Red Rover, Red Rover, Send All Your Dogs Over!! Lessons & Tips From My Dog Sitting Side Hustle…

Moving to Denver last year came with many financial changes, the worst of which was higher rent, but the hardest was paying for a dog sitter.   Up until that point, any time I worked or went on vacation I always had Bubba taken care of by either my mom or a string of friends.  In return, I often watched their dogs when they went out of town.  It was nice to be able to leave her in the hands of someone I knew would love her like their own.  Moving to Denver changed that.  I had to start relying on people I didn’t know and people who didn’t know Bubba.  On top of that, the price tag wasn’t cheap.  I paid $35/night and $16 a walk every time I had to go to work as well as any time I traveled.  I love my dog, she was and is worth every penny, BUT IT STILL ADDS UP!!

In August of last year, I decided to offset the cost of hiring a dog sitter by becoming one myself.  I already take Bubba out, feed her, and walk her on the daily… why not add another set of paws to the mix?

Now, Denver is a city FULL of dogs and unfortunately, dog walkers, but I realized I could probably steer a few clients way by undercutting the competition.  I joined Rover (More info & Tips below), an easy to use dog walking/sitting app, and set my prices $5 under anyone who lived within a few blocks of me.  I didn’t have any “real” reviews (you can have friends and family write in reviews but they don’t count as “verified” stays) so when creating my profile, I made sure to make it as lengthy and detailed as possible, adding a bunch of pictures with me and other dogs.  It wasn’t long before I got my first client, Tex, a 60lb 4-year-old German Sheperd mix.

It is important to point out that while living in Denver, I was also living in a tiny home.  A tiny 230 sq ft home with very little space to break up a possible dog fight that might ensue with territorial pups.  I asked the owner to meet Bubba and me at a park to ensure our dogs would get along.  Tex danced around Bubba while she sniffed the grass and ignored him completely.  Within 5 minutes it was clear that neither dog would have an issue with the other.  I booked the client.

Tex, the Squirrel Chaser

A few days later Tex was dropped off at my house.  He came with a crate, toys, food, and treats as well as directions NOT to let him roam off-leash.  My dad happened to be visiting that week so after the dogs got settled in the yard and house, we took them on a walk to the park.  All went well until Tex spotted a squirrel and took off dragging my dad behind. Clearly, that leash rule was a necessity!  After a few more squirrel encounters we headed back towards home happy not to have caught any squirrel trophies.


A couple days later, Tex’s owner picked him up and a few days after that I had $48 deposited into my account.  Tex became a bit of a regular and I quickly got used to walking him and avoiding his triggers.  (Side note – Tex was also featured in my recent Marketwatch video.  Not bad for a rookie!)

Durango and the Missing Sock

Next was Durango, a handsome 80lb 2-year-old Doberman.  I was told he “loves to play with other dogs and cuddle with his humans”.  Again, we did a meet and greet at the dog park and Bubba, for the most part, ignored Durango and any attempts he tried to make friends with her.  If you haven’t noticed, this tends to be a theme for Bubs.  A few days later Durango was dropped off and it was then that I realized how much space an extra 80lb figure took up in the tiny home.

IMG-0425 (1)

Look at that face!!

His owners were right, Durango loved to play with other pups.  He also liked eating socks.  After I noticed one go missing, I kept a keen eye on his poop waiting for it to digest.  Day 1, nothing.  Day 2, I took him to the dog park hoping a bit of exercise would get his digestive tract moving, it didn’t.  Instead, in full-on play mode, he refused to leave the park.  Every time I walked toward him to put the leash on, he would run.  I then tried the toddler method of reverse psychology, hoping if I walked towards the gate and pretended to leave, he would get scared and come running.  Durango slowly trotted behind me but as soon as I turned to leash him, again, he ran – the opposite direction.  By this point, other owners were watching this dance with sheer glee, grateful not to be me at that moment.  After a few more attempts, I cooked up a scheme with another owner.  With Durango watching, I left the park completely.  After a few minutes, he went towards the gate to see if I was going to come back. He was smart, but not smart enough. While his attention was fixed on me, the other owner managed to grab and leash Durango.  Sucker!  We walked the 6 blocks home, still no sock.  An hour after our walk I heard him puking near the doorway and sure enough, out came the sock.  Crisis averted.

A few days later Durango was picked up.  In 3 days I made $96 + the start of an ulcer.


After the first couple of sits, like anything, it got easier.  I have since watched 15 different dogs ranging from mellow (nearly comatose) to hyper, tiny to huge, 2 months to 12 years old.

