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Matching

2 published stories filed under Matching.

Two groups of people separated by a gap, connected by a single sturdy plank in the foreground while a large empty scaffold looms unbuilt behind
applied ai June 24, 2026 4 min read

Before You Build the Platform: The First Useful Thing AI Should Do

Early-stage teams building a matching network reach for the platform first — the dashboards, the accounts, the directory. The leverage is somewhere smaller and sooner: the one repetitive judgment call you're already making by hand.

What an early-stage matching network should automate with AI before building any platform — find the one expensive, repetitive judgment and ship that first.

Eli Wood headshot

Eli Wood

CEO, Black Flag Design

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A person at the edge of a dense web of interconnected nodes, with one illuminated path threading through the tangle and a hand selecting a single node
applied ai June 24, 2026 4 min read

Matching People to Help: Applied AI for a Messy Resource Graph

When someone needs help and the right help is buried in three hundred programs with different rules, the problem isn't a search box. It's matching across a graph nobody fully understands — and knowing which matches a human has to bless.

How applied AI navigates a sprawl of programs and eligibility rules to put people in front of the right help — and where a human still has to make the call.

Eli Wood headshot

Eli Wood

CEO, Black Flag Design

Read