I’m about to say something that will make a lot of people in Silicon Valley mad. Good.
They’re wrong about AI coworking. Dead wrong.
For the past few years, I’ve been on a deep dive into how AI is actually being used in the workplace. Not the fluff you see on tech blogs, but the real, in-the-trenches stuff. I’ve seen it as an investor in over 200 companies, including some of the biggest names in AI like Anthropic, OpenAI, Scale AI, and Hugging Face. I’ve seen it as a founder who has built and sold two companies, RemoteTeam and MovieLaLa. And I’ve seen it as an author who has talked to thousands of people about what it takes to get to the top 1%.
And what I’ve learned is that most of what you’re being told about AI coworking is a lie.
It’s not about finding the perfect prompt. It’s not about having the fanciest new AI tool. And it’s definitely not about replacing your human coworkers with a bunch of bots.
The truth is much more counterintuitive. It’s about understanding the fundamental nature of AI and how it interacts with human psychology. It’s about building a culture of experimentation and learning. And it’s about being willing to throw out the old rules and write new ones.
So, if you’re ready to forget everything you’ve read about AI coworking and learn the secrets that will actually make a difference, then this article is for you. Here are the five counterintuitive lessons I’ve learned about AI coworking.
Lesson 1: Your AI Coworker is Not Your Friend
This is the biggest mistake I see people making. They treat their AI coworkers like they’re human. They try to be polite. They try to build a rapport. They even give them names.
But here’s the thing: your AI coworker is not your friend. It’s a tool. A very powerful tool, but a tool nonetheless. And the sooner you start treating it like one, the sooner you’ll be able to unlock its full potential.
Think about it this way: you wouldn’t try to be friends with your hammer, would you? You wouldn’t ask it how its day was going. You wouldn’t try to make small talk. You’d just pick it up and use it to do what you need to do.
It’s the same with AI. You need to be direct. You need to be specific. And you need to be willing to experiment. Don’t be afraid to give it a command that you think is too simple or too complex. Don’t be afraid to push it to its limits. And don’t be afraid to start over if you don’t get the results you want.
I remember when I was first starting to use AI in my own work, I would spend hours trying to craft the perfect prompt. I would try to be clever. I would try to be witty. And I would get frustrated when the AI didn’t understand what I was trying to say.
But then I had a realization: I was thinking about it all wrong. I was treating the AI like a person, when I should have been treating it like a machine. So I started being more direct. I started using simpler language. And I started breaking down my requests into smaller, more manageable steps.
And you know what? It worked. The AI started giving me better results. And I started getting more done in less time.
So, the next time you’re working with an AI, remember: it’s not your friend. It’s a tool. Treat it like one, and you’ll be amazed at what you can accomplish.
Lesson 2: Stop Obsessing Over Prompting
This is another huge time-waster I see. People spend hours and hours trying to come up with the perfect prompt. They read blog posts. They watch videos. They even take courses on how to become a “prompt engineer.”
But here’s the secret: prompting is not the most important part of working with AI. Not even close.
The most important part is what you do after you get the initial output. It’s about how you refine it, how you edit it, and how you combine it with your own knowledge and expertise.
Think of the AI as a very smart, very fast, but very inexperienced intern. It can do a lot of the heavy lifting for you. It can do research. It can generate ideas. It can even write first drafts. But it’s not going to give you a finished product. It’s up to you to take what it gives you and turn it into something great.
I’ve seen this time and time again in my own work. I’ll use an AI to generate a first draft of a blog post or a marketing email. And the first draft is usually pretty good. But it’s never perfect. It’s always missing something. It’s always missing my voice, my personality, my unique perspective.
So, I’ll take that first draft and I’ll start to edit it. I’ll add my own stories. I’ll add my own examples. I’ll add my own opinions. And by the time I’m done, the final product is something that is uniquely mine. It’s something that the AI could have never created on its own.
So, don’t get bogged down in the quest for the perfect prompt. Instead, focus on what really matters: your own creativity, your own expertise, and your own unique voice. That’s what will separate you from the competition. And that’s what will make you a true master of AI coworking.
Lesson 3: The Real Moat is Your Company's Data
Everyone is so focused on the models themselves. Which one is bigger? Which one is faster? Which one is more creative? But they’re missing the point.
The models are becoming a commodity. They’re getting cheaper and more accessible every day. And soon, everyone will have access to the same powerful AI tools.
So, what will be the new competitive advantage? What will be the new moat that separates the winners from the losers?
