This month, we’re thrilled to help Jimmy and his team celebrate all of their hard work as they celebrate the tenth anniversary of Hotel K Pet Sitting & Dog Walking. Located in Madison, Wisconsin, Hotel K LLC had its origins in May of 2016, when Jimmy worked as a solo operator, using index cards and Google Calendar to manage appointments and client information. Eventually, after a little more than a year in business, Jimmy signed up for Time To Pet, hired his first few sitters, and now, ten years later, has built a reputable pet care business built on a passion for animal welfare and a strong desire to give back to the community.
As they reflect on a decade of growth and begin to look forward to the future, Jimmy is determined to move Hotel K to the next level through a campaign his team has dubbed the Belly Rub Reset. As part of their efforts to grow into the future, Hotel K is looking to expand its service area to provide premium pet care to even more Wisconsin families and establish an emergency fund that will provide subsidized or completely free services to members in their local community who are on a fixed or low income or facing unexpected medical crises. To learn more about Hotel K’s incredible campaign or to lend a helping paw, check out their website here and Belly Rub Reset information here!
What caused you to get into pet sitting/dog walking?
My wife and I have cared for animals for friends and family our entire lives. The real catalyst happened when we bought our first house in Madison back in 2007. It had this fantastic, large fenced-in backyard, and by 2008, our network naturally started asking if their dogs could vacation at 'the K's' while they traveled.
That backyard is actually where the business name came from! One of our very first 'guest dogs'—a sweet pup named Ellie—inspired it. Her owners would excitedly tell her, 'Ellie is going to Hotel K!' And the name just stuck.
For about six years, we ran a bustling home-boarding operation fueled entirely by word-of-mouth. Around 2014, the requests started shifting toward house sitting, dog walks, and cat visits. I realized this wasn't just a side hustle anymore—it was a true business opportunity waiting to happen. I put together a formal business plan, built our first website, and officially launched Hotel K LLC in 2016.
What is the most fulfilling part of owning a pet sitting/dog walking business?
I absolutely love pet sitting! At my core, making a tangible difference in a pet’s life—keeping them safe and genuinely happy—is the ultimate reward. I’ve always had a keen sense for connecting with animals; I instinctively know how to 'read' a dog or a cat, respect their boundaries, and patiently earn their trust—especially the shy or anxious ones.
Beyond the animals, I am a total customer service nut and a complete geek when it comes to scheduling logistics! I pride myself on a background dedicated to perfecting the client experience. Marrying that love for backend organization with top-tier hospitality ensures our human clients have the best, most anxiety-free pet sitting experience possible. Seeing that perfect harmony between a happy pet and a relaxed owner makes all the hard work worth it.
What is the most challenging?
The most challenging part of owning this business boils down to two things: accountability and control. First, when things go wrong, and it’s my fault—as much as we try to be perfect, human mistakes happen. Owning that failure is a heavy weight. But even more challenging as a business owner is when things go wrong completely outside of my control, like a sudden emergency or a structural curveball. However, I’ve learned to thrive on both of those challenges.
When the unexpected happens, my immediate focus is on how to right the wrong in the most efficient, transparent, and equitable way for everybody involved. Turning a stressful situation or an unforeseen mistake into a masterclass in customer service and safety is tough, but it is exactly what separates a professional company from a casual hobby.
Where do you see your business in five years?
To tie this directly back to our biggest challenges: thriving under pressure and righting wrongs equitably is exactly what sparked our 10-year vision, The Belly Rub Reset. I looked at the industry's structural bottlenecks and the lingering financial hurdles of the post-COVID era, and I decided it was time to actively build the future we want to see.
In five years, I want Hotel K to be the gold standard for premium pet sitting and employment in Madison, WI and Southern Wisconsin, fueled by our crowdfunding campaign's 'Four-Legged Plan.'
Our primary, immediate milestone is executing our IC to W-2 workforce transition. We are moving away from the traditional independent contractor gig model to build a fully protected, highly trained W-2 professional employee workforce with stable income, worker protections, and true career paths.
Geographically, we are focused on eliminating our remaining legacy liabilities so we can aggressively fund our regional expansion. We are scaling outward from Dane County deeply into Columbia, Dodge, and Rock Counties. Over the next five to ten years, the ultimate goal of the Belly Rub Reset is to scale our infrastructure to proudly serve all of Southern Wisconsin with a reliable, community-first standard of care.
What has TTP changed the most about how you run your business?
When we officially launched Hotel K back in 2016, we ran operations using a basic Google Calendar and actual physical index cards for our client information. As we naturally grew, I quickly realized there had to be a better, more secure way to manage the chaos. I found Time To Pet and officially onboarded our business on September 1, 2017.
From a business and logistical aspect, it was an absolute godsend. The ease of scheduling, the robust reporting, and the ability to maintain constant, seamless contact with both our clients and our sitters changed the game. From a marketing standpoint, it has been pure gold. Clients consistently cite having a sleek, professional app to run our business as one of the absolute best aspects of Hotel K, perfectly matching the elite customer service and care quality they receive.
To put the impact into perspective: since launching on the platform on September 1, 2017, through the year-end of 2025, we have processed over $1.7 million in sales entirely through Time To Pet. It hasn't just been a tool for us; it has been the literal technological backbone that allowed us to scale from a backyard hobby into a powerhouse.
