The Lo-Down
Josh Dobken and Diana Ossa managed billion-dollar architecture projects before buying a blank-slate hotel in Palm Springs, and turning it into a Vogue and Forbes-featured boutique property in under a year. In this episode of The Lo-Down, they break down exactly how they did it. With 15+ years of commercial architecture experience and 40+ short-term rentals across multiple states, Josh and Diana share the mindset, strategy, and hard lessons that took them from residential investing to boutique hotel ownership at scale. What You'll Learn: -Why they walked away from multiple deals before finding the right one -How they used a co-hosting company to prepare for hotel operations -The value-add strategy behind Terra Palm Springs -How they selected their market and defined their guest avatar -Why no deal is better than a bad deal -How their hotel earned coverage in Vogue, Forbes, and Travel + Leisure Whether you're exploring boutique hotels, STR investing, or building a path out of your W-2 — this episode is for you. Connect with Josh Dobken & Diana Osso Instagram: https://www.instagram.com/d.i.fi/ Instagram : https://www.instagram.com/terrapalmsprings/Website : https://www.terrapalmsprings.com Connect with Lorenzo Mercado: Instagram: https://www.instagram.com/lorenzo.mercado_ Website: LorenzoMercado.com | SolvarraGroup.com Listen to The Lo-Down Podcast 🎙 Apple: https://podcasts.apple.com/us/podcast/the-lodown/id1764777761🎙Spotify: https://open.spotify.com/show/1YjwXXjvFT3mqve6uMF983
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