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Today we're thrilled to welcome Tom O’Toole, the current Executive Director of the Kellogg's new Executive Fellows program and Clinical Professor of Marketing at Kellogg. He serves and has served on a range of public and private company boards. He is a Senior Advisor for McKinsey. He was Chief Marketing Officer and Chief Information Officer of Hyatt Hotels Corporation and Chief Marketing Officer of United Airlines and President of it's MileagePlus loyalty business during a long and successful corporate career. In this episode, Tom pulls back the curtain on the multi-billion dollar business of airline loyalty programs and shares his strategic roadmap for building a successful "portfolio life" after retiring from the C-suite. Key Topics Covered: • The Economics of Loyalty: Why United’s Mileage Plus was valued at $22B and how airline miles function as the world’s third most used currency. • Dynamic Pricing & Inventory: An inside look at how airlines engineer award availability and the shift toward rational, demand-based pricing. • The Boardroom Roadmap: Critical advice for securing public and private board seats, including why you need a two-year lead time. • Designing a Portfolio Life: How to balance board service, senior advising for firms like McKinsey, and teaching at top-tier universities like Northwestern. • Intentional Career Design: Why a post-corporate career must be an "engineered outcome" rather than an accidental retirement. Links: • Learn More About Daily Body Coach: http://www.dailybodycoach.com/navigat... • Apply to join Long Angle’s Community: https://www.longangle.com/apply-now-nw Long Angle is a private, vetted global community of accomplished entrepreneurs, executives, and professionals who have reached meaningful financial milestones and want to navigate wealth with peers who understand their challenges, opportunities, responsibilities, and ambitions. Hosted by the founders of the Long Angle community, Navigating Wealth is a podcast for founders, executives, and investor operators who have built significant wealth. Each episode features a guest with an unusual career journey and deep expertise across some aspect of the economy, investing, family, health, or lifestyle. Chapters: 00:01:36 - Welcome to Navigating Wealth: Tom O’ Toole 02:12 - Long Angle Community Discussion: Airline Reward Miles 15:25 - Learn more about Daily Body Coach 16:16 - Transitioning to a Portfolio Life 21:41 - How to Get on a Public Company Board 29:54 - Public vs. Private Boards 33:01 - Criteria for Board Membership 35:29 - Understanding Board Dynamics & Management 41:01 - Frequency of Board Member Recruitment 42:13 - Understanding Advisory & Consulting Opportunities 49:43 - Connect with Tom O’ Toole 50:30 - Apply to Join Long Angle