In this episode of Masters of Moments, host Jake Wurzak sits down with Greg Kennealey, CEO of Peregrine Hospitality, for an in-depth conversation on building and operating a diversified hotel platform with a focus on performance, alignment, and long-term value creation. With a career that includes time at Strategic Hotels and KSL Capital, Greg brings both institutional experience and an owner-operator mindset to the conversation. They discuss the evolving landscape of hotel investment, from pandemic-driven shifts in demand and staffing, to the renewed importance of leisure travel, stress-testing models, and driving performance across both luxury resorts and extended-stay properties. Greg also breaks down the founding of Peregrine, their vertically integrated approach, and how alignment and talent are central to outperforming in any market cycle. They also cover: How the best hotel companies earned loyalty by prioritizing staff during COVID Lessons from KSL on underwriting, capital planning, and long-term investing The rise of experiential and independent resorts—and where they see opportunity Why owner-operator models outperform in today’s capital environment The critical role of KPIs like labor margin, guest satisfaction, and revenue flow Designing phantom ownership structures to retain and reward top hotel talent Building a culture of accountability and innovation from the ground up This episode is a masterclass in hospitality execution, told through the lens of someone who has scaled both iconic resorts and margin-driven select-service portfolios—and believes the best teams win every time. Links: Peregrine Hospitality - https://www.peregrinehg.com/ Greg on LinkedIn - https://www.linkedin.com/in/greg-kennealey-946b715/ Connect & Invest with Jake: Follow Jake on X: https://x.com/JWurzak 1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo Topics: (00:00:00) - Intro (00:01:32) - Resilience and Challenges in the Hotel Industry (00:03:12) - Investment Strategies and Stress Testing (00:04:59) - Balancing Leisure and Corporate Travel (00:08:21) - Operational Challenges and Innovations (00:34:13) - The Role of Location in Hotel Success (00:38:51) - Conviction in Hotel Investments (00:41:07) - The Complexity of Hotel Ownership (00:41:48) - The Owner-Operator Model (00:44:49) - Sales Strategies and Exit Timing (00:47:21) - Rapid Acquisition Challenges (00:50:12) - Building an Entrepreneurial Venture (00:54:24) - Operational Oversight and KPIs (00:58:40) - Managing Labor Costs (01:01:26) - Investing in Experiential Resorts (01:09:02) - Food and Beverage Strategies (01:15:52) - Future Goals and Favorite Hotels