Learning rolling funds the hard way is expensive; this is the short version.
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
A lot of the advice on rolling funds rests on assumptions that made sense five years ago. The world has moved on.
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.
Many teams spend months on the wrong path before realizing that the best solutions are often the simplest ones. Once they make the switch, everything changes.
What I've Learned From 35 Companies
A few patterns in rolling funds come up again and again.
The founders who handle rolling funds well understand that your team matters more than your technology.
The Counterintuitive Truth
In rolling funds, the best practitioners often do less, not more.
The lesson: the market doesn't care about your roadmap. It sounds simple. It's incredibly hard to execute.
The Numbers Don't Lie
Investing early in rolling funds can be 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
Best practice in rolling funds is changing 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.
If you're building in this space, the best time to get rolling funds 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
Q: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.
Q: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.
Q: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 234 startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.
Q: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.