What happens when a successful attorney has not one, but two midlife crises and emerges as a leading voice in cybersecurity? Yan Ross, editor-in-chief of Cyber Defense Magazine and author of "The vCISO Playbook," shares his unconventional journey from Washington D.C. banking law to running a ranch in Arizona while protecting small businesses from cyber threats. Ross's story begins with a pivotal 1980 bank merger case that led him to abandon his D.C. life for the mountains of Utah—his first midlife reinvention. Twenty years later, another crisis pushed him to leave traditional law practice entirely, launching him into identity theft protection, privacy law, and ultimately cybersecurity consulting. Today, he runs Cyber Risk Management Associates, a veteran-owned small business, helping both for-profit and non-profit organizations navigate the existential threat of cyber attacks. The conversation reveals startling statistics: over a third of America's 32 million small businesses have suffered damaging cyber attacks in the past five years. Ross explains why traditional security measures like passwords are becoming obsolete in the age of AI, and why the human element remains the biggest vulnerability. He breaks down the security-convenience spectrum that every business must navigate and shares practical steps firms can take immediately. Beyond cybersecurity tactics, Ross offers a masterclass in career reinvention at any age. Working entirely with remote teams he's never met in person, Ross co-authored his book and built a business with less than $1,500 in cash investment, proving that passion and expertise can trump traditional business models. This episode offers both a cybersecurity wake-up call and inspiration for lawyers considering their own professional pivots.