People always ask me how I manage my angel portfolio. The answer is a disciplined system built around follow-on investing. I'm giving you a transparent, behind-the-scenes look at my exact process, templates, and the software I use to track everything.
Why Most Approaches Fail
Many common approaches to follow-on investing are flawed at the root.
The root cause is usually one of three things:
Copying what big companies do without understanding why they do it. What works for Google doesn't work for a 10-person startup.
Over-engineering the solution when a simple approach would work better. I've seen teams spend six months building something that could have been done in two weeks.
Ignoring the human element. Technology is the easy part. Getting people to actually use it is where the real challenge lives.
The Counterintuitive Truth
In follow-on investing, the best practitioners often do less, not more.
The lesson: the best solutions are often the simplest ones. It sounds simple. It's incredibly hard to execute.
The Framework That Actually Works
Here is a simple framework for evaluating follow-on investing. It's not complicated, but it requires discipline.
Step 1: the best solutions are often the simplest ones
This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.
Step 2: timing is everything in this game
Once you have the foundation right, this becomes much easier. I've watched founders struggle with this for months when the answer was staring them in the face.
Step 3: Iterate relentlessly
Nothing works perfectly the first time. The companies that get follow-on investing right treat it as an ongoing process, not a one-time project.
The Numbers Don't Lie
Investing early in follow-on investing can be the difference between raising your next round and running out of runway.
One of my portfolio companies went from struggling to profitable in under a year after they finally got serious about this. The founder told me later that they wished they'd started sooner.
This connects to broader themes around follow-on investing, secondary markets, 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 you don't need to get follow-on investing right on day one. You just need to get started and keep improving.
Founders who do well at follow-on investing tend to 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
Q: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.
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: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.
Q: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.