While most of the dogs I watched have been great, a few have been standouts…

Do De Oh Dudley

Last week I watched Dudley the Studley, weighing in at 185lbs of goofy oafishness.  Bubba was super intimidated by Dudley so I had to keep them separate for the day.  Once he calmed down from the excitement of a new place, he slept like a big GIANT baby.   It was a great experience to watch Dudley and I was happy I got to test my comfort level a bit.  It isn’t every day you get to walk a beast that weighs more than you!  If I could get Bubba on board, we would take Dudley again no problem.  Until then, the $20 I made wasn’t worth the stress to poor Bubs.  Me watching dogs doesn’t just affect me, it affects her too.  A great lesson in itself!

No No Romeo

That same night Romeo, the diaper-wearing 5 lb polar opposite of Dudley, was dropped off (see photo above of the same bed under Dudley!)…

I should have known I was in trouble when he walked into the house and immediately took a dump on my doormat.  Later, he christened the bathmat as well.

Losing two rugs was nothing compared to the sleep we would lose that night while Romeo desperately tried (and failed) to live up to his moniker.  All he wanted, besides to shit on every carpeted surface possible, was to snuggle with Bubba and refused to take her lack of interest as a sign he should move on. Instead, Romeo howled and cried and paced ALL NIGHT LONG trying to get her attention. She never once gave in.  Romeo didn’t fall asleep until daylight, giving all of us a much-needed break from his high pitched whines.  As cute as he was, I would not watch him again.  The $27.20 I made (plus $5 tip) did not make up for the lack of sleep Bubba and I got…us ladies need our beauty rest!

Sweet Silly Dougie

And of course, most of you met Douglas on Twitter

Dougie was new to everything including his leash, walking up or down the stairs, and crate training.  At only two months old (and only one week with his new owner), he managed to tackled every new challenge with incredible ease…well, minus the hammock.  That he managed to get stuck in at least 3 times during his visit.

I had Dougie for 3 nights over a holiday weekend, netting $96 plus a $40 tip.  I love teaching and training dogs and Dougie helped give me an outlet for that…plus he was a genuine pleasure!  Hands down one of the best pups I have worked with and I would jump to watch him again.


In less than a year, I am proud to say that my profile now boasts 21 5-star reviews (So important!! See #6 in the Owners Tips below) and I am one of the top walkers in my area…and competitively priced, no longer underpriced. My calendar is booked nearly every weekend and some weekdays so I can afford to lose a few clients over my higher rates. It is a side hustle, after all, so I can be choosy with which clients I take.

Financial breakdown thus far:

  • 2018 – $252
  • 2019 – $591 ($375 of which was made in the last 2 weeks)

I currently have $470 in upcoming visits already booked and additional requests being made every few days…apparently living in a resort town can be highly lucrative!!

But as you know, it isn’t just about the money for me.  It’s about my love for animals.  Similar to when I worked in the Montesorri school with the kids or when I work on the plane with our passengers, each dog that gets dropped off or each cat that I visit has it’s own story and personality.  On a few occasions my patience has been tested, but the majority of the time my heart swells with joy seeing each dog come out of their shell and start to trust me.  I think of how many times I have been on the other end, leaving Bubba in the hands of a stranger hoping they have her best interests at heart.  I am grateful that I have been able to provide peace of mind for other owners who may have had the same concerns.  Caring for dogs isn’t making me rich, but it is enriching.  And that to me is a win-win.

Interested in becoming a Rover sitter and/or client?  Here are a few tips to get you on your way:


