Roger and I started Caretaker as Flip to redesign the rental housing industry so that it meets the needs of tenants as much as it does of owners. We had been renters for years, and after hundreds of frustrating experiences with unreliable property managers and overworked landlords, we began to imagine a new kind of property management company - built by software engineers and renters.

Property management, traditionally, exists to make property owners happy. We decided to take the opposite approach: in our first few years, all we did was obsess over the ideal tenant experience. In time, owners began to sign up, too. We started thinking about our ideal landlord customer and how to acquire him or her.

That's when it became painfully obvious that we had outgrown our name.

Goodbye, Flip. Hello, Caretaker.

Welcome to our rebrand. In this post I'm going to describe what our team has been building these past few years in case you're new to us. After that, I'll share a bit about why and how we chose this new name.

How we got here

There are lots of things that suck about being a renter. We started with one of the most painful experiences: that feeling when you gained a job, lost a job, fell in love, out of love and your life no longer fits with your lease. You’ll do anything to move now without covering rent in two places at once. Your landlord tells you it will cost you [insert very expensive number] to move early. Thankfully, you find Flip: our name makes perfect sense for you because "flipping your lease" feels like exactly what you want to do.

Subletting, taken care of

Perhaps shockingly, we never received any legal actions from Oprah Winfrey

We started here for two reasons. First, no one else was doing a very good job of solving this problem. There was an unmet need, which made it easier for us to acquire renters. Second, the steps required to replace oneself with a qualified subtenant are actually pretty similar to the steps that an individual landlord needs to take to get a new tenant:

  1. Get in front of the right renters. This isn't a quantity game so much as a quality game. What kinds of people want to live in X apartment and where do they congregate? Figure that out and advertise there.
  2. Find a renter who is very qualified. Screening renters is probably the hardest and most important part of operating rental housing. You can bet that a subtenant will need to be as qualified as the person they're replacing for the landlord to feel comfortable.
  3. Sign a legal document. Agreeing to let someone live in a property that you have any kind of stake in without a legal agreement would be downright foolish.
  4. Get paid rent and hold a security deposit. One side needs to pay the other side money. No one wants to have to nag anyone else. If the rent never arrives, whoever needs to be made whole should be made whole.

We built a system for handling these four steps for leaseholders. In doing so, we were also building tools that their landlords needed.

Get out of your lease, instantly

Our subletting marketplace was attracting lots of renters and making many of them pretty happy, but something bothered us. For some of our customers, the continued responsibilities associated with a sublet as opposed to a lease assignment or an outright clean break was too much stress and responsibility. They wanted a way to pay more to completely relinquish responsibility for the remaining months of their lease.

We assumed responsibility for ongoing leases so that tenants could leave early and landlords kept getting their rent

We launched a new offering called Flip Instant to give these customers what they wanted. We assumed full responsibility for the remaining months of the tenant's lease, promising their landlord that we'd pay the rent no matter what. This meant that we were now responsible for the steps mentioned above with one crucial difference: if we didn't do a good job, we lost money.

The rent tracking graph on the homepage of the Caretaker dashboard for property owners. We designed this for ourselves initially to help track if we were losing money or not.

Just as iBuyers like Zillow Offers and Opendoor require operational excellence for selling a home, we had to be exceptional at property management: placing a new tenant, making units ready for their move-in, holding them accountable for damages, collecting and transferring their rent to the owner.

"Just as iBuyers like Zillow Offers and OpenDoor require operational excellence for selling a home, we had to be exceptional at property management. If we didn't do a good job, we lost money."

The new offering for renters turned us into property managers nearly overnight.

Engineers become property managers

Our team was and still is engineering-driven. At any given point, about three-quarters of us are on the engineering and product teams. The systems we began to build around this point were more than just a little influenced by that perspective. Rather than building tools for property managers we aimed to build tools that replace property managers.

While all this work went on internally, from an outsider's perspective we were still a company that helped renters make surprise moves and embrace optionality. We were still very much Flip.

On the inside, we realized that we were developing tools for holding onto renters for as long as possible rather than encouraging them to leave! It was around this time, about 18 months after launching our Instant offering, that we began the rebranding exercise.

Why Caretaker?

There was two issues that we needed to address with our new branding. First, a new identity should evoke the right imperceptible feelings and thoughts in the heads of customers. Second, our old name had a very specific definition in the context of real estate investing and one that was the opposite of our offering. If our new identity was going to have a clear meaning (as opposed to a made up word) it should be one that explains what we do.

Flip was fleeting, Caretaker is permanent

When we were raising a seed round I remember constantly painting a picture of a fresh grad using us to find a temporary sublet for an internship, then a bachelor pad, and so on until he bought his first home. We set out to create long-term relationships with renters, but "Flip" suggests speed and impermanence - someone who might not be around tomorrow. That felt wrong.

We wanted a new identity that implied permanence and that instilled trust.

Caretaker (noun). “A person employed to look after a public building or a house in the owner's absence.”

With Caretaker (and, crucially, the .com address) we had it. Our platform consists of a suite of products that do pretty much everything an extraordinary property caretaker would do: open the door for trusted parties, coordinate maintenance issues, keep track of rent and security deposits, and allow tenants to fruitfully complain.

It says what we do (take care)

We often say that we're the only "renter first" property management company. If our company were a person the first thing he would think about in the morning and the last thing he would think about at night would be "am I doing a good enough job of taking care of my tenants?" This is a hugely important part of our DNA and we wanted that to come out in our name.

We had a feeling that the canniest rental property owners would grasp this. Early data suggested we were right:

When a new customer sent this to his tenants unprompted we knew we'd done something right

We also wanted to think far into the future in a way that we hadn't done the first time around (we didn't want to have to rebrand twice). The name could have a meaning, but not one that's so specific it may feel inappropriate in the future.

Towards more owners

Our mission is to democratize access to the housing market by making it easier to invest in and own property. We build systems that take care of properties so that investing in them becomes increasingly easier and more individuals can do it. We build systems that take care of tenants, so that they're happy where they are now and also have stepping stones towards having their own stake in the housing market.

In other words, our job is to take care of properties and of tenants, and we could work on that for a long-time before feeling like it was time for a new identity.

Welcome to Caretaker.


ABOUT THE AUTHOR

Susannah Vila is the Chief Executive Officer and co-founder of Caretaker. She is a problem solver, a writer, and an aspiring engineer.


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