I fired my personal assistant.
There, I said it. After years of relying on a human to manage my calendar, inbox, and life, I handed all of it over to an AI. And not some custom-built, multi-million dollar system from a sci-fi movie. I’m talking about a few off-the-shelf tools that cost less than my weekly coffee budget.
Everyone in Silicon Valley is obsessed with complex, enterprise-grade AI solutions. They’re building these incredible, complicated systems to automate every corner of their business. And they’re mostly wrong. The real secret to getting your life back isn’t another complex system; it’s about letting a few simple AI tools do the heavy lifting in a way nobody talks about.
For years, I was stuck in the same loop as every other founder and investor. My day was a relentless firehose of emails, meeting requests, and follow-ups. I hired a fantastic personal assistant—smart, dedicated, and incredibly patient. But they were human. They needed to sleep. They took vacations. And honestly, managing my manager was becoming a job in itself. Every morning started with a 30-minute sync to align on priorities. That’s 2.5 hours a week, just to get on the same page.
It felt inefficient. I’ve built my career on finding leverage, from scaling RemoteTeam before the Gusto acquisition to making over 200 angel investments in companies like Anthropic and OpenAI. I look for the 10x return, the asymmetric bet. And I realized the way I was managing my own time was a 1x activity. It was linear. I was the bottleneck.
The Experiment: Handing Over the Keys
My thesis was simple: 80% of my assistant's work was repetitive, pattern-based, and ripe for automation. Could I replace that 80% with AI? I was skeptical. I’d been burned by so-called “AI assistants” before that were little more than glorified chatbots.
But I decided to try. I gave myself one month. The goal wasn't just to survive, but to see if I could actually get more done, with less stress. I picked a few simple tools, connected them, and held my breath.
The results weren't just good. They were shocking. I didn’t just save the 2.5 hours a week on syncs. I saved at least 10-15 hours on top of that. My inbox, once a source of constant anxiety, became a tool I controlled. My calendar, once a chaotic mess of overlapping holds, became a strategic asset.
Here’s the exact stack I used, and how I use it.
My AI Personal Assistant Stack
This isn't about a single, magical app. It's about a workflow, a system of simple tools that work together.
1. The Inbox Zero Machine (Superhuman)
My email is the front door to my professional life. It’s where deals start, where founders ask for advice, and where most of my administrative drag comes from. Superhuman, with its AI layer, became my first line of defense.
- AI Triage: The first thing I did was let its AI automatically sort my inbox. It learned who was important and what was just noise. Pitches from VCs I know? Front and center. Cold outreach from a sales rep? Archived. Within a week, my inbox was 90% signal, 10% noise, down from about 50/50.
- One-Click Drafts: For common replies—like my polite “no” to a startup I’m not investing in, or a request for a deck—I use AI-generated snippets. I don’t have to think. I hit a keyboard shortcut, the AI drafts a personalized reply based on the context, I give it a quick scan, and it’s sent. This alone saves me an hour a day.
2. The Autopilot for Meetings (Read AI & Motion)
Meetings are the second biggest time sink. Not just the meeting itself, but the prep and the follow-up. My AI stack turned this into a fully automated process.
- Automated Scribe (Read AI): I have Read AI join every single one of my Zoom calls. It’s my silent partner taking perfect notes. It transcribes the entire conversation, identifies who said what, and—this is the magic part—automatically generates a summary with key decisions and action items. My old workflow was my assistant frantically typing, then spending 30 minutes after the call cleaning up the notes. Now, it’s done before I’ve even closed the Zoom window.
- Intelligent Calendar (Motion): Scheduling is a nightmare. The back-and-forth of “Does Tuesday at 2 PM work?” is a soul-crushing waste of time. Motion handles all of it. I send a booking link, and it intelligently finds a time that works for both parties based on my real-time availability and priorities. It even automatically generates a Zoom link and a calendar invite. It’s like having a scheduler who has a live feed of my brain.
3. The Central Nervous System (Zapier)
This is the glue that holds everything together. Zapier is the digital plumbing that connects all my apps and lets me build simple “if this, then that” automations without writing a single line of code.
Here are a few of my favorite “Zaps”:
- Action Item to Todoist: When Read AI generates meeting notes, Zapier automatically scans for action items assigned to me and creates a task in my to-do list app, Todoist, with a due date and a link back to the meeting notes.
- Investor Update to CRM: When I get an investor update email from one of my portfolio companies, Zapier automatically parses it and logs the key metrics in a simple Airtable base I use as a personal CRM.
- Interesting Article to Read-Later: If I star an email in Superhuman that contains a link to an article, Zapier sends it directly to my Pocket queue to read later.
None of these tools are revolutionary on their own. But together, they form a system that is far more powerful and efficient than a human assistant for 80% of the tasks.
The Real Results: More Than Just Time
The extra 15 hours a week was the obvious win. That’s nearly two full workdays back in my pocket. That’s more time to meet with founders, do deep thinking, and frankly, have a life. I closed three extra angel investments the first month because I had the bandwidth to properly evaluate them.
But the real change was mental. The cognitive load of managing a thousand tiny, open loops was gone. I no longer had that nagging feeling that I was forgetting something. The system was handling it. I could focus on the 20% of my job that actually creates value: building relationships, making hard decisions, and thinking about the future.
I’m not saying human assistants are obsolete. For that last 20%—the complex, high-touch, relationship-based tasks—a great human is still unbeatable. But we’re using them wrong. We’re using smart, capable people as human routers. It’s a waste of their talent and our money.
Stop listening to the gurus selling you on another complex piece of software. The secret to insane productivity isn't a new system. It's ruthless simplification. It’s about having the courage to let go and trust a few simple, powerful AI tools to do the heavy lifting.
My assistant is an AI now. And I’ve never been more productive.
Frequently Asked Questions
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.
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.
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.