Last year, I made a bet that changed how I think about what 8 years of building product-led growth taught me. Here's what happened.
I'll share the real playbook we used to get to a 7-figure exit, including the costly mistakes and the hard lessons that actually paid off.
Why Most Approaches Fail
Let me be direct: about 70% of the approaches I see to what 8 years of building product-led growth taught me 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.
The Reality Nobody Talks About
Most people approach what 8 years of building product-led growth taught me 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 the market doesn't care about your roadmap. 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 customer feedback is the only metric that matters. Once we made the switch, everything changed.
The Framework That Actually Works
I'm going to share the exact framework I use when evaluating what 8 years of building product-led growth taught me. It's not complicated, but it requires discipline.
Step 1: most founders overthink this and underspend on execution This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.
Step 2: you need to move fast and break things 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 what 8 years of building product-led growth taught me are the ones that treat it as an ongoing process, not a one-time project.
The AI Angle
I can't talk about what 8 years of building product-led growth taught me 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 what 8 years of building product-led growth taught me 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 viral loops, content marketing, SEO for startups, community-led growth that I've been thinking about a lot lately.
Final Thoughts
After two exits, 200+ investments, and more mistakes than I can count, here's what I know for sure about what 8 years of building product-led growth taught me: there are no shortcuts, but there are smarter paths.
The smartest founders I work with treat what 8 years of building product-led growth taught me as a competitive advantage, not a checkbox. They invest in it early, measure it obsessively, and never stop improving.
If you're just getting started with what 8 years of building product-led growth taught me, don't be intimidated. Everyone starts somewhere. The key is to start with the right mindset and the right framework, and then execute like your company depends on it. Because it probably does.
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.