During the MovieLaLa days, we learned something about 12 things i learned about portfolio construction after that I still apply to every investment I make.
I've been an angel investor for 15 years, and my understanding of portfolio construction has been completely transformed. These aren't the textbook lessons; these are the hard-won insights from the trenches. Here are the 12 most critical things I wish I knew when I started.
What I've Learned From 141 Companies
After investing in 200+ startups and running two companies to successful exits, I've developed a pretty clear picture of what works with 12 things i learned about portfolio construction after.
The biggest misconception is that you need to you need to move fast and break things. That's backwards. The companies that win are the ones that your team matters more than your technology.
I remember sitting with the Anthropic team early on and discussing how they thought about 12 things i learned about portfolio construction after. Their approach was counterintuitive but brilliant.
The Reality Nobody Talks About
Most people approach 12 things i learned about portfolio construction 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 you should focus on one thing and do it exceptionally well. 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.
The Counterintuitive Truth
Here's what surprised me most about 12 things i learned about portfolio construction 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 the best solutions are often the simplest ones. It sounds simple. It's incredibly hard to execute.
What I Tell Founders
When a founder in my portfolio asks me about 12 things i learned about portfolio construction 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 portfolio construction, dilution, syndicate investing that I've been thinking about a lot lately.
Wrapping Up
I've shared a lot here, and I know it can feel overwhelming. But here's the thing about 12 things i learned about portfolio construction after: you don't need to get everything right on day one. You just need to get started and keep improving.
The founders in my portfolio who excel at 12 things i learned about portfolio construction after share one trait: they're relentlessly practical. They don't chase perfection. They chase progress.
That's the mindset I'd encourage you to adopt. Start where you are. Use what you have. Do what you can. And keep pushing forward.
As always, I'm rooting for you.
Frequently Asked Questions
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 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.
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.
Are these recommendations still relevant in 2026?
Absolutely. While specific tools and tactics change, the underlying principles remain consistent. I update my thinking regularly based on what I'm seeing in the market and across my portfolio companies.