On this episode, Kevin chats with Bill Vanderstraaten, President and founder of Chief Partners, a Dallas-based family office that invests LP equity into commercial real estate as part of the Trever Rees-Jones holdings. With a team of just 6 professionals typically investing $5MM to $15MM per deal, they manage about $1.2B across 80 assets with 30 GP operating partners and have built over 8MM square feet of commercial space since 2007. The conversation explores how family offices differ from opportunity funds, why holding too long is a common mistake family office investors make, and how culture and integrity are central to Chief's underwriting of potential operating partners. Bill discusses where flexibility shows as a competitive advantage for family office equity, the merit of providing investors an earnest assessment of risk, and why Chief sees itself as more than commodity capital. They cover the value of curiosity in leveling up skills, why people remain at the heart of real estate due to the high degree of trust required, what a high idle brings to your career, and how a sailing analogy applies to the challenge of being an entrepreneur.