Medical Examiner Fetches New Paws-ibilities With Pet Sitting Hustle

This transcript was generated from the episode audio and may contain minor errors.

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Happy post-boxing day. Let's talk about the latest news in dog sitting. That's right, what's up folks? It's Chris Guillebeau with side hustle school. A little throwback to episode 17, way, way, way back in the day.

That episode was called Airbnb for Dog Owners. Woman hosts pets at home for $200 a day. Well, that woman that we featured way back then, Andrea Hajjal has now cared for thousands of dogs. Yes, thousands. She's cared for those dogs and been paid for those dogs.

She's actually now earning a good full-time income from it. And that's not all. Today I have another story for you featuring a side hustler turned professional dog sitting success. This one featuring a former doctor who now lives for free in New York City. That's right, I did say lives for free in New York City, saving the majority of her income all because of pet sitting.

It's a pretty crazy story and both of these stories, the one I mentioned from episode 17 and today's, both of them are enabled by the platform Rover, or Rover.com, which now operates in 10,000 cities and recently took in a $155 million round of funding. If you had ever thought that an Airbnb for Dogs pet sitting platform would one day raise $155 million in investment money, well, you are much better than me because going back a few years, I never would have saw that coming. But here we are, we live in the future. So roll over and fetch yourself a coffee. The story begins in 30 seconds.

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Jen Singh's Rent Free Living is made possible by busy New Yorkers and their pets. Originally a burnout physician from Seattle, Jen has now called New York City home for the past three years just by living in other people's houses and taking care of their pets while they're away. This is all thanks to one app, one platform, a love of animals and a desire to earn extra money. It starts a while back. Jen had pets for most of her life.

When she wasn't rescuing small dogs, she was saving them from puppy mills or giving foster dogs a loving home. When she stumbled upon Rover, that app that offers on-demand dog walking as well as pet sitting and other pet related services, she saw the opportunity to get paid doing what she loved, hanging out with furry four-legged friends. So to supplement her income as a medical examiner, Jen signed up as a freelance dog walker and pet sitter on Rover. It was simple. One afternoon with a cup of coffee in hand, Jen created her Rover profile.

Because she had lots of experience with pets, she set her rate at $45 an hour. At first, the request trickled in slowly, but that was all she needed to get started. After some time, she began to gather five-star reviews and eventually referrals to other clients, some on the platform and some off. Demand increased and Jen noticed that she was enjoying her life outside of work more than she ever had before. One year later, the alluring pull of the freedom of being able to set her own hours was too strong.

She quit her job, packed her bag and set her sights on New York City. Because Jen had so many five-star reviews on Rover from her time in Seattle, it didn't take very long to start booking back-to-back house sits in New York. With a carefully planned calendar, she schedules house sits with as much overlap as possible. She's usually booked for five nights per house sit and her daytime pet sitting hours depend on how much she wants to work in a given week. Worst case scenario, she budgets money for nights when she doesn't have anything booked and needs to stay at a hotel, which is usually only around five times a month.

Otherwise, she is typically found in a fancy apartment in midtown Manhattan, ideally one with a rooftop pool. Living in New York City can be a serious financial burden, but through house and pet sitting, Jen has been able to earn between $60,000 to $100,000 a year and save up to $40,000 of it. This is because she doesn't have to worry about rent, most other bills, or even if she forgot to buy enough toilet paper. She just needs to cover her food and cell phone bill, which runs here under $600 a month. And all she needed to get started with Rover was an initial background check that cost her $25.

Now, here's some more details about the lifestyle of a professional pet sitter. Since she moves between houses so often, she's become an expert packer, with most essentials fitting into a carry-on bag. She also rents a storage locker to store her seasonal clothes, but Jen says she usually has everything she needs in that one carry-on bag. The lifestyle comes with a lot of flexibility, but also responsibility. Jen can usually be found taking care of up to eight dogs from 11 a.m. to 3 p.m. on weekdays.

Holidays can be busier, and she says it's not unheard of to be in charge of 15 to 20 animals at once. With this kind of workload, Jen charges $50 an hour for pet sitting, and around $70 a night for pet and house sitting. She usually makes at least $180 a day while working seven days a week. Slower days might be $120, while holidays like New Year's and Memorial Day can bring in $300 a day or more. Since the holidays are so lucrative, she has to be strategic about when she takes time off.

But all that income, combined with a very frugal lifestyle, means that Jen can build a serious stash of savings. Last year, for example, she managed to save $45,000 and still take 10 weeks of vacation. Jen is the first person to admit that this new side hustle turn full-time career might be stressful to some people, but she says it's perfect for where she's at right now. She's single with no kids, doesn't have a lot of stuff to cart around, and doesn't mind packing it all up every five days. Her long-term goal is to save $500,000 and retire early.

She'll live off her savings, frugally, while making her way around the world for free, using, you guessed it, international pet sitting. The possibilities are endless. [Music]

So, the dog sitting life, especially the professional pet sitting life, is definitely not for everybody. I personally would not want to be a professional pet sitter. Even though I like animals and pets, especially cats, I wouldn't want to be a professional cat sitter.

And of course, most of our listeners are not looking to go full-time into a new profession. They just want to make some extra money or create the possibility of doing something bigger in the future. So, for our animal-loving listeners out there who would love to walk dogs and hang out with a dozen different dogs every day, you might want to look into this. And if you do, one thing that's important, I remember this from working on the previous episode, over time, you're actually going to make more money to transition off the Rover platform. Rover is great for lead generation and building up clients, but they take a pretty substantial commission of their own.

And that's their business model. That's how they're able to raise more than $100 million in funding. So what Andrea did in the previous case study, she started with Rover, but then over time as she built relationships and got referrals, she did less and less of her business from Rover and more and more of it directly, which meant she was able to make a lot more money. And at that point, she's also building up more of a business as well, because she's not confined to the platform. If the platform goes away or if she gets like a lower ranking or something in the algorithm, it doesn't matter because she's built those relationships directly.

All right, friends, thank you so much for listening today. I hope your holidays are still going well, much more to look forward to in January. Today's show notes are at sidehustleschool.com/726. We'll tell you more about Rover and that other case study, anything else that we can think of. And of course, I'll be back once more tomorrow.

My name is Chris Guillebeau. This is "Side Hustle School."