Podcast

Zen and the Art of Real Estate Investing with Jonathan Greene

268: Designing and Operating a Boutique Wellness Resort with Diana Ossa and Josh Dobken

In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Diana Ossa and Josh Dobken to discuss the creation of their boutique wellness resort in Palm Springs. As a couple with a shared vision for conscious living, they transformed their dream into a real estate venture focused on wellness, sustainability, and community.

Diana and Josh talk about their approach to design and development, why they chose Palm Springs, and how they’re creating a guest experience that’s intimate, personalized, and grounded in nature. Their project isn’t just about hospitality. It’s about building something that reflects their values and lifestyle.

Jonathan explores how they approached the design process, from layout to material selection, and how they balanced the creative aspects with logistical and financial realities. They also discuss the importance of timing, trusting their instincts, and building a brand that speaks to a like-minded audience. Their story offers a firsthand look at how intentional living and real estate investment can align.

This episode is an honest and inspiring look at what it takes to create a boutique experience that blends business with purpose.

In this episode, you will hear:

Designing a resort around wellness, simplicity, and intentionality
Bringing a personal lifestyle vision to life through real estate
Prioritizing community, sustainability, and guest experience in every decision
The power of trusting intuition and moving at a deliberate pace
Lessons from shifting careers into hospitality development

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