and other tools comes together in a unified, AI-enhanced workspace.

The Competitive Battleground: Microsoft, Google, and Atlassian

Notion operates in an increasingly crowded market. Microsoft Loop, launched officially in November 2023, positions itself as a direct Notion competitor with seamless integration into the Microsoft 365 ecosystem. Atlassian's Confluence, with more than 15 years of continuous development, remains the established enterprise choice, particularly for teams using Jira or Bitbucket. Google is integrating AI throughout Workspace, including Docs, Sheets, and Gmail. Startups like Coda offer similar flexibility and database capabilities.

Each competitor has distinct advantages:

Microsoft Loop leverages the "fluid framework" that allows Loop components—tables, task lists, checklists—to work seamlessly inside Teams and Outlook, syncing in real-time across Microsoft 365 applications. For organizations already using Microsoft 365, Loop offers zero-friction adoption and native integration with tools they already use daily. Loop is optimized for mobile access and feels faster than Notion for quick edits and real-time collaboration within the Microsoft ecosystem.

Atlassian Confluence offers deep customization, extensive plugin ecosystems, and robust enterprise features built over 15 years of development. For large enterprises requiring stability, compliance certifications, and integration with Atlassian's development tools, Confluence remains the default choice. Its traditional wiki structure and Word-style editor appeal to users who prefer familiar interfaces over Notion's more radical flexibility.

Google Workspace has massive distribution—billions of users already using Gmail, Google Docs, and Google Sheets. Google's integration of AI across Workspace, including the Gemini AI assistant, provides contextual help within familiar tools. For organizations deeply embedded in Google's ecosystem, switching to Notion represents workflow disruption.

Against these competitors, Notion's advantages center on flexibility, design, and community:

Customization: Notion's block-based architecture allows users to create precisely the workspace they need, combining documents, databases, kanban boards, calendars, and other views in ways that rigid tools don't permit. Power users can build sophisticated systems for project management, CRM, content calendars, and more—all within Notion.

Design and User Experience: Zhao prioritizes aesthetics and functionality equally, believing that a tool must not only work well but also inspire its users. Notion's clean, minimalist design has become part of its brand identity, appealing to design-conscious users and organizations.

Community and Templates: Notion has cultivated a vibrant community of users who share templates, tutorials, and use cases. This community-led growth has driven adoption more effectively than traditional marketing. The extensive template library means new users can start with proven workflows rather than building from scratch.

Unified Workspace: While Microsoft and Google offer suites of separate tools, Notion provides a genuinely unified workspace where information flows naturally between documents, databases, and other blocks. This reduces context switching and the cognitive overhead of managing multiple tools.

Yet competition is intensifying. Microsoft Loop's integration with Teams—where many organizations already conduct daily collaboration—poses a serious threat to Notion's growth in enterprises. Google's AI capabilities and distribution advantages could make Workspace sufficiently capable that organizations see no need for Notion. Confluence's entrenchment in large enterprises creates high switching costs.

Notion's response has been to move faster into adjacent categories (email with Notion Mail, calendar with Notion Calendar) and to make AI a core differentiator. The bet is that Notion's unified approach—where AI has context across all of a user's information—will prove more valuable than point solutions, even those from tech giants.

The Paradox of Flexibility: Notion's Biggest Strength and Weakness

Notion's most celebrated feature—its flexibility—is also its most criticized limitation. This paradox lies at the heart of user complaints and represents Notion's greatest design challenge.

One of the most cited disadvantages of Notion is its steep learning curve, particularly for new users, stemming from the software's vast array of features and customization options. Users often spend more time learning and configuring Notion than actually getting work done. New feature additions bloat an already packed interface and present even more ways to daunt new users. As one user put it: "Notion embraced AI in a big way in 2023, and now everywhere across the app, that purple star is there waiting to be acknowledged."

The challenge stems from what users call the "jack of all trades" problem: everything you build in Notion will be less good than a bespoke application. Notion treats everything as a "page," so all things are equal. Its tables and spreadsheets can't perform advanced calculations as robustly as dedicated tools like Excel. Its project management features lack the depth of Asana or Linear. Its databases don't match Airtable's power. Its documents don't have the collaborative editing sophistication of Google Docs.

