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What I Learned After 5 Years Working on Hybrid Work AI

I’m going to say something that might sound crazy. After five years of grinding away at the problem of hybrid work, building a company around it, and investing in dozens of startups in the space, I’ve come to a simple conclusion: most of what we’re doing is wrong.

We’ve been so obsessed with replicating the office online—with more tools, more meetings, more notifications—that we’ve completely missed the point. The goal isn’t to build a digital copy of our old nine-to-five. The goal is to build something better. And the path to getting there is to do less, not more.

I know, I know. It sounds like a productivity guru platitude. But I have the data to back it up. A simple shift in our approach at RemoteTeam, my previous company, led to a 27% jump in our team’s efficiency. That’s not a small number. It’s the kind of change that can make or break a startup.

This wasn’t some overnight success, though. It was a painful, soul-searching journey. There were moments when I was ready to throw in the towel, convinced that hybrid work was a failed experiment. I honestly had no idea what I was doing for a while there. I was just another founder, flailing around in the dark, trying to find a light switch.

In this post, I’m going to share the story of how we got there. The mistakes, the frustrations, and the one big idea that changed everything. This isn’t a theoretical framework. This is a real, in-the-trenches account of what it takes to make hybrid work, work.

The Allure of the Digital Office

When we first started RemoteTeam, the vision was clear. We were going to build the ultimate tool for hybrid and remote teams. We’d have everything: real-time presence indicators, virtual water coolers, sophisticated project management dashboards. We were going to solve the problem of remote work by throwing technology at it.

And for a while, it felt like we were on the right track. We raised money, hired a great team, and built a product that people seemed to like. But as we grew, I started to notice a disturbing trend. Our own team, the one building the tool, was starting to burn out.

We were drowning in a sea of our own making. We had Slack channels for everything. Our calendars were a never-ending game of Tetris. We were constantly connected, but we weren’t collaborating effectively. We were busy, but we weren’t productive.

I remember one particularly brutal week. We were pushing for a major product release, and the team was working around the clock. I was in a constant state of anxiety, jumping from one Slack conversation to another, trying to keep everything on track. By Friday, we were all exhausted. We hit our deadline, but at what cost? The team was demoralized, and the quality of the work was suffering.

That’s when I realized we had a serious problem. Our tool was supposed to be making hybrid work easier, but it was actually making it harder. We had fallen into the trap of believing that more technology was the answer. We were so focused on building the digital office that we had forgotten about the people working in it.

I had to face a hard truth: I was the problem. I was the one pushing for more features, more integrations, more everything. I was the one who believed that if we just had the right tool, all of our problems would disappear. I was wrong.

The Breaking Point

I was close to quitting. Not just on the company, but on the whole idea of hybrid work. Maybe the critics were right. Maybe it was just a fad, a temporary solution to a global pandemic. Maybe we were all just kidding ourselves.

I spent a lot of time thinking about what went wrong. I talked to other founders, read every book I could find on remote work, and spent hours just staring at our own product, trying to understand where we had gone astray. I even took a solo trip to a cabin in the woods, just to get away from it all and clear my head. I was desperate for an answer.

And then, it hit me. It was so simple, so obvious, that I couldn’t believe I hadn’t seen it before. The problem wasn’t the technology. The problem was how we were using it.

We were using technology to create a culture of constant, real-time communication. We were expecting everyone to be available all the time, to respond to messages instantly, to be “on” from the moment they woke up to the moment they went to sleep. We had created a digital sweatshop.

I realized that we needed to fundamentally change our approach. We needed to move from a synchronous to an asynchronous model of communication. We needed to give our team the time and space to do deep work, to focus on what really mattered, without the constant interruptions and distractions of real-time communication.

It was a scary thought. It went against everything I had believed about how to run a company. But I knew it was the only way forward. I came back from my trip with a new sense of purpose. I gathered the team and told them that we were going to do a radical experiment. We were going to kill all of our internal real-time communication tools. No more Slack. No more real-time presence indicators. No more virtual water coolers.

To say the team was skeptical would be an understatement. They thought I had lost my mind. But I was convinced that this was the right thing to do. I told them to trust me, to give it a try for one month. If it didn’t work, we could always go back to the old way of doing things.

The Great Unplugging

The first week was chaos. People were so used to the instant gratification of real-time communication that they didn’t know what to do with themselves. They would write an email and then pace around their home office, waiting for a response. They would post a question in our new asynchronous communication tool (we built a simple one ourselves) and then complain that no one was answering them right away.

I had to be the bad guy. I had to constantly remind people that this was a marathon, not a sprint. That the goal was not to get an instant response, but to get a thoughtful one. That it was okay to disconnect, to go for a walk, to have a life outside of work.

