How a Charity Startup Survived Two Near-Death Experiences (and What It Means for Nonprofits)

When the Ground Shifts, You Either Move or Fall

Notion, that productivity tool everyone seems to use, didn't have a straight path to success. It started in 2013, hit a $10 billion valuation by 2021, and by 2025, its annual recurring revenue topped $600 million—half of that from AI products. But the founder, Ivan Zhao, will tell you the company nearly died twice. The first time, they were broke and clueless about product-market fit. The second time, AI threatened to make their entire approach obsolete. For charities, the parallel is uncomfortable: when the world changes—new tech, different donor habits, a pandemic—sticking with the old playbook is a slow-motion suicide.

The Kyoto Pivot: Strip Everything Down

Notion's first rebuild happened in a cramped Kyoto apartment. The company was out of money, the team had been let go, and Zhao and his co-founder basically retreated to Japan to ask a brutal question: what problem are we actually solving? They cut everything that didn't answer that. Nonprofits rarely do this. We get attached to programs we've run for years, even when the impact has faded. We keep partnerships that drain us because ending them feels like failure. But sometimes you have to kill your darlings. That might mean sunsetting an initiative that's underperforming or walking away from a donor who wants to micromanage everything. It's painful, but it's survival.

AI: The Second Wake-Up Call

When GPT-4 launched in 2023, Zhao felt like he'd been slapped. He realized AI wasn't just a feature to add—it would transform how knowledge work happens. Notion had already dabbled with an AI writing tool, but Zhao envisioned agents that could understand context, retrieve info, and execute tasks. They spent 18 months building that, and it nearly broke them because they were ahead of the tech. For charities, AI is a similar jolt. Donors now expect personalized emails, real-time impact updates, and efficient operations. But slapping a chatbot on your website isn't the answer. It's about rethinking how you deliver services, manage volunteers, and talk to supporters. The tech isn't perfect yet, but if you wait until it is, you'll be too late.

From Toolbox to AI Workspace

Notion shifted from being a simple document store to an AI workspace. Now it offers AI search, meeting notes, and agents that automate workflows. The key? Context. All those documents, tasks, and decisions become the raw material for AI. For a charity, your context is your data: donor histories, volunteer schedules, program outcomes, community feedback. If you can organize that data and feed it to AI, you can personalize fundraising, streamline reporting, and even predict where help is needed most. But that requires a deliberate effort to structure your data—which most nonprofits ignore. It's not glamorous, but it's foundational.

Jazz Band, Not Marching Band

Zhao describes Notion's ideal organization as a jazz band, not a marching band. Marching bands follow a script; jazz bands have structure but allow improvisation. In the AI era, change happens weekly, not quarterly. Charities face that same reality: donor preferences shift, crises erupt, funding landscapes change. A rigid hierarchy might keep things orderly, but it kills innovation. Instead, empower your team to respond to new situations. That doesn't mean chaos. It means clear roles but flexible execution. For example, instead of having a separate comms team that waits for program updates, let program staff share stories directly with donors when something impactful happens. It's messier, but it's real.

Hiring for Taste and Initiative

Notion changed its hiring criteria. With AI making basic skills easier, they now look for taste and initiative. Taste means knowing what good looks like; initiative means acting without waiting for permission. For charities, this is a game-changer. You don't need a huge staff of writers or coders—AI can handle that—but you need people who can ask the right questions, spot opportunities, and drive projects forward. When hiring, look for candidates who have built something on their own, who show curiosity, and who aren't afraid to experiment. Also, consider a 'barbell' structure: a few seasoned leaders plus energetic younger staff, rather than a thick middle layer. That's what Notion did, and it worked.

Marketing: Split the Mission from the Money

Notion split its marketing department into two: one focused on storytelling, the other on revenue generation. Storytelling stays close to the product; the revenue side supports sales. For charities, this means separating your mission-driven communications from your fundraising. Your brand story should attract donors emotionally, but you also need a direct-response arm that converts interest into donations. Many charities struggle with this, treating every email as a fundraising pitch. Instead, create distinct channels: one for inspiring stories, another for urgent appeals. And don't underestimate the human element. Even with AI, donors want to hear from people. Notion learned that enterprise sales can't be fully automated; trust requires human contact. Similarly, major donors want a personal relationship, not just automated acknowledgments.

AI Is Not Just About Cost Savings

Many organizations adopt AI to cut costs, but Notion sees it as transforming knowledge work. For charities, this means using AI to enhance your impact, not just to reduce expenses. For example, AI can help you analyze community needs, match volunteers to opportunities, or summarize feedback from beneficiaries. The real value is in making your knowledge work for you. If your charity has decades of data, AI can uncover trends that inform strategy. But this only works if your data is organized. So, invest time in cleaning up your databases and ensuring proper permissions. The future is not about having a static knowledge base; it's about making that knowledge actionable through AI.

Leaders Must Get Their Hands Dirty

Zhao advises founders to personally experiment with AI, not just read about it. For charity leaders, this means trying out AI tools yourself, seeing what they can do, and thinking about how they apply to your mission. You can't delegate this understanding to a consultant or a committee. By using AI to draft a report, analyze donor data, or plan a campaign, you'll see its potential and its limitations. That hands-on experience will guide your decisions on where to invest. It also sends a message to your team that innovation is a priority.

Don't Be Afraid to Reinvent

Notion's story shows that even successful organizations must be willing to start over. They didn't abandon their product; they rebuilt it around new capabilities. For charities, this might mean rethinking your program model, your fundraising approach, or even your target audience. The past success doesn't guarantee future relevance. If you were starting your charity today, with today's technology and social context, would you do it the same way? If not, start making changes. It's uncomfortable, but it's the only way to stay mission-driven in a world that doesn't stand still. As Zhao said, the goal is to avoid becoming an old company. For charities, the goal is to avoid becoming an old charity—stuck in the past, missing the needs of the present.