During the MovieLaLa days, we learned something about why your obsession with rolling funds is actually that I still apply to every investment I make.
Every VC blog tells you to focus on rolling funds. I'm here to tell you that's terrible advice. I've seen more startups fail because of a premature obsession with rolling funds than almost any other reason. Here's the counterintuitive truth about what you should be focusing on instead.
Why Most Approaches Fail
Let me be direct: about 70% of the approaches I see to why your obsession with rolling funds is actually 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 why your obsession with rolling funds is actually 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 most founders overthink this and underspend on execution. Once we made the switch, everything changed.
The Counterintuitive Truth
Here's what surprised me most about why your obsession with rolling funds is actually: the best practitioners do less, not more.
When I was building MovieLaLa, we tried to do everything at once. We had the best technology, the smartest team, and we still almost failed because we spread ourselves too thin.
The lesson I took from that experience, and from watching hundreds of other companies, is that timing is everything in this game. It sounds simple. It's incredibly hard to execute.
The AI Angle
I can't talk about why your obsession with rolling funds is actually 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 why your obsession with rolling funds is actually 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 rolling funds, dilution, follow-on investing that I've been thinking about a lot lately.
What's Next
The world of why your obsession with rolling funds is actually is moving fast. What worked last year might not work next year. That's both the challenge and the opportunity.
My advice: stay curious, stay humble, and stay close to the people who are actually doing the work. Read less thought leadership and do more experiments. Talk to fewer consultants and more practitioners.
And if you're a founder building in this space, remember that the best time to get why your obsession with rolling funds is actually right is before you need to. Don't wait for a crisis to force your hand.
I'll keep sharing what I learn. This stuff matters too much to keep to myself.
Frequently Asked Questions
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 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.
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.