After burning out trying to do everything myself, I went all-in on AI. Some experiments were a disaster, but others were life-changing. I'm opening up my playbook to show you what worked, what didn't, and how to build your own AI-powered personal OS.
The Reality Nobody Talks About
A lot of the advice on AI scheduling tools rests on assumptions that made sense five years ago. The world has moved on.
The first thing to understand is that customer feedback is the only metric that matters. I've seen this play out across dozens of companies. The pattern is unmistakable.
Many teams spend months on the wrong path before realizing that timing is everything in this game. Once they make the switch, everything changes.
The Counterintuitive Truth
In AI scheduling tools, the best practitioners often do less, not more.
The lesson: you should focus on one thing and do it exceptionally well. It sounds simple. It's incredibly hard to execute.
Real Talk: What Actually Matters
Here is what actually matters in AI scheduling tools.
First, execution speed beats perfection. Every time. Companies rarely fail because they moved too fast on AI scheduling tools. Many fail because they moved too slowly.
Second, measure everything. If you can't measure it, you can't improve it. Set up tracking from day one, even if it's basic.
Third, talk to your users. It sounds obvious, but many founders make decisions about AI scheduling tools in a vacuum. Get out of the building. Talk to real people.
This connects to broader themes around AI automation, AI writing tools, AI email, AI tools for founders that I've been thinking about a lot lately.
Wrapping Up
I've shared a lot here, and I know it can feel overwhelming. But you don't need to get AI scheduling tools right on day one. You just need to get started and keep improving.
Founders who do well at AI scheduling tools tend to share one trait: they're relentlessly practical. They don't chase perfection. They chase progress.
That's the mindset I'd encourage you to adopt. Start where you are. Use what you have. Do what you can. And keep pushing forward.
As always, I'm rooting for you.
Frequently Asked Questions
Q: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.
Q: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 234 startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.
Q: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.
Q: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.