Essays
Essays on AI agents and the systems around them.
Where agents help, where they fail, what has to sit around the model, and what building companies taught me about all three.
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An AI task is not done until the world has changed
I moved my working life onto AI agents and logged every failure. Each one traced to the same cause: the to-do item is the wrong primitive for a machine.
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PillWatch: 99 percent accurate, wrong every fifth box
Four high schoolers, a $60 Raspberry Pi, and the compounding math that turns 99 percent per cell into an error every fifth box.
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1,029 cells: what small, honest data teaches about AI
The PillWatch team labels its own data, splits it by photograph, and hunts its rare cases deliberately. That discipline taught more than model tuning did.
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The LLM call you can delete
631 replayed decisions, six written rules, zero disagreements. The model I was paying to route my email lost to the policy file it was reading.
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Pivot gates
How founders can distinguish a slow strategy from a broken premise before sunk cost makes the decision for them.
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Routing optimization isn't a shortest-path problem
The hard part of flight routing was never finding the cheapest itinerary. It's that 'cheapest' and 'best' are different questions, and one of them is a hard rule while the other is a matter of taste.
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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, comparing 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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What successful exits do and do not teach you
An exit gives a founder credibility, not certainty. What building and selling companies actually teaches, and why a previous exit can quietly become a liability.
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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 what good exception handling requires.
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Manual minutes per transaction is better than "AI adoption"
"AI adoption" is one of the least useful metrics in software. Manual minutes per transaction is hard to fake, captures hidden labor, and separates adopting AI from actually improving operations.
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Knowing whether a workflow is actually automatable
Every workflow looks automatable from a distance. Up close it's a sequence of judgments, not clicks. Five questions to ask before you automate anything, and why the process that works 80 percent of the time is the most dangerous kind.
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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.
Archive
The original tarun.me blog, from 2009.
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Why web designers are over-rated
Wired did a competition inviting designers to improve craigslist .
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when good people resign (to join you)
You make an offer to an A+ player at a big company, they accept — and then their employer rolls out the red carpet to keep them. Mark Suster calls it the counter-offer, and it's an all too familiar phenomenon worth planning for before you extend the offer.
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2 things every good startup needs
Robert Scoble has a great article today on his take on mistakes startups make .