How Institutional Capital Is Rethinking Short-Term Rentals

Short-term rentals, flexible living, and multifamily are no longer separate conversations. For institutional capital, they are converging into a single question around risk, yield, and long-term durability.

In this episode, Simon Lehmann sits down with Jaja Jackson, Senior Vice President of Real Assets at ICONIQ Capital and Corporate Development Officer at Sentral, to unpack how large-scale investors evaluate short-term rentals, midterm stays, and flexible living models.

This conversation cuts through platform narratives and focuses on underwriting logic, operational discipline, and why integration matters more than experimentation.

In this conversation, we discuss:

• Why Jaja Jackson sees STR as both an asset class and an operating strategy, depending on how risk and operations are structured.
  
• How institutional investors assess STR, mid-term stays, and unfurnished rentals through one core lens: predictable income, controlled risk, and lasting upside.
  
• Why flexible living works only when it is fully integrated into Class A multifamily operations, not treated as an add-on.
  
• What billions in deployed capital reveal about returns, and why mixed-length stay models outperform unfurnished-only strategies.
  
• How lessons from Airbnb shaped institutional thinking, and why early lease-arbitrage models broke down without deep operational integration.
  
• Why brand, transparent reporting, and operational discipline matter more to institutional capital than short-term yield spikes, drawing on perspectives from ICONIQ Capital and Sentral.

‍