4 life lessons for new HOA property managers

Melissa Gentry
| 5 min. read
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Editor’s note: This month, we reached out to Melissa Gentry, Owner and COO of Hill Country Homeowners Association Management, and asked if she could share how she got into the business along with her advice for those who are starting a property management company. Instead of doing an interview format, we wanted to get a personal account straight from the source. It’s always humbling to hear hard-fought startup stories, and Melissa’s emotional account is no exception.

I’ve owned Hill Country Homeowners Association for 10 years this month. Wow. It feels surreal to actually write these words. This crazy journey is difficult to describe. The last decade has been a roller coaster of exhilarating highs and excruciating lows. Now that I sit down to put it all in writing, I realize I wouldn’t have had it any other way.

When anyone asks me how I came to start Hill Country, I always joke that I fell into it—literally. Due to a freak accident involving river rocks and a pitch black restaurant parking lot, I broke both of my ankles! It took six very long months of bedrest to recover; and through an equal mix of boredom and a growing dislike of my current job, Hill Country Homeowners was born.

With a decade of experience, I’m always happy to share my advice with the new generation of property managers looking to get into the business. Here are my top 4 pieces of advice for those starting up.

Lesson #1: It’s Not Business, It’s Personal

First and foremost, we are a local, family-owned business that specializes in personalized financial, administrative, and property management for homeowners associations in San Antonio and the surrounding areas. As a business owner, I take pride in my successes and thrive on building direct relationships with my board members. I enjoy working within the small business, family-owned environment I’ve created. It gives me freedom to focus on balancing work and family, while allowing our team to share in our successes and lean on each other when the road gets rough.

Hill Country Homeowners Association Management
Melissa Gentry of Hill Country Homeowners Association Management with her extended work family.

Lesson #2: Keep an Open Mind to New Possibilities

No little girl or boy dreams of managing HOAs while growing up. My business was born of a mix of unexpected life experiences and opportunity, as I mentioned. I bought my first condo at age 19 in Tampa, Florida and became the president of my condo board. From there, I worked in association management while I earned both of my business degrees. Fresh out of school with my shiny new MBA, I decided I wanted a new career path and found myself in management for a financial services company in San Antonio. I bought a house and I became the president of the HOA. I quickly fired the management company and began to look for a new one. I discovered that unlike Florida, San Antonio did not have a large, competitive market for association management. I made a mental note of that potential business opportunity and put it on a shelf. After very little convincing of my fellow board members, I began self-managing the HOA and started my very first association with Buildium.

Lesson #3: Adversity is an Amazing Opportunity for Growth

So, back to that fall. Fast-forward 4 years, and due to that unusual accident, I pulled that dusty idea off the mental shelf and hung out my virtual “open for business” sign. Within 4 months, I had replaced my salary and was officially self-employed! From the day I signed my first contract, I began my partnership with Buildium. I’ve grown as they have grown; and 10 years later, Buildium is still the best financial-inclusive property management software out there.

Lesson #4: The People You Start with Are Not Always the Ones Who Grow with You

This journey has not been without heartache and difficult lessons learned. Through the years, I have lost a best friend and partner through theft; buried a husband; suffered the betrayal of having trusted employees attempt to steal my business out from under me; and most recently, I am still learning how to navigate life with a chronic, debilitating disease.

From these challenges, I have grown as a person; married my best friend; and expanded my business with trust and faith in my team. I still manage the first property that I signed when I hung that sign up, and I count their president as a dear friend. These are accomplishments that, at some points, felt impossible; but with determination, hard work, and an open heart, I am proud to say that Hill Country Homeowners is stronger than ever, growing organically year after year, and standing tall upon a foundation of love and family.

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Melissa Gentry

Melissa Gentry

Melissa has over 20 years of property management experience with condominiums and single family residences. She began her management experience as president of a condominium board in Florida. Since then, she has been involved with the creation of new homeowners associations and has handled everything from sinkholes to legal disputes. No property is too big or too small: Her properties range from annual budgets of $30,000 to over $1,000,000.

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