  1. Be as detailed as possible in your profile:Add a ton of photos of you with different dogs and cats if you wish to watch those as well.  Make sure they are clear and at least a few have your face, specifically your profile picture.
    • Get family and friends to write you testimonials.
    • Check out your competition.  See what people are charging in your area and make your rates $5 lower than theirs.  You can always raise your rates later.
    • Be flexible with dates and times if you can.
    • Be sure of what you are capable of.  I only take one overnight dog at a time.  That provides peace of mind for a lot of dog owners, particularly those with elderly dogs.
    • Make sure the services you offer are worth your time and effort or you will resent that booking later and maybe take it out on the pup.  Definitely, don’t do that. Maybe driving 20 minutes to walk a dog for $15 isn’t your thing – don’t do dog walks.  Focus on the other options like dog boarding or dog/house sitting.  Rover will take 20% off the top of whatever your rates are and don’t forget you will have to pay taxes.  More on taxes HERE.
  2.  Respond to requests ASAP.  Your profile will show your response rate so even if you can’t do it or are unsure, write the client back ASAP.  Something along the line of “Buster is adorable!!  I would love to watch him next week however I am away from my calendar at the moment.  Do you mind if I get back to you in an hour or so?” – then don’t forget to get back to them!
  3. Keep your calendar up to date!!  A banner gets added to your profile in the search results which increases your likelihood of bookings.
  4. Read each prospective clients profile carefully.  For example, I had a booking a few weeks back that specifically said the dog does not get along with other dogs.  Aggressive dogs are a no for me.  I had to tell the lady I could not watch her dog as I had my own at home.  It is better to know exactly what you are getting into.  Another example, had I known about Romeo’s leg lifting tendencies and overall anxiety, I may not have taken him after an already long day with Dudley.
  5. Be safe!!  Again, read profiles carefully.  Meetups with prospective clients that have no profile or photo are a no for me (unless I have someone to accompany me as was the case earlier this week. That client may read this so Hi Chris! Thankfully, my fears were unwarranted.  😉 ).  Your safety is the number one priority.
  6. When you first meet a dog or speak with the owner, SHOW INTEREST IN THE DOG!!  Ask questions, interact.  I feel like this is something I shouldn’t have to say but you would be surprised how many people I interviewed for Bubba that didn’t look at her or pet her once.  Disconcerting to say the least.
  7. Once you have your first booking, follow all of the safety rules given to you by Rover and especially the dog owners.  They know their dog better than anyone and those dogs are your responsibility.  You will be covered under Rover’s insurance but there is nothing worse than a dog getting injured, lost, or god forbid worse, on your watch.  Be careful with them!!
  8. Take a lot of photos and keep your client updated.  I tend to send at least 3 messages a day with multiple photos each time.  Don’t make your client wonder how their dog is doing.  Don’t let them be the first to reach out during their dogs stay.  They will love you for keeping them in the loop.
  9. HAVE FUN!!  If the thought of watching dogs sounds boring or annoying to you, this is not a good job fit.  Leave it to those of us who do enjoy it and find something else that suits you better.



  1. Make a detailed profile page for your pet.  Make sure to include his/her likes and dislikes, habits, quirks, triggers, medical issues, veterinarian numbers, fears, aggressions…anything you can think of.  It will save us calling you in the middle of the night while you are on vacation to find out if your dog eating socks is a normal occurrence.
  2. Interview several sitters in person and see how they interact with your pup (also see #6).  Are they making eye contact with you?  Are they interested in your dog?  Have they asked you any questions?  Be sure your dog will be a good fit with them, especially if they have other dogs in the house.
  3. If you can’t meet your sitter in person, try to make a phone call or facetime with them.  Build some sort of rapport so they feel comfortable calling you in case there is an emergency.
  4. When setting up your drop off and/ pick up times, try to be as accurate as possible.  I often have one dog leaving and another coming the same day.  It is imperative to your walkers’ schedule and your dogs well being to keep expectations or touch base when plans change.
  5. Set your sitter up for success.  If they are walking your dog, make sure the harness fits correctly and is the right size.  I speak from experience – Romeo slipped his harness because it was way too big.  Dudley’s harness was way too small.  It is for the safety of your pet and the walker that the leash, collar, and harness are appropriate to your dog’s weight.
  6. Leave a paper version of directions with your dog – at your house if they are checking in there or bring it with you when you drop them off.  It is nice to have something to refer to quickly without having to rely on your app or computer.
  7. Tip, don’t tip.  It’s up to you.  Personally, I don’t expect to get tips for walks or daycare.  If you leave your dog with me for a week, a tip is always nice.  It doesn’t even have to be cash.  Dog treats, dog toys, poop bags, toys for your sitter’s dog.  If they are working as a dog sitter, most likely those things will always come in handy. Again, it’s never expected but always appreciated.
  8. PLEASE LEAVE A REVIEW!!  If you read this far you know how important it is for the sitter to get feedback but also for other pet owners to read them.  This is your chance to give kudos or give warnings.  Be kind, if you can, but be honest.  Here’s why…   A few years back I had a sitter for Bubba that was terrible.  She wasn’t mean or bad to Bubba but she was completely unreliable.  She was late almost every time she sat and, on one occasion, managed to get locked out.  She was absent-minded and didn’t follow directions.  If I didn’t have a senior dog who hated walking or if I felt I had a better option at the time, I would have fired her earlier.  Here’s the thing – I never wrote her a review.  I figured if I didn’t have anything good to say I should say nothing.  Out of curiosity, a few months back I looked at her profile.  Someone had written a review and stated every single issue that I had had with her.  Had I written a review I could have saved this lady and any clients that came after me, the hassle and potentially their dog’s safety while dealing with this walker.  Leave a review.


