So What the Hell Happened? Part 2 of 5: Dog Sitting!

August 19, 2017 Posted by Tyler Cruz

Continuing on from where I left off in part 1 of my “So What the Hell Happened?” series, let me set the scene: I am depressed and trying to cope with my relatively recently acquired Meniere’s disease, while also being depressed about my affiliate campaigns tanking and my Votesy venture failing to take off. I am tired of the Internet and need a change.

At this time, our golden retriever, Zipper, was around one-and-a-half and so our house (which we had just purchased just under 2 years prior) was already doggy-proof. I’ve also always loved dogs and always used to toy with the idea of running a doggy daycare or providing some other type of dog-based service. Also, I found a really good Bobby Bed that he enjoys sleeping on. I wanted to work with something I enjoyed doing, and so naturally the idea of running a dog-sitting business came to mind.

If you are in the market for a particular kind of dog accessory or item for your own pooch, you will want to take advantage of checking out some dog accessories reviews so you can get all of the information you need about a particular product. This is a good idea for anyone who is going to be purchasing any kind of dog product and you want to be sure that you are getting your money’s worth. Checking out dog accessories reviews is also a great idea if you are interested in getting the best deal possible on a particular item such as a dog harness or a dog bowl. By checking out a few different ones you will be able to get a clear picture of exactly what each company has to offer.

It was such a drastic change, going from working online for the past 12 or so years, to dog sitting, and it’s incredibly embarrassing to share this with you, but this is what happened (and I have the photos to prove it!). When you’re in a tight spot and need money to pay the bills, you will do whatever is necessary to do so, whether that’s taking a job at McDonalds, washing dishes at a restaurant, or looking after other people’s dogs in your house. Getting a real job would have been the easy answer, but my Meniere’s disease would not allow this.

Starting the Business

I didn’t do much – I created a GMail account for dog sitting and posted ads up on Craigslist, Kijiji, and another local classifieds site, and also put up flyers around town (yup… it actually resorted to that!) although the flyers didn’t bring in any leads.

Fortunately, it was late November or early December when this happened and so we actually had a fair bit of interest despite minimal advertising, since people were going on vacation for the Christmas holidays and needed somebody to take care of their dog.

Living with Dogs

It started with 1 extra dog which went fine. Then 2. Then another. And another, one of them is sick and I had to buy his medicines at Then, we also had to Buy Natural Pet Food.

“Happy”, the smaller dog, being unsure of living with 3 big dogs in the house.

Keep in mind that these were all long-term stays – between 2-4 weeks! So, they slept in my bedroom with me. And if you’re looking for a new bed for your dog then you should get one of these amazing personalized dog beds as you can use your own photo or design, so you can design it as you’d like.

We had to set a limit at 4 dogs as we felt that we couldn’t reasonably take care of any more than that at the same time, especially since each dog had special issues! I started giving them hemp infused dog treats to calm their nerves and treat their tumors. We all know that CBB does great things, just look at how many products offers.

For example, one dog (the Weimaraner above) was fantastic except she had separation anxiety from her owners and was very skittish and alert to any noise which is one of the reasons why the doctor prescribed CBDDY: delta syrup.

She also barked like you wouldn’t believe, and had the loudest bark ever. At night she would bark at the faintest noise and go crazy at night – the first few nights were the toughest. Thankfully, there’s cbd for dogs to help calm her down.

The larger Golden Retreiver above (Benji) was the sweetest dog EVER, but he was extremely old (around 13 or 14) and had trouble walking and getting up, so he needed extra care. He needed supervision when using the stairs, we would hand feed him sometimes since he had trouble standing up, etc.

The corgi mix above (Happy) needed to be given medicine twice a day and the medicine made her pee on the floor a few times! She also had some odd alpha dominant behaviour towards the other, bigger, dogs, and our dog Zipper was ignoring it for the most part, but I could see that he was at the end of his rope and was not going to take it for much longer. Learn about the japanese chin toy dog breed if you’re planning to get one.

