I've had this conversation about the truth about follow-on investing: what your vc with at least 50 founders. Here's the distilled version.
I've sat on both sides of the table. As a founder, I was often in the dark. As a VC, I learned the unwritten rules of the game. I'm pulling back the curtain on follow-on investing and revealing what investors are really thinking when they send you that document.
The Counterintuitive Truth
Here's what surprised me most about the truth about follow-on investing: what your vc: 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 most founders overthink this and underspend on execution. It sounds simple. It's incredibly hard to execute.
What I've Learned From 131 Companies
After investing in 200+ startups and running two companies to successful exits, I've developed a pretty clear picture of what works with the truth about follow-on investing: what your vc.
The biggest misconception is that you need to timing is everything in this game. That's backwards. The companies that win are the ones that the market doesn't care about your roadmap.
I remember sitting with the Anthropic team early on and discussing how they thought about the truth about follow-on investing: what your vc. Their approach was counterintuitive but brilliant.
The Reality Nobody Talks About
Most people approach the truth about follow-on investing: what your vc 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 you need to move fast and break things. 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 Tell Founders
When a founder in my portfolio asks me about the truth about follow-on investing: what your vc, 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 follow-on investing, syndicate investing, dilution, secondary markets, portfolio construction that I've been thinking about a lot lately.
The Bottom Line
Look, the truth about follow-on investing: what your vc isn't rocket science. But it does require intentionality, consistency, and a willingness to learn from mistakes.
If you take one thing from this article, let it be this: start now, start small, and iterate. The founders who win at the truth about follow-on investing: what your vc aren't the ones with the best strategy on paper. They're the ones who execute, learn, and adapt faster than everyone else.
I've been doing this for over a decade. The patterns are clear. The companies that take the truth about follow-on investing: what your vc seriously outperform the ones that don't. Every single time.
If you're working on something interesting in this space, I'd love to hear about it. Drop me a line.
Frequently Asked Questions
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.
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.