Carrying on a Family Hospitality Newsletter Legacy

I grew up in a prominent hotel family, it's why I write The Upgrade today

🗝️A Personal Note on Why I Write This Newsletter

The reason I started writing “The Upgrade” is because my father, Richard Kelley, wrote a weekly newsletter about the hospitality industry called “The Saturday Briefing” for 40 years. He passed away four years ago, and as the resident writer in our family, I decided to carry on his legacy.

His archive of articles is a fascinating look into past and present of travel, and I’m going to share articles with paid subscribers on occasion.

My dad and me in Cambodia

Coming full circle, my dad was honored by Travel Weekly with a Lifetime Achievement Award in 2014, along with Geoffrey Kent of Abercrombie & Kent.

I met Emma Weissman, Senior Features Editor for Travel Weekly, at the Wave Awards last year when I was a guest of Outrigger Hotels at the event. Both of us grew up in the industry, and she asked me to be a guest on her Humans of Travel podcast from TravelAge West.

I grew up in a Hawaii hospitality family. My grandfather, Roy Kelley, built Outrigger Hotels from the ground up, and my father, aunts, sister, brother, and brother-in-law grew it into the multi-national hotel corporation it became by the time we sold the company in 2016. During summers in high school and college, I worked internships in front-line operations departments such as housekeeping, front desk, maintenance, and bell.

I was often one of the first readers of my dad’s “Saturday Briefing” drafts. I learned about REVPAR and EBITDA from diagrams on cocktail napkins at family dinners.

In this podcast episode, I talk about what it was like growing up around that world and what Outrigger’s presence meant for Hawaii’s tourism landscape. I also touch on the story behind launching Alpenglow Travel, lessons from a career that started in a luxury destination club running their experiential travel department, and evolved into building a boutique luxury travel agency.

I watched my dad wake up at 4am every week to draft and edit “The Saturday Briefing.” It went out every week without fail. He had such an impact on the tourism industry, and on me, that I hope to carry his legacy forward.

My dad’s book, “Paddling the Outrigger,” is a collection of Saturday Briefings with context and photos around them.