Dogs everywhere!

Crazy Owners, Crazy Dogs

I ran into a couple interesting situations where I had to turn away the dog after they showed up.

In the first case, it was a tiny puppy that was extremely timid. But the problem wasn’t the dog so much as it was the owners – and after meeting the owners you could quickly understand why the dog was so timid. Granted, it was a puppy and they were new owners, but they babied the dog like you wouldn’t believe – despite our dog being friendly, it would hide behind his owners and the owners would pick it up and coddle it, and basically were helicoptor parents – always within inches of their dog, ready to swoop him up in an instant, and that’s why they use an harness, since a puppy harness and leash set isn’t going to be as large as the one for bigger dogs.

I explained to them that it probably wouldn’t work out since they obviously didn’t feel comfortable leaving their dog with us. By the way, they were at our house for over 2 hours making sure their dog would be okay being left with us.

Zipper and Dewdney chilling

In the second case, the guy had contacted me a day or two prior, stating that Rottweiler was super friendly and loved other dogs and was just a big “puppy” and wouldn’t hurt a fly. I was nervous about at first, it being a Rottie and all, but decided to give him a chance as I’ve heard that Rotties can be one of the most lovable dog breeds out there.

When the guy arrived, I could see him struggling up our driveway. First, keep in mind that this guy was a massive, tough looking giant, with tattoos, leather jacket, and the works. He was probably at least 6’3 and just simply huge. Yet, he was being not pulled but dragged up our driveway by his dog. That was red flag #1.

Red flag #2 was when I saw the Rottweiler, and he was one of the biggest dogs I’ve ever seen in my life! And pure muscle! His claws were simply ridiculous and literally looked like a bird of prey’s talons (I didn’t know a dog’s claws could get so big and sharp). He also had a studded choke collar.

Red flag #3 was when I had him take the dog to the back yard before I intoduced him to our other dogs and he still couldn’t get his dog under control. Remember, this was an absolute giant of a man and he couldn’t even get his beast of a dog to sit or even stand still.

Despite all these red flags, I could see that the dog was just excited and wasn’t really showing any aggressive behaviour, so I took out one of the dogs to let them meet (with him holding onto his dog tightly), and the other dog immediately jumped onto the other dog. It was a playful jump, but this dog was probably 150 pounds and it obviously not know how to play with other dogs properly.

Remember that the owner had drove 3 hours to our place and I had told him before that I could accept his dog (from how he described him to me via e-mail), but after all of this I had to build up the courage to tell him that I was responsible for the other dogs safety and had to turn him away. I felt absolutely terrible doing this because he did drive so far and would have to drive back 3 hours, and he had no other place to go since he was going somewhere for Christmas later that day and all the local kennels and places were booked solid. I felt so bad, but I had no choice.

Pros and Cons

It was such an adjustment to suddenly live with 4 dogs. Here are the pros and cons I found with dog sitting:


  • Returning home was awesome; you got 4 dogs waiting to greet you, all super happy to see you. I will definitely miss that.
  • It was cool to see different dog breeds and personalities
  • They money was actually pretty good


  • We always needed somebody to stay at home to look after the dogs, so my girlfriend and I couldn’t go out at the same time
  • The smell in the house was ridiculous. It smelled like a barn. You didn’t notice it though until you left the house and came back
  • All dogs had certain issues. This makes sense though, as if a dog was perfect, they would like be placed with friends or family
  • Our dog was young and had at the time showed some aggression towards other dogs in the recent past, so we had to screen the other dogs to make sure he could live with them safely
  • Some dogs or owners are simply crazy (more on that in the next section)
  • There is the fear in the back of your mind if something happens to somebody’s dog

Let sleeping dogs lie.

How Was the Money?

The money was obviously not remotely close to the type of money I was used to, but it was actually not bad considering it was just dog sitting.

