Writing / Subject
Operational software
Enterprise systems, exception-heavy workflows, integrations and the handoffs between them.
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The first question in any outage: whose system is it?
Most production failures in integrated systems aren't yours or theirs. They're the handoff between the two, and that's exactly where nobody looks first.
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Build versus buy is really a question about who owns the interface
The standard framing — compare the cost of building to the cost of buying — misses the question that actually decides it: does the vendor's product expose the interface you need, or just the outcome?
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How enterprise buyers evaluate operational risk
Founders assume buyers are evaluating the product. They're also evaluating what happens when it fails. Why an inferior incumbent keeps winning, and how to sell controlled change instead of pure improvement.
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When services are a wedge — and when they become a trap
Services can be the only credible way into a complex industry, or the thing that caps your margins forever. The distinction isn't whether humans are involved. It's whether their effort compounds.
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Why enterprise software fails at exception handling
Enterprise software is designed around states. Real operations happen between them. Why systems fail at the moment users most need help — and the four capabilities good exception handling requires.
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Building when one customer dominates the business
Concentration isn't the real risk — failing to convert a dominant customer into reusable product is. The metric that matters isn't percentage of revenue. It's percentage of the business that could transfer to another customer.
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Company-Building Under Real Constraints
A seven-part series on building operational software companies — customer concentration, automation, exception handling, services, enterprise risk, and what exits do and don't teach. Written from the operator's chair, not the slide deck.