This episode is a masterclass in turning pain into purpose.
Diana and Josh, two married architects, were forced to reimagine their future after losing both their fathers in 2021.
What began as a journey to escape the W-2 grind became Terra Palm Springs, the city’s first true wellness boutique hotel.
They reveal how they:
• Pivoted from flips and BRRRRs into commercial real estate
• Used their design and construction edge to underwrite with vision
• Created immersive guest experiences that transcend hospitality
• Built three synergistic businesses to scale with intention
• Took bold action while honoring their deepest personal “why”
This story will move you, inspire you, and give you a real blueprint for building a brand, and a life that matters.
What You’ll Learn:
• How to spot your unfair advantage (and actually use it)
• The key to underwriting without inflating projections
• What makes a boutique hotel truly stand out
• How to transition from short-term rentals to hotel ownership
• Why generosity is the secret weapon in hospitality
00:00 - Action drives clarity
00:35 - Process-proven growth
01:36 - Power couple feature
02:20 - Life-changing loss
05:55 - Strategic shift to scale
07:26 - Expert system builders
09:50 - Value-add obsession
10:56 - Underwrite with confidence
14:30 - Unapologetic branding
16:42 - First-of-its-kind wellness hotel
21:00 - Team-powered execution
25:40 - The real estate awakening
28:00 - Finding purpose through pain
31:30 - Create your unfair advantage
36:00 - Future-built freedom
43:00 - Hospitality secret: give generously
Guest Bio:
Diana and Josh Dobken have 15+ years of experience in the architecture and construction industries. They strategically invest in value-add opportunities where they can use their design expertise to maximize their return on investment. Additionally, Diana and Josh co-host 35+ MTRs and STRs across multiple states for other real estate investors, bringing their hospitality standards and design sensibility to each property we manage.
Beyond property investment, Diana and Josh also manage comprehensive operations teams for hotels, with them overseeing director of operations roles and guest experience management. This hands-on operational experience gives them invaluable insights into how design decisions impact day-to-day functionality and guest satisfaction.
Their most current project involves the Architectural and Interior design of Terra Palm Springs, the first wellness Boutique Hotel in Palm Springs featured in Vogue, Forbes, Hotels Above Par, and selected as part of Travel and Leisure It List of 2025’ 100 Best New Hotels in the World.
Guest Link:
http://www.instagram.com/d.i.fi
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