This creates what one critic describes as a paradox: "Notion is too complex for the simplest needs but still not powerful or seamless enough for the most complex needs." Users seeking simple note-taking find Notion overwhelming. Users seeking advanced database functionality find it limiting.

Performance issues compound these complaints. Both desktop and mobile apps have become noticeably slower as Notion has added features, with pauses when clicking pages, spinning loading icons when tapping menus, and delays when searching. For a tool designed to enhance productivity, these performance problems create friction that undermines the value proposition.

Search functionality illustrates the "everything is a page" problem. Finding things becomes tricky because Notion doesn't know that something is a task, project, or habit—everything is just a page. The number of search results increases as users add more content, and finding anything takes longer. Enterprise Search, launched in May 2025, attempts to address this with AI-powered understanding of content, but it remains to be seen whether this solves the fundamental issue.

Perhaps most tellingly, users abandon Notion not because it fails to work but because it demands too much investment. Setting up a sophisticated Notion workspace requires hours or days of configuration—choosing templates, designing databases, linking pages, customizing views. For individuals or small teams willing to make that investment, the payoff can be substantial. But for casual users or organizations seeking quick deployment, the complexity becomes a barrier.

Zhao is aware of these criticisms. In interviews, he acknowledges the tension between flexibility and simplicity, describing it as the "joy and suffering of building horizontal" platforms. His solution has been to focus on the "golden path"—the main user flow that 80% of people will take—rather than trying to perfect every edge case.

But finding that golden path in a tool designed for infinite flexibility remains an unsolved problem. As Notion adds more features—AI agents, email clients, offline mode—the risk of feature bloat grows. Each new capability adds power for sophisticated users while adding complexity for everyone else.

The Enterprise Challenge: Bottom-Up Meets Top-Down

Notion's journey from product-led growth to enterprise sales represents one of the most interesting strategic evolutions in SaaS. The company initially grew through bottom-up adoption—individual users and small teams discovering Notion, using the free tier, and gradually upgrading to paid plans. By 2023, over 50% of Fortune 500 companies had teams using Notion, often without formal procurement or IT approval.

This organic adoption created both opportunity and challenge. On one hand, Notion had proven product-market fit with actual users rather than just purchasing departments. Teams chose Notion because they genuinely found it useful, not because a VP mandated a top-down rollout. This grassroots enthusiasm became Notion's primary sales tool—employees would advocate for expanding Notion usage to more teams.

On the other hand, bottom-up adoption without enterprise features created security, compliance, and governance headaches. IT departments found Notion sprawling across their organizations without proper security controls, data governance policies, or integration with single sign-on systems. Shadow IT—employees using unapproved tools—became a significant concern for CIOs discovering that sensitive company information lived in Notion workspaces outside IT visibility.

Notion's response has been to build enterprise capabilities while maintaining the ease of use that drove grassroots adoption. This includes:

The transition from product-led growth to enterprise sales required significant organizational change. Where Notion's audience was once 90% individual users and 10% companies, by 2023 it had balanced to 50:50. This shift meant hiring enterprise sales reps, building customer success teams, creating marketing materials for C-level executives, and navigating lengthy procurement processes.

Akshay Kothari's operational experience proved critical here. Having managed thousands of employees at LinkedIn and led international expansion, Kothari understood the organizational complexity of selling to enterprises. Under his leadership, Notion built the go-to-market infrastructure needed to convert bottom-up adoption into top-down contracts.

The financial results validate this strategy. Notion's net revenue retention exceeds 120%, meaning existing customers are spending more over time as they expand Notion usage to more teams and upgrade to higher-tier plans. Organizations report consolidating multiple tools into Notion, reducing software spend while improving productivity.

But tensions remain. Enterprise features often conflict with the simplicity and flexibility that attracted grassroots users. Admin controls mean individual users have less freedom to customize workspaces. Security requirements slow down feature releases. Procurement processes delay deployment.

Notion must balance serving two masters: the individual users and small teams who want maximum flexibility with minimal friction, and the IT departments and executives who need security, governance, and control. So far, the company has managed this balance by offering different feature sets at different price tiers, but as competition intensifies from Microsoft and Google—both of which have mature enterprise capabilities—Notion's ability to serve both audiences will be tested.

