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Oliver Buchannon
Matt Watson

Sharing knowledge from 25 years of startup experience, including bootstrapping a 9 figure exit. I love to build cool tech products and companies.

The AI Last Mile Is Actually the First Mile

Jun 23, 2026

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4 min read

The AI Last Mile Is Actually the First Mile

Anyone can build now. The work that decides whether it sells has to come first.

Matt Watson
Matt Watson
The pattern I see managing remote teams

Jun 16, 2026

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4 min read

The pattern I see managing remote teams

The accidental mistake engineering leaders make that turns a single remote team into a divided one.

Matt Watson
Matt Watson
AI Won’t Make You a 10x Developer

Jun 9, 2026

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5 min read

AI Won’t Make You a 10x Developer

Why ownership, culture, and knowing what to build matter more than the tools you buy.

Matt Watson
Matt Watson
Developers are Turning Into AI Vampires. I’m One of Them.

Jun 2, 2026

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5 min read

Developers are Turning Into AI Vampires. I’m One of Them.

Inside the addictive, high-adrenaline loop of running AI agents, and the cost of forgetting to touch grass.

Matt Watson
Matt Watson
How Karpathy Solved the #1 AI Problem

May 26, 2026

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6 min read

How Karpathy Solved the #1 AI Problem

A 65-line text file just became the most popular repo on GitHub. The reason it worked has very little to do with code.

Matt Watson
Matt Watson
Vibe Coding Entrepreneurs Don’t Scale

May 19, 2026

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4 min read

Vibe Coding Entrepreneurs Don’t Scale

AI is a killer prototyping tool. It still can't sell your product for you.

Matt Watson
Matt Watson
AI Killed the Backlog

May 12, 2026

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5 min read

AI Killed the Backlog

What's left is the work everyone has been avoiding.

Matt Watson
Matt Watson
AI Writes 100% of the Code. You’re Still Liable for 100% of It.

May 5, 2026

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5 min read

AI Writes 100% of the Code. You’re Still Liable for 100% of It.

Microsoft’s new DELEGATE-52 research is the clearest evidence yet that “AI-generated” is not the same as “approved.” Here’s what engineering leaders should actually do about it.

Matt Watson
Matt Watson
Software Developers Are Replacing Software Engineers

Apr 28, 2026

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5 min read

Software Developers Are Replacing Software Engineers

The engineering assembly line is getting replaced

Matt Watson
Matt Watson
AI Is Replacing Engineering Tasks, Not Jobs

Apr 21, 2026

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5 min read

AI Is Replacing Engineering Tasks, Not Jobs

If your engineers only did what they were told, Claude Code already does that better.

Matt Watson
Matt Watson
The 4th Generation of AI Software Engineering Is Here

Apr 14, 2026

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5 min read

The 4th Generation of AI Software Engineering Is Here

It has been hard to keep up with AI. Let's review how it has evolved.

Matt Watson
Matt Watson
AI Exposed What Your Interview Process Already Missed

Apr 7, 2026

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4 min read

AI Exposed What Your Interview Process Already Missed

The interview process has been broken for a long time. AI exposed it.

Matt Watson
Matt Watson
What Big Companies Get Wrong (and Right) About Creative Engineering

Nov 13, 2025

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2 min read

What Big Companies Get Wrong (and Right) About Creative Engineering

You don’t scale creativity with headcount.

Matt Watson
Matt Watson
“It’s Done” Is a Lie Without Shared Understanding

Sep 18, 2025

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2 min read

“It’s Done” Is a Lie Without Shared Understanding

There’s a dangerous moment in most engineering teams.

Matt Watson
Matt Watson
The Skill That Defines Great Engineering Leaders (But Rarely Gets Taught)

Sep 11, 2025

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3 min read

The Skill That Defines Great Engineering Leaders (But Rarely Gets Taught)

When I first became a CTO, I thought my job was to be the smartest technical person in the room.

Matt Watson
Matt Watson
The MVP Mindset Is Dead. Build for Validation, Not Version One.

Sep 4, 2025

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3 min read

The MVP Mindset Is Dead. Build for Validation, Not Version One.

It’s never been faster to build software.

Matt Watson
Matt Watson
When Product Strategy Turns Into Lord of the Flies

Aug 28, 2025

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2 min read

When Product Strategy Turns Into Lord of the Flies

You’ve got smart people.

Matt Watson
Matt Watson
AI Won’t Save the 20% of Developer Time You’re Wasting on Friction

Aug 21, 2025

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3 min read

AI Won’t Save the 20% of Developer Time You’re Wasting on Friction

Every engineering leader wants their team to move faster.

Matt Watson
Matt Watson
You Can’t Hire Product Thinkers in the AI Era with Execution Interviews Alone

Aug 14, 2025

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4 min read

You Can’t Hire Product Thinkers in the AI Era with Execution Interviews Alone

When any LLM can solve your coding problem in five seconds, interviewing for “the right answer” is interviewing for the past.

Matt Watson
Matt Watson
Delegation Isn’t Done Until You Clear These 5 Hurdles

Aug 7, 2025

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2 min read

Delegation Isn’t Done Until You Clear These 5 Hurdles

Handing off tickets doesn’t buy you a good night’s sleep.

Matt Watson
Matt Watson
How I Vet a Technical Co-Founder

Jul 31, 2025

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2 min read

How I Vet a Technical Co-Founder

When a founder tells me they “just need a CTO,” my first question is which one.

Matt Watson
Matt Watson
What Kind of CTO Are You Becoming?

Jul 24, 2025

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2 min read

What Kind of CTO Are You Becoming?

Most CTOs don’t get hired into the role.

Matt Watson
Matt Watson
How to Build Feedback Loops Your Engineers Will Actually Use

Jul 17, 2025

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2 min read

How to Build Feedback Loops Your Engineers Will Actually Use

And Why Today’s the Day to Start

Matt Watson
Matt Watson
500 Hours, 20 Years: What I Learned Writing the Engineering Leadership Playbook

Jul 15, 2025

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2 min read

500 Hours, 20 Years: What I Learned Writing the Engineering Leadership Playbook

It’s here! The first copy of Product Driven!

Matt Watson
Matt Watson
When Engineers Aren’t the Bottleneck Anymore, Your Process Better Catch Up

Jul 10, 2025

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3 min read

When Engineers Aren’t the Bottleneck Anymore, Your Process Better Catch Up

We spent years trying to make engineers faster.

Matt Watson
Matt Watson
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Product Driven Newsletter

Product Driven Newsletter

Teaching tech companies and tech teams how to build better products and better teams with a product driven mindset


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