The Frankenstein Stack is Failing CTOs - Here's What Comes Next

Let's Solve the Top CTO/CPO Problems Once and For All

👋 Hello Tech Leaders!

I’m building strategic, management-level tools that only elite CTOs & CPOs have access to & I need your help to decide what to build next.

Why I’m Doing This

After 20 years I realized there’s no finish line in the CTO job, just more complex problems to solve, with higher stakes and more difficult deadlines.

But there are a handful of common problems that every CTO deals with.

And for the last 2 decades, I’ve seen the same challenges pop up across startups, scale-ups, Private Equity rollups, and enterprise turnarounds.

It’s the same set of traps every time:

• Project estimations are notoriously difficult to make accurately

• Build vs. buy is a constant question from CEOs / Boards and answers are rarely easy

• Cloud costs continue to spiral out of control for every CTO

• Technical debt strangles both velocity and engineering morale

• And demand always outpaces the dev teams actual capacity

The Frankenstein Stack

Most CTOs try to solve for these issues by creating “The Frankenstein Stack.”

This is a bunch of tools like JIRA, custom spreadsheets, random best practices, various micro-techniques and one-off dashboards duct-taped together.

But it never quite works and instead CTOs end up with:

• Different competing philosophies

• Techniques that differ from one team to the next

• Metrics that don’t match up

• Data that’s incomplete

• Arguing over whose approach is correct

That’s part of why every CTO still has these problems even after 20+ years of modern product-engineering.

Let’s look at a couple examples:

Making Project Estimations

Even with the smartest engineers for 90% of product & dev teams making an accurate project estimate is still SUPER challenging.

We run around in circles trying to figure out what the requirements mean, capturing all the dependencies, who’s going to do what, only for all of it to be wrong in the end.

You know the feeling: the Board asks you how long something will take and you give them an answer knowing you could be way, way off.

Every product & engineering leader goes bananas tinkering with story-point estimations and resource allocations but being off on delivery dates by 30% to 40% is the norm.

That kills all the trust from the business side.

Think about it like this: your company can depend on Sales, HR and Finance, but they can’t depend on Product & Engineering being accurate with their delivery dates.

Not a great look.

But this is a solvable problem with the right frameworks. In fact, the elite (10%) of companies use these frameworks to absolutely nail their delivery dates — I’m talking 90%+ accuracy.

Elite companies don’t share their frameworks but that’s what most CTOs need: a structured and methodical approach that factors everything in in the right way.

Build vs. Buy

Another trap that shows up over and over again (and can cost you millions) is the build vs. buy decision.

It seems simple: should we build this ourselves or buy something off the shelf?

But for most CTOs, this turns into a never-ending internal debate with no clear answer.

You’ve got teams that love to build, CEOs pushing for speed, and vendors promising the world — and somehow you’re stuck in the middle trying to make the right call.

Here’s what happens without a solid decision framework:

• You waste 6 months building something you could’ve bought in 6 days

• You buy a tool that doesn’t fit your stack and causes more friction

• You end up with half-built internal tools no one maintains

• Or worse — you do both and waste time and money twice

This is a decision that should feel strategic and repeatable, but for most organizations it’s chaotic and totally case-by-case.

Just like estimations, the top-performing companies solve this by utilizing the right framework not running some kind of guessing game.

They know exactly what types of problems they always build for. They know what categories they’ll never build for. And they’ve got a clear rubric to evaluate everything in between.

I’m Excited To Announce…

After 20+ years in technology leadership I want to finally solve these problems once and for all.

I’m building framework-based tools that will help CTOs with all of these challenges.

But this project is only for strategic thinkers who see the long game.

That’s why I want you involved.

You can start by telling me what you need most.