I wanted to share my perspective on this. We just finished a massive study analyzing over 10,000 individual student sessions with our AI tutor. The data revealed 3 shocking patterns in how students actually learn with AI, and it’s not what the experts tell you. The truth is in the numbers.
The Counterintuitive Truth
In AI tutoring, the best practitioners often do less, not more.
The lesson: you need to move fast and break things. It sounds simple. It's incredibly hard to execute.
The Reality Nobody Talks About
A lot of the advice on AI tutoring 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 you should focus on one thing and do it exceptionally well. Once they make the switch, everything changes.
What I've Learned From 64 Companies
A few patterns in AI tutoring come up again and again.
The founders who handle AI tutoring well understand that the market doesn't care about your roadmap.
The AI Angle
Any discussion of AI tutoring in 2026 has to include AI. As someone who's invested in Anthropic, OpenAI, Scale AI, and Hugging Face, I have a front-row seat to how AI is transforming this space.
The short version: AI makes good practitioners better and bad practitioners worse. It's an amplifier, not a replacement.
Some teams use AI to get far more out of AI tutoring. Others spend heavily on AI that solves the wrong problem. The difference comes down to understanding what you're actually trying to achieve.
This connects to broader themes around student data, ai tutor, edtech research, learning analytics 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 tutoring right on day one. You just need to get started and keep improving.
Founders who do well at AI tutoring 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: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: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.
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.