About Us

$100M For Affordable Housing

Our team has received commitments for more than $100M in private funding for Hosts to Homeowners projects in Hawaii.  We are actively looking for host families who are interested in participating in our program to become home owners.

Our goal is to install 50 families into vacation rental properties in the next three years.   If you are interested in the program, apply now.

We are also searching for properties with locations, layouts and square footage sufficient for conversion into Host to Homeowners vacation rental properties.  Properties that fit this description are in desirable locations, have easily segmented floorplans and are greater than 2,500 sq-ft.

If you have a property for sale that might work, please reach out.


Our team is lead by serial entrepreneurs with more than a decade of experience in the vacation rental industry.  Over the past 20 years Joshua Montgomery and Kris Adair have built successful businesses in telecommunications, artificial intelligence and real estate. 

Joshua and Kris are alumni of three of the most prestigious startup accelerators in the world Techstars, 500 Startups and Mass Challenge.  Their last company, Mycroft AI, raised more than $6M in Venture Capital and became a global presence in the highly competitive Voice Assistant market.

Their projects have been featured in ForbesWired, Ars Technica, Popular Science, the Washington PostLe Monde and dozens of others

Joshua is a CEO and Air Force veteran who spent his career working in joint forces environments with the national security community to better secure US Military systems.  Among his many achievements he was tapped to teach systems thinking at the US Army War College. 

Kris is an accomplished financial professional with experience managing budgets exceeding $1B and more than 1,700 staff members.  She has also been instrumental in developing and implementing marketing and communications teams with global reach.


Our Core Principles

Core Values

Honesty – Speaking truthfully about our group, goals and the impact our industry has on Hawai’i.

Integrity – Not just speaking, but behaving in a manner consistent with our values.

Transparency – Disclosing who we are, what we stand for and how we operate.