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 room count. Staypineapple owns six of its hotels and manages three, and the home office runs both exactly the same way: centralized HR, accounting, sales, revenue management, marketing, and distribution. Everything except guest service sits off property, which leaves the general manager and the hotel team on team member and guest experience and nothing else. That is also the argument against signing with a big brand. Dina's advice to any owner weighing one is to read the agreement in detail before signing, because the headline number is rarely the real number. A brand may quote a 12% fee, and once the additions stack up, 20% of revenue is going to the brand. Staypineapple runs hotels from 56 rooms to 152, roughly 75% transient, and Dina says its fees come in far more reasonable than that.

The part Dina is most urgent about is AI search. Her argument is that the OTAs, at their scale, will never hold the depth of knowledge an AI needs when a traveler asks for a quirky boutique hotel near the Loop in Chicago with a restaurant. Independents do hold it. But it only pays off if the information is public and consistent in every place a model looks, from the hotel website to social media to Reddit to Wikipedia, because inconsistency is what an LLM discounts. The deeper and more consistent the record, she says, the more often you get returned. She also thinks the clock is running: Marriott, Hilton, IHG, Hyatt, Choice, Booking.com and Expedia are already in a pilot program with Google