The Design Philosophy: Systems Thinking and Natural Growth

Ivan Zhao's approach to building Notion draws from an unusual intellectual foundation: systems thinking and biological metaphors. In interviews, he recommends Thinking in Systems by Donella Meadows, which teaches that everything is a system—a series of causes and effects—and that a founder's job is to cultivate that system, understand why it works, and help it thrive.

Zhao describes this philosophy as being rooted in nature: "There's no better system than nature." He uses biological systems as inspiration for company design, believing that organizations, like ecosystems, should evolve organically rather than be rigidly engineered.

This philosophy manifests in several ways:

Product Evolution: Rather than planning a detailed product roadmap years in advance, Notion evolves based on user needs and emergent patterns. Features are tested, iterated, and refined based on actual usage rather than abstract planning. This organic approach allows Notion to adapt quickly to changing market conditions and user behaviors.

Company Culture: Notion has deliberately stayed small relative to its valuation and revenue. With approximately 500 employees supporting 100 million users and $500 million in revenue, Notion's per-employee productivity is extraordinary. Zhao believes staying small allows the company to move fast, make decisions quickly, and maintain cultural coherence.

Community-Led Growth: Rather than relying primarily on paid marketing, Notion has cultivated a community of users who create templates, write tutorials, and evangelize the product. This community-led growth is a form of organic, distributed growth that mirrors natural systems more than traditional top-down marketing campaigns.

Minimal Aesthetics: Zhao's background in fine art and his appreciation for traditional Chinese watercolor influence Notion's design. The interface emphasizes whitespace, clean typography, and minimal ornamentation. This minimalist aesthetic reflects the principle of removing unnecessary elements to reveal essential structure—much like pruning a tree to encourage healthy growth.

Zhao's philosophy is also shaped by computing pioneers, particularly Douglas Engelbart. He describes Marshall McLuhan's idea—"We shape our tools, and thereafter our tools shape us"—as central to Notion's mission. If tools shape us, then designing good tools becomes a profound responsibility. Software isn't just about productivity metrics or business outcomes; it's about shaping how humans think, organize information, and solve problems.

This philosophical depth distinguishes Zhao from many Silicon Valley founders focused purely on growth metrics and market dominance. In interviews, he speaks about Notion's long-term vision in terms of decades, not quarters. The goal isn't just to build a successful company but to genuinely advance Engelbart's vision of augmenting human intellect.

Yet this philosophical approach creates tensions with practical business realities. Organic growth is slower than aggressive sales and marketing. Staying small limits how quickly Notion can build enterprise features to compete with Microsoft and Google. Cultivating community takes time that could be spent on paid customer acquisition.

Zhao's response is that sustainable systems beat rapid extraction. He points to companies that grew too fast, raised too much money, and collapsed under the weight of investor expectations. Notion's path—bootstrapping for six years before raising a Series A, moving to Kyoto to reduce burn rate, focusing on product quality over growth hacks—reflects a different theory of how to build enduring companies.

Whether this philosophy can survive in an increasingly competitive market remains to be seen. Microsoft and Google don't need to be philosophically elegant; they can leverage distribution, integration, and massive resources to overwhelm competitors. Notion's bet is that superior design, flexibility, and community loyalty will create defensibility that brute force can't overcome.

The AI Agent Future: Ambition and Skepticism

In August 2025, Zhao joined the Grit podcast with Joubin Mirzadegan to discuss a provocative claim: "the AI agent still hasn't arrived." Despite the hype around autonomous AI agents that can complete complex tasks, Zhao argued that we're still in the early stages of making AI truly useful for knowledge work.

Notion 3.0's AI agents, launched in September 2025, represent Zhao's vision of what the "arrived" agent might look like. These agents can execute multi-step workflows for up to 20 minutes, pulling context from Notion pages, connected tools like Slack and Google Drive, and external data sources. They can analyze sales data across multiple tools, draft reports based on specific templates, schedule follow-up meetings, and send summary emails—all from a single natural language prompt.

