The case examines how a New York-based 10-year-old start-up, Lemonade Inc., successfully disrupted the insurance industry. Powered by artificial intelligence, Lemonade's mobile app replaced brokers and bureaucracy with bots and machine learning. The combination of simple product, no jargon, zero paperwork and an all-digital engagement allowed Lemonade to collapse costs, not at the expense of customer experience but to delight young customers with "instant everything" – from buying insurance in 90 seconds to getting claims paid in 3 seconds. Lemonade's notable milestones include surpassing $1 billion in in-force premiums in March 2025, a net loss ratio improvement from 97% in 2022 to 75% in 2025, and its first full year of positive adjusted free cash flow in 2024. Despite strong top-line growth, the company was yet to turn a profit, and its stock performance had been rocky. Lemonade posted a $202.2 million net loss in 2024, and its market capitalization stood at $4.2 billion in August 2025, significantly below its $9.8 billion peak in January 2021. Looking ahead, Lemonade aimed to increase in-force premiums tenfold, to $10 billion, by aggressively acquiring customers without significantly raising costs. As the stock regained market attention, bullish analysts highlighted ongoing progress toward profitability and improving loss ratios, whereas bearish analysts questioned the fundamentals behind the highly positive narrative presented by CEO Daniel Schreiber. A key question was whether the company could sustain its data- and AI-enabled competitive advantage or whether incumbents with deep pockets and growing technological investments would catch up. Against a backdrop of geopolitical tensions, uncertain macroeconomic conditions and increased competition, should institutional investors continue to invest in Lemonade or not?