The best advice I ever got about what we did to keep 90% of our users over 6 months came from a founder who'd failed at it three times.
Let me share the real story behind reaching 1 million users. I’ll be honest about the mistakes we made, the data we learned from, and what surprised me along the way.
The Reality Nobody Talks About
Most people approach what we did to keep 90% of our users over 6 months 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 most founders overthink this and underspend on execution. 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 we did to keep 90% of our users over 6 months. It's not complicated, but it requires discipline.
Step 1: the best solutions are often the simplest ones This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.
Step 2: you should focus on one thing and do it exceptionally well 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 we did to keep 90% of our users over 6 months are the ones that treat it as an ongoing process, not a one-time project.
What I Tell Founders
When a founder in my portfolio asks me about what we did to keep 90% of our users over 6 months, 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 viral loops, SEO for startups, referral programs, community-led growth, growth hacking 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 we did to keep 90% of our users over 6 months: there are no shortcuts, but there are smarter paths.
The smartest founders I work with treat what we did to keep 90% of our users over 6 months 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 we did to keep 90% of our users over 6 months, 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.
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 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.