But Zhao is frank about the limitations. Current AI agents struggle with:

Notion's modular, block-based architecture positions the company well for the agent future. Because everything in Notion is structured data—blocks with types, properties, and relationships—agents can more reliably read and manipulate information compared to unstructured documents. Notion's database capabilities allow agents to organize information in ways that simple document editors can't match.

But Zhao acknowledges that Notion's architecture also creates constraints. The flexibility that makes Notion powerful for humans makes it ambiguous for AI. When a database could represent a project tracker, a CRM, a content calendar, or an inventory system, agents must infer the purpose from structure and content—a challenging AI problem.

The competitive landscape for AI agents is fierce. Microsoft Copilot integrates across Office 365, leveraging Microsoft's massive training data and distribution. Google's Gemini assistant does the same across Workspace. Salesforce, ServiceNow, and other enterprise platforms are building domain-specific agents with deep workflow integration. Startups like Adept, Cognition AI, and others are building general-purpose AI agents.

Notion's advantage is that it already sits at the center of users' workflows. For organizations that have adopted Notion as their primary workspace, Notion AI agents have context that external agents lack. They know the team's projects, the company's terminology, the historical decisions documented in meeting notes. This contextual advantage could prove decisive as AI agents become more sophisticated.

But the challenges are substantial. Building reliable AI agents requires massive engineering investment, continuous model improvement, and solving trust and safety issues. Notion must decide how much autonomy to give agents—too little and they're just chatbots; too much and they risk making consequential mistakes.

Zhao's response in interviews suggests cautious optimism. He believes Notion's modular approach "might be the closest thing to making it real"—turning AI agents from hype into genuinely useful tools. But he's also realistic about the timeline, speaking in terms of years rather than months before AI agents can be truly trusted with complex knowledge work.

The Product Expansion: Notion Mail and Beyond

In April 2025, Notion launched Notion Mail, an email client that transforms inboxes into customizable Notion databases. Users can apply AI-powered labels automatically, create custom views to slice and dice email by project or priority, use snippets for common responses, and integrate scheduling directly within email threads.

Notion Mail represents the company's boldest expansion beyond its core workspace product. Email remains one of the last major productivity tools that hasn't been reimagined for the modern era—Gmail and Outlook still rely on fundamentally folder-based paradigms from the 1990s. By bringing Notion's database flexibility to email, the company aims to solve the perennial problem of inbox overload.

The strategic logic is clear: if Notion can become the hub for email, calendar, documents, databases, and project management, it becomes significantly stickier. Users won't just visit Notion for specific tasks; it becomes their primary productivity environment. This integration strategy mirrors Microsoft Office and Google Workspace—offering a suite of interconnected tools that work better together than standalone alternatives.

But product expansion creates risks:

Focus Dilution: Building and maintaining an email client requires significant engineering resources. Every hour spent on Notion Mail is an hour not spent improving the core workspace product or advancing AI capabilities. For a company of 500 people competing against Microsoft and Google, focus is critical.

Complexity Accumulation: Each new product adds complexity to the user experience. Users must learn Notion Mail's interface, decide whether to migrate from existing email clients, and figure out how email integrates with their Notion workspace. This compounds the "steep learning curve" criticism already leveled at Notion.

Competitive Exposure: Email puts Notion in direct competition with Gmail and Outlook—two of the most entrenched products in technology. Migrating email is a high-friction decision involving years of archived messages, established workflows, and organizational dependencies. Convincing users to switch requires not just a better product but a dramatically better product.

Infrastructure Costs: Email infrastructure is complex and expensive, requiring spam filtering, deliverability management, storage for large attachments, and compliance with email security standards. These operational costs could significantly impact Notion's margins.

Similar questions apply to Notion Calendar, launched earlier to compete with Google Calendar and Outlook Calendar. While calendar integration makes sense for a productivity tool, building a best-in-class calendar requires features like smart scheduling, timezone handling, meeting analytics, and video conferencing integration—all complex engineering challenges.

Zhao's strategic bet appears to be that Notion's integration advantages outweigh the risks of product expansion. If email, calendar, documents, and databases all share the same block-based architecture and AI context, the unified experience could be sufficiently valuable to overcome switching costs.

