The Kiki Founders Jack Montgomerie, Alexander Nicholson and Toby Thomas-Smith

Investment Notes: Kiki

Date Published:
August 31, 2023

We’re thrilled to have recently led Kiki’s (formerly EasyRent) latest seed round. Kiki, is a private peer-to-peer subletting club that is unlocking friendship and a new way of living. Born in Wellington, battle-hardened in Sydney, and now conquering New York City, we’re excited to back Toby, Jack and Alex as they rewrite the playbook on subletting. 

Kiki started as a university business in Auckland and later expanded to Sydney, where on AU$120K raised, it generated AU$3.5M in GMV and AU$350K in revenue. Despite being profitable, the team decided to shut down operations in Sydney to focus on launching in New York City with the belief that the global winner in this category is ultimately defined by who wins the major cities in the US. We are excited to back that ambition from the very start, armed with the learnings from Sydney.

People over Property

Tailored for short-term sublets (minimum of 1 to 3 months with an average of 6 weeks), Kiki connects people to sublet their rental home while they take extended trips away. The product is designed to leverage social ties and affinity-based matches, similar to a dating app, to help users build trust in the counterparties who cook in their kitchen, use their bathroom, and sleep in their bed. 

This approach - putting people over property - helped overcome a behavioural inertia in Sydney that saw 2/3rds of their 1,500 matches sublet their home for the first time. And then once the first listing goes well, a new way of living becomes possible. By breaking even on the cost of rent through subletting, users can travel more frequently and embrace a new lifestyle. A remarkable 48% of listings were repeat listers in the first year of Kiki being operational in Sydney. 

This approach to matching users became so successful that many friendships were formed that persist to this day. And the gratitude that users feel for unlocking both friendship and experiences has resulted in Kiki becoming a thriving global community that is evangelising this new way of living.

It is the People. It is the People. It is the People.

To paraphrase the iconic Maori proverb, the most important thing in the world is the people. Kiki puts people over property, and our investment in Kiki is a true seed bet on the founders. 

We believe that 23-year-old co-founder and CEO Toby Thomas-Smith has a unique insight into a market that is fringe now, but might turn out to be enormous. Toby is known for his unconventional tactics to drive awareness and engagement for Kiki. From an April Fools prank about being acquired by AirBnB, sleeping on Bondi Beach to raise money for the housing crisis and hustling free booze for a farewell cruise on Sydney Harbour, Toby is incredibly energetic and relentless in driving free, viral awareness of Kiki. 

The result is a "cult-like" community vibe, which is rare and difficult to replicate. 

What next?

Kiki is building its waitlist in preparation for its NYC launch and hiring its founding team members. Head to or follow them on Instagram

We’re excited to be coming along on this journey and can’t wait to see what Toby, Jack, Alex and the team accomplish.