Dimitri Masin, Douglas Squirrel, Jason Smith | Office Hours #743

Dimitri Masin Dimitri Masin is an AI expert with a strong background in finance, compliance, and risk management. As the former VP of Data Science for Financial Crime and Fraud at Monzo, one of the UK’s leading challenger banks, he led efforts to combat fraud using advanced AI techniques. Prior to that, he worked as a Sales Finance Analyst at Google, giving him a unique perspective at the intersection of big tech and financial services. Dimitri is known for his ability to uncover black-box risks and regulatory blind spots, making him a sought-after voice in responsible AI adoption. Now the CEO of Gradient Labs, Dimitri is focused on building secure and compliant AI systems for highly regulated industries. His company developed the first safe AI customer service agent specifically tailored for sectors with strict compliance requirements. Douglas Squirrel Douglas Squirrel is a veteran technologist with four decades of coding experience and over twenty years leading software teams. As a former CTO in diverse startups—from fintech and biotech to music—he’s known for driving significant productivity improvements through the power of effective conversations. Squirrel has worked with more than 300 organizations across the globe, helping them transform product strategies, technical capabilities, and company culture by fostering alignment, productive conflict, and business-focused communication. In addition to his hands-on leadership and consulting work, Squirrel is a published author and thought leader. Jason Smith Jason Smith is the Founder and CEO of Clarity 2 Prosperity, Prosperity Capital Advisors (with over $3.4 billion in assets under management), and JL Smith Holistic Wealth Management. As a best-selling author, speaker, and entrepreneur, he has dedicated his career to empowering financial advisors across the country. His companies help advisors streamline their practices, grow their businesses, and educate clients with holistic financial planning strategies. Jason is the author of The Bucket Plan, a widely adopted approach to securing retirement, and The Rainmaker Multiplier, which outlines his proven methods for transforming advisory firms into scalable, self-sustaining businesses.