​Cliff was raised in Camas, Washington, where he religiously played sports with his younger brother and childhood friends. Cliff is a graduate of Lewis & Clark Law School. During law school, he worked part-time at the Multnomah County District Attorney's Office. As a 3L, Cliff worked as a research assistant for the Portland personal injury law firm Kafoury & McDougal. Cliff passed the Uniform Bar Exam, scoring in the top 7th percentile in the Multistate Bar Exam section (out of 26 participating states). In the same year, Cliff applied and was hired at Knapp, O'Dell & MacPherson PLLC. With an aging attorney population, Cliff has identified “the internet” as the defining tool of his practice. Cliff performed the first electronic will signing in Washington State, on January 1, 2022, and continues to use the internet to connect with new clients.