Three years ago, I sat across from a founder who was about to make the same mistake I made with 14 things i learned about secondary markets after. I told them the truth.
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
Here's what surprised me most about 14 things i learned about secondary markets after: 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 timing is everything in this game. It sounds simple. It's incredibly hard to execute.
The Reality Nobody Talks About
Most people approach 14 things i learned about secondary markets after 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 simplicity beats complexity every time. 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 you need to move fast and break things. Once we made the switch, everything changed.
What I Tell Founders
When a founder in my portfolio asks me about 14 things i learned about secondary markets after, 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 secondary markets, cap tables, SPVs, syndicate investing that I've been thinking about a lot lately.
The Bottom Line
Look, 14 things i learned about secondary markets after 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 14 things i learned about secondary markets after 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 14 things i learned about secondary markets after 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
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 200+ startups I've invested in. I prioritize practical, actionable items over theoretical concepts.
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.
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.
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.