Here were my rates:

1 hour: $10
1 day (up to 8 hours, otherwise $10 per additional hour ): $30
2 days in a row: $40 or (overnight): $50
1 week: $175 or (overnight): $200
1 month: $500 or (overnight): $600

However, we only ever had dogs for long term (our shortest stay was 2 days, overnight), so if we looked after 4 dogs for 3 weeks, that would be $2,400.

The longer you have the dog, the easier it is as you build a bond with the dog and learn about the dog, and most of the time they will be sleeping, so it’s actually a really easy way to make $2,000-$3,000 a month. However, we only did this over Christmas (Zipper began to attack the other dogs so we had to put an end to it), so my numbers are quite skewed. At the same time, we were brand new and didn’t have time to build up a real business, so there was certainly potential for growth.

Even without long-term stays, taking care of 5 dogs for 1 day would yield $150. If the dogs get along, this is not insignificant money.

Zipper and Dewdney were actually really close friends…

…Until Zipper attacked her over a bone misunderstanding and drew blood!

No More Dog Sitting

Due to Zipper becoming aggressive towards other dogs (he probably missed having the house to himself), we had to stop the dog sitting. We only did it for around 6-7 weeks. Zipper is also now in school for his aggression and has come a long way.

It was interesting though. It’s certainly a viable way to make money if you have a house appropriate for it.

I’ll leave you with a few more photos before I finish:

Zipper and Benji – the two golden retrievers. With all their hair, they always prefer lying right on the ground instead of a bed.

Unfortunately, Benji passed away close to a year after staying with us.

Dewdney is such a diva…

My bedroom in the middle of the night.

Stay tuned for Part 3 of my “So What the Hell Happened?” series. It is a real doozy.

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Posted: August 19th, 2017 under Miscellaneous  

9 Responses to “So What the Hell Happened? Part 2 of 5: Dog Sitting!”

  1. Tushar says:

    Very Interesting story Man. Can’t wait for next article.

  2. Graeme says:

    Loving these Tyler. You were the only internet marketer that I constantly read back in the day and it was always due to your transparency and honesty as well as your quality of writing. It’s really fascinating reading about life after internet marketing. Keep up the amazing work.

    Did you find it really hard saying goodbye to the dogs? If not for your dogs aggression would you have liked to kept going down this road?

    • Tyler Cruz says:

      I only had a real hard time saying goodbye to Benji, the older golden retriever, because the person who picked him up was not the owner but the brother of the owner, and Benji did not want to leave and didn’t understand why I was making him go with a stranger. I almost cried.

  3. Durga says:

    Loving this “So What the Hell Happened?”. I am visiting this site after a long time. When I checked this post, First of all I searched for the first part of this series. I read that and then this one too. I must say I loved it and desperately waiting for other 3 parts. When will you publish the rest of its parts?

  4. mike says:

    I never would have expected a post about dog sitting! But who doesn’t like dogs? I also used to take care of a few dogs myself a couple of times a week but they belonged to a relative so I was doing them a favour. Too bad Zipper didn’t get along better with the other dogs since maybe it could have continued as a part time business?

    • Tyler Cruz says:

      There was definitely potential. I mean, 5 dogs is at least $150 a day – a lot more if you keep them overnight. There are pros and cons like I mentioned, but you could always potentially move it outside of the house into an actual commercial doggy day care, hire employees, and then have a real business running.

  5. Sunfrog says:

    I think Zipper is trying to be the alpha male, which is your job. Watch Dog Whisperer. I also like these blogs of real life instead of marketing and stuff.

  6. Alisha says:

    From the title, It was looking ewwwwww, But I opened it and find that it is really a nice story.

  7. Hello! Tyler.
    It is quite interesting to read the first two parts. I have always liked reading stuff that is not fiction and actually someone’s experience.
    My brother loves dogs, his love turned him into a dog trainer.
    He is just 21 but he has got certifications in dog training and hopes to open a pet shop in the near future.
    This dog training is actually not bad, he is making good money out of it.

    Lots of love from India. 🙂
    P.s- waiting for the rest of the parts.


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