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:
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How the best hotel companies earned loyalty by prioritizing staff during COVID
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Lessons from KSL on underwriting, capital planning, and long-term investing
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The rise of experiential and independent resorts—and where they see opportunity
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Why owner-operator models outperform in today’s capital environment
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The critical role of KPIs like labor margin, guest satisfaction, and revenue flow
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Designing phantom ownership structures to retain and reward top hotel talent
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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