Slowly but surely, things started to change. People started to realize that they didn’t need an instant response to every question. They started to plan their work more carefully, to think through their questions before they asked them. They started to have more time for deep work, for the kind of focused, creative thinking that is so essential for innovation.

And then, something amazing happened. The quality of our work started to improve. Dramatically. We were shipping better code, designing better products, and having more productive conversations. We were less stressed, more focused, and more engaged.

At the end of the month, I pulled the data. The results were staggering. Our team’s efficiency, which we measured by a combination of tasks completed, bugs fixed, and features shipped, had increased by 27%. That’s not a typo. Twenty-seven percent.

I presented the findings to the team, and they were blown away. The very people who had been the most skeptical were now the biggest advocates for our new way of working. We had stumbled upon something powerful, something that had the potential to change the way we think about work itself.

The Asynchronous Advantage

So, what exactly did we do? What were the “exact steps” that led to this transformation? It wasn’t about some magic tool or a complicated new process. It was about a fundamental shift in our mindset. Here’s what we did:

• We embraced asynchronous communication. We made a conscious decision to move away from real-time communication tools like Slack and towards asynchronous tools that allow for more thoughtful, deliberate conversations. This gave our team the time and space to do deep work, without the constant interruptions and distractions of real-time notifications. For anyone looking to do the same, I highly recommend reading my post on how to build a culture of async communication.

• We redefined “productivity.” We stopped measuring productivity by the number of hours people worked or the number of messages they sent. Instead, we started measuring it by the quality of their output. This shifted the focus from being busy to being effective.

• We trusted our team. We gave our team the autonomy to work when and where they wanted, as long as they were getting their work done. This created a culture of trust and accountability, where everyone felt empowered to do their best work.

• We invested in the right tools. While we killed our real-time communication tools, we invested heavily in tools that support asynchronous collaboration. This included a shared knowledge base, a project management tool with clear deadlines and owners, and a simple, in-house tool for asynchronous conversations. The key is to find tools that fit your workflow, not the other way around. I wrote about some of my favorite tools in my post on the best AI tools for digital nomads.

This shift to an asynchronous model wasn’t just about improving productivity. It was about creating a better, more sustainable way of working. It was about giving our team the freedom and flexibility to live their lives, without sacrificing their careers.

The Future of Work is Asynchronous

My experience at RemoteTeam convinced me that the future of work is asynchronous. It’s not about being in the same place at the same time. It’s about having the right tools, the right processes, and the right culture to collaborate effectively, regardless of where you are or when you work.

This is why I’m so excited about the new wave of AI-powered tools that are emerging in the hybrid work space. Companies like Anthropic, OpenAI, and Scale AI, which I’ve been fortunate enough to invest in, are building the foundational models that will power the next generation of work tools. These tools will help us to automate the tedious, repetitive tasks that take up so much of our time, and to focus on the creative, strategic work that really matters.

Imagine a world where you have an AI assistant that can summarize long email threads, draft responses to common questions, and even schedule meetings for you. A world where you can have a thoughtful, asynchronous conversation with your team, without the pressure of having to respond in real-time. A world where you can do your best work, from anywhere in the world.

This isn’t some far-off, futuristic vision. This is happening right now. And it’s going to change everything.

Of course, AI is not a silver bullet. It’s a tool, and like any tool, it can be used for good or for ill. It’s up to us to ensure that we’re building a future of work that is more human, not less. That we’re using AI to augment our abilities, not to replace them. That we’re creating a world where everyone has the opportunity to do meaningful, fulfilling work.

I don’t have all the answers. No one does. But I’m more optimistic than ever about the future of work. We’re at the beginning of a new era, an era of unprecedented creativity, innovation, and collaboration. It’s going to be a wild ride, but I, for one, can’t wait to see what happens next.

My takeaway for you is this: don’t be afraid to challenge the status quo. Don’t be afraid to experiment, to try new things, to fail. The path to building a better future of work is not a straight line. It’s a messy, winding road, with lots of twists and turns along the way. But if you’re willing to embrace the chaos, to learn from your mistakes, and to never stop pushing for something better, you might just be surprised at what you can achieve. '''

Frequently Asked Questions

How long did it take to see results?

Most meaningful business results take 3-6 months to materialize. Anyone promising overnight success is selling something. The companies in my portfolio that grew fastest were the ones that stayed patient and consistent.

Can these results be replicated?

The specific numbers will vary, but the underlying patterns and principles are transferable. The key is understanding the context behind the results, not just copying the tactics. Every company has unique constraints that shape what works.

What would you do differently looking back?

I'd move faster on the things that were working and cut the things that weren't sooner. Most founders, myself included, hold onto failing strategies too long because of sunk cost. Speed of learning is everything.