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My blog posts on Technical Leadership

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Technical due diligence red flags every investor should know
Startup Strategy

Technical due diligence red flags every investor should know

Avoid costly technical surprises in your startup investments. Learn the critical red flags and warning signs that experienced investors look for during technical due diligence, with practical frameworks for evaluating engineering teams, architecture decisions, and technical debt risks.

Oct 24, 2025 Read More
Why your best engineer makes a terrible technical lead
Technical Leadership

Why your best engineer makes a terrible technical lead

Promoting your strongest individual contributor to technical lead often backfires spectacularly. Here's why technical excellence doesn't predict leadership success, and how to identify engineers who can actually lead teams effectively.

Oct 14, 2025 Read More
Managing technical consultants without getting burned: a founder's guide
Technical Leadership

Managing technical consultants without getting burned: a founder's guide

Technical consultants can deliver incredible value or become expensive disasters. Here's how non-technical founders can evaluate, manage, and get real results from external technical teams without getting burned by poor work or inflated costs.

Oct 7, 2025 Read More
When AI coding assistants almost destroyed production: the AWS CDK disaster I prevented
Technical Leadership

When AI coding assistants almost destroyed production: the AWS CDK disaster I prevented

An AI coding assistant suggested "fixing" a deployment error by modifying a production stack, which would have wiped all production data on the next destroy. Here's why trusting AI with infrastructure code without understanding the implications is extremely dangerous.

Oct 3, 2025 Read More
When your technical co-founder becomes a bottleneck: navigating founder conflicts
Technical Leadership

When your technical co-founder becomes a bottleneck: navigating founder conflicts

Your technical co-founder was once your startup's superpower, but now they're blocking every decision and slowing development. Here's how to address co-founder conflicts before they destroy your company.

Sep 29, 2025 Read More
The hidden cost of cheap developers: why offshore teams need senior oversight
Technical Leadership

The hidden cost of cheap developers: why offshore teams need senior oversight

Offshore development can save money upfront, but without senior technical oversight, you'll pay far more fixing poor code quality, security vulnerabilities, and architectural disasters. Here's how to make offshore teams successful.

Sep 26, 2025 Read More
AI coding tools: senior developer superpower or junior developer trap?
Technical Leadership

AI coding tools: senior developer superpower or junior developer trap?

AI coding assistants can dramatically accelerate experienced developers, but they're creating a generation of "vibe coders" who can't distinguish good code from disasters. Here's why you need senior technical leadership to harness AI effectively.

Sep 24, 2025 Read More
The first 90 days: a CTO's guide to inheriting a messy codebase
Technical Leadership

The first 90 days: a CTO's guide to inheriting a messy codebase

Joining as CTO to find technical chaos? Here's your battle-tested 90-day framework for assessment, quick wins, and long-term strategy from someone who's cleaned up dozens of codebases over 20 years.

Aug 22, 2025 Read More
When your startup needs a technical co-founder (and what to do when you can't find one)
Startup Strategy

When your startup needs a technical co-founder (and what to do when you can't find one)

As a CTO coach with 20 years in tech leadership, I've seen countless startups struggle with this decision. Here are the clear signs and practical alternatives when technical co-founder search fails.

Jul 18, 2025 Read More
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Antonio Angelino

Startup CTO & Tech Leadership Coach
I help founders and tech leads scale engineering teams without the stress.

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