What if I told you the key to unlocking massive productivity with AI coworking was actually doing less? It sounds crazy, but the results speak for themselves.
For years, I chased the AI dream. I built RemoteTeam, which was acquired by Gusto, on the bleeding edge of remote collaboration. I’ve invested in over 200 companies, including AI giants like Anthropic, OpenAI, and Scale AI. I’ve seen it all, from the inside and the outside. And I can tell you, most people are doing AI wrong.
They treat it like a tool. A better, faster intern. They throw tasks at it, hoping to get more done. But that’s like using a fighter jet to deliver a pizza. You’re missing the point.
AI isn’t a tool. It’s a coworker. A weird, brilliant, sometimes frustrating coworker who thinks in a completely different way. And learning to work with it, not just use it, is the biggest unlock of the next decade. After years of trial and error, I finally cracked the code. Here are the raw, unfiltered lessons I learned the hard way.
1. Your Goal is to be Lazy (the Smart Way)
I used to be a workaholic. 100-hour weeks were my baseline. I thought the more I did, the more I’d achieve. Then I started working with AI. And I realized my goal wasn’t to do more, but to do less. Much less.
My first real AI coworker was a clunky script I wrote back in the early days of MovieLaLa. It was supposed to automate some basic data entry. It was terrible. It broke constantly. But it taught me a valuable lesson: my job wasn’t to do the work, but to build the system that does the work. My job was to be the lazy one.
Today, my AI coworkers are a lot more sophisticated. I have an AI assistant that manages my calendar, drafts my emails, and even does my initial research for angel investments. I spend maybe an hour a day giving it direction. The rest of the time? I’m thinking. I’m strategizing. I’m talking to founders. I’m doing the things only a human can do.
Your goal with AI coworking isn’t to get more done. It’s to free yourself up to do the work that actually matters.
2. Stop Giving Orders, Start Asking Questions
Most people talk to AI like it’s a command-line interface. “Write me a blog post about X.” “Summarize this article.” “Generate a logo for my startup.”
You’ll get a result. It will probably be mediocre. Because you’re treating your AI coworker like a vending machine.
The real magic happens when you start asking questions. “What are some surprising angles for a blog post about X?” “What’s the most controversial point in this article?” “What are some visual metaphors for my startup’s mission?”
When you ask questions, you’re not just getting an answer. You’re starting a conversation. You’re inviting your AI coworker to think, to create, to surprise you. I’ve had some of my best investment ideas come from these kinds of open-ended conversations with AI.
3. Embrace the Weirdness
AI doesn’t think like a human. It makes strange connections. It comes up with bizarre ideas. It hallucinates. And that’s its superpower.
I was recently working with an AI on a marketing campaign for one of my portfolio companies. I asked it for some ideas. One of them was to create a series of silent films about the product. It was a completely insane idea. It had nothing to do with the product. But it was also brilliant.
We didn’t end up making silent films. But the idea sparked a whole new direction for the campaign. It got us out of our rut. It forced us to think differently.
Don’t be afraid of the weirdness. Lean into it. The most interesting ideas are often the ones that make no sense at first.
4. Your AI Coworker Needs a Vacation (Sort of)
I used to think of AI as a tireless machine. It doesn’t need to sleep. It doesn’t get tired. It can work 24/7. But I was wrong.
AI models can get “stuck.” They can get into a rut, generating the same kinds of ideas over and over. They can overfit to your style, losing their own unique perspective.
I’ve learned to give my AI coworkers a “vacation.” I’ll switch to a different model for a few days. I’ll give it a completely different kind of task. I’ll even “talk” to it about something completely unrelated to work.
It sounds crazy, but it works. When I come back to my primary AI coworker, it’s often “refreshed” and ready to generate new ideas.
5. The Best AI Coworkers are the Ones You Build Yourself
You can get a lot done with off-the-shelf AI tools like ChatGPT or Claude. But the real competitive advantage comes from building your own AI coworkers.
I’m not talking about building your own large language models from scratch. I’m talking about fine-tuning existing models on your own data. Your emails. Your documents. Your conversations.
I have an AI coworker that’s fine-tuned on every email I’ve ever sent. It knows my voice. It knows my network. It can draft emails for me that are indistinguishable from my own.
Building your own AI coworkers is the ultimate moat. It’s a competitive advantage that no one can copy.
6. Your Job is to be the Editor, Not the Writer
I used to spend hours writing and rewriting every word of every blog post, every investor update, every tweet. Now, I let my AI coworkers do the first draft. And the second. And the third.
My job is to be the editor. I guide the process. I provide feedback. I shape the final product. But I don’t do the heavy lifting.
This is a huge mindset shift for most people. They’re used to being the one in the driver’s seat. But with AI coworking, you’re the navigator. You’re setting the destination, but you’re letting the AI do the driving.
7. The Most Important Skill is Prompt Engineering
If you want to be a great AI coworker, you need to be a great prompt engineer. Prompt engineering is the art and science of crafting the perfect input to get the desired output from an AI.
It’s not just about asking the right questions. It’s about providing the right context. It’s about setting the right constraints. It’s about understanding how the AI “thinks” and what it needs to do its best work.
I’ve spent hundreds of hours learning how to write better prompts. It’s the highest-leverage skill I’ve learned in the past five years.
8. AI Coworking is a Team Sport
You can get a lot done with a single AI coworker. But the real magic happens when you start building a team of AI coworkers.
I have a team of AI coworkers that I use for different tasks. I have a “researcher” AI that’s great at finding and summarizing information. I have a “writer” AI that’s great at generating long-form content. I have a “creative” AI that’s great at brainstorming new ideas.
I’ll often have them work together on a project. The researcher will find the data, the writer will draft the article, and the creative will come up with the headline and the images.
Building a team of AI coworkers is like building a team of human employees. You need to find the right talent, give them the right roles, and get them to work together effectively.
9. The Goal Isn’t to be Perfect, It’s to be Interesting
AI can generate perfect, grammatically correct, SEO-optimized content. But it’s often boring. It lacks a soul. It doesn’t have a point of view.
Your job as an AI coworker isn’t to be perfect. It’s to be interesting. It’s to have a unique voice. It’s to say something that no one else is saying.
Don’t be afraid to be controversial. Don’t be afraid to be vulnerable. Don’t be afraid to be human.
The best content is the content that makes you think, that makes you feel, that makes you see the world in a new way. And that’s something that no AI can do on its own.
The Future is a Conversation
The future of work isn’t about humans versus machines. It’s about humans and machines working together. It’s a conversation. A collaboration. A partnership.
The sooner you embrace this new reality, the sooner you’ll be able to unlock the massive potential of AI coworking. So stop giving orders and start asking questions. Stop trying to be perfect and start trying to be interesting. And most importantly, stop doing the work and start building the system.
The lazy way is the smart way. And it’s the only way to win in the age of AI.
Frequently Asked Questions
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.
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.
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.
Can I implement all of these at once?
I'd strongly recommend against it. Pick the 2-3 items that resonate most with your current situation and focus there. Trying to do everything simultaneously is a recipe for doing nothing well.