It’s your data. Your company’s unique, proprietary data. That’s the one thing that your competitors can’t copy. That’s the one thing that will give you a sustainable edge.
I saw this firsthand when I was building RemoteTeam. We were a platform that helped companies manage their remote teams. And we had a ton of data on how remote teams work. We knew what made them successful. We knew what made them fail. And we used that data to build a better product.
Our competitors could have copied our features. They could have copied our marketing. But they couldn’t copy our data. And that’s what ultimately made us successful. That’s what led to our acquisition by Gusto.
So, if you’re not already thinking about how to collect, analyze, and use your company’s data, you’re already behind. You need to be building a data-driven culture. You need to be investing in data infrastructure. And you need to be empowering your employees to use data to make better decisions.
Because in the age of AI, data is not just the new oil. It’s the new everything.
Lesson 4: AI Won't Kill Your Culture, Your Terrible Policies Will
There’s a lot of fear out there that AI is going to destroy company culture. That it’s going to turn us all into a bunch of isolated, antisocial robots.
But that’s just not true. AI is not the enemy of culture. Bad management is.
I’ve seen companies with amazing cultures that use AI extensively. And I’ve seen companies with terrible cultures that don’t use AI at all. The difference is not the technology. It’s the leadership.
If you have a culture of trust, transparency, and collaboration, then AI will only make it stronger. It will free up your employees from the mundane, repetitive tasks that they hate, and it will give them more time to focus on the creative, strategic work that they love. It will give them new tools to collaborate and communicate with each other. And it will give them new opportunities to learn and grow.
But if you have a culture of fear, secrecy, and micromanagement, then AI will only make it worse. It will become just another tool for surveillance and control. It will be used to track your employees’ every move. It will be used to automate them out of a job. And it will be used to create a work environment that is even more toxic and soul-crushing than it already is.
So, don’t blame AI for your culture problems. Look in the mirror. Look at your own policies. Look at your own leadership style. And ask yourself: am I building a culture that is worthy of the amazing potential of AI?
Lesson 5: The "Digital Nomad AI" Dream is a Mirage (For Most)
I’m a big believer in remote work. I built a whole company around it. And I think that the freedom and flexibility that it offers can be life-changing.
But I’m also a realist. And the reality is that the “digital nomad AI” dream is not for everyone. It’s not even for most people.
Yes, there are some people who can travel the world with nothing but a laptop and an AI assistant. But those people are the exception, not the rule. They are the outliers. They are the 1%.
For the vast majority of people, the future of work is not going to be fully remote. It’s going to be hybrid. It’s going to be a mix of in-office and remote work. And that’s a good thing.
Because the truth is, there are some things that are just better done in person. There’s a certain energy that you can only get when you’re in a room with other people. There’s a certain kind of collaboration that can only happen when you’re whiteboarding ideas together. And there’s a certain kind of relationship-building that can only happen when you’re grabbing a coffee or a beer after work.
AI can help with some of these things. It can make it easier to collaborate with people in different time zones. It can help you stay connected with your team when you’re not in the same room. But it can’t replace the human element entirely.
So, don’t get seduced by the fantasy of the digital nomad AI lifestyle. It’s a beautiful dream, but for most of us, it’s just that: a dream. The reality of the future of work is going to be a lot more messy, a lot more complicated, and a lot more human.
And that’s something to be excited about.
The Real Revolution is Just Getting Started
We’re at the very beginning of the AI revolution. And the truth is, nobody knows exactly where it’s going to take us. But one thing is for sure: it’s going to be a wild ride.
There will be ups and downs. There will be successes and failures. And there will be a lot of people who get left behind.
But if you’re willing to be counterintuitive, if you’re willing to challenge the conventional wisdom, and if you’re willing to embrace the chaos, then you have a chance to be one of the ones who comes out on top.
You have a chance to be one of the ones who builds the future.
So, what are you waiting for?
Frequently Asked Questions
How do I know which items apply to my situation?
Start by honestly assessing where your biggest bottleneck is right now. The items that address that specific constraint will give you the highest return on your time and energy.
How were these items selected?
Each item on this list comes from direct experience, either from building my own companies or from patterns I've observed across the 200+ startups I've invested in. I prioritize practical, actionable items over theoretical concepts.
Which item on this list has the highest impact?
It depends on your stage and context, but in my experience, the items near the top of the list tend to have the broadest applicability. That said, sometimes the less obvious items create the biggest breakthroughs for specific situations.