Kill the Stack
The structural problems hiding inside your company
You know the feeling. Everything looks like it’s working — the tools are running, the team is busy, the dashboards are green — but something is off. Growth is slower than it should be. Headcount keeps climbing but output doesn’t follow. Margins thin and nobody can explain why.
The problem isn’t what you can see. It’s what you can’t.
I run a lending infrastructure company. I see this every day in the mortgage industry — a file sits in “pending” for three days, but the actual decision took twenty minutes. The rest is waiting. Waiting for data to move between systems that were never designed to talk to each other. Twenty tools to close one deal, and most of the cost isn’t in any one of them. It’s in the handoffs, the re-keying, the invisible queues that don’t show up on any dashboard.
But here’s the thing: it’s not just lending. Every company I’ve looked at has the same pattern hiding underneath. Tech debt nobody’s paying down. Processes that exist because someone needed a workaround five years ago and it calcified. Meetings that run because no system surfaces the information automatically. People who’ve become middleware between tools that should talk to each other.
The most expensive thing in your company is almost certainly something you’ve never measured. It’s structural. It’s hidden. And it’s compounding.
So I started writing about it. That’s Kill the Stack.
What this newsletter is about
Kill the Stack is about the structural problems hiding inside companies — the ones that don’t show up on any P&L but determine whether you scale or stall.
Tech debt. Process debt. Attention debt. Vendor lock-in. The founder as bottleneck. The space between your systems where time and money go to die.
I write from the perspective of a founder-operator who builds lending technology and lives inside these problems every day. This isn’t theory. It’s diagnosis — the kind you get from someone who’s pulled apart enough broken stacks to know what the symptoms mean.
The thesis is simple: most companies are optimizing the wrong things. They buy better tools while the architecture underneath gets worse. They hire more people to manage friction instead of eliminating it. They measure what’s visible and ignore what’s structural.
Kill the Stack is about seeing those problems clearly enough to fix them.
What to expect
Kill the Stack essays — Deep posts on the structural problems hiding inside companies and lending operations. Why your calendar is a legacy system. Why productivity is falling despite record technology spending. Why the most expensive thing in your company is invisible. One main post per week.
Kill the Stack Weekly — A Monday morning roundup of the most important mortgage industry news across the US and Canada, with my personal take on each story. Not a neutral recap — opinionated commentary through the Kill the Stack lens. What happened, and what it actually means for your infrastructure.
Both are free. I’m not building a paywall. I’m building a conversation.
Who this is for
If you’ve ever looked at your company and thought “this shouldn’t be this hard” — this newsletter is for you.
If you run a lending operation and you’re tired of buying tools that don’t move the needle. If you’re a founder who suspects the real bottleneck is the architecture, not the people. If you lead a team and the friction between your systems is louder than the work itself.
Or if you’re just curious about why companies break in ways that nobody talks about — welcome.
A bit about me
I’m Chris Grimes, founder and CEO of FundMore — an AI-native loan origination platform. We build agentic mortgage and lending infrastructure for institutional clients across Canada and the US.
I spent years watching good people fight bad systems — smart operators buried in workarounds, losing hours to problems that shouldn’t exist. The structural problems were obvious once you looked for them. But nobody was looking.
Now I am.
Let’s kill the stack.
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