Today we’d like to introduce you to Jonathan Cuilla.
Hi Jonathan, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
My career path started out like most, job to job in hopes of more pay or better benefits. When I became a Sheriff’s Deputy, I thought that was going to be it and the next 30 years of my life. I’m thankful for my time there as it did teach me discipline, leadership, and how to connect with many different types of people. Along the way I co-founded and grew a pest control company and even built a taproom brand before fully committing to entrepreneurship and leaving the Sheriff’s Office completely. In 2023 my family and I spent 17 months traveling the country in our RV while I ran my business remotely, which reinforced my belief that work should support the life you want to live. After settling in Tennessee, I launched Howdy Doody, a pet waste removal service built around simple systems, strong branding, and a little humor in a not-so-glamorous job.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
Entrepreneurship is definitely not the smoothest road to travel. Like most founders, I’ve had seasons where cash flow was tight, plans didn’t go the way I expected, or outside factors—like the pandemic—forced major pivots. Those challenges taught me resilience and how to adapt quickly, which has become one of my biggest strengths as a business owner. Every setback ended up sharpening my focus and helping me build stronger, more sustainable ventures.
Alright, so let’s switch gears a bit and talk business. What should we know?
Howdy Doody is a subscription-based pet waste removal service that helps homeowners keep their yards clean without having to deal with one of the least enjoyable chores of dog ownership. We specialize in simple, reliable service—typically weekly or bi-weekly visits—so customers can spend more time enjoying their yard and less time worrying about cleanup. What sets us apart is our focus on branding and customer experience; we lean into a fun, memorable identity while still operating with professional systems and dependable service. Brand-wise, I’m most proud that we’ve turned an unglamorous job into something people actually enjoy interacting with, and our goal is to become the most recognizable and trusted name in pet waste removal in Nashville and the surrounding suburbs.
How do you think about happiness?
What makes me happiest is building things that create freedom and opportunity for my family. Entrepreneurship allows me to be creative, solve problems, and watch ideas turn into real businesses that serve people in our community. I also love the process—the early mornings, the risks, the growth—because each challenge pushes me to become better. At the end of the day, knowing my work supports my family and helps others along the way is what makes it all worthwhile.
Pricing:
- Weekly service for just 14 bucks!
Contact Info:
- Website: https://www.howdydoodyco.com
- Instagram: https://www.instagram.com/howdy_doody_co/
- Facebook: https://www.facebook.com/profile.php?id=61578823724404
- Yelp: https://www.yelp.com/biz/howdy-doody-spring-hill?osq=howdy+doody&override_cta=Request+information
