Introducing Signals by Simon.
What's actually changing in AI, and what it means for how companies get built, funded, and scaled.
AI is moving fast. Every week brings another wave of announcements, benchmarks, and breathless takes.
I’m not going to recap the news. There are a million places for that.
What I want to do is slower and more useful: make sense of what’s actually changing — and what it means for how companies get built, funded, and scaled. Because the old playbook has changed. First principles haven’t.
I’ve spent the last decade trying to be the most helpful investor on the cap table — regardless of when we invested or the size of the check. Not the biggest. Not the loudest. The most useful. That orientation shapes everything about how I think about what actually matters at each stage of building.
I’ve been through a reset before. The GFC changed how a generation of companies got built — what capital meant, what sustainable looked like, what founders had to actually figure out on their own. This moment feels different in speed. But some of the underlying dynamics rhyme.
I’m intellectually curious, probably too glass-half-empty, and genuinely trying to make sense of this alongside the founders I work with. These are loosely held opinions - I’m hoping you’ll push back.
The rounds happening right now are dizzying. Valuations that would have been unthinkable two years ago are getting done weekly. Some of it is real. Some of it is kingmaking. Making the distinction is the whole game - and most of the frameworks people use were built for a different era.
The old growth benchmarks — triple triple double — were a proxy for something real: repeatable, leveraged distribution. Companies are now blowing past those numbers. The AI adoption cycle is faster and steeper than anything SaaS produced. But the thing those benchmarks were actually measuring? Harder to find than ever.
A few things I keep seeing:
→ Revenue can scale before leverage appears
→ Large contracts can mask fragile economics
→ Strong retention can look like PMF when you’re actually running a human-powered services firm financed with the wrong capital
The challenge isn’t reacting faster to headlines. It’s understanding what’s actually changing underneath the numbers.
Where I can, I’ll bring data, not to prove a point, but to pressure-test one. And I’ll share observations from the field: what’s getting funded, what the bar actually looks like right now, and where I think the market is pattern-matching to the wrong era.
Signals by Simon are short posts, loosely held opinions and honest questions. Not predictions — I’m not trying to will anything into existence.
The first series starts with a simple question:
AI is labor, so what does that software company actually look like?