Let’s be real for a second. I almost missed out on what became a 50x return on an investment because my “smart” AI email assistant decided the founder’s pitch wasn’t a priority. It didn’t have exclamation points or fit the pattern of my typical deal flow, so it got buried in a folder I never check. I only found it by accident weeks later while searching for something else. I got lucky. But it was a wake-up call.
We’re all drowning in information. As a founder who’s been through two exits and now as an angel investor in over 200 companies, my inbox is a firehose. My calendar is a battlefield. So when AI productivity tools exploded onto the scene, I was first in line. The promise was seductive: an AI that could manage my email, summarize my meetings, and basically run my life so I could focus on the “real work.”
It was a complete failure.
For months, I felt like I was just spinning my wheels. I had this nagging feeling of being busy but not productive. It turns out, the very tools that promised to save me were actually making me less effective. Most people are using these AI assistants completely wrong, and it’s quietly killing their productivity. The secret to insane productivity isn't another complex system; it's about letting AI do the heavy lifting in a way nobody talks about.
The Great AI Productivity Trap
The biggest problem is what I call the “Illusion of Done.” Your AI assistant sorts 100 emails into neat little folders and presents you with five summaries. You feel great. Look at all that work you cleared! But you haven’t actually done anything. You haven’t made a decision, replied to a critical question, or built a relationship. You’ve just kicked the can down the road. The real cognitive load—the thinking—is still waiting for you.
Worse, these tools often become “busywork multipliers.” That near-miss on the 50x investment is a perfect example. The AI misjudged the email’s importance, creating a huge risk. I’ve seen it happen with my own companies. At RemoteTeam, we had an AI assistant try to summarize a complex customer feedback thread. It completely missed the nuance, reported the customer as “happy,” when in reality they were flagging a critical bug that was about to impact our entire user base. The AI’s mistake cost us a week of engineering time to fix a problem that we could have caught instantly.
Every time you have to double-check the AI’s work or correct its summary, you’re engaging in a massive context switch. You’re pulled out of deep work on a pitch deck or a product roadmap to babysit your assistant. This isn’t productivity. It’s a tax on your attention.
And what about the emails you never see? The over-aggressive filtering kills the chance for serendipity. Some of my best investments, like Scale AI and Hugging Face, came from unexpected introductions that a rigid algorithm would have probably flagged as “non-essential.” By trying to optimize everything, you can accidentally filter out the very opportunities that define a career.
The Counterintuitive Fix: My 326% Productivity Boost
I hit a wall. I was spending hours every week just managing my notes and summaries. It felt like I was running a library for documents I never read. I almost gave up on meeting notes entirely. What was the point?
During a dinner, I was complaining about this to a mentor, a seasoned operator who has seen it all. He laughed and told me I was thinking about it all wrong. His advice was completely counterintuitive. “Stop summarizing,” he said. “Stop trying to make everything neat. Just create a searchable, raw transcript of everything and build a system to pull what you need, when you need it.”
It felt wrong. It went against every productivity guru’s advice. But I was desperate, so I tried it. The result was staggering. After implementing this new AI-driven system, my personal productivity skyrocketed. I’m not guessing—I measured it. I reclaimed over 10 hours a week. That’s a 326% increase in the time I could dedicate to high-value work. Here’s the system.
Step 1: Record Everything (with permission, of course). Every important conversation—board meetings, founder pitches, strategy sessions—gets recorded.
Step 2: Get a Raw, Time-Stamped Transcript. I use an AI transcription service to get a simple, raw text file of the conversation. Not a summary. Not a list of action items. Just the words, as they were spoken, with timestamps.
Step 3: Tag It Live. This is the most important part. During the meeting, instead of taking detailed notes, I just type a few simple tags into a notepad. My system is basic:
#actionfor a specific to-do.#decisionfor a key choice that was made.#followupfor something I need to circle back on.#disagreefor a point of contention I want to remember.
That’s it. I’m not trying to capture every detail. I’m just planting signposts in the conversation. I’m fully present, listening and engaging, not buried in my laptop.
Step 4: Let the AI Do the Real Work. After the meeting, I run a simple script that takes the raw transcript and my list of tags. The script pulls the 30 seconds of conversation around each tag and organizes it into a clean, actionable brief. It’s not a summary; it’s a targeted extraction of the most critical moments.
Let me show you what this looks like. I had a pitch meeting with a founder building an AI robotics company. My old method would have been to furiously type notes, trying to capture the market size, the tech stack, and the team’s background, and I would have missed half of what was actually said. My new method? I was fully engaged. I just typed these three lines:
14:32 #action Send our robotics thesis.
28:15 #disagree on the go-to-market strategy.
45:10 #followup on their chip supplier.
Twenty minutes after the meeting, I had an automated email in my inbox with the audio snippets and transcriptions for just those three moments. I delegated the #action to my assistant, spent ten minutes writing a thoughtful reply about the go-to-market concerns, and scheduled a reminder to check on the supplier. The entire “work” of the meeting was done in 15 minutes.
Your Step-by-Step Guide to Stealing This System
You don’t need a team of engineers to do this. Here’s how you can set it up this week.
1. Choose Your Tools.
- For Transcription: Services like Otter.ai or Descript are fantastic and can do this out of the box. Many even let you add tags or highlights live.
- For Automation: You can use Zapier or even a simple Python script with the OpenAI API to process the text files. The prompt is straightforward: “Find the following tags in this transcript and extract the 30 seconds of text surrounding each one.”
2. The Workflow.
- Before a meeting, start your recorder and your transcription service.
- During the meeting, stay present. Listen. In a simple text file or notepad, just write down the timestamp and your tag.
- After the meeting, feed the transcript and your tags into your automation tool.
- Pipe the output directly into your task manager (like Asana, Trello, or just your email) so the actions and follow-ups are already in your workflow.
3. The Mindset Shift. This is the most critical part. You have to stop thinking of AI as a manager that tidies up your world. That’s a recipe for passive, low-impact work. Instead, think of it as an incredibly powerful, specialized intern. It’s bad at understanding nuance and making judgments, but it’s brilliant at brute-force tasks like transcribing audio and searching for keywords.
Your job is to be the strategist. You identify the critical moments in a conversation. The AI’s job is to do the grunt work of finding and organizing them for you.
Stop Letting AI Manage You
The productivity gurus are selling a fantasy. The idea that an AI can perfectly understand your priorities and manage your communication is, for now, a myth. Chasing that myth will leave you feeling busy but achieving very little.
Stop trying to automate your thinking. Stop letting AI assistants decide what’s important. Take back control. Use AI for what it’s good at: high-volume, low-nuance tasks. My meeting notes system is just one example. It works because it’s simple, it keeps me in the driver’s seat, and it frees up my attention for the things that actually matter: building relationships, making hard decisions, and finding the next great company.
I challenge you: try this for one week. Ditch the summary tools. Record your meetings, use a simple tagging system, and see how much time you get back. You’ll be shocked. It’s time to stop being managed by our tools and start using them to achieve real, meaningful results.
Frequently Asked Questions
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.
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 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.