I’m just going to say it: the dream of an “all-in-one” productivity tool is a lie.
For years, we’ve been sold this vision of a single, magical platform that will organize your entire company. One tool to rule them all. We bought into it. We drank the Kool-Aid. And for us, that tool was ClickUp. We poured thousands of hours and dollars into it, building what we thought was our company’s central nervous system.
And now, in 2026, we’re blowing it all up. We’re breaking up with ClickUp.
This isn’t a rage-quit. It’s a strategic decision. It’s an admission that the philosophy that led us to ClickUp in the first place was flawed. After two successful exits and investing in over 200 startups, including some of the foundational AI companies of our time, my perspective on work has fundamentally changed. The way we organize ourselves and our information has to change with it.
The Honeymoon Phase: Why We Chose ClickUp
I remember the early days. Back when we were scaling RemoteTeam, the chaos was… exhilarating. And manageable. A mix of Trello boards, Google Docs, and Slack channels worked just fine. But as my angel portfolio grew, and the number of projects and people I was juggling exploded, the cracks in our ad-hoc system started to show.
We were context-switching constantly. Information was scattered. A critical piece of due diligence for one investment would be buried in a Slack thread, while the task list for a portfolio company’s marketing push was in a forgotten Trello board. It felt like we were spending more time looking for information than acting on it.
ClickUp seemed like the answer. It promised a single source of truth. Tasks, docs, goals, whiteboards, timelines—everything, all in one place. The feature list was intoxicating. We could build custom dashboards for my investment pipeline, create detailed project plans for our portfolio support, and have our own internal knowledge base. We spent weeks migrating everything, meticulously setting up our spaces, folders, and custom fields. It felt like we were finally building a real, scalable operational backbone.
For a while, it was good. We had visibility. We had structure. It felt professional. But honeymoons don't last forever.
The Slow, Painful Realization
The first sign of trouble was the slowness. Not just the app’s performance, which seemed to degrade with every new task we added, but the slowness it introduced into our own thinking. The system became a tax. Every new idea, every small task, had to be categorized, tagged, assigned, and dated within this rigid structure. The cognitive overhead started to kill our agility.
Then came the feature bloat. ClickUp can do everything, which means it does most things in a painfully mediocre way. The Docs feature was clunky compared to Notion or Coda. The Whiteboard was a toy next to Miro. We were paying for a Swiss Army knife but only ever using the screwdriver and the corkscrew, and both were a bit bent.
I had a moment of horrifying clarity last year. We were in the final stages of a deal for a company I was incredibly excited about. The closing documents were time-sensitive. The final memo, with my notes and redlines, was somewhere in ClickUp. I knew it was there. But searching for it was a nightmare. The global search was slow and returned a dozen irrelevant results. Was it in a task description? A comment? A Doc? After ten minutes of frantic searching, I gave up and found an older version in my email. We got the deal done, but the incident stuck with me. Our “single source of truth” had failed a basic retrieval test at a critical moment.
That’s when I realized: we hadn’t built a central nervous system. We had built a prison for our information.
The Great Unbundling of Productivity
My work as an investor, particularly with companies like OpenAI, Anthropic, and Scale AI, has given me a front-row seat to the next revolution in software. And it’s not about building bigger, more complex monoliths. It’s about creating smaller, smarter, and more specialized tools that do one thing exceptionally well.
We’re entering the era of the “Great Unbundling.”
Instead of one tool that does ten things poorly, we’re moving to a stack of ten tools that each do one thing perfectly. This is only possible because of AI and the power of modern APIs. The new “platform” isn’t a single piece of software; it’s a fluid, interconnected system where information flows freely between best-in-class applications.
Our new philosophy is simple:
- Use the best tool for the job. For writing, we use a dedicated writing app. For tasks, a lightweight, fast-as-thought task manager. For complex project planning, a visual tool built for that purpose.
- Let AI do the organizing. We don’t need to manually file everything into a rigid hierarchy anymore. The new generation of AI-native tools can understand context and retrieve information no matter where it lives. Search is the new organization.
- Optimize for speed and flow, not for structure. The goal is to reduce friction and cognitive load. A tool should feel like an extension of your own mind, not a bureaucratic process you have to follow.
So what does our new stack look like? It’s still evolving, but here’s the direction:
- For Tasks: We've moved to a much simpler, faster tool. Something that opens instantly and lets you capture a thought without a dozen clicks. Think less database, more notepad.
- For Documents & Knowledge: We're back to a dedicated platform built for collaboration and deep thinking. The writing experience is clean, and the organization is flexible.
- For Communication: Slack is still the king of real-time chat, but we’re more disciplined about what goes in there. It’s for conversation, not for storing information.
- The Glue: This is the most exciting part. We’re using an AI-powered search layer that connects to all of our apps—our new task manager, our document hub, Slack, email, everything. When I need that investment memo, I don’t have to remember where I put it. I just ask for it, and the AI finds it.
This is the future. Not a single, bloated application, but a constellation of sharp, intelligent tools working in concert.
Breaking Up is Hard, But Staying is Harder
Leaving ClickUp is not easy. We have years of data locked inside. The migration is a project in itself. But the cost of staying is higher. It’s the daily friction. It’s the cognitive tax. It’s the slow, creeping realization that your primary tool for getting work done is actually getting in the way of your work.
We’re not just changing tools; we’re changing our entire philosophy of productivity. We’re trading the false security of the all-in-one monolith for the speed and agility of a modular, intelligent stack. It’s a bet on a future where our tools are not containers we have to manage, but partners that think with us.
So, goodbye, ClickUp. It’s not you, it’s us. We’ve just outgrown the idea that one tool can solve everything.
Frequently Asked Questions
How can I apply this thinking to my own situation?
Start by identifying the core principle behind the opinion, not the specific example. Then ask yourself: does this principle apply to my context? If yes, test it in a small, low-risk way before going all in.
What's the most common pushback you get on this?
People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.
What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.