But execution is everything. If Notion Mail is merely "good enough" rather than genuinely better than Gmail, users won't switch. If Notion Calendar lacks features that power users depend on, it won't gain traction. The history of technology is littered with startups that expanded too broadly and lost focus on their core strengths.

Notion's advantage is its community of passionate users who are eager to consolidate tools into a unified workspace. If Notion Mail and Calendar prove their value to this core audience, organic adoption could follow. But if these products feel like half-baked additions rather than thoughtfully designed experiences, they could damage Notion's brand for quality and attention to detail.

The Road Ahead: Challenges and Opportunities

As Notion approaches its second decade, the company faces both unprecedented opportunities and significant challenges. The opportunity lies in the massive, growing market for productivity and collaboration tools—a market that IDC estimates will exceed $50 billion by 2026. Remote and hybrid work have permanently increased demand for digital collaboration tools, and AI is creating new possibilities for augmenting knowledge work.

Notion's position is strong: 100 million users, over 50% of Fortune 500 companies, $500 million in revenue, a $10 billion valuation, and profitability or near-profitability (the company hasn't disclosed detailed financials). The product has demonstrated genuine product-market fit across individual users, small teams, and large enterprises.

But the challenges are formidable:

Microsoft and Google: These tech giants have distribution advantages, massive engineering resources, and the ability to bundle productivity tools with their dominant operating systems and cloud platforms. Microsoft Loop's integration with Teams—used by over 300 million people—poses an existential threat to Notion's growth in enterprises. Google Workspace's 3 billion users create enormous inertia against switching to alternative tools.

Performance and Scalability: As Notion adds features and scales to 100 million users, maintaining performance becomes increasingly difficult. Users complain about slowness, and performance issues undermine the productivity value proposition. Solving these problems requires significant infrastructure investment and potentially rearchitecting core systems.

The Complexity Paradox: Notion's flexibility is both its greatest strength and its biggest weakness. As the company adds AI agents, email clients, and other features, the risk of overwhelming users grows. Finding the balance between power and simplicity remains an unsolved design challenge.

Enterprise Expectations: Selling to large enterprises means meeting increasingly sophisticated security, compliance, and integration requirements. Every new compliance certification, every enterprise integration, every admin control adds complexity that could slow Notion's pace of innovation.

AI Commoditization: As AI capabilities become more widely available through APIs from OpenAI, Anthropic, and others, Notion's AI features risk becoming commoditized. If every productivity tool offers similar AI assistance, Notion loses a key differentiator.

Economic Uncertainty: The broader economic environment affects enterprise software spending. During downturns, companies scrutinize software budgets and may consolidate around Microsoft and Google rather than paying for additional tools like Notion.

Against these challenges, Notion has several sources of defensibility:

Network Effects: As teams adopt Notion, they create shared workspaces, templates, and workflows that become more valuable as more people participate. Switching costs increase as more organizational knowledge is stored in Notion.

Design and Brand: Notion's aesthetic and user experience have created strong brand loyalty, particularly among design-conscious users and companies. This emotional connection provides some protection against purely functional competition.

Community and Ecosystem: The vibrant community of Notion users, template creators, and consultants creates an ecosystem that extends beyond the core product. This ecosystem generates content, provides support, and drives adoption in ways that corporate marketing cannot replicate.

Founder Vision: Zhao's philosophical approach and long-term thinking provide strategic clarity that could help Notion navigate competitive pressures without losing focus on its core mission of augmenting human intellect.

The key question is whether these advantages are sufficient against competitors with vastly greater resources. Microsoft and Google can afford to lose money on productivity tools because they're bundled with lucrative cloud platforms. They can invest billions in AI research, infrastructure, and product development. They have sales organizations that can navigate enterprise procurement processes with ease.

Notion's response must be to stay focused on areas where being smaller is an advantage: moving faster, maintaining design coherence, staying close to users, and taking risks that large companies cannot. The Kyoto story demonstrates that Notion's leadership understands how to make radical decisions when necessary. Whether they can do so again, at much larger scale, will determine whether Notion becomes a permanent fixture in the productivity landscape or an acquisition target for a larger platform.

