A conversation with Coalition Inc. CEO Joshua Motta explores the ransomware landscape through the lens of cyber insurance claims data. Key insights include: ransomware severity peaked in early 2020 and has slightly declined since, though average ransom demands doubled in 2020; threat actors now target large enterprises with over $1B in revenue using account-based targeting lists; the Colonial Pipeline incident caused more economic damage through consumer panic than actual supply disruption. Basic preventive measures recommended include security awareness training, phishing simulations, closing RDP ports, and auditing access permissions. The ransomware business model has evolved from single-machine encryption to full network compromise, backup targeting, and data exfiltration for double extortion.