Metromile Inc

Metromile merged with INSU Acquisition Corp II in February 2021. The company offered pay-per-mile car insurance using a plug-in device to track driving. Chamath Palihapitiya was an early investor. The concept was appealing — why pay flat insurance rates if you barely drive? But customer acquisition was expensive, claims processing messy, and growth painfully slow. Lemonade acquired Metromile in July 2022 for ~$500M in Lemonade stock — which itself crashed 80%. Investors who held through the acquisition saw their Metromile shares converted to Lemonade shares worth almost nothing.