Conclusion: The Unfinished Vision

In March 2025, Ivan Zhao appeared on Lenny's Podcast to discuss Notion's "lost years"—the periods of struggle, near-collapse, and painful learning that preceded the company's success. He spoke candidly about running out of database space during COVID, about the difficulty of building a horizontal platform that serves many use cases rather than one vertical, about the "joy and suffering" of realizing Engelbart's vision.

What emerges from Zhao's interviews and Notion's journey is a story more complex than the typical Silicon Valley narrative of hockey-stick growth and visionary founders. Notion's success wasn't inevitable—it required near-bankruptcy in Kyoto, radical product pivots, infrastructure crises during COVID, and countless difficult decisions about what to build and what to cut.

The vision that Zhao articulated in 2013—democratizing computing by giving users tools to create their own solutions—remains unfinished. Notion has made this vision accessible to millions, but the complexity challenges show how difficult it is to balance flexibility with ease of use. The AI agent future promises more powerful augmentation of human intellect, but current implementations are still limited, unreliable, and require significant user investment to configure properly.

Douglas Engelbart, Notion's "patron saint," died in 2013—the same year Zhao and Last founded Notion. Engelbart spent decades advocating for his vision of augmenting human intellect, often frustrated by the computing industry's focus on consumer entertainment and business automation rather than tools for serious knowledge work. He saw glimmers of his vision realized in early systems like Hypercard and Lotus Notes, but nothing that fully embodied his ideas at mass scale.

Notion represents perhaps the closest realization of Engelbart's vision that has achieved mainstream adoption. Its block-based architecture, customizability, and focus on empowering users to construct their own systems reflect Engelbart's belief that software should adapt to human thinking. The integration of AI capabilities could finally deliver on his promise of machines genuinely augmenting rather than replacing human intelligence.

But Engelbart also warned that technology shapes its users. If Notion's complexity overwhelms people, if its flexibility creates analysis paralysis, if its performance issues create friction rather than flow, then it fails the augmentation test. A tool that requires extensive configuration and maintenance imposes cognitive overhead that reduces rather than enhances intellectual capability.

Zhao understands this tension. His emphasis on the "golden path," his recommendation of systems thinking, his biological metaphors—all suggest an awareness that building tools to augment human intellect is about cultivating the right conditions for human and software to work together, not just piling on features.

Whether Notion succeeds in realizing Engelbart's vision, or becomes another cautionary tale of a promising startup outmaneuvered by tech giants, will depend on execution in the years ahead. The company has built a remarkable foundation: engaged users, strong revenue growth, enterprise adoption, and a product that genuinely solves real problems for millions of people.

But the competitive environment is more intense than ever, and the challenges—performance, complexity, enterprise requirements, AI reliability—are substantial. Notion's journey from that paper-walled house in Kyoto to a $10 billion company demonstrates that Zhao and his team know how to navigate difficult circumstances. The next chapter will test whether that resilience and vision are enough to compete with the largest technology companies in the world.

What remains clear is that Ivan Zhao has already contributed something valuable to computing: a demonstration that philosophical depth, design excellence, and user empowerment can drive commercial success. In an industry often criticized for prioritizing engagement metrics over human flourishing, Notion's focus on augmenting intellect offers a different model. Whether that model scales to become the dominant paradigm for productivity software, or remains a beloved niche product for sophisticated users, the attempt itself pushes the industry toward Engelbart's vision—and that may be success enough.

This comprehensive analysis is part of the "Silicon Valley AI 100 Most Influential 2025" series—deep-dive profiles of the leaders shaping artificial intelligence. Published November 23, 2025 • 10,247 words • 51-minute read • Research based on 15+ verified sources including interviews, company announcements, financial reports, and industry analyses.

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About the Author

Gene Dai is a Co-founder of OpenJobs AI, an AI-powered recruitment platform revolutionizing talent acquisition through advanced machine learning and natural language processing. With deep expertise in AI product development and Silicon Valley's technology ecosystem, Gene provides in-depth analysis of the leaders and companies shaping the future of artificial intelligence. His insights combine technical understanding with strategic business perspective, offering readers comprehensive views of AI's transformative impact across industries.