From Accidental Landlord to Multi-Family Mogul: My Journey in Real Estate

When I first dipped my toes into the world of real estate, I had no idea it would transform my life. Like many others, my journey began with an unexpected twist—what I like to call an “accidental landlord” moment. But what started as a necessity quickly turned into a passion, and over the years, I’ve evolved from managing a single rental property to building a multi-family real estate portfolio with hundreds of units.

The Accidental Landlord

My entry into real estate was anything but deliberate. In the aftermath of the 2008 financial crisis, I found myself in a position where I needed to move but couldn’t sell my house. The market was stagnant, and selling wasn’t an option, so I did the only thing I could—I rented it out. What initially felt like a temporary fix soon revealed itself as a gateway to something much bigger.

The steady cash flow from that first rental property sparked an idea: if I could manage one property, why not two? And if two, why not more? This simple notion led me to purchase more properties, flipping some along the way and learning invaluable lessons through trial and error. By 2009, I had built a portfolio of 14 properties, including single-family homes, duplexes, and triplexes. However, as my portfolio grew, so did the challenges.

The Roadblocks to Growth

Scaling my real estate portfolio wasn’t without its challenges. Managing 14 properties was time-consuming and physically exhausting. The infamous “three T’s” of real estate—tenants, toilets, and termites—consumed my days and left me with little time to focus on growth. On top of that, securing additional financing became increasingly difficult. Banks were hesitant to extend more loans, and eventually, I ran out of capital to continue investing.

These roadblocks made it clear that I needed to pivot if I wanted to scale my business effectively. I began exploring other avenues in real estate, from self-storage facilities to industrial properties. However, each option seemed to require starting from scratch. It wasn’t until I discovered multi-family real estate that everything clicked. With my experience managing smaller residential properties, transitioning to multi-family investments felt like a natural progression.

The Shift to Multi-Family

In 2019, I made a decisive shift to focus solely on multi-family real estate. This decision wasn’t made lightly. I knew that transitioning from single-family homes to larger multi-family properties required a new set of skills and knowledge. To ensure I was prepared, I invested heavily in my education, devouring every book I could find on commercial real estate and joining a mentorship program with Jake and Gino, who specialize in multi-family investing.

This move proved to be a game-changer. With their guidance, I learned how to acquire, manage, and scale multi-family properties. I also began selling off my single-family assets, using the proceeds to invest in larger multi-family deals. By the end of my first year in multi-family, I had acquired over 300 units, a milestone that validated my decision to shift focus.

Scaling Up: From 300 Units to 15,000

Today, my sights are set even higher. I’m actively expanding my portfolio across multiple states, including Idaho, Oklahoma, Ohio, Texas, and Florida. My partner, Chris Carney, and I are focused on acquiring value-add properties where we can improve operations rather than undertaking heavy renovations. This strategy has allowed us to increase rents and deliver strong returns for our investors, even in a rapidly changing market.

But my goals extend beyond just growing my portfolio. I’ve set a vision for the future: to provide 15,000 comfortable homes for families while helping 200 of my close friends grow their passive income through real estate investments. This isn’t just a business objective—it’s a personal mission to create lasting impact through real estate.

The Importance of Partnerships and Mentorship

One of the most valuable lessons I’ve learned in my real estate journey is the importance of partnerships and mentorship. Real estate is not a solo endeavor; it’s a team sport. From my early days of flipping houses to my current multi-family ventures, I’ve always relied on the expertise and support of others.

Whether it’s working with seasoned operators in new markets or joining forces with partners who complement my skill set, collaboration has been key to my success. This approach has also allowed me to diversify my investments across different regions, leveraging the local expertise of my partners while maintaining focus on my core markets.

Giving Back Through Personal Development

Beyond real estate, personal development has played a crucial role in my journey. My wife and I are passionate about helping others achieve their potential, which is why we founded the Idaho Business Summit—a personal development seminar designed to bring world-class speakers and transformative experiences to our community.

We believe that everyone should have access to the tools and resources needed to succeed, regardless of their background or financial situation. Through the Idaho Business Summit, we aim to empower others to take control of their futures, just as we have done in our own lives.

Looking Ahead: Lofty Goals and Ambitious Plans

As I look to the future, my goals are both ambitious and deeply personal. I’m working towards joining Tony Robbins’ Platinum Partnership, a program that has been on my radar for years. Although the financial commitment is significant, I’m determined to make it happen within the next two years—a timeline inspired by a quote from Elon Musk: “Take your 10-year goal and figure out how to compress it into six months.”

In addition to this, I’m exploring new masterminds and personal development programs to continue growing both personally and professionally. These goals are not just about financial success—they’re about creating a life of purpose and impact, where I can help others achieve their dreams as well.

How You Can Join the Journey

If my journey resonates with you, there are several ways we can collaborate

1. Invest with Me: If you’re looking to diversify your portfolio and gain exposure to multi-family real estate, I’d love to discuss potential investment opportunities. Whether you’re new to real estate or a seasoned investor, I’m here to help you achieve your financial goals.
2. Partner on Deals: If you come across a promising property or know someone looking to sell, let’s connect. Whether I take on the deal or refer it to someone in my network, we can work together to create win-win scenarios.
3. Collaborate on Projects: I’m always open to new partnerships. If you have skills or resources that align with my goals, I’d love to explore how we can collaborate on future projects.

Real estate has the power to change lives—not just through financial gain, but by creating opportunities and building communities. If you’re interested in connecting or learning more about my journey, please reach out through my website, SenateEskridge.com, or find me on social media and BiggerPockets. Let’s build something great together.