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I write about how we design, build, and make decisions in the physical world — a field where success depends on navigating risk, timing, and tradeoffs.

The company had already been facing growth and revenue challenges, but CEO Adora Cheung said the “deciding factor” was the four lawsuits it was fighting over whether its workers should be classified as employees or contractors. None of them were class actions yet, but they made fundraising that much harder. The lawsuits were the nail in the coffin — Homejoy didn’t have the war chest of Uber to fight long, costly legal battles.

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