Blackbird-backed Kiki’s cofounder is now rebuilding the short-term rental startup one coffee at a time

- April 17, 2024 3 MIN READ
Toby Thomas-Smith and the startup's 6th , Caitlin Emiko
Kiki cofounder Toby Thomas-Smith and the startup's 6th employee, Caitlin Emiko. Source: Kiki.nyc/Instagram
The New York-based cofounder of New Zealand subletting startup Kiki, Toby Thomas-Smith, is blunt in his own performance assessment.

“When we launched Kiki.nyc last year I fucked up,” he’s written on LinkedIn, after the business shuttered its New York launch after 3 months, only to revive it late last month amid controversy over plans to launch a “girls only club” called Girls Who NYC in the Big Apple.

“We raised a big round, had big goals and tried to hit those as fast as possible but ended up sacrificing quality along the way,” Thomas-Smith wrote.

While posting photos outside Airbnb, claiming his startup had more properties for rent – 244 –  than the $100bn accomodation app, Kiki 1.0 achieved 100 properties sublet over 3 months.  Thomas-Smith said in January when rationalising shutting it down for the club pivot, that the business lacked the growth trajectory of the former Sydney roll out and New Yorker were not making friends the way they did in the NSW capital.

Kiki raised a A$9.5 million Seed round in August 2023, led by Blackbird, which tipped in $7 million.

The startup sublets accomodation – short-term leases for a minimum of 1 to 3 months with an average of 6 weeks.

The blue chip cap table included former Airbnb exec Harry Uffindell, Facebook Marketplace founder Bowen Pan, former Bumble exec Michelle Battersby, and Phase One Ventures founder Mahesh Muralidhar, as well as former-Uber execs Tyler Trerotola and Jaikumar Ganesh, among others.

But the “girls club” concept from an all-male team of five sparked a major debate around VC funding for women at the start of 2024.

The startup has built its brand with social media stunts and this one kicked a hornet’s nest across social channels.

One Kiki investor responded to Kiki’s posts saying they should “consider giving the money back”.

The vehemence of the reaction led Blackbird to say that both the startup and VC “recognise that Kiki’s recent social media post announcing its intention to build Girls Club NYC has regrettably caused frustration and in some cases, offence. The team understands the reaction this has caused and has taken on board all feedback.”

Coffee club

And in February, Thomas-Smith announced the return of Kiki’s subletting app, which kicked off a month ago on March 18, going from an invitation-only app to meeting prospective customers either over coffee or via FaceTime. Scaling that will no doubt be the startup’s next challenge.

“We relaunched a few weeks ago with a very different approach, you can only use Kiki if you meet me or the team for a coffee /FaceTime (yes every single person),” he wrote.

“I’ve had almost 50 coffees and it’s been honestly unbelievable. No one’s tackled the problem before like this and people are blown away. It sounds crazy but I believe we can keep doing this for a year…(hire chief coffee officers ).”

Thomas-Smith goes on to celebrate hitting 10 matches – so a 20% conversation rate on the coffee meets/Facetimes, which has generated $2,500 in revenue for 327 nights booked.

A coffee in New York costs around $5 now, so assuming the Kiki team went dutch on the drinks, and it was half of the 50 prospect meetings, the cost was around $125, so 5% of revenue.

If enthusiasm and optimism are worth their price in gold, then Thomas-Smith is richer than Elon Musk.

This is “the beginning of Kiki’s intense fire in NYC,” he wrote.

“I thought I already knew this but more users is not better! I can’t reinforce this enough. As [US VC Benchmark partner] Sarah Tavel preaches chase “happy GMV” (which means all your users have to love it or you screwed up).

“Hopefully next time you see the map it will be covered head to toe with thousands of very happy faces ”

Kiki investors no doubt share that hope.

After starting life as EasyRent in October 2018, the business rebranded as Kiki Club last October to launch in New York following the $9.5m raise last August.

Operations in Sydney closed in early 2023, after a 12-month foray, having generated $350,000 in revenue over the year, which the startup said made it profitable. The original Kiwi business closed for the move to Sydney. It’s now all-or-nothing in the Big Apple.

Early stage Spotify content contributor Frank Sinatra summed things up best when he declared: “I’m gonna make a brand new start of it in old New York, and if I can make it there, I’m gonna make it anywhere. It’s up to you New York, New York.”
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