Susannah Vila once left an apartment above a Williamsburg restaurant after a month. A year near Union Square counted as a long stay. By 2016, her New York housing history ran to 15 apartments, enough addresses to make filling out a form feel like writing a memoir. Most people would have taken the hint and bought fewer books. Vila built a company around the possibility that the lease, rather than the person, needed to become more accommodating.
There is a particular indignity to wanting to move while a piece of paper insists you remain. A job changes, a roommate leaves, another city beckons. The rent carries on. Vila knew this mismatch from the inside. Her company, initially called Flip and later Caretaker, began with the practical question of how to let a renter leave without leaving everybody else with a problem.
Her route to that question passed through places well beyond New York real estate: digital activism, online publishing, interviews in Cairo and an organization concerned with getting useful technology into the right hands. Across those settings, a recurring concern emerges. Having a tool available means little if people cannot use it to do the thing they came to do.
A map made of temporary addresses
Vila arrived in New York as a transfer student, moving from George Washington University to New York University. Her subsequent addresses ranged across Brooklyn and Manhattan. She also spent time living and subletting in Mexico City, Peru and Cairo. This was a housing education conducted through actual doors, with the inconvenience of moving included in the tuition.
In 2016, she described having divided her time between San Francisco, New York and other cities, reaching the end of her twenties without wanting to settle in one place. She connected that experience to the growth of freelance work. People whose working lives moved around would need housing arrangements that could move with them. A twelve-month commitment could be an awkward instrument for a much shorter chapter.
That observation gave Flip a customer she understood unusually well. The departing tenant had reasons to leave. The arriving tenant needed somewhere to live. The landlord wanted a reliable occupant and rent paid on time. Between them sat a collection of checks, permissions, agreements and payments. The opportunity lay in arranging those handoffs so a change of plans could become an ordinary transaction.
Before the lease, the missing connection
Earlier in her career, Vila directed content and outreach at Movements.org, working on resources for people using digital media to organize. In 2011, her work included recruiting and training activists from more than 27 countries. She appeared in discussions about social media and the Arab uprisings, including an April radio conversation with GlobalPost co-founder Charles Sennott.
There was writing, too. She covered political satire in Tunisia and Egypt, paying attention to the jokes circulating alongside logistical information. The subject suited a larger question in her work: how people actually communicate when something matters to them. An online platform might provide the channel. The reasons to participate, and the relationships that sustained participation, required closer attention.
In the summer of 2011, she interviewed advocates in Cairo. Those conversations, together with her experience at Movements.org, helped lead her to co-found The Engine Room. The organization records her as a co-founder and community lead until 2013. Its other founders include Alix Dunn and Christopher Wilson.
Her 2012 account of the Social Tech Census described a frustrating disconnect. Organizations had produced guides and other resources, but the people who could benefit did not necessarily encounter them. Visiting trainers could arrive for a short workshop and disappear again. Local needs were insufficiently understood. Vila wanted to connect available support with the people seeking it, including support already close to home.
She also questioned the expectation that a technology maker should solve every strategic problem surrounding its product. Writing about crowdsourced maps, she separated launching a map from persuading people to contribute and turning their contributions into useful action. That distinction matters in her later housing work: posting an apartment is only the beginning of getting somebody safely moved in.
What happens after someone finds the tool?
The apartment listing had unfinished business
Vila founded Flip while in graduate school and developed it through Techstars in New York. She is a 2015 Columbia Business School alumna. When the marketplace launched in December 2015, it had roughly 300 available leases. The proposition was concrete: connect a leaseholder who wanted to leave with a qualified person who wanted to take over.
Even the pricing reflected the departing renter’s circumstances. Someone with a desirable lease could ask to be paid for it. Someone in a hurry could offer a reward to the person taking it off their hands. A lease could carry value in either direction. The software had to accommodate the person who saw an opportunity and the person watching the calendar with increasing alarm.
By May 2016, Flip had more than 1,500 leases posted and over 300 transferred. It joined MetaProp NYC’s accelerator as the anchor of its 2016 class. Vila described a pilot partnership with TF Cornerstone, bringing the idea into contact with the landlords whose cooperation would help make it work.
“We want to create a more flexible way of leasing property.”
Susannah Vila
The operational details explain why the idea required more than a classified ad. By 2017, Flip connected a prospective renter’s financial and employment information to a profile, helped produce a sublease, handled payments through escrow and made it easier to request the landlord’s permission. It also allowed a bounty for helping find a subtenant. An introduction had become a sequence of tasks with money and trust attached.
The people around the idea
Vila’s early business developed through several New York startup communities: Columbia Startup Lab, Techstars and MetaProp. By August 2017, Flip had received a new $2.2 million investment following an earlier $1.2 million in angel financing. It was serving New York renters while testing in San Francisco, Los Angeles and Boston.
Joanne Wilson, the investor known as Gotham Gal, was an early angel backer. Union Square Ventures subsequently invested. In January 2019, Fred Wilson highlighted Vila’s conversation on Joanne’s podcast, recommending her account of where the idea came from and how she was building the company. The relationships place Flip within a recognizable startup network, but Vila’s interviews remained close to the tenant’s immediate predicament.
Asked in March 2016 what excited her, she pointed to users earning money through Flip the previous month. Asked about a cause, she spoke about making entrepreneurship easier to enter. Starting projects had brought her pleasure and difficulty, and she wanted fewer barriers for others. She described building as a personal experience, with all its unevenness intact.
A name with a longer tenancy
With co-founder Roger Graham, Vila broadened the company’s work beyond helping renters replace themselves. Flip Instant took responsibility for the remaining lease, committing to pay the landlord even while finding the next occupant. The company now had a direct financial interest in making every handoff work. Its own tools became part of running the properties.
By her July 2021 account, owners were becoming customers, too. The same sequence that helped a departing tenant could help a landlord find and keep a renter. The name Flip had begun to suggest the wrong time horizon. Vila wanted an identity that conveyed continuity. Caretaker described the ongoing work of attending to a property and the people living there.
The naming process had an unusually practical starting point: available, reasonably priced .com domains. The team narrowed that list to names that suited its purpose. The Caretaker.com purchase cost $112,000. Vila judged the expense against the market the identity could help the company reach, and described landlords beginning to use language about taking care of tenants when introducing the service.
“We aim to expand access to rental housing.”
Susannah Vila, on Caretaker’s purpose
Still interested in what gets overlooked
Some of Vila’s later writing concerns the unglamorous details that make a service usable. In February 2021, she described improvements to the way Caretaker explained rent payouts. Receiving money from several tenants had made the reporting difficult to follow. Fixing the communication was part of doing the job. A payment can arrive correctly and still leave somebody wondering what happened.
In April 2024, she turned to the records behind a house. Her article argued that historical property documents could reveal how repairs and improvements had happened over time, using a South Florida home as an example. The interest had shifted from the handover to the history, but the attention to information a person might otherwise miss remained familiar.
Her Caretaker biography described her as a writer, problem solver and aspiring engineer. The last phrase leaves room for learning; it also fits a career spent moving between understanding a difficulty and working out how to address it. From training resources to subleases to a confusing rent statement, her subjects have often been the places where a promising idea meets somebody’s actual day.
The early apartment history makes for an amusing introduction. Its lasting value is more practical. Vila took seriously the renter who wanted to leave and the owner who needed someone to stay. Building around both required her company to become more settled than its original name suggested. After so much moving, she chose a word for looking after a place.