The "Pickleball" Strategy for Independent Hotels With Dina Belon

Dina Belon is the President of Staypineapple Hotels, a boutique hospitality company headquartered in Kirkland, Washington, known for its collection of uniquely designed and guest-focused hotels in major US cities. Under her leadership, the company is expanding its third-party management and brand licensing model while helping independent hotels preserve their individuality and compete with larger brands. Dina was named one of Women We Admire's Top 50 Women Leaders in Hospitality in both 2024 and 2025 and has also been recognized by Boutique Hotelier. With more than 25 years in hospitality, she previously held roles with Marriott and Wyndham.

In this episode… Independent hotels do not beat the big brands by copying them. They win by being specific: a defined property character, a centralized back office that frees the on-property team, and public information deep enough that AI search returns them by name. Kin Sio sits down with Dina Belon, President of Staypineapple Hotels, on The Lights On Podcast to break down how that works across a nine-hotel portfolio.

Dina came up through the brand side. Design school, then hotel real estate development in the Orlando market, then construction management at Marriott, then a stretch in sustainability consulting that put her in a downtown Seattle office. She looked out the window one day at a three-story pineapple painted on the building across the way, Googled the company, found an open Director of Real Estate Assets role, and started two weeks later. She arrived planning to teach Staypineapple how to standardize and scale. It took about two years to see that the boutique model runs on the opposite logic. Brands write the SOP and then grade you against it. Staypineapple has one: do the next right thing.

Holding that line across nine hotels is the balancing act Dina calls a Venn diagram. A few things never change, including the Naked Experience bedding program, the water bottles, and the in-room coffee program. Everything else bends to the property. The University Inn in Seattle is a 1950s place in the U District that leans hard into its mid-century character, and its tagline is "a neighborhood hotel." The San Francisco property, built around 1910, carries what Dina jokes is more Carrara marble than Italy, and its tagline is "an elegant hotel." A guest who stays at one and then the other has to be told what to expect, and Dina treats that education as part of the job.

The scale comes from the back office, not the r