Is That Deductible? The Legacy House, Family Gatherings, and Business Opportunities

When you’re running a small business, one of the key questions you often ask yourself is: Is that deductible? As a physician entrepreneur and owner of a micro-corporation, I’ve learned over the years how to strategically manage both personal and business expenses—especially when they overlap. Recently, I had an experience that perfectly illustrates how personal family moments can also be valuable business opportunities, all while taking advantage of tax deductions available to entrepreneurs. Let me walk you through a holiday season spent with family at our Legacy House, a short-term rental (STR) right across the street from our primary home, and how this business space also serves as a gathering place for unforgettable moments.

The Legacy House: A Gathering Place and Business Space

Our Legacy House is an 1870s home that we’ve completely remodeled into a beautiful, three-bedroom suite property. Each suite is named after our parents who have influenced us. I come from a divorced family, so I have two sets of parents, and I also have my late wife’s parents, who have been a significant part of my life. We have stories and pictures that respectfully describe their lives to ensure their legacies live on.

The home has a huge kitchen, a spacious gathering room, and is the perfect space for family events. This year, we were fortunate to host my late wife’s family for a combined Christmas and New Year’s celebration. The family came in from three different states, and having them stay together in such a cozy, well-equipped house was an absolute joy. We had a great time playing games, sharing meals, and enjoying each other's company. But here’s where it gets interesting from a business perspective: because we operate the Legacy House as an STR business, the upkeep, maintenance, utilities, internet, and other operational costs are all deductible business expenses. This includes the parking lot we built this spring to accommodate four additional parking spots.

You might be wondering, how does this all work from a tax perspective? The key here is that when you turn part of your personal property into a business space, those expenses become business expenses. Even if the property is being used for a personal family gathering, you can still deduct the costs associated with maintaining and operating it as a business. Whether it’s utilities, repairs, or even renovations, as long as it’s tied to the business function, it can likely be deducted. That means that the time spent with family in this beautiful space also has financial benefits for my micro-corporation—making it a true win-win.

An Unexpected Business Opportunity: Feedback on ChatRx

While family time at the Legacy House was already enriching, it turned into a great business opportunity as well. As part of the holiday festivities, I was able to have in-depth discussions with family members about ChatRx, the telemedicine SaaS product that I’m passionate about and that is also part of my business operations. Specifically, I got invaluable feedback from my brother-in-law, who works as a business marketing analyst for Nielsen in Chicago. He’s one of the sharpest business minds I know, and as we sat around playing Trivial Pursuit—with him and his family trouncing the competition—I mentioned my work on ChatRx.

He has experience from working for a startup SaaS company a decade ago, so his feedback was especially helpful. After explaining the core product, he shared his thoughts on the lean business model, its scalability, and the potential for success. It was both humbling and exciting to receive his affirmation, especially because his feedback aligned perfectly with my vision for ChatRx’s bright future!

A Family Connection and Product Development Pivot

While the marketing analysis was incredibly encouraging, it wasn’t the only insightful conversation I had. My nephew, who’s in his late twenties and has a background in computer programming and tech, has been working all over the world. He’s currently pivoting his career by enrolling in nursing school, with the goal of becoming a CRNA. It’s always exciting to see younger family members taking new directions, and my nephew’s passion for learning is truly inspiring. He’s also built a nurse study app prototype, which I had the chance to review during our holiday gathering.

As you can imagine, he was quite interested in ChatRx, especially as a tech enthusiast with programming experience. He took some time to explore our prototype platform and was impressed with what he saw. He even trialed the AI-driven symptom checker, where I invited him to “trick or beat the AI agent.” The good news? He managed to trick the AI into missing a diagnosis of an acute meningitis case—which is a condition that our product isn’t designed to handle (since it’s tailored for the treatment of 35 common acute infections).

While that might sound like a failure, it actually highlighted a gap in our product design—one we had accounted for within our emergent conditions recognition system—that it still needed some refinement. His input led me to a significant pivot point in the development of ChatRx: We needed to enhance and deepen our robust risk management recognition system within the platform. This quality improvement process will enable our AI agent to better recognize when an emergent diagnosis falls outside the scope of treatable conditions and requires an urgent doctor visit.

Although my nephew's advice didn’t cost me anything (thank you, family discount!), the value it brought was immense. In fact, it set me on a new path to architecting the training steps for our AI agent using Large Language Models (LLM) and Natural Language Processing (NLP)—two of the most cutting-edge technologies in AI development. These steps will be critical for improving ChatRx’s clinical accuracy and helping it better align with regulatory standards.

Why This Experience Matters to You

You might be reading this and thinking, That sounds great, but how does this relate to me? Here’s the thing: running a small business doesn’t happen in a vacuum. Whether you’re managing a micro-corporation or another type of entrepreneurial venture, feedback from family, friends, and even casual conversations can lead to unexpected insights. As business owners, we need to be open to the advice, suggestions, and critiques that come our way—whether from seasoned professionals or tech-savvy family members. These moments might seem like just part of the holiday festivities, but in reality, they are opportunities for innovation and growth.

Additionally, it’s worth remembering that your personal life and business life are often interconnected. By strategically turning part of your personal assets into business expenses—like I did with my Legacy House—you can optimize your tax deductions and improve your bottom line. This approach requires a mix of business acumen and creativity, and the tax benefits can be substantial.

How You Can Learn from My Experience

If you’re looking to elevate your business, particularly in the medical field, and create opportunities like I did with ChatRx, I invite you to explore some resources to help grow your micro-corporation:

• $2000 SimpliMD Business Coaching: Receive 1:1 holistic coaching tailored to small business growth, with flexible monthly or quarterly programs to fit your needs. Together, we’ll strategize on how to take your business to the next level.

• $199 Creating a Practice Without Walls Course: Learn how to launch your own virtual professional micro-corporation and thrive in the expanding marketplace. This comprehensive course will guide you through the steps you need to take to build a sustainable business.

• $99 1:1 Micro-Business Consultation: Work directly with me to evaluate your professional life and explore how a micro-corporation can elevate your career.

By embracing both personal and business opportunities, as well as seeking feedback and advice, you can continue to evolve and expand your business model while enjoying the rewards of both professional and personal fulfillment. I’m excited to see where ChatRx goes in the future, and I’d love to support you in your journey as well.