I’ve sold two companies and invested in over 200 startups. You’d think I’d have my schedule figured out. For a long time, I really didn’t. I was just busy, not productive, drowning in a sea of tasks and meetings. I burned out. That’s when I went all-in on AI, not just as an investor, but as a user. This is the story of how I built my own AI-powered personal OS.
The Breaking Point: Calendar Chaos
I remember one week where everything broke. I was fundraising for my startup, RemoteTeam, and a critical follow-up with a potential lead investor was scheduled by a human assistant in the wrong time zone. I missed it. The investor passed. That one mistake cost us. It was a painful lesson that my manual system was a house of cards.
My first attempts with AI were a joke. I tried an early AI assistant that scheduled a demo with a potential customer at 3 AM. Another time, a transcription tool garbled the notes from a board meeting so badly they were useless. I learned you can't just plug in AI and expect magic. You have to build a system.
My AI Scheduling Playbook
After a lot of trial and error, I’ve built a set of tools that run my life. It’s not one app, it’s an integrated system.
The Smart Scheduler
This is the core of my system. I use a smart scheduler that does more than just book meetings. It blocks out a four-hour chunk for deep work every morning. My AI knows this time is sacred. No meetings get through unless the request is from a small, pre-approved VIP list. It also groups smaller meetings together to stop me from constantly switching gears.
The AI Meeting Assistant
I live in back-to-back meetings. I can’t remember every single action item. I use Fireflies.ai to record and transcribe my calls. The best part is the summary and action item detection. After a day of pitches, I get a to-do list. Every time someone says “I’ll send you the deck,” the AI captures it. It’s like having an assistant in every conversation.
The Email Butler
My inbox is a firehose. I use an AI email client that sorts my emails into ‘Urgent,’ ‘Investment Opportunity,’ and ‘Read Later.’ It even drafts replies. I get a lot of cold emails from founders. My AI can now identify these, see if they fit my investment thesis, and draft a polite rejection or a request for more info. It saves me at least an hour a day.
Build Your Own AI-Powered OS
This isn't as complicated as it sounds. Here’s how you can start:
1. Audit Your Time. For one week, track everything. Where does your time actually go? Be honest.
2. Find the Bottlenecks. Where are the biggest drains? Scheduling? Email? Note-taking? Find the one or two things that are causing the most pain.
3. Start with one tool. Don’t try to do everything at once. Pick one bottleneck and find the best AI tool for it. Master it.
4. Integrate. Make your tools talk to each other. Use Zapier or Make to create workflows. For example, an action item from your meeting assistant can automatically create a task in your project manager and block out time in your calendar.
5. Review and Refine. This system isn't static. Every quarter, review it. What’s working? What’s not? Be ruthless. Cut what isn’t adding value.
The Future is Scheduled
My AI-powered OS has genuinely changed my life. I’m more productive and less stressed.
Here’s my prediction: by 2027, if you're a founder or executive and you're not using an AI scheduling system, you are choosing to be at a disadvantage. The best opportunities won't wait for you to find a slot in your calendar. The people who embrace this will be the ones who lead.
What’s the one repetitive task you could give to an AI tomorrow? Start there.
Frequently Asked Questions
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.
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.
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.