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Guest: Sean Hehir, CEO, Trinity Investments
Sean Hehir is CEO of Trinity Investments, a hospitality-focused real estate investment firm he has led since taking the helm in 2008. Born in Botswana to an Irish father and South African mother, he trained at hotel school in Switzerland and Cornell before joining Trinity in 1998, and steered the firm to focus exclusively on hospitality real estate soon after becoming CEO.
Under Hehir, Trinity has built a portfolio of large-format, irreplaceable resort hotels, including Miami’s East Hotel, the 1,000-room Diplomat Beach Resort, and the JW Marriott Marco Island, in partnership with brands like Hilton, Marriott, and Hyatt and mega funds that need Trinity’s hospitality expertise to deploy capital. Hehir walks through why Trinity refuses cap-rate arbitrage, how the firm underwrites counterparty risk before it underwrites price, and why he believes AI is making human hospitality more valuable, not less.
This episode was recorded on 7/21/26. Views, market conditions, and any figures or references discussed may have changed since recording and may not reflect current conditions at the time of release. Nothing in this podcast should be construed as investment, legal, or tax advice. Nothing in this episode is an offer to sell, or a solicitation of an offer to buy, any security or any interest in any fund or investment vehicle.
Key Takeaways
Trinity refuses cap-rate arbitrage, betting on operational upside instead of financial engineering.
“We don’t believe in cap rate arbitrage. We’re not saying we’re going to buy this at a seven cap and sell it for a five cap. We sold it to Blackstone for almost the exact same cap rate that we’d bought it for.”
Sean Hehir, [18:38]
New hotel supply has essentially stopped, making Trinity’s existing irreplaceable assets harder to replicate.
“It’s multifold. The great sites are just not available, and if they are, you have to go get the permits, and those are very hard to get. There’s a lot of NIMBY out there.”
Sean Hehir, [29:17]
AI can’t replace the human interaction guests want, so Trinity is doubling down on service.
“What AI cannot replicate is this human interaction.”
Sean Hehir, [30:46]
Every deal gets underwritten around counterparty risk before it gets underwritten around price.
“We only do business with people we like, in places we like, with people we trust. Because when stuff goes sideways, you’re in the trenches with those people.”
Sean Hehir, [39:47]
Trinity sticks to 4- to 4.5-star hotels because scale gives it more operating levers than ultra-luxury boutiques.
“I like the solid four to four-and-a-half star. They tend to be larger, more user-friendly, and less fickle in terms of the consumer base. We like having multiple levers to pull.”
Sean Hehir, [45:00]
