Happy Hippie Pickwick

The Happy Hippie

Brian Riley

Brian Riley hails from Memphis, where his love for Memphis basketball and football runs deep. With 25 years of corporate management experience, Brian’s journey is one of leadership, integrity, and innovative problem-solving. He spent 15 of those years at UPS, starting from the ground up as a young adult and rising to the top through dedication and skill in logistics, customer service, and people management.

Seeking a new challenge, Brian transitioned into the school bus industry as a Transportation Director. For a decade, he oversaw operations with a focus on child safety, parent and employee engagement, recruiting, budgeting, and community outreach. His commitment to the community earned him the Volunteer of the Year award from the local Chamber of Commerce.

In 2019, the loss of his best friend of over 30 years to cancer—a fellow music-writing enthusiast—shifted Brian’s perspective. Coupled with the stresses of a COVID-19 school year, he decided to stop watching life pass him by. He listed his house on Airbnb, igniting a spark of entrepreneurial inspiration. What began as a simple hosting gig evolved into a bold idea: a food concierge service for his guests. That vision quickly expanded to serve the entire Pickwick area, and with a playful nod to his free-spirited nature, “Happy Hippie” was born.

What started as a whimsical notion blossomed into a thriving business. After launching Happy Hippie, Brian’s dedication and vision were recognized when he won Hardin County, TN Small Business of the Year. He continues to pour his heart into servicing people, providing a reliable, high-integrity experience that customers trust. Today, the Happy Hippie is more than a name—it’s a testament to Brian’s journey from corporate leader to award-winning, community-driven entrepreneur, living life on his own terms.

Brian hopes that one day is daughter, a University of Memphis Student, would like to manage, own and expand to the Memphis market.

Testimonial

“Brian was a “Grade A+ Host! This was my first time using an Airbnb facility. He took the time and was gracious answering my numerous questions. He also had great communication before, during and after my rental.”

Charles
Client

“Great location! Very nice and spacious! The host responded to every text and answered all asked questions immediately. I will definitely recommend this property and be coming back soon myself!! Ohh and very very clean!”

Nathaniel
Client

"Brian was very responsive and got back to us instantly with questions we had! It was a wonderful place to stay for the week we had a great time visiting for a week in Counce!"

Dakota
Client

“The cottage was just what we were looking for in Western TN near family! Private residence that is easy to find, very cozy and comfortable! Always attentive service from the host, Brian, and great flexibility on check in/out. Easy going and great communication.”

Kendra
Client

“The house was more than I expected. It was amazing. The price was good. It was extremely clean the man that was taken care of the property. Made sure that we were good. He made great contact. This was by far the best stay that I have ever had with any Airbnb.”

Tatramese
Client