Experience is the New Asset Class - Sean Hehir - President & CEO - Trinity Investments

Nov 5, 2025

Sean Hehir, President & CEO of Trinity Investments, dives into the future of hospitality by embracing AI for operations and predictive analytics. He discusses the rise of experiential travel and its impact on hotel investments, contrasting unique experiences with commodity assets. Sean shares insights from major renovations like The Diplomat, highlighting the importance of culture and leadership in scaling a global firm. He also explores strategies for navigating joint ventures and maintaining a strong company culture amidst growth.

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ADVICE

Use AI To Free People For Relationship Work

Encourage every team member to use AI to automate grunt work and boost efficiency.
Use saved time to develop relationships and soft skills because hospitality is a people business.

INSIGHT

Make Asset Management Predictive With External Data

Combine internal P&Ls with external data like airline seats and credit-card spend to predict demand.
Predictive dashboards let you be proactive rather than reporting last month's traffic.

INSIGHT

Experiential Travel Is Reshaping Hospitality Demand

COVID shifted traveler psychology toward experiential travel that values unique experiences.
Hospitality as an asset class benefits because experiential demand is rising.

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In his return to Masters of Moments, Sean Hehir joins Jake Wurzak for a deeper dive into the future of hospitality, technology, and investment strategy. Building on their first conversation, Sean shares how his firm has embraced AI to transform operations and asset management, using data to predict market shifts and enhance efficiency across a global portfolio. He also discusses the evolving landscape of hotel investing, from luxury experiential travel to large-scale renovations, offering candid insights into leadership, culture, and the importance of partnering with the right people.

They discuss: • How AI and predictive data are reshaping hotel asset management • The rise of experiential travel and why it’s redefining hospitality investment • Strategic lessons from major hotel renovations like The Diplomat and The White Barn Inn • The balance between people, culture, and technology in scaling a global firm • The future of hospitality investment, from Europe to experiential and wellness-driven models

Links:

Sean on LinkedIn - https://www.linkedin.com/in/sean-hehir/

Trinity Investments - https://www.trinityinvestments.com/

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) - AI in business: Transforming operations
(00:04:06) - Asset management and predictive analytics
(00:05:16) - Hospitality industry trends and adaptations
(00:10:22) - Luxury vs. commodity hotels
(00:14:12) - Strategizing hotel acquisitions
(00:23:22) - Navigating challenges and maintaining culture
(00:24:54) - Capital strategy and market dynamics
(00:41:35) - Challenges of raising a first-time fund
(00:42:15) - Finding a niche in hospitality real estate
(00:43:17) - Balancing fundraising and deal focus
(00:44:40) - Sourcing deals: Marketed vs. off-market
(00:46:35) - Choosing the right partners
(00:48:16) - The Standard in London deal
(00:50:24) - Maintaining entrepreneurial culture
(00:54:39) - Biggest mistakes and wins in asset management
(00:57:40) - Impact of politics on investing strategy
(00:58:38) - Innovative renovation strategies
(01:00:52) - Exploring new opportunities in hospitality
(01:03:39) - The importance of service in luxury hotels
(01:09:12) - Future aspirations and gratitude
(01:10:35) - Favorite hotels and unique experiences