I once tracked every single minute of my day for three months straight. I logged everything—meetings, calls, writing code, family time, even bathroom breaks. I’m a data guy, and I figured the data would show me the path to peak productivity. The results were just depressing.
The data told me I was spending roughly 10 hours a week—a full workday—just managing my schedule. That’s 520 hours a year. Over the 9 years since my first exit, that’s nearly 5,000 hours. Thousands of hours spent on the soul-crushing back-and-forth of “Does Tuesday at 2 work for you?” or trying to find a 30-minute slot for a pitch that I knew probably wasn’t a fit in the first place.
It was a death by a thousand paper cuts. A missed follow-up with a promising founder. A double-booking that made me look unprofessional. The constant, low-grade anxiety of my calendar feeling less like a tool for success and more like a leaky boat I was constantly bailing out.
After my second exit, when RemoteTeam was acquired by Gusto, I was burned out. I had built companies, invested in over 200 more—including some you’ve definitely heard of like Anthropic and OpenAI—and written a book on how to be in the top 1%. Yet, my own time was being dictated by the chaos of my inbox. I decided to go all-in on fixing it. I decided to treat my life like a product and build myself a new operating system, powered by AI.
Some of my experiments were a complete disaster. But some of them were life-changing. This is my playbook.
The Old Way: Calendly Can't Save You
For years, I thought technology was the answer. I used Calendly. I used x.ai before it was acquired. I had virtual assistants. These tools are fine, but they only solve a tiny piece of the problem. They show people your availability, but they don’t provide any real intelligence. They’re like a digital secretary who can only read a calendar but has no context about what actually matters.
My calendar was still a mess of low-value meetings. I’d get a Calendly booking from someone I didn’t know, for a company in a market I don’t invest in, and I’d have to spend time researching them, politely declining, and dealing with the follow-up. It was still reactive. My time was still being hijacked by other people’s priorities.
I remember one specific week in 2022. I was juggling due diligence on a Series A investment, helping a portfolio founder navigate a crisis, and trying to prep for a board meeting. My calendar was so packed with pre-booked, low-value calls that I ended up on a call with a founder pitching a new brand of cat food. I love cats, but I don’t invest in CPG. It was a waste of his time and a complete waste of mine. That was the breaking point.
Building a Personal OS: The AI Experiments
I decided to build a system that wasn’t just about booking meetings, but about qualifying and prioritizing them. A system that would act as an intelligent gatekeeper for my time. I’m an engineer at heart, so I started tinkering.
My first few attempts were comical failures. I tried to hook up an early GPT-3 model to my email to auto-respond to meeting requests. It once told a top-tier VC that I was “currently contemplating the futility of existence” and would get back to them when I had “achieved a state of oneness with the universe.” He thought it was hilarious, thank God. Another time, it tried to schedule a meeting for 3:00 AM Pacific Time. Not ideal.
But through trial and error, I landed on a system that works. It’s not one tool; it’s a workflow, a personal OS built from a few key components.
1. The Intelligent Triage Bot
This was the real breakthrough. Instead of sending a Calendly link, I now have an AI assistant handle the initial intake. When someone emails me for a meeting, they get a polite, automated response that asks them to fill out a short form. It’s not a long, annoying form. It’s just a few questions:
- What’s the purpose of the meeting?
- What’s the name of your company/project?
- Please provide a one-sentence summary.
- Link to your deck/website.
The magic happens next. The form submission triggers a workflow that uses an AI model to analyze the response. It checks the startup against my investment thesis—is it in a sector I care about? Is it at the right stage? It even does a quick sentiment analysis of their summary. Based on this analysis, it assigns a priority score from 1 to 5.
- P1 (Urgent): My portfolio founders, key investors, or a startup that is a perfect 10/10 fit. My AI has access to my calendar and automatically proposes times.
- P2 (High Priority): A great-fit startup or an interesting introduction. The AI will ask for their availability and then coordinate with my calendar.
- P3 (Maybe): An interesting but not perfect fit. The AI will politely ask for more information or suggest they send a deck for me to review asynchronously.
- P4/P5 (Low Priority/No Fit): The AI sends a polite, personalized decline. It might even suggest another investor I know who is a better fit. This way, I’m still being helpful, but I’m not spending any time on it.
This single system eliminated about 80% of the noise from my inbox and calendar.
2. AI for Meeting Prep and Notes
I never go into a meeting blind anymore. Before any scheduled call, my OS automatically creates a briefing document for me. It pulls information from the intake form, scrapes the company’s website, finds the founder’s LinkedIn profile, and looks for any recent news or funding announcements. It’s all there in a one-page summary.
During the meeting, I have an AI transcriber running in the background. I use a tool that not only gives me a full transcript but also automatically generates a summary, identifies key decisions, and lists out all the action items.
This is huge. I used to spend 30-60 minutes after a day of meetings just processing my notes and sending follow-ups. Now, it’s all done for me. The AI drafts the follow-up email with the action items, and all I have to do is review it and hit send. This alone saved me 3-4 hours a week.
3. The Asynchronous Default
My biggest realization was that most meetings don’t need to be meetings at all. My new OS aggressively pushes for asynchronous communication. If a founder wants to give me a quick update, the AI will suggest they record a short Loom video instead of booking a 30-minute call. If someone wants to “pick my brain,” the AI will ask them to send their questions in an email, and I can respond when I have a free moment.
This isn’t about being rude or avoiding people. It’s about respecting everyone’s time. A 5-minute Loom video is more efficient than a 30-minute call that’s 20 minutes of small talk. This shift in mindset, enforced by my AI system, has been the single biggest factor in getting my time back.
The Result: From Burnout to Deep Work
So what happened after I implemented this system? That 10 hours a week of wasted time is now down to about 30 minutes. The thousands of hours I was losing are now mine again. I use that time for deep work—analyzing deals, writing, and actually helping my portfolio companies. My deal flow is higher quality, my decision-making is faster, and I’m less stressed.
My calendar is no longer a source of anxiety. It’s a tool that reflects my priorities. I’m not just managing my time anymore; I’m designing it.
If you’re a founder, an investor, or anyone who feels like their calendar is out of control, I’m telling you, there’s a better way. Stop just using tools. Start building a system. You don’t need to be a programmer to do it. With today’s AI platforms, you can connect these workflows with a few clicks.
Start with one thing. Automate your meeting notes. Set up an intelligent email filter. Stop sending Calendly links and create an intake form. If you’re not using AI to build your own personal OS, you’re not just falling behind. You’re actively choosing to waste your most valuable asset: your time.
Frequently Asked Questions
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 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.
What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.