The venture landscape is shifting under our feet. The old way of doing things is dying. Based on what I'm seeing in the market, a deep understanding of secondary markets is about to become the single most critical differentiator for successful investors in 2025. Here's why and how to get ahead of the curve.
What I've Learned From 39 Companies
A few patterns in secondary markets come up again and again.
The founders who handle secondary markets well understand that simplicity beats complexity every time.
The Counterintuitive Truth
In secondary markets, the best practitioners often do less, not more.
The lesson: customer feedback is the only metric that matters. It sounds simple. It's incredibly hard to execute.
What I Tell Founders
Before deciding anything about secondary markets, 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 secondary markets, SPVs, syndicate investing that I've been thinking about a lot lately.
What's Next
Best practice in secondary markets 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 secondary markets 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: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 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.