I've been an angel investor for 11 years, and my understanding of secondary markets has been completely transformed. These aren't the textbook lessons; these are the hard-won insights from the trenches. Here are the 14 most critical things I wish I knew when I started.
The Counterintuitive Truth
In secondary markets, the best practitioners often do less, not more.
The lesson: timing is everything in this game. It sounds simple. It's incredibly hard to execute.
The Reality Nobody Talks About
A lot of the advice on secondary markets rests on assumptions that made sense five years ago. The world has moved on.
The first thing to understand is that simplicity beats complexity every time. 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 you need to move fast and break things. Once they make the switch, everything changes.
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, cap tables, SPVs, syndicate investing that I've been thinking about a lot lately.
The Bottom Line
None of this is 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 secondary markets aren't the ones with the best strategy on paper. They're the ones who execute, learn, and adapt faster than everyone else.
Companies that take secondary markets seriously tend to pull ahead of the ones that don't.
If you're working on something interesting in this space, I'd love to hear about it. Drop me a line.
Frequently Asked Questions
Q:How were these items selected?
Each item on this list comes from direct experience, either from building my own companies or from patterns I've observed across the 234 startups I've invested in. I prioritize practical, actionable items over theoretical concepts.
Q:Can I implement all of these at once?
I'd strongly recommend against it. Pick the 2-3 items that resonate most with your current situation and focus there. Trying to do everything simultaneously is a recipe for doing nothing well.
Q:How do I know which items apply to my situation?
Start by honestly assessing where your biggest bottleneck is right now. The items that address that specific constraint will give you the highest return on your time and energy.
Q:Which item on this list has the highest impact?
It depends on your stage and context, but in my experience, the items near the top of the list tend to have the broadest applicability. That said, sometimes the less obvious items create the biggest breakthroughs for specific situations.