We were lucky to catch up with Lorenzo Halloran recently and have shared our conversation below.

Lorenzo, appreciate you joining us today. Can you open up about a risk you’ve taken – what it was like taking that risk, why you took the risk and how it turned out?

When we first began working with retirement communities, it was a complete gamble. We didn’t know whether this transition would be the right move for the business. I was brought on to pilot the initiative with full transparency that there were no guarantees of success.

We ran several free trial programs to test demand. What we discovered was remarkable and demand wasn’t just present, it was overwhelming. Nearly all of our communities signed on after their trial period ended. One community, surprisingly the one with the highest demand, chose not to continue. Instead of letting that discourage me, I stayed committed to the residents. We arranged to continue offering limited services there for free a few hours each week.

For about nine months, I supported residents’ tech needs and sometimes helping 10–15 people within a two-hour window each week. But because of that persistence and support of the residents we were able to get back on site regularly with that community. That experience reinforced my belief in the value of what we were building and strengthened my ability to adapt under pressure.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

My name is Lorenzo Halloran, and I am a Tech Concierge with The Smarter Service. I spent seven years working in sales and was fortunate to find success early in my career. However, despite doing well professionally, I never felt I was truly making a meaningful difference.
I’ve always had a passion for improving the lives of others, which led me to earn my Bachelor’s degree in Parks & Recreation Management from ASU in 2018. Due to job availability at the time, I transitioned into sales. While I focused on selling products I believed in, it still didn’t fully satisfy my desire to serve people in a deeper way.
After leaving sales, I spent three months job hunting and had just one interview—with The Smarter Service. That opportunity changed everything.
The Smarter Service provides individualized, in-person and virtual tech support and education for older adults. I joined the company just as it was expanding into retirement communities. I was brought on to manage our first community and help grow into additional locations and an exciting but uncertain step at the time.
Today, I serve five communities each week along with several private members. My work ranges from teaching residents how to move or delete apps, to setting up new devices, to helping them recognize and avoid scam emails—and that’s just the beginning.
From day one, I knew this was the right fit. I genuinely enjoy teaching and watching residents gain confidence as they learn new skills. The gratitude and progress I see daily are incredibly rewarding. What may seem like a small task to me can make a world of difference in someone’s independence and peace of mind.
One thing I consistently remind residents who feel discouraged is this: “How can anyone blame you for not knowing this? You retired before computers were fully integrated into the workplace. Then suddenly, you were expected to use them daily.” That perspective helps remove shame and replaces it with empowerment.
What sets me apart is not just technical knowledge, it’s patience, empathy, and the ability to meet people where they are. I’m most proud of the confidence I help instill in the people I serve.

Can you share a story from your journey that illustrates your resilience?

When I first stepped into this role, we were navigating completely uncharted territory. We had to pivot and adjust almost weekly because everything was new—both for the company and for me. I was spearheading our expansion into retirement communities, and much of what we built came through trial and error.

There’s a saying about startups: “building a plane while it’s flying.” I can confidently say that’s exactly what it felt like. There were moments of uncertainty, shifting expectations, and constant learning curves. But resilience meant pushing forward, refining our approach, and staying focused on the residents we were there to serve. Over time, we discovered what worked best, built strong relationships, and created a model that truly supports the community.

What’s worked well for you in terms of a source for new clients?

The best source of new clients has been genuine compassion and understanding. Many of the residents I work with feel overwhelmed by technology, and I approach every interaction with patience and empathy.
Word spreads quickly in close-knit communities. As technology continues to evolve, many residents are still learning the basics, and their needs grow daily. I often meet new residents who already know who I am before we’ve ever met because they’ve heard about me from friends. That organic word-of-mouth growth has been the most powerful driver of new clients.

Contact Info:

• Website: https://thesmarterservice.com
• Instagram: https://www.instagram.com/thesmarterservice/
• Facebook: https://www.facebook.com/thesmarterservice/
• Linkedin: https://www.linkedin.com/company/smarter-older-adults/
• Youtube: https://www.youtube.com/@TheSmarterService/videos