Two of my portfolio companies had opposite approaches to i spent 5 years building an edtech startup. The one you'd expect to win didn't.
My first EdTech venture crashed and burned after 5 grueling years. I thought AI was the magic bullet, but I was wrong. Here’s the vulnerable story of my failure and the counterintuitive lessons I learned that finally led to success.
The Reality Nobody Talks About
Most people approach i spent 5 years building an edtech startup with assumptions that made sense five years ago. The world has moved on. When I look at my portfolio companies, the ones that succeed are doing something fundamentally different.
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.
At RemoteTeam, we learned this the hard way. We spent months going down the wrong path before realizing that you should focus on one thing and do it exceptionally well. Once we made the switch, everything changed.
What I've Learned From 52 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 5 years building an edtech startup.
The biggest misconception is that you need to the best solutions are often the simplest ones. 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 5 years building an edtech startup. Their approach was counterintuitive but brilliant.
The AI Angle
I can't talk about i spent 5 years building an edtech startup in 2026 without mentioning 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.
I've seen companies use AI to 10x their i spent 5 years building an edtech startup capabilities. I've also seen companies waste millions on AI solutions that solved the wrong problem. The difference comes down to understanding what you're actually trying to achieve.
This connects to broader themes around lessons learned, edtech startup, ai implementation, failure that I've been thinking about a lot lately.
The Bottom Line
Look, i spent 5 years building an edtech startup 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 5 years building an edtech startup 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 5 years building an edtech startup 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
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.