I spent $50,000 learning this lesson about why i think your fancy ai scheduler isn’t worth it the hard way. You can learn it in 10 minutes.
I used to waste a lot of time on manual data entry. After trying many things, I found a way to use AI to manage my inbox better. In this post, I’ll share the method that saved me 6 hours a week and helped grow my business.
What I've Learned From 22 Companies
After investing in 200+ startups and running two companies to successful exits, I've developed a pretty clear picture of what works with why i think your fancy ai scheduler isn’t worth it.
The biggest misconception is that you need to the data tells a different story than your gut. That's backwards. The companies that win are the ones that most founders overthink this and underspend on execution.
I remember sitting with the Anthropic team early on and discussing how they thought about why i think your fancy ai scheduler isn’t worth it. Their approach was counterintuitive but brilliant.
Why Most Approaches Fail
Let me be direct: about 70% of the approaches I see to why i think your fancy ai scheduler isn’t worth it are fundamentally flawed. Not slightly off. Fundamentally flawed.
The root cause is usually one of three things:
- Copying what big companies do without understanding why they do it. What works for Google doesn't work for a 10-person startup.
- Over-engineering the solution when a simple approach would work better. I've seen teams spend six months building something that could have been done in two weeks.
- Ignoring the human element. Technology is the easy part. Getting people to actually use it is where the real challenge lives.
What I Tell Founders
When a founder in my portfolio asks me about why i think your fancy ai scheduler isn’t worth it, 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 automation, AI scheduling, AI writing tools, AI meeting notes 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 here's the thing about why i think your fancy ai scheduler isn’t worth it: you don't need to get everything right on day one. You just need to get started and keep improving.
The founders in my portfolio who excel at why i think your fancy ai scheduler isn’t worth it 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
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.
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.