Why Angel Investing Infrastructure Is Broken (And What We’re Building Instead)
Originally sent to Play Money subscribers · November 2025
Part of our ongoing series on angel investing, capital allocation, and the infrastructure we believe early-stage markets actually need.
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💎 Last week, I hit pause on our “how-to” angel tactics and wrote about the what and why behind Play Money.
Platforms aren’t supposed to have strong POVs.
It felt like a risk.
Turns out it drove more replies than any newsletter in months.
So here’s Part II.
— C2K
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The Angel and the Devil of Angel Investing
😇 Angel: The upside we create when capital works differently.
😈 Devil: The frustration with the status quo that forces us to build.
Let’s talk about the devil.
The Problem With Modern Angel Investing
Last month at the Bend Venture Conference, I opened with:
“Who loves startups?”
Hands everywhere.
Then I asked:
If we love founders so much, why are we doing them so dirty?
Here’s the current model of early-stage angel capital:
- Build a list of 400 angels, angel groups, and seed funds
- Chase warm intros
- Step away from running your business for 4+ months
- Repeat “tell me about your traction” endlessly
Pardon my French, but WTAF.
This isn’t capital efficiency.
It’s capitalism’s version of Where’s Waldo.
(If you’re newer to how angel investing actually works at the early stage, start with our guide to angel investing.)
The Fragmentation Tax Created by Angel Capital
One of the best things to happen to innovation is the explosion of new people writing checks.
More angels.
More diversity.
More geography.
More lived experience.
In theory, that should mean more innovation.
In practice?
It’s created fragmentation.
Every additional pitch.
Every duplicated diligence process.
Every scattered allocation decision.
That’s a tax.
A fragmentation tax on founders.
And by default, a tax on financial and societal returns.
Founders should spend their best hours with customers and product.
Not navigating capital chaos.
Why More Angels Haven’t Fixed the System
More capital allocators did not automatically produce better infrastructure.
Because the capital layer hasn’t innovated at the pace of the founders it funds.
We talk about backing disruptive companies.
But our own systems are anything but disruptive.
We’ve layered new capital on top of old processes.
And called it progress.
The Angel Fund I Didn’t Start
When I sold my last startup, the obvious move was:
Start a fund.
But I couldn’t add to the fragmentation.
The world does not need another micro-fund.
It needs better coordination.
Better infrastructure.
Not just a platform.
Not just a community.
A new layer in the angel capital stack.
Turning the Long Tail of Angel Investors Into Infrastructure
Here’s the math:
If just 20% of accredited investors invested $10K per year, we would dwarf today’s institutional capital from seed through Series A.
Dwarf it.
That’s the code we’re trying to crack.
Turn the long tail of angel investors into coordinated, high-signal capital.
Keep founders focused on building.
Reduce the fragmentation tax.
If you really love startups, this is the game to change.
— C2K
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