A 30 Year Hotel Broker Shares His Boutique Hotel Playbook and Why! | Oliver Shah E442

Experience matters—especially in a business where cycles, ego, and bad underwriting quietly destroy capital.

Rich Somers sits down with Oliver Shah, a hotel broker with more than 30 years in the hospitality industry, to break down what actually works in boutique hotels—and why most people underestimate the complexity behind them. Drawing from decades of transactions, Oliver shares how the best operators think differently about location, asset selection, operations, and long-term value creation.

The conversation dives into what separates a strong boutique hotel from a lifestyle project, how to underwrite hotels realistically, and why operational discipline matters more than aesthetic upgrades. Oliver explains where investors get misled, how trends come and go, and why experience across multiple cycles changes the way you evaluate risk and opportunity.

Rich and Oliver also explore the realities of hotel brokerage, the mistakes first-time buyers consistently make, and why patience, structure, and operator alignment matter more than chasing “sexy” deals. This episode pulls back the curtain on the unglamorous decisions that ultimately determine whether a boutique hotel thrives or struggles.

This is a practical, experience-backed conversation for investors and operators who want to understand hospitality beyond the highlight reel—and build something that actually works over the long term.

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