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Practical thinking on technology strategy, engineering leadership, and building things that last.

Your First Engineering Hire Sets the Ceiling

Resumes and technical interviews won't reveal what matters most about your first engineering hire: whether they can make decisions when nobody's watching.

27 April 20266 min readRead article →

Leadership

2 posts

fractional-ctohiring

When a Fractional CTO Pays for Itself

You're already making CTO-level decisions. The question is whether you're qualified. Knowing when to hire a fractional CTO starts with that honest answer.

29 January 2026-4 min read

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fractional-cto

What Does a Fractional CTO Actually Do?

Not a part-time advisor. A fractional CTO owns technical direction, hires engineers, and ships code. The role looks nothing like what most founders expect.

15 January 2026-6 min read

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Strategy

2 posts

build-vs-buy

Build vs Buy Is Never About Cost

Cost comparisons miss the point. The real build vs buy question is whether custom code creates a competitive advantage or just makes your engineers feel clever.

26 February 2026-7 min read

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startups

Startup Technology Strategy Doesn't Start With the Stack

Stop debating React vs Vue. Early-stage technology strategy is about solving the right problem with boring tools that let you ship before the money runs out.

12 February 2026-5 min read

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Automation

5 posts

process

Every Automation You Build Is Technical Debt

That Zapier workflow you set up last year is still running. Nobody remembers how it works. Automation technical debt is the maintenance cost nobody budgets for.

22 April 2026-5 min read

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process

Stop Skipping Rungs on the Process Automation Ladder

Spreadsheets aren't the problem. The process automation mistake that burns budgets is jumping to enterprise software before you understand your own workflows.

22 April 2026-5 min read

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aibuild-vs-buy

Build vs Buy AI: Buy Until It Breaks

Off-the-shelf AI tools handle 90% of what a small business needs. Knowing when you've hit their ceiling is the real build vs buy AI automation decision.

29 March 2026-6 min read

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AI Won't Fix a Broken Process

You added AI automation to a broken workflow and wondered why everything got worse. The technology worked fine. Your process was the problem all along.

26 March 2026-4 min read

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hiring

One Question Settles the Automate vs Hire Debate

Budget for one thing: a tool or a person. Every automate vs hire article for small businesses says 'it depends.' One question makes the answer clear.

12 March 2026-6 min read

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