You're probably using AI coworking all wrong. I was too. Here's the painful story of how I learned to do it right.
I almost gave up on AI coworking. I’ve built and sold two companies, RemoteTeam and MovieLaLa, and I’ve invested in over 200 startups, including some of the biggest names in AI like Anthropic and OpenAI. I’ve seen a lot of hype, and I’ve seen a lot of things fail. AI coworking felt like it was heading for the hype graveyard. At RemoteTeam, we tried everything. Shared virtual spaces, AI project managers, you name it. It was a disaster. The tools were clunky, the team hated them, and it felt like we were just burning money.
Then, during one of our all-hands, a junior engineer said something that hit me like a ton of bricks: ‘We’re trying to be a remote company that acts like an office-based one.’ He was right. We were trying to digitally replicate the physical office, and it was killing our productivity. That single comment sparked a complete overhaul of our strategy. We stopped trying to be ‘in the office, online’ and started building a truly remote-first culture. The results were insane. We increased our efficiency by 70%, and just 580 days after we incorporated, RemoteTeam was acquired by Gusto. The entire process, from pitching investors to the final M&A, was done 100% remotely. In this post, I’m breaking down how we did it.
The Async Advantage: Why Real-Time is the Enemy
The biggest mistake I see companies making with AI coworking is trying to force real-time collaboration. They’re obsessed with presence, with knowing who’s online and what they’re doing at any given moment. That’s a recipe for disaster. It leads to constant interruptions, notification fatigue, and a culture of performative work.
At RemoteTeam, we went all-in on async. I’m talking a full-blown cultural shift. We realized that the real power of AI coworking isn’t about watching people work; it’s about helping them work better. It’s about creating a calm, focused environment where people can do deep work, on their own schedule. We used AI to facilitate this, not to micromanage it.
Here’s what that looked like in practice:
- AI-powered meeting summaries: We used a tool that automatically transcribed and summarized our meetings, so no one had to worry about missing a key decision. This alone saved us hours each week.
- Smart notifications: Instead of bombarding everyone with every little update, we used an AI that would only surface the most relevant information to the right people. This was a game-changer for reducing noise and improving focus.
- Automated status updates: We replaced our daily stand-ups with an AI that would prompt everyone for a quick update and then compile it into a single, easy-to-read digest. This gave us all the signal with none of the noise.
Onboarding in the Age of AI
Onboarding is another area where AI coworking can have a massive impact. In a remote-first world, you can’t just have a new hire shadow someone for a week. You need a more structured, scalable approach. That’s where AI comes in.
We built an AI-powered onboarding buddy that would guide new hires through their first few weeks. It would answer their questions, point them to the right resources, and even introduce them to their new colleagues. It was like having a personal concierge for your new job.
The results were incredible. Our new hires were ramping up faster than ever before, and they felt more connected to the team from day one. We even saw a significant increase in our retention rates.
Building Culture with Code
One of the biggest challenges of remote work is building a strong company culture. When you’re not all in the same room, it’s easy to feel disconnected. But AI can help bridge that gap.
We used AI to create virtual water cooler moments, to facilitate casual conversations, and to celebrate our wins as a team. We even built an AI that would analyze our communication patterns and suggest ways to improve our collaboration.
It might sound a little out there, but it worked. We built a culture of trust, transparency, and mutual respect, all with the help of a few smart algorithms. And that, more than anything, is what made our experiment with AI coworking a success.
My 2026 Prediction
So, what’s my prediction for 2026? AI coworking will be the default for any company that wants to win. But it won’t be the clunky, real-time surveillanceware that’s being peddled today. It will be async-first, deeply intelligent, and woven into the very fabric of how we work.
It will be less about where you work, and more about how you work. And that, I believe, is a future worth building.
I’m not just talking about my own experience at RemoteTeam. I’ve seen this pattern across my portfolio of 200+ investments. The companies that get this right are the ones that are scaling fast and attracting the best talent. They’re more efficient, more innovative, and frankly, they’re just better places to work. These are the companies that will define the next decade.
If you’re struggling with AI coworking, my advice is simple: stop trying to build a digital office. Start building a remote-first culture. The tools are just there to support the culture, not the other way around. Get that right, and you’ll be unstoppable.
The Dark Side of Real-Time: A Personal Failure
I want to share a story from the early days of MovieLaLa. We were a small, scrappy team, and we were obsessed with speed. We lived in a perpetual state of real-time. Constant notifications, endless meetings, and the pressure to be always-on. I thought this was the only way to build a successful startup. I was wrong.
We had a brilliant engineer, let's call him Alex. He was one of the most talented coders I’ve ever worked with. But he was an introvert. He thrived in long, uninterrupted blocks of deep work. Our real-time culture was slowly killing his productivity and his spirit. He was constantly being pulled into meetings, bombarded with questions, and expected to respond instantly. His work suffered, and he eventually burned out and quit. Losing Alex was a huge blow to the company, and it was a wake-up-call for me. I realized that my obsession with real-time was not only inefficient, but it was also toxic.
That experience taught me a valuable lesson: the most important resource in any company is not time, but attention. And real-time communication is the enemy of attention. It creates a culture of constant distraction, where nobody can focus on what really matters. That’s why I’m so passionate about asynchronous communication. It’s not just about a different set of tools; it’s about a different way of thinking. It’s about respecting people’s time and attention, and creating an environment where they can do their best work.
The AI-Powered Onboarding Buddy: A Deeper Look
Our AI onboarding buddy at RemoteTeam wasn't just a glorified FAQ bot. It was a personalized guide that helped new hires navigate the complexities of our remote-first culture. Here's a closer look at how it worked:
- Personalized Learning Paths: The buddy would create a customized onboarding plan for each new hire based on their role, their team, and their prior experience. A new engineer would get a different onboarding experience than a new marketer.
- Proactive Check-ins: The buddy would proactively check in with new hires to see how they were doing, answer their questions, and offer support. It would even schedule virtual coffee chats with their new teammates to help them build relationships.
- Just-in-Time Training: Instead of front-loading all the training in the first week, the buddy would deliver it in small, bite-sized chunks, right when the new hire needed it. For example, if a new hire was about to have their first one-on-one with their manager, the buddy would send them a quick guide on how to prepare.
- Culture Coaching: The buddy would also act as a culture coach, helping new hires understand our async communication norms, our decision-making processes, and our company values. It would even give them gentle nudges if they were violating our cultural norms, like sending a direct message to someone who was in a different time zone and likely asleep.
Building this AI onboarding buddy was a huge investment, but it paid off in spades. It not only improved our onboarding process, but it also reinforced our remote-first culture in a very tangible way.
The Future is Async, and It's Powered by AI
As I look to the future, I'm more convinced than ever that asynchronous work is the future of work. And AI will be the engine that powers it. The clunky, real-time tools of today will be replaced by intelligent, async-first platforms that will help us work smarter, not harder.
Imagine a world where you can go on vacation for a week and come back to a personalized summary of everything you missed, with clear action items and recommendations. Imagine a world where you can have a productive, collaborative meeting without ever having to be in the same room at the same time. Imagine a world where you can focus on your work without being constantly interrupted by notifications and distractions. This is the future that AI coworking will make possible.
I'm not saying that real-time communication will go away entirely. There will always be a place for face-to-face meetings and spontaneous conversations. But the default will be async. And that will be a game-changer for productivity, for well-being, and for the future of work itself.
I've bet my career on it. And I'm more excited than ever to see what we can build together.
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.
Do all experts agree with this view?
No, and that's fine. The best ideas in business are often contrarian. I share my perspective based on my experience and data, but I encourage you to seek out opposing viewpoints and form your own conclusions.
How has this view evolved over time?
My thinking on most topics has changed significantly over the years. Early in my career, I held many conventional views that experience proved wrong. I try to update my beliefs when the evidence changes.