I used to think being busy was the same as being productive. For a decade, my calendar was a relentless wall of back-to-back meetings. I’d spend hours each day just preparing for them, and even more time afterward trying to remember what was said, what was promised, and what I was supposed to do next. My notes were a chaotic mess of Google Docs, Apple Notes, and random scraps of paper. I was drowning in a sea of my own disorganization.
It all came to a head in 2022. I was running RemoteTeam, my second startup, and I was also an active angel investor in over 100 companies. One week, I had 37 meetings. I remember sitting at my desk on a Friday night, staring at a half-written email to an investor, and I just couldn't remember the key metric I was supposed to include. I’d spent an hour in that meeting, and the most important takeaway had vanished from my brain. I was working 80-hour weeks, but I felt like I was running in place. That was my breaking point. I realized I wasn't just busy; I was a bottleneck. My own inability to manage information was holding back my company and my investments.
The All-In AI Experiment
I’m a builder at heart. When I see a problem, I want to build a solution. So, I decided to go all-in on AI. I wanted to see if I could build a “personal OS” that would automate the tedious, low-value tasks that were consuming my life. My goal was to free up my mind to focus on what actually matters: building products, mentoring founders, and spotting the next big thing.
Some of my early experiments were a complete disaster. I tried using an early AI transcription service that turned a critical board meeting into what looked like a surrealist poem. It confidently transcribed “increase our user retention” as “increase our goose prevention.” We all had a good laugh, but it was a reminder that AI wasn't a magic bullet. You can't just plug it in and expect it to work.
But I kept experimenting. I tried dozens of tools. I built my own scripts. I treated it like an engineering problem: hypothesis, experiment, iterate. And slowly, I started to find things that worked. Life-changing things.
My AI-Powered Personal OS: The Playbook
This isn't a theoretical guide. This is my actual playbook. These are the tools and workflows I use every single day to manage my life as a founder and investor.
1. The AI Meeting Assistant: My Second Brain
This was the first and most important problem I had to solve. I needed a way to capture everything that was said in a meeting, without having to type a single word. After trying and discarding a dozen tools, I landed on a combination that works for me.
- The Tool: I use a dedicated AI meeting assistant that joins all my Zoom and Google Meet calls. It records, transcribes, and summarizes every meeting.
- The Workflow:
- Before the meeting: I don't do anything. The assistant automatically joins my calendar invites.
- During the meeting: I focus 100% on the conversation. I'm not typing, I'm not distracted. I'm fully present.
- After the meeting: Within minutes, I get a full transcript, a summary, and a list of action items in my inbox. The summary is the key. It’s not just a block of text; it’s a structured overview of the conversation, with key topics and decisions highlighted.
What Worked: The biggest win here is the ability to be fully present in meetings. I can focus on the person I'm talking to, not on my keyboard. The searchable archive of all my conversations is a close second. I can instantly find any detail from any meeting I've had in the last two years.
What Didn't: Don't trust the action items blindly. The AI is good, but it's not perfect. I still spend 5 minutes reviewing the summary and cleaning up the action items. But 5 minutes is a lot better than the hour I used to spend.
2. The AI Email Manager: Taming the Inbox
My inbox is a constant firehose of requests, updates, and introductions. I get hundreds of emails a day. For years, I was a slave to my inbox. Now, AI helps me manage it.
- The Tool: I use an AI email client that integrates directly into my Gmail.
- The Workflow:
- Triage: The AI automatically categorizes my emails. Newsletters, notifications, and other low-priority messages are moved to a separate folder. My main inbox is reserved for emails that are from people I know or that the AI has identified as important.
- Drafting: I rarely write an email from scratch anymore. I’ll write a few bullet points, and the AI will draft a full reply. It’s not always perfect, but it’s a huge time-saver. I can edit the draft to get the tone just right.
- Summarization: For long email threads, the AI gives me a one-paragraph summary. This is a lifesaver when I'm added to a thread that's already 20 messages deep.
What Worked: The automatic triage is the biggest win. It's like having a personal assistant who sorts your mail for you. I spend less than an hour a day on email now, down from 3-4 hours.
What Didn't: The AI can sometimes be too formal. I've had to train it to write in my voice. It's a process. You have to give it feedback and examples.
3. The AI Scheduler: Never Play Calendar Tetris Again
Scheduling is one of the most tedious parts of my job. The back-and-forth of finding a time that works for everyone is a massive waste of time. AI has completely eliminated this for me.
- The Tool: I use an AI scheduling assistant that handles all my meeting requests.
- The Workflow:
- The Request: When someone wants to meet with me, I just CC my AI assistant. I’ll say something like, “AI, please find a 30-minute slot for me and John next week.”
- The Magic: The AI then takes over. It emails John, offers him a few times based on my calendar availability, and sends out the calendar invite once a time is confirmed. I don't see any of the back-and-forth.
What Worked: This is the closest thing to real magic I've found in AI. It's completely automated. I haven't personally scheduled a meeting in over a year.
What Didn't: You have to be very clear with your instructions. If you say “next week,” the AI will offer times from Monday to Friday. If you only want to meet on Tuesday, you have to say that. You also need to make sure your calendar is always up-to-date. The AI can only work with the information it has.
The Real Value of an AI-Powered Life
These tools have given me back at least 20 hours a week. But the real value isn't just the time I've saved. It's the mental space that's been freed up. I'm no longer constantly stressed about missing a detail or dropping a ball. I can think more clearly. I can focus on the big picture. I'm a better founder and a better investor because of it.
Building your own personal OS takes time. It's not something you can do overnight. But it's one of the highest-leverage investments you can make in yourself. Stop being busy and start being productive. The robots are here to help.
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.
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.