Episode #553: Merging Hospitality and Real Estate: JaJa Jackson’s Blueprint for Flexible Living Success

On this episode, host Pete Moore reconnects with Jaja Jackson, a longtime friend and fellow Harvard Business School alum, for a deep dive into the intersection of real estate, hospitality, and health. Jaja shares his path from developing homes and communities, to joining Airbnb in its pivotal years, where he helped bridge the gap between multifamily housing and the (then) cutting-edge world of home sharing. Now a leader at ICONIQ Capital, Jackson discusses how his team has reimagined multifamily properties to boost net operating income and create vibrant, HALO-focused communities. (Health, Active Lifestyle, Outdoors.)

Pete and Jaja explore how many lessons from hospitality and flexible living can--and probably should--carry over into the health club industry—emphasizing the importance of relationship-building, curated experiences, and bringing on top-tier talent. They discuss the role of loneliness in today’s health crisis and offer actionable ideas for club operators, from employing inspiring staff to forming innovative partnerships with residential buildings. Jackson provides solid suggestions and practical takeaways from outside the industry that any club operator would do well to take seriously. Listen now for this fresh perspective on elevating the HALO sector.

On increasing the yield in multifamily without major renovations, Jackson states, "All you're doing is changing the operator and in some cases investing in furnishings to extend the value and the operation of your amenities in common spaces . . . that translates into an unlevered yield increase of between 1 and 5 or 6%. And it's tremendous!"

Key themes discussed

• Evolution of Airbnb and real estate partnerships.
• Creating flexible living asset classes for higher returns.
• Overcoming resistance and building trust in hospitality innovation.
• Strategies to enhance resident and member experiences.
• Importance of health, wellness, and community in living spaces.
• Leveraging talent (athletes, trainers) for cultural impact.
• Addressing loneliness and building genuine connections.

A few key takeaways: 

1. Transforming Multifamily Real Estate Through Flexible Living: Jaja shared his experience moving from "traditional" real estate development to pioneering “flexible living” while at Airbnb and now at ICONIQ Capital. By blending hospitality concepts with class A multifamily buildings, he helped create new asset value and returns, boosting net operating income by 15–40% without expensive renovations.

2. The Power of Trust and Experience in Merging Hospitality & Real Estate: Initially, the biggest hurdles were skepticism and trust issues from large apartment owners about the idea of short-term rentals. Jaja and his team addressed this by building software and policies ensuring resident safety and a trusted experience, paving the way for programs like Airbnb’s Friendly Buildings.

3. Culture and Personalization Are Game Changers in Health and Fitness: Drawing parallels to the health club space, Jaja highlights that the sector is overdue for a hospitality-like approach—moving beyond transactional relationships to foster real community and deep personalization. He suggests health clubs can learn from hospitality by knowing members’ needs, supporting their goals, and making every interaction memorable.

4. Building Community and Combating Loneliness: Both in multifamily living and health clubs, facilitating real connections is crucial. Jaja’s approach includes encouraging residents to meet each other through fitness amenities and group activities, even integrating professional athletes as resident “ambassadors” to inspire and engage. He strongly believes in addressing not just physical health, but also combating loneliness and building social connections as a core part of wellness.

5. Talent and Ownership Mindset Are Critical: Whether in property management or fitness clubs, success hinges on having the right people—those who think like owners, have charisma, and are invested for the long term. Jaja and Pete both emphasize the importance of intentional hiring (“pay for talent”) and instilling commitment, suggesting businesses treat employee recruitment and culture-building as vital investments, not afterthoughts.

The statements by Jaja are not investment advice and do not represent ICONIQ Capital or Airbnb.

Resources: 

• Jaja Jackson: https://www.linkedin.com/in/jaja-jackson-36832a57 
• Iconiq Capital: https://www.iconiqcapital.com 
• Prospect Wizard: https://www.theprospectwizard.com 
• Promotion Vault: http://www.promotionvault.com
• HigherDose: http://www.higherdose.com