I've been investing in AI companies since before it was cool. i spent 13 years wasting time on scheduling is the thing that separates winners from losers.
For years, I struggled with context switching. I tried everything, but nothing worked until I discovered how to leverage AI for an AI-powered inbox. In this post, I'm sharing the exact framework that helped me reclaim 14 hours per week and scale my business.
What I've Learned From 60 Companies
After investing in 200+ startups and running two companies to successful exits, I've developed a pretty clear picture of what works with i spent 13 years wasting time on scheduling.
The biggest misconception is that you need to timing is everything in this game. That's backwards. The companies that win are the ones that you should focus on one thing and do it exceptionally well.
I remember sitting with the Anthropic team early on and discussing how they thought about i spent 13 years wasting time on scheduling. Their approach was counterintuitive but brilliant.
The Framework That Actually Works
I'm going to share the exact framework I use when evaluating i spent 13 years wasting time on scheduling. It's not complicated, but it requires discipline.
Step 1: the data tells a different story than your gut This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.
Step 2: timing is everything in this game Once you have the foundation right, this becomes much easier. I've watched founders struggle with this for months when the answer was staring them in the face.
Step 3: Iterate relentlessly Nothing works perfectly the first time. The companies in my portfolio that nail i spent 13 years wasting time on scheduling are the ones that treat it as an ongoing process, not a one-time project.
The Counterintuitive Truth
Here's what surprised me most about i spent 13 years wasting time on scheduling: the best practitioners do less, not more.
When I was building MovieLaLa, we tried to do everything at once. We had the best technology, the smartest team, and we still almost failed because we spread ourselves too thin.
The lesson I took from that experience, and from watching hundreds of other companies, is that the best solutions are often the simplest ones. It sounds simple. It's incredibly hard to execute.
What I Tell Founders
When a founder in my portfolio asks me about i spent 13 years wasting time on scheduling, I usually start with three questions:
- What's your timeline? Because the right approach for a company with 6 months of runway is very different from one with 3 years.
- What have you already tried? Most founders have tried something. Understanding what didn't work is often more valuable than knowing what might.
- Who on your team owns this? If the answer is "everyone" or "no one," that's your first problem to solve.
These questions seem simple but they reveal a lot about where a company actually stands.
This connects to broader themes around AI personal assistant, AI scheduling, AI automation that I've been thinking about a lot lately.
The Bottom Line
Look, i spent 13 years wasting time on scheduling isn't rocket science. But it does require intentionality, consistency, and a willingness to learn from mistakes.
If you take one thing from this article, let it be this: start now, start small, and iterate. The founders who win at i spent 13 years wasting time on scheduling aren't the ones with the best strategy on paper. They're the ones who execute, learn, and adapt faster than everyone else.
I've been doing this for over a decade. The patterns are clear. The companies that take i spent 13 years wasting time on scheduling seriously outperform the ones that don't. Every single time.
If you're working on something interesting in this space, I'd love to hear about it. Drop me a line.
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.
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.