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Why Most Founders Get AI Personal Tasks Completely Wrong (And How to Fix It)
I’m going to say something that might get me in trouble. Most founders are using AI for their personal tasks completely wrong. There, I said it.
I see it all the time. Founders who are brilliant at building products, but when it comes to their own productivity, they’re throwing money at expensive, complicated AI software that promises to solve all their problems. They’re drowning in a sea of AI-powered to-do lists, schedulers, and email assistants, and they’re still not getting anything done.
Here’s the thing: I built a multi-million dollar company, RemoteTeam, which was acquired by Gusto. I’ve made over 200 angel investments in companies like Anthropic, OpenAI, Scale AI, and Hugging Face. I wrote a book, "Becoming Top 1%". And I did it all without a team of personal assistants or a seven-figure software budget. I did it by being smart about how I use my time and my tools. And a big part of that is my approach to AI.
I’m not a Luddite. I’m a huge believer in the power of AI. But I’m also a pragmatist. I believe in using the right tool for the right job. And for most personal tasks, the right tool is often the simplest one.
In this article, I’m going to share my framework for thinking differently about AI for personal tasks. I’m going to show you how to get 10x the results with a fraction of the effort. And I’m going to reveal my entire AI stack and workflow, so you can steal it and start getting your life back.
The Allure of the Shiny New Toy
I get it. The AI area is exploding. There’s a new tool coming out every day that promises to revolutionize the way you work. It’s easy to get caught up in the hype. I’ve been there myself. I remember when I first started playing around with AI tools. I was like a kid in a candy store. I signed up for every free trial I could find. I had AI-powered everything: email, calendar, notes, even an AI-powered water bottle that reminded me to stay hydrated. (I’m not kidding.)
But after a few weeks of this, I realized something. I was spending more time managing my AI tools than I was actually getting work done. I was constantly switching between different apps, trying to figure out which one was best for which task. It was a mess.
And I see the same pattern with so many founders today. They’re so focused on finding the “perfect” AI tool that they lose sight of the bigger picture. They’re optimizing for the wrong thing.
My "Less is More" AI Framework
After my initial failed experiment with AI, I took a step back and re-evaluated my approach. I realized that I didn’t need more tools. I needed a better framework. So I came up with a simple set of principles that I still use to this day.
1. Less is More.
This is the most important principle. You don’t need a dozen different AI tools to be productive. In fact, the more tools you have, the less productive you’re likely to be. I’ve found that a few simple, powerful tools are all you need. For me, that’s a combination of a smart calendar, a powerful email client, and a flexible note-taking app. That’s it. Everything else is just a distraction.
2. Automate the Right Things.
Not all tasks are created equal. Some tasks are perfect candidates for automation, while others are better left to a human. The key is to identify the tasks that are truly time-consuming and repetitive. For me, that’s things like scheduling meetings, transcribing interviews, and summarizing long articles. These are the tasks that I’ve automated with AI. But for tasks that require creativity, critical thinking, or personal connection, I still do them myself. For example, I would never use AI to write a personal email to a friend or to brainstorm ideas for a new product. Those are the tasks that I enjoy, and they’re the tasks that make me human.
3. The 80/20 Rule of AI.
This is a classic for a reason. In my experience, 80% of the value of AI comes from 20% of its features. So instead of trying to master every single feature of every single tool, I focus on the few features that give me the most tap into. For example, with my AI-powered email client, I don’t use all the fancy features like automatic email generation or sentiment analysis. I just use the smart inbox and the snooze feature. Those two features alone save me hours every week.
My Personal AI Stack
So what tools do I actually use? Here’s my current AI stack for personal tasks:
Scheduling: Calendly. I know, it’s not the sexiest tool on the market. But it’s simple, it’s reliable, and it gets the job done. I’ve tried all the fancy AI-powered schedulers, and I always come back to Calendly. It’s just so easy to use. I can set up different event types for different types of meetings, and I can share my link with anyone and they can book a time with me in seconds. It’s a lifesaver.
Email: Superhuman. This is one of the few premium tools that I think is actually worth the money. Superhuman is an AI-powered email client that helps you get through your inbox twice as fast. It has a bunch of great features, but the one I love the most is the keyboard shortcuts. I can archive, snooze, and reply to emails without ever touching my mouse. It’s a breakthrough. If you’re serious about email productivity, you need to check it out.
Meeting Notes: Otter.ai. I have a lot of meetings. And I used to spend hours every week transcribing my notes. But now I use Otter.ai. It’s an AI-powered transcription service that automatically transcribes your meetings in real-time. It’s not perfect, but it’s pretty darn close. And it saves me a ton of time. I can just focus on the conversation, and then I can go back and review the transcript later. It’s a huge weight off my shoulders.
A Real-World Example
I remember when I was raising money for RemoteTeam. I was having dozens of meetings with investors every week. It was a full-time job just managing my schedule. I was constantly going back and forth with people trying to find a time that worked for everyone. It was a nightmare.
Then I started using Calendly. I just sent my link to all the investors, and they could book a time with me in seconds. It was a revelation. I probably saved 10 hours a week just on scheduling alone. That’s 10 hours that I could spend on more important things, like building my product and talking to customers.
And that’s the power of using AI the right way. It’s not about having the fanciest tools. It’s about having the right tools and using them in the right way. It’s about being smart and strategic. It’s about being a founder, not a follower.
It’s Your Turn
Look, I’m not saying that my way is the only way. But I am saying that if you’re feeling overwhelmed by all the AI tools out there, you’re not alone. And I’m saying that there’s a better way.
So here’s my challenge to you: take a look at your own AI stack. Are you using too many tools? Are you automating the right things? Are you focused on the 20% of features that give you 80% of the results?
If the answer is no, then it’s time to make a change. Ditch the tools that aren’t working for you. Focus on the ones that are. And start using AI to get your life back.
And if you want to learn more about my approach to productivity and investing, you can check out my post on my investment in OpenAI or my guide on how I use AI to read 100 books a year.
Now go build something amazing. '''
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 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.
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.