That’s it!  Want to give it a shot??  If you have not yet signed up for Rover, please consider doing so by clicking this link using my referral code -> ROVER NEW CLIENT AND/OR NEW SITTER.  For any new profile that signs up, I receive a Visa gift card which will help pay for all the new rugs I have to buy after Romeo’s last visit.  😉

**Already a sitter?  Share your best or worst story in the comments!  Any lessons you can share are helpful as well.**

Until next time…

~ Shortly after posting this I was told that I could no longer dog sit out of the caboose due to a complaint by my pesky neighbors!!  Such a bummer but certainly not the end of my Rover career.~


5 thoughts on “Red Rover, Red Rover, Send All Your Dogs Over!! Lessons & Tips From My Dog Sitting Side Hustle…

  1. Congratulations on achieving FI and thank you for sharing Miss Mazuma, what a well written, funny, and actionable article!

    Since you can no longer dog sit in the caboose thanks to your neighbors have you ever thought of house sitting, or having someone house sit Bubs in your own home (to cut down on costs)? 

    In total we’ve been on the road nearly 3 years living out of one 36L backpack each (four continents, 26 countries, and ~80 cities) all while having the pleasure of doing 46 house sits. 

    We try to predominantly travel the opportunity instead of the destination to help keep cost down and house sitting has been a huge part of that!

    In other words, if we get a house sit in Switzerland we see what travel and living expenses are in nearby countries and make our plans around that. 

    A real world example would be: house sit in Zurich, Bernina Express train through alps into Italy, Airbnb in Milan, inexpensive flight to Cairo, travel hack hotel in Cairo, house sit in Athens, etc. 

    You may know this already, so please forgive us if you do… but there are several sites out there for house sitting, depending on what type of house sit and location/setting you’re interested in.

    We’ve used both MindMyHouse and Trusted Housesitters, although the large majority of our house sits are from Trusted Housesitters. A Trusted Housesitters membership comes with a higher cost, but there are dozens of new sits listed daily, with many in the US, UK, across Europe, and a few scattered through the rest of the world. They’re the big player in the field (for better or for worse), so the high volume of listings and the intuitive user-interface comes with very high competition in applicants.

    In our first year of long-term travel, we completed 18 house sits and found that we very much enjoyed it. It lets us travel, see new places, live like a local, meet great families, and take care of pets with varying personalities that we get to play with, pet, and love!

    With that being said, keep in mind that it’s not all rainbows and butterflies! House sitting comes with its fair share of challenges and hard work (which you probably realize!). Although, some will have you believe it’s free lodging OMG! It’s more involved than simply a free place to sleep while traveling, there can be a lot of responsibilities so you need to weigh the pros, cons, responsibilities, and amenities of every house sit and choose wisely.

    We’ve written a few articles for our ‘ultimate house sitting guide’ series on what’s house sitting, choosing a service, creating a great profile, finding an awesome house sit, the house sitting process, and what ‘everyday’ life looks like.

    The Ultimate Guide to House Sitting Jobs: Part 1 | What Is House Sitting & Is It For You?

    Safe travels!

    PS Awesome job on the #70kChallenge! We had the pleasure of meeting Mr. and Mrs. 1500 Days, and lots of others in the Colorado FI/RE space when we they invited us to MMM HQ and had lunch with them (and others) the following day.


  2. i’ve never tried the app as a dog owner. i’ve always said this though: if you’ve never had a dog then try dog-sitting and try some different types on for size personalities. don’t be one of those people who adopts a dog and changes your mind. i’ll come to your house and kick you in the butt if you do.

    plus, you can make a few dollars while you figure out what’s best for you.


  3. Great post. I loved hearing about all the different doggos. We used Rover a bunch of times when we had a dog and had great experiences overall, and see it as a retirement “gig” for us one day too.


  4. I love how you love dogs (and all animals). As a little girl you would bring any baby bird that fell from a tree home to nurse back to health … I remember digging in my garden at 4:40 am finding worms for your cherished babies. They would grow feathers and the pride you had once they were able to fly away! You’ve always had a soft spot. I also remember you trying to hide a puppy in your bedroom, Cassidy, found at a concert (you said)! Didn’t take me long to figure that one out once I realized your girlfriends were squealing with glee playing with the little ball of fur. Any puppy you care for is truly lucky… your clients should rest their hearts knowing their fur baby will be cared for with love… love you B. I’m so proud of who you are❤️

    Liked by 1 person

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