I spent $50,000 learning this lesson about a behind-the-scenes look at how we use rolling the hard way. You can learn it in 10 minutes.
People always ask me how we manage our portfolio of 5 companies. The answer is a disciplined system built around rolling funds. I'm giving you a transparent, behind-the-scenes look at our exact process, templates, and the software we use to track everything.
The Reality Nobody Talks About
Most people approach a behind-the-scenes look at how we use rolling 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 the best solutions are often the simplest ones. Once we made the switch, everything changed.
What I've Learned From 35 Companies
After investing in 200+ startups and running two companies to successful exits, I've developed a pretty clear picture of what works with a behind-the-scenes look at how we use rolling.
The biggest misconception is that you need to you need to move fast and break things. That's backwards. The companies that win are the ones that your team matters more than your technology.
I remember sitting with the Anthropic team early on and discussing how they thought about a behind-the-scenes look at how we use rolling. Their approach was counterintuitive but brilliant.
The Counterintuitive Truth
Here's what surprised me most about a behind-the-scenes look at how we use rolling: 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 the market doesn't care about your roadmap. It sounds simple. It's incredibly hard to execute.
The Numbers Don't Lie
I've tracked the performance of companies in my portfolio that take a behind-the-scenes look at how we use rolling seriously versus those that don't. The difference is stark.
Companies that invest early in a behind-the-scenes look at how we use rolling see, on average, 2-3x better outcomes within 18 months. That's not a small edge. That's the difference between raising your next round and running out of runway.
One of my portfolio companies went from struggling to profitable in under a year after they finally got serious about this. The founder told me later that they wished they'd started sooner.
This connects to broader themes around rolling funds, secondary markets, term sheets that I've been thinking about a lot lately.
What's Next
The world of a behind-the-scenes look at how we use rolling 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 a behind-the-scenes look at how we use rolling 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
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.
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.
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.