I’m going to say something that might make a few people in Silicon Valley mad. Your fancy AI scheduler is probably a waste of money.
There, I said it. And I’m not just saying it to be a contrarian. I’m saying it after spending six months and over $5,000 testing every AI productivity tool I could get my hands on. I’m talking about the whole gamut of AI-powered calendars, to-do lists, and personal assistants that promise to organize your life and make you a productivity god.
And you know what I found? Most of them are just glorified to-do lists with a pretty interface. They’re great at making you feel productive, but they don’t actually help you get the important stuff done.
The Allure of the AI Assistant
I get it. The idea of an AI assistant that manages your schedule, prioritizes your tasks, and even writes your emails is incredibly appealing. As a serial entrepreneur and angel investor, my life is a constant juggling act of meetings, emails, and a never-ending to-do list. I’ve built and sold two companies, RemoteTeam and MovieLaLa, and I’ve invested in over 200 startups, including some of the biggest names in AI like Anthropic, OpenAI, and Scale AI. So, believe me, I understand the need for efficiency.
But here’s the thing: I’ve learned that true productivity isn’t about having a perfectly organized calendar. It’s about focus. It’s about knowing what’s important and what’s not, and then having the discipline to work on the important stuff, even when the urgent stuff is screaming for your attention.
And that’s where most AI schedulers fall short. They’re great at managing the urgent, but they’re terrible at helping you focus on the important.
My $5,000 Experiment
For six months, I went all-in on AI productivity tools. I tried everything from the big names to the up-and-comers. I synced my calendars, imported my to-do lists, and let the algorithms do their thing. At first, it was magical. My days were perfectly scheduled, my tasks were neatly organized, and I had a beautiful dashboard that showed me exactly what I needed to do and when.
But after a few weeks, I started to notice a problem. I was busier than ever, but I wasn't actually getting more done. I was spending so much time managing my AI scheduler—tweaking settings, re-prioritizing tasks, and dealing with scheduling conflicts—that I had less time for deep work.
I was a slave to the algorithm. I was so focused on completing the tasks that the AI had laid out for me that I lost sight of the bigger picture. I was mistaking activity for achievement.
The Simple System That Actually Works
So, I did what any frustrated entrepreneur would do. I scrapped the whole system and went back to basics. And you know what? It was the best decision I ever made.
My current productivity system is ridiculously simple. It consists of three things:
A physical notebook: I use a simple notebook and pen to plan my day. Every morning, I write down the three most important things I need to accomplish. That’s it. Just three things. This forces me to be ruthless about prioritization.
A simple to-do list app: I use a basic to-do list app on my phone to capture all the other tasks that pop into my head throughout the day. I don’t worry about prioritizing them or scheduling them. I just dump them in there so I don’t forget.
A calendar: I use a standard calendar app to schedule my meetings and appointments. I don’t let it dictate my day. I use it as a tool to manage my commitments, not my time.
That’s it. No fancy AI, no complicated algorithms, just a simple system that helps me focus on what’s important.
Where AI Can Help
Now, don’t get me wrong. I’m not anti-AI. In fact, I’m a huge believer in its potential to transform the way we work. I just think we’re focusing on the wrong things.
Instead of trying to build an AI that can manage our entire lives, we should be building AI tools that can automate specific, time-consuming tasks. For example, I use an AI-powered transcription service to transcribe my meetings. This saves me hours of time and allows me to focus on the conversation, not on taking notes.
I also use an AI-powered email assistant to help me sort through my inbox and draft replies. This has been a game-changer for me. I used to spend hours every day on email, but now I can get through my inbox in a fraction of the time.
These are the kinds of AI tools that are actually worth the money. They’re not trying to be your boss. They’re just trying to be your assistant. And that’s a crucial distinction.
The Takeaway
So, here’s my contrarian hot take: stop wasting your money on fancy AI schedulers. They’re not going to make you more productive. They’re just going to make you busier.
Instead, focus on building a simple system that helps you prioritize what’s important and then use AI to automate the tedious, time-consuming tasks that are getting in your way.
That’s the real secret to productivity. It’s not about having a perfect schedule. It’s about having the focus and discipline to work on the right things, day in and day out. And no AI, no matter how fancy, can do that for